tagTranssexuals & CrossdressersIntro to a Dream Made Real

Intro to a Dream Made Real


Jim had known growing up that he enjoyed bi-sexuality. But he had never found a man attractive the way women were to him. For example, he never found himself wanting to kiss a man, but he liked holding a hard cock as much as he enjoyed touching a wet pussy. He really enjoyed sucking a dick as much as he loved licking a hot hard clit.

After moving to a new city, lonely and horny became two conditions he would do almost anything to change. That's when he found himself perusing the "personal services" section of a local "semi-underground" newspaper, looking for a pro to help him out. Thing was, there were only a couple women who looked appealing, but they wanted more than he could go. Looking deeper into the paper he saw many listings for Transsexuals. He saw three that were so feminine, cute, and reasonable, that not only did he want to call them all; he immediately popped a huge woody.

Jasmine was a stunning redhead, with gorgeous long hair, big brown eyes, full red lips, and incredible curves. "Her" ad said she was available for sensuous massage! The second sexy tranny, Michele, was a blonde bombshell. Jim couldn't even believe she was a man underneath. Fist off, she was licking her lips in the picture, and looked like she was having an orgasm as her portrait was taken. Secondly, she was even better endowed than Jasmine appeared. He started rubbing his swollen cock through his jeans and hurried on to the last ad that had caught his eye.

Portia looked like the sexiest Latina babe he had ever seen. She didn't even mention massage in her ad. Portia was a Transsexual Dominatrix. OMG, thought Jim. Two of his biggest fantasies might be played out in real life if "she" was for real. He had been experimenting with bondage and discipline scenarios for a few years, often tying his cock and balls and feverishly fingering his own asshole as he talked to a phone-sex dom. But they had all been female, and none of them had been available in person. Just thinking about this had him on the verge of an orgasm, so he pulled off his jeans and shirt, and began stroking his rock-hard member in earnest, while alternately pinching his nipples and playing with his cherry asshole. He loved playing with his butt, feeling his muscles tighten down on his finger as he reached for his prostate. All this was too much for him and he came, hard, his juice covering his chest, and spilling onto the newspaper photo of Portia in front of him.

Jim's bi-sexual experience had been limited to mutual masturbation and some cock sucking with his friends. But what he really wanted was to feel a hard, hot, live cock deep inside, feel it filling him up, throbbing and banging against his prostate. And now it looked like he could have a dream come true. Without even cleaning himself off, he dialed Portia's number, and hoped her voice would match her feminine looks. It did!

Portia was available that very night. She made the arrangements for their appointment, and then became the powerful, stern domina Jim craved. She demanded that he clean himself properly, cleansing his colon, shaving his entire body below his neck, and that he show up naked underneath a pair of gym shorts and a t-shirt. Jim followed her directions perfectly, hoping to please Portia, and hoping she'd live up to his fantasies. He could barely keep from coming again as he shaved his cock and balls and ass. Showering, he dared not touch his penis, but he found his fingers playing with his ass again, this time two fingers went in as he massaged his sphincter muscle, and stretched himself as much as he dared, trying to reach his prostate just a little. But now it was time, so he dried and dressed as Portia had demanded. Shivering with excitement and a bit of fear, he grabbed his keys and jumped into his car for the lengthy drive, fearful that he'd disappoint his new Mistress if he were late.

He started getting afraid as he drove down the freeway. Portia's house was in the semi-notorious "gay" part of town, far away from his new apartment in the suburbs, so he had plenty of time to think. What if she had used somebody else's picture and really looked much more like the male she really was? What I if it was a scam, and he was going to be ripped off? No, he told himself. He had talked to her on the phone and nobody could have such a feminine, sexy voice unless she was truly into her transsexual lifestyle. But what if the domination and bondage were too much for him? How would he handle that?

As the miles swept by his thoughts mercifully shifted back to his fantasy. He couldn't believe this was really going to happen. His cock was semi-erect the last half of the 30 mile drive, as his mind drifted through vignettes of a hard-dick in his mouth as his ass was whipped by a cat-o-nine tails. Then he saw himself lying on his back with a gorgeous Latina babe, dressed in red PVC, looking down at him, his legs pinned back behind his head, fucking his ass like he was the girl, as if his ass was a pussy, pounding her throbbing 7 inch dick against his prostate as if it was a G-spot, grasping his erection, mercilessly jerking him towards a screaming orgasm. Then...he realized that he had missed his exit.

He sped up, and whipped a U--turn at the next exit, and made it back to the correct exit with minutes to spare. Driving like a crazed maniac, he pulled into Portia's driveway, with two minutes to spare. He'd made it. His heart was in his throat as he stepped out of his car and walked shakily to the stately portico. He thought he might pass out, his breath coming in short gasps, feeling his racing pulse as he reached for the knocker. Gingerly he touched the huge brass lion's-head knocker, lifted it, and down it came, "Crack...crack, crack, crack!" There was no turning back now.

He breathed as deeply as he could, trying to slow his pulse, and relax before the Dominatrix opened her door. And there she was—exactly like her picture, but no smile. In fact, she looked angry, and curtly said, "You're late!" He glanced at his watch, and Portia was right. He was 30 seconds late! His heart sank as his cock deflated. Oh no, he thought, what would his punishment be?

Before he could guess the answer to that question, Portia's deep, but feminine voice interrupted his reverie, "Get in here, and strip, boy." He stepped into what looked like an ordinary woman's living room, whipped off his shirt, stepped out of his sandals and dropped his shorts, exposing his hairless body, and immediately became completely erect, despite his fear, despite his racing heart, and shaking limbs.

Standing before him, Portia had transformed. Apparently, she had been in full Dominatrix costume beneath her robe, revealing her incredibly feminine beauty, and obvious physical prowess. Obediently averting his gaze, he looked down at the floor and directly at the sexiest pair of feet he'd ever seen. Her stilettos were miles high, with shiny black leather and diminutive brushed stainless buckles holding firm the intricate network of slender leather thong laces wrapping delicately, yet snugly around her ankles, calves, over her small knees, tight across her sculpted thighs to meld into her leather thong, amazingly continuing without break around her taut torso up under her pert breasts, exposing them enticingly and lifting them high, and up over her collarbones, and the strong curve of her shoulders to gracefully wrap at last three times round her fine neck.

No sign of a penis could be detected as Jim stared open-mouthed. His brazen impertinence was met with swift reprisal as Portia gave her new boy his well-deserved comeuppance. He heard rather than saw the whistle of the crop as Mistress delivered Jim's first lesson. The blow landed deftly bang-on the very tip of his swollen cock-head. Jim felt the breath leave his body as he involuntarily dropped to his knees in pain, tears dripping on his thighs. Seconds later he felt her lips on his neck, as she easily lifted him right to his feet, bent down at her knees, and sucked his pain into her warm, willing mouth.

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