Amber Fountaine stories contain sexually explicit descriptions of consensual sexual activity and are not suitable for reading by anyone under the age of 18, or anyone offended by reading such material. These acts include gay and bisexual activity as well as any combination of piss play, diapers, cross-dressing and other fetishes and perversions that may please the author's whims. The characters in these stories are fictional, but are mostly based on the author's true experiences, as well as the experiences of others he has met. Every attempt to conceal these identities has been made. These stories are placed in Nifty for the enjoyment of its readers and are not to be copied and/or distributed without the approval of the author.
"John's Journey"
by Amber Fountaine
John's journey began at "River Cliff Mall" when he was in high school in his junior year. Up until the previous semester, John had been taking gym and had never really paid all that much attention to the cocks of the other boys. But that afternoon, at the mall restroom, things had been different.
John had gone to the men's room to drain his bladder and had never given a thought to taking the urinal next to the older man. Then at some point while he'd been pissing, the man made a noise or spoke softly to him or something and John had glanced in his direction.
The man was slowly stroking a big, hard, man-sized cock and every time the man's hand reached the base, pulling the skin tight, the huge cock head seemed to swell even more and turn dark purple. John had been mesmerized by the sight and couldn't make himself turn away until the man had muttered, "Go ahead and feel it."
"Scared," hadn't been the word for it. John had damn near pissed in his pants in his hurry to get out of there. But that night, he'd jacked his own cock thinking about the one he'd seen and wondering what might have happened if he'd really done as the man said. He'd been pretty sure - no, positive - that they'd have had some sort of gay sex. He'd known instinctively that holding that man's big beautiful cock would have led to putting it in his mouth and sucking it and swallowing the man's cum - all those nasty, horrible things that he'd heard gay guys did together. And John wasn't gay.
He'd told himself that every time he jacked off and thoughts of that big-headed dick had crept into his mind. He'd told himself that every time he woke in the morning, his cock hard as a rock, after having had a dream about some man offering John a cock to play with. Sometimes those dreams had really upset John; especially when the man in the dream happened to be his dad or the man next door or one of his friends. Then, a few years later, he'd had the weirdest dream of all, and things changed in a new direction. It occurred when John was older, and thanks to the help of one young lady, had been much more experienced.
John hadn't been the handsomest of boys and while he'd dated some, he'd graduated from high school, still a virgin, and hadn't had his first sexual experience until he'd been in the Army for a couple of years. Her name had been Crystal - not too pretty and not too bright, but she had a great body and loved to fuck.
In some ways, especially for a young man on Private's pay, she was every man's dream. She didn't care if they went out anywhere or not. She'd been completely satisfied to stay home and fuck. So that's what John had done. Every moment that he could get away from post, and she wasn't busy, he'd gone to her apartment and they'd fucked. The only catch had been - and it was a small one once he'd gotten past the notion - Crystal wasn't completely satisfied until after John had eaten her out after they'd fucked.
For years prior to meeting Crystal, every time John had thought about that big-headed cock while jacking off, fantasizing that instead of running off, he'd had the courage to touch it, hold it, kiss it, put it in his mouth and suck it, like he was sure the man wanted, he'd wonder about the taste of cum. So each time his jack-off fantasy was of that big headed cock, John had told himself that this time, when he shot his cum, he was going to taste it just to see what it was like. But once he'd shot off and had a puddle of jism in his palm, those urges had vanished and he'd never done it. He'd tried tasting his pre-cum, and thought it sort of bland or tasteless. That big puddle he shot in the palm of his hand was another issue altogether. Down from his sexual peak after ejaculating, he'd never gone through with his plan to lick it up. He'd looked at it, tried to work up the courage, and each time had backed out and wiped his hand clean on a towel or his underwear instead. But at Crystal's insistence, he'd licked his cum from her pussy and discovered it was . . . different, but not bad.
From his point of view, he'd really had little choice, and he liked the aftertaste, once he'd gotten used to it. That lingering flavor in his mouth reminded him of Crystal's pussy and that would get him aroused again. He could even understand her attitude.
"Guys are so stupid about that," Crystal had told him. "You guys want me to suck your dicks and swallow your cum, but you guys are afraid to taste it. If you're afraid, I'll find another boyfriend."
So John had quickly gotten over his aversion, and soon thought nothing about it; even beginning to like it - when he was honest with himself. Still, it hadn't been the sort of thing he'd told his Army buddies about either. In a relatively short time he had even gotten to where if he hadn't had sex with Crystal for a few days and needed to jack off, he'd do it under the covers in the barracks, shoot in his hand, and then lick his hand clean. It made for a much nicer experience as compared to jacking off in one of the latrine stalls. What had seemed so difficult to him as a teen, had become commonplace once the line had been crossed. Then had come what he referred to as, "The Dream."
In the dream, he and Crystal had gone to a dance, had gone out to his car to fuck in the parking lot, and when John had pulled her panties down to eat her pussy, instead he'd found a cock that looked just like the one from the mall that had been in so many of his other dreams. He'd recently told Chrystal about that incident, so thinking she was pulling some kind of joke on him, John had sucked the cock until it filled his mouth with cum. That had made John wonder how Crystal had pulled off that trick, since a fake cock wouldn't be shooting out real cum, and when he'd looked up at her face, it wasn't Crystal any more, but one of his Army buddies dressed as a girl. Somehow they'd worked together to fool him and they'd swapped places. Crystal had still been there, watching through the car window, and began telling John that she'd always been sure he really wanted to suck some dick and she'd really done him a favor.
The cock from the mall had given John years of fantasies and dreams, but not like the, "Crystal with a Cock," dream had done. Most dreams were forgotten within minutes of waking up. This one he remembered vividly. Worse yet, over the next few weeks, the dream had returned and in various versions. In some, Crystal really had a cock. If he'd suck it and swallow her cum for her, the cock would disappear and he could fuck her pussy. In others, he'd pull off Crystal's panties, find a pussy and she'd tease him about being disappointed that she didn't have a cock. And in the one's that really bothered him, John was the guy that dressed as a girl and had sex with another man while Crystal watched.
Then another incident happened a few weeks later. Crystal had to work late, again. She'd previously given John a key to her apartment, so she'd told him to pick up some beer and pizza, and said that when she got home, she wanted him and the pizza both hot and ready.
Following her instructions, John had put the beer in the fridge, the pizza in the oven, and had gotten naked, planning to greet her at the door that way. Then he'd gone to the bathroom, needing to pee, and had found a bunch of her lingerie hanging on the curtain rod and towel bars. He'd looked at the lingerie, looked at himself in the mirror, and as he'd watched his cock stiffen, he knew what he was going to do. He'd seen Crystal wear the black lacy panties several times and when he thought about it, he was sure that the man he'd sucked in the car in his dream had been wearing an identical pair of panties. Without another thought, John had put them on and marveled at the feel and fit and the image of himself in the mirror.
What John had always liked about the panties was that they were made of two layers of material. The outer layer was black lace and the inner layer was shear black nylon. When Crystal wore them and he rubbed her pussy, the outer layer slid around on the inner layer and for some reason, they'd both found that exciting. So John had begun to rub his cock the same way and had found it to be even more exciting. Adding to the tactile sensation had been the visual image of his hard cock, very visible through the shear material, as he'd watched in the mirror.
Then he'd grabbed a yellow nightie off the curtain rod and slipped into that. It didn't exactly go with the black panties, but it had been the shortest of the three nighties hanging there and allowed his panty covered cock to be visible. That had been his goal. He'd fought the urge to jack off, knowing that Crystal expected him to be ready for sex as soon as she got home, but he hadn't wanted to take off the lingerie either. So he'd gone to the kitchen to make sure the oven was warm enough, but not so hot that it overcooked the pizza, popped the top on a cold beer, and damn near dropped it when Crystal had asked, "Is that for me?"
Unable to speak, John had tried to hand her the beer, thinking that's what she wanted. Instead, she'd grinned even bigger and pointed at his crotch. Because of the way he was dressed and the thoughts that had been on his mind, being caught red-handed - or in this case, red-faced - had caused his mind to stop working. It wasn't until she'd pointed at his panty covered crotch that he'd realized she was naked.
Somehow they'd gotten it backward. Normally when they had sex, he was naked and she'd wear one of her sexy nighties - at least for the first few minutes. His plan had been to greet her at the door naked and give her a minute or two to change into one of her nighties. Instead, he'd been so caught up in his first cross-dressing experience that he hadn't heard her come in. Then when she'd seen him in the bathroom in her nightgown, she'd gone in the bedroom and gotten naked. She was naked and he was in the nightie - backward of the way it usually went.
"You make a very sexy lady," she'd told him, finally taking the beer with one hand and using the other to put behind his neck as she kissed him, hot and heavy. When she'd finally pulled her tongue out of his mouth, she'd told him, "Glad one of my other boyfriends didn't stop by and catch you like this. I might have lost both of you."
He'd long suspected that Crystal saw other men besides him. The one time he'd tried to question her about it, she'd told him, "I don't talk about you to other men and I don't talk about other men to you. If you're not happy with that, don't let the door hit you in the ass on the way out."
So he hadn't commented on her remark, and after taking a couple of big gulps of the beer, she'd said, "Bedroom time sweetie. I've got a treat for you."
She'd spread across the bed, parted her legs, and raised her knees into the position she enjoyed most when he ate her. But when he'd started to take off the nightgown she'd stopped him. "You really look cute," she'd said, "And . . ." She hadn't been able to stop herself from giggling, "It's appropriate."
Everything considered, John had realized that he was more turned on than he'd ever been in his life. So he'd buried his face in her hot wet pussy and ate her the way she'd told him she liked best. He'd hit all the right keys, hummed the right tune while sucking her clit, and given her an awesome orgasm. When they'd cuddled together, a few moments later, she'd told him, "Damn, you're as good as a girl when you're dressed like one. I'll have to get you some lingerie of your own."
"I don't want to wear lingerie," he'd insisted.
"Are you certain about that? You can't tell me wearing my things didn't have you excited, and you sure seemed to enjoy the taste of Ed's cum - even more than usual."
Again he'd been too shocked to speak. He'd buried his head in her hair on the pillow so he didn't have to look her in the eye. Ed was her boss. John had met him, knew he was married, yet had long suspected that there was something more than work going on between Ed and Crystal. And he'd tried to ignore the fact that every time Crystal had to work late, she was always hot and horny and ready for sex as soon as she got off. He also had ignored the fact that her pussy was always hot and wet and - now that he'd learned to recognize the flavor - had sort of tasted like cum when he ate her at those times. He'd written that off to his overactive imagination, probably caused by that dream about Crystal having a cock.
Now he knew that for the last few months he'd been eating another man's cum. It wasn't like he'd really sucked a cock or anything queer like that, but it was worse - much worse in his opinion - than just licking up his own cum. Suddenly he'd known that he could never look her boss in the eye again. And sometime that night, he'd decided that he didn't want to see Crystal again either. Afterward, on many nights, while jacking off in his bunk, he'd regretted that decision.
Almost ten years had passed since then. John had gotten out of the Army, found a good job as a service rep, had gotten married, fathered a girl, and a few months back, he had gotten divorced. In that whole time, there hadn't been a week went by that John hadn't thought about his dreams. And a few times, he'd had newer versions that were just as wild and wanton. Sometimes he was dressed as a girl making love to a girl, as he had with Crystal that one time before they broke up. Other times - more like most of the time - he was sucking another guy's cock either dressed as a girl, or the other guy was dressed as a girl. It had been a growing fantasy.
In addition, many times in the six years he'd been married, he'd worn some of his wife Cheryl's lingerie to jack off when she wasn't home. He'd only done it once in front of her. On their honeymoon, he'd dressed in one of her panties and nightgowns to surprise her. He'd been hoping she might like it, as Crystal had, but instead she'd told him it was disgusting and he'd never done it in front of her again. If she'd known he was doing it behind her back, she'd never said anything. She'd also thought it disgusting when he tried to eat her pussy after they'd fucked.
"I'm not clean," she'd told him. "Why would you want to do that? Are you queer?"
He'd assured her he wasn't and never tried that again. Sometimes he wondered how he'd ever made it through six years.
For his thirtieth birthday, after years of fantasy and an unsuccessful marriage, John had made a vow. Fantasy time was over. Somewhere, somehow, he was going to have sex with a man - and more than anything, he wanted it to be a man dressed as a woman. He was afraid that if he tried it the first time with a more masculine appearing man that he might back out. But the `chick with a dick' idea that had been part of his dreams and fantasies for years seemed like the best place to start.
Perhaps he'd had that in mind when he'd taken his current position that required him to be back out on the road so much. While John was anxious to cross that line, he took his time, buying a small supply of lingerie that he could wear as he pleasured himself and day dreamed about what might happen when he met the right man. For more inspiration, he had a small but growing collection of she-male porn
In the meantime, he also pursued women, dating often, and after several in a row had turned into one-night-stands, he had to admit that what he'd really been looking for - hoping for - was a guy, dressed so convincingly as a woman that it had fooled him. In thinking about it honestly, he realized that most of those women had been larger; women that most men wouldn't have gone for. He was sure he knew the reason. Not wanting a totally impersonal tryst with someone he met over the internet, and not knowing where to find a she-male any other way, he'd been hoping that one of those masculine appearing women would turn out to be a man. Then a motel magazine pointed him in the right direction.
He just happened to notice a story about a "Pride Celebration" and how as part of the gay festivities, two bars had challenged each other to a "Drag Race" with guys dressed as women having a foot race in high heels, running around a local park. John wrote down the name of the two clubs, pinpointed their locations, and went looking.
He was sure the first woman he picked up was a guy dressed as a woman. It wasn't until they were back at his motel, about to get undressed and climb in bed, that she told him, "I usually don't do guys. I love other women. But sometimes I want some real dick." That soliloquy had almost caused John to lose his erection. It was just his luck to pick a lesbian that liked a little cock now and then.
The next time he was in the area, he tried the other bar and almost didn't stay long enough to meet Rhonda. He'd never been in a club that was so loud. He found a seat at the bar, around the corner and almost up against the wall. It was as far from the bandstand as he could get. There was an older man sitting between him and the wall at the end of the horseshoe bar and that guy didn't stay long either. The club, at least for that night, had a live band that had taken the old adage, "If you can't play good, play loud," to a new level. In this case the level was well over 100db. John would have followed the old guy out the door, but he heard the band say something about one more song and then they'd break and John had spotted a couple of `girls' that he thought might be men. So he ordered another drink and made a quick trip to the men's room. When he got back to the bar, there was a woman sitting where the old guy had been.
John couldn't believe his luck. This one was even prettier than the two he'd spotted. Too pretty maybe - he began to wonder is maybe she was a real woman. Then he noticed she was drinking a beer. Every real woman he'd ever known drank wine or some kind of fancy drink. So he guessed that `she' was a guy that still liked his beer, no matter how he was dressed. But before he could summon the courage to talk to her, the band started back up and he didn't feel like shouting over it.
At one point, the band all screamed, strummed their guitars, or whatever they were doing, and the noise was so deafening that John winced. In the short moment of comparative silence that followed, he heard her giggle at him and turned to her. "Not funny," he told her. "They're too damn loud." "I agree," she answered before going back to sipping her beer. Then a few minutes later, she had to almost shout in his ear, "Want to go somewhere else?" John had almost laughed, thinking that while this guy could look gorgeous dressed as a woman, he still drank beer like a man and picked up guys like he was still a guy. "Where to?"
She shrugged. "Anywhere that's a little quieter."
John briefly thought about suggesting his motel room, but instead mentioned the name of the other bar that he'd visited a couple of weeks back, getting a smile and nod. Fortunately he knew the town well enough that he didn't get them lost as she followed him in her car.
At the other bar, John learned her name was Rhonda, which he was sure meant that when she wasn't dressed as a woman, he probably went by Ron or Ronald or something like that. The thought that he was finally going to make this happen had him incredibly excited and she noticed when she let her hand drop into his lap. When she felt his hardness, she gave it a squeeze and whispered in his ear, "I may not be as good as some of your other lovers, but I love to suck cock if you'd like to give me a try."
He smiled at the thought that she'd gotten the impression he was a regular at those gay clubs and was about to tell her, "yes," and that he wanted to suck hers too, but the waiter interrupted. They both declined another round, finished what was in front of them, and continued their conversation in the parking lot.
As they clung to each other, enjoying the warm summer air and their even warmer bodies pressed together, John marveled at how lifelike her breasts felt in his hands. He'd been learning a lot about the guys that cross-dressed from the internet, as his own assortment of lingerie grew. He hadn't as yet had the nerve to walk in and buy anything from a retail store, and had made his purchases online. So he knew that some of the more lifelike bra pads were expensive. As he continued to grope her tits as they kissed and made small talk, standing beside his car, he decided he would find out what kind she'd gotten and where, as he had a growing fantasy of one day being able to do the things she was doing.
But that was a long way off, considering he still didn't know for sure that he'd be able to get over the stigma of another man's cock in his mouth and enjoy that forbidden act. He'd become aware that girls like Rhonda liked to call their cocks, "Clitties," or some other cute name and he was more than ready to see how he did with Rhonda's clitty before he made plans to dress fully as a woman so he could pick up a man.
Again he laughed to himself. He was making the same mistake as Rhonda. He'd have to stop thinking like a man if he went that far. He wouldn't pick up a man - he'd allow a man to pick him up. Rhonda looked gorgeous to him, but she still had some work to do in that area.
"Am I your first fag-hag?" she asked, as they cuddled and cooed and debated which car or both they should take back to his motel.
Not being that attuned to the alternative lifestyles, John assumed "fag-hag" was another nickname for guys that dressed as women to have sex with men. So he smiled and admitted he was a virgin in that respect.
"The quicker we get back to your motel, the quicker I can make that history," she said, rubbing his cock with one hand.
Again she followed him, neither wanting to leave their cars in the lot as this was promising to become an all-night - and maybe longer - affair. It was Friday night, she'd hinted that her weekend was free, and he'd told her he could stay in town a couple of extra days with no problem. It was a thought that brought smiles to both of their faces as they drove the few miles back to where John was staying.
As before, John was filled with anxiety; eager and yet afraid of the consequences of what they were about to do. He knew at the moment he was as sexually aroused as he'd ever been and that he'd have no problem sucking Rhonda's clitty and looked forward to his first mouthful of cum. He just had to be sure he didn't let her make him cum first. How he'd feel about it afterward . . . well he'd just have to wait for afterward to find out. But at the moment, spending the whole weekend in the sack with a cross-dressed man seemed like a good idea.
Rhonda's smile was caused by her assumption that John was a virgin with women. She hadn't had a virgin since her high school sweetheart, who was now her ex-husband. Most of the guys she'd met through her ex, or at the club where he hung out now, were gay, but had tried girls in their teens, and were willing to give it one more try with her just to be sure they'd made the right decision. One more try was fine with her. She'd just wanted to get laid, didn't like macho guys at all, and wasn't looking for another relationship. But there was something different about John that she'd picked up on right away. She wondered . . . that cock in his pants had felt real . . . but could it have been a dildo? Was John really JoAnne pretending to be a man? Her cousin Emily had taught her how much fun two girls could have in the sack and there'd been several other girls and women since then. If John did turn out to be JoAnne . . . well, it would be sort of a disappointment, but not a huge one. She really did love sucking cock and the reward of a mouthful of cum, and that she couldn't get from a woman with a strap-on, but she'd yet to meet a woman with a strap-on that wasn't willing to give Rhonda all the orgasms she could handle. Men didn't tend to think that way.
Once in the room, John tried to get his hand up her dress immediately after the door shut and she stopped him.
"You already told me we have plenty of time. Let's enjoy this." Then she began to slowly undress him. When she found the camisole under his dress shirt, she wondered again about his being a `JoAnne' and immediately went for his belt buckle and fly. Seeing the lacy panties almost made her stop to let John, or JoAnne take the lead, but then she saw that cockhead peak over the waistband of the panties and the little drop of pre-cum already forming there, and knew it had to be the real thing. They didn't make dildos THAT lifelike.
From the aggressiveness of her actions, John was certain that Rhonda needed more work on how to act feminine. In the better light of the motel room, he marveled again at what a beautiful woman Rhonda made when she dressed enfemme, but again thought about how she seemed too masculine in her actions and attitude. For a moment he'd thought this cross-dressed man was going to rape him. She kissed like a woman but thought like a man.
She interrupted his thoughts to ask, "Do you wear these things all the time?" Rhonda had him down to just the camisole and panties.
"Usually just at home. Tonight was the first time I've worn them out."
She smiled. "What's the special occasion?"
He returned her smile and said, "You."
That earned him a kiss that developed into a passionate embrace. Considering there was no way he could have known ahead of time that he'd meet her, she thought that was a very nice thing for him to say. Then she pushed him back across the bed, hooked the waistband of his panties behind his balls, and over his protests of wanting to do her first, proceeded to give him that blow job she'd promised, licking and sucking and almost missing the first squirt of his jism; he responded so fast. One thing she'd learned from her ex and his friends was that gay boys - or the mostly-gay men that she'd been to bed with - like to share their cum. So instead of swallowing his load, she held it in her mouth and moved up to kiss him.
John realized immediately what she'd done as her sperm-coated tongue dueled with his. Up to now, Chrystal had been the only woman he'd ever known that would do that, but he imagined that gay guys did it all the time. And that reminded him of his real reason for being here with Rhonda in his room.
While still kissing, John attempted to undress her, pulling her blouse out of her skirt and reaching behind her to unhook her bra. When she stopped him, he thought he'd done the wrong thing. He'd done what he would have done automatically with a real woman, but realized that with Rhonda, once that bra came off, she would look more like a he than a she. When she quickly stood up beside the bed, he thought she'd re-hook the bra and maybe just take off her blouse and skirt.
Unbuttoning her blouse, she told him, "Better let me do this. I need to wear this stuff home and you seem to be in a real big rush to lose that virginity."
He smiled and nodded and then was amazed when her breasts appeared. She must be on hormones or something, he thought. "Those look real," he muttered.
She laughed. "They are real - what did you expect?" Then before he could answer, she knew. "Oh shit! You thought I was a guy didn't you. I should have known when I saw you admiring Bobbi-Lynn and his friend. Rhonda," she said aloud, speaking to herself, "You are a dumb-ass."
When he realized she was putting her clothes back on, he jumped up to stop her. "Wait - please. I don't want you to go. I . . ."
"What did you mean about being a virgin? She asked, pausing for a moment. "Have you ever been with a woman?"
"Not as beautiful as you." In a pleading voice he added, "I'm glad you're really a woman."
She looked at him steadily, watching his eyes and facial expressions and knew he wasn't some slick talking guy trying to say all the right things. She studied him a moment longer, began to smile, and then broke into a laugh. "Okay, let's start over. I love the taste of your cum in my mouth, but I could really use another beer."
There was a small refrigerator under the sink and John had five beers out of a six-pack left in it. He flew across the room to get her one. By the time he got back to her, she'd taken off her blouse, which was a good sign, but had re-hooked the bra. Then when he handed her the beer, she took it with one hand and pulled his panties back up over his cock with the other.
"Let's put that away for the time being and start from the beginning."
He sat on the edge of the bed, and she took the arm chair nearby. He began to give her a brief outline of his life to date, but with her urging for detail, she'd finished her beer, even though she was sipping it, before he finished his narrative.
The only question she asked when he'd finished was, "Do you still want to try sucking a she-male dick?" When he nodded, she told him, "I could use another beer."
So he got her another and him one too. While he was up, he heard her leave a message for someone on her cell phone, telling them to call her. Then she gave him a much shorter version of her life.
Robert Lynwood Harrison had been her high school sweetheart from the time they started dating in the 10th grade. She'd known back then that Bob was different, but she really liked that difference. He wasn't pushy and trying to get in her pants at every chance like most of the other boys. Even before they started having sex, she'd known he had a friend in the neighborhood that swapped blowjobs with him, and that Bob like to dress up like `Bobbi' when he did it. So when they began having sex, she encouraged him to wear her clothes and always tried to give Bob the best blow job possible. "I thought he looked cute in my clothes and I wanted him to come to me to get his dick sucked and not his friend Tim." Eventually Tim had faded from Bob's life and she thought that would be the end of it.
But he'd continued to dress as a girl and she found that to be a lot of fun. She'd experimented with sex with her cousin Emily and had liked it and Bob or Bobbi was like having a boyfriend and girlfriend all rolled into one at the same time. She told John how at their wedding, they'd worn matching lingerie and that Bob had dressed as Bobbi for most of their honeymoon. They'd been deliriously happy, like most newlyweds for a few years, but when she began to press him to start a family, he told her he didn't want to talk about it just yet. Finally he'd confessed to her that he'd been having gay sex behind her back for years; even before they'd married. He'd told her the real reason he didn't want a family was because he thought he was gay.
She told John that she'd been hurt by his confession, but then thought maybe it was something they could share. To her amazement she discovered that watching her husband sucking cock and getting his ass plowed really made her hot. For a couple of years, he'd get dressed up on Friday night, they'd go out with one of their mutual male friends, come home for a three-some, and then she and Bobbi would fuck all weekend. She thought it was great, at least at first, but after a while, she realized she was being cut out. Bobbi would pay all his attention to the other guy and when the guy went home, Bobbi went back to bed - to sleep.
So a couple years back, she and Bobbi had gotten an amicable divorce, had remained friendly, and that since then, Bobbi had set Rhonda up a few times with his gay friends that wanted to try sex with a woman. It had gotten Rhonda a reputation as a fag-hag among the gay crowd. "And that's fine with me," she concluded. "I'm a photographer and often have to work with male models. Believe me, the gay models are MUCH easier to work with."
Then she sat back in her chair and stretched her arms. Her movement caused her skirt to ride up and John could see the tops of her stockings and a garter strap that he thought he'd noticed earlier. He'd toyed with the idea of getting some for himself, but that was another line to cross and so far he hadn't pushed himself over it; maybe after this weekend.
"See something you like?"
Caught staring, he told her, "Your stockings. They're so much sexier than pantyhose."
"Then how come you're not wearing any?"
He shook his head. "Don't have any." Then he grinned sheepishly and added, "Yet."
She stood in front of him, returning his smile. "Take off my skirt and you can see better."
Without hesitation, he slid off the bed, dropping to his knees in front of her. But just as he reached to her waist to loosen her skirt, her cell phone went off on the table next to him and it was almost as if he'd set off some sort of security alarm. He jerked his hands back, causing her to laugh.
"Phone call silly," she told him. "Would you hand it to me please." When he did, she said, "Now finish what you started."
As she began talking, he went back to removing her skirt, unbuttoning and unzipping and letting it fall to her ankles. As he held it so she could step out of it, she told whoever she was speaking to, "Just a second."
Then she grinned down at him as she stepped out of her skirt and asked, "Sure you still want to suck your first cock? I can make it happen."
There was something about the way she'd said, "your first cock," that gave him pause. A couple of times he'd speculated to himself as to why all men didn't try it at least once, and he had concluded it was because they were afraid they might like it. Rhonda saying "first cock" instead of, "a cock" must mean that she was certain he'd try it, like it, and want more in the future. There was only one way to find out for sure, so he nodded his head to indicate, "Yes."
Rhonda then began to tell whoever she was talking to that they were in the La Quinta on West Broadway near the Outer Loop and anticipating her next question, John used the fingers of one hand to flash her, one, one, four. After Rhonda had told the person they were in room 114, and said, "Bring her too," she hung up and John asked, "Who was that?"
"Remember the two `girls' you were admiring when we met?"
He hadn't realized she'd been watching him that close. Nodding again, he told her, "Yeah, I think so." "One of them was Bobbi-Lynn, my ex. And the blonde coming with him is Ginger."
He was still in position, kneeling at her feet and it seemed like he could smell the heat of her pussy, only inches from his face. He was torn between burying his face in her crotch and being a good host. He decided to let her make the decision. She hadn't said how much time they had before they'd have company. "There's only a couple of beers left in the fridge. Should I go next door to the convenience store and get more?"
She hesitated, then told him, "Yeah, that's probably a good idea. I didn't think of it. You would pick a place that doesn't have a bar or room service." Then when he reached for his pants, she asked, "Sure you wouldn't like to borrow my skirt and blouse?"
He knew she was just teasing, so he told her, "Not this time."
"Pretty sure of yourself, huh?"
He didn't know what he'd said that might give her the impression he was sure of himself. At that moment he wasn't really sure of anything. "Why do you say that?"
"Because you're automatically assuming there'll be a next time."
"Oh. I didn't mean it that way. But . . ." By then he had his pants on and she was still standing a few feet away. So he closed the distance and kissed her again. When they separated, he finished his sentence. "I really hope there is a next time."
Rhonda again studied his face, looking at his eyes to see if they looked away and as best she could tell, he was completely sincere. She almost felt bad about misleading John. She hadn't lied, but she hadn't been totally honest either. When telling him about her past, she'd made it sound as if she'd started dating Bob in high school and they'd been together from then until they'd divorced. The truth was, they'd never gone steady in high school. Bob had been just one of many boys she'd dated - and slept with. Then they'd both gone to the same local community college and it had been the same there - and more. Bob spent more time as Bobbi, started using the name Bobbi-Lynn, and often came to school in male clothing and makeup.
She'd like Bob - loved him in fact - but her friends would get on her for dating a guy that in their opinion was a swishy fag. They'd continuously tell Rhonda she could do so much better until Rhonda would accept their opinion and start seeing other guys. Then she and Bob had both gone to work after two years of college, and soon after, without her friends influence, they'd gotten engaged and then married. So while Bob had been the mainstay of her love life, she'd heard lots of lines from other men, had learned to spot the ones that lacked sincerity, and was pleased that John wasn't one of them.
"Go get the beer and hurry back," she told him, gently pushing him away before their passion could build to the unstoppable stage. "And if they have any kind of white wine, Bobbi-Lynne and Ginger were drinking wine at the club and might want to stay with that." Then she giggled and added, "And don't worry. They're not used to drinking anything fancy. I like wine too, but that stuff at the club tastes almost like vinegar to me."
As John cut across the parking lot to the convenience store, he concluded that walking out of that motel room, with a woman like Rhonda, dressed in bra, panties, garter-belt and hose, standing next to his bed and oozing with sexual need, was definitely the most difficult thing he'd ever done in his life - and maybe the stupidest. Why, he wondered, as he made his purchases, was he even thinking about doing anything with a make-believe woman when he had the sexiest woman he'd ever known apparently willing to spend the rest of the weekend with him? He chuckled when he thought about Rhonda calling herself a dumb-ass. Maybe he was the real dumb-ass of the two of them. But he knew she was looking forward to watching him suck his first cock. She'd said she loved to watch her ex when he did that. And the thought that he was going to fulfill a fantasy which he was sure he'd enjoy, and at the same time bring pleasure to the person whose cock he'd sucked, AND give pleasure to Rhonda too . . . if there were such a thing as a win-win-win situation, maybe he'd found it.
"That didn't take long," she commented as he walked in the room with his packages.
"I was in a rush to get back to you."
There was a twinkle in his eye that told her that this time he was teasing her. "Uh-huh." She was capable of teasing too. "What you were really in a rush for was the two pantied pricklets that are on the way. You were afraid I might get to them first and there wouldn't be any big old gobs of dick cream for you to drink up. Well not to worry sweetie. Bobbi-Lynn called just after you left to see if I wanted him to stop for anything. They . . ." The knock on the door interrupted her. "That should be them now."
He was closer, but she moved past him to the door before he had time to think about it. John wondered briefly what would happen if it wasn't her ex and his friend and she opened the door dressed as she was, but by then she had the door open and was ushering the two `girls' inside.
"This is my friend John," she told them, and then speaking to John said, "And John, these are my favorite girlfriends in the whole world. The cute one here is Ginger. For a homo cum slut, she does a pretty good job of eating pussy. And the ugly one next to her is Bobbi-Lynn."
Everyone laughed, including Bobbi-Lynn, who commented, "Nice to see you again too."
Because Bobbi-Lynn and Rhonda continued to tease each other, Ginger moved to stand next to John. "I understand this is your first time with a man, or one of us girls. Are you excited?"
John wondered for a moment how Ginger could have learned all that. He didn't recall that Rhonda had said all that much to Bobbi-Lynn on the phone. Then he remembered that Rhonda had said she'd talked to them while he was gone. She would have had plenty of time to relate most of what he'd told her. And of course Bobbi-Lynn would have passed it on to Ginger. So blushing slightly, he told Ginger, "Yes, it is - I mean I am."
"Let's see." Even as she said it, Ginger was groping the front of John's pants. "Not too excited," she commented, as her fingers closed around her target. "But you're getting there."
"You two starting without us?" Bobbi-Lynn asked.
Continuing to fondle John through his slacks, Ginger replied over her shoulder, "You said we were coming over here to break in a newbie. Why take all night to get to it when we could be doing it all night."
John was a little embarrassed to be the center of attention and still nervous about his first experience, but told her, "I like your attitude."
That gave Ginger all the encouragement she needed, if she needed any, and she undid John's belt and slacks, letting them slide down his legs. "Oh my! Silkies!"
"They're not really silk," John explained.
"I know that silly," Ginger told him. "We all wear nylon and pretend they're silk. Daphne is the only rich-bitch that can afford real silk."
John was confused. "Who's Daphne?"
Rhonda thought she'd better get back into the conversation, since she'd been the one to put together this impromptu party. "One of their friends," she explained. "They have a whole group of . . ."
"A circle of refined and personable ladies," Bobbi-Lynn interjected.
Rhonda scoffed at that. "Y'all sound more like a gaggle of geese. You're about as refined as those golden showers you like."
"That's recycled, not refined," Ginger piped in. "And don't tell me you didn't like it."
John may have been inexperienced, but he'd done his homework; at least when it came to the more unusual aspects of sex. He knew they were talking about pee play and was amazed that they all seemed to be into it. He'd read some stories on the internet about people that did that and he'd thought it was probably all fiction or fantasy. But he wasn't so startled by this new information that he didn't notice that Ginger had his cock out of his panties and was stroking it as well as he'd ever done himself. Then Rhonda stopped her.
To Ginger, she said, "I had him like that a few minutes ago, so it wouldn't take much of that to set him off. Aren't you the one that says cum should never be wasted?" Then, with the two separated for the moment, she turned to John. "Why don't you help me undress our guests?" Not trusting Ginger, she pushed John in Bobbi-Lynn's direction as she began to unbutton Ginger's blouse.
John suddenly realized that he'd never undressed a woman. He'd helped his ex with unzipping or unhooking things behind her back, but she'd never let him do more. So helping Bobbi-Lynn undress was all the more exciting. Her blouse buttoned in back, so he had her turn around, undid the buttons, and helped her slip it off, leaving her scarf in place. He thought it looked sexy that way. He remembered his earlier thoughts, when he'd tried to help Rhonda and she'd stopped him. He reasoned that Bobbi-Lynn wouldn't want to remove her bra and left it for her to decide. The hook and zipper of Bobbi-Lynn's skirt was also in back, so he undid that next, knelt to help her step out of the skirt, and then felt a new flush of excitement when Bobbi-Lynn turned to face him and he saw Bobbi-Lynn's cock, fully swollen and pushed to one side, quite visible through the shear material of her panties.
John might have hesitated a moment, seeking a go-ahead from either Rhonda, who seemed to be in charge, or Bobbi-Lynn, since it was his cock. But he did neither. Fifteen years of fantasy became reality in less than a heartbeat. One moment John was staring at the panty-covered cock and the next it was in his mouth- or most of it anyway. Only then did he pause. He had about half of Bobbi-Lynn's pretty prick in his mouth, and let it rest on his tongue while he took a few deep breaths and thought about it. He'd done it at last. This thing in his mouth was a real, live, hard, cock. A man's cock - even if it was attached to a man in lingerie.
But then, he was wearing lingerie too, just as he'd often fantasized he would be when this momentous occasion happened. There was no turning back now. He was a cocksucker. The only thing left to do at this point was suck until he made Bobbi-Lynn cum. And he definitely wanted to experience a man's cock filling his mouth with cum. He thought about Crystal, and the great blow-jobs she'd given him back when he'd been in the Army. They'd been way better than any other's he'd had. John tried to remember all the things that Crystal had done that he'd enjoyed so much and did those things to Bobbi-Lynn. He was concentrating so hard on sucking her cock that it took a while for the comments of his audience to filter in.
He heard things like, "You go girl," and, "Suck that dick," and, "Oh yeah - She sucks like a pro," coming from behind him. He couldn't tell one voice from the other. Ginger, in her excitement was talking about half an octave higher, and Rhonda's voice had gotten huskier. The two almost blended together. He could tell Bobbi-Lynn was getting close and wasn't surprised when she told him, "Wait a second. You're damn good. I'd better sit down."
John paused long enough for Bobbi-Lynn to sit on the edge of the chair Rhonda had been sitting in earlier. For the first time he realized Bobbi-Lynn was wearing stockings and a garter belt almost identical to Rhonda's. "I've got to get me one of those," he thought as he walked on his knees to resume his quest for Bobbi-Lynn's cum. Then, just as he was about to engulf Bobbi-Lynn's dick again, he thought to look back at Rhonda.
She was still standing next to Ginger and had Ginger's prick out of her panties. Rhonda had it in her hand, slowly stroking it. "Finish up," Rhonda told him. "There's another one waiting for you right here."
Then, no sooner had he begun again, taking a long slow, lick up the length of the cock before him, when Rhonda and Ginger knelt on each side of him, "To see better," Rhonda explained.
As John's head bobbed on Bobbi-Lynn, John wondered if that was entirely true or merely, as it seemed, just an excuse. One of the two was rubbing the front of his panties and without a thought, John reached to put Ginger's cock in his free hand, caressing it the way he'd seen Rhonda doing. He had to knock away the hand on his panties to keep from cumming as Bobbi-Lynn exploded in his mouth, giving him the first taste of cum that wasn't his own - unless you counted the cum he'd eaten from Crystal's pussy. That gave him another inspiration.
As the two she-males swapped positions, John turned to Rhonda and kissed her passionately. No stranger to that sort of action, Rhonda returned the kiss with gusto. John had never let go and still had Ginger's dick in his hand so he knew she was seated and ready for her turn.
Reluctantly, he broke off the kiss with Rhonda, said softly, "Looks like it's time to get back to work," and gave the head of Ginger's cock a kiss too.
Like he'd done with Bobbi-Lynn, for the first few moments John got wrought up in the new cock in his mouth, oblivious to the world around him. Just as his senses had begun to register anything except the prick between his lips, he heard Rhonda ask her ex where he was going and when he replied that he needed to pee, John heard her tell him to save it, that she thought their new sissy might like to try that too. John bobbed and licked and sucked a moment longer, then pulled off to look at Rhonda, smile and nod.
Returning to Ginger's cock, he thought, "Yeah. If Rhonda likes to drink pee, than I want to try that too. And anything else she might think is a good idea. When I finish with Ginger, I'm going to fuck her and then eat out my cum. Maybe she'll pee for me when I do that. That would be awesome. And maybe tomorrow we can go shopping together."
Then he thought about her earlier remarks about how she and Bobbi-Lynn had shared at one time, but eventually Bobbi-Lynn had stopped doing that. So he put his arm around her shoulders to pull her closer, pulled off of Ginger's slick, wet, prick, and pointed it at her, the invitation obvious. He had a suspicion that she'd been intimate with Ginger in this manner and the way she showed no hesitation proved it to him. Then he turned to Bobbi-Lynn and told him he was ready to try drinking pee, if Bobbi-Lynn would allow him.
Rhonda watched from the corner of her eye, never taking Ginger's cock from her mouth. She thought John seemed a bit surprised by how quickly his mouth had filled with pee, but was happy to see that he'd gulped it down and never hesitated to keep the flow coming. In fact it looked to her like John had done a much better job of it than she had the first time she'd tried that. She waited until she was sure he was finished with Bobbi-Lynn before turning Ginger's cock back to him, then watched as he eagerly sought Ginger's load, with Bobbi-Lynn's pee still dripping from his chin. "If that guy gives me at least one good fuck this weekend, without me having to ask for it," she thought to herself, "I might have to think about keeping him. And if he goes down on me after we've fucked, I just might marry him."
Little did she know, if that was the sum of her criteria, she should be planning the wedding . . .
Comments appreciated: amber_fountaine@hotmail.com