Game Theory-Learning To Play
Synopsis: Randy invites two friends up to his new vacation home for a long weekend of cards and beer. When he breaks out some magic rings, things take a turn that threatens to effect them long after they return.
There is sex and language in this story, so please be aware. That said, it's hopefully more about the relationships than the sex, but there is some "R" rated content for sure. This story is something I wrote a couple of years ago and thought I might as well see what people thought of it. I'm interested in actually learning to write better, so any criticism is welcome, either here or in private.
Hope you enjoy!
Stephen Moore tossed the duffle bag onto the bed and took a look around at his room for the weekend. Four days was about right for him to unwind after a stressful week of meetings and deal making. The bed wasn’t exactly 5 star hotel perfect, but it felt about right to him, and everything was nicely laid out.
Outside the bedroom was the distinct sound of his long-time friend, Randy, giving his even longer time friend a hard time.
“Damn, Johnny. That is some shitty luggage! Goodwill special?”
Johnny could be heard making a dismissive but otherwise unintelligible comment. Johnny Song had gotten used to Randy’s reasonably well-natured harassments, over these last few years, but that didn’t mean he enjoyed the attention.
Stephen stepped out of his room and offered his best friend some silent encouragement as he took in the sight of the large living area.
“This place is pretty nice. I can’t believe you actually bought it, you damned cheap-scape.”
“Dude, you wouldn’t believe the deal I got on this thing,” Randy responded. “Economic downturn for them, condo overlooking the ocean for me!”
“You don’t feel even slightly guilty for that?”
“What should I do? I didn’t kick them out of the place. I bet this thing weighed on the bank’s books for 6 months before I took it off of their hands. Besides, that’s the way it is. You make mistakes-you pay for them.
Stephen responded by looking over the kitchen and then stepping out onto the little patio to take in the beachfront view. Randy followed and the two stared out into the colorful horizon listening to the waves crashing against the turf below.
“This is an amazing place. I wonder if I’m paying you too much!”
“Hardly, you dumb fuck! Every dollar you’ve made is due to my hard work, and you know it!”
“Have you been down to the pool there?” Stephen asked as he noticed a nice pool right below them on the ground floor. It looked to be pretty big, but there weren’t many people there-just a few young couples sitting on the side watching the sunset with a drink in their hand. “I wonder if there are a lot of unattached women that stay here, or if it’s all kids and couples?”
“The pool’s nice. The last time I was here there seemed to be plenty of women laying out, mostly after lunch, though.”
The sun was starting it’s descent toward the water causing the choppy water to take on a magical display.
“Look man, lighten up on Johhny, OK? The guy’s ex is ripping him to pieces, emotionally and financially.”
“Dude, I don’t mean anything by it! He knows that.”
“Maybe, but just take it easy on him. I had to work on him for days to get him to agree to this, and I don’t want it to be the last time we all do something together. His pride has taken a few too many hits lately, and you aren’t helping anything with comments like you have been making.”
“Whatever,” Randy said with a shake of his head, “I’ll be good, mommy.”
Stephen had gotten used to Randy’s bullshit long ago. However, as he became more successful, it continued getting worse-and poor Johnny got assaulted nearly constantly by his unpleasant side. It was becoming clear that Johnny was starting to avoid having anything to do with Randy, which was starting to make it harder for Stephen to maintain what little social life he had.
“Thanks, Randy. I would really appreciate that.”
“Hey look, there is a grocery store just on the other side of the street. I’ll grab some steaks and some potatoes and we can grill out tonight. We can alternate who buys, OK?”
“Sounds good to me.”
Stephen stepped back inside and found his friend unpacking his things. “Hey, Johnny, it looks like this place has an awesome pool. Wanna go take a quick swim before dinner?”
“I thought fatty didn’t swim.”
Stephen wondered if the two could ever just accept each other as people instead of targets for short term confidence boosts.
“Nah, he’s going to get food and beer. What do you say?”
“Sounds like a plan to me.”
Down at the pool, Johnny floated belly up in he water beside his friend just staring at the moon as it hung close to the horizon. The pool was mostly empty. The sun had set and the couples had disappeared, most likely planning their entertainment for the night, so the two had the pool almost to themselves.
“Thanks for talking me into this, Stephen,” he said. “You were right. This is exactly what I needed.”
Stephen nodded and looked over to witness two women whispering on the far end of the pool. They looking his way-most likely talking about Johnny. He might be broke, and suffering from a bad divorce, but the guy was a complete chick magnet. He just closed his eyes and tried to forget them.
“Did you say that you were starting to play again?”
“I’ve been working with this woman. She’s got a fantastic voice. If we can get stuff together, we might be able to get some rooms lined up.”
“That would be great, man. I know you miss doing that.”
“Nah. I needed the break.”
“Whatever it takes, you know? It’s not like I haven’t been playing-it’s just been in private, you know?”
“One of my best salesmen has a sister who works down in Nashville. She pitches songs to some of the stars down there. He says she does pretty good, too. I bet she could help you get your stuff out there.”
Johnny laughed, “I don’t think those country fuckers want my shit. They want cookie cutter bullshit. Besides, my stuff isn’t country.”
“Have you heard what they sell as country these days? It’s not country either.”
“Well, I don’t think there is much point in it. No body wants my crap-I gave up that dream a long time ago.”
Stephen had never heard him talk so fatally before. He was starting to miss that bravado that he had struggled hard to get used to back when the guy was starting to achieve local fame as the leader of a punkabilly band back after high-school.
“Well, if you change your mind, I can see about introducing the two of you sometime.”
“Thanks, man. I’ll let you know.”
Randy might have been a cheapskate, but one thing he didn’t skimp on was food and boy did the man know how to grill! Three satisfied bellies sat out on the patio watching the moon’s reflection each with a beer in hand.
“So, I guess I’ll get dishes tonight. Johnny, do you want to alternate, since Randy boy did the cooking?”
“No! Let’s let the loser tonight do the cleaning,” Randy almost shouted.
“Are you serious? You suck at poker, man.”
“As a heart attack. I’ve been doing some reading, and I’m prepared to kick both your asses tonight.”
“Man, you can’t just learn that stuff from reading. It takes time.”
“Whatever. If I lose, I’ll do the dishes. I’m that confident.”
Johnny looked over at Stephen while they were getting up to head inside. “Look guys, I’m broke. I think I’m going to have to sit this out. I’ll do the dishes. It’s the least I can do to cover my drink and what I ate. I feel like a total shit for not helping out with paying for any of this anyway.”
“Don’t worry about it. I’ll spot you $400 for tonight. If you win, you pay me back. If you lose part of it, you pay me whatever you have left over.”
“So, what’s the catch?”
“Let me show you!” Randy said with a huge grin as he disappeared into the master bedroom.
A few minutes, he was showing his two friends a small handful of rings. One of which he put onto his finger.
“You lose the entire $400, and you put one of these on and serve us drinks for the rest of the night, assuming that you lose it before Stephen does. Whomever is the first out of cash cleans and makes breakfast for everybody in the morning.”
“So, I lose and I owe you $400 and I have to wear some ring and serve you two drinks?”
“You won’t owe me the money, man. You just wear the ring.”
“So....what’s the catch? That sounds awfully generous of you.”
“I have to warn you. The ring is magic. It will turn you into a woman.”
“Oh, I see. You’re a total moron. I’m not wearing a dress, if that’s what you have in mind.”
“No way, man! No dress, I promise....unless that kind of thing turns you on....”
Stephen finally stepped in. “Why don’t we do something else, Randy. There’s a huge TV right over there. I bet there is something on tonight. We can hook my laptop up if you don’t have cable or whatever.”
“It’s OK, Stephen. I’ll play along. This guy sucks at poker anyway, so I’m not too worried. I just don’t want to play any dumb games where I’ll be looking gay. No cross dressing, fucker, OK? If I lose, I wear the ring and that’s it.”
“You got it, buddy.”
After an hour, the game was looking pretty typical for the trio’s poker endeavors. Stephen, always the cautious one was up by $60, while Randy was down by over $200. That left Johnny up by more than $150. He was starting to get pretty cocky and the bets were slowly increasing, which made Stephen become even more careful.
“Whelp, too rich for me. I fold,” he declared as he got up to get a beer.
With Stephen out, Johnny felt his confidence surge-he pushed another $100 in, expecting Randy to call or fold.
“You’re a brave man, Johnny boy,” Randy said as he took a long look at the half empty deck on the table. “But, we’ll see if you are as brave as you need to be!” he proclaimed as he moved a number of chips into the center.
With that, it was $150 to Johnny.
“Dude, you’re down by over $400 with that bid. You can’t do that!”
“I didn’t start with $400, pretty boy. I’ve got another $300 here.”
Johnny wasn’t dumb-but he was a little bit prone to being a little bit irrational. So, when Stephen returned with a round of beers for the bunch, he wasn’t surprised to see him push his entire holdings to the center.
“That’s 300 to you, muthah fuckah! Let’s see who’s got reason to be brave!”
Chips moved, and hands were shone.
Stephen couldn’t help but laugh out loud when he saw Johnny’s face. He was white as a ghost.
“Four of a kind?” he nearly shouted. “Who the fuck ever gets shit like that?”
Stephen stared at his full house in disbelief as Randy gathered up the massive collection of chips. With a similar motion, he pushed a single item in front of the crushed man.
“You did win something!”
Johnny stared at Randy for a long time before huffing loudly and rising to his feet.
“Look man, I told you I can’t pay you back right now. You’re going to have to give me some time.”
“You don’t have to pay me back, buddy. We’ve already discussed this.”
“You can’t seriously tell me that you will let $400 slide because I wore a stupid ring.”
“That’s exactly what I’m saying.”
Johnny picked the ring up and looked at it carefully.
“So, I put this on, and then I just get you two beers for the rest of the night?”
“And breakfast in the morning.”
“No kidding? What’s the deal?”
“Dude, I think your memory is going bad. I already told you, it’s magic and will change you into a woman.”
In an exasperated gesture, Johnny slipped it over his finger. He then started toward the fridge.
“Might as well get a....” Johnny stopped mid-sentence wearing a bizarre look on his face.
“What’s up?” Stephen asked his friend, concerned by his odd behavior.
“Nothing,” Johnny replied. “I just felt something weird-you know, like premonition or something.”
He fetched another round of drinks and watched quietly as his friends played a little more. The pace of the game had lightened considerably without his influence. He scratched his hair as it danced around his collar wondering to himself when the last time he had had it cut. “Anyone else hot?”
“I’m fine. But the thermostat is in the hallway.”
Johnny got up and walked over to the thermostat and dropped it down a few degrees. “Hm, it says it’s 74, man. I think you’ll *squeak* need to get it fixed.”
“Wow, Johnny. Think about it, when you finish puberty, your voice will stop cracking!” Randy laughed. Stephen wanted to correct him, but it was pretty funny to hear.
“I can’t remember the last time that happened.”
He slipped into the bathroom to return some of the beer he had been consuming and sat down without even thinking about it staring for a minute at his boxers and shorts as they pooled around his white tennis shoes.
He failed to notice that his hairy legs were now soft and appeared to be completely hair free. He also failed to notice that they became even more feminine while he sat for a moment after relieving himself. He wiped his tiny penis and pulled up the white cotton panties and blue-jean skirt and slipped them over his broadening hips.
He didn’t think anything was amiss as he checked his reflection after washing his hands, and adjusted a hair that dared to stray out of the feminine style it had become a part of. When he rejoined his friends at the table, he instinctively crossed his legs at the knee and rocked his tiny foot up and down, failing to notice that he now wore red sandals with a low heel.
Stephen and Randy stared at the oblivious figure, amazed that he didn’t seem to be aware that he now sported small breasts beneath the too tight t-shirt that he now wore.
“Hey Jenny,” Randy said, “How ‘bout getting me another beer.”
“I just gave you a beer!”
Her voice had similar qualities to Johnny’s. He never had a singer’s voice, but it was smooth and strong. She was no exception-except possibly that hers was even smoother and a little higher, though, it was the voice of a grown woman, and not too high.
“Yeah, but this one is skunky. Please?”
“Fine, I’ll get it. Stephen, do you want another?”
“I’m good, thanks.”
She rose from her seat and clopped in her hard soled sandals over to the kitchen to fetch the beer. Stephen couldn’t help but notice that she hesitated here and there as she reached for the refrigerator door or opened various drawers in search of the bottle opener. “Was it her height that she wasn’t quite used to, or was it fingernails” he wondered.
She plopped the beer down in front of Randy in a very ungracious gesture and took her seat next to Stephen, giving him a soft smile as she got comfortable once again. “If that one’s skunky, you’ll have to make do for a while.”
“It’s perfect. Exactly what I had hoped for,” he said as he took a sip.
Stephen just looked at his friend as she fiddled with the a couple of the unused coasters, unaware of his attention.
Her hair was of the same color as before, but longer and styled in a feminine way-not particularly girly, but undeniably feminine. Her complexion was about the same, but her arms were soft and quite a bit more slender than before. She was now wearing makeup, but it wasn’t overstated. Just a little bit of lipstick and eyeliner. Her ears were pierced and she wore colorful little dangles from them.
When she finally noticed him looking, she called him out on it. “What? Is there something wrong with my makeup?”
“Makeup?” Randy howled. “Johnny, that is you in there, isn’t it?”
She paused for a second. At first she looked confused, as if the name didn’t mean anything to her, and then, as if the truth had been revealed to her, she looked at her hands and then ran to her bedroom and slammed the door shut. “Oh my god!”
Stephen hesitated for a minute and gave his other friend a scowl before heading back to comfort their feminized buddy.
“Johnny?” he said as he knocked on the door.
It wasn’t locked, so he opened it slowly to find Johnny/Jenny sitting on the foot of the bed, looking at herself in the mirror.
“I can’t believe it!”
“Are you going to be OK?”
“That’s me in there. This is so weird!”
“Johnny, don’t worry, OK? Obviously Randy wasn’t joking about those rings, so I’m sure that everything will go back when you take it off.”
She looked over at her friend with a crooked smile, “I can’t take it off, Stephen. It’s stuck!”
“Randy, she can’t take the ring off!” Stephen shouted toward the opposite end of the condo.
“That would be because we agreed you would stay that way until Sunday,” Randy said as he appeared in the doorway wearing a nasty grin.
“Well, it’s negotiable. I can offer you a way to let you win an early out.”
Stephen put his foot down at that. “I think we’ve had enough gaming for tonight. Just let him take it off. I’ll cover the $400 and we’ll call it even.”
“No Stephen,” Jenny said as she stood up and touched her friend’s arm in a very familiar, very feminine gesture, “I’m OK. I don’t want to give him anything more to tease me about. I accepted the bet and I’ll make it through the weekend like this.
“Besides, how much worse can it get?”
They both looked sternly at Randy. “Well, how about the three of us pull out $200. If she is still flush after the first one out, she removes the ring and owes me whatever difference there is. If she is the first to go bust, I get to choose what she wears for the night.”
“No way!” the pretty brunette shouted. “I’m not your fuckin’ barbie doll!”
“Randy, this is ridiculous. Let me cover the $400 and we’ll go find something to watch on the TV.”
“Stephen, it’s OK. Randy, I accept your bet.”
“Randy, why don’t you give us a minute, OK?” pleaded Stephen as he ushered the girl back into ‘her’ room.
“What are you doing?”
“It’s OK, Stephen. It’s weird, but....it’s not really bad. I mean, I can still think, and talk and am still the same old me....just with a longer hair, a prettier face...” she squeezed her breasts in a little bit to emphasize the changes, “and boobs.
“Besides, I’ll kick his ass!”
There was an awkward moment where she looked up into his eyes, seemingly conveying her confidence in the situation, before he followed her out to the dining room where Randy was ready to deal the next hand.
*one hour later*
“No! I’m not coming out!”
“Jenny, this was what you agreed to!”
“You can’t make me come out there. I look like ridiculous.”
“I seriously doubt that. I bet you look hot!”
Stephen pulled his friend away from the closed door to Jenny’s room and ushered him into the dining room.
“Isn’t it enough that you fucking changed him into a woman? Why do you insist on giving him a hard time about it?”
“It’s she now. Don’t forget it.”
“Whatever. Just ease up, OK? She has enough shit going on in her life right now. I don’t think adding to it is very helpful to anyone, right now.”
“It’s helpful to me. I think it’s funny as hell!”
As usual, Stephen was stuck as the mediator in these awkward moments. Randy and Johnny never got along perfectly, and it wasn’t always Randy who was the aggressor. In their younger days, it was Johnny who did the teasing...
Back at Johnny’s door, he tapped lightly and asked if he could come in alone.
She opened the door and let him in, carefully locking the door behind him.
“Wow,” he said without thinking. “You look incredible!”
“Really?” she responded before catching herself. “But you aren’t supposed to see me like that. We are both men!”
“I know. I’m sorry.”
“It’s OK. I should have known exactly what he had in mind when I agreed. I just don’t trust him. I mean, it’s not that revealing....but, it’s still very sexual.”
In fact, what she wore was a rather expensive reproduction of a playboy bunny costume-complete with the bunny ears and high heeled shoes.
“It’s like he was planning this all along! How did he even get it sized right?”
“I don’t know. I guess it’s part of the magic.
“Look. If you just go along with him, he will get bored and we’ll never do this again. OK?”
She put her hand to his face and smiled a weak smile. “Thank you for looking out for me, Stephen. You really are a good friend.”
As the night progressed, Stephen actually won a few hundred dollars from Randy. Jenny was beginning to become a little more comfortable in her role as hostess to the two men, and would even get a little flirty with Stephen but always managed to keep herself in control. By the time it was midnight, she had escaped to her bedroom and stripped herself of the clothes and makeup and was fast asleep.
The other two followed shortly afterward.
Stephen awoke to a gentle pressure on the bed. Looking up, he was surprised to find Jenny sitting on the edge of the bed smiling down at him.
“Good morning,” she said cheerfully. “There’s scrambled eggs and bacon ready, if you are hungry.”
“Wow, that sounds wonderful.”
Together they ate their breakfast on the patio overlooking the pool.
“You seem to be doing OK today.”
“I’m pretty good,” she admitted. “You are right, if I just make the best of this, he’ll get bored and it will be a lot easier.”
Stephen nodded with a smile.
“So, any plans for this afternoon?”
“It might be weird, but I was kind of hoping we could spend some time at the pool.”
“Wow! That’s a big commitment, there. You are going to look very different in your bathing suit today.”
She laughed. “No! All of my clothes are women’s clothes. I have this great little one piece that I know will look perfect on me.”
“It’s so weird. You even sound like a woman. It’s so hard to think of you as Johnny.”
“Well, to be honest, I don’t really think of myself as Johnny. I mean, I am the same person, but I do like girl things, and I think...” she said as she looked down at her plate, “I even want girl things too.”
“What do you mean by that?”
She waved her hands in dismissal. “Nothing. Don’t worry about it.”
She gathered up the dishes, “I guess I should wake piggy up. Should I just pour it into a trough and put it at the foot of the bed?”
“Stephen, don’t call me that now, please? Not while I look like this. I can get through it much more easily if I don’t have to be reminded...”
“OK. I’ll try not to slip up, then, Jenny.”
The sun did feel good, and Stephen had to admit it was more fun hanging out with Jenny than it was with Randy. Actually, Stephen was beginning to wonder if Jenny wasn’t more fun than either Randy or Johnny!
“I can’t believe I did that! I didn’t even drink that much last night!”
“I counted 3 after you put the ring on. I bet you had at least three more before. That’s a lot of alcohol for someone your size.”
“But, I flashed him my boobs! Oh my god! But, yeah, I guess I was pretty drunk. Don’t you dare let me do that again. Not while I’m like this and he’s around.”
“OK, I promise.”
Stephen looked around, and was pleasantly surprised that the pool was empty.
“You seem to be doing OK, now. You make a pretty good chick, if you ask me!”
“Thanks. You are such a smooth talker,” she laughed. “I guess it’s the magic, but it feels pretty natural.”
“You look amazing in that bathing suit.”
“You pig!” she said splashing him playfully.
“You do. You’d make some man a perfect....hottie!”
“Oh, he’d be my personal slave!”
They both laughed.
“Actually, those two girls that were here earlier,” she said referring to a pair of young blondes with large boobs and dark tans, “there was not even a little bit of attraction to them. It’s kind of scary. I mean, I saw them yesterday, and I couldn’t stop stealing glances at them. If it had just been me, I probably would have been flirting like crazy with them!”
“You didn’t feel anything for them at all?”
Stephen would have gladly admitted to Johnny that he would have done almost anything for a night with either of the two girls, but it didn’t seem right to bring that up around Jenny.
“Nope. I thought they were pretty tacky.”
“Yeah! Their hair was all frizzed out from a bad perm, and their skin? Spray on tan! They just looked desperate.”
“How do you even know these things?”
“I don’t know. I guess it’s just a part of me now. It’s like I’ve been a woman all of my life, you know. So, I see things just like I would have if I were born Jenny instead of Johnny.”
They both sat in quiet for a little while, enjoying the sun and the quiet of the pool.
“What’s it like?”
“Being a woman? I don’t know. So far, it’s not bad. My boobs float and that feels weird. They move when I walk which is kind of odd. The bra is a little tight and not having a penis is crazy-but, I can’t say it’s particularly bad.”
Silence once again.
“So, you like men now?”
She splashed him with a mock scream. “You’re as bad as Randy!”
“I’m sorry. I shouldn’t have asked. That’s pretty personal.”
“I guess, maybe a little. It’s pretty wild.”
“Is it the same, except for men instead?”
“I don’t know. I don’t think so. I mean, I don’t notice them quite like I did women. You know, just walking around. But, when I’m talking....”
Stephen backed off, knowing that he had lifted her a bit too far out of her comfort zone.
“I wonder,” he said, hoping to change the subject, “if the things that Jenny does will have any affect on Johnny.”
“What do you mean?”
“Like now, you might get a sunburn. If you do, will you feel it on the drive back tomorrow?”
“I don’t know. I hadn’t really thought about that. I guess we should ask Randy.”
Two of the three sat around the table that night after another stuffing meal of grilled meats. Randy was shuffling the cards while Jenny served them beers. She sat down with a glass of white wine for herself and took a little sip.
“I can’t believe you made me buy you that.”
“What? This just sounded good, and you asked if either of us wanted anything in particular. You didn’t *have* to buy it.”
“Now, now. I’m a gentleman. I would never deprive a woman of her drinks. Especially one as hot as you.”
“Whatever. Let’s just get started, OK?” she said. “I’m probably being completely stupid by agreeing to this, but I feel pretty good about tonight. So if I lose this $400, I wear another ring which will give me bigger boobs?”
“Well, it will make you closer to my ideal woman.”
The thought of becoming Randy’s ideal woman was almost enough to make her ill. But not quite...
“And if either of you lose your $400 first, I can buy my manhood back early?”
“That’s about it!”
“And no more getting you drinks?”
And so they played.
After the first half hour, Jenny was up by $75 and Randy was down by $150 and there was $120 in the pot. This was the biggest hand yet.
“I call!” she declared. She was hardly surprised when she saw the 2 pair and 3 of a kind. “Suckers!” she shouted as she showed off her full house and raked in the $120 winnings.
“Get me a beer, bitch!” grunted Randy while she playfully lined her winnings up. By her calculations, she only needed another couple of wins and she would be a man again.
She rose and walked to the fridge. Stephen couldn’t help but admire her cute little butt as she playfully strutted away from them. She knew they were looking, and the excitement from winning mixed with the 2 drinks she’d had already were adding up, giving her confidence to be more of a tease.
She tossed Randy’s beer right in front of him, starting a bit of an eruption from the top, but carefully sat Stephen’s right in front of him-her hand caressing his back as she passed behind him. He looked up at her and got a little bit tongue-tied....by his best friend!
She took a sip from the fresh glass and gave him a long look. Randy continued to mop up the beer that puddled around the chips completely unaware of her flirtations.
“So, what else will this other ring do?” she asked.
“Well, there are five rings. With all five, you become a sex kitten. Maybe like a porn star or something. I guess one just makes you a woman-so, two would probably make you sexier and stuff.”
“Well, you know. More like a porn star.”
“So, will it make me want to have sex like a porn star?”
“If you wore them all, I guess. But not just two rings. I guess you would probably like men a little bit or something.”
She and Stephen shared a look as she started the ante. “I guess I better not let that happen, huh?”
She managed to stay in reasonable control until round four.
Stephen accidentally started it by getting up to use the bathroom. “While we are stopped, babe, why don’t you get us another round!” Randy said.
She was a little wobbly as she served them their beers. “Where is yours?” he asked as she sat down.
“Oh, I’m feeling just fine. I’ve got a little left anyway.”
“Oh come on. It’s just number four.”
She thought about it, and decided he was right. Hadn’t it been a couple of hours already? “I could have one more,” she said to herself as she poured herself an extra large glass.
“While we wait for the dweeb, why don’t we have a quick bet.”
“Oh god. What’s with you and betting?”
Randy shrugged. “It’s just fun.”
“So, what is it this time?”
“High card draw. You win, no more serving drinks-I’ll serve them the rest of the night. I win, you’ll put on the highest heels you have and wear them the rest of the night.”
She sipped her wine, and decided that it was innocent enough.
“Sure, what the hell!”
He let her cut the deck, and then drew hers. “A queen, YES! I should spill this wine and make you get me another!”
He peeled back his and he shouted, “Woot! Don’t break your ankles, baby!”
His was an ace.
Stephen returned to find her strapping on a pair of 4 inch stilletos.
“Wow, somebody’s drunk!” he said.
“No. I lost another bet to tubby back there. You can’t leave me alone any more, Stephen. That’s my new rule!” she said as they sat down-Stephen couldn’t help but notice that her chair was much closer to his than before. Randy raised a single eyebrow, but said nothing.
“Aw, little Jenny can’t hold her alcohol.”
“I’m NOT drunk!” she declared and took a few big gulps of wine as if demonstrating the fact. “Big fucking deal. I’m wearing high heels! Us girls do it all the time!”
It might not have been glass number three that did it, but by the time she poured the last drop of wine into her glass, her chips had dropped to only about $60. And her betting wasn’t slowing down at all. In her defense, though, she was drinking more slowly than Randy, who was working on number 9 or 10.
So when she finally lost it all, they both were struggling to speak clearly.
“Oh my god! I’m going to be a slut!” she said as she looked at the ring.
Stephen took the ring from her, “That’s enough. She’s plastered. Let’s just go to bed.”
“No way. She agreed to the bet,” Randy struggled to say. “She has to wear it!”
“I don’t cheat on bets, mister!” she said as she clumsily grabbed the ring back and before Stephen could stop her, she slipped the ring over her finger.
“Well, that’s it. She’s locked like that until Monday,” Randy stated proudly.
“Let’s move into the living room, at least,” Stephen said as he helped her onto her wobbly feet.
She practically fell onto the couch and pulled Stephen down beside her.
“Man, you two need to get a room.”
“We have rooms, lardo!” she slurred.
“Stupid faggot,” Randy hissed as stomped off to the bathroom.
“Jenny, come on. Don’t talk like that.”
“Oh Stephen. You probably hate me. I’m such a jerk.”
“I don’t hate you. But, you are just making it worse for yourself doing that.”
“I know. He just makes me feel so dumb-and it makes me really mad.
“I’m glad you are here, though,” she whispered as she slipped in closer to him. “You work so hard to keep everybody happy. You are so sweet!”
The two looked at each other. Stephen could tell she had changed. Her hair was already a little lighter and her face seemed softer...maybe a little bit younger. He had found her attractive before, but this woman before him was incredible!
Her eyes never left his as she lifted her hand up to his cheek. “Why wasn’t I born this way?” she asked. “You are so perfect.”
And then it happened. He kissed her.
It didn’t last too long. But to Stephen, it felt like it lasted forever.
And he didn’t want it to stop. He knew he should, but it felt so good.
Randy found a movie for them to watch. In the dark room, Jenny snuggled up close to Stephen as they watched the movie together. Or, at least they started watching the movie together.
Her first move was to slip up under his arm. Stephen’s hours had kept his social life to a minimum, and dating was something he hadn’t seriously considered in years. So, having a soft, attractive woman resting her head on his chest was vastly more intoxicating than the drinks he had consumed earlier.
Neither payed much attention to the movie once she started running her hand over his stomach and chest. She seemed to be mesmerized by his masculine body, and couldn’t take her hands off of him. A part of him told him to stop her, even get up and go to bed, if necessary, but he just couldn’t bring himself to break the wonderful trance the two were sharing.
He adjusted his sitting position after a few minutes, and she actually ran her hands down his belly over his pants to feel the growing erection. Instantly, he was totally aroused.
She didn’t say anything. Neither did. She just took him by the hand and led her sweet friend into her bedroom. Once inside, she peeled his shirt off and plastered his chest with kisses. She was on a mission and couldn’t keep her hands off of him.
Except to remove her own shirt.
It was dark, but Stephen was confident that her breasts were notably larger than they looked earlier in the evening. They pressed gently against his chest as she kissed him. She pulled herself up onto her tip toes to meet his kiss until they collapsed together onto the bed.
She struggled with her bra with a giggle, “I never was any good at this part!”
He scooted around behind her to give her some assistance and soon, his hands were all over them.
She wasn’t particularly small for a woman, and her breasts weren’t particularly large. But in his hands, she felt absolutely perfect and he couldn’t get enough as he pressed and kneaded and squeezed her soft body-all while kissing and nibbling on the side of her neck.
She kept scooting up closer to him, her breathing already choppy, and ran her hands over his thighs. She couldn’t believe how wonderful it felt to have his arms completely encircle her body....and those kisses on her neck....she thought she might be in heaven!
It took her a lot of will power to finally extricate herself from his intoxicating embrace, but she was on a mission. Pretty soon, she was naked except for her silk panties and he was completely nude.
She sat to his side, exploring his naked chest and shoulders with her hands while they kissed, but slowly wiggled closer and closer to the one thing that held tremendous apprehension and excitement.
Her thigh brushed up against it from time to time, and it was undeniable that he was fully erect, but she shyly avoided it a little longer only to brush up against it once again.
After a while, she could feel it’s warmth pressing against her while she mounted his thigh and rocked back and forth. Her hands were out of control. They were in his hair one moment, then following his shoulders another. And eventually...her slender fingers made their way to his rigid penis.
The first time she touched it sent a big thrill over her body. Kissing a man was weird. Feeling his naked chest against her own boobs was weird. But feeling his erection? It was unlike anything she had expected. And she instantly knew she couldn’t wait to feel it inside her body.
So she began taking her panties off but was stopped before she could get her feet out from inside them. Her hips pressed against his groin and she could feel him poking at her little waist. She wanted him so badly, she couldn’t even fully understand it. But he had ahold of her hands and seemed like he was going to back away.
“I can’t let you do this,” he said. She was devastated as she felt the penis pull away from her body. She scooted closer to compensate.
“You can’t stop now, Stephen. I want it so bad!”
“You will regret this tomorrow,” he said as she pulled her hands out from his. “We both will.”
She was completely naked now and quickly wrapped her legs around his waist. She could feel his balls press against her just a bit, so she began to squirm a little, teasing herself with his body.
“No regrets, baby. This is an expression of more than sex,” she said as her fingers teased him up and down. “I think you know exactly what I mean.”
Johnny was a far more experienced lover than either of his friends, and Jenny used that experience to ensure that Stephen couldn’t resist her. It was after two hours of amazing passion that she fell asleep in his arms, happier than she could remember having been in a long, long time.
Randy had crawled off to bed at some point in the night and wasn’t seen before the two snuck out for brunch at a local bistro, after which, they found themselves walking through the city to do a little window shopping.
“Oh,” Jenny said as she admired her feet in a pair of expensive heels. “These look so wonderful, but it would be so stupid for me to buy them for just a day.” She had spent the last 45 minutes trying on dozens of pairs and kept coming back to this one pair. Stephen thought they all looked great-and thoroughly enjoyed the show as she tried them on one after another. She had fantastic legs.
He toyed with the idea of buying them for her. After all, the $600 wasn’t really much money to him-but it was a huge amount for Johnny/Jenny. “If you really like them, Jenny, I could buy them for you.”
She kissed him full on the mouth and snaked her arms around his, “No. It’s just too much money. What will I do with them after tomorrow?”
Stephen didn’t like the idea of her disappearing on him, so he grabbed an associate who happened to be walking by. “We’d like to get a pair of these in her size, please.”
“Stephen,” she said, “I said no! Please don’t do that.”
“But you like them. Why not enjoy your time here as much as you can.” He nodded to the associate, suggesting that she had a sale.
“What size do you need?”
“I don’t know...” she answered honestly.
Twenty minutes later, they walked out of the shop and Jenny’s feet were adorned in her first nice pair of heels. She practically melted into Stephen’s arm, swimming in a dizzy pool of endorphins.
They eventually found themselves sitting side by side on a large pier overlooking the ocean watching as the sun began to set.
“I imagine Randy is probably waking up about now.”
“Probably,” she laughed.
“I’m surprised that you didn’t have any trouble this morning.”
She snaked her hand into his and scooted a little bit closer. “I told you, I wasn’t drunk. It’s like that other ring made it all disappear. Maybe not all of it, but last night...” She stopped for a minute to look at him, “it was not my being drunk girl. I was pretty drunk when I put the ring on, but...I wasn’t drunk when I...”
She blushed and kissed him on the cheek. “I don’t know what it will be like when I go back to being Johnny, but I don’t really care right now. I have very real feelings that wouldn’t have made sense for Johnny, but they do now.
“Who knows. Maybe I had a boy crush on you before and I just never realized it.”
She leaned into him and rested her head on his shoulder. “I have always really liked you, Stephen. I think the magic just translated that into something more appropriate for a man and a woman.
“I can’t describe how wonderful it is to have experienced this. I just hope I can go back to being the old me.”
Stephen didn’t say a word. He had been alone for such a long time, that having any sort of relationship was new and delicious. It was already hurting to think it was going to end in a few hours-but, he would never suggest that they discuss with Randy the possibility of Jenny sticking around.
They spent the next hour or so holding hands and occasionally kissing while the sun drifted down below the horizon. On their way back to the condo, they met with Randy at a restaurant and enjoyed an expensive dinner on Stephen.
When they returned, Jenny disappeared into the bathroom while Randy questioned his buddy.
“Shit man, are you gay?”
Stephen shook his head and stared at his shallow minded friend. “She’s a woman. We spent the day together as friends. It’s not big deal.”
“Oh, I don’t think it’s quite that simple. You were gone when I wandered off to bed, but your room was empty. You two had sex last night!”
“Maybe we did,” Stephen admitted, “Who cares. She’s a beautiful woman, and wanted to try out sex as a woman.”
“God, I never thought you would do something like that.”
“What is the problem?”
“She might look like a sex kitten, but it’s Johnny! You fucked Johnny last night....that’s so fucking gay!”
“Get over it. I have no problems with how we’ve spent our time together, and I’m pretty sure she doesn’t either. So, if it bothers you, I guess we will give you some space, but it’s really none of your business.”
“Jeez, If I had known you were fucking gay, maybe I would have worked harder on you!”
“Well, you’ll have to get a little better if you want to beat me. I don’t weigh a hundred pounds and get drunk as easily as she does.”
Eventually, Randy decided it was best if he spent the rest of the evening at a bar-leaving the two lovebirds a few more hours alone.
They opened another bottle of wine, and spent the first hour or two talking, but eventually, Jenny decided they had better things to take care of.
“What do you think about this?” she asked as she practiced slowly removing her blouse. Stephen wasn’t exactly a regular at strip bars, but Johnny was, and she did a pretty good job, even if she had only been a woman for a couple of days.
She stood there looking at him with her shirt in her hands, nervously waiting for a response. She felt an immediate sense of uncertainty about standing there in a well lit room with her blouse in her hands. What if he doesn’t think I’m sexy enough? she thought.
“You look incredible,” he said, being rewarded by a shirt in the face.
She did a little turn before wriggling out of the short skirt she had worn. Her confidence dropped again, but his eyes were locked on her body, which made her feel better. He obviously didn’t mind her figure too much, at the very least!
She did another turn, but kept her back to him as she struggled to unlatch the bra. She got a bad case of the giggles as she kept trying to look professional about it while fumbling with it. She looked up over her shoulder at him and pleaded for help-with a smile, of course.
“Can you give me a hand here?”
Stephen lost all control, and the two collapsed on the living-room floor, kissing and pawing at one another’s bodies.
“God, I want you so bad!” she said as he quickly began to strip between their kisses and gropings.
He didn’t say anything as he slipped his pants off-he was taken by surprise how quickly her hands flew inside his boxers.
He loved the feeling of her little hands on his penis. She seemed to know far more about what to do to him than any of the women he had been with before, and he just lay back and let her take control of things. She certainly had plenty in mind about how to spend the next hour or two.
He loved looking up while she straddled him-how her breasts were pulled upward when she stretched back. He loved the expression on her face as she neared orgasm and even better, when she came. He loved even more how loud she was now that they were alone in the condo. It was incredibly sexy to hear her screaming as she she clutched his hands firmly against her breasts while the orgasm overtook her. She ground her body into his even as his post orgasmic penis slowly softened-and then eventually collapsed on top of him.
Both were exhausted.
“I didn’t think it could get any better!”
“I guess practice really does make perfect.”
“That was a pretty damned sexy show.”
“I know! I always loved it when the girl rode up top and put on a bit of a show.”
“I meant the striptease, but now that you mention it, I guess the encore was the best part of the night!”
When the glow subsided, they gathered their things, turned out the lights and began again in the privacy of her bedroom before falling to sleep in one another’s arms a second time.
Jenny awoke first, and snuck out of bed, kissed him on the cheek and cleaned herself before sitting out on the patio to enjoy her first cup of coffee while admiring the beautiful reflections as the sun rose behind her.
She was about half finished with her coffee before she tried the ring. Sure enough, it was big enough that she could remove it, but she just couldn’t do it. Randy plopped down beside her watched her as she struggled with her decision.
“You know, if you leave it on long enough, it becomes permanent.”
He just nodded.
“I guess that would be pretty weird, though.”
“I’m sure you wouldn’t be the first.”
She thought about it for a long time. “Have you tried it?”
“Becoming a woman?”
“No way! It works on women too. I got them hoping to find a woman who would want to be with me and was interested in becoming sexier. I was lying about the porn-star stuff, you know. As far as I know, it just makes you more idealized.”
“Yeah, I figured that was crap.”
“There are other rings, though. There are ones that gives you bigger boobs, higher voice, lots of different stuff. There is probably one that will make you into a porn-star...I don’t really know what they all do.”
“What if I’m not happy when I go back?”
“Don’t talk like that! God, the two of you...together. That’s just too weird. You both are creeping me out.”
“What’s the problem, Randy? I’m a woman, he’s a..”
“Whoa! Let’s stop right there. You are NOT a woman. You might look like one right now, but we grew up together and I know that the real you is a scrawny little punk who almost got a big record contract.”
“Randy. You don’t have a clue, do you? These rings did much more than give me a great body for a swimsuit. And besides, Stephen is a wonderful man and we shared something very nice together. If you have a problem with that, so be it. But, I’m not in any way ashamed of what happened, and you should just get over it!”
Her anger gave her the strength to yank the two rings from her finger and toss them on the end table beside his chair. Wiping away a tear, she disappeared into the shower and cried.
When Stephen arose a couple of hours later, he discovered Johnny and Randy loading up the car. “About ready to head out?” Randy called to him.
“Yeah, can I shower first?”
“Sure. We can grab breakfast on our way back.”
The ride back was unpleasantly quiet. Johnny stared out one window, and Stephen out the other while Randy drove. Riding in the front passenger seat, Stephen occasionally caught Johnny wiping a tear away from his cheek through the mirror on the sunscreen. Stephen hoped that Randy wouldn’t notice his, thanks to the sunglasses.
The next couple of weeks passed, and all three seemed to keep their distance. Randy and Stephen interacted at work, but their usual weekly gatherings at one of the local bars seemed like a thing of the past.
Then one day, Stephen got an email from Randy, sent to his personal account. It was CCd to Johnny.
I’m headed up to the condo this weekend, and am in the mood for some poker. Sound like a plan?
Almost immediately came a reply from Johnny:
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