The aggravation and time consumption of preparing for the Woman-less Beauty Pageant was getting on everyone’s nerves. Tempers and the dresses were getting short for all involved.
“Drew, could you zip my dress up please?” Ronnie asked his friend. Drew snorted and asked “Ronnie, have you ever worn a bra before?" “Why do you ask” was Ronnie’s response.
“You sure look very comfortable and relaxed for a boy that’s never worn a bra before. I noticed your involuntary shoulder shrug we all do to make our bras settle into place. Before I zip up your dress let me check if your bra fits right.”
Standing behind Ronnie in preparation for zipping Ronnie’s dress Drew pulled on one of Ronnie’s bra straps and said “We need to shorten the right strap a bit.” Drew expertly shortened the stray strap about ½ inch. “There, they look even better now but we need to check one other fit option.”
Still standing behind Ronnie Drew put his hands into the open back of Ronnie’s dress and under Ronnie’s armpits reaching up and under Ronnie’s bra. Ronnie could feel Drew’s body heat and warm breath. Drew gently cupped both of Ronnie’s tiny breasts to “confirm size and fit”. It was not an accident that Drew also lightly rubbed each nipple with his thumbs and traced a circle around each nub. Ronnie gave a soft moan of pleasure in response.
Drew was pleased on several levels: that both nubs immediately gave a rigid response to his “accidental” efforts. Even more pleasing for Drew was that Ronnie had responded with a low sultry moan of delight. The real tell was that Ronnie did not pull away, struggle or yell. Ronnie just stood there.
Yes. Drew’s warm breath on Ronnie’s neck and his gentle touch of Ronnie’s breasts had Ronnie transfixed… frozen in place. There was no hint of ‘fight or flight’. Very encouraging to Drew and sensually erotic for Ronnie. Ronnie’s breathing had become a bit more rapid Drew noted. Another good sign. Ronnie’s nipples could only get more rigid if someone would lightly tongue them Drew thought. It was a very pleasing feeling for Ronnie. Ronnie wanted the moment and the sensations to last longer.
Embolden with Ronnie’s non-response Drew more obviously gave each of Ronnie’s breasts subtle but deliberate and slow caresses. Ronnie’s nips were perky like small pencil erasers. Ronnie wasn’t sure if he should ask Drew to keep petting his breasts. Drew’s touches felt so very good, so forbidden... excitingly forbidden.
Speaking softly from behind into Ronnie’s left ear Drew said “I can tell your bra is too loose. It shouldn’t have been so easy for me to cop a feel if your bra fit better. Let me tighten your bra band clasp. One or two notches tighter should do the trick and with any luck it should also give you a bit of cleavage. Do you mind?”
Still facing away from Drew it took a moment for Ronnie to compose himself but eventually Ronnie turned to face Drew and softly replied “No… I don’t mind. I don’t mind at all. Do you?”
As they looked at each other it got a bit awkward feeling. Ronnie broke the moment, took a breath and asked Drew “Is there anything that YOU may need help with. ANYTHING?”
Without breaking eye contact Drew replied “Yes there is. Maybe you can check MY bra fit sometime... maybe in my room later. Bring your favorite panties and a dress or two so we can be sure which looks best. I also have a couple of nice bras that I’m sure you’d appreciate. And I have an extra pair of bra inserts I know you’d love. They have a perfect heft to them. And I don’t want to be wearing a similar outfit as yours during the pageant." Drew smiled. Ronnie blushed AND smiled too.
Before exiting the dressing room, almost as an afterthought Ronnie mentioned to Drew “I never did answer you about me having worn a bra before. Yes I have. And panties, camisoles and nylons too when the mood suites me. They make me feel special and secure in an odd way… but never in public unless I also wear a t-shirt and jacket. No one knows but you.”
Still smiling Ronnie felt a strong sense of relief of having shared his secret with an understanding friend. A good friend. A friend that lived nearby. A friend with SPARE bra inserts! Just maybe Ronnie thought, maybe my panties will also need to have their fit checked. Ronnie chuckled inwardly at the thought and made a metal note to pick up a bottle of wine or two.
Ronnie had to restrain himself from giving Drew a kiss of gratitude…or a kiss of lust. There would be other times for that and for the wine.
---
August 2020 - I'm pleased to see there has been 5000 views of this February 2018 story. As a first effort story I'm extremely pleased but at less then 850 words I wished I had combined all the chapters into a single longer story. Perhaps someday I will.
In the mean time I invite you to read my newest story, The Avon Lady: “Ding Dong, Avon Calling”. Working on a final draft I sense a sequel would be a logical thing.
Thank you for reading!
Regards, Dee
Ronnie stepped from the dressing room and back into the main convention room where the pageant was to take place. Drew remained in the dressing room.
Ronnie gathered with the other contestants near the stage podium and received the obligatory briefings, pageant rules and completed the required forms and releases. Glancing around at the other 15 – 18 contestants Ronnie checked out the competition. All were in basic girl garb but without makeup & heels. After all this was to be the first cut. Lads that didn’t meet a basic believability of passing as a woman were thanked and excused. Ronnie felt sad for those that were thanked and excused by pageant officials.
And then there were ten.
Ronnie was happy but a little nervous that he was to be in the finals. Several of the “girls” were very believable and had mannerisms that suggested they weren’t amateurs. They carried themselves differently than those that were excused.
The remaining contestants were told to change back to their normal men’s clothing and return for a second round of testing in one week. The next round required the works; makeup, heels, accessories and so on.
Entering the dressing room Ronnie changed clothes and stored his ‘costume’ in what looked like an over sized purse. Drew was nowhere to be seen. With a last glance into a floor length mirror Ronnie threw his bag over his shoulder and headed to the elevator to the parking garage.
Just as the down elevator dinged open Drew appeared from a nearby hallway. “Hey Ronnie, congratulations for making the first cut”. Drew stuck out his hand as if to shake hands and pressed a note and a tube of lipstick into Ronnie’s hand like you’d do with a head waiter if you wanted a better table.
“I dashed next door to Sephora and picked you up a good luck charm. It matches your complexion perfectly and is light enough shade that you can wear it during your daily activities or when ‘when the mood suits you’ as you said.
Ronnie stammered out a ‘thank you’ and could feel the involuntary blush well up on his cheeks. Tentatively Ronnie asked “will I see you next week?” Flashing a winsome grin Drew said “Sure… maybe sooner. Read the note when you get a chance.” Ronnie grasped Drew’s note and gift a bit firmer.
As Ronnie stepped into the empty elevator Drew patted Ronnie on the back. Ronnie turned to face Drew and quickly asked in a rapid run on sentence “Are you taking the elevator? What color is your dress? Do you need any help with your costume?” Ronnie was surprised at his own boldness in asking.
As the door was closing Drew replied “No, I’ll catch the next one. By the way I could feel that you’re still wearing your bra”. The door closed and Ronnie found himself staring at his reflection in the polished brass doors. Ronnie exhaled deeply and visibly slumped in an effort to rid his tenseness of all that had transpired over the last two hours. Or was it three hours?
During the ride down to the garage Ronnie tried to make sense of what had transpired, where some long suppressed desires and urges had come from. He knew they came from Drew but why? Drew had stirred him in a way that made his pulse rush.
The elevator door opened and Ronnie pushed his deep thinking to the background for now. Opening his car door he placed his shoulder bag of clothes onto the floor of the rear seat and slid into the front seat. Still a bit unnerved from the day’s events Ronnie tried to insert the tube of lip stick into the ignition. “Damn!” he thought. “I got to slow down and relax my brain”.
He exhaled and found his car key. Ronnie inserted the key but did not start the car. Instead he paused awhile and looked at his new tube of lipstick. Removing the cellophane wrapper Ronnie opened the tube and ran it out with one practiced motion. The color WAS perfect. And it smelled very nice. Looking first over one shoulder and then the other shoulder Ronnie made sure there was no one nearby. He reached up and adjusted the rear view mirror.
With familiar precision Ronnie slowly applied the lip color. He pressed his lips together as he always did and made a low smacking sound. The lipstick was, indeed, a perfect shade. He retracted the lipstick and replaced the cap. He read the color on the bottom of the tube. ‘Honey Blush’. “I must make a note of this” he thought. He placed the tube in his shirt pocket. The sensations were subtle but they were there none the less. He felt a familiar but not unpleasant stirring in his groin. There also were those far away ‘desires and urges’. Desires, thoughts and urges closer to his consciousness than they had ever been before.
Ronnie was about to put the car in reverse when he remember the note. He stared at the note lying on the passenger seat and picked it up. “I gotta read it sometime” he rationalized. The note seemed to crinkle loudly as he opened it. It read “I’m pretty sure I’ll be having a wardrobe malfunction pretty soon and I’m sure I’ll need some help and you offered. Call me.” Drew’s phone number and address were listed. Ronnie smiled. And the stirrings he was feeling grew stronger.
“Oh my God… what have I done!” Ronnie thought. He backed out of the stall and exited the garage. As he drove towards home his mind was racing. He was gripping the steering wheel intensely. After almost running a red light Ronnie tried to relax, took a deep breath and loosened his grip on the wheel.
Just before getting home Ronnie stopped at his favorite grocer. He spent more time than planned but selected three bottles of wine. He had a Chardonnay, a Riesling and a Merlot. The sales clerk greeted him and commented that Ronnie seemed in a very good mood. Actually the clerk said Ron looked perky. There was no mention of his Honey Blush lip color.
Ronnie got home, locked the door and put the wine in the refrigerator. He then changed into a special kimono silk bathrobe he fancied and perched himself on the couch in front of the TV. He has some very serious thinking to do. And it involved a lot more than the pageant. “Where are these desires, urges and thoughts coming from? And why does Drew make me smile?” And those sensations were of concern in a pleasant sort of way. “I just might wear my special baby dolls tonight” he thought. He smiled again and reached over and applied another application of his Honey Blush “chap stick”. Oddly enough the pleasant sensations came back. In truth the feelings popped up.
It had been a rough night for Ronnie following the events at the pageant as his subconscious kept wrestling with long repressed memories. Ronnie leisurely stretched and tried to recall his dreams and decipher their meaning. He yawned again and remained in the warmth and comfort of his bed while staring blankly at the ceiling.
Ronnie recalled being in elementary school and playing after school at his friend’s house. The name Josh came to mind. Yes he recalled it was Josh and his sister Lucy who were both a couple years older than him. They often played together. Nothing wrong with that he figured.
Then he recalled how they would dress up and pretend they were singing in a band, dancing and acting like they were big rock stars. It was an all girl band. More memories jumped to Ronnie’s forefront. He recalled that Lucy always insisted that they all dress up in skirts and tights to ‘get into the mood’. Nothing extravagant or too risqué but girly enough for what they were doing.
As he recalled the playacting only lasted for a couple years before Lucy moved on to other forms of play. Lucy discovered boys and other interests so the trio became a duet. Josh and Ronnie liked the karaoke and dancing to rock and roll. It continued to occupy their play time and it was fun.
Both boys eventually grew tired of the thick, warm tights. It was Josh that found that pantyhose were lighter than tights and would let you dance a lot easier on the wood floors. And it was Josh that also found that wearing panties enhanced the experience of the pantyhose. They made a good girl band.
It wasn’t long until Josh found some of Lucy’s cast off outfits that really made them look more authentic. A skirt, a short dress, maybe a cute blouse, short shorts, few bracelets… whatever was easy and made them look girly. It all added to their act. They practiced dancing with each other and the pantyhose made them glide easily around the room. And Ronnie fell in love with his feminine side. Especially the clothes.
Their play dates always took place when the parents were away or at work. Josh began locking the bedroom door. “Just in case” Josh said. “We don’t want our folks to think we’re sissies”. It sounded reasonable to Ronnie who was a couple years younger than Josh.
Lucy was a non factor and would come and go whenever she wanted. She thought that Ronnie and Josh were cute in a funny sort of way. She even suggested some songs and dance moves which the boys would sometimes include in their act. And it was Lucy that suggested they try a dash of lipstick to make the boys look more girly. Occasionally she’d paint their toe nails. “Nobody will notice because of your socks”. The smell of the polish was intoxicating to Ronnie. It was their personal secret. As Ronnie lay in bed certain things began to make sense.
Ronnie swung his feet over the side of the bed, straightened his baby dolls and slipped on his kimono house coat. He slipped into some warm mule slippers with a two inch heel. Ronnie drifted into the kitchen and retrieved his morning coffee. With a cup in one hand and the morning paper in the other he made his way to the couch. He sat down and curled his feet under himself in a natural but feminine manner. His odd dreams and emerging memories put the newspaper on hold. He began staring vacantly to nowhere in particular and let his mind wander some more.
There was a time…
There was a time when he and Josh were slow dancing in panties and pantyhose when Josh stopped. Josh dropped one hand down and gently cupped Ronnie’s penis through the nylons and panties. “Ronnie, have you ever noticed how nice it feels when you rub yourself over your panties and nylons?” Josh ran his hand up and down Ronnie’s crotch. Ronnie stood frozen as the sensation engulfed him. It felt very smooth and it felt very nice. It was very exciting in a new sort of way.
“Do you like the way this feels?” Josh asked. “God yes!” Ronnie exclaimed. “It feels like nothing I’ve ever felt before”. Both boys noticed that a significant bulge had begun to build in Ronnie’s panties. Josh was also looking a little lumpy in the groin. The nylon pantyhose rubbing on the panties which in turn stroked his penis was indescribable. It was mesmerizing. And it was addictive. “I can make it feel even better Ronnie but you have to rub me too. We’ll do it together”. With little hesitation Ronnie began caressing and slow rubbing Josh’s panty clad penis. Josh changed it up a bit by gently grabbing hold of Ronnie’s firmness. Ronnie followed Josh’s lead. Josh’s penis was so slippery through the two materials. Both of their young penises were firm and wanting. It was an exhilarating sensation. A magical throbbing was beginning to build in both boys.
Josh softly whispered “Ronnie this gets even better”. Josh increased the speed of his up and down stroking of Ronnie and Ronnie also began gliding his hand more quickly on Josh. The panties and nylons made it smooth and easy. Both boys were beginning to pant and slightly wiggle with some unknown but building anticipation. A sudden increased grip by Josh made Ronnie also exert a firmer grip on Josh's cock. They exploded simultaneously in a wave of extreme mutual bliss and cum. Life at that moment was heavenly. It was shortly after this life changing experience that Ronnie began to secretly wear panties and stocking on a frequent basis.
Ronnie the adult snapped back to reality. He found himself breathing more heavily. The memories were causing an involuntary arousal. So this is where those forgotten feelings and impulses began! Ronnie went for a fresh cup of coffee, returned to the couch and continued in his reverie of introspection. There’s more to this whole thing Ronnie thought. His mind drifted back in time.
Needless to say there were frequent repeats of Ronnie and Josh’s new ‘dance’ moves over the summer. Having to wash out their panties and stockings was a small price to pay for such pleasure. Both boys acquired their own sets of each item. It would be unbearable to have to do without.
Towards the end of summer while doing their special ‘slow dance’ Josh hugged Ronnie and said “I’ve found something even more pleasurable. Bill showed me. But first we start with our slow dance. OK?” Ronnie nodded okay. They had only danced for a few minutes and both were very rigid. Josh asked “Are you ready?” Ronnie again nodded his ok and quietly said “yes”.
Letting go of Ronnie Josh dropped to his knees and carefully slid Ronnie’s panties and pantyhose down to Ronnie’s ankles. Ronnie’s penis was pointing toward the ceiling. “Don’t move. I think you’re really going to like this.” Josh instructed. And with that Josh tenderly grasped Ronnie’s erect penis. Josh looked up at Ronnie and then, to Ronnie’s great surprise, Josh slowly sucked his penis into his mouth. Again Ronnie froze.
The warmth of Josh’s mouth combined with the firm grip of Josh’s lips made Ronnie see stars. His knees almost buckled. And then the sensation and feelings got better as Josh began dragging his tight lips slowly up and down Ronnie’s rigid penis. An occasional swirl of Josh’s tongue around the head of Ronnie’s penis was pure heaven. And then the firm downward glide of Josh’s snug mouth to the base of Ronnie’s penis followed by the firm lip grip on the upstroke was more than Ronnie could handle. Ronnie thought he could feel the tiny bumps on Josh's tongue. He erupted mass amounts of what he knew was cum into Josh’s mouth. His world shook.
But Josh didn’t stop. He swallowed! Josh briefly stopped and produced a tube of Lucy’s lipstick. It was a darker red maroon shade called ‘Cherries in the Snow’. Josh applied a liberal amount of the lipstick to himself and began repeating the smile producing cock sucking process again being sure to leave rings of color up and down Ronnie’s rigid cock. One ring was at Ronnie’s base, another was mid shaft and for a finale Josh applied some more lipstick and left a kiss imprint on the tip of Ronnie’s penis. “Look down Ronnie at what I left you. That’s something you’ll never forget. It’s a beautiful thing”.
Josh went back down on Ronnie’s shaft for a few more runs. Ronnie’s next eruption resulted in a lesser amount of sperm but with the same great feeling. Josh slowly stood up giving Ronnie’s penis a loving stroke of goodbye. Pulling Ronnie close, like a slow dance, Josh kissed Ronnie on the lips and expelled some of Ronnie’s cum into Ronnie’s mouth. By reflex Ronnie swallowed.
“What the hell was that?” Ronnie said loudly. “And why did it feel so damn good?” Josh started to pull up Ronnie’s panties and hose and replied “Bill says it’s called a blowjob. Not sure why because there isn’t any blowing going on. Did it feel good?” “It felt damn good but why the hell did you slip some of my cum back into my mouth? What’s up with that? And why the lipstick? ” Josh casually said “There are several reasons. First I like to mark territory, second the cum doesn’t taste that bad and third it makes us cum brothers. That’s very special. And it also gives you an interesting souvenir. You’ll get an additional thrill when you try to soap the red rings off your pecker. It’s a win-win. It also serves me as a goal to attain by showing me how much of your rod I was able to make love to. See how low YOU can place a love ring on a cock. It isn’t that easy. Besides it acts to keep my lips from chaffing. That is what Bill did to me and he’s a senior. Next time we dance you get to do it to me. OK? Promise?” Ronnie hesitated a moment, looked into his friends eyes and then quietly said “Okay Josh”.
“Be sure to wipe my lipstick off your mouth. It’s looks nice on you but it's noticeable. Before you do that lick your lips and see if you can taste yourself Josh advised”.
Adult Ronnie snapped back to the present. He found himself lightly trembling. Ronnie’s repressed memories and desires and weird dreams now had an explanation. Ronnie went for yet another cup of coffee. Things were starting to make sense. The source of his desires and urges were becoming clearer.
Back on the couch again Ronnie went back to pondering his past as he sipped his coffee. As he recalled Josh and Ronnie only did their slow dancing and panty stroking a few more times and then Josh and Lucy’s parents got a job transfer out of state. Ronnie was given Lucy’s hand me downs clothes and undergarments before the move. Luckily or unluckily, depending on your view point, Ronnie never kept his promise to Josh. Perhaps this was a deep seated regret that was messing with Ronnie’s head. It was an opportunity lost. Hmmm… Ronnie thought “Maybe Drew is my new Josh”?
Ronnie rose from the couch and walked over to the kitchen table. His car keys were there and so were the lipstick and wadded note that Drew had given him yesterday…the note with Drew’s phone number and address. Ronnie stared for a minute or two and then reached down and picked up the note.
Previously
Ronnie arose from the couch and walked over to the kitchen table. His car keys were there and so were the lipstick and the wadded note that Angel (Drew) had given him yesterday at the pageant tryout…the note with Angel’s (Drew’s) phone number and address. Ronnie stared at it for a minute or two and then reached down and picked up the note.
Chapter 4 – Do you want to dance?
Before Ronnie unfolded the note that Angel (Drew) had given him yesterday he picked up the gift lipstick. ‘Honey Blush’. Opening the tube he gave it a sniff which made him smile. “What a pretty fragrance” he thought. Extending the lipstick he put a small slash of it on his wrist. Indeed, the color was good for him. He then walked to the hallway mirror and carefully applied the ‘Honey Blush’ to his lips. He pressed his lips together to spread the coverage better. It looked and felt very nice. “I must remember to thank him.” He would use the wine as an appreciation indicator too. Ronnie used his hands to arrange his hair and blew a kiss to the girly face in the mirror.
Opening the note he re-read it: “I’m pretty sure I’ll be having a wardrobe malfunction pretty soon and I’m sure I’ll need some help and you offered. Call me.” It followed with his phone number and address. There was a PS that Ronnie had overlooked yesterday. “My name is Andrew and some people call me Drew. Please don’t. I hate that nickname. My friends call me Andy. My closer friends call me Angel. I hope you like the Honey Blush”. Ronnie reflexively smiled while his pulse went up a notch or two also.
Ronnie took the note and stuck it on the refrigerator with a Hello Kitty magnet for easy retrieval. The question became ‘should I call him?’ Taking a quick glance at the wall clock he was glad it was only 9 AM. They day was young! There was plenty of time for adventure. And there was the pageant he needed to prepare for. He was having second thought about participating: a $25 entry fee for a $200 gift card for the winner. It hardly seemed worth the effort. All that just so he could get ‘girly’ for a day.
Ronnie decided he’d give it some thought while he showered and got ready for the day. As he was turning on the shower he was glad he had a new set of peach colored tap pants with a matching camisole.
When he was almost done with his shower Ronnie grabbed his razor and quickly re-shaved his legs and armpits. He was an expert and was soon done. He was almost done when he decided to give his crotch a shave too. It had been several weeks. The act of pube shaving made him grin and feel pleasantly naughty. “You never know” he reasoned.
Stepping from the shower Ronnie quickly dried his body with a large towel but pat dried his legs. He then applied some moisturizer for good measure to his legs and a lesser amount to his pubic area. It always felt so nice.
Although his hair was only shoulder length Ronnie dried it and shaped it into a basic pixie style. A spritz of hairspray helped to hold the look. He applied his Honey Blush lipstick again, put on his kimono and mules and headed toward his phone. He felt a need to make the call. As he sat to make the call his mouth felt dry and his pulse was more rapid than usual. He opened a bottle of water, took a swig and sat down and made the call.
It took four rings before someone answered. At ring three Ronnie almost hung up out of nervousness. “Hello?” said the male voice on the other end of the call. “Is Angel there please, this is Ronnie”. There was a brief silence before the response. “Yes, this is Angel.” There was a relaxing tone in Angel’s voice and it made Ronnie’s relax a bit. “Oh my God, what do I say now?” Ronnie thought. “Yes, it’s Ronnie”.
The voice on the other end chuckled softly and said “We’ve already established that. How are YOU?” Ronnie composed himself and said “You were right, Honey Blush IS my color. Thank you again. Er… what are you doing today? You said you may need some help. You know, with the pageant”. Again his words all ran together. Ronnie hoped his voice sounded normal.
“I was just thinking about the pageant and could use some help with a few things. Not sure what to wear. You know… the usual stuff. Would you like to come over? I can make us a nice snack if we get hungry. It would be fun.” Angel said. With no hesitation Ronnie said “Yes, I’m free today. When’s a good time to arrive?”
“Five minutes ago would have been nice but since it’s only 10:30 now but how does 1 PM sound to you?” Angel said. “That sounds perfect. It’ll give me time to get my things together and stop for some pantyhose” Ronnie responded.
Angel paused a bit and said “When you go for your pantyhose make sure they are least 15 to 20 denier. We’re not into burlap covered legs in this house” he joked. “Be sure to get sheer Sun Tan or Skin Tone with nude toes. They will match your skin tone. If you’re feeling a bit trampy you might pick up a black set too. Control tops will help to keep your front flat. I noticed you were developing a bit of crotch bulge while I was adjusting your bra the other day. And not to be too pushy, bring your earrings”.
“What are you talking about? Earrings!?” retorted Ronnie. “I saw the tiny holes when I was hooking your bra. And they’ve been well used. I was standing right behind you, remember?” Angel said.
“Oh…. THOSE earrings” said Ronnie. “Well, I have to go now. I’ll see you in a couple hours”. Angel ended the call by saying “I’m looking forward to seeing you again. Bye for now”. Ronnie put the phone down and wondered what he was getting himself into. After another sip of water Ronnie got up and went to prepare for whatever was going to happen. It should be pageant related, right?
His shoulder bag still had his pageant gear from yesterday. He just needed to augment what he already had. He tossed in an extra bra, another tap pant and a “real” pair of panties. Just in case.
Ronnie put on his low profile A cup bra and then pulled on his new camisole. He then slithered into the matching tap pants. Both were a light peach color. There were no hose to put on since he was going to buy some later. He pulled on his good semi-skinny jeans which hid his panties and a white t-shirt that hid his peach camisole which helped hide his bra. This was his usual mode of operation.
Ronnie selected a nice dress shirt, buttoned it up and he was ready to go. He stepped up to the bathroom vanity mirror for a last look. Opening his jewelry box he took out a pair of dainty gold ball ear studs and expertly inserted them into his lobes. Ronnie noticed and retrieved his favorite anklet from the jewelry box. He rolled down his left sock and attached the feminine gold chain around his ankle. “Nice touch” he thought. It was another concession to his fem side.
Just before leaving the bathroom Ronnie applied a coat of his new Honey Rose “chap stick”. He did his lip smacking routine and then paused to think. Did he have everything? No he thought. He opened a drawer that had a variety of cosmetics, nail polish, etc. He ratted around for something special. He saw his special item in the rear of the drawer. He reached in and pulled out a different tube of lipstick.
Popping the cap off the lipstick Ronnie expertly twisted it out and gave it a whiff. Very nice color he thought. It was a dark red maroon lipstick. He closed his eyes for a moment and images of elementary school Josh popped into his mind. And so did the image of a lipstick kiss mark left on the tip of a special body part of his. Indeed, it was beautiful thing.
Ronnie retracted the red lipstick, put the cap back on and put the gold tube in his pocket. You can never be too prepared he reasoned. Before leaving his apartment Ronnie grabbed the three bottles of wine and put them in a pretty canvas carry bag designed for four bottles. “Angel has to like at least one of these wines” he figured.
The drive to Angel’s took about an hour primarily because Ronnie HAD to stop for his pantyhose. That took awhile. Macy’s always takes time. He bought three pair including a black pair. On impulse Ronnie also picked up a cute underwire demi-bra that was on sale. It came with a couple of removable “enhancer” pads. What the heck. Why not? Since he was already at the department store he also picked up two bra extenders. They can come in handy.
During the remainder of the drive Ronnie was thinking. “Angel is at least 3 or 4 years older than me. He looks as if he’s about 24 to 28 years old. I wonder where he learned his feminine ways? How does a man know so much about women’s things? And WHY is he interested in me?” Ronnie shrugged and continued driving.
Ronnie’s cell phone quickly led him directly to his destination. Angel’s place was a single story older home set back from the curb about 25 feet further back than his neighbors. Combined with the well established boxwood hedge that surrounded the house it created a comfortable zone of privacy. It was an older neighborhood and all the homes were well maintained.
Ronnie turned into the driveway and pulled forward to an apparent parking area close to a front porch. He turned off the engine and sat awhile to calm his nervousness. His nerve level was higher than normal. He dried his sweaty palms on his pants. He took a deep breath and exhaled slowly. Before opening the car door Ronnie freshened up his lipstick that Angel had given him.
Ronnie grabbed his pageant shoulder bag, the three bottles of wine and the Macy’s shopping bag with his recent purchases. With bag over his shoulder he walked toward the front door, locking his car via his key fob out of habit.
The porch was a covered one with two lounge chairs, a porch swing, and two side tables. Each table had a scented candle. It looked comfortable and inviting. Shifting his bra bag to his other hand he rang the doorbell and took a half step backwards. Ronnie was feeling a bit tense.
In less than 30 seconds the door opened and there stood Angel. He was wearing a short red satin waist long (and obviously feminine) dressing robe. It had a lot of humming birds on it. Ronnie noticed that Angel was wearing pantyhose. They clearly showed below the hem of the robe. Up top it looked as if Angel was wearing a boring man’s t-shirt. The total image looked good to Ronnie.
“Nice to see you again! You made good time. Please come in. It looks as if you brought some things” Angel said. They did the obligatory Hollywood hug and back rub. Angel playfully plucked Ronnie bra band. “Oh, I notice that you’re wearing a bra under your shirt. Nice touch.” Angel exclaimed. “Yes, whenever I get the chance. That’s what I do” replied Ronnie.
As he stepped into the living room Ronnie smiled nervously and looked around. The place was tastefully decorated. The dark hardwood floors brought back elementary school memories. “It’s nice to see you again too. Thanks for the invite. I brought the wine I spoke about and a few other items. I also brought the 20 denier pantyhose” Ronnie announced. “Perfect!” Angel replied.
“Have a seat. Let me have the wine and I will pop one open before we begin” Angel said. “I’ll pour us a glass and be right back. I’ll place your bags in my spare bedroom. Make yourself comfortable. The sofa is very comfortable. And your ear studs are a nice touch. They make you look prettier. I have a spare set of gold hoops that would look even better. We should give them a try.” Angel went to the kitchen.
Ronnie looked around the place and decided that the sofa was the optimum place to sit. It faced a large bay window that had a good view of the front yard. The window had lovely thick room darkening draperies. The single drape draw string was a gold braid that had cute tassels. Ronnie sat down at the far right of the sofa ensuring he had easy access to the coffee table and an end table for his wine.
Angel returned in a short time with a tray with two glasses and the bottle of Chardonnay. There also was a selection of cheeses, crackers and salami on a tray. Angel had opened the bottle in the kitchen and he filled their glasses in short order. Angel sat down next to Ronnie and handed him a glass of wine. “Here’s to the pageant” Angel said. They clinked their glasses, took a sip, and relaxed back into the sofa. Ronnie took another sip and placed the glass on the nearby coffee table. His wine glass clearly had a lipstick mark on it. Angel followed Ronnie’s gaze, saw the lipstick smudge and smiled.
“It appears you liked the Honey Blond, eh? I told you it’d look good on you. It even looks good on the wine glass” Angel joked. “Wait until you see how the sheer nylons make your legs look”. Ronnie blushed and laughed lightly at the humor of it. “Sorry” Ronnie apologized and replied “Your legs look very nice in those nylons. I noticed they are nude toe style. They look… eh… sort of sexy. What shade are they?” Ronnie picked up his glass and took another sip of wine in a nervous reflex.
Moments of silence passed as they both stared out the front window. It was a relaxing view.
Angel moved a bit closer to Ronnie and said “Make yourself at home. I was just getting dressed when you arrived. I need a few minutes to finish and will be back soon. There are some magazines on the table and a large coffee table book on The History of Cross-dressing. The TV remote is on the lamp table next to you if you want. I’ll be back soon. I have an extra room if you care to change now.” Angel turned and went to his room.
Sitting alone Ronnie took another deep breath, exhaled and took another sip of his wine. He thought he felt the start of a buzz. Ignoring the Vanity Fair and Glamour magazines he picked up the large coffee table book and began flipping through the pages. It was filled with many interesting photos of pretty men in pretty clothes in various stages of being clothed. Ronnie wasn’t focusing on the pictures… he was just flipping pages and trying to relax.
It didn’t seem long before Angel returned. He was wearing a form fitting LBD that looked a bit loose in the shoulders, a classy brunette wig, and perfect makeup. His eyes were delicious looking; his eye lashes were long and beautiful. He wore a dainty gold ring, a necklace with a cross and dangling ear rings. Angel also had a small jewelry box in his hand.
Sitting down on the sofa Angel moved closer to Ronnie. Angel opened the small box and displayed gold hoop ear rings that were about three inches in diameter. He filled their wine glasses and did another wine glass clink with Ronnie. They both took a drink. Not a sip but a real thirst quencher amount.
Putting his glass down Angel said “These will look very nice on you. Do you mind if I replace your studs with these hoops?” Ronnie hesitated a moment. Taking another sip of the Chardonnay, he looked directly at Angel and said. “Sure. Let’s give it a try.” Angel slid even closer and reached for one of Ronnie’s ears.
While Angel was removing the backing of Ronnie’s ear studs Angel said “I think you did a good job with your pixie cut.” Angel set down one stud and backing onto the coffee table and reached for Ronnie’s other ear. Ronnie turned slightly and slid closer to Angel to make it easier for the earring swap. It sort of tickled in a curious way. A few seconds later the remaining stud was also on the table.
Angel brushed a few stray hairs behind Ronnie’ ears, leaned closer and expertly inserted the hoops. Ronnie heard them click closed. Angel got both hoops in place with little effort. “There now” Angel said. “They do look prettier”. He sat back for a better look. “Very nice” he proclaimed. “Shake your head a bit and feel how they brush your cheeks. Here’s a mirror. Take a look”. Before looking into the mirror Ronnie thought “Having another person touch your ear lobes is pleasantly sensual”. Ronnie shook his head for effect and had to agree that they felt nice; like a reminder of his emerging femininity.
Ronnie reached over and put his hand on Angel’s nylon clad knee and gave it a rub. “Thank you for the use of your ear rings. They look and feel nice”. He gently shook his head again. Ronnie took another sip of his Chardonnay and stood up, placing the glass back on the table. “I think I’d better get into my outfit. I’ve been having doubts about the pageant” he stated. “It seems like a lot of effort with little in return other than having a chance to be girly for a day”.
“And you like to be girly don’t you? So do I” Angel said. It wasn’t a question it was a statement.
Before he went to the spare bedroom Ronnie had another sip of wine and took off his shirt and white t-shirt in the living room. He wanted Angel to appreciate his peach camisole. You could easily make out the outline of Ronnie’s ‘secret’ bra under the cami. Ronnie entered the bedroom with his bag of things and closed the door. He was definitely feeling the wine.
Emptying the contents of his bags on the bed Ronnie sat down at the nearby vanity, slumped into a relaxed position and closed his eyes for a couple minutes. He stood, took off his trousers and anklet and then removed his slinky tap pants and thought “Let’s not make this a project”. Standing nude in front of the vanity mirror Ronnie took a quick glance at his nudity. He saw that his penis was not as flaccid as he had hoped.
Opening the new package of sheer Sun Tan pantyhose he easily rolled them up his legs as he looked into the mirror. He remembered to put on his gold anklet. He replaced his peachy tap pants enjoying the way they felt as they slid up his nylon encased legs. The sensation was awakening a certain pleasant lust. Ronnie added a 20 inch long black half slip over his stockings and tap pants. “Excellent! “ he thought, Glancing again into the mirror Ronnie could still see the beginning of his crotch bump that Angel had mentioned. He was very glad he had bought the control top style pantyhose. They did help. Angel’s advice was correct.
Ronnie swapped out of his bland A cup undercover bra replacing it with his new underwire demi-bra that was a B cup. It also was black. Instinctively he pulled his spare flesh from under each armpit inwards and upwards to create a bit of cleavage. He left the enhancer pads in the bra. He did his little bra shrug to align things. He was about to pull his cami back on but decided against it. He grabbed his version of a Little Black Dress that he’d worn at the pageant tryout yesterday and stepped into it with practiced ease. He knew he was going to need help again with the rear zipper.
He found his black pumps with 2 inch heels and slipped into them. He then sat back down at the vanity and reached for his lipstick. Just before applying a coat he noticed he had the wrong tube. This was not the time for the dark red maroon lipstick. Reaching back into his bag he found his Honey Blush and expertly did his lips. He looked into the vanity mirror and pressed his lips together as usual. He found the Macy’s perfume sample of Cashmere Mist that he had been given and put the smallest of dab behind both ears and another dab low on his throat. “Less is more” he thought.
As Ronnie sat at the vanity prior to going back to the living room he could hear that Angel had turned on the stereo and was playing some soft music. Ronnie did his deep breathing routine twice, grabbed his hair brush, BOTH lipsticks, stood up and opened the door. He felt like he needed a little more wine.
As Ronnie entered the living room he saw that the drapes had been closed. Angel was busy lighting a couple of scented candles. Hearing the clip clop of Ronnie’s heels Angel turned to greet his guest. “My, don’t you look pretty. It looks as if you changed into a more suitable bra. That’s a pretty anklet. You look very passable”. “Thank you. A compliment from a person with such an obvious appreciation and knowledge of femininity is appreciated. HOW did you become so informed?’ Ronnie asked. “Oh, we can discus that a bit later. Care for some more wine?” Angel asked.
Ronnie nodded his head and clomped towards the sofa and wine. “I like the choice of your music. I used to dance to this type of music with a friend when I was in elementary school. We used to practice a lot”. He took another sip and sat down.
“Isn’t it fascinating the way things keep coming around in life. What was her name?” Angel asked. “His name was Josh. We danced on hard wood floor like these. Sometimes we played at being in a band… a girl band. His sister used to help” replied Ronnie.
Angel raised an eyebrow at Ronnie’s admission and smiled as he gazed at Ronnie. “Well that certainly explains a lot of things, doesn’t it? Come closer so I can do up your zipper”.
“To cut down on the noise of those heels on the hard wood you may as well kick them off for now. You can see I don’t have mine on” Angel said. Ronnie agreed and kicked them to the corner. He took the again offered wine and had another gulp. Ronnie moved closer to Angel, turned his back and asked “Please zip me up”.
“Please zip me up” Ronnie thought. Isn’t that how this all got started? He giggled aloud and waited for Angel. “By the way Angel the baggy shoulders on your dress tells me that you need a hand with your zipper too”.
Yes, it all started with a zipper. And what goes around comes around is a pretty true axiom.
As Angel was about to pull up the dress zipper up, not un-expectantly, he announced “bra fit time” and reached around to cop another feel of Ronnie’s nipples. Yes, they were hard again. After a few quick caresses with his thumb and fingers, with a gentle pinch of each nip, Angel zipped Ronnie’s dress closed. Ronnie was appreciative. He pulse rate increased.
Angel sat back a moment and said nothing for awhile. “Ronnie, you smell so delectable. What is that aroma?” Turning to face Angel Ronnie managed to say “Cashmere Mist. I was hoping you’d find it attractive”. “Yes, attractive. I find it attractive”. On impulse Angel leaned forward and gave Ronnie a soft kiss on his cheek. It left no outward mark. Inwardly it left a mark on Ronnie as that little kiss rekindled old urges, desires and memories.
Angel broke the ice by picking up their wine glasses and passing one to Ronnie. “Here’s to the pageant! Drink up.” Looking at each other they clinked their glasses yet again and both finished their wine in one gulp. “I’ll need to open another bottle. But that will have to wait until later” Angel said. “It’s your turn to zip me up and get rid of the sagging dress shoulders you noticed”.
Ronnie sat quite for awhile staring into Angel’s eyes quivering inwardly at the prospects of events that might happen. “Sure Angel just turn around and back up a little”. Angie scooted closer to Ronnie. A Victoria’s Secret tag marked Angel’s satin bra. Ronnie playfully snapped the bra band and quipped “I see you’re wearing a bra”. He paused to give Angel’s back a gentle caress from the armpits to his waist. Leaning forward Ronnie whispered as sultry as he could into Angel’s ear “You know this calls for a bra fit test”.
Reaching around from behind and above Ronnie brought his hands to the target area cupping and caressing Angel in the most seductive way. Ronnie was in no hurry. Angel made a low gasp but made no move to leave. Having gotten the green light Ronnie grabbed both breasts and did the nipple dance with his thumbs. Angel moaned but did not move. Ronnie thought Angel breasts had more mass than normal. It didn’t matter. They felt good to him. And it felt like the right thing to do.
Purposely breathing warmly into Angel’s ear Ronnie gave Angel one last titty rub and leaned forward and kissed Angel tenderly behind her left ear leaving a faint mark. “Your bra fits fine and you feel fine. Very fine” Ronnie whispered. A moment later and Angel’s dress was fully zipped. Still facing away from Ronnie Angel said “And what you did felt perfect. Combined with the scent of your perfume your touch was driving me crazy”. They both giggled like school kids… like elementary school kids thought Ronnie.
Turning to face Ronnie Angel looked into Ronnie’s eyes and leaned forward and kissed him on the lips. Not just a peck but a real kiss with a touch of tongue as they pulled apart. Ronnie’s heart was pounding. Life at that moment seemed wonderful. Embolden by the moment Ronnie reached over and brought Angel close and returned the kiss in a more passionate way. The flavor and melding of their lipsticks was erotic.
Angel broke off the kissing by saying “I best get some more wine. It looks like we can also use some more crackers”. Angel stood up, looked at Ronnie and said “I think we both need to fix our lipsticks”. Looking into the mirror Ronnie agreed. He needed a break if for no other reason than to cool off a bit. As Angel turned toward the kitchen Ronnie thought he saw that Angel was sporting a crotch bump. Ronnie was in the same situation. It was not an unpleasant feeling.
By the time Angel returned with the wine and crackers Ronnie was fully repaired and sitting on the sofa flipping through the big book again enjoying the photos and music. As Angel set the tray down he queried “Are you really thinking of bailing out of the pageant? If you’re only doing it to be girly for a day there are other options you know”. Filling their glasses with more wine Angel said “I think I could help you with some things. You really need to do something with your eyes and lashes and your nails are marginal at best”.
Being a bit offended with Angel’s comments Ronnie quickly spoke up. “What makes YOU such an expert? I’m doing okay”. Angel said “I didn’t mean anything by my comments. I apologize. It’s just I think you can do better. What makes me such an expert? Have a sip of wine and I’ll explain”. Angel and Ronnie both picked up their glasses and in a Hollywood moment they entwined their arms holding the wine glasses, pulling their faces closer together, and while looking in each other’s eyes they took a sip. They put their glasses down and sat back into the sofa.
“I may not be an expert” Angel said “but check out who the author of that 100 page book is. It’s me. Combine that with years of walking the walk rest assured I know a few things.” Ronnie checked the title page. It was true. Angel is the author. This explained many things. “I’m sorry Angel I guess I’m a bit tense. I’m lucky to have met you”. The music continued and had become a bit more up tempo. Angel had made a good party disc it seemed.
Ronnie noticed Angel’s pantyhose clad foot tapping time to the music. Ronnie had some more wine and said “This is a good song to dance to care to give it a try?” Not skipping a beat Angel said “Sure!” and stood up and began to dance. Ronnie was a second behind. The made it through two up tempo songs and began laughing at their own efforts. Their nylons made it easy to glide around.
They took a brief break, caught their breath and started dancing when the next song launched. Ronnie had surprised Angel with his dance moves. The next song was a slow dance, the music in which you hold hands and touch your partner type of song. They both stopped and it became quite.
Angel broke the ice and asked Ronnie “May I have this dance, miss?” Ronnie nodded and demurely took Angel’s hand letting him lead. They glided around the room in a firm but tender embrace. It was nice. The music, by chance, remained slow and Ronnie found himself laying his head on Angel’s shoulder as they danced. Angel was so gentle and comforting.
Another slow song began and their slow dancing continued. Angel looked down at Ronnie and gave him a passionate kiss. Not entirely knowing what he was doing Ronnie dropped one hand and pressed it on Angel’s groin. There was some distinct firmness there and it seemed to be growing. The dance continued and Ronnie continued to slowly stroke Angel's growing bulge.
Angel began to reciprocate to Ronnie’s delight. The control top pantyhose were not doing the job for either of them. Ronnie stretched up a bit and planted a loving kiss on Angel’s lips. Grabbing Ronnie tighter Angel began a full on make-out session that was leaving them both panting and wanting. They danced close to the sofa and coffee table. Ronnie stopped dancing even though the music still played on.
Not knowing where his boldness came from Ronnie began to really stroke Angel’s bulge, tracing Angel’s penis up one side and down the other. Ronnie used his thumb to better stroke Angel’s cock head while maintaining eye contact. Angel was busy too but used the palm of his hand to create a lovely hardness in Ronnie’s groin. No one was moving. Just kissing and stroking each other. For Ronnie the combination of the tap pants, panty hose and half slip was insanely perfect.
Without asking Ronnie picked up a pillow from the sofa and put it on the ground at Ronnie’s feet. Ronnie’s heart was racing and his blood was hot. Ronnie dropped to his knees and looked up into Angel’s eyes and said “Can you do us a favor and pull up your dress”? Angel was slightly trembling and said “Sure baby, anything for you”. Angel grabbed the hem and pulled up his dress.
Ronnie noticed that Angel was wearing pantyhose only. There was a damp circle of pre-cum in the middle of Angel’s pantyhose. His penis looked divine under the hose. Grabbing each side of the hose Ronnie savored pulling them down in a slow manner. Angel’s cock sprang free and was pointing toward the ceiling. It was about seven inches long and just about the best circumference. Ronnie blew his hot breath onto the shaft and got the twitch he had hoped for. Ronnie was glad that Angel was circumcised and that he was completely shaved smooth. Ronnie was glad that he had shaved his pubes too before driving over.
It had been many years since Ronnie had gotten this treatment from Josh and he was a little unsure as how to proceed. Ronnie kissed the tip of Angel’s penis and removed a pre-cum drip with his tongue tip which resulted in another twitch from Angel. It must be like riding a bike. You never forget. Angel was watching everything.
It seemed to Ronnie that both of their cocks got harder as Angel watched. Ronnie took a deep breath and made a first run with his tongue from the base of Angel’s cock to the tip taking in another drip of pre-cum. Pausing for a second Ronnie made a downward lick and then quickly moved to engulf the cock head giving it several swirls with his talented tongue. And then Ronnie stopped. Angel looked down with an unmistakable look of shock and disappointment.
Maintaining eye contact but remaining silent Ronnie smiled coyly. Ronnie reached over to the nearby coffee table and retrieved a tube of lipstick… a tube of red maroon lipstick. Still kneeling Ronnie used the mirror on the table to apply several thick coats. “Keep the dress up” Ronnie requested.
Lowering his head Ronnie continued giving his first blowjob. He made a snug ‘O’ with his lips and kept a firm grip. He locked his lips about half way down the shaft tightening his lip grip and slowly pulled his way up the shaft dragging and swirling his tongue as he went. He let the cock pop free and looked for a ring of color. It was there! He looked up to Angel and made sure he had seen it. Ronnie smiled and went back for more. Sucking, swirling and licking; making sure to maintain a good lip grip in each direction.
Ronnie came up for air, looked at Angel and took another gulp of wine. He also reapplied his lipstick. He wanted to mark territory. He had just gone down the now slippery shaft again when Angel gently inserted his fingers into Ronnie’s hoop ear rings. Angel used the hoops to guide Ronnie to where he found the better blowjob sensations… like reins on a young horse. Nice touch Ronnie thought. Up and down, a bit to the left, a bit to the right. Angel pulled the ear ring hoops up indicating that he wanted more attention to his cock head. Ronnie thought he could feel the veins in Angel’s cock. It all was very tactile. Ronnie had never felt so horny or hard.
Angel released hold of Ronnie’s ear rings giving Ronnie full control. Immediately Ronnie made a plunge for the base of Angel’s clean shaven cock and pressed his lips more tightly around the shaft. At the top of his upwards sucking he let the cock pop free again. It surprised Ronnie that the cock release actually made a popping sound. And there it was; a dark red ring of lipstick at the base of Angel’s cock. Josh would have been proud! Ronnie could feel the sweet slime that was Angel’s pre-cum. The taste was mild.
As long as he was cock free for the moment Ronnie took the opportunity to apply yet another coat of his red ‘chap stick’. Figuring it was time to bring the blowjob to a climax Ronnie made another run and tried some new moves. He lightly grabbed Angel’s balls and carefully gave them a gentle stroking. He moved his head around differently, made the cock head rub the roof of his mouth and tried jacking Angel’s shaft with a free hand as he continued to lick and suck. Angel began doing some face fucking thrusting moves.
Ronnie could sense something happening; something new. It felt like Angel’s cock was enlarging and beginning to throb. Ronnie increased his head bobbing, sucked a bit harder and more firmly gripped the base of Angel’s cock. There was a sudden and intense explosion of warm sperm! It gushed and squirted four of five times. Ronnie heard Angel cry out in ecstasy. Ronnie knew better than to stop and look up. And he was glad the taste wasn’t bad.
Ronnie changed the pace of his sucking and slowly coaxed the last of the sperm out the penis tip using his lips as a circular squeegee making several slow upwards runs on the shaft. He swallowed most of the loads retaining a small amount in his mouth. He had licked the cock clean. Ronnie could see Angel’s penis start to go limp.
Ronnie looked up at a very pleased Angel and stood up. He hugged Angel firmly and gave her a solid kiss on the lips and expelled the remaining sperm into Angel’s mouth. Angel didn’t resist and he didn’t swallow which surprised Ronnie. Instead Angel swirled his own essence around in his mouth first and then swallowed. Ronnie took note. Something new for sure.
Angel stood there in pure ecstasy. He managed to croak out “My god! Thank you Ronnie! And where in hell did you learn what you just did to me?” Ronnie licked his lips for the last of the pre-cum and smiled. He said “Wait. There’s more”. Ronnie picked up his tube of Honey Blond lipstick, applied a coat and then bent over and kissed the head of Angel’s dick making sure to leave a cute lip imprint of a different color. Angel’s cock twitched again. Ronnie then stood up and pointed at Angel’s new lip print. “See that?” Ronnie queried. “That’s a beautiful thing. And we’re sperm buddies now”.
Ronnie had the presence of mind to pull up Angel’s pantyhose. He smoothed them out a tucked Angel’s cock back where he found it giving it a final rub. Ronnie also pulled Angel’s dress back down and into place. They both retreated to the nearby sofa and plopped down. They were truly spent... for the moment. There was another clinking of glasses and another swallow of wine.
Ronnie reached over and grabbed Angel’s hand. He stroked the back of it gently and gave the back of his hand a kiss. Looking at Angel he said “Have I told you I have doubts about going through with the pageant?” Angel laughed. “I told you that you can be girly here any time you want. I can show you things and take you places that don’t involve travel. Besides I want to do up your eyes”.
“I feel bad about not giving you any relief” Angel said. “Whenever that ‘relief’ does happen we need to use the sofa or a bed. It was getting difficult for me to keep standing I wanted to keel over and writhe on the floor. I felt bad for your knees even though you had a pillow”. Ronnie let out a quite laugh. “I agree” he replied. “In fact it sort of sucked” he quipped. They both began to giggle at the humor of it all.
Still sitting side by side on the sofa and stroking each other’s nylon clad legs Ronnie asked “What did you mean that you can ‘show me things and take me places that don’t involve travel’”? Angel replied “Let me fix your eyes first. We’ll talk about the rest a bit later”. Giving Ronnie an impassioned kiss on the lips Angel stood up, grabbed Ronnie’s hand and guided Ronnie to Angel’s bedroom. There were eyes to be done and some relief to be given. And just maybe there might be new places and things that Ronnie should see and experience.
Previously
Still sitting side by side on the sofa and casually stroking each other’s nylon clad legs Ronnie asked “What did you mean that you can ‘show me things and take me places that don’t involve travel’”? Angel replied “Let me fix your eyes first. We’ll talk about the rest a bit later”. Giving Ronnie an impassioned kiss on the lips Angel stood up, grabbed Ronnie’s hand and guided Ronnie to Angel’s bedroom. There were eyes to be done and some relief to be given. And just maybe there might be new places and things that Ronnie should see and experience.
Chapter 5 – Are your ears ringing?
They entered Angel’s bedroom and Ronnie made a detailed mental inspection. It was a large room, maybe 15 x 20, with a large master bathroom with a walk-in shower, a separate tub, dual sinks and dual vanities. The walk-in closet seemed enormous to Ronnie. One side was obviously for male clothing while the other side was occupied by all things feminine. Dresses, skirts, blouses, belts, purses, and shoes were in perfect order. There was also a sit down vanity and mirror.
Angel opened a built in set of drawers to proudly display his lingerie. Silky and slinky. Panties, garter belts, nylons, shape ware, a wide variety of bras, heels, belts and purses; some items Ronnie didn’t recognize… the usual! One drawer had the lifelike breast forms that Angel had spoken about yesterday. Ronnie picked one up and felt its realistic weight and feel. Much better than the bird seed falsies that Ronnie had made. Ronnie placed it back. One drawer had a variety of sex toys and tubes of what had to be lubricants.
Ronnie made a mental note to get a garter belt and a few real stockings. They looked as if they could be a lot of fun.
The main part of the Angel’s bed room consisted of a queen sized bed, matching end tables and lamps and yet another sit down makeup table that was loaded with cosmetics. Very impressive Ronnie thought. There were two large windows that had pretty window treatments. Both windows provided a pleasant amount of natural light. An exterior boxwood hedge provided additional privacy. The list of ‘goodies’ went on.
Angel steered Ronnie to his makeup table and instructed Ronnie to remove his LBD and have a seat. “Have a seat, baby doll. There’s some wipes on the table so remove your makeup and lipstick. You’re about to have a makeover”.
Ronnie complied, carefully placing his dress on Angel’s bed. He sat down wearing only his pantyhose, anklet, tap pants, half slip and bra. He gazed at the large amount and variety of cosmetics, nail polish and “tools” of the trade like tweezers and eye lash curlers. The quantity of mascaras, eyeliners and eye shadows let him know that Angel was very serious about eye makeup.
Ronnie took one of his deep breath calming exercises, grabbed a makeup remover tissue from a pretty crystal dispenser and began to wipe off his lipstick. He usually never wore makeup. Angel was nowhere to be seen. There was some activity in the kitchen that he could hear and Ronnie could smell the pleasant odor of coffee being brewed. With his lipstick removed Ronnie sat in his lingerie and waited.
Ronnie took this break in action and scurried to the rest room, sat down and peed. He finished, stood up, blotted his penis tip and pulled up his pantyhose, tap pants and slip. He flushed, rinsed his hands and returned to the vanity bench. He didn’t have to wait long.
Angel appeared with a tray that offered coffee or tea and a variety of cookies and wafers. “Here you go, baby.” Angel said. “I needed to work through the wine buzz. Help yourself”. Angel placed the tray nearby. Ronnie opted for a basic Bigelow tea and a couple of cookies. He hadn’t realized how much he needed them. Very refreshing and much needed.
Angel pulled up a chair near Ronnie and as they munched and sipped tea they made small talk. It was obvious to Ronnie that Angel was studying his face and eyes. Angel’s eyes darted from Ronnie to the various cosmetic on the vanity. Angel finished his wafer and announced “Let’s give you a basic makeover as it’s getting late”. Angel leaned forward, stroked Ronnie’s cheek and gave him a quick kiss making sure there was no leftover lipstick or cosmetics.
Angel moved his chair closer and proceeded to give Ronnie an over view of what he was going to do. “First I’m going to apply a general primer hat makes foundation glide on more easily, then we’ll do some foundation, followed by a concealer, if needed, a bit of a bronze, and some blush. Your cheek bones demand some blush. Next we’ll do your eyebrows and get them shaped and under control. We’ll complete the session with my favorites; eye shadow, eye liner and mascara. It’s easy! Lipstick is last. No need to be concerned. Just relax into it”. Ronnie looked a little overwhelmed and took another sip of tea. He closed his eyes and faced Angel.
Angel went to work with well practiced efficiency. Ronnie liked the feel of the soft brushes, sponges and the smell of the cosmetics in general. A crotch bump was beginning to make itself known. The lump did not escape Angel’s notice. Angel smiled but ignored it for the time being.
Angel took great care with Ronnie’s eyebrows thinning and shaping them as needed. They took on a definite feminine arch. Angel decided on a smoky grey eye shadow and finished with black eyeliner. “Open your eyes baby doll as it’s time for your mascara”. Coating both upper and lower lashes several times Angel showed Ronnie an eye lash curler. “This won’t hurt and will make your eyes stand out.” After crimping Ronnie’s eyelashes Angel selected a reddish lipstick that almost matched the love rings that Ronnie had placed on his cock earlier. Angel thought his choice of lip color was ironic. “I’m done! Take a look”.
Ronnie turned to face the vanity mirror and could hardly break eye contact with the beautiful face that stared back at him. “Wow!” Ronnie exclaimed. “This is amazing! You were correct that I needed to do something with my eyes”. As he looked longingly into the mirror Ronnie fell in love with the image. His growing erection became more obvious. It was a situation that Angel could not ignore very much longer. “So what do you think doll face?” Angel asked.
Ronnie reached over, hugged Angel and gave him a passionate kiss on his lips. “I love it! I look so much prettier and feminine. Thank you. I really need to pay attention to my eyes. It certainly makes a big difference.” In return Angel lovingly grasped Ronnie’s obvious hard on through his slip, tap pants and pantyhose and began slowly stroking his cock. “Stop by some time and I can give you some tips. I’ll even toss in a bra check.” Ronnie smiled, closed his eyes and leaned backwards a bit.
Angel had to admit that Ronnie’s multi layers of silkiness did make cock stroking more exciting. Before things literally got out of hand Angel said “It gets better. Remove your tap pants, pantyhose, anklet and stand up”. Ronnie complied and stood there nude except for his black half slip for basic modesty. He sported a raging erection that begged for relief. Ronnie could hardly contain himself.
Angel brought out an eight tab black lace garter belt and wrapped it around Ronnie and hooked it closed. Ronnie watched but didn’t move. Putting a bath towel down on the vanity bench Angel handed Ronnie a pair of 15 denier black stockings. “Here you go baby doll sit down and roll them up. I’ll hook you up when you’re done”. Ronnie sat down and began rolling the silky stockings up his cleanly shaved legs. Each garter strap had a cute white bow where it met the stocking.
Before hooking the stockings to Ronnie’s garter belt Angel said “We have a problem. Step closer”. Looking into Ronnie’s eyes Angel grabbed Ronnie’s very, very erect penis, leaned forward and licked a pre-cum drop from Ronnie’s cock head. Ronnie’s eyes rolled back and he swooned and twitched in his own personal ecstasy. Ronnie realized the advantage of not wearing panties or pantyhose: easy access to your penis! What a brilliant idea.
Angel expertly attached each of the eight garters to Ronnie’s stockings taking time to ensure that each stocking and strap was perfectly aligned. This smoothing required a delightful ankle to crotch smoothing motion. Ronnie glanced into the vanity mirror. He almost had an orgasm as he saw the reflection. The tug of the garter straps was new and exciting. His raging hard on pointing towards the sky was so very naughty. He liked it.
Angel chuckled at Ronnie’s delight. “Step closer. It appears there’s another leak that requires attention”. Ronnie stepped closer and this time Angel did not lick the tip of his penis. Instead he gave Ronnie’s penis tip a kiss which removed the drip. And then Angel grabbed the base of Ronnie’s shaft and gently began slowly sucking Ronnie’s entire cock into his mouth, inch by inch, using a lot of tongue action. It was a beautiful thing.
Angel bottomed out and just as slowly began the slow upward suck withdrawal making sure to wet the entire shaft. Angel swirled Ronnie’s cock head and released it making the same popping sound that Ronnie had done earlier. And the dew drop was gone. Ronnie was enthralled.
Smiling at Ronnie Angel said “Come sit on the bed beside me baby doll”. Ronnie did not hesitate. Angel looked at the many lipsticks on his vanity and selected the same color that he had put on Ronnie. Color coordination was important to Angel. Making sure that Ronnie was observing Angel slathered on a thick coat of the pretty red color.
Announcing “It’s time to mark territory” Angel began a slow blowjob on Ronnie. There was no resistance or objections from Ronnie. Angel stopped briefly to inspect the lip rings he was leaving and to ask Ronnie to more fully get on the bed. Ronnie complied and laid back to enjoy the experience.
After a few more minutes of mouth action Angel asked “Remember when I said I could ‘show you things and take you places that didn’t involve travel’? In a lust filled gasp Ronnie’s said “Yes”. Smiling Angel said “Well lay back, bend your knees, keep your feet flat on the bed, close your eyes and relax”. Ronnie did what was asked of him. Prior to going back to pleasuring Ronnie Angel dipped a two of his right hand fingers into a jar of lubricant that was on the night stand.
Angel improved his position as to where Ronnie was laying, applied some more lipstick, leaned over and snugly gripped Ronnie’s penis just below the cock head with his lips making sure to leave a red ring. With a few swirls of his tongue Angels lips slowly slid down Ronnie’s shaft and left another red ring at the base of Ronnie’s shaft. ‘This should make him happy’ Angel thought.
Angel repeated the routine twice with a few variations. On his third downward run on Ronnie’s shaft Angel wedged open Ronnie’s legs slightly with his right hand just enough to be able to smear some lubrication around Ronnie’s rosebud of an anus. Ronnie made and involuntary full body twitch that popped loose his shaft from Angel’s mouth.
Straightening up from his task Angel brushed Ronnie’s cheek and said “Relax baby, I’m not going to hurt you, I’m going to take you to a heavenly place that doesn’t involve travel”. Ronnie took a deep breath, exhaled and laid back. Angel smiled, leaned over and kissed him on the lips making sure to run his tongue tip and spread Ronnie’s pre-cum back and forth on Ronnie’s lips. “Relax baby, it’ll all be OK”.
Grabbing Ronnie’s shaft with his left hand he went back to ‘The Blowjob From Heaven’. As soon as Angel started the downward slide with his lips he circled Ronnie’s sphincter a few more times with a greased finger liberally spreading the lube of his target. Angel then slowly inserted his middle finger into Ronnie’s ass making sure to fully coat both the inside and the outside. Angel continued with his shaft sucking and slurping and began sliding his well lubed middle digit in and out of Ronnie searching for his prostate gland. In a moment of boldness Angel slid two fingers in at one time. Ronnie gasped.
It was no more than three minutes of being finger fucked until Angel found his target. Angel was giving Ronnie’s prostrate a gentle rub and by sheer coincidence that on an upward suck Ronnie came. His cock throbbed once and sperm started gushing. Ronnie’s rectum clamped down on Angel’s fingers. Angel smiled and swallowed. Not a drop was wasted. There was that popping sound as Angel let go of his lip grip of Ronnie’s cock. Angel straightened up and looked down at Ronnie and enjoyed seeing him go through several aftershocks of pleasure. Ronnie finally opened his eyes and almost cried. It had felt so great, so new, so naughty and decadent. It was a beautiful thing.
Angel bent forward, kissed Ronnie on his lips and let Ronnie voluntarily suck his own cum from Angel’s mouth. Ronnie made a point of keeping his seed in his mouth awhile before swallowing. Angel looked down at Ronnie and brushed a strand of hair off Ronnie’s forehead. “There now, we’re ‘sperm sisters’”. Angel climbed onto the bed next to Ronnie and laid back. They both stared up at the ceiling in silence and let their breathing return to normal while holding hands.
Ronnie rolled over to face the vanity mirror. Angel immediately rolled over to spoon Ronnie. Angel unhooked Ronnie’s bra, removed one silicon breast form and began to absentmindedly trace circles around Ronnie’s nipple and do some gentle caressing. “Well baby doll, what do you think about what just happened? Did you like it?” Angel asked as he rolled over on his back.
Ronnie rolled back over too and said nothing for awhile. When he did speak he said “THAT was a beautiful thing. I never knew that an orgasm could feel that great. Thank you for taking me places that don’t need a car.” They both began to laugh. Ronnie turned his head and kissed Angel again just for good measure.
They laid in bed staring at each other for awhile when Angel said “I know the pageant has been worrying you a lot. You don’t need a pageant to feel or be ‘girly’. I think you should cancel out and come be girly with me. Let me make you more girly. You can be as girly as you want whenever you want. I know that with a little effort we could go out in public with no problems. And don’t forget I have a 100 page book that proves that I know how to make it happen. It’s loaded with photos, instructions and tips”. Angel gently pulled Ronnie’s face closer and gave him a passionate kiss as if to seal the deal. Ronnie kissed back.
Ronnie sat up, one of his bra cups was hanging down and empty. “I think you’re right. The pageant has been driving me crazy. I don’t need the aggravation. You ARE right. I can get girly without a pageant… with your help of course.” Angel nodded his head in agreement. “In fact I’ll call the pageant people tomorrow and tell them to count me out!” Ronnie announced.
Ronnie threw his nylon clad legs over the edge of the bed and sat up, his back to Angel, the tug of the garters felt erotic; a reminder of all things feminine. Without turning Ronnie asked “Will you hook my bra? It’s getting late and I need to be leaving in the near future.” Angel reached over and hooked Ronnie’s bra giving it a light snap to signal that it was hooked. Angel handed Ronnie the missing breast form and said “Keep these. Souvenirs’ of fun times are nice”. Ronnie inserted the form back into his bra, stood up and did his shoulder bra adjustment shrug. Everything was in place. Ronnie looked into the mirror and ran his fingers thru his pixie cut hair in an effort to look decent and broke into a wide smile. The dangling hoops looked great. Angel also exited the bed and made for the bathroom.
After Angel was done Ronnie went in and took care of business. Wearing the garter belt (without panties) made peeing so much easier. Just sit, pee and blot. He washed his hands and looked at the sight in the mirror in front of him: a pretty face, with beautiful eyes, which was wearing a garter belt and black stockings that had a penis hanging down. “Oh my god, what am I to do? I don’t want to ruin my eyes” he said aloud.
Angel entered the bath room and said “No problem. Leave your makeup on until you get home. I’ll send you home with tissues and makeup remover. It would be a shame to waste that look. You can keep the garter belt and stockings. Give me back the large hoop ear rings and I’ll give you a smaller set as souvenirs. And don’t be letting anybody but me be dragging your head around by the ear rings.” Both parties began to laugh loudly. It had been a memorable moment. Heck, it had been a memorable day.
Ronnie retreated to the spare bedroom and got squared way and packed. He did not put on his tap pants electing to wear only the half slip. It was short and had always tucked easily into his pants when he wore it to work. Not wearing tap pants, pantyhose or panties felt breezy in a decadently naughty sort of way. As he pulled on his trousers, sans underwear, he admired the lipstick rings on his dick. He smiled and was afraid he’d ‘tent’ his half slip.
Ronnie took a last look in the mirror and giggled. There, in the mirror, was a cute woman wearing a man’s shirt and pants. He made sure his new bra was barely visible under his cami. The last things he did were to apply his Honey Blush, smack his lips and dab on more Cashmere Mist perfume. He winked at the girl in the mirror and blew her a kiss of goodbye.
Looking around to make sure he hadn’t forgotten anything Ronnie removed the large hoop ear rings and exited to the living room sofa. Angel was already there with another tray of hot tea, finger foods and the smaller set of hoops. “Here take these hoops baby doll” Angel said as she clicked them in place in Ronnie’s ears. “Sit down for a few minutes and relax. You don’t have to rush off and the hot tea will be nice”. Ronnie agreed. Before he sat down Ronnie walked over and hugged Angle giving him a lingering kiss. Angel kissed Ronnie back and snapped his bra strap. “That’s what you do, right?” he laughed. They sat down. Ronnie put a bit of honey in his tea, stirred it, grabbed a cookie and sat back to let the tea brew a bit.
The living room curtains were open again and it was clearly getting dark. Ronnie sipped at his tea and told Angel” Thank you for an amazing day of amazing things. I feel relieved in many ways. The fact that I’m not doing the pageant is a relief and you relieved me in a way I never could have imagined”. They both giggled and flashed impish grins at each other.
Still seated on the sofa Angel looked seriously into Ronnie’s well made up eyes. “Let me give you some advice baby doll. Don’t let your dressing up make you paranoid and uncomfortable. Express yourself in any way you want. I think wearing an anklet, shaving your legs, maybe painting your toe nails or wearing some pretties under your men’s clothes is fine if it lets you get in touch with your fem side. And you must admit you definitely have a fem side which explains that beautiful scent you reapplied. Let your fem side out while you’re young and pretty enough to truly enjoy it”. Angel leaned over and gave Ronnie a brief kiss.
“Come over anytime but call first. You can leave a tooth brush and some girly things here if you want. You can always be girly for me. I may even let you wear the large hoop ear rings again. Maybe I’ll get you a house key”. They stood, hugged again and said goodbye again. Ronnie picked up all his bags, which included the makeup removal items, in preparation of leaving.
As Ronnie grabbed the front door knob Angel handed him a copy of his ‘The Art of Cross-dressing’ coffee table book. “Here, take this with you baby doll. I think you’ll learn a few things. I autographed it for you”. Ronnie opened the book and read “To a cute girl and a special sister. Love, Angel”. This called for another smooch and hug.
As Ronnie finally got the front door open Angel said “Next time we get together we need to work on your nails. They need help. AND make sure your toe nails are painted. No one will know. I slipped a couple shades that will look nice on you into your bag. And by the way pull up the zipper on your pants for god sake!” Ronnie glanced down and saw that Angel was right again. His zipper WAS open. But that was probably an acknowledgement that this whole day came about and was literally started by a zipper. It was the zippers fault.