tagTransgender & CrossdressersWhy, She's A "He"!

Why, She's A "He"!


Tina had mentioned to Dave a bar she’d heard about that catered to certain sorts of sexual adventurers and suggested she and Dave visit one night to check out the scene. A friend had described it to her and said she occasionally liked to go there with her husband. These two were old fashioned ‘swingers’ and Jane had told Tina that this bar catered to those looking for sexual escapades a little out of the ordinary, as well as being a well-known pick-up venue. She and her husband, she said, had picked up more than one partner there. And those pick-ups were the start of some memorable evenings.

Now Tina and Dave were not what you’d call ‘swingers,’ and certainly not a ‘swinging’ couple. But they did enjoy sharing unusually frank disclosures about their sex lives and sexual interests. Apart from his very evident lust for women, Dave had confessed he’d had sex with men a few times, usually in the presence of a woman. And one time she and he had picked up a guy at a club and brought him back to Tina’s place where she persuaded Dave to let her watch the guy suck Dave’s cock and then have Dave fuck him. Tina knew men well enough to have sensed immediately that the guy they picked up was a ‘bottom’ and was apt to be compliant. He was. Dave’s was a basically dominant temperament, that was clear as day. And so was her own. But it was that very dominance Dave displayed, that sometimes cocky self-assurance, which led Tina to wickedly fantasize how he might react if the tables were somehow turned on him someday. Such musings, of course, revealed the dominant, the ‘top’ in her, conceiving how she would shape such a scenario, wanting to cajole and convince, maybe even to coerce Dave into adopting a rather different role. One he’d normally never imagine would fit his own sexual style and proclivities.

Such were the thoughts stirring in her mind as they entered the bar. Her friend obviously had told the truth. The bar, dark and moody, exuded sex. All the men, the women, the couples looked like they had one thing on their minds, and the duos and trios and foursomes she noticed gathered at the bar and sitting around tables seemed like they were here for the business of serious sexual seduction and negotiation, their overtures sometimes subtle, sometimes more obvious.

The two of them took a little table and ordered drinks.

“Check her out,” Dave said, pointing to a very sexy and sassy looking young thing. Though their one sexual adventure together had been with another man, Tina knew that it was women who generally rang Dave’s bell. Especially women such as this, sleek and sultry young wenches reeking of erotic allure. He had been frank enough with Tina for her to ascertain his preferred tastes in sexual partners.

“Yeah, Dave, a real piece of ass, just your type,” she said teasingly.

“That’s right. I wouldn’t mind getting under that cute little skirt of hers.”

“Don’t you think she’s just a tad slutty?”

“So? What’s wrong with sluts?” he said, her eyes fixed on her.

Now her ‘sluttiness,’ if that was what one were to call it, was of a special nature. It began with the skirt Dave spoke of lifting. It was a short, pleated plaid skirt, a sexy version of what you’d expect a Catholic school girl or prep school girl to wear. Along with the skirt she wore bobby sox and a pair of loafers. And on top, a white schoolgirl blouse. Other women in the bar were wearing slinky cocktail dresses, revealing halter tops, sexy little shorts and skintight jeans, but this woman’s seemingly demure Catholic schoolgirl outfit somehow made her seem sexier than all the others. Of course the skirt was very, very short, exposing much of her sleek, smooth thighs and that, as much as anything, made her outfit as provocative as it was. Also, rather different from what one would expect of a good Catholic school girl, her dark hair was fashioned in a ‘punk’ buzz cut and she had a tattoo on her neck, some Chinese ideograms signifying who knew what. On top all this, she had the prettiest of faces and a great, sexy smile.

Tina was amused watching Dave gaze at her, his eyes riveted like a set of lasers. But she did have to admit that this ‘schoolgirl’ was a pretty foxy package. And Dave wasn’t the only man in the bar ogling her.

She sat alone at the bar, nursing a drink, eyeing the scene, but looking rather standoffish. Her eyes did glance once in the direction of Dave and Tina’s table, and Tina gave her a little wave. She waved back with a cute, sexy little smile.

Later, after a few drinks, Tina needed to pee and headed to the ladies’ room, finding an empty stall. A moment later someone entered the adjacent stall. Tina could immediately see from the loafers that it was little miss sexy Catholic schoolgirl. But what happened next amazed her. For she didn’t sit down on the toilet, but instead lifted the toilet seat and pissed standing up, pissed like a man. Immediately it all made sense. Tina had thought that she was just a bit too sexy out in the bar, a bit overly provocative with her aloof ‘I’m such a hot piece of ass’ guise. So this was not a girl, it was a boy! Tina was delighted. She had a penchant for TVs, for trannies who paraded around done up as women. Most were painfully obvious. But this was one fooled even Tina, and certainly fooled Dave. She had noticed that slight protrusion in her neck, that Adam’s apple, but thought nothing of it at the time. Now she understood exactly what it signaled.

Tina left the stall and washed her hands, waiting for the ‘girl’ to finish up. A minute later she came out of her stall and joined Tina at the wash basins.

“Hi,” she said, brightly, remembering the wave back in the bar.

“Hello there,” Tina said, giving her a long look. “Can I tell you something? My friend back in the bar with me thinks you’re the sexiest thing he’s ever laid his eyes on. You should’ve heard the things he said he’d love to do to you.”

“Well, thank you,” she said and Tina now noticed she had a Latin accent. “Your boyfriend, he have very good taste.”

“He’s not my boyfriend, just a friend. But sometimes we like to pal around together and see what comes up.”

“You like go to bars and pick up chicks?”

“Sort of, except in your case we wouldn’t be picking up a chick, would we?” Tina said, giving her a meaningful look.

She said nothing, gazing silently at Tina. Then she smiled coyly.

“You were there, next to me?” she said, pointing to the stalls, “and you see that I stand up, right, honey?

“That’s right,” Tina said, now boldly sliding a hand under her skirt and giving a little squeeze to the obviously male bundle of goodies she had packed between her legs.

“I’m Tina, by the way,” she said, “and my friend out there who lusts for you, who you’ve given such a hardon, is Dave.”

“I am Claudia,” she said, sensing from Tina that she accepted her – or ‘him’ – for whom she or he was.

“Listen? Does Dave turn you on?” Tina asked.

“Yeah, he really cute guy, I could go for a guy like that. Que papi chulo.

“Well how about this?” Tina said, her wicked mind quickly improvising the ruse, “How about when we’re back in the bar you come join us at our table? You know, turn him on. Really turn him on. And then come back with us to my place. We won’t tell him a thing. Later on, when the time is right, he’ll find out what he’ll find out.”

“Hey, I no want him to get pissed off and beat me up. You know a lot of guys when they find out a chick is–-“

”Don’t worry about that,” Tina said, interrupting her, “that won’t be a problem. I know him pretty well. Everything will go nice and smooth. I’ll make sure of that.”

“Shit, man!” Claudia said, her laugh excited and frankly sexual, “sound like a lot of fun.”

So now Tina returned to their table, and a minute later, when Claudia returned to the bar, she sauntered over with her drink and took a seat next to Dave.

“I talk to your friend in the bathroom,” she said, gazing right at Dave, “and she tell me I turn you on, baby? Yes, papi? I give you hardon?”

Dave was momentarily numbed into silence, even blushing a little as he looked at Claudia, then at Tina. And as he did, Claudia, licking her lips seductively, discreetly slid her hand under the table. From the way Dave’s eyes went wide, Tina guessed where that hand probably landed.

“Yeah, baby, I think, yes,” Claudia cackled lustily.

They talked. It seems Claudia had moved to the Bay Area from Venezuela a few years ago. She explained she liked wearing the Catholic school girl get-up because as a teenager she had been thrown out of a convent school in Caracas when she was caught going down on a young nun. The nun was protected and sent to teach at another school, but Claudia was expelled. The scandal could not quite be suppressed, she said, her family was in an uproar and a few years later, when she was nineteen, she decided to leave and go to the States. She’d been here for three years now.

“How about we split this joint and go back to my place?” Tina said.

“Nice, good idea,” Claudia said, giving Dave another of her seductive glances.

Dave, usually glib and talkative, even cocky, was acting all mesmerized and puppy dog-like. Tina smiled to herself. Men! So predictable!

Back at her place, Tina opened a bottle of wine and poured out three glasses as Claudia nuzzled up to Dave on the couch, Tina on the other side of Dave, but further back, just watching, knowing what she knew.

“Yeah, baby,” Claudia said, sliding even closer, boldly resting a hand on the crotch of Dave’s pants, the swelling there already apparent, “back in bar all I do was give it quick little feel under the table. Now I can look?”

She turned to Tina.

“Is okay, Tina?” she asked coyly, playing the part of the irresistibly slutty temptress to the hilt.

“Be my guest, Dave’s cock is his business.”

With Dave almost panting now in anticipation, Claudia unbuckled his belt and slowly unzipped the fly of his jeans, then reached in and pulled it out. It was no surprise to Tina to see Dave’s cock come out of his pants fully erect. He was a horny little bastard, she knew.

“Hey, big boy, you got yourself a nice one!” Claudia said with her cute accent, her voice a little gruff, the sort of voice that was on the cusp of being between masculine and feminine. Which, Tina guessed, worked to Claudia’s advantage.

Now looking straight up at Dave, licking her lips, Claudia wrapped her fingers around his rigid cock and began twisting it seductively with her hand, stroking the shaft expertly.

“Oooooh, hard and thick. Claudia, she like big cock!” she purred, “and tastes good too, no?”

Now she lowered her face to his cock and began to lick it, first with teasing flickers of her tongue, then more frankly dragging her tongue up and down the shaft, doing it with the ease and finesse that suggested she had savored a hundred cocks in just this way. And, then finally, a moment after winking discreetly at Tina, Claudia wrapped her lips around Dave’s cock and began to suck him in earnest. He closed his eyes and groaned, savoring the sensations, pressing down on Claudia’s head. Tina couldn’t help smiling to herself. The only other time she had seen Dave get his cock sucked it was by a man. Now, again, it was being sucked by a man. Except this time Dave didn’t know it!

She took her time giving him a leisurely blow job, he greedy for the pleasure offered by her oral skills.

Then, suddenly, she pulled away.

“I have something for you to taste, honey,” she purred in a kittenish voice, kneeling up on the couch and turning her back to him. Taking hold of the elastic waist of her skirt, she very slowly lowered that skirt, revealing her buttocks. Dave gazed at the now partially exposed bottom with the same mesmerized expression glazed on his face from the moment he had laid eyes on her.

Lowering her skirt and the panties well down her cheeks, she left the skirt in place, the elastic waistband clinging to her trim, but appealingly rounded buttocks. Now she reached back and spread those buttocks. Tina had to admit this could easily pass for a convincingly female bottom. Smooth and hairless, even into the crack, the pretty little rosette of her sphincter now took center stage. Claudia, if she had much hair down there to begin with, certainly was careful to fashion for herself a perfectly smooth bottom.

She looked over her shoulder at Dave with that kittenish gaze,

“Lick my little ass, baby, okay? I like a nice, hot tongue in there,” she said, sticking it out for him, pushing it up to his face.

Dave did not have to be convinced, eagerly pressing his face between the vividly exposed buttocks and greedily beginning to lick the hole.

“Yeah, baby, lick it up! Stick tongue inside and lick like you mean it, stud!”

And lick it he did, with relish. One fact Dave and Tina had shared is that both had a strong anilingual penchant, craving an eager tongue between their own cheeks, savoring the pleasures of others’ receptive bottoms.

Now Tina watched as Dave lapped away hungrily at what he thought was a female bottom. She was being wicked, she knew, allowing Dave to be so audaciously tricked. She expected some moments of shocked outrage when the revelation was finally disclosed, but she had a hunch, a strong hunch, that she’d be able to steer Dave’s arousal in entirely new directions.

“You love the taste of that ass, don’t you, Dave?” Tina said to him as he gazed back at her, lapping away at the tender morsel.

“Yeah, Dave, he some ass-licking freak,” Claudia hissed, reaching back with an arm to push Dave’s head firmly against her bottom, grinding that bottom against his probing tongue.

Finally, she pulled away.

“Want to see what else I got to taste, baby?” she said, wiggling that hot little bottom of hers in Dave’s face, the skirt still halfway down her butt.

Now she stood up and, with her back to Dave, reached under the skirt and pulled down her panties, tossing them back to Dave, who brought the panties up to his nose to savor.

“Maybe you like too, baby,” Claudia said, slowly lifting her skirt up her thighs, stopping provocatively, then lifting a fraction of an inch higher, teasing Dave as he stroked away feverishly at his achingly erect cock.

Finally, with a flourish, Claudia lifted that skirt to reveal something new and shocking as Dave’s eyes suddenly went wide with stunned surprised.

Holy shit!! What’s that!?”

“Looks like a pair of balls to me,” Tina said cooly, her smile knowing, wicked.

“Yeah, papi, and I got me something nice to go with them.”

Now Claudia turned around and even Tina, in on the secret, was shocked at what she now saw. That pleated schoolgirl skirt of Claudia’s was being lifted, lifted by her stiff cock, now forming a strikingly obscene bulge under the plaid fabric.

“Check it out, sugar,” Claudia purred huskily, staring at a stunned, an amazed Dave, lifting her skirt above her waist, revealing ‘himself’ in all ‘his’ glory. Tina herself was stunned at the apparition. Maybe it was because Claudia was so petite, so slight, no more than 5'4" at most and narrow-framed, that the cock seemed so strikingly large rising from her. Most TV’s, Tina had noticed, had rather small, sometimes shriveled cocks. That was party due to much used hormone therapy. But this Claudia, flat-chested and narrow-hipped as she was, gave no signs of having used such hormones. No, this was a man, a small man, but with a very large and very rigid cock. It’s just that Claudia had that perfect knack for playing the part of a hot girl, a hot girl in a skirt and bobby sox, a blouse, lipstick, make-up and earrings.

“Nice and big and hard for you, papi. You like?” Claudia purred, showing it off, twisting her shaft in her hand, eager to display the now shockingly revealed male apparatus.

Now the key thing that Tina noticed was that despite the initial shock, Dave was not protesting, he was not wailing and whining about being tricked, there was no anger, no outrage. And even more significantly, his cock continued to remain very rigid, his arousal obviously not diminished, perhaps, Tina hoped, even enhanced.

Claudia now knelt on the couch and pushed her cock up to Dave’s face.

“Hey baby? You want taste?”

“Yeah, Dave, I think you should, I definitely think you should have a taste,” Tina added with a conspiratorial smile at Claudia.

He hesitated a moment, but then suddenly took the shaft in his hand and wrapped his lips around it. Tina was impressed. He had it in him, she realized, and now there he was, taking another man’s cock in his mouth. That the man in question just happened to look like and, for Dave, up to this point, to ‘be’ the hottest young slut you could imagine, only helped.

“Uh huh, papi! You know to suck cock!” Claudia growled, running her fingers through Dave’s hair. Now Tina came closer, wanting to gaze right into Dave’s eyes as his mouth was stuffed with another man’s rigid penis. The look in his eyes was complex. She’d watched him while he stood smugly, hands and his hips, another man on his knees before sucking his cock. And he always presented himself as a cocksman, he did the ‘doing,’ others were ‘done’ to. Now here he was vividly exposed to her in an altogether different guise, his lips wrapped around another man’s erection. There was a trace of self-consciousness in that gaze of his, but no real hint of embarrassment or humiliation. If anything, she sensed he knew he was pleasing her by displaying himself in this guise, knowing she herself had a strong dominant streak and imagining that watching a normally dominant man like him eagerly sucking another man’s cock was probably a very alluring sight to her.

“Look at you, Dave,” she teased, “you’re a regular little cocksucker.”

“Shit man! He fuckin’ good too, he suck it good,” Claudia said, kneeling there in front of Dave’s face, lewdly feeding her cock to him. Except for the panties she had removed, she was still fully dressed. The bobby sox and loafers were still on. She had unbuttoned her chaste, collared white blouse and now it was plain that the chest was boyishly flat and smooth. Were she a real woman, she no doubt would’ve been teased for being dismally flat-chested. And the alluring pleated skirt was still being worn, now pulled above her waist, exposing that shockingly vivid erect cock of hers. Tina had to admit that, altogether, it was an intoxicating mix.

“Hey, papi? You suck my cock and lick my ass. Me? I just taste me some cock. Now I check out that hot little bottom of yours, okay?”

Tina smiled to herself; Claudia was quite the eager slut. She certainly needed no prodding.

So now Claudia pulled her cock away from Dave’s lips and pulled off his jeans, then his briefs.

“Turn around, baby, and stick out for me.”

She helped him onto elbows and knees and urged him to lift his ass, taking hold of his buttocks, massaging them.


Now she spread open those buttocks, exposing his asshole, somehow looking especially vulnerable now. Tina had watched a man rim him. But, again, that time the other man was ‘servicing’ Dave’s bottom, on his knees behind him or down below, Dave firmly pressing the man’s face against his bottom as the other stud rimmed him. Then, when he had enough of that, having him bring his mouth further up and suck his cock.

This rimming, Tina guessed, would proceed very differently.

Mmmmmmmh, parece sabroso! Tasty!” Claudia said as she now pressed her face between his cheeks and lapped away at Dave’s asshole, making a real show of it, wanting to be as vivid and lewd as possible, this being her own style and knowing that this was the style expected by others.

Tina watched closely as Claudia devoured Dave’s ass, Dave moaning and sighing, enjoying all the attention. Then Claudia moved her tongue away and pressed a finger against his anus, sliding that finger up his ass.

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