By Marcia St. Denis and Erica Wright Copyright 2001. All rights reserved.
We wrote this story with you, as a connoisseur of erotic transvestite fiction, and your insatiable desire for the bliss of release uppermost in our minds. We hope our tale will bring you much pleasure over many sessions. Write to us if we have been successful. We would love to know that you enjoyed our perverted little world of depraved people and sordid affairs.
Chapter One
At 16, little Markie Deniston was afraid and lonely. His mother had died in a car accident the previous year leaving him all alone with his 42 year old step-father. Tom Deniston, a corporate lawyer with an elite client base, was lost without his wife. He had come unglued when she died. He was overwhelmed at the sudden upheaval in his world and had no way to deal with it. His life until that point had followed a well-scripted if not pre-ordained path. Prep-school, pre-law at Princeton, Harvard Law, Corporate Law Partner, then his own successful practice. Everything had worked as planned, along the way he had picked up a beautiful and intelligent wife. That she had a son from a previous marriage had been the only wrinkle, and a minor one at that as he grew to like the boy. Now, figuring out how to be a good parent to Markie was perhaps the hardest task he faced. It seemed almost to paralyze him with indecision about what to do or how to do it. Even he had to admit that at the best of times he hadn't been much of a Dad. He had never needed to be, with Sarah there to do the parenting for both of them. His career came first. His wife Sarah came second and Markie a distant third.
It wasn't that he didn't love Mark, it was just that he didn't really know what to do with the boy now that Sarah had left them. Making the problem a bit more difficult was the boy himself, so unlike any boy he had ever known before. Always a sensitive child, he had become even more so with Sarah gone. He reacted in very emotional, almost feminine ways to the stresses of daily life bursting into tears at the slightest remark that triggered a memory and, as a result, he had become obsessed with the memory of his mother. In so doing, he also had developed his own coping mechanism by setting up a shrine to her that he could visit to "be" with her. What she used to call her "special retreat", her "sanctuary": her combined bath, dressing room and boudoir had become a museum. He wouldn't allow anyone other than his father to come near the three rooms. Over the course of the two years since her death, Mark had retreated further and further into her world to the point where he spent every waking hour there other than when he went to school or came down to dinner. He had moved all of his clothes into the closets and bureau of her dressing area, took all of his baths in her large sunken tub and had eventually begun sleeping in the giant lace-covered, four-post, canopied and veiled bed that dominated her boudoir.
Tom wasn't so sure this was a good idea but whenever he walked into the rooms to talk to Mark and felt her presence so alive and intense, he was immediately calmed and intuitively understood why his step-son needed to be there. It was Mark's way of dealing with the grief and sense of loss that her death brought, and Tom hoped that it was just a phase that would pass.
Tom marveled at how perfectly Mark had preserved Sarah's presence. Mark had collected every photograph he could find of his mother and he seemed to treat the ones Tom had taken of her in states of semi-dress or in the bath, or at her vanity while applying make-up in her lingerie with special care and attention. With his step-father's permission, Mark put them in the most exquisite and ornamentally feminine frames he could find. Actually, Tom thought his son's choices of frames were entirely fitting since Sarah had been perhaps the most incredibly feminine woman he'd ever known. Her extreme femininity had been one of the major reasons he had married her and had become so entirely devoted to her. Unlike any woman he had known before, Sarah had immediately caught his eye as a young lawyer because of her always exquisite makeup and perfectly colored and coiffed hair, her incredible sense of style (wearing clothes and shoes that were at once stylish and sexy). She favored the body hugging, blatantly sexual style of Ungarro, Escada, Mugler and Versace over the blandly comfortable designs of Armani, Lauren, St. John or Donna Karan. She also insisted on the laciest lingerie, the filmiest nightgowns and peignoirs, the most obviously sexual push-up bras and the skimpiest bits of satin and lace thongs. She wore stockings and never pantyhose, preferring to go bare-legged if stockings wouldn't work with an outfit. She wore only strappy sandals or open-toed pumps and mules with 4" heels from Charles Jourdan and Manolo Blatnick and wouldn't be caught dead in the elegant matronliness of Gucci. She wasn't very interested in looking "comfortable". She was interested in looking sexy and available. She truly loved men and loved being the object of their desires. She dressed to attract their attention and there was never any doubt among her girlfriends at all about whether she dressed for men or for other women. She adored men. She liked everything about them. From their strong hands and broad shoulders, to their piercing eyes that seemed always to be undressing her, to their rough beards, to their musky smell, to their tight little butts, to their masculine obsession with contact sports and coarse bathroom humor, to their cute insecurity about the size of their dicks. She played men for everything they were worth. Sarah was the master of flirting and used her sexuality shamelessly to get whatever she wanted, whenever she wanted it. Tom Deniston was her greatest conquest.
Tom was a man's man. Tall, handsome, dark and swarthy, he was intelligent and ruthless. Hugely successful, he got whatever he wanted and most of the time he wanted beautiful women. The other times he wanted power and wealth and prestige. When he had married Sarah, he had abdicated his independence and subordinated his needs to hers. In effect, she became his world. Outside of the courtroom nothing else mattered. When she died, a large part of him had died with her. When Markie had begun collecting her pictures and arranging them on the antique French provincial side table and on the makeup cluttered vanity in her "sanctuary", Tom thought it was wonderful and he encouraged the boy.
He was largely unconscious of the gradual withdrawal from reality Markie was going through because he too had begun to lose touch completely with reality. Her death had hit him hard. He started drinking more than was good for him. He knew it would lead to no good but he couldn't help it. He needed the foggy release that the alcohol gave him and the liquor helped dull his aching memory. He was so lost that he didn't even notice that his practice started to lose clients. When for the first time, he couldn't meet his firm's payroll, he was unconcerned. 'Hell, it's just a temporary slowdown' he yelled at his accountant. Business would pick up.
But it didn't pick up. Within a couple of months he had to let most of his staff go. Worse was that it didn't bother him very much. By then he was thinking of other things. He spent most afternoons at a strip joint called "X-Girl's". Entire weeks of afternoons passed as he watched hot young 'girls' take off most of their clothes. After the second straight week he began getting plastered with his new best friend, Tony Zarelli. Tony owned the place and was a shrewd operator. His capo told him to keep an eye on Tom and to befriend him.
"You don't never know when ya gonna need a good lawyer. Ya know? Be nice to him. Let him taste the wares. Hook him Tony. Hook him hard." The advice he got from his capo was solid.
Within a month Tom began leaving the office around 2 PM. He would walk to the west-side strip joint and slip into the bar that had the sexiest babes with the nicest tits and the slimmest, tightest butts in town. By the time he sat down to have his first drink of the day he'd be sweating and beginning to feel the shakes come on.
"Oh Yessss! God, I needed that." Tom would hiss after his first shot. After 3 or 4 he'd start to feel better and usually about then, Tony would show up and take him back to the "Play Room" where one of the girls would be waiting with the six lines of white powder. Tony would leave and they would share it together.
"Oh FUCK" Tom would shout after the first line went up his nose. While his girl was snorting her line, he'd reach for her huge silicone tits and begin twisting her nipples with one hand while he got down on his knees between her spread legs to pull the suddenly tight thong to the side. He always felt a twinge of embarrassment when Sami's engorged cock throbbed into view. None-the-less he always began kissing and licking her sweet smelling, completely smooth, sexually charged cock and balls. Until the first time he'd done coke, the thought of sucking a big prick was the farthest thing from his mind. That first time he'd been flying and had just wanted to give his Samantha back some of the intense pleasure she was giving him. He had licked the purple tip tentatively. When she cooed to him, "Open your mouth honey, it'll just feel like the biggest hottest clitty you ever sucked..." he had done as she encouraged, and in no-time he had sunken further from his planned life. Even if he never did it again, he had sucked a throbbing cock till it erupted all over his face. He had never, ever thought that "cock-sucker" could be applied to him without error. Yet there he was, day after day, doing his lines of white pleasure and sinking to his knees to suck his babydoll's big fat prick till it poured out its thick, sticky, velvet cream.
That first time, Sami had grabbed the back of his head and pulled his mouth on and off her prick for ten or twelve minutes. As he sucked her massive bone, the thought of what was going to happen if his first-ever blow-job was successful never crossed his mind. When he heard her groan out, and then felt her entire body stiffen he should've realized what was coming, but he was way too high. She shoved her throbbing cock-head deep into his mouth and then began cumming. The first three or four globs of sperm, combined with her cock so far back in his throat, choked Tom. Her cum gushed out of his mouth and across his face, down his neck, soaking his tie and dress shirt. She pulled back slightly and emptied the rest of her load. Initially surprised and simultaneously revolted, Tom still began gulping down her salty cum. Her stern words of encouragement only helped drive his excitement.
"Swallow my load, you're my BITCH now! You think you're such a big shot lawyer... who's sucking a hard prick now?... Not me, but you, fucker! Keep gobbling my hot sperm... my sweet little cum-boy..."
He hadn't realized where her foot was until he was groaning himself. He had been absentmindedly rubbing his crotch against her shapely leg like a horny dog and she had happily rubbed the shiny tip of her pump against his cock and balls. He was surprised and over-powered by the strength of his orgasm, and kept sucking her softening prick until she pushed his face away.
"What a good boy... that was your first blow-job wasn't it little sweetums?" Tom looked down and shook his head yes. He looked at the huge wet stain on the front of his pants.
"Tommy liked it... you liked it so much you came too..." She pointed to the mess in his crotch. "Come here baby. Lets do another line. I think Sami needs your hard prick someplace dark and warm... we'll keep this cock-sucking thing our little secret. Hmmmm? OK? There, there, Sami knows what her little boy needs, doesn't she?"
That afternoon Tom had been so drained he thought he'd never be unable to get it back up, and that night Tony had sure found the videotape exciting.
"See... you got 'im now..." His cappo said watching the tape with him. "Get a couple more tapes like this, you'll have him in your pocket forever... wait, I got a fuckin' brilliant idea...maybe you can dangle a juicy tip in front of that cunt Samantha. If she can get her dick up his ass...on tape, that'll be golden. If he got high enough to suck her fucking prong and slip it into her sweet ass... who knows... maybe he'll do that too..."
On the tape of the next session, Tony heard Sami coo, "Ooooo, honey... Mmmmmm... that feels so good sugar..." She giggled. "...Now baby, slow down and come back up here to Momma so I can give you more of your medicine. Oh... yes! That's a good little boy.... Take this little bit of heaven all the way in... Oh yeah! Snort it deep... Now more for me... Ohhhhh fuck, yes..... Doesn't that feel good baby? Hmm? Don't you feel great? You flyin' dollface? Don't you want to make me feel good other places, sugar?" Cooing in his ear while opening his fly she would snake her hand into his pants, stroking his rigid member before finally freeing it from the confines of his pants.
He was learning to love sucking his special girl's cock, but this was the part of his day that Tom loved most. Every day. He loved what the Colombian Powder did to his brain and to his cock. He loved watching Sami scooch forward on the couch and lift her legs up to her double D chest. He loved feeling her perfectly manicured hand reach down to his throbbing tool and slick it with lube.
"Right there baby, stuff it in right there... oo-hhhh your big dick feels soooo good, stretching me wide open, after all the dicks I've had, I can't believe how good you're makin' this girl feel..." He loved watching her guide his tip to her tight hole and then hear her beg him to fuck her. Flying high from the coke only intensified every movement. To feel his big fat cock slide into her ass, past her incredibly tight sphincter and hang in the void of her rectum, was something he could never get enough of. Sarah had been adventurous, but she had never let him fuck her up the ass. Now that he'd had this incredible form of sex, he didn't ever think he could ever go back.
As he fucked in and out, he would hesitate briefly, enjoying the tight heat surrounding his cock before beginning to fuck Sami harder. While fucking her up her ass she would curse and abuse him with obscenities. He secretly knew that he really was the "perverted, worthless, disgusting, strung out piece of man-scum" she said he was. The knowledge of the degradation he was taking part in only took him higher than he had ever known was possible. He had gotten to the point where he could fuck her for fifteen or twenty minutes before pumping her ass full of sperm. All the while she would be groaning out in her throaty purr. Encouraging him to "fuck her she-male twat" and to enjoy "Sami's tight ass". Finally, as the sweat made their bodies slippery from exertion, she would beg him to stroke her clit,
"Squeeze my big fat girlcock huney. Please? Just take it in your hand you piece of cum-sucking crap... stroke it while you fuck me!" As he neared climax he would reach down between them and grab her enormous rock-hard stiffie. He would jack it in perfect time to his long hard thrusts, it was almost as if he were stroking his own cock. At this point they were more like animals, both racing to cum first. He wanted her to cum first, because as she came, her ass would contract wildly around his cock, driving him over the edge too. When Samantha's cum shot out and splattered their stomachs and chests and cocks and balls, he would finally succumb to a mind-numbing, muscle-paralyzing orgasm, the likes of which he had never known or ever even thought was possible. Afterwards, as they lay there recovering, his softening cock still up her cum filled ass, he could feel her cum and their sweat cooling on the both of them.
This particular day, she whispered something strange, "Honey boy, you see how crazy Samantha gets when you do her. Do you ever wonder what a big hard cock would feel like up your tight little boy-ass? Think about that for a minute babydoll. You could squeeze and suck my big tits like a baby, while I fuck you, and I could stroke your hard cock just like you do for me..."
He was stunned. Recently he had wondered just that, but even though he had sunk so low, so fast, he knew he wasn't quite ready to have his ass fucked by some cheap she-male stripper.
"Uhhh no. I don't think it sounds like much fun to me!" He said a little too defensively. Samantha knew from his hesitation that he had indeed thought about her cock sliding into his virgin hole, but she also knew not to push. In the past, she had had any number of 'straight' customers who paid to have her stuff her prick up their tight asses. She often thought about them going home to their wives or girlfriends with a hot load of her sperm up their butts. Tom was incredibly intrigued, what would that feel like? He felt his cock twitch and pulled back from Sami.
"Gotta use the john, be right back..."
While he was in the bathroom he cleaned up and decided to cut the night short.
"I just remembered, I have to get home early tonight... Do I owe you anything...?" he said smiling at Samantha.
"Nah...its all on Toni, you know that... have a good night."
She waved to him as he closed the door to the private room. She had felt his cock throb. She knew what he wanted. She knew she'd get him in the end.
"I'm gonna fuck YOU up the ass HARD!" she said laughing while pointing to the closed door. She lazily stroked her cock, imagining how good Tom's virgin hole would feel wrapped around her prick!
As Tom rushed home that night, more confused than he'd been in months he had no idea there was a three-grand bounty from Tony on his virgin ass if it could get caught on tape. He also didn't know that it didn't really matter what he wanted. Samantha was a professional, and she would gently prod, guide and finally push him until he ended up on his back, legs spread, begging for her hard bone to split him open.