Teaching 14-Year-Old Boys
Teaching 14-year-old boys
Teenage boys are only interested in one thing - sex.
“Then it’s agreed. We’ll shoot Scott,” Doug said, closing one eye and aiming the gun at my head. His finger poised at the trigger, about to seal my fate with a tiny movement.
“Wait a second! Why me?” I demanded. The room stood in silence for a second and then Barrel spoke,
“Well, like Doug said- my parents are home, and his parents are at home but your parents, they’re not at home for an entire week.”
I visibly baulked, “And that’s why you plan on shooting me. Because my folks are at a textiles conference all week?”
An annoyed sigh escaped Doug’s curled lips, “It’s not going to kill you,” he said wildly flinging the gun around with his big hand gestures. He was probably right; the gun didn’t look dangerous at all. It looked flimsy, it looked feeble, it looked plastic. ‘Gun’ didn’t even seem to be the right word for it. For all intents and purposes it was a toy, bright white plastic moulded to the shape of a 1950’s science fiction laser pistol, but I was scared of it. I was scared of what it might do to me.
This all had started about three weeks ago, we walked out of computer class the only class we all had together, Doug, Barrel and I, laughed and joked loudly as we went to get our lunch. As girls sometime do, Julia walked past us. A gust of wind flew by her school-sanctioned skirt and teased us with a hint of the panties that lay underneath. The joking came to an abrupt and succinct halt as we all inwardly thanked whatever god made that that possible.
“Julia’s got the best butt around!” Barrel whispered as soon as she was out of earshot.
“But she’s flat as a pancake,” I chimed in, harsh I know, but true. Julia did have an incredibly juicy derriere, full pouty lips and beautiful long red hair that flowed behind her like a red mist, however she was lacking some major boobage.
“Dude, just wait, she’ll grow a pair. Her older sister is in my advance math class and she has the finest pair going around,” informed Doug, gesturing a cup size that must have been embellished, “Too bad she has acne like a bitch though.” We talked like that back and forward, all through lunch. Judging girls, making lists of whom we wanted to bang. We can be excused for this kind of talk. We are 14 and we are supposed to talk like that!
“What isn’t fair,” started Doug, deciding to make a statement, “What isn’t fair is it’s a the girls choice when to have sex.” Barrel and myself stared blankly at our pontificating friend as he sipped his banana-flavoured milk. He continued, “This whole world is about guys trying to impress a girl enough so that they can grant us the precious gift of sex. I mean sex feels good for them, right? I read it actually feels better for women than it does for men. So, why do they withhold it from us? Why do we have to work long and hard for something that we both would clearly enjoy? It seems stupid.”
“They just keep it from us so they have all the power,” suggested Barrel.
“Yeah,” I agreed. The conversation continued picking up momentum.
“I’m a virgin,” Doug declared. Although we all were, of course we were. We were three teenage boys who always hung out together and blended into the school scene. The female population largely ignored us.
Barrel was exactly like his nickname, big, round and thick. And I mean big. At 14 he was already taller than every teacher in the school but one and easily twice as heavy. Despite his girth, he was a gentle giant, more prone to crying than to throwing punches. He was a good friend of mine, although sometimes just because he made me feel good that I wasn’t as slow or unsuccessful as him. The girls at school would always be scared of Barrel because of his immense size and the fact he’d get so nervous around them all he would do is splutter and breathe erratically.
I was never quite sure what Doug would do when he grew up but I was sure that it would be only semi-legal. Doug was a smooth talker, a person of loose morals. He would have been nicknamed ‘The Weasel’ if he let us, but there was always a fear of getting on his bad side. The girls thought he was sleazy and rightly so.
Rounding out the group was me. If I warranted a nickname it would have been ‘The Sponge’ as I fit in anyplace. I was easily ignored; I was sure most the people in my class didn’t even know my name. The girls certainly didn’t.
But on a whole I think the female population saw us all as ‘immature.’ Nothing more than a little boys group. But here we were making what we thought was the most mature statement anyone had ever made.
“Girls should just have sex with any guy she wants to without all these trials and tests. If it feels good do it!”
“If I was a girl, I wouldn’t hold back.”
“Either would I. I’d spread it around. I’d get good at it. Let guys get good at it so that we all would enjoy it more”
The bell rang and ended our brainstorming. I felt frustrated, Doug had a point. Barrel went home and had an idea, an idea that I would have never thought in a thousand years. And that idea had would cause my life to change in a very big way.
During a sleep over, just after a strenuous bout of video gaming at my house, Barrel unzipped his backpack and removed a box. “Gentlemen, say goodbye to our problems,” he chanted as he lowered the box in front of us. It was a non-descript, smallish white cardboard box, needless to say we had no idea how this would solve all our problems, in fact we had no idea what our problem even was. Wordlessly Barrel flipped off the lid of the box and trumpeted a little fanfare. Inside the box was the aforementioned gun. It was seemed neither impressive nor did it seem to fix any troubles. Barrel smiled warmly at our blank stare, preparing to answer our questions.
“I bought it off e-bay,” he said, not answering the most pressing question. He gently picked it up with his massive hands, showing us the plastic gun. He was being so cautious with it that it could have been a newborn baby.
“Barrel, my good friend, what is so special about a toy?” Doug asked, treating his ‘good friend’ like an excited 4-year-old.
“Well, the guy who was selling it said it was magic,” Barrel paused for dramatic effect for a little too long, “The guy said that it was cursed by a witch about 20 years ago and ever since then its had magical powers.”
“And you believe what you read on e-bay?”
“Well, I’m not sure, but he said I can get my $250 back if it doesn’t work.”
“$250! You dickhead! Isn’t that all your Christmas and birthday money you were saving for a PS3?”
“Yeah, but weigh it up. Magic gun or a lame Playstation, what would you choose?”
“Magic gun?” I finally chimed in, “Barrel, does it even work?” Barrel looked hurt and defensive, mainly defensive.
“I haven’t tried it yet, have I?” he snapped,
The gun definitely didn’t look magic. Doug snatched the gun and aimed it at my coffee table. “Pa-chow” the tinny speakers blared as he pulled the trigger. Nothing happened right away. We waited. Nothing happened then either. Doug seemed disappointed, not at the gun but Barrel’s naivety. “Well, so much for magic,” proclaimed Doug, “It didn’t turn the coffee table into anything.”
“It doesn’t work like that,” sighed Barrel, “Remember I said it would solve our problems?” We nodded. “Well, the guy said if you shoot any person with it,” Barrel emphasized ‘person’, “they turn into a hot babe.”
“Fuck off,” I said, “You’re such an idiot! What a waste of money! How is that supposed to solve our problems anyway?”
“Yeah, even if we turn the ugliest girl at school into a babe, she still wont want to go out with us. Let’s play some more Mashed,” Doug said picking up a control pad. For an excitable fellow like Barrel he continued to be calm, explaining his plan to two people that thought A) he was crazy and B) he might have other mental problems as well,
“Look guys, the other week we were talking about girls having power over us, withholding sex from us and stuff. Well, if this works one of us could become a babe and then we all could have all the sex we want!” I stared at Doug and we both put down our controllers. Barrel not only thought his plan was good, he thought it would actually work. Luckily, we were good friends because no one else in the world could have listened to that plan and not called the men in white coats.
Doug sidled up to Barrel, draped an arm over his massive shoulder and said, “The only problem is….”
‘The ONLY problem!’ I thought.
“who is the one we shoot?”
“Great! Now I have two crazy people in my house!” I exclaimed. But the other boys seemed to ignore me. They looked deep in thought. Too deep in thought for my liking.
“Well, since I was the one who bought it it’s not going to be me. So which one of you two wants to be a piece of ass?”
“NOT ME!” shouted Doug as fast as he could. They both looked at me. I stood up,
“What makes you think that I want to fuck you guys?” I said as I left for the kitchen to get some chips.
“Awww.. don’t be like that. Come back!” moaned Doug sarcastically.
“I’m just getting some chips!” I shouted. Angrily I tipped the bag of chips into a bowl and returned, “It’s not like the gun is going to work anyway!”
Doug picked up the gun and aimed it at me, “How do when know unless we try it?” His trigger finger poised, itching to fire some gender-bender ray at me then swung his aim to Barrel who looked quite scared for some one who was 6’6.
“Prepare yourself to get a vagina!” called Doug, doing his best (quite bad) Clint Eastwood.
Barrel tackled Doug, yanking the gun from his hands, “No! It’s mine. I’ll decide who gets pussy’ed! I want to do it!” The boys play-wrestled for a while, while I flicked around on TV for something to watch. “It’s not going to be me, because I bought the damn thing!” restated Barrel, “And that’s final!”
“Well, it can’t be me because I’ve got to go to my grandparents’ house on tomorrow!” was Doug’s reason.
“It can’t be me because…” I struggled for a reason, “It’s not going to work!”
“It might,” Barrel ventured, hope dripping from his voice, polluting the lounge room with dreams of banging a supermodel.
“We don’t know until we try, Scott!”
“Look, if it does work,” I said, “Then what happens?”
“Well, she has sex with us and then after a couple of days once we’ve become masters I shoot her again and she goes back to being a he,” Barrel said, another one of his amazing plans.
“So it works in reverse?” I asked as if it worked at all.
“I guess so,” Barrel shrugged.
“My parents expect me home tomorrow night, so it can’t be me,” stated Doug.
“Me too,” echoed Barrel.
“When are your parents coming home?”
“Next Saturday,” I mumbled. Tonight was Friday, which meant luckily my parents were gone all week! What a great way to start school holidays. We all stared at the gun sitting on the table. Doug picked it up. Looked at it. Looked at me.
And then Doug said those immortal words, “Then it’s agreed. We’ll shoot Scott.”
After throwing a minor tantrum, it was agreed that Barrel was to have the honour of pulling the trigger. I stood in the centre of the room, Doug had moved the coffee table just in case I fell after getting ‘shot’. I still didn’t believe it was going to work and voiced that opinion. “I’m going to love you sucking on this,” Doug grabbed his crotch, half teasingly.
I laughed and so did Barrel, “Yeah, it’ll freshen my breath, Tick-Tack Dick!” A common nickname that annoyed Doug.
“Any last requests?” asked Barrel, aiming right between my eyes.
“Just do it already!” I whined.
He pulled the trigger.
And bang or as the laser’s speakers would say “Pa-chow!” I was a girl.
Several factors told me I was now female- the way the boys’ eyes bulged and their jaws dropped, my blurry vision (my eyes were quite bad) snapped into perfect focus, the room grew smaller as I was now taller, parts of my torso strained the fabric of my fitted T and it definitely wasn’t my usual voice when I screamed long and loud.
For two guys expecting me to change into a hot babe they acted quite strange. Barrel, without sparing a second for though, ran from the room as fast as he could. He just left. I heard him fling open my front door and tear into the night. Seeing Barrel’s flee and unable able to formulate a plan of his own, Doug followed suit and belted outside.
And I was alone.
I stopped screaming and took a moment to calm myself. I had never expected this to happen so calming myself took a mite longer than you may think. Having two large boobs heave every time I took a deep breath wasn’t helping things either. It was only after I felt all feeling drain from my body did I feel calm enough to move. I did. Expressionless, I lumbered to the bathroom and looked in the mirror. Shit! Not only did it work, it worked amazingly. I have had a long relationship with my bathroom mirror and for as long as I have known it, it has never told a lie. It tells me when I have a pimple (often!), or when I need a haircut and it’s never been wrong. Oh how I wished that mirror wasn’t so damn trustworthy!
According to the mirror, I was a woman. Not a girl, not a 14-year-old female version of me but am honest to god, breathtakingly sexy woman. She didn’t have my crooked teeth (or my braces either! At least there was one good thing.), she didn’t have my frizzy and unmanageable hair, she didn’t resemble me one iota. She was a goddess. She was made to be worshipped. She was tits. She was ass. She was sex personified. She… was me?
I gingerly walked closer to the mirror, taking in my image. My face was angelic. Clear skin, cute button nose, full lips, deep blue eyes, cascading blonde locks. As an experiment I smiled, of course it was perfect. I now possessed a warm smile, with just a hint of pure sex in it to drive men wild. I turned and looked at my adorably cute ears that hid behind my long hair. I looked closer at my reflection: my ear had a tiny hole! Pierced! The gun thought of everything. I ran my fingers through my new hair; it felt more like silk than hair. It was long, just past my new shoulders and it was blonde. Of course it was. I was a walking textbook of female beauty.
The clothes that were a perfect fit 5 minutes ago were now all wrong for the job. My grey fitted T, which was doing a fine job on my scrawny 14-year-old male body, now fought hard against the rebellion of my new form. My new boobs struggled gallantly against the oppression of the cotton T. The boobs seemed to be winning the war, pulling the shirt taut and threatening to break out of their confines. The humble T-shirt was certainly losing the war further down. My body had grown a few inches in my transformation and my navel was now on prominent display. The whole ‘tummy’ region was firm. ‘I look decidedly trim,’ I thought, ‘as if I’m quite adept at doing sit ups.’
My boxer shorts didn’t seem to be fairing well either. The elastic was tight around my hips, if it was sitting higher around my slim waist I’m sure it would have been fine. I turned side on and saw the perfection that was my new derriere. It was wholly feminine and delightfully round, I was a bit of an ‘ass-man’ myself and if my penis was still present I would have had to hide a telltale erection. Sadly, looking at the flatness in my crotch it appeared I didn’t have my penis anymore, it would have enjoyed the examination of my new form. My ass trailed into two, long and gorgeous legs.
Delicately, I peeled my T-shirt off, wanting to see an actual girl’s naked breasts. This was not the wonderful first time I had envisioned. Firstly, the girl in question was way hotter than any girl I could have even wished to obtain and secondly, it was my breasts I was about to awkwardly fumble with. I didn’t take the shirt completely off, I hitched it above the tops of my boobs. They wobbled with my clumsy movement and I watched them in the mirror. I cupped one in one hand and tentative prodded my nipple with the other. I raised the one cupped in my dainty hand and dropped it, watching it merrily bounce back into place. For my next trick I squeezed them together and created a cleavage that would put all plastic surgeons and their silly notion that they can improve on nature to shame. I blew the mirror a kiss and giggled. Hearing my own laugh come out as a sexy giggle made me snap to my senses! What was I doing? Posing like a centrefold? I had more pressing issues! Such as- Why did I look like a centrefold?!?
My nipples said goodbye to the world as I returned them to their grey cotton prison. I marched to the lounge room once more, ignoring all the jiggling and wobbling and swinging in my new gait because I was on a mission. A quick search of the room informed me that the boys had taken the gun in their flight. I picked up my phone and prepared to call Barrel or Doug but decided against it. After my giggle scared me half to death what will my voice do? So I txted them, my long, exquisite nails getting in the way.
‘HEY SHITHEADS WHERE R U? CUM BACK ERE + BRING DA GUN BACK PLS!!!!!’
Perfect. Concise, authoritative and polite. It wasn’t long before my phone beeped back at me, alerting me to the response:
‘SRRY! WE PANIKED! WE RAN 4 AGES + TURNED ROUND ABOUT 5MINS AGO WERE NOT FAR NOW. SO SRRY! R U STILL GIRL?’
‘YES! BOOBS DON’T WASH OFF!’ was my reply. I had just finished thinking that the boys might never come back when the boys returned. Barrel sheepishly poked his head into the room to see me laying on my side on the couch, watching TV and trying to forget I had a vagina.
“Scott?” asked Barrel, Doug trailing behind him. I sat up, my body a flurry of arms, legs and hair. I felt the unmistakable feeling of boobs falling back into place.
“Well, welcome back, cockheads,” there was a tiny amount of satisfaction that my first sentence with my new voice contained the word ‘cockheads.’ Not much though, because the statement was strangely arousing coming from my new lilting, and undeniably sexy voice.
“Ummm…I guess the gun works?” said Doug, staring at my body. What part of my body I didn’t know. It could have been my pouty lips, my big blue eyes, my smooth, long legs, my golden hair, my flat crotch but if I was to take a guess I imagine it would be my bountiful bosom with my nipples attempting an escape through the T-shirt. Doug couldn’t look away, meanwhile Barrel was looking at anything but me.
“Yes,” I said calmly, “The gun does work. Now that we know that it does, shall we shoot me again and get me back to my old body?” I looked at Doug, it looked like he was about to protest or ask me for some sex but common sense quelled it. Barrel took the laser out of his pocket and aimed it at me.
“Stand back,” he commanded Doug, who leapt away as if Barrel held a ‘Cancer-ray’ in his giant hands. I clamped my eyes shut and awaited the joy of being back in my below-average, overly oily 14-year old male body once again.
“Pa-chow!” said the laser.
“Shit!” said Barrel.
My hands crept up my torso and grabbed a handful of boob.
“Fuck!” I said with my pretty voice.
Doug remained silent.
Obviously enough things had gone wrong this evening to warrant me losing my cool. I balled my elegant hands up and punched the couch with almost comically feminine rage, “You said it would change me back!”
“Maybe I missed!” Barrel said, approaching me and shooting me at point blank range.
‘Pa-chow!’ ‘Pa-chow!’ ‘Pa-chow!’
At least the gun didn’t make me more female, otherwise I would be Jessica Rabbit by now.
After shooting me 3 times right-between-the-eyes, Barrel put the gun down and once again looked at everything but me. “It wasn’t supposed to be like this. I’m sorry. Please don’t hate me. We’ll help you,” he muttered to himself. I sighed audibly and ran my finger through my hair. The room lay silent except for the Chevy Chase film that earlier tried to make me forget about my pussy situation. Doug looked confused. Barrel looked freaked out. I looked damn sexy.
“So, how do you feel, Scott?” asked Doug as he sat beside me on the couch.
“It doesn’t hurt,” I honestly replied, “but I would rather not be a girl.”
“You don’t look like a girl,” Barrel said. Doug and I stared at him, both of us wondering if Barrel would go on to say anything that stupid again. “I mean,” he began to clarify, “You look like a woman. You don’t look 14.” Doug and I were pleasantly surprised to realize he wasn’t as stupid as we thought. However that thought was short lived. “How old are you?”
“I’m still 14, you idiot! My body is just older.”
“You could pass for 22,” mused Doug while he looked at me up and down.
“I’d say 19,” joined in Barrel.
“I hadn’t thought about it,” I said.
“You’re definitely fully grown,” said Doug, not being as sly about my boobs as he thought he was. I defensively crossed my arms.
“You know, you are really pretty,” Barrel said sitting beside me. Even though I grew several inches in my transformation he still towered over me. I think he said I was pretty to alert me to my new look rather than as a compliment or a pick-up line.
“Thanks,” I smiled, “I know. When you guys ran I checked myself out in the mirror. What do you boys think, a 10?”
“Easily,” chuckled Barrel.
“More like a 20!” was Doug’s response, “Scott, you are easily the hottest girl I’ve ever seen in person. You’re a walking wet dream.” He was right.
The 14-year-old boy inside spoke up, “Yeah, I know. You should see my boobs!” In an effort to excite two already very excited boys, I stood up and stripped of my T-shirt letting my amazing breasts sway in the air. “Ta-da!” I exclaimed. My buddies sat stunned, their eyes threatening to leave their skulls. I eagerly ran my hands all over my rack again but this time with an audience. Pinching nipples, circling aureoles, cupping bosoms. I posed for their blinking eyes as if they were Playboy flashbulbs. It was more like a kid showing of his new bike to his friends than a woman seducing some gentlemen callers. It was too fast, fast is rarely sexy, and it was performed with child-like squeals instead of well-placed sexy moans. However, the boys also didn’t know the finer points of seduction and enjoyed the show just the same.
“How do they feel?” Barrel genuinely inquired.
I paused my extroverted performance and openly felt them. “It’s a little strange,” I murmured as I caressed the delicate orbs high on my chest, “They’re pretty soft, but sorta firm.”
“Are they real?” asked Barrel, with keen concentration on his face. I continued to touch my boobs, trying to feel for implants but not knowing what they would feel like.
“Why would the magic laser give him implants?” asked Doug, all the while I continued to grope myself.
“I don’t know! We don’t know how it works! Scott?”
“They feel real to me.”
“They’re pretty big.”
“Bigger than Julia’s sister!” boasted Doug, “I’d say about a D cup.”
“You think?” I said finally leaving ‘the twins’ alone.
“Yeah, easy! Or a double D!”
“Wow!” I said, 20 minutes ago I would have given my right leg to fondle a pair of double D’s, now I could do it all day. Finally, the conversation finally went where it was always destined to go. And unpredictably, it was Barrel who fulfilled the destiny.
“Scott, would you mind if I touched them?”
The original plan was to turn one of us into a sex-starved hottie and we could complication-free sex our way into sexual master craft. Now that the plan had become terrifyingly possible, I had to choose my decision carefully. There was no way in hell I was letting anyone near my *shudder* pussy. I hadn’t touched it. I hadn’t even looked at it yet. So anything leading toward a sexual encounter should be an automatic no-no. However, I could understand Barrel’s position. For the last few minutes he has had one of the hottest women in the world parade around him, groping, posing and generally enjoying her boobs very much. It is only natural that he wanted in. Was it right to withhold them from him? I’m pretty sure if he was in my position (and he could be if Doug gets a little trigger happy) he’d let me at least touch them.
“OK,” I said, cautiously walking towards him and kneeling so that I was within touching distance, “But please be gentle.”
“Can I…” began Doug.
“Go ahead,” I sighed. Doug scooted down the couch. I closed my eyes so I couldn’t tell you who first touched me. It was a tentative poke; quick and not sexual but scientific. A gentle hand followed it slowly stroking my left breast like it was a kitten. Another hand cupped my right, brushing past my nipple with my thumb. Having some one else touch my nipple gave me sort of an electric thrill. I had planned this sleepover to play video games and this was quite a different experience. I was enjoying this more than I would our 10,000th game of Halo 3. Fingers toyed with my left nipple, twisting it until it hurt. “Don’t play so rough, boys,” I purred and the twisted stopped, replaced with gentle rubbing. I tilted my head back and let the pleasure flow through me.
Doug whispered, “This is so fucking sweet,” and Barrel nervously giggled but I ignored them, relishing in the feeling of other people’s hands. I may have moaned. Strike that, I assuredly moaned.
Action on my right breast ceased for a second, returning in different form. Suction formed around my boob as a slippery tongue playfully flicked my nipple. I may have enjoyed it if I had known it was coming. But it startled me and I bolted my head up and flung my eyes open. All I saw was two guilty eyes staring up at me. I should have been angry but instead I involuntarily giggled and asked politely, “What do you think your doing?” Doug unable to talk with such a mouthful just shrugged. “Can I have my breast back, thank you very much?” I felt Doug release and I stood up, wiping up the spittle with Doug’s jacket.
“Great! Way to ruin that nice little thing!” whined Barrel hitting Doug about the head as I pulled on my T-shirt.
“It was worth it,” said Doug lying back on the couch with a huge grin on his face.
“Well, now you’ve both felt a boob. You can cross that off you dream list,” I sat on a rocking chair in front on the boys, coyly rocking back and forward.
“Did you like it?” asked Barrel, “I mean, did it feel nice?”
“You were both a little rough. When you do it with a real girl…”
“You are a real girl.”
“When you do it with a girl other than me be a little more gentle. But yes, it felt good some of the time.”
“Be more gentle,” repeated Barrel as if he was taking notes in his head.
“Did you orgasm?” Doug asked, leaning forward. I thought about it, continuing to rock back and forward. “No, I don’t think so. I mean, it did feel good but not that good.”
“But you moaned.”
“I don’t think a woman can orgasm just by guys playing with her tits,” said Barrel sounding unsure of his own opinion. I thought about it, while it did feel good I didn’t feel the ‘earth move’ and told the boys the same.
“Well, there’s only one way to find out,” said Doug.
“And what’s that?” I asked.
“Let one of us have sex with you until you have a proper orgasm.” I stopped rocking. That plan wasn’t going to happen. I enjoyed the little party game of ‘Squeeze-The-Hooters’ but there was no way I was going to play ‘Hide-The-Salami’ especially since I knew where you were supposed to hide it.
Unconsciously, I crossed my legs. “No way! You’re not tricking me with that perverted plan,” I hissed pointing a slender finger at Doug.
He laughed and gave up, “At least it was worth a try!”
The mood in the room felt totally schizophrenic. It could go from jovial to sensual to deeply serious. It was such a crazy situation that all of these moods were right and nobody could predict what would happen next. I was surprisingly not hating this experience as much as I thought I would, or probably should. I liked teaching the boys, I was like their mentor. I enjoyed teaching them things that they would never figure out on their own, even though I didn’t know most of the answers myself. As a boy, I rarely had any expertise, letting Doug dictate the answers and most of the questions as we talked. He was the leader. But now he was a little boy, begging me, a woman, for answers to life’s great mysteries. I stretched, letting all the crazy feelings from my body race to my head. Curiosity got the better of me so I hatched a plan and stood up.
“Who wants to see me naked?” I cheered with all the enthusiasm of a cheerleader. The boys couldn’t believe their ears and cheered as if they were at a strip club.
“Really?” asked Barrel, “You would do that for us?” I arched my back, feeling two sets of eyes scour my impressive chest. My friends were in the palm of my hands and I enjoyed the control I had over them.
“Why not?” I asked shedding my t-shirt and throwing it at him like the strippers in movies, “I’ve got to get nude sometime soon.” I hooked my thumbs in the elastic of my boxer shorts, counted down from 3 to 1 and dropped them to the ground.
There was a slight breeze and as it whooshed past and I felt between my legs. My buddies leaned forward to get a closer look. I slowly spun around, showing off all 360 degrees of my magnificent body. “So sexy,” whispered Doug to himself. I decided I wanted to take a look at myself. Considering how petrified I was of my ‘pussy’, it wasn’t that much to look at. Looking down, between my breasts, all I could see was a small tuft of hair. Just a sparse patch of blonde curly hair. That didn’t seem to be too worrying. What was I so scared about? “I guess you’re a natural blonde.”
I blushed, nervously biting my bottom lip, “I guess so.”
“There’s not much hair down there,” Barrel said.
“It’s what girls call a ‘landing strip’,” Doug informed us.
“Why do you think it’s called that?” I asked, running a finger up ‘the strip’.
“Because it shows guys where to land,” Doug unnecessarily pointed to my genitals.
I was sick of being the student. It was time to take charge of the class again and teach them something. “I’m going to see if I can have an orgasm,” I announced while my hands hungrily slid down my body.
“How?” said Barrel as he sub-consciously rubbed his own genitals.
“I don’t know. I’m just going to play around down there, I guess, until something happens.”
“Can we watch, please?”
“Of course, gentleman. What’s mine is yours!”
I hadn’t thought doing it alone. I’m sure most girls’ first experience with masturbation is done alone, clumsily under blankets feeling aroused and ashamed at the same time. Very few would be for the entertainment and education of her male best friends. But I sure wasn’t an average girl. I lay down on the carpet and began general rubbing, totally unsure of myself. I spread my legs, giving the boys a good view. With no expertise whatsoever, I let instinct take over. General feelings of pleasure washed over me as my pussy became moist. My hand flew up to my chest to play with my nipples. The nipples was hard and felt infinitely more sensitive compare to my dull, tiny male nipples. Unlike the boys I was gentle, softly tweaking and increasing my pleasure.
Barrel, unable to stem his curiosity once more, asked me, “Does it feel good?”
“Mmm… yeah,” was the moan that flowed from my lips, “It’s so good.” One of my delicate fingers entered my pussy, which was now quite. Although my eyes were closed, I could hear the unmistakeably sound of penises being stroked intensely. The boys were enjoying my show but nowhere as much as I was. “Have you found the clitoris?” Doug inquired.
“I’m not sure,” I said between moans.
“You’re supposed to rub it, I think. It makes things feel better,” was Doug’s uneducated suggestion. I ignored him and continued to do what seemed to work.
Moans turned into yelps of passion. My breaths became staggered. The yelps ebbed and were replaced by my girly voice chanting, “Oh god! Oh god!” I think one of my friends asked if anything was wrong but I was too deep in my own pleasure to respond. My finger continued to work my pussy, making squelchy sounds as it went. My right hand passionately rubbed my right boob. “Oh god!” melted into just plain “Ooooohhh!” Doug and Barrel, enjoying a show not afforded to many teenagers, excitedly worked their penises. How jealous they must have been of me, sweat glinting off my perfectly formed body, my telling moans revealing to them a pleasure they would never know in their current bodies.
By this time I had clearly answered that the tiny moan of pleasure I released while amateurs rubbed my boobs was not an orgasm. This heavenly event I was on the cusp of was the real deal. My entire body tingled with bliss. I thrust my finger faster and it pushed me over the edge. I squealed in delight, letting a wave of ecstasy flow over me. I stretched out, enjoying the aftermath and joyously caressing my boobs. My left breast getting coated in the juices that covered my finger. The whole experience left me breathless and I pictured feeling like this all the time as I coyly writhed on the carpet. “Wow,” I breathily moaned, breaking the silence and allowing the boys to talk once more.
“How was that?” said Barrel, also sounding exhausted. I rolled on my side to look at my friends. They were a sorry sight. While I looked completely resplendent, basking in my post-orgasm glow, they looked dishevelled as the clutched their shrinking dicks, their bellies drizzled in semen.
“That… was fucking fun!” I said, closing my eyes and soaking in what was left.
“It looked fun,” joked Doug, “Was it better than jacking off?”
“Yeah,” I sat up excitedly, the 14-year-old in me kicking off, “Like a thousand fucking times better. It lasted for ages. It’s like all over my body. I felt it in my arms, and legs and boobs and pussy. It’s not just in my cock.”
“You don’t have a cock,” helped Barrel.
“I know that.”
“I could give you one,” insinuated Doug winking as his penis began to rise again.
“Umm… no thanks,” I said, flipping him the bird.
“You made a little bit of a mess,” Barrel said and pointed to a small wet spot on the carpet.
I blushed, “Yeah, it was a bit wetter than I thought it was going to be.” I stood up to distance myself from the mark on the carpet.
“It smells a bit too.” I winced as Barrel pointed out the musky aroma in the air. “I mean it smells yummy,” Barrel corrected himself. Doug joined in, “It does smell pretty good.” I sniffed the air, I’m glad the boys liked my smell.
I was strangely proud, and to illustrate how proud I was I took my finger that still was covered in my pussy juices and sensually placed it in my mouth and wrapped my plump lips around it. “Mmm…” was my reaction, “It tastes a little weird.”
Considering how much I had allowed the boys to do that night I shouldn’t have been stunned at the next question. “Can I have a taste?” It was Barrel and he seemed genuinely interested in my taste. Since today was all about education I agreed, wetting my finger in the well of my vagina. He opened his mouth and I inserted my finger, his tongue removing the unusual flavour from my finger. He winced slightly, “It tastes like sweet fish.” I gestured towards Doug offering a free taste test.
“Are you sure?”
“Speaking of food, who’s hungry?” I said, throwing a box of tissues at the boys so that they could clean themselves up.
“Now that you mention it, I’m starving!”
“Dad left me some money to buy food this week. Pizza good?”
“Sounds good to me!”
“How about one large meat-lovers and one large supreme?” I suggested, my new gender not distracting me at all. Doug and Barrel agreed with my choices and I dialled our local pizza place.
“Hi,” I said, suddenly aware of my sweet voice, “I…I’d umm like to place an order.”
“Sure, miss” ‘Miss’? I wasn’t ready for that, “What would you like?” I ordered trying unsuccessfully to not sound sexy. Even though there is nothing intrinsically sexy about ordering pizza, when I talked about it, it sounded like a list of tawdry things I’d like to do with him. I guess it didn’t help I was naked and coming down off the best orgasm I’ve ever had in my life. I told him the address and he said they would be there in 20 minutes.
“Scott, what are you going to do?”
“I’m just going to get a drink,” I called over my shapely shoulder, knowing the boys were definitely checking out my butt as I knowingly sashayed out of the room. In hindsight it was probably too exaggerated to be actually sexy but I hoped they enjoyed the little show I was putting on just the same.
“No,” said Barrel, “What are you going to do now?” With one question Barrel sucked all of the sexiness and silliness out of the air and replaced it with foggy seriousness. I returned, three Cokes in hand.
“Ummm… I’m not sure. I can’t exactly stay here. My parents…” I trailed off, no longer caring if my walking entertained the boys. “You’ll have to find a place of your own,” mused Barrel.
“Yeah and get a job, or find a way back into school,” added Doug, finally turning his mind off sex.
Worry suddenly enveloped me, “My parents will think I’m dead or kidnapped or something.”
“It’s ok, we’ll just say you ran away,” was Barrel’s effort to cheer me up.
“I can’t get a job. I don’t know anything, I’m just a kid,” a moaned, tears beginning to form within my radiant blue eyes.
“Scott, look at you! You can be anything you want! You’re lucky. You could be a fucking super model!” said Doug draping an arm around me and leading me to the couch.
“Or an actress!” was Barrel’s suggestion.
“Or a porn star,” said Doug more earnest than anyone else in history recommending porn star as an occupation. That made me laugh.
Doug tried to cheer me up, “We’ve got all of high school to finish before we can start our real life. You’re so lucky, dude. You got a free pass. You’re past High School. You can get a job, get your own bachelor pad, party every night! No parents, no homework, no problems. Your life is going to be awesome. I’m actually jealous of you.”
“Well… you could join me?”
“I could shoot both of you guys and we start a new life together. Three sexy women! Then you could really see what an orgasm feels like!” I didn’t know what I expected, but this was an honest suggestion. It would be so much less of a struggle if there were three of us.
Doug looked away from me, “No sorry Scott. I can’t. I like being a guy.”
“Don’t you think I liked being male?!” I said, my body shaking and thus my long hair and boobs shook.
“I’m sure you did. But you’re a woman now and it doesn’t look like we can change you back.”
“How about you, Barrel?” I asked my other friend, who sat very quietly.
“I can’t. My Mom would go crazy,” Barrel frowned, not daring to look me in the eyes, “But I’m going to help you. My stepbrother makes fake I.Ds and I know where my folks hide like a thousand bucks.”
“And I’ve got $500 that I’ve saved.”
“I’ll sell my X-Box, Scott. Just so you can have money,” that was quite a sweet gesture, because other than Doug and me, the only other thing in Barrel’s life was his X-Box. I felt sad yet thoroughly helped. Although these boys weren’t going to give up their penises (and who could blame them?), I know they would help me. They weren’t trying to hurt me when they shot me and they planned to make up for their mistake any way they could.
I let our a sob, “Thanks guys.” A naked woman then hugged two teenage boys who also cried. My hooters squashed against their chest. Then, just as quickly as I had started crying I stopped crying. “Wow, I’m going to get my own place!” I said excitedly forgetting about bills and rent and the fact I had no money to my name, let alone an actual name, “Will you come and visit me?”
“Everyday!” smiled Barrel.
“Especially if we can play with these,” Doug added playfully drumming on my boobs, watching them jiggle. I giggled watching them jiggle.
“Hey Scott,” Barrel said staring at my bouncing breasts, the largest breasts a boy called Scott ever had, “Are you a lesbian?” I pursed my lips and thought about it, while sex was surely the theme of the day I hadn’t given much thought much about my sexuality.
“I’m not sure,” I admitted.
“Well, quick test. Are you attracted to us?” said Doug gesturing to his short, chubby and adolescent physique.
“No,” I snorted, “You’re my friends, though.” My cheap to make them feel better seemed to have worked. Doug pondered his next question.
Barrel spoke up, “Plus if every girl who wasn’t attracted to us was a lesbian than planet earth would be in a shitload trouble!” I laughed long and loud while Doug just looked annoyed.
“You weren’t so hot a few hours ago!” sneered Doug.
“Well, that was then and this is now,” I said flicking my hair like a goddess.
“Are you a lesbian or not?” childishly demanded Doug. I thought hard and try to force and answer out of my head. It was useless, this was all too weird to get any concrete answers out of my muddled head.
“I don’t know,” I sighed.
“What did you think about when you were playing with yourself?” Doug would not stop his interrogation. “I was just enjoying my body.”
“So there were no images in your mind?”
“I don’t remember,” I confessed, “It was all a blur. Why is it important?”
“I don’t know, I guess I just wanted to know. You weren’t a gay before you got shot, were you?”
“No!” I squealed, offended at the term ‘a gay’.
“Well, you’re probably not gay now,” he concluded with the voice he reserved for all his worldly knowledge. Knowing now that certainly didn’t know the answer to that question made me question all his other seemingly knowledgeable answers. The ones he would say, confidently with a smirk on his face. This time his smirked faded as Barrel took the floor.
“But if she was attracted to girls before maybe that hasn’t changed,” ventured Barrel. I felt uneasy about referring to me as ‘she’ but Barrel always did call a spade a spade.
“Maybe I’m bi!” I cheekily suggested. I was about to describe some explicit scenarios that I could involve myself in, when the doorbell rang. “The Pizzas!” I shrieked, remembering how hungry I was. I jumped up, feeling my boobs bounce along with me at their own pace and grabbed enough money from the can on the bookcase where my dad had left me the money. I suddenly realised I was utterly, utterly naked, “One of you guys answer the door, I can’t have anyone seeing me like this!”
“No,” Doug audaciously objected, “You answer the door. It’ll be funny!” he and Barrel sniggered like the teens they are.
“The pizza guy will have a heart attack!” squeaked Barrel.
A sickening combination of the pride of my majestic new body and my inability to turn down a dare made me giggle alongside them. “OK, OK… sshhh! I’ll do it.” The boys followed me into the hall and hid in the alcove near the front door. I gulped, hard, steadied myself and opened the door.
“Hi, I’ve got 2 lar…oh!,” the Pizza guy stared at my boobs, pussy, legs and face in that order. Within the space of two seconds the Pizza guy had taken in all he needed to for a lifetime of sexual fantasies.
I demurely nibbled my bottom lip and played with my hair. “Sorry,” I whimpered in my best little girl voice, “I just got out of the shower.” That wasn’t true, my hair wasn’t wet and the glistening nature of my body was due to some pretty heavy petting but he didn’t seem to notice.
“Oh. OK,” said the Pizza guy and casually as he could muster he continued, “That’s cool. 2 pizzas, that’s 18 bucks.” I handed him the exact change as I was going to need all the money I could get if I was about to move out of my house with no job. I was not shocked at all to see him faun all over me. As soon as the mirror greeted me I knew I had a power given to beautiful women. He, like most men, would be powerless against my looks, my voice and especially a little bit of flirting. My effect on him was expected. However, his effect on me was not.
The Pizza guy appeared to be the same age as I appeared to be. He had a nice tan complexion and his eyes were piercingly brown. His face looked like it was chiselled out of stone and I imagined that under his pizza delivery shirt his chest was firm and manly. As I took the pizza, I accidentally glanced at his pants, a telltale tenting in his crotch told me that he was enjoying what he saw. “Sorry,” I apologised again, “I don’t have enough money for a tip.”
His eyes took another quick survey, drinking in all my womanly curves. His face erupted in a gorgeous smile, “Don’t worry about it at all. You’ve made my day.” I winked at him and he trundled off into the night, with a boner and a story to tell. I watched his manly buttocks until I closed the door, holding the warm pizza box in my hands.
I turned around and my buddies burst out laughing. I’d forgotten they were there and their boisterous hooting startled me. “That was hilarious!” cried Doug.
“He’ll be talking about that for years and years!” said Barrel slapping his leg in merriment.
“I swear dudes, she was totally naked!” Doug said, doing his best imitation of the pizza guy. Since we were teenager boys we loved playing pranks, but we had never had the opportunity to use a naked girl in our pranks. ‘It looks like the body has yet another use,’ I thought, adding pranks to my list.
I pulled on the T-shirt before hoeing into the food. I was proud of my full, round, breasts and didn’t want melted cheese or toppings dirtying them up. “I figured out something when I was talking to the pizza guy,” I said quietly, almost to myself.
“Yeah, what’s that?” I heard Doug say between bites of his first slice.
I nervously looked around the room before I decided I might as well tell them, “I’m pretty sure I’m not a lesbian.”
“What?” The chewing stopped and mouths full of pizza awaited my explanation. I quickly explored my feelings one more time before speaking, “He was cute. I liked looking at him. And these,” I said pointing to my nipples, who stood proud atop of each boob, “felt hard.” I’m not sure why I announced it, but since I was sharing all sorts of private things (secrets, knockers, juices, etc) I felt it was in order. “It was like a little switch went off in my head and I pictured him naked…and… and I liked it. I’m not sure if I’m attracted to girls though, we’ll have to see.” I secretly hoped I was into girls because I remembered how much I used to enjoy watching them as boy.
“That’s good to know,” Barrel said kindly, “Are you enjoying being a girl?”
“Some of it can be fun. The orgasm I had was crazy, I’d like to do that again. But I feel so weird. I’m taller and my butt sticks out and my boobs stick out and my hair is real long and this voice is weird and I miss my penis. I guess I can live like this but if I could I would so change back in a second.”
“I’ll keep my eye open on e-bay for a girl to guy gun,” said Barrel thoughtfully. The rest of the meal was listing off girls that I was now hotter than. According to my pals, I was now hotter than all the girls at my school. I owned a better ass than Carmen Electra. My body was hotter than Jessica Alba’s. My face was cuter than the cheerleader off ‘Heroes’. There was no-one I was coming 2nd to.
“Scott’s hooters are way better than Heidi Klum’s,” theorised Doug, “I think yours are bigger than Heidi’s, they are definitely firmer. What do you think, Scott?”
“I’m just happy to be nominated,” I joked, “But seriously my tits crush hers!” I cupped my award winners and again playfully jiggled them.
“Scott, your tits are amazing!” Barrel said, clumsily trying to compliment me. But it sounded weird, all this talk of Jessicas, Pamelas, Heidis and Mandys made my name sound ridiculous.
“I need a new name…”
“Yeah, you do don’t you?”
“What’s your stripper name?” asked Doug.
“You know,” he explained, “Where you take the name of your first pet and the name of the first street you lived on.”
“You want me to change my name to ‘Rex Westbrook’?” We all laughed. Not many people have to choose their own name, mainly parents took on that duty. I liked the job my parents had done ‘Scott’ was a simple, easy name. It wasn’t too show-offy and it suited me fine. What it didn’t suit was the person I had become, I hadn’t met any girls called Scott and while there might be some out there I was not going to be one of them. A beautiful girl deserves a beautiful name.
“Well, Westbrook will do but you need a better first name.”
Barrel, partially to himself, started sounding off name, “Lisa, Sarah, Kate, Krystal….”
He continued his list that could potentially go for hours. Doug chipped in, “You kinda sorta look like a sexier version of Heather Graham, why not Heather?” I rolled ‘Heather’ around in my head for awhile.
“Nah. I think I like Jennifer,” I decided, “Jennifer Westbrook.” Saying it out loud made it seem real.
“I like it,” confessed Doug.
“We can call you Jenny,” smiled Barrel.
“You can call me Scott,” I replied, adding “Jenny in public.”
Doug waited a moment, stuck out his hand and said, “Pleasure to meet you, Jenny.” I took his clammy hand and gently shook it. Barrel did one better, he extended his hand, said “It’s a pleasure to me you, Jenny,” and kissed my hand like gentleman in movies.
Speaking of movies, that’s what we did next. Sat down and watched movies. For a few hours it was an excuse to ignore the real world. Although, I suddenly thought of problems as we watched the movies. Luckily the boys helped me with answers:
Q: How can I get some clothes?
A: We’ll go and buy me some stuff tomorrow.
Q: What will I tell my parents?
A: I’ll write a note to say I ran away and will keep sending them letters to say I’m fine.
Q: Where can I work?
A: Barrel’s uncle hires backpackers to pick fruit at his farm without checking ID. All cash in hand stuff. Barrel’s stepbrother can fake up some ID and maybe even a passport.
Q: Where can I stay?
A: I’ll stay at the house until the end of the week and by then we’ll have something sorted.
Q: Am I going to go to a bar?
A: You bet your life I am.
I was happy for all the help I got. I would occasionally suggest that they join me in womanhood but they would decline. During the movies’ sexy moments I would nonchalantly play with my boobs, moaning and trying to convince them to join me as a girl. But no matter how attractive I made it seem they weren’t ready to be ‘Pa-chowed’. I would have liked for at least one of them to join me. As a boy, Barrel quite often was a moron. But as a girl he could be seen as a bimbo and most guys think there is nothing wrong at all with a sexy bimbo. My future would seem a lot less scary if I had some one else experiencing the same thing as I was. I looked over at the pathetic looking gun once or twice, it was just sitting on the coffee table. Once I brushed past my pussy with my hand and wondered if I should run over to it and convert my friends into fellow babes. They might have enjoyed it. But my conscious got the better of me and I wasn’t about to punish them for tiny mistakes.
Before the second movie started I went to the toilet. Embarrassed at not being sure quite how to do it I sat down and felt a familiar feeling coming out of an unfamiliar spot. I gently dabbed a piece of toilet paper between my legs and left. It wasn’t that different and compared to the orgasm and suddenly finding men attractive it rated quite low on the weird meter. The boys were poised with questions when I returned. “So, JENNY?” Doug said, emphasizing my new name, “How was that?”
“How was what, DOUGLAS?” He suddenly became a little shy,
“You know…umm… going to the toilet. Did it feel different?”
“Not really,” I responded honestly, “I mean, I have to sit down but it still feels the same.”
“So, it doesn’t feel much different,” said Barrel, trailing off as if he was adding it to a mental list of his.
“Thank Christ that pissing feels normal. I mean, so much has changed that I’d probably freak out if pissing went all weird.”
Doug then said something I didn’t want to hear at the point in time, in fact there was no good time to tell this to a 14-year old boy, “You know that you’ll probably be on the rag within a month.”
“What?” I gasped, covering my pussy as if trying to plug the inevitable flow of womanhood. I seriously hadn’t thought about that. I’d been enjoying the fun bags and the orgasm I hadn’t thought that I may have a period.
“Yeah, you seem to be a real girl and real girls bleed once a month.” I sat down on the couch, deflated. Of course I would have a period. Something to look forward to, I guess. I pouted, but instead of looking devastated I looked comically sulky.
“But look at it this way, you can have those amazing orgasms every other day a month and then for 1 day you have your period,” said Barrel, who always knew how to see the silver lining.
“Girls don’t have a period for just one day!” interjected Doug to bring me down once more, “It lasts ages!”
“Uggh!" I groaned, "How long?”
“I don’t know, a few days!” Doug shrugged.
“Great!” I moaned, “And I can get pregnant.”
“Not if we use a condom,” said Doug. I didn’t want to disappoint the little scamp so I left the use of ‘we’ alone. There was no way I was letting Doug touch me with his cock, not in a million years, but I didn’t want to spoil his dreams as he slept that night. Barrel’s massive girth also put me off sexual thoughts of him. Plus they were just kids and a body like mine deserves to be taken care of by a real man.
We all got into our sleeping bags as it was late and we’d probably fall asleep before the second movie was done. I stripped off my T-shirt again so I was totally naked. Despite being naked most of the night, I still made a bit of a show undressing. “Scott, you should spank yourself! Give us something to dream about!” Doug said.
“OK!” I said, spanking my tight ass a few time much to the delight of my friends. I was amazed when no one asked if they could spank me too, but I guess we were all a little tired.
“That’s given me such a boner!”
“Deal with that yourself. I only make boners, I don’t take care of them!”
I squirmed into my sleeping bag. “So, fellas, what’s the plan for tomorrow? Are we going to have a crazy day?” I asked the boys either side of me.
“I guess we’ll go shopping tomorrow and get you some essentials,” said Doug, “but I’m going to have to leave after lunch because I visiting my grandparents out of town tomorrow night and Mom would be pissed if I was late getting home. Sorry Scott.”
“I’ll stay until after lunch too. But I’ll be grounded all holidays if I stay the night again. Sorry Scott to leave by yourself on your first full day as a girl.”
“It’s OK,” I said, rolling onto my back in an effort to get comfortable, “You boys know what? I was planning on going to a bar tomorrow night anyway, so you couldn’t come with me anyway.”
OK, it was a spur of the moment plan but I wasn’t about to spend my first full night as a woman alone. And going to a bar should be an awesome amount of fun.
“Really? An actual bar?”
“That would be awesome! You’ll be able to get drunk and everything! Do you think you’ll get drunk, Scott?”
“That’s the aim,” I said confidently, “I wanna look real hot so we’re going to have to get some sexy stuff.”
“Why, Jenny? Do you want to fuck some guy?” groaned Doug in a ‘we were here first’ tone.
“Eiwww! No! It’s just what people do. Get all dressed up. And please call me Scott.” I rolled over again, trying to find an angle where my boobs weren’t getting in the way.
“Maybe I’ll kiss some guy… or a girl!” I dreamed aloud.
“You’ll text us if you do, yeah?” Doug asked excitedly, “With all the details. Especially if it’s a girl?”
“I promise,” I replied rolling again, “Ow! Fucking tits!”
“Are they getting in the way?” asked Barrel.
“Yeah, I can’t get comfortable,” I said wriggling in my sleeping bag.
“Goodnight guys,” said Doug wearily.
“Get up, dickhead!” Doug poked me, “Just because you’re a girl doesn’t mean you get to sleep in.”
So it wasn’t a dream. I ran my tongue over my teeth, no braces. I ran my hand across my pelvis, a small soft tuft of hair. I opened my eyes, blonde strands of hair hiding some of the world behind them. “Shit! I’m still a girl,” I wailed. It would have been a pleasant dream or a wonderful evening if I had awoke as my pimply original self, but now all the problems were here to greet me this morning. No job, no clothes, nowhere to live.
“Get up and have a shower, Barrel will be back soon.”
“Where did Barrel go?”
“He went to sell his X-Box and pick up my money box so we can buy you some silly dresses!”
“I’m not getting a dress!” In my half awake state I was telling the truth, despite the womanly body I now possessed there was no way I was getting into a dress.
“Alright whatever, bras and shit. Hurry up and get ready.”
I emerged from my sleeping bag, like I was emerging from a cocoon. My feminine curves slinking out of my very warm confines, I slept naked so it was it was extra ready for a shower. Someone had laid out my longest pair of elastic tracksuit pants and a red polo shirt that my dad sometimes wears. I guess this was my ‘outfit’ to the mall and that was fine to me. I wouldn’t be the most fashionable girl at the mall. But I would certainly be the hottest. The water began to trickle down and I adjusted the temperature until it was just right before I got in. I promised myself I was here only to clean and that’s what I did, despite a few extra seconds I spent gently scrubbing my nipples with a loofah, or the special attention I paid to the soft folds of my vagina. All in all, I think it was quite a diligent effort from me, considering how sensitive my new body was. My long hair felt quite damp and a simple towelling didn’t fix the problem much. Luckily my mother had left her hair dryer out, so I dried my hair, all the while brushing it. I liked brushing my hair and I loved the image in the mirror of the sexy naked girl, brushing her long blonde locks, sitting on the countertop.
Doug knocked on the door, alerting me that I wasn’t the only person in the entire world. My hair-brushing arm covered my nipples while I crossed my legs hiding my other ‘pink bits’. “Come in,” I called and he did.
“Hurry up,” he whinged, “Wow, Scott. You are so fucking hot!”
“I know! Tonight is going to be so fun!”
“I wish I could come.”
“You could,” I purred, shaking my hair which was finally dry.
“How?” I aimed the blow dryer at him and made a noise like the girl gun,
“Oh, no thanks I’ll wait ‘til I’m 21!”
“You’re a pussy!”
“No, I’m not,” I giggled, pointing down between my legs “I’ve just got one!”
“Just get dressed! I’ve ordered a taxi for us to take to the mall. It’ll be here in a few minutes.”
“He’s already here, waiting for you to finish with your stupid hair!”
I pulled on my father’s top, tugging it to get over my hooters. It wasn’t an amazing fit, but I still managed to look amazing in it. Same story with the pants. I studied myself in the mirror. I looked like a college girl on her washing day, all her good clothes are in the wash and she’s left wearing what one of her ex-boyfriends left. I didn’t look like a caricature to womanhood, squeezed into 14-year old boy’s clothes as I thought I might. I would have to be a little wary that my nipples that poked through my top didn’t become too distracting.
“Hi Jenny,” said Barrel nervously clutching a think wad of money, “Just practising for out big trip out. How did you sleep?” I walked in the hall and sat down near the front door.
“Pretty good, considering.”
“Did your boobs get comfortable?” Barrel said, not noticing I caught him glancing at my nipples. This ‘boob talk’ was a little confronting so early in the morning (OK it was 11.30, but I had only been awake since 11). But considering last night he was massaging them with his own hands I guess it wasn’t out of order.
“Yeah, it’s a little weird but I’m getting used to them.”
“I don’t know if I could ever get used to them, I mean they’re so big and out there. They must get in the way all the time.”
“Yeah, they do! I mean, most girls’ breasts aren’t as big as these,” I said, quite proud of an achievement I did nothing to obtain, “But I guess girls wonder how we walk around with cocks.”
“Yeah, I guess so. Do you miss your cock?”
“Oh yeah! Tons. Sometimes I squeeze my thighs together and it feels so weird having nothing there.”
A car horn honked and called out to Doug. He ran down the hall screaming, “Let’s go shopping ladies!” in his stereotypical gay voice. We laughed as we got into the car. Since I was the girl, and appeared to be the oldest (Despite being the youngest by three months) I sat in the front. I pulled my seatbelt down, and they sat unpleasantly between my boobs. The cab driver was a woman and I felt so proud that I was easily 30 times hotter than her. She was fat and old and her face was painted with a permanent frown. She said next to nothing all the way to the mall.
Around noon on Saturdays at the mall is an interested time. Families who work all week all go shopping Saturday morning. They drag their kids around store-to-store buying things kids are not interested in at all, like garden furniture or ‘Church clothes’. By noon the kids get a little bored, a little tetchy and very hungry. More children are more annoying at noon on a Saturday than at any other time of the week. That’s why you always see one type of parent either being very nice to their cranky kids, by buying them candy, taking them to a talking animal film at the Megaplex or leaving the mall altogether. The second set of parents do not kowtow to their children. They will drag their children, kicking and screaming, to another store scolding their kids to keep quiet. The parents have had enough and are not putting up with it anymore. They are the more fun of the two groups to watch.
Meanwhile, the teenagers are just starting to arrive. Noon is the earliest most parents will drop their younger teens off, after they’ve mowed the lawn or finished their homework. The older teens arrive at the mall at noon to escape their hangovers. It’s at the weekend when nervous teens meet up with each other for their first dates, known as ‘hangin’ out’ and the mall is the perfect place to break up with your boyfriend/girlfriend, a neutral public place, nice and safe. Most teens will spend a lot of time at the mall but not a lot of money. Others have rich parents or work hard during the week, so that they can splurge on the weekend.
I was here to get some clothes. I confidently strolled into the mall, letting my hips swing their natural gait. I slowed slightly, not impressed with the amount of bouncing my bust was doing. The boys followed behind me, like I was their aunt taking them out for a day at the mall, my treat! But, in fact, they were paying for everything. “Where should I go first?” I ask the boys genuinely.
Without any collaboration, they both said the same thing, “Bras.”
I guess I had to laugh. Since I was completely barefoot, I would have assumed one of them would have said ‘shoes’. “Boys will be boys,” I joked.
“Not all of us!” Doug added. I punched him hard and told him to behave as we entered the lingerie store. A lingerie store a room filled wall-to-wall with all things girly. Bras, panties, G-strings, nighties, teddies and other girly things so girly that I don’t know their names lined up ready to be bought by girly girls.
“Hi, my name is Alice. Can I help you?” I cleared my throat.
I had only ever worked backstage during the school’s theatre performances so being thrust into the lead role was very daunting. I cleared my throat, “Hi, I’m Jenny. I need some bras and panties.” Not bad for a first performance, I was ready to collect my Oscar.
“Oh cool,” said Alice in her bubbly salesperson way, “What types of things were you after?”
I wasn’t ready for a second question, I hadn’t thought far enough. “Umm… Just every-day stuff, you know, a couple pairs of those. Something that looks nice because I’m going to a bar tonight, you know.”
“OK, then I can help you with that. What size are you?”
Ah ha! I was ready for that question. “Well,” I began, “I’ve just lost a whole lot of weight and I also got breast implants a week ago, you know. So, I’m not sure what size I am any more!” I smiled, giving her the ‘aren’t I foolish’ look. That was a good answer.
She took me to one side of the store where she laid the tape measure around my body in different places, reading of numbers as she went. The boys nervously walked around the store, sometimes hanging around me, other times keeping their distance. When Alice had finished she read me my sizes, noting that I was a double D. “I told you so,” Doug gloated, which must have seemed strange to Alice. I shot him my evil eyes and told him and Barrel to go get some everyday stuff while me and Alice picked out the special set.
I smiled nervously at Alice, “We’re in a little bit of a hurry.”
Alice showed me around some of the sexier stuff. “What do you plan on wearing tonight?” she asked, not sure whether I would know the answer.
“I’m not sure, maybe some jeans and a top thing. Something that shows a lot of boob.”
“Will it be like a halter top or a tube top?”
“Yeah..” I agreed, not knowing exactly what either of them were. She did her best to hide a sigh.
“Just go to the dressing room and I’ll bring you a few options,” she said, pointing be towards the back of the shop. On the way there, I bumped into my partners in crime.
“How’s it going, Jenny?” asked Barrel, while thumbing through some cute red pairs of silk panties.
“Good,” I lied, “I think I’m passing. I’m just off the change rooms.” Doug handed my 4 or 5 bras.
“Well, we’ve got some bras for to try on. They’ve all got matching panties.”
“Can I try on the panties too?” Doug pointed to a sign,
“You’re not supposed to try the panties on, but they’re your size.”
I unleashed ‘the twins’ they were happy to get out and jiggled with anticipation as I fumbled with the first bra. My first bra. It was white, it was soft material with wire in it. I fiddled with it awhile before I finally got it on. It felt like two hands were gently cupping them. I jumped up and down on the spot and while it didn’t stop the bounding around it certainly ‘controlled’ it. Looking in the mirror, there was something terrifying about it all. I was wearing a bra. That’s a pretty girly thing to do. When I was at home I didn’t do anything that was super feminine. Sure, I masturbated, but guys masturbate. Sure, I walked around in the nude, but guys do that too. Guys don’t wear bras, especially ones marked ‘DD’.
I shook my head to allow some new thoughts into my head. Of course I was wearing a bra. I needed it keep my breasts from bouncing around the place. There was a reason why I needed to do some girly things- I had a girl’s body. I may be male in my head but my chest is 100% female. I wasn’t going to last long if I rejected my own body. I needed to adapt. Hell, since I’m here I might as well try and have fun! “Jenny?” called Alice.
“Yes?” I said in my girl voice.
“You’re quite large in the bust, so I’m going to give these to try on. I’m not sure the strapless will work, but it might.”
“Have you got any push up bras?” I said, embracing my body.
“Jenny, have you looked in the mirror? You don’t need a push up bra.”
I chose and paid for my choices. A lot of silk and satin and things that felt nice against my skin. I even got a few thongs that Doug said, “Would decrease VPL,” whatever that means. I went back into the dressing room and put one of my purchases back on. I felt supported, and now my boobs didn’t dictate how fast I walked.
And the shopping continued, as each item I wore I looked a little more like a normal girl in her twenties. I got some sneakers, some small heels and a pair of ‘fuck me’ boots at the shoe store. I got some earrings, bangles, a pair of sunglasses and a necklace that nestled restfully in my cleavage at a cheap jewellery place. I got jeans, pants, an absolutely tiny pair of shorts that Doug talked me into, a few tank tops and halter-tops and even a skirt. I made sure I had comfortable clothes if I was going to work picking fruit at Barrel’s Uncle’s farm.
The guys joking tried to get me into a dress at every opportunity but to no avail until I found a jacket on a mannequin that I loved. “I think that jacket would look great on me,” I pointed out.
“Everything so far has looked good on you,” agreed Barrel.
“The jacket goes so well with the dress,” hinted Doug as he winked at Barrel.
“Yeah, every girl needs a little black dress,” said Barrel, sounding more like a girl than I ever had.
“You’re such a homo,” I said punching him on the arm, “If you like it so much why don’t you wear it?”
“I don’t think they make it in my size, Scott!” Barrel said loud enough for passers-by to hear.
“Shhh…” I said.
“Come on, try it on and if it doesn’t look super sexy on your hot bod you don’t have to buy it,” challenged Doug.
“Yeah, I thought you wanted to embrace your girly side,” said Doug. I knew I shouldn’t have told him about my decree in the changing room.
I was alone in another dressing room in a long line of dressing rooms. This had truly been a whirlwind tour. I had a whole wardrobe of clothes within one hour and a half. This would probably be last thing I tried on and I was glad. While playing dress up was fun for a while there were a lot of things I would rather be doing. The thought of playing with myself popped into my head and I let it linger. That was a whole lot more fun than shopping. I removed my sneakers, wriggled out of the well-fitted jeans I now wore and took off my tank top. If the boys were so adamant to buy me more stuff, who was I to argue? I slipped the dress on, providing the curves on which to cling to.
I looked better in it than I did naked, a feat no clothes so far had even come close to reaching. It clung to my body like a second skin. It was very low cut, introducing my breasts to the public. It was quite short, my sexy thighs revealed. The mirror informed me that my ass was given the same public treatment as the dress hugged my butt like they were old friends. It wasn’t trashy, like some of the other dresses the boys wanted me to wear. This was classy. This was sexy. I slipped on the jacket and it was complete. “I am Jennifer,” I said because that’s how I felt.
I slid open the curtain and wiggled out, my ass dancing provocatively for anyone who dare look. The boys looked at me, there was nothing else they could do. It was like the very first time they saw me, I half-expected them to run away again. I ever so slowly turned around, giving them the complete view. “What do you think, guys?” I asked them, already know the answer. In response Doug turned to the side, exposing a healthy looking erection. “I’m so fucking wearing this tonight!” I squealed, squishing my boobs together and posing.
The boys forked out the money for the dress and jacket. “You’re so going to be a cock tease tonight,” said Doug, “You’re going to ruin so many guys' pants!”
“It’s going to be so much fun,” I imagined out loud. We walked towards the exit of the store, as we did we past the make up counter. As a boy I had walked past it many times and never had noticed it. I was on my way to the electronics or book section and never had any need for make-up. I guess years of passing it by had some effect on me because I didn’t even notice it.
“What about make-up?” ask Barrel.
“You’ll need make-up for your big night.”
“I don’t know how to put of make-up though, Barrel!”
“But the girls do it for you..” he said taking my arm.
“You’ve already spent so much on me, guys!”
“You’ll find a way to pay us back,” suggested Doug.
“No sex!” I comically put my foot down.
“How about a B.J?”
“Maybe,” I giggled.
“Hi this is my friend. She doesn’t know how to put make up on but can you please teach her. She’ll buy stuff off you.” Barrel’s introduction made the make-up counter women laugh. Especially since he said it all in one breath in his typically monotone voice. But they were sweet. They asked what the event was and I told them and I showed them what I planned on wearing. And they talked my through all the basics, foundation, blush, lipstick, eyeliner. They were very nice and said I didn’t need much because I was such an extraordinary beauty. They asked me if I was a model. I answered ‘no’. I asked if they could do my make up for tonight and they explained day make-up and evening make-up was different, but I told them I was going straight home and not doing anything until my big night, so they agreed.
I tried to take in all the instructions and advice but it was impossible. The first problem was they would chat so quickly, secondly I was enjoying my image in the mirror too much. When they were finished, my make-up looked amazing. They did an awesome job highlighting my big, bright blue eyes and my full, luscious lips. I thanked them and Barrel once again handed over a small fortune. “Haven’t you spent enough of me?” I asked. Barrel winced, looking at his depleted wallet,
“Now we have. Let’s go! Hey, Jenny?”
“Why yes Barrel?”
“Does make-up feel weird?”
“Only the lipstick,” I said licking my lips and heading towards the exit.
“No shit! You could pose for Playboy looking like that!” said Doug as he chewed his Subway sandwich. The boys had stopped for some much needed lunch. I, not wanting to ruin my make-up, avoided lunch spinning some tale about how my stomach must be smaller now that I’m a girl. Secretly, I was quite starving but the make-up was so pretty, I didn’t want to try and replicate it at home. “So, what’s it like having guys ogle you, Miss Westbrook?”
“What? Other than you perverts?”
“Why are we perverts?”
“Because you guys know I used to be a boy!”
“You sure don’t look like a boy.”
“Or taste like one,” laughed Barrel, remembering the finger incident of the night before. I thought about the original question as an older guy from our high school walked past, all the time staring at my chest.
“I guess not being ogled is worse than not being ogled,” I stated as my philosophy.
“I’m not sure. I kinda like being the centre of attention for once,” I smiled as I felt a few pairs of eyes watching the wiggle in my walk.
We arrived back at my place about 2. I invited my friends to come in for a while but they both said they had to get home. We sat on my porch, bag after bag of clothes beside us. “Well, that was quite a sleep over!” said Barrel. That was an understatement. Within the space of 24 hours, I had been shot, had my friends bat around my boobs, reciprocated by masturbating in front of them, titillated a pizza guy, watched some movies, went shopping and wore my first dress. That was quite a sleep over. I desperately did not want the boys to go home. I wasn’t sure what I do without them. Sure, my plan was to go to a bar but I always dreamed the first time I’d go out would be with them by my side. Three men out on the town. They had even promised to wait until I turned 21 before they’d go out.
Doug awkwardly joked, “Man, you’re going to have fun tonight! Meanwhile I’m going to be looking at boring holiday photos with Granny!” His phone beeped and he said he had to go because his ‘rotten mother’ demanded they leave soon. He retreated to the backyard to get his bike. Only to shoot off past us, hurtling down the road, yelling,
“So long faggots!” I laughed alongside Barrel who bellowed loudly, but I wanted to hug Doug and thank him for the support and for all the money he spent on me.
As Barrel got on his bike, I thanked him. “I’m not leaving forever, dude!” he said slinging his backpack over one shoulder, “I’ll be back tomorrow morning at 10ish and so will Doug. We’re going to help you get a life started. Get heaps of stories for tomorrow! The bar would be so fun! Hey! You could go to a strip club!” I rolled my eyes, gesturing to him my own body. “I guess you’ve already got your own strip club. Enjoy tonight!” and he began to peddle home.
And I was alone, again.
I ambled inside and began cleaning the lounge room. I vacuumed around picking up bits of corn chip on the floor. Normally when my friends went home after a sleep over, I’d have homework to do or chores to do, it was good to have some peace and quiet. But now the quiet scared me. I had less than a week to get out of this house and start an entirely new life. One where I have to do my own laundry. One where I have to pay bills. One where my parents weren’t around to help me. So, I cleaned up the lounge room, without being asked to, practising what it would be like by myself. But it might be fun in my new house. The boys could come and stay every weekend, if they wanted to. And if they didn’t this is the perfect body to make friends in! I wondered about the incredible people I would meet tonight- other sexy girls out for a good time, awkward guy out to impress me, funny guys out to impress me, handsome guys out to impress me. My nipples pricked up as I thought about the ways I could entertain those men. I absent-mindedly let a hand rub my crotch through the blue denim. “Stop!” I said our loud, “You’ll have time for that later.” Since it was only half past two I did have time for a rather lengthy masturbatory session right now if I so wished but I wanted to do some more ‘normal’ things this afternoon. Things that made me feel like a human, not a walking sex toy.
Tried on some of my new outfits.
Laid out my ‘bar’ outfit for the night.
Learnt to walk in heels, fairly well.
Checked my email.
Created a Myspace page for Jennifer Westbrook. And added only two friends.
Posted a picture of me on Hotornot.com (After 2 hours, 347 votes, 9.9 average!)
Researched what sort of jobs were available for me in the area (Looks like I’ll be a waitress.)
Put the gender changing gun back in its box and put it in a safe place.
Caught up on some sleep.
I have a pretty good body clock and I awoke a few minutes before my alarm was set to go off, as I often do. I sat up, this time not shocked that I was still female. It was quickly becoming a habit to sleep in the nude, and I enjoyed the way my sheets felt on my smooth body. Oh my! I was still impressed by this body. Hardly any girls at the mall had an impressive rack like mine and hardly any of them had a curvy butt like mine and not one had both! I was truly something else. That dress popped into my head and a smile crept onto my face. This was going to be a fun night indeed.
I positively skipped to the bathroom, the now familiar feeling of having my boobs bounce around the place. I was pleased to see that my make-up needed only the tiniest of touch-ups, which I did with mild aplomb. I blew a kiss to the mirror and my male side assured me I was boner inducing hot! I slipped on my panties for the night, which happened to be a red silk thong (Since I didn’t want VPL in my new dress). Since I didn’t try them on in the store, this was my first time wearing what Barrel called ‘butt floss’. It did feel weird, like a comfortable wedgie. I checked out my ass in the mirror. I’m not sure why but asses just look hotter in thongs, and this thong and this ass were no different.
Next I corralled my knockers into their silky confines. Posing a few times I was certain I could destroy Heidi Klum. An excited giggle bubbled out of me, as I knew what was coming next. I hurriedly pulled on the masterpiece. Getting an electric thrill from every inch of skin it touched, I tugged it down to just below my perfectly formed ass. I looked in the mirror and said, “Wow!” There was something magical about the combination of me and this dress. My ever-prepared nipples stood to attention just thinking about what things could happen to me tonight. I mischievously played with my two new friends but stopped when I realized I didn’t want to ruin my new panties. I slipped my jacket on and slipped some of my money into my purse. I’m not sure how much a ‘big night’ would cost so I put $250 into a purse the boys had bought me. At first I was against a purse, but knowing I wouldn’t always have pockets it was kind of a necessity. I put on my earrings and bracelet and let my necklace nuzzle my cleavage. Finally I climbed into my ‘Fuck me’ boots and zipped them all the way up to just below my knees. Thanks to an entire afternoon walking in them I now walked ok in them. Hopefully the situation would never need more than a saunter, as that was my best speed in the boots.
I looked like heaven.
I was ready! I clapped with delight. The teenager in me was so keyed up to go to a bar, undetected. I was a 14-year-old boy hiding inside a drop dead gorgeous woman. It was a perfect disguise. If more young boys knew about the gun, the bars would be flooded with heavenly bodies such as myself.
But I was nervous. What was I going to see? What was I going to do? It was too late to back out as the taxi beeped its horn. I left my house, and prepared to travel into a whole new world. I told the driver I was new in town and looking for a fun night. He nodded and said, “For a beauty like you, I’ll take you to the nicest bar around.” I was beginning to enjoy the way guys now treated me.
I sauntered into the bar, in a dress that announced ‘I was interested in some company’ and with body that announced ‘It was worth a special effort’ I was giddy that I was finally in a bar but confused about what to do next. I was planning on dancing but this place only had the faint tinkling of piano, hardly worth bumping and grinding to. I sat nervously on the stool closest the door. Alone. My body may look like it fitted in here but my mind had no clue what to do. From inside my purse, my phone called out. It was a message from Doug:
“GRANNY = BORING!! HOW GOZ UR BIG NTE, MISS JENNY?”
I looked around and saw nothing but scores of people in their own conversations, in their own worlds so much so that they didn’t even notice the blonde bombshell that wandered in to this quaint establishment.
“AMAZING! CUM 2 MY HOUSE @ 10 2MORROW + ALL TELL U DA STORIES. I’M A LIL DRUNK 2! HAV FUN, LOSER!”
The last sentence was less for him as it was in instruction myself. The phone had finished sending the message and I looked up at the lonely bar. In front of me stood the barman sliding what looked like a glass of wine towards me. “With compliments of the gent at the end of the bar,” he said.
“Thanks.” I picked it up and sniffed it, hesitated and took a tiny sip. To the world I appeared to be something of a wine connoisseur, but in reality I was a 14-year-old boy having his first wine. It was strong. Too strong. This stuff would take some time getting used to. The man at the end of the bar, the man who sent me the drink nodded welcomingly. He seemed old. Maybe 25. I had to remind myself that I too looked 20ish. He was good looking, I decided to beckon him over. I smiled, too big to be considered wry or sexy, instead I looked eager and dorky. Strike one. Not that this body could look dorky for long. Seconds later I casually tilted my head and grinned, in one move saying, ‘Come here and sit by me. We’ll think of some ways to have fun,’ it was the single sexiest thing to have ever happened in this bar to date.
“Hi,” I purred when the man reached my end of the bar, “Thanks for the drink.” He looked at me. Into my eyes. He was man enough to take a peek at my impressive cleavage but enough of a gentleman to leave it at a peek.
“My pleasure. I wanted to cheer you up, you looked a little sad.” He gave me a look, asking me if he could sit beside me. I nodded.
“I’m not sad,” I reassured him, “I’m just new in town. I was looking for a fun place to hang out and the cab driver took me here,” I absent-mindedly played the charm at the bottom of my necklace at the top of my breasts, “I guess I was looking for somewhere a little more… fun.”
“Well, I know this town very well. I’ve lived here all my life. I can show you someplace… fun…” I was thoroughly enjoying this flirting business; I licked my lips, slowly, intentionally and watched his eyes follow the path of my tongue. I raised an eyebrow and nodded, accepting his invite. I felt the less I said the less likely I would say something foolish. “Excellent, well I’ll wait until you finish off the drink and I’ll take you dancing. What do ya say?”
“Sounds ace!” I said. I sat, staring at my drink. I still had a lot of wine left. I had only taken on sip and I wasn’t looking forward to the many more I would have to do to finish it. “Umm… I’m not much of a wine girl. I like my drinks less strong, more sweet, you know?” He laughed out loud and touched my leg as if we were old friends,
“Well, my little girly, you’re my kinda girl! Let’s get out of this stuffy old place!” He waved goodbye to some friends of his and lead me outside.
There were many things to remind me this was not my average Saturday night. The sounds of my heels, clacking down the street. The rise and fall of my bountiful boobs each time I breathed. The tingle in my pussy, knowing that I was walking alongside an attractive man. I didn’t have heels, boobs or a pussy any Saturday before this one and combination of all things feminine was putting me under a spell. Every now and again my mind would shriek, “You a boy!” or “What are you doing?” but the fun I was having prevented me from running away. The man was quite good looking. He was taller than me, he wore a nice purple shirt that fit his body well. It couldn’t hide the fact he had broad shoulders or a muscle riddled torso. His hair was brown and had that just woken up look that takes men 15 minutes to perfect with the aid of hair gel. Perhaps I was enjoying looking at him too much.
“So, tell me about yourself,” he asked as we begun the short walk to his favourite night club.
“Well, my name is Jennifer Westbrook. I like The Simpsons, video games and hanging out with my friends.” That didn’t seem to be enough, but I didn’t know what else to add, so I just turned, smiled as asked about him.
“My name’s Toby. I’m 24. I’m an accountant, I also like the The Simpsons and I think you’re the most beautiful woman I’ve ever laid my eyes on.”
“You should be glad I’m new to this flirting thing,” I giggled, “Because no other girl would fall for a line like that!” I punched him, like I would Doug or Barrel.
“Oww!” he mock-cried, “That hurt!” I leant in and gave his arm a kiss, right where I hit it. “All better,” I whispered.
“Remind me to let you punch me on the cock later!” The boy inside me laughed and the girl pictured kissing Toby’s rising cock.
We turned a corner and were greeted with a long line to the club. “Aw shit!” exclaimed Toby, “The line doesn’t usually get this long this early!” There was a fair amount of people in the que and it didn’t seem like it was moving quickly.
I pouted, “How long do you think we’ll have to wait?”
“An hour, maybe longer…” guessed Toby, good-naturedly waiting at the end of the line. I didn’t want to waste my night waiting. I had spent too many Saturday nights waiting. Waiting for my friends to show up. Waiting for a movie to start. Waiting for game to finish downloading. Waiting for my parents to leave the house. Waiting for a girl to call. Waiting for this magical thing to happen to me. I huffed impatiently and hung my head to sulk. That’s when I spotted them. Proud, full, round. I remembered how powerful these things were. Even encased in my dress they were still forces to be reckoned with.
I stood up straight, handed Toby my jacket and purse, puffed up ‘the twins’ and said with a mischievous smile, “I’ll get us in!”
I wiggled my way to the front of the line to introduce the bouncer to ‘the twins.’ First things first, the bouncer was male. It would have been a mite harder to convince a woman to let me in, considering my boobs inspire lust in men but jealously in women. I sidled up to the bouncer, pouted extra hard and focussed. I had practiced sexiness in the mirror but now came a true test of my skills inside this perfect body. The bouncer eyed me appreciatively. “Excuse me, sir,” I murmured, “I was wondering me and my friend could get in”
“You- yes. Him- back of the line,” he said eyeing me up with uncontrolled lust and Toby with contempt. It seemed like he was punishing Toby for having a chance with me.
I upped the sexiness, squeezing my boobs between my arms as I plead, “Please, I don’t want to wait for an hour for him to get in. I’ll be your best friend.” It was a take on the old elementary school classic with added boobs and eyelash fluttering. The bouncer seemed moved by my plea. “OK Blondie, just because you are a total smoking hottie here’s what I can do. You can come in now and I’ll let your friend in 20 minutes.”
I was about to throw a tiny tantrum when Toby spoke up,
Toby took me aside and whispered, “Go ahead, go in, have a drink and a dance and before you know it I’m in! It’s better than both of us waiting out here for ages.” His hand gently cupped my ass, rubbing it softly.
“OK,” I said blowing Toby a kiss, “Thanks so much for understanding! I’ll see you soon!” I skipped into the already heaving club leaving Toby my new friend behind, still clutching my bag and jacket.
I overheard the bouncer saying, “And what a piece of ass!” as I disappeared through the doors.
This was the type of place I wanted to go to! The music thumped while people danced wildly on the dance floor. Pretty girls in tight jeans and hots pants writhed away while men clamoured to be next to them. I was going to the bar and I’d get a drink and that was my plan. Shit! Toby has my purse! No money, no drink! This wouldn’t have happened if I were a guy, I thought. However I never would have got into this place is I was ‘old Scott.’
Transfixed by the whole place, I didn’t notice the eyes covering my body. A dozen pairs of eyes from all around me watched my every move. “Hey, do you want to dance?” some one asked me; I turned to look ay my potential dance partner. She wore very tight low-riding jeans that left nothing to the imagination, which was lucky because nobody could possibly imagine an ass as fine as hers, her top wasn’t much more than a bikini top but support wasn’t too much of an issue for her since she wasn’t mammary-gifted like I was, she wore a white fedora which complimented her long brunette hair just right. I wasn’t used to being asked to dance by hot girls, that fact coupled with the fact I was myself, a hot girl, made me ask if she was talking to me. “It’ll be great,” she promised, “Two sexy girls, like us, dancing will really heat this place up!”
On the way to the dance floor we exchanged names. She was Meg and I still was Jenny. This was one of her favourite spots to go and tonight it was filled with amazingly sexy guys, Meg explained to me, and there was nothing in the world better to stir sexy guys up than two women enjoying each other’s company on the dance floor.
As a rule, 14-year-old boys don’t dance. They may play air guitar, they may mosh, they may try and cop a feel of an ass or a boob in the name of ‘slow dancing’ but they do not set themselves up for the ridicule that dancing attracts. As another rule, all sexy women look infinitely more alluring when they dance. There are thousands of youtube videos attesting to that fact. Looking at an attractive woman’s form is one thing, watching it undulate is whole other ballgame. But as either woman or a boy, I hadn’t danced. I wasn’t sure if I could do it right. Meg must have noticed I was a little nervous because she said, “Relax Jen, just let your body take control and follow my lead.”
I turned my brain off, or at least the part that control inhibitions and the little voice in my head that still yelled at me for being a girl. I felt my hips sway to the music, my stunning ass following the hips. At first I didn’t know what to do with my arms but watching Meg embrace her body and wave them in the air, I soon caught on. I spun around, feeling my glorious mane of hair fly wildly into the air and float back down. There was a whole line of men too scared to join the dancers who were clearly enjoying our little show. Meg brought me closer, squeezing our two bodies together. I cherished the feeling of all our four of our boobs mushing together. She glided up and down my body like a stripper working a pole and I did my best to return the favour, getting quite a thrill when our butts pressed against each other. The men elbowed each other not believing the free show they were receiving. I felt dampness down below and that confirmed that I was enjoying myself.
I must admit I wasn’t sure why I was enjoying this so much. Was it because I was getting quite personal with a magnificent looking girl? Or was it that I enjoyed entertaining my new male fans? I hoped it was the first but it was probably both, with a leaning towards the latter. Just like Meg, I imagine. Ever since Barrel and Doug first ogled me I have felt an electric thrill whenever I got appreciated for being the incredible piece of tail I had become. It was addictive having people worship you and I was getting a little bit addicted.
There appeared to be no-one else dancing and being in deep thought at the same time, so I discarded my thoughts. The music was my boss now and I obeyed his every wish with a wiggle and a smile. “You’re a great dancer!” I said to Meg during a quiet part of a song. She responded by gyrated all around me, her hands all over my body, and similarly her body often finding itself under my hands. For the second time in two days I felt a pair of boobs, sure they weren’t nearly as nice or large as the first pair but at least they weren’t protruding from my own chest this time. For about a second I wondered if her pussy tasted like mine and if I should ask her.
“Ready for the show stopper?” she asked me, not giving enough time to answer as she unleashed the ‘show stopper’ on me. She leaned in and kissed me. The assembled crowd collectively cheered. The kiss was tremendously passionate, her tongue rolling around inside my mouth. Taking her lead once more I returned the favour. A hungry hand slid up my body heading toward its firm, spherical objective. A bolt of sexually charged electricity surged to my brain as Meg skilfully kneaded my boob through my dress. Her other hand crept around the back, covertly giving my ass an amorous rubbing. She ever so slowly broke it off and whispered as our lips parted, “Enjoy your night. All your drinks are free now!” Meg then strutted to the bar, a line of adoring fans trailing behind her.
Again, another first for me, my first kiss. I never suspected that the main reason for my first kiss would be to turn on an army of men who had gathered to watch, but on the other hand it was with a total babe and it was before both Doug and Barrel. Doug and Barrel! They were never going to believe this!
I began dancing alone, letting my body take me where the music wanted. From the corner of my eye I watched a cute guy build up the courage to approach me. “You’re a great dancer! You’ve got a totally rocking body!” he said trying to be heard over the music.
“Thanks, you’re pretty hot yourself!” I said, the subtlety of flirting was thrown out the window. The man was pretty hot. He was tall and slender with thick eyebrows and a shaved head. He looked like a swimmer, with broad shoulders and big feet. The feminine part of my mind wandered, thinking if those big feet meant what I thought it meant. I bopped along to the pounding music, letting my body do the work. I watched the man watch my body as it shimmied and shook to the music, his eyes following the contours of my fine feminine form.
“I’m Ben,” he cooed directly in my ear, so that I could hear.
“Jennifer!” I cooed in his.
“Do you want to do shots?”
“Shots? Do you want do some shots?” While the music thumped I didn’t hear Ben at all.
“Sure, sounds great!” I shouted, hopefully he asked me for a drink because I was so thirsty.
Ben grabbed me by the hand and guided me through the crowd towards a quieter bar at a back of the club. Excellent, I had made the right choice to a question I hadn’t heard. He ordered our drinks and the bargirl lined up eight tiny glasses, four for me and four for Ben, my new friend. The cute bargirl then filled each tiny glass with a dribbles of different alcohols and put down a saltshaker and some lemon pieces. I’d seen people do shots on TV and always wondered why they drank from such small cups.
“This is a club speciality, it’s called a Rainbow Train. You have to do each shot one after the other. It’s the ultimate rush,” he stared at my face drinking in my beauty while he explained, “Ready?” I eyed the glasses, it didn’t seem like a lot of alcohol.
“OK, Jenny! On the count of three,” he placed the first two glasses in each of my elegant hands, “One… Two… Three!”
The tangy liquid trickled past my robust lips, down past my awaiting tongue and attacked my throat. It burned, bad. That’s why it’s such small glass! I was about to vainly protest but Ben, eagerly pushed my other hand up, daring me to continue, “Keep going! You’re a big girl!” He wasn’t completely right, inside this big girl was a little boy who had never done shots before and aside from the miniscule sip of wine earlier and a thimble’s worth of beer just once, just to try, he had never had alcohol at all. But I wanted to prove that I could be a ‘big girl’ so I downed the second. While I was recoiling from the second Ben passed me the third. Only one more to go after this one, I told myself while the fire trickled down my throat and into my tummy. He extended the glass out to me, “Last one!” he chimed.
“Wooo! Last one!” I echoed, hammering back the drink, more proud of myself than when I got an A+ on that history exam I studied real hard for.
“Lick my hand!” he instructed holding his palm out flat. Ben seemed to know what he was doing and while it sounded an odd request I had done weirder things last night. I let my tongue sweep his palm, tasting a patch of salt that set off an explosion in my mouth. I recoiled in alarm only to have a lemon wedge placed in my mouth. The experience left me breathless. This was quite an introduction to the nightclub scene.
There was only one thing to say. “Wooo!” I hollered. Enjoying the head rush I had just received, I wriggled with pleasure. The booze, the bar, Ben and the babe I had become made the world spin with no signs of slowing down. I was severely over-stimulated and loving it!
“How was that, babe?” Ben asked me while I gyrated to the music.
I sinfully wiggled over to Ben, making eyes at him while I draped my arm around his neck. I pressed my body against his to prove to him, but mainly to me, that I was one sexy girl. “But it’s your turn now!” I purred handing him his first shot glass.
“I know, I know it is! I’ll do it a whole faster than you, wimp!”
“You’re such a tease!” I giggled.
“It’s true! Let me just get ready,” he said grabbing a saltshaker, “Hold out your hand, sweetie,” I did and he sprinkled some salt on my hand. He looked at me with mischief in his eyes, “For my next trick…” he announced carefully wedging the piece of lemon in the crevasse between my breasts. I craned my neck down, staring at the lemon wedge sitting on its makeshift shelf.
I waved, wiggling my fingers, “Ah dude, I do have a free hand here!”
Ben licked his lips, “But it wouldn’t have been half as fun!”
My head felt light as I cheered Ben on, careful not to loose too much salt or have the lemon tumble down, deep into my cleavage. He was much faster than me, drinking as if it was a proper race. He hurled them back, starting the next shot immediately after finishing the one before. I nervously awaited the final part. Luckily, I guess, I didn’t have to wait long, he finished the different ‘rainbow’ colours and the next I knew I had Ben’s slippery tongue quickly running across the palm of my hand. I braced myself, taking deep breath, my tits rising with the gasp. A nose, a moist pair of lips and the same slippery tongue plunged between my boobs, hungrily searching for a lemon wedge. Ben took a little longer than he should, predicably clumsy in his hunt, allowing him a few more seconds of ‘face-time’ with the twins. It tickled and I laughed, making the lemon wedge fall deeper and extending his time rooting around in my valley. Ben arose, like a triumphant deep-sea diver, lemon wedge firmly between his teeth. “Another round?” he asked, “Or perhaps we can leave out the lemon this time?”
At least Ben was confident. After meeting a girl for only a few minutes he was ready to try and charm her into bed. Even in my tipsy state, there was no way that was going to happen. I was having enough fun playing ‘grown-up’ that sex wasn’t needed to turn this into a fantastic night. I’d save that prize for another day. “No more drinks for me, big boy,” I said rubbing his butt, “I am going to have a dance.”
I left the side bar and stumbled back into the main dance room. Were these heels getting higher? Or did those tiny little glasses have more kick in them than I thought. I didn’t feel ‘drunk’, I felt happy! I felt buzzing! My eyes widened at the sight of the dance floor. It rippled like the ocean. An ocean of people ready to party the night away for no other reason than the night was theirs to do with as they wanted. I imagined the boys, Doug, probably asleep in the car on the way home from another boring dinner with the grandparents. Barrel was probably lying in his bed, remembering his time with his X-Box or my boobs fondly. If only they knew how much fun I was having they might be willing to give up their cocks too. I didn’t even miss my cock at the moment, knowing that every guy in this room would be happy to donate their’s for an hour or two of use.
“Something ridiculously sweet for the lady,” said a familiar voice handing me a florescent orange drink with umbrellas and various fruit hanging over the top. It was a very sweet smelling drink, and I was almost blinded by the colour of it. However it wasn’t the drink that surprised me.
“TOBY!” I squealed doing my best to hug him while not spilling the drink or his beer.
“Hi Jenny. It’s certainly warmer in here!”
“I’m so glad you got in, I’ve been thinking about you every second!” I said, even though I had completely forgot about him.
“That’s so sweet! Here is your cloak room ticket,” he said handing me a green piece of paper, “Hold onto it so you can get your jacket and purse back.” I had completely forgot about them too. I took the ticket and searched for pockets. The dress, though unbelievably boner-inducing, was not very practical. Learning more from movies than I thought, I tucked the tiny receipt into my bra. I hungrily wrapped my lips around my straw, drawing the sugary liquid into my mouth. Compared to the fire the shots created, this drink felt smooth, sweet and cool. “Mmmm… this is great!” I gushed,
“What is it?”
“I don’t know, I just asked for the most girly drink they had,” teased Toby as he brought up his bottle.
“It’s so good!” I moaned.
“Whoa! Jenny, slow down!”
“But I want to go dancing!” I cried, sounding like a petulant 5-year-old girl wanting to ride a pony.
“It’ll all go to your head,” he warned. I decided to use my not-so-secret weapon.
My eyelashes started to bat, my voice became breathy, my boobs seemed to swell on command, I let my foot rise higher and higher near his groin, gently rubbing his thigh under the table, “Don’t you want to dance?”
“I’ll race ya!” he said necking his beer.
My mission on the dance floor was different this time. For my second time I wasn’t entertaining a string of men, it was just for one. If I inadvertently turned on some other people around us, that’s an added bonus but this was all about completely dominating Toby. And this time I knew all the right moves. Also with all the alcohol running through me I felt like I owned the world. I guess it was the perfect balance between too much to drink and not enough. I still had my mental faculties and could think fairly straight but I was happy, confident and dare I admit it, a little horny.
Toby didn’t stand a chance. I wiggled, I spun, my hands roamed my body and his. My whole body collaborated together, making me a symphony of sex appeal. He tried to keep up, holding me close and allowing me to smell is manly musk, but I was winning. We merged as the dancing melted into little more than dry humping. We wouldn’t have stopped if the music stopped.
It was very, very easy to let my mind wander to the possibility of sex. All I had to do was picture us naked and turn us 90 degrees. We were already thrusting and writhing. With that image in my head, sex seemed fun. A playful and thoroughly gratifying experience. I thought back to another time, back when I was a pimply little boy and not an exquisite, powerful woman. I thought back to Doug, sitting in the yard, speaking his truths, “Girls should just have sex with any guy she wants to without all these trials and tests. If it feels good do it!”
‘It feels really good, Doug,’ I thought to myself.
The song came to an end and I turned to face Toby, sweat glinting down his handsome face. His deep green eyes invited me to think dirty thoughts. Another song began and he took my hand. Bowing, he said, “Miss Jennifer, may I have this dance?”
A knowing smile formed on my face, “Sure. Your place or mine?”
We left so quickly from the club that we almost forgot my jacket and purse. I had to quickly run back into the club, fish the ticket from within my bra and collect my things. I slipped my jacket on and Toby begun to hail a cab. My pussy began to tingle and I had to stop myself complying with its demands on a busy street. We both piled into the back of the taxi and Toby called out an address not far from here. We pretended the driver wasn’t there and fooled around in the back. When I fooled around in a back of a taxi a few weeks ago, it meant I pulled faces at strangers driving past, now it meant having a tongue in my mouth and a hand on my tit. Toby paid the driver and we stumbled out of the taxi. We made-out while the lift whirred us up to his floor, his hand exploring under my dress, finding the treasure of my thong clad ass. He struggled to unlock the door, watching me rub my ‘special areas’ in anticipation. Toby pulled me into to his bedroom and we collapsed on the bed, rolling on each other.
“Do you like me?” I asked, in the spot between kissing usually reserved for a satisfied moan or a quick breath of air.
“Oh yeah,” he said drawing me in for another lip-lock.
“Do you like me? Or do you ‘like me’ like me?” I asked, reverting to my teenage ways.
“I ‘like you’ like you.”
“What about me do you like?”
“Well Jen, you’re sweet and so funny and…”
Toby said not answering the question I wanted answered. “No, I mean what do you like about my body?” I asked wanted just a little more validation before I went all the way, IF I was going to go all the way.
He let go of me and just stared at me, choosing his words carefully. “I like… your smile,” Toby said, starting off like a gentleman, “and your gorgeous eyes. You’re breasts are incredible!” I jumped up,
“I know, aren’t they?” I said, proudly thrusting them out. They were my new toys and I was happy to brag about them, “Guess how big they are?”
“Umm…” Toby seemed puzzled by the guessing game I had begun.
“They’re Double Ds! You’re about to play with some very nice Double Ds, Toby! Just warn me if you are about to suck on them, OK? It feels great but I might freak out unless you tell me!” I clutched ‘the twins’, mashing them together and moaning, "They feel so good!”
“They do to me too,” hinted Toby, tapping the bed with hands. He forgot all about his offer when I countered with another question.
“Do you want to see my butt?”
“Hell yeah!” he cheered. I awkwardly shimmied out of my dress, my back to him. I unveiled my glorious derriere.
“Out of 10?” I looked over my shoulder and demurely asked Toby, already knowing the answer.
“10! Definitely 10!” he replied.
Toby stood up and approached me. He was eagerly to try out the goods on offer to him. I was also eager to try new things, “Do you want a B.J?”
“Really?” he seemed surprised that I was offering. I’m not sure how sex situations usually go, I knew I had made a few mistakes playing my ‘femme fatale’ role so far, but I hadn’t seem to matter much. This was all an educational experience.
"Oh yeah,” I purred.
“I would love one! Thanks for offering. Normally I have to beg.” I made a mental note to myself.
I slid down onto my knees, I looked up and smiled, “It’s your lucky day then.”
I undid his belt and as I unzipped his pants he removed the belt and threw it in the corner. What I was about to do was seriously girly, far worse than wearing a dress. But since today was all about embracing my femininity I thought I should do it. At least if I get too scared to have sex this will keep him happy. As much as I hated to admit it, I was quite looking forward to this. Nothing quite prepares you for pulling a man’s penis out of his boxer shorts. I may have imagined men’s cocks a few times in the past 24 hours, nut there is something so real about holding a real one in your hands. I seemed big. Not huge, but big. Bigger than mine was but there was no way I was going to say that to him.
It was happy to see me. “Wow,” I whispered under my breath. I think Toby heard it and was quite pleased about it. It was now or never to confess things. “Toby?”
“This is the first time ever doing this. I just want you to have fun, Toby. So you have to tell me what feels good and stuff. OK?” I gingerly stroked his shaft.
“OK,” he yelped like an ecstatic puppy.
I bashfully held it in my hand, lightly stroking it. I lifted it up and licked the underbelly, making sure not to go near his hairy balls. “That’s good” With the encouragement I parted my lips and wrapped it around his penis. About 2 inches were already in my mouth and there seemed to be a few more inches to go. It tasted like I thought it would, droplets of pre-cum sweetening the strong flavour. I slowly took in another inch. I imagined my tongue was a python and I tried to wrap it around the girth. “That tongue thing feels fantastic!” I tried more experimenting. “Don’t suck too hard,” he complained and I eased off. I began to bob up and down on his penis, the classic style, slowly at first and then I built up speed. Toby enjoyed it and told me so, “Ohhh! Good girl! Faster! Faster!” I obliged. I was careful not expose any teeth and doubled my efforts. “Good, Jenny!” He pulled back my hair that was getting in the way. I wondered what my friends would think of me after telling them tomorrow. They were probably going to ask me why I did it, I hoped I had a good answer for them. I hoped they didn’t want one!
The current one I was performing, however, was going very well. Toby’s earlier instructions had turned into satisfied grunts. I was suddenly inspired to do something with my hands. I lifted one of my boobs out of its bra and began entertaining it. I used the other hand to tickle his balls, a decision that made him yell, “YES!” So I guess it pleased him. I kept pumping away with my mouth, varying the speeds. “I’m going to blow!” he warned. I silently praised myself for a job well done, but it wasn’t over yet. “Do you want it in your mouth?” I didn’t know how to answer him because A) My mouth was full at the time and B) I wasn’t sure what I would say. Did I want a mouth load of cum my first time giving a blowjob? How much was he going to blow? If it was too much I’m not sure if I could take it. I wanted to swallow it all like a good girl though.
I guess he made the decision. “Here I go!” he said removing his cock. Startled I leaned back, not wanting it in my eye. He fired a long hot stream all over my chest and neck. It hit me on my right boob first, as he is naturally bent to the left, then my left and then my neck. The first splurge finally tapered off, leaving a few spurts hitting me on the chin and cheek and missing me altogether.
“Wow!” I said, looking down at chest full of cum. I’m glad I didn’t take it in my mouth, otherwise it would be pouring out my ears.
“Sorry. It’s been a while,” he confessed, “I’ve been so swamped at work I haven’t even had a chance to jack off.” In the name of science I took my finger, collected the dollop on my chin and tasted it.
Not bad, I decided but that was enough. “Where’s your bathroom?”
I looked in the mirror. “Shit!” I muttered. I had got semen on my new bra. As I mopped myself up I wondered what my folks would think of their little boy- standing in a stranger’s bathroom, cleaning jizz of his new Double Ds, worried that he might not be able to get the stain off his bra. Sure they might not be proud of me, but I wasn’t there little son anymore. ‘I’m a big girl.’ I stepped out of my thong. “Let’s do it, Scott,” I said. It was time to become a woman.
“That was so good! I can’t believe that was your first time,” Toby called out to me unaware I was standing naked in his doorway, “You could be a professional! I’m so drained!”
“Are you ready for the main course?”
“Soon!” he guaranteed, “Just need a few more minutes to refill.” I tried to hide my disappointment. I ran and jumped on his bed, disturbing a man on a mission. I bounced on it like I was 5 again, although this time there was a chance I could knock myself out with my own hooters. “Jenny!” Toby whined, “You’re not helping!”
“OK. I’ll help,” I said collapsing on the bed and doing an encore performance of last night’s show. I spread my legs in Toby’s direction and said, “Watch this!” I began the work he should have been doing himself. I’m not sure what helped, whether it my the musk of my pussy, my yelps of delight, the sight of a girl having so much fun with her own boobs but Toby was desperate to join in. We became two erotic adults rolling around on the bed, kissing and moaning.
“I’m going to suck on these, if I may?” Toby asked pointing at ‘the twins’.
“Be my guest!” With the warning it felt quite good, I let out an impassioned moan. He kissed me and rubbed me all over my naked body. Toby acted like he was having sex with an angel from Heaven and was going to make sure she felt at home. Although he was now stiff as a board he didn’t ram it in me. Toby made sure I was wet with enjoyment.
There was no way that Barrel and Doug would regret transforming into babes if this was the end result. I had a good mind to shoot them tomorrow and show them the joys of sex. I would love to be involved in a threesome or even a foursome if we invited a lucky man to join.
“Are you ready?” Toby nervously asked me after a felt a twinge in his pelvic region.
“Uh-huh..” I squeaked, for the first time in ages sounding more like a 14-year-old boy than the vision of sexual prowess I’d become.
He slid open a bedside drawer, “Let me just get a condom on.”
While he wrestled with the condom, I continued pleasuring myself. I rubbed what I thought must be my clitoris, it sent a mega shock through my body and I tickled it some more. “Ooooh!” I wailed.
“Don’t start without me,” Toby begged, exposing his latex-covered gratification stick.
“I wont!” I said, slowing down.
“What positions do you like?” inquired Toby who was dying to get inside me.
“I love them all, baby,” I bluffed, rubbing myself “Doggie, cowgirl…” I trailed off. I didn’t want to say ‘Missionary’ because I not wanting to sound boring and I trailed off because the only other one I had heard of was a ‘Dirty Sanchez’ and that didn’t appeal to me.
He tapped the edge of the bed and I climbed over. “Are you flexible?” he asked, choreographing our first sexual position. Since this body seemed designed for sex I assumed I was and nodded. “OK,” he said standing up, “Put you’re left leg on my shoulder.” I obeyed, exposing a vagina the ached to be entered. He smiled at me and gently pushed his cock between my two pussy lips.
“Aah,” I squealed, amazed how big it felt inside me. I wriggled in pleasure trying to fit it all in. It seems to keep going, deeper and deeper. “You are really inside me!” I said, astonished.
“Do you like it?”
“So much more than my finger!”
“That’s good to know,” he laughed as he began to pick up speed. With each thrust I moaned, he kept a rhythm going and I loved the friction. This may be the most girly thing I have ever done but it was up there with some of the best things I’ve ever done! Doug was right, why do girls keep this to themselves and only let it out on special occasions? If it always felt this good I’m going to do it a lot! “You feel so great!” he moaned. My boobs jiggled violently and I moaned proudly.
“Do you want to change positions?” he asked. I let out a sound that could be interpreted either way and he slid out of me. I loved every second of it but wanted to see what he chose next. He lay down on his back, a pillow to rest his head. His penis stood up like a sundial. “Giddy up, cowgirl!” he beckoned and I clumsily crawled over to him. I stood over him and delicately lowered myself onto him. I used my hand to guide his penis into him and I slowly sat down, impaling myself on him. I let out a gasp. The last position felt deep but this one felt like his cock was scraping my soul. He smiled as I instinctively began to bounce up and down with one hand tweaking a nipple, the other steading myself. I looked at Toby’s good looking body and thought about how lucky I was.
A warmth began forming and spreading around my body. I howled “Oh god! Oh god! Oh god!” thanking my maker for bliss I felt, although I should have probably been should have been screaming, “E-bay! E-bay!” A familiar feeling builded up inside me, this lil’ cowgirl was about to have her second orgasm ever. I bucked my hips even faster to speed it along. “Yes! Yes! Yes! Yes!” I cried with each bounce. I finally tipped over the top, squealing in absolute delight. This was like last night’s hand made orgasm but bigger. Somehow involving two people made it all the more powerful! I began to slow down, as the good feeling began to ebb.
Toby spurred me on “Keep going, Jen! Ride the wave to the second one!” I continued to bounce up and down, amazed at the fact I could keep going. Then I remembered Doug telling me about ‘multiple orgasms’ in a list of things that I had to look forward to. This gender of mine continued to surprise me!
“You look a little tired. Do you want me to help?”
“Let’s change positions so I can do the work. Doggie?” I nodded and slowly lifted myself off of Toby. I got on all fours, like a dog. Toby then proceeded to ‘mount’ me. Unlike the first time he wasn’t slow and tender, he crammed his penis in me with a rough desire. This was no longer romantic- this was animal. The new force shocked me and I screamed in ecstasy. Things became blurry, a tangled mess of thrusting, howling and passion. My boobs clattered beneath me, crashing into my arms and each other.
“This is good!” I howled, mainly to myself.
“Fuck yeah!” Toby grunted, “I’m about to blow!” I assessed my situation, I was close too but needed a tiny bit longer to make it two in a row.
“Please not yet,” I pleaded, “Just a little more!” I tightened my pussy muscles around his member, drawing out as much pleasure as I could. I implored my body to double its efforts, knowing Toby couldn’t hold on much longer. It was a race to the finish.
“Here I go!” he cried with one last thrust. A thrust that pushed me over the edge, crashing me headlong into my third orgasm. Out of them all, it was my favourite, the one that almost didn’t happen, happening the exact same time as Toby grunted, filling the little tip at the head of the condom. I felt him shrink inside me. Toby withdrew, his little fellow looking tired and sticky. My pussy felt warm. He collapsed on the bed, a grin from ear to ear. I was officially a woman now.
As a woman I had a shower, slowly cleaning myself. Men’s orgasms, in my experience, last for a short, intense burst and then it’s all over. You feel drained, tired and empty. I laughed at them while I showered, positively glowing in my post orgasm heat. I had bundled my hair in a shower cap so as not to get it damp. There were so many downsides to my sudden transformation that I would have immediately gone back to being Scott. But given a choice of being male or female- female, so far, won hands down. “Looking good!” Toby complimented me as he wandered into his bathroom to throw his used condom in the bin and splash some water on his face.
“Thank you. Now promise me you aren’t going to fall asleep right away. We’re going to cuddle, right?” I said, playing on stereotypes that I knew.
“I can’t keep my hands off you,” he said as he climbed into the shower with me letting his hands prove his point. He massaged me as we finished cleaning each other, playfully drying each other.
I had found the silver lining. I may be homeless and directionless but I knew how to have a good time. We lay in Toby’s bed, still naked, spooning. He was one tired man, he fell asleep while gently rubbing my knockers and his hand was still there. I thought my friends again. They may have created a monster. They created me to learn about sex, and while they weren’t going to get any practical lessons, they were going to hear quite a lecture tomorrow. I drifted asleep dreaming of the tales I had to tell them.
My phone rang from inside my purse. The sound dominated the bedroom where I slept. The only sounds it was competing against was the birds outside and deep breathing of Toby. I hurried out of bed to grab my phone. I unzipped my purse and looked at the display. It was Doug. “Big night, Scott?” he asked when I answered.
“You must have had a big night! Barrel and me have been banging on the door for like 5 minutes. I can’t believe you could sleep through all that.”
“I’m not at home.”
“Where are you?”
“Umm…I went out for a morning walk…I was feeling good, so I took a walk.”
“OK. How far are you away?”
“About 10 minutes.”
“We’ll be waiting on your porch.”
I looked over at my companion. He looked peaceful, a sly smile of his face and a morning erection. I gently shook him. “Morning,” he whispered.
“Hello,” I cooed standing over him.
“That was a fun night.”
“Wanna continue from where we left off?” I quickly weighed up the pros and cons of the two choices.
“I would so love to! But I’m late meeting my friends. Can you drive me home?”
“Thanks so much.”
The sun hurt my eyes a little as it streamed into the car, the trees making the light strobe in an almost painful way. The seatbelt sat uncomfortably between my breasts again. ‘How do any other woman put up with it?’ I thought, ‘I guess they get used to it.’
“So, what’s your plans for the rest of the day?”
“Oh, you know, stuff. Catch up with my friends who it feels like I haven’t seen in ages and then I have to find a place to live?”
“Oh yeah, moving out of your place, are ya?”
“Yeah,” I sighed, “I need a place by myself.” There was a lull. I continued to direct my attractive friend through the suburban streets near my house.
“Just here will be great. Thanks.” I wasn’t where I lived; it was around the corner from where I lived. I didn’t want to ruin my story of a morning walk to Doug and Barrel and I didn’t want Toby to see that my ‘friends’ were two teenage boys.
“So this is it,” Toby said, looking at me with his sad puppy dog eyes, “I just want to say that was one of the best nights of my life.”
“Are we going to do it again?” he said. I didn’t answer him, instead I grabbed his phone, keyed in my number, gave him a peck on the cheek and mouthed ‘Call me.’ He nodded enthusiastically as he drove off.
I looked at myself. Purse and jacket slung over one shoulder. My body still squeezed into my little black dress. The dress was crumpled as it spent the night on Toby’s floor. Since my feet still hurt from last night, I held my long boots in my hand. My hair showing serious signs of bed-head. The boys watched me stroll up to them. I wasn’t surprised when Barrel said, “Have a fun ‘walk’, did you Scott?” I wiggled between Doug and Barrel who sat patiently on the porch. I looked down at my female body and it reminded me of my adventures last night.
“OK boys! I’ve got a few lessons for you today... “
Hello! The author here! If you’re reading this thanks so much for reading it all. I've posted this on FM before but as I am writing a sequel I thought I would post it here too.
Thanks so much for reading. As always you can send me an email if you want to discuss anyhting about my stories, [email protected]
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