Hard Time Sex

Hard Time Sex By Jenn Stewart and Marcia St. Denis Chapter 1 - The Fall

At 16 years Mark Harris looked young for his age. His soft ivory complexion glowed with the bloom of childhood. While other boys his age were beginning to shave, the silky down on Mark's full, rounded cheeks required no such masculine treatment. His dark brown hair framed his face in a riot of seductive curls and waves, which his doting mother Sarah desperately wanted to tame with a colorful ribbon.

Although, she had wanted a daughter fate had given her three boys. The first two were tough and rambunctious but the third, Mark, was a beautiful and sensitive child who was pretty enough to be a girl. But Mark was a boy and, although it was extremely hard at times, she had always resisted the urge to put a dress on him. He would have been mortified while she would have been thrilled. The desire to raise him as a girl excited her in a troubling kind of way that was difficult to even think about let alone try to come to grips with. Accordingly, she tried to put them out of her mind.

Mark idolized his big brothers and tried to emulate their male swagger and success in sports. However, by his 16th birthday he had to admit to himself what everyone else already knew: that he would not grow much beyond his 5 feet 6 inches and 110lbs, and would never make the football team or attract the string of attractive girls that swarmed around his brothers. Mark's talents were cerebral and, ultimately, more useful. He was already displaying some of the qualities of an entrepreneur, and had a precocious sensibility and good taste. He dressed impeccably and elegantly and wore his clothes with flair. That is not to suggest that he was not athletic. But his athleticism was that of the individual, which suited his thin, lithe figure. An avid cyclist and a competent sailor he had recently taken up rock climbing. These accomplishments won him the respect of his peers so that this pretty, doe-eyed, slightly built boy with full, kissable lips and a soft honeyed voice was never bullied.... even after he started to shave his legs when he joined the local cycling team.

In all respects Mark was a perfect child and displayed none of the teenage rebelliousness that, in his brothers, had made life interesting (and challenging) for his parents. He worked hard at school and consistently produced excellent grades. He was polite and charming, and had a radiant smile and an infectious laugh. However, there lurked a small flaw in this otherwise faultless character. He had a fatal attraction for some of the hooligan fringe at school. Like a moth to a candle, Mark was fascinated by the raw power and energy and sexuality of this group. They were a group of boys and girls who had early in life marked themselves out as trouble. Mark had been drawn to this group initially through a friendship with Nicky, an attractive boy with a devilish sense of humour and a capacity for fun that Mark found irresistible.

Mark and Nicky had been friends since Nicky's parents had bought the house next door to Mark's when both were eight years old. They went to the same schools and when Nicky began to wear leather jackets with brass studs embedded on the back and Doc Martin boots, Mark's affection for Nicky did not waver. Nor did it when Nicky shaved all the hair off his head and had a red and black devil tattooed on his chest.

Mark's parents' affection for Nicky dimmed and they advised him against associating with Nicky. They were sure he was jailbait. These cautions merely made Nicky more attractive to Mark. Naturally, while Mark hung around with Nicky he made friends with the rest of the hooligan fringe.

This unfortunate friendship took a serious turn when he accompanied Nicky and his friends on a shoplifting expedition. They stole some CD's. Any one of them had enough money to buy them. It was the pure excitement of risk-taking that drove them. As they left the store with their loot, Mark's heart pounded with the tension and danger and when they were free and clear he felt the seductive thrill of having brilliantly outwitted the forces of authority. The die was cast. He could not resist going on other expeditions, each more hazardous than the last.

Mark was 18 when he was arrested. He still had a perfect 'peaches and cream' complexion without a pimple or even the beginning of a beard. In fact, he seemed a mere child when he, Nicky and two other boys stole three bottles of Maker's Mark and bottle of CrŠme de Menthe, and walked into the arms of an off duty police officer as they ran out of the store. It was not a serious offence and Mark would have got probation except that one of the boys confessed, on behalf of the group, to all their other escapades. The wretched boy spilled the whole story because he was found to be carrying a gun. Unfortunately, the whole group was charged with armed robbery. Poor Mark was looking at hard time and there was nothing his parents could do to help him. His father turned his back on the boy. Sarah wept bitterly as a somber Mark was led from the court to a holding cell and from there to the penitentiary.

As Mark entered the cell complex a cacophony of wolf whistles erupted together with cries and shouts of "Yoh, be mine, baby ... Yoh gonna love riding my bone, baby ... I gots me some cream that gonna do yoh skin dee world of good ..."

He blushed hotly and a knot of fear formed in his gut. Although, eighteen years old he was still a virgin. Certainly, he had kissed girls at parties in games like "Spin the Bottle" and, at the last school dance, he had held one of the sexiest girls in school, sweet Natasha Nicolayev, in his arms as they danced the last, slow dance. Afterwards, he had walked her home holding her hand and kissed her open mouthed outside her front door.

Despite those chaste experiences he was under no illusions what the noise meant for him. Nicky's friends used to talk about what prisoners would do to relieve their sexual tensions. He was painfully aware that he looked effeminate.

Mark had learned about sex through Nicky, whose mother was a porn star. Nicky had discovered this when he found a collection of XXX videos locked in safe, which he had fortuitously learned how to open. It was a profound shock to him when, after putting one into the video player, he saw his beautiful mother being fucked by a big Latino guy who looked nothing like his father. Nicky soon got over the shock. At 16 he had already developed a strong vein of cynicism and this discovery simply deepened it.

After watching all the videos and cumming several times to the sight of his mom fucking strange men like an animal in heat, it dawned on him that several of the scenes had actually been filmed in his own house. It did not take him long to understand why he was sent to visit his cousins on so many weekends. It appealed to his warped sense of humour that the next time it was arranged for him to go visit his cousins on a Friday, he stayed instead with Mark, explaining that he had a "treat" in store for him.

The film crew arrived on Saturday morning and Nicky and Mark found it easy to sneak back into Nicky's house to discover that the action would be in the master bedroom. They hid in one of the large closets while the film crew was downstairs having a pre-shoot meeting. Nicky was not surprised to see that his father was one of the organizers of the event.

Half an hour later, as they watched from the darkness of the closet through the slightly open door, Nicky and Mark saw Denise, Nicky's mother, come into the bedroom wearing a tight, silver taffeta dress. Her hair was done up with a full and flowing river of curls tumbling down onto her neck and her makeup was thick and shockingly done. She looked like an expensive and incredibly hot and horny whore. She was gorgeous and they sensed they were in for a special treat. Usually, Denise just wore skirts and blouses, and occasionally cocktail dresses but this was the first time Nicky had seen her in a long, off-the-shoulder gown, which was only held up by the tightness of the material against her very large round breasts. It was cut to the point of barely concealing her nipples, which were clearly aroused and were making sharp points in her bodice. The long, body-hugging skirt was slit up the front to a point just a few inches below her crotch. The boys could clearly see the lacy tops of her stockings and the frilly, ribbon covered tabs of her garters. Her legs descended to her heels, which were the highest, kinkiest silver speckled strappy platforms imaginable.

Nicky noticed that the bedding was changed. The sheets, pillowcases and quilt were all in ivory satin. He had never seen her use satin sheets before. This was even more intriguing.

The film crew and three big black dudes followed her into the room. Her dress rustled sexily as she joked with the three black hunks. Nicky's father was busy directing the cameramen where to set up their equipment. The conversation of his mother and the studs was lewd and filled with sexual innuendo. The three men closed around her, kissing her neck and shoulders and fondling her breasts.

"Is that your big, fat, black boy cock I can feel against my butt, Johnny?"

"Yes, ma'am, an it be right ready to git stuck into yoh purty li'l honky whore cunt."

"Down boy! Hey Dave, I want to see more cum than those few pathetic drops you gave Sandy last week. I'm hotter than that tight cunted bitch and I deserve it, don't I baby?"

"Sho' nuff dollface, I gots enough boilin' inside my nuts to cover yo' tits with a nice thick coating o' delicious man-jiz, honey."

This banter went on as Nicky watched his mother squirming with pleasure under the simultaneous stimulation of three pairs of black hands and lips. The two boys had their stiff cocks in their hands as they watched the scene breathlessly.

Meanwhile, the cameramen were finished setting up. Two video cameras were set on tripods, one at the foot of the bed and the other at the side. An assembly of halogen lights stood at the far end of the bedroom illuminating the bed and the large area rug between the lamps and the bed. Two reflectors were set up near the bed to diffuse the light. Nicky's mother stood in the center of the rug looking ravishing in her dress. Her long dark hair cascaded in luxuriant waves over her bare shoulders. Towering over her petite body were the three blacks. All were powerfully built and had shaved heads. One had a goatee beard. He held her in an embrace and was kissing her lips softly. Her mouth was open and Nicky and Mark caught glimpses of his tongue thrusting between her lips. The other two stood behind her kissing her neck and shoulders and fondling her firm breasts.

She was swaying under the caresses of the hands and lips that pressed against her body. Her left hand rested on the crotch of one of the men behind her while her other hand rested on the back of the head of the man kissing her lips. After a few minutes she turned and the men who had been behind her took turns kissing her mouth while the third man squeezed and fondled her buttocks.

"Whenever you're ready Denise," said Nicky's father, who sat in a chair with a pad of paper on his lap

"I'm hot and ready, Jess." she said breaking from the kiss.

"Okay, carry on as you are and we will get the entrance later."

His mother and her three partners now began kissing and fondling with passion. Her mouth moved between the three men in a series of torrid kisses while they pawed at her body lifting her dress and probing her sexual entrances with thick black fingers. Other black hands slipped into the bodice of her dress and popped out her breasts, putting their mouths to the large brown swollen nipples, stretching them and sucking them hard. His mother gasped then screamed as her partners threw every sexual switch in her body at once. She tensed when her nipples were bitten hard and pulled away from her body until they snapped back. The expression on her face registered total passion and suggested her senses were on overload. She wrestled with them as they held her and rubbed herself against their bodies seeking to satisfy an urgent need they had unleashed. Nicky had seen his mother's sexual arousal on the videos but for Mark it was a revelation and it frightened him. Sexual pleasure seemed not far removed from pain and Denise's cries and screams were only marginally different from those that would evidence physical hurt.

As they embraced her, the men quickly undressed revealing three magnificent black physiques dominated by their enormous cocks swaying heavily in front of equally huge testicles. They had to be a full 10 inches if they were anything. What was remarkable was the fact that they were totally devoid of any hair. Their entire bodies were smooth. Ebony skin stretched over taut, rippling muscles glistened with thin films of perspiration. Their genitals were long fat fudgecicles waiting to be licked.

As sexy as Denise was to Mark, he was aware that he kept staring at the enormous veined cocks swelling and stiffening off the front of the three glossy male torsos. He pumped his own small organ as he wondered about and fixated on those big, ebony dicks. He had to catch his breath as he watched the cocks jerk and bob and drip their pre-cum. He did not think much about it as he watched but he was aware that he was drawn to the men more than he liked watching Nicky's mom.

She grasped two of the penises in her hands as they bent her forward and the third was thrust into her mouth. Sucking it hungrily she cooed and slurped on the rapidly stiffening member. Once it was erect the black dick was thrust hard and deep into her rectum. She gasped and cried out at this rough penetration but another cock pushed into her mouth and cut off her cries. She found this hard to keep in because the enormous cock slamming into her rectum was shaking her whole body.

Mark was fascinated by the way her breasts bobbed and swayed inside the pink satin, strapless bra cups under the bodice of her dress. He could see the garters of her matching pink garter belt stretching around her hips to her stocking tops and he began to wish she was his mom so he could sneak into her room to look at this strange and sexually exciting clothing.

Both boys felt an orgasm coming and they quickly covered their cocks with some of Nicky's mom's soiled, satin panties, which they had found on the closet floor. As Mark reached over to get a pair he accidentally touched Nicky's cock. A jolt of electricity coursed through his body at the contact. He picked up the scent of Nicky's pre-cum. Their physical closeness in such a sexually charged atmosphere was very disturbing. As he looked at Nicky's fist frantically pumping his satin covered cock, his own little stiffie started spewing cum. He was shocked. He wasn't even jacking off at the time. They both caught their cum and felt it slowly slip down their cocks as it soaked into the panty material. In the heavy sexual atmosphere of the confined space of the closet and the hot action in the bedroom their orgasms brought no relief from their erotic feelings. They held onto their stiff cocks.

Denise was lowered onto the bed by the stud whose cock was embedded in her ass. She lay on her back on top of him presenting her wet gaping cunt to the stud whose cock she had been sucking. He now slid between her legs and ploughed his erection into her dripping, pink vagina. She shivered and groaned as the long thick phallus parted the tender flesh causing some of her accumulated juice to gush out of her cunt.

Sandwiched between the two black men, their cocks plunging in and out of her, the third cock slid between her lips and filled her mouth. Mark and Nicky could clearly see the thick shafts shoved deep into her mother's anus and cunt with two sets of testicles bobbing against her bottom. Mark wondered what she must have been feeling. From the sounds she was making the sensations were intense.

The men were now working together, fucking her hard and fast in unison. Her moans and cries were muffled by the thick cock in her mouth, which she was barely able to suck because of the way her body shook under the combined thrusts of the cocks in her anus and cunt. The man she was fellating held her head to prevent his penis slipping out of her mouth and made fucking motions, fucking her mouth hard and fast.

She had no control. Her three partners were using all her bodily openings and gripped her so that she was helpless. Every few minutes they changed positions and, before their orgasms erupted, they had each been in every orifice three times. She had two climaxes before the men came and screamed as her body contorted and shook and fluid gushed from her cunt lips.

When the men came they signaled to each other as they approached climax, pulled out of her and she lay on her back. The men knelt around her head and, masturbating, they directed their ejaculations into her open mouth as she fondled their dangling testicles. Her mouth overflowed with thick white cum and a white globule overflowed onto her chin.

When they had finished she got up and took off her dress. She went into the bathroom and after ten minutes came out, naked. The two boys watched in complete fascination as the blacks fucked Nicky's mother several more times. When it was all over and the film crew had packed away the equipment it dawned on them that they had been in the closet more than ten hours. The boys had masturbated six times until their cocks were sore. For the rest of the weekend Nicky and Mark watched all of his mother's videos. But while Nicky may have been watching his mom, Mark couldn't help but be increasingly fascinated with the cocks.

For months afterwards Mark had thoughts, which embarrassed him. He couldn't get the sexy image of Nicky's mom with those three black studs out of his mind. All he could think about was how she looked and what she wore and how she took care of those three studs. But what troubled him even more was his obsession with dark black cock and the creamy juice they shot all over her face. He started dreaming about it, at home, in school, in bed - especially in bed, when he would pull out his little cock and slowly rub and tease himself to orgasm using one of his mom's soiled panties wrapped around his hard little thing as he imagined what it must have felt like for Nicky's sexy mom to be fucked and sprayed with cum.

Now, as he was marched along the jail's gallery to the cacophony of wolf whistles and shouts Mark was fortunately unaware that his picture had been in the newspapers and there had been a lottery among the inmates to see who would have him first. The lottery was fixed, of course, and he was "won" by two thugs, a black gang member and a Mexican drug dealer, who had established themselves as the prison enforcer and the prison dealer, respectively. They had Mark's picture from the newspaper pinned to the wall and had spent several days jerking off as they fantasized what they would do to him.

Mark was pushed into a cell on the third floor, almost directly across from Vic and Bono the two inmates who were the lucky winners of this slender, young, effeminate boy with the soft, flawless skin, the big doe eyes and the plump rounded buttocks of a girl. He was prettier than the photograph, even in his prison overalls. They were pleased to see that he was put into Jenn's cell. Within months of his arrival several years ago, Jenn, whose real name was Jeremy, had become the jail trannie. He was called Jenn by the other inmates and was, after two years on the inside, the undisputed prison "madam" of the place.

Jenn had organized a small group of the most attractive young men and trained them to provide for the sexual needs of all of the inmates who had the money or the drugs to "buy" their services. The guards protected these girl-boys from the more violent cons and, in the interests of peace in the prison and some nooky on the side, they allowed them to ply their trade. With the active help of the guards, Jenn had built up a collection of women's clothing to make his sissies more seductive and desirable, thus commanding a higher price. Jenn, who had organized and rigged the lottery to ensure that Vic and Bono would get to pop Mark's "cherry", welcomed the pretty new member into his cell and the sisterhood.

Chapter 2 - Loss of Innocence

"Oh huney, c'mon..... give me what I need!!! Pleeeeeease baby?" Marcia whined. "I got all dressed up special for you, just the way you like me. Mmmmmm, feel my soft, silky nylon covered legs and thighs...... Yeah, that's it lover boy. Oooooooo, and my fat, soft, round ass ... Ooh yeah, baby ... feels nice in this satin skirt ... Oh baby ... don't forget mommy's big tits ... suck those juicy nipples ... Mmmnnn! ... pinch them, harder ... Uummmm! ... You know I'll be good to my baby, don't you? You know I'll take care of my huney ... Oooh ye ...ees ... mommy needs her juice, baby. She needs it real bad baby. Mommy'll fuck and suck for you and drink your cum, just... give me what I need."

Marcia reached down into Bono's groin and slowly and softly jacked his cock into a state of erection. Marcia always loved the feeling of total power he got when that happened and he knew he had Bono right where he wanted him. They needed each other. Marcia gave Bono the best fucks he had ever had and Marcia got his shot.

Bono pulled the plunger of the syringe back slowly and Marcia almost fainted as he watched the clear amber liquid get drawn up into the plastic chamber from the bowl of the spoon. He quickly bent over and pulled his skirt up and over his white bubble butt and waited for the bliss to hit. His huney took a pinch of his skin and jabbed the needle deep into his left ass cheek and slowly pushed the plunger all the way down.

[D1]The heat of Marcia's special blend of Mexican heroin, Columbian cocaine and female hormones entering his system hit him and took him over the edge. The bitterness hit the back of his throat and he smiled contentedly to himself. That was the taste of pure pleasure. Now he could take cock all night long starting with his sweetie's and love every inch and every thrust and every hump and every cum, right down to the last salty, sticky, gooey, sweetly delicious drop.

"That's what I needed." he thought. "Oh dear God, that's what I needed." Bono was his man. His babydoll. He let him sample all the new shipments before anyone else. He would do anything for him to get his fix. And he didn't think about the fact that he seemed to need them more and more often lately. Bono understood his need and liked the fact that this whore was his now. His dark golden latino cock slipped past Marcia's stretched and lubed sphincter and Marcia didn't know what felt better, Bono's cock and the fucking he was getting or the shit coursing through his lily-white veins.

As he sank into contented warm oblivion he reflected on how he had come to be the Sherwood Federal Prison's youngest and hottest trannie whore. So he had a tiny little habit. So what? He had Bono to give him what he needed and Vic to protect him and Jenn to schedule his working hours and teach him how to be the best lay in the prison. And he had never been happier or more satisfied in his short life. Too bad no one but his mother ever came to see his. But mom was there to bring him the things he asked for and he knew he was loved and desired and needed by a lot of people, not just by his mother but by all of his new friends too.

Marcia loved his new name and was thrilled when Sarah stopped calling him Mark and started calling his Marcia. Jenn, too, was so sweet and thoughtful to give his that name and Marcia was always happy to take care of Jenn's needs too. He felt loved when Jenn would turn to him in the middle of the night, lift up his baby doll nightie, push his legs apart and enter him from behind. And all the while he would be stroking Marcia's cock with the material of the nightie until they both came and all of their pent up urges would pour out of them. Their coupling was tender and loving. They would kiss and cuddle and pet each other enjoying the softness of their bodies, the gentle caresses, the silk of their nighties. It was a time to enjoy their femininity, a pleasant change from the aggressive, thrusting cocks of the sex starved men they serviced during the day.

Marcia's cum would soil his nightie and Jenn's would slowly trickle out of his ass and down across his ass-cheeks until it dried crusty and fragrant. It was a feeling and a smell that Marcia had grown to crave.

Jenn was gorgeous and hot. Marcia wasn't really sure why Jenn seemed to have fallen for him so hard. Often, after Marcia returned from his daily visits to his boyfriend Bono, he would find Jenn weeping softly. At first he thought it was because Jenn needed a fix too but then he realized that he and Jenn were the only trannies lucky enough to get free heroin. Bono and Victor and Jenn, who controlled everything that went on in the prison, didn't give anything away unless they got repaid the way they wanted and needed to be. Often, when Marcia was off servicing his baby Bono to get his morning fix, Jenn would start thinking about this beautiful, young cellmate of hers and how sweet he was no matter what was done to his. In those quiet times, Jenn would reflect on the course of his life and how much he had grown to love this sexy sweet creature and then he would start to feel overwhelmed by his desire to hold and keep Marcia all to herself. The reality of his situation would often overcome his and he found herself crying softly at the thought that one day Marcia would be gone and he would be alone again.

When Mark had entered Jenn's cell that first time he stood transfixed and terrified and also excited at what he saw. Mark had entered a private domain that looked more like a wealthy woman's opulent boudoir than a prison cell. The walls had fabric coverings and in the center of the room was a large king-sized canopied bed. A mirrored vanity stood against one wall with a soft, luxuriously padded, satin covered vanity bench in front of it. The canopy over the bed was of a light pink, sheer chiffon with ruffled edges. A pink satin comforter covered the bed.

Against the other wall was an enormous armoire crammed full of women's clothing. Satin, taffeta and latex dresses, skirts and outrageously sexy tops were crushed together suspended from satin padded hangers. More than 30 different pair of high heels in every style and color imaginable were neatly arranged at the base of the armoire. The floor of the cell was covered in 2" thick off-white carpeting.

Jenn herself could not have been more than twenty years old. He had striking strawberry colored hair cut to mid-neck length but stylish to the max. His complexion formed a flawless background for his meticulously applied make-up. Carefully plucked and shaped eyebrows arched above striking blue eyes accented by mascara applied with precision to his long lashes. Crimson lipstick highlighted his full, sensuous lips. His long, natural nails were perfectly manicured. He wore a long, floor length, pale pink peignoir with boa feathers trimming the openings at the cuffs and the front.

Even with his 3" bedroom slippers on, Jenn wasn't much taller than Mark. He looked him over quietly. Not saying a word. As he approached, Mark was overpowered by the exotic scent of the perfume that he wore but he could not help but feel completely overwhelmed as he noticed an enormous cock swaying behind the fabric of the peignoir. This gorgeous creature wearing these incredibly sexy clothes was a man. His heart stopped beating. He stood in front of him and spoke.

"Mmmmmm, oh my sweet little sugar cube. You are going to make the cutest girl boy I have seen in a long time. We are going to have SO much fun." He cooed.

Jenn stepped closer and put his arms around Mark's neck and slowly lowered his glistening lips and kissed him in a way Mark had only fantasized about. His dick started to get hard and he wondered where he was and what was happening. Wasn't he in Federal prison? Wasn't it for men only? What was this incredibly hot chic doing here and why was he kissing him? Not only that but the guard who escorted him to this place was still here and was smiling at Jenn.

Jenn pushed Mark over to his bed and told him to sit there and not say a word. He pulled the curtain across the cell door and slowly pushed the guard down onto his knees. He was whimpering as he stared, glassy eyed into the folds of his peignoir. He slowly spread it open for him and when he reached out to touch his with his hands he slapped him so hard that Mark flinched. He had never heard or seen anything so vicious. Yet, the guard didn't move. He merely said, "Yes mistress. I have been a bad boy. I need to be punished."

"Oh? In what way have you been a bad little boy?"

"I made Jim Thomas beg me to fuck him, which I then did, and had a really nice big cum all over his ass. I still didn't give him his cigarettes until he had licked my asshole till it was open and nicely lubed. I made him watch while I fucked myself with my nightstick. He was so desperate for a smoke and a fuck that he didn't know what he wanted more, to fuck my ass or to try to steal the cigarettes from me."

"What did he do?"

"He jacked off on my face and then reached around me to get his cigarettes and, as he did I made him kiss me and lick all of his cum off of me."

"So how should I punish you? The usual?"

"Oh yes, please Mistress."

With that Jenn lit a big fat reefer and, taking it all the way down into his lungs, he breathed it out into the guard's mouth as he kissed him. Mark watch quietly as they got higher and Jenn's cock get harden and pushed out the front of his peignoir. Jenn's cock was a magnificent eight inches long, a truly masculine appendage on this most feminine of bodies. The guard's pants bulged and he saw Jenn reach down to free his cock. Raising the skirt of his peignoir as the guard knelt lower, Jenn pushed his rigid cock into the guard's greedy mouth. Jenn came within 4 or 5 minutes without a single word being said by either of them. When his orgasm finished he pulled his flaccid cock out of the guard's mouth and peed all over his face and into his open mouth. Neither Jenn nor the guard touched his throbbing cock as it spontaneously jerked and spewed long strings of semen onto the floor. Some fell onto Jenn's satin mules so he slapped the guard hard across the face.

Jenn took another enormous hit of his joint and breathed the smoke into the guard's mouth again. He left him there in a state of bliss, higher than a kite, drained and wet and happy. He leaned over and whispered into Mark's ear, "Did you like that? Want mommy to make baby feel good too?"

Jenn lifted him over to the bed and started undressing him. Without really thinking about it, Mark felt something go over his head that was light and soft and silky and smelled like perfume. He got up to look down and saw that he had some kind of see through robe on. He stumbled over to the vanity again and looked at himself and it took his breath away. He was wearing a midnight blue, satin nightgown. It made him feel pretty and sexy. The lace bodice barely covered his nipples. His cock hardened immediately. He stroked himself lightly through the smooth satin material. His head spun and his body was sensitive to every feeling and touch. His tactile sense was on edge.

He was thrust back on the bed, his legs spread wide, and his nightie pulled up to his waist. His rock hard prick stood rigidly to attention. Jenn's head went down between his legs and his cock flexed as Jenn's warm breath flowed across the almost purple tip. Mark gasped Jenn's head and pulled it down onto his cock. He came immediately. A tremor spread from deep in his groin throughout his body, tensing and arching his delicate frame as the first spurt of semen shot from the tip of his penis.

After swallowing Mark's semen Jenn raised himself and said that it was time for Mark to earn his membership in Jenn's stable. The guard got up and left the cell.

"Now baby, there are a lot of horny guys in this place and only a few pretty young things like you and me. It's our job to help them through their time in here by standing in for their wives and girlfriends. That's our job. Others have to do hard labor but you're so pretty you get to have lots of nookie instead."

Mark felt a sickening feeling in his stomach and fear in his throat.

"No, I can't do that ..."

He curled up into a fetal position and started to cry.

Jenn had opened the curtain allowing the inmates to see into the cell. A chorus of yelling broke out. The men were looking forward to watching the new recruit broken in. Mark could hear the nearest inmates yelling out to him, "C'mon over here sweet-cheeks, daddy gonna show baby white boy how to be happy."

And, "Big John got's what yo' needs, you little, sissy whore, right here 'tween my legs. Cum and git it, doll-face."

Jenn had stood up, towering over Mark. He reached down and slowly raised his head.

"Do you want to feel good? Do you want mommy Jenn to make his little baby feel happy and dreamy and better than he's ever felt before?"

"Yes", Mark replied weakly.

"Come over here."

Mark went over to the vanity where Jenn had put down a tiny pile of white powder cradled in a spoon.

"What is that?" Mark cried out in alarm.

"It's a special sleeping compound that we get here at Sherwood. Try it sweet cakes. You'll like it. I promise."

Mark bent over it and took it onto his tongue and swallowed it. He felt strange but dreamy and as light as air.

"Well, honey, feels good, hmmm??" Jenn whispered in his ear while she snuggled close to him lightly rubbing his thigh through the gauzy film of his nightgown.

"Oh ye ... ees!"

"And you sure do look cute in that nightie. Do you like it?"

"Mmmm!"

"Well sweetie you can take it off and put your overalls back on."

"What for?" This was not good news after so soon discovering the delights of wearing soft, sexy, feminine lingerie.

"Because, honey, my girls have to earn the right to wear nice things. It time for you to go to work. If I think you have acted like a lady you can dress like one. Now quickly, put your overalls on."

Reluctantly, Mark took off the nightie and slipped into his orange prison garb. Chapter 3 - Loss of Virginity

Mark got up and stood in front of Jenn in his ugly prison uniform with his head bowed.

"That's better. Now listen doll-face, there are a couple of horny young hoods across the way who have been looking forward to meeting you. Steve, the nice guard will take you over to meet them. If you're very good to those boys Auntie Jenn will get you more of that nice sleeping powder and find you some clothes that will make you the prettiest of all my sissies."

A stab of fear went through Mark as he realized what was being suggested. It was one thing to have oral sex with this sexy she-male but to be put in a cell with two hardened cons whose only thought was to fuck the shit out of his pretty, little boy's bottom was too much.

"Please Jenn, don't send me over there! Please don't ... I'm too small. I've never done anything like that. I'm scared."

The guard pulled Mark out of the cell-come-boudoir. Hundreds of inmates cheered and whistled as Mark was dragged, weeping, across the bridge to the opposite gallery where Vic and Bono, sporting huge, throbbing erections, waited for their pretty prize. The two hardened cons were over 6'4" with frames like body builders. Vic wore a red bandana around his head while Bono was shaved bald. They drooled at the mouth with lust. Mark's virginity was gone within 30 minutes of entering the cell. It was a very public display because the front wall of the cell was floor-to-ceiling bars allowing the inmates across the other side of the block to see in. Several guards also came and watched.

Vic quickly took off Mark's prison overalls and underpants leaving the youth naked and shivering in the cool air. Bono stood in front of him stroking his smooth, hairless, ivory skin and squeezing his plump round buttocks. Mark let out a little gasp as he saw Bono's huge erect cock, swollen with blood pumping through the shaft. This heavy, ebony cock jutted out from his groin at 45 degrees, easily eight or nine inches long. Hanging from the thick shaft, which was corded in swollen, blue veins, were two testicles the size of golf balls inside a scrotum of dusky brown skin. A thick mat of black pubic hair surrounded the base of his weapon. Mark thought immediately of the big, black cocks that had fascinated him when he and Nicky watched Nicky's mom make the movie.

As Bono squeezed his bottom and kissed his neck Mark's own pink penis hung limply from the small brush of soft pubic hair. Simultaneously, he felt Vic's naked body press against him from behind. In particular, he felt the con's cock, hard and wet against his buttocks. Mark was breathing hard as he squirmed and wiggled between the two horny studs, the wet tips of their erections leaving trace lines of shiny pre-cum on Marks stomach. He was scared and tense. He had no control over what was happening and it was an uncomfortable and alien experience. He kept reminding himself of Nicky's mother and how she had enjoyed three such men.

Both men kissed him and stroked his body while other inmates whistled and called out advice: "C'mon let's see that baby ride! ...stick yo' meat to him! ... Hey man, let's see some goo ... ood fuckin'!"

Mark felt Bono's hands spread his buttocks and Vic's wet cock press against his anus. He knew this was the moment. He closed his eyes and braced himself as the head of Vic's cock pressed into his anal opening and stretched it wide. He tried to imagine he was a woman and that he was wearing the nightie he had recently removed. It helped a little but his anus was hurting as Vic's big cock stretched it much too wide. He moaned as the pain increased.

"Oh, this baby's tight!" grunted Vic, then he thrust hard, "...Uuugghh!"

Mark felt the penis enter him and he cried out as his anus tightly encircled the head of Vic's cock. Suddenly, Vic's organ punched into him as his anus gave way and slipped over the wide crown. He felt the penis fill him up. It was hard and unyielding and felt much bigger than it actually was. The pain subsided and was replaced by a feeling of fullness as his rectum was quickly penetrated by two thirds of Vic's thick hard cock. He felt tightness from his stretched anus but the scary pain had gone. With the pain his fear began to diminish. He focused his mind on the sensations he had felt when he had worn the nightie, the softness of the material against his skin. He tried to imagine himself as a woman, as Nicky's mother, but his embarrassment was too much. With dozens of eyes watching and calling out encouragement to Vic, Mark was utterly humiliated.

Vic held Mark's hips firmly in his big hands so he could not have pulled himself off the cock if he had tried. But he did not try. He sensed it would do no good and just make Vic angry. After a series of thrusts he could tell that Vic's cock was completely inside him and seemed to reach as far as his stomach. His humiliation was compounded by that fact that he now had an erection. It was not by design but an instinctive response to anal penetration. Now as Vic pumped, Mark's penis jerked up and down in time with Vic's thrusts and the audience cheered as they assumed Mark was enjoying it.

Vic was very hot and aroused and banged his cock into Mark hard and fast. As his pelvis thrust forward and smacked against Mark's plump round buttocks their bodies made a loud slap. The inmates started clapping their hands in time to the slapping of their bodies and, as Vic fucked Mark quicker, they clapped faster. And he was fucking him really fast. Mark felt like a doll in the big, black man's grip and he realized he was moaning and whimpering. Vic was grunting and yelling as the swollen black cock hammered into Mark's slim young body. Mark's long blonde hair swirled around his head as his body was shaken violently then, as Vic gave three huge thrusts and pulled Mark hard back against his pelvis, jamming his fat, stiff, monstrous organ into the youth's bottom, Mark felt the hard penis inside him jerk several times. A build up of pressure deep in his rectum told him that he was being impregnated.

Vic's cock pumped a thick, gooey mass of semen into Mark and he could not hold it all. Some sprayed from his anus and ran down his thigh. Vic held him in a tight embrace until his orgasm subsided and he stopped shaking. The jail erupted in applause and there were cries for more. Vic pulled out of Mark and Bono was ready to replace him. He had been stroking his cock as he watched Vic, bringing his own shorter but thicker phallus to erection. Now he was in a high state of excitement as he savored the prospect of ending his week-long sexual fast inside Mark's gorgeous ass.

Mark gasped as he felt Bono's thick member plunge into him but it was easier now that Vic's semen had lubricated his anus. As Bono began thrusting Mark saw the guard come into the cell and unzip his fly. He pulled out his erect cock and clasped Mark's head between his hands and pulled his face down onto his penis. Mark knew what he was supposed to do and sucked the swollen member into his mouth and proceeded to rub the tip with his tongue.

Mark's body shook as Bono's cock gored him and the guard's penis frequently slipped out of his mouth. Bono soon came. Mark felt the huge cock buck deep in his rectum as more semen flooded into him and oozed out of his bottom between the shaft of Bono's cock and the lip of his anus. As Bono pulled out of Mark a stream of milky semen poured out of his stretched anus and down his leg. The guard now made Mark give his full attention to his cock. He licked the man's testicles and carefully rubbed the head with his hand, oblivious to the howling coming from the other cells. When the guard came Mark tried to pull the cock out of his mouth but the much stronger man held his head and ejaculated onto Mark's tongue making him swallow the cum. The taste shocked him.

The guard left and Mark rushed to use the toilet, which was again in full view of the cells. As he emptied his bowel he cried. Bono and Vic lay on their bunks watching him and massaging their erections. Mark realized they were not finished with him yet.

"No use yo crying, baby. Jes git used to it." Said Vic, "It ain't so bad. Chicks love it."

He did not reply.

"If you put out for us we'll look after you and see you're treated well."

"Si, babe," said Bono, "we'll give you some good fucking and protect you from some of the bad guys around here." He laughed.

Just then the lights went out. He got off the toilet and cleaned himself. As he moved over to the lower bunk, which Vic occupied, Vic seized his arm and pulled Mark onto his bunk. He kissed Mark on his mouth and thrust his tongue between his lips. Mark was passive until he felt Vic's hand gently stroke his small penis and testicles. As Vic continued kissing and stroking Mark began to come around. The combination of Vic's unexpected gentleness, the images of Nicky's mother that he used to help adapt to his situation and his youth and powerful, but hitherto dormant sexual appetite, was melting his resistance. He was no longer afraid that he would suffer physical harm from the sex act and even though his erection had been an instinctive response to being penetrated it was erotic. Now his penis stiffened in response to Vic's kisses and fondling and he felt a wave of sexual desire breaking over him. He threw his arms around Vic and kissed him passionately. Vic responded to the change excitedly and they both engaged in a silent but intense sexual tussle.

Bono could hear them and knew that this time it was not rape but hot sex.

He whispered, "Hey man, the chick's mine too. Save some for me."

Vic kissed Mark's neck and shoulders making him whimper with wanton need and, when he transferred his lips to his stiff, little nipples, Mark gasped at the eruption of desire that it produced. Vic had never felt so horny as held Mark's slender, effeminate body and felt the youth's kisses on his neck and chest and the small hands gripping his bottom. It was years since he had fucked someone who seemed to enjoy it. His principle experience of sex had usually been rape.

He felt the sissy's soft and slender legs clasp his waist and Mark's arm's hook behind his knees spreading his thighs wide. Vic slammed his groin against Mark's soft, plump buttocks and thrust deep and hard into the tight but well lubed anus pulling out till his cock-head almost popped out of Mark then plunged back down into that soft, clinging passage. Mark became a sex addict that night and his stiff little member several times erupted spontaneously into an orgasm that convulsed his slender body.

"Hey hurry it up man. I gotta have me some of that ass!" Bono whispered anxiously.

Mark held Vic in a close embrace as the huge penis continued to gore his rectum. When Vic's cock finally jerked and Mark felt the sperm impregnate him he was no longer a victim. He drew strength from the flood of semen entering him and he knew this was his ticket to survival in prison. Those terrifying men needed his beautiful, effeminate body. It was a measure of power and from now on he intended to use it and enjoy it.

As Vic withdrew his organ he whispered, "That was real good, baby. Yes sir, that was ... goood!"

"Be nice to me and it will get better."

"Consider it done, babe."

Mark slid off the bunk and joined Bono. He was immediately locked in another frenzied sexual struggle as the big, horny man unleashed his frustration. Mark fought back as the two kissed and wrestled desperately. Mark squealed and cried out his desire and pleasure as his slender body was mauled and crushed against Bono's naked torso.

"Oh god! I want it ... Uggh! Put it in me! ... Oh please, I want to be fucked! ... Ooh, yee ... ees!"

The other inmates hearing these age-old cries of human coupling unleashed a cacophony of whistles and shouts.

The bunk squeaked and shook under the stress of Bono's heavy body slamming against Mark's ass. When he felt himself cumming he pulled out and put his cock in the sissy's mouth.

The thick, spongy cock-head filled Mark's mouth with the taste of Vic's semen which had lubricated his rectum. As he sucked and licked the cock, this big, violent, ox of a man was still and moaned helplessly. Again Mark felt his power over these brutish men. He was the sole source of Bono's pleasure. He could increase it or diminish it. But it was not just power, Mark enjoyed the cock too. He fondled Bono's large testicles and thought of the sperm that his sucking mouth and busy tongue was coaxing from them into Bono's shaft. When it spurted into his mouth was, he swallowed it hungrily.

Vic and Bono fucked him twice more, passing him between their bunks before they fell into an exhausted sleep. Mark snuggled with his back against Bono's powerful torso. Semen had dried on his anus and thighs. He dozed lightly dreaming of the beautiful dresses hanging in Jenn's cell. He knew he had earned the right to wear them. He particularly thought of a pink taffeta gown that he seen. He would love to wear that. He imagined a tight strapless bra hugging his chest under the bodice of the gown. How lovely and feminine it would feel.

His reverie was disturbed when he felt the sleeping Bono's cock, which rested on his inner thigh like a soft sausage, stiffen and grow. He reached between his legs and held the organ. A surge of desire swept through him. He recognized that the dark Mexican was having an erotic dream. Raising himself on one arm he pressed his lips against the Latino's mouth, waking him in a high state of arousal. Mark was roughly manhandled onto his stomach and screamed as Bono's rock hard cock plunged into his rectum. Their struggle woke Vic and as Bono's orgasm subsided Mark heard Vic.

"Okay baby. Git yo cute little ass over here."

Mark pulled himself off Bono's erection and slipped into Vic's waiting arms.

Chapter 4 - Apprenticeship

Mark was awakened in the morning by the sharp jab of a needle going into his ass.

"Ouch! That hurts. What are you doing?"

Bono looked at him and replied, "Baby, sweet cheeks, that there's the best shit in the State. You just wait and tell me all about it."

Within seconds, Mark felt delicious and warm and loose. It was daylight and when he was pushed down onto Bono's bunk and once more fucked deep and hard, the other inmates could again see him being fucked. He was stimulated by the yells as they egged Bono on and jacking themselves into a frenzy. He could not scream out his own pleasure loud enough. He didn't care who heard him beg for more cock and cum.

With the drug acting on his brain every part of his body seemed to come alive and feel erotic. Bono's hands grasping his hips felt wonderful. Bono's lips on his neck and shoulders burned with passion. The cock inside his rectum felt huge. He gripped Bono's body in a frantic embrace. He was almost delirious with desire and doubted that he could ever get enough. The thought of being locked up with hundreds of very horny guys seemed suddenly to be very good luck.

When the guard came to take him back to the cell he shared with Jenn, he had to be carried he was so 'loosey-goosey'. Altogether, since entering Vic and Bono's cell he had been fucked 14 times and he had been transformed from virgin and neophyte to a sexually voracious sissy ready for a new career as one of the best lays in the prison.

Jenn was very pleased with Mark. She had watched as Vic and Bono had repeatedly fucked him. Instead of whining and being passive as so many of the other boy-girls in his stable had done on their first time, Mark had thrived and enjoyed each fuck more than the last. Jenn was definitely going to like training him.

Mark lay on Jenn's bed in a post coital lethargy and asked how he had managed to get so many clothes and such a luxurious cell. Jenn contemplated him for a while with an amused look in his eye weighing what he would tell him.

"Well, baby doll, this is how the system works..." And he proceeded to explain that he had already been a confirmed cross-dresser when he was sent to prison. On arrival he had the routine interview with the Warden who had already made a special study of Jenn's file. He had been waiting for someone like Jenn to turn up. He looked at the slim effeminate young man. Even his rough, baggy overalls could not diminish his extra-ordinary sex appeal.

The Warden had explained that he was looking for someone special and Jeremy (Jenn's legal name) seemed to fit the criteria.

"Special in what way?"

"I need a cock-sucking pretty boy like you."

The Warden said it harshly and with contempt. Jeremy blushed furiously. Although, that described him, he had never been called that so directly by a stranger. Hitherto, his inclination to dress as a girl had been accepted by his family and friends. Until lately his boyfriends had also been very sensitive and loving. But along the road to prison he had met some tough characters and learned to be tough himself. He recovered from his temporary lapse into innocence and responded in kind giving the Warden his sexiest pout.

"What've ya got in mind, huney? And my name's Jenn."

"Well now Jeremy ... er Jenn, one of the problems we have in this institution is that the men need an outlet for their ... frustrations."

He explained his plan to set up Jenn as the prison whore. He could take his pick from the few fancy boys in the prison and organize them into a sort of escort service. With regular and available sex, the Warden figured that he could reduce the danger of rioting.

In return, Jenn got his own cell decorated the way he wanted it to be and ordered anything and everything his heart desired from any catalogue or mail order house. He was also allowed to go on hormones and get several rounds of state paid, plastic surgery from breast augmentation, to collagen implants in his lips, to having the bottom two ribs removed from his ribcage (for a more perfect female waist), to having his Adam's apple shaved, and permanent eyeliner tatooed onto his eyelid.

"Work is part of prison life. If you don't do this you will work on the rock pile. I guarantee that within a week your looks will be gone and you will have been raped by scores of the cons. How about it?"

Jenn was under no illusions about being raped. Pablo, the boyfriend who had landed him in this mess, had done jail time and told him what happened to pretty boys. Jenn had enjoyed an active and eclectic sex life before being convicted so the offer of being able to control the sex and wear feminine clothes also was irresistible. He agreed to do it.

The Warden sent Jenn away and told him that when he had settled in he should change into a dress. A guard would bring him back to the Warden and he could repay his kindness. The Warden had some perverted needs and Jenn expanded his sex education over the next few months in learning to satisfy them.

Mark had to admit that Jenn was the most stunningly perfect creature he had ever laid his eyes upon. The juxtaposition of his incredible femaleness with his enormous 8" circumcised cock was overwhelming in its raw sexuality. Jenn was dressed in a pair of skin tight, hot-pink, lycra peddle pushers with 5" black, patent heels and a cropped, black satin blouse that was tied in a knot just below his enormous tits. His toenails were painted crimson red to match his nail color and lipstick. His short, pageboy hair was teased into a little bouffant in back and descended downwards to a point just below the end of his jaw. His teeth were snow white and his complexion was smooth and flawless except for the sexy beauty mark below his lower lip. His tits were at least 36D's and looked almost too big for his 5'4" frame. His nipples pressed teasingly against the lustrous satin of his blouse. [D2]Mark couldn't resist the urge to reach out and touch them. When he did the inch long nipples hardened and it hit him that they were real.

As the guard opened the cell door and let Mark in, the drug in his system and the almost continuous fucking made him swoon and he crumpled into a heap at Jenn's feet.

"Here you go precious. Let me get you to our bed. Feeling better? Did Bono give you a little surprise? You like that don't you sweetie?"

Mark could not really focus. He was swimming in pleasure from the swirling sensation in his brain to the completely satiated feeling in his ass and his cock. He fell asleep.

Jenn gave Mark a new name, hairdo, manicure and wardrobe. He became Marcia. And he loved every minute of his transformation into a whore. He did not think of himself as being gay. Rather he saw himself as a T-girl. Putting on a bra and a sexy dress, doing his make-up, arranging his hair was as exciting as the sex. He liked making himself look pretty and attractive for his men.

In addition to learning how to please men he had to learn how to hand wash his delicate and expensive lingerie making sure to get all of the cum stains out of them. Jenn was a demonstrative teacher and did not expect any of her students to do what he would not do. Before he was given his own list of inmates Marcia had to spend several days standing by the side of Jenn's bed, watching him take inmate after inmate into his arms and fuck them and suck them and be fucked and sucked by them until he had gone through that day's list of appointments. After each guy had left, Marcia would wash Jenn and redo his makeup and critically discuss each fuck-session. It was very hard work because Marcia would become unbearably horny but Jenn would not permit him to have any release until his training was finished. For seven days poor Marcia, wearing the sexiest clothes, had to watch as Jenn was fucked by more than a hundred inmates. The memory of his night in Vic and Bono's cell tormented him. He was being "wound up" dangerously tight.

Jenn knew what was happening. He intended that after seven days Marcia would be so sexually strung out he would lose all his inhibitions. And so he did.

Jenn had 12 T-girls in his "stable". Whenever possible they were encouraged to watch each other perform as well as watch and listen as Jenn took each of them through their lessons in makeup, hair styling and the differences in dressing styles depending on the time of day and occasion and the peculiar needs and desires of each of their customers. [D3] By the end of the first week after Mark was allowed to service the inmates. He would approach all the partners allotted to him for the day as though they were his first and only lover. None of the T-girls gave head like Marcia. He had a stronger sucking action and he could use his tongue like a magic wand. Because he learned how to deep throat, he would often take two partners, lying on a bunk or table being fucked at both ends. He liked the idea of semen simultaneously spurting into his throat and anus. He would cry out and struggle passionately as he rode their cocks.

Most of the time the inmates he serviced just wanted a blow-job or to fuck Mark anally. However, there were some who wanted more perverted things and these really excited Mark.

Within two months, he could do every boy's makeup and hair as well as tie off their arms and cook their heroin and shoot them into oblivion. He had learned how to dye and streak their hair and cut and perm and style them. And he could repair clothes ripped and torn in some especially hot fucking. He also gave better manicures than Jenn had gotten on the outside.

Jenn marveled at how far this pretty boy had come. He had a delightful, innate sweetness and a voracious appetite for sex. The rougher and more perverted the sex the better. Humiliation, gang bangs and powerful drugs all added to the excitement. Jenn had treated him to a set of 36D silicone implants and he was feeling sexier and happier and more fulfilled and more loved than he had ever felt on the outside. He was especially proud of the fact that there wasn't an inmate or a prison guard who didn't rank him as their first choice for fucking. While he preferred big cocks and guys who produced lots of cum he never turned anyone away. He loved them all.

And what was most satisfying was that Jenn seemed to need him too. Marcia was overwhelmed that he was the only T-girl entrusted with giving Jenn his daily dose of cocaine. Jenn loved the feeling of hyper sensitivity it gave him. As soon as he had his morning hit he'd look up through his long eyelashes into Marcia's pure ivory skinned face and his soft doe eyes. His eyes would glaze over and a look of pure lust would overtake him. Within minutes, Marcia's peignoir would be open at the neck or his tight little dress would be hiked up past his hips, his breasts exposed and his cock slowly jacked to an erection as his long distended nipples were bitten and chewed. The connection between his tits and his cock made him electric with desire. Marcia would moan and whimper and within seconds Jenn would be on his stomach with a pillow beneath his tummy so his ass was held high and Marcia would be on his knees between Jenn's splayed legs and his tiny little cock would be pushing in past Jenn's lubed sphincter.

Jenn was the only person Marcia would fuck. He had no desire to fuck men. He was feminine and wanted only to be fucked. But he would eagerly hump and thrust into Jenn's warm rectum. He always felt that when he spurted his cum into Jenn's deep passage that it was received as a love shot and not just sex. Without a pause Jenn would roll over and stuff his cock into Marcia's soft, loving mouth or his tight, young asshole and after a nice long, leisurely fucking, he would cum all over the insides of his baby's mouth or ass or he would have pulled out and sprayed his juice all over Marcia's face and neck and chest or his thighs and cock and balls.

Then he would saunter over to his desk, unlock one of the drawers pull out his spoon and needle and slowly cook Marcia's morning hit of hormones laced with heroin. Marcia was his baby and mommy Jenn would take such good care of his little sweetie. When Marcia was flying high and feeling nothing but bliss, Jen would invite in the first of Marcia's list of men for the day.

Chapter 5 - Mothers and Sons

When Mark, her baby had been taken away from her, Sarah Harris was in shock. Her two older sons had left, distancing themselves from the disgrace of their younger brother's incarceration, fearful that it would harm their careers. They had ordered Sarah never to contact them.

Mark's father had returned from the courthouse blaming Sarah for everything. It was her fault that Mark had turned out the way he had. She had coddled him. He had been her little prince. She had given in to his slightest demands. When the brat had hung out with that rotten Nicky, she had indulged him instead of whipping his behind like any normal mother. Within three weeks, her husband had deserted leaving her penniless and with an insecure future.

As her life unraveled Sarah became desperate. One day, after a visit from the landlord, she had, unthinkingly, wandered on to the street, tears of despair running down her cheeks and a crumpled eviction order gripped in her hand. Her precarious course through two streams of traffic was halted by the warm embrace of her neighbor, Denise Hardon, Nicky's mother. With Denise's tender and compassionate words in her ear she let herself be guided into the Hardon kitchen. Soon she was unloading her woes onto Denise and her husband Jess. Sarah stayed the night, and for the next two days. Denise and Jess provided comfort and encouragement and made her welcome. Sarah had heard rumors about their "unconventional" lifestyle and occupation but she was not a prude and realized that even if there were any truth to the rumors that they made pornographic videos it did not alter the fact that they were amusing and kind.

At 38, Sarah still retained her slim, athletic figure and firm breasts. Her features displayed the best characteristics of her Spanish forebears. Full red lips, a straight perfectly sculpted nose, black pencil thin eyebrows arching over dark smoldering eyes, and thick black hair that cascaded over her shoulders in luxuriant waves. Denise and Jess saw her beauty and sex appeal through the careworn mask of years of motherhood and recent tragedy. On the third night of her stay Jess had gone out and Denise persuaded Sarah to let her do her hair and try some different makeovers. Sarah enjoyed herself. It was like the pajama parties she had loved as a girl. Denise made her laugh and break out of her conservative straitjacket.

Sarah was persuaded to put on a black satin, under-wired shelf bra, which pushed up her comfortable and safe breasts into two brazen, ivory globes separated by a deep, inviting cleavage. She gasped at the image of the sultry Spanish beauty looking back at her from the dresser mirror. She had never worn satin lingerie much less black. Her bras were all functional cotton and nylon. Her bosom, with her nipples enlarged from the suckling of three babies and a husband, stiffened in the cool air and protruded expectantly over the lace edging of her bra. They looked positively erotic. She glanced shyly at Denise who was behind her looking at Sarah's reflection.

"Sarah, you have the most divine bosom."

As she spoke she lightly cupped Sarah's breasts and squeezed her hard nipples gently between her fingers. Denise felt a tremor pass through Sarah as she performed this fleeting, intimate act while Sarah experienced a small surge of something nice as Denise's warm hands cupped her breasts. Denise knew she had planted a seed of desire into fertile soil. She took a satin G-string, garter belt and fishnet stockings out of the dresser drawer.

"Try these. They will show off your gorgeous legs.

Sarah giggled guiltily as she put the sexy garments on.

"Oh dear. I look like a whore!"

"No, you're beautiful. Look in the mirror I was right you're legs are ravishing. Put these pumps on."

Sarah had never walked on heels higher than two inches. Now she tottered happily on four-inch stilettos.

The next two hours were a re-discovery of her femininity as she tried on dreamy satin and taffeta gowns, sexy PVC dresses and skirts, and divine silk peignoirs and chemises. At some point Denise had slipped out of the room and quietly phoned Jess to let him know that she was "ready".

When Denise heard the car come up the driveway Sarah was wearing a sheer, pink baby doll accented with a large pink satin bow at the cleavage and edged with soft marabou fur. On her feet she had pink satin mules. After some careful touching and kissing Denise had brought Sarah to a dangerous state of arousal. Her throat was dry and her vagina was wet. She desperately wanted to masturbate, something she had not done for years.

Denise had supplemented her subtle, physical stimulation with guileless chatter about her experiences in XXX movies. Shocked at first, Sarah became fascinated and, eventually, prepared to believe Denise that it was a life of high pay for lots of horny fun. So when Jess walked in with Peter, the star of several of his flicks Sarah was not quite frightened enough to try bolting. Nevertheless, she was embarrassed to be caught by two men in such a provocative garment.

Over the three days of her stay Denise had acquired a dominance over Sarah. Now she calmly slipped a flowered satin housecoat over her shy friend's shoulders and shooed the men into the living room. She, herself was wearing a yellow silk peignoir and her coolness and confidence encouraged Sarah to be brave, and a little reckless. Denise was pleased to see that Jess had brought Peter. She had partnered him in many films and knew that he had a knack for making a woman feel like a million dollars. They followed the men out of the bedroom.

The next hour followed a predictable pattern of drinks, soft music, talk and dancing and, eventually, kissing. Things then moved quickly and as Sarah's inhibitions collapsed a ravenous appetite for sex was unleashed.

All of her lovemaking with her husband was nothing like the sex she had that night. It was 7:00 AM when she finally fell asleep sore in both vagina and anus but serenely satisfied. She had been fucked multiple times by Peter and Jess, separately and together. Denise and she had made love languorously each time the men took breaks to recover. She had swallowed load after load of semen, finally acquiring a taste for it. She had also discovered a new and lucrative career. Within a week of that first orgy she was on a beach in Cancun sandwiched between two Mexican studs rehearsing the lead role in Jess's latest production. After the flick came out the reviewers raved about her innocence and naivet‚ which made her performance exceptionally erotic. Her sex scenes were very physical and vocal and she ate cum with all the discrimination of a connoisseur. Her career was assured.

One month after Mark went to prison she was also finally permitted her first visit with her baby. She had been shocked by her little boy's appearance. She had expected to find him sullen and frightened but he was, in fact, even more beautiful than she remembered. His skin glowed and his long hair had grown and appeared to have been lightened to a rich blond. His thick, silky tresses had been put up with soft tendrils of wispy locks wafting down the back of his neck. His fingers, always long and delicate, now appeared even thinner and more elegant and feminine than she had ever remembered. His nails were almost an inch long and perfectly shaped. They were also polished to a shimmering, soft pink and she was sure they were capped with white French tips. She had also been more than a little surprised at Mark's clothes. She couldn't really see him all that well through the glass partition of the visiting area but she was sure he was wearing a pair of extremely tight, black silk or satin jeans and she would bet her last dollar that on his feet were open toed 4" heel mules. But it was the bright, hot pink, chiffon blouse that had convinced her that her son was no longer the little innocent boy she remembered.

What had shocked her most was the way her body had reacted to what she saw. Within seconds, all of the long-past feelings of wanting to turn her feminine and delicate boy into a pretty and sweetly sexy, little girl had returned. She was taken back to the days when she wanted to put ribbons in his hair. What was upsetting her most, as she thought about all of this, was that her pussy had dilated and throbbed as it did when she prepared to do a scene with one of the studs on the movie set. As she strolled down the prison access road she could feel that her panties were quite wet. She couldn't shake the thought of taking her soft, sweet boy into her arms, kissing his lips, reaching down into his lycra pants and pulling out his perfectly shaped little cock. She guiltily imagined making him fuck her... hard and fast and hot.

She was sure that every man and woman who passed her could see, sense and smell the moisture that seeped into her crotch. She was positive that everyone could read her thoughts and that she would be thrown into jail for thinking the unthinkable: what her feminized son smelled like; how smooth his skin must be; how soft his ass and tits were; how stiff and erect his cock was; and how sweet his cum must taste. She was appalled at this guilty passion for her sensitive little boy.

When she had told him about the treatment she had received at the hands of his father and his brothers, Mark burst into tears and his mascara had run down his cheeks. She smiled and told him to wipe his tears and to make sure he fixed his makeup when he got back to his cell. Mark should have been ashamed or embarrassed at being found out but his morning shot was till working its magic in him and he could only start giggling.

When she asked him if there was anything she could get him, he said that he had everything he needed or wanted and that he felt like he had found a part of him that he had always known was there but that he had never really explored. She didn't say a word but she did reach into her purse and took out a beautiful diamond and sapphire ring. She passed it to him and when he put it on his finger she was rewarded with the most beautiful smile. She told him that it had been her mother's and that she had carried it with her ever since her mother's death. She also said that since she didn't have a daughter she could think of no one who would appreciate it more than he would.

It was then that Mark told her everything. He described how he had become Jenn's roommate and discovered the girl within him. He told her he been raped by Vic and Bono, how he had quickly learned to love their big cocks and the hard fucks they would give him. He explained that he was in demand and the other boys would fight over him. She listened with interest as he told her that Jenn was as close as a sister and had taught him everything he knew about being a sexy girl. Jenn had given him his new name and she was going to help him get a pair of real titties. She caught his sincerity when he told her how much he loved feeling this way.

He did not tell her about how much he had grown to need his little spoonful of junk and how good it made him feel but he asked her if she would still love him for the person inside even if he had turned into this gorgeously sexy girl. She had responded without hesitation.

"Of course, Marcia. You have become the pretty girl that I always wanted."

He glowed with pleasure when she called him Marcia. She kept her own secret from him, thinking only about his feminized body and hard girl-cock sticking stiffly out from between his legs. She tried in vain to drive the image away but her dripping cunt would not be denied the idea of being mounted by him. Visiting hours had ended before she could tell him everything that was in her heart. She knew he wouldn't understand. It would be better if she waited till he got out. She had a lot to think about.

Chapter 6 - A Mother's Love

When Marcia's two year sentence was over, he was released into the custody of his mother. Sarah came to greet him as he walked out of the gate. She kissed him and, taking his hand, she carried one of the two large suitcases that he had with him out to the car. Marcia stood in shock as he gazed at the cherry red Mercedes with white leather interior. Something was wrong. Not only was his mother driving an incredibly expensive car but it now dawned on him, after being lost in his own world these past two years, that she was a completely different woman from the shy mother he had left crying over him when he was taken away to jail. She was self-assured, beautiful and very sexy.

She opened the passenger door for her stunningly beautiful son and watched with an amused smirk as he carefully held the back of his skin tight mini skirt to his thighs as he minced his plump butt over to the seat and carefully sat down. He swung his slender legs, sheathed in taupe colored, hose with 4" high red heels into the car. Putting his matching red handbag on the floor next to his feet, he slid the seatbelt across his lap and nestled the shoulder strap between his enormous but gorgeously sexy tits before locking it in place. He was wearing a maroon chiffon see-through blouse with a lace appliqu‚d, pink, shelf bra clearly visible through it. His grape-sized nipples peeked over the top of the bra and poked against the gauzy material of the blouse. As Sarah got into the driver's seat beside him, she couldn't help but notice how he had already lowered the visor to check his crimson painted lips and fluff out his breast length, blonde hair cut in a Lana Turner style.

"My, my, what a vain little slut I have on my hands."

The drive home was silent. Marcia had a million questions to ask but was afraid of the answers while Sarah was wrestling with her own demons. Marcia was confused and upset because he didn't know what was the reason for the change in his mother or where all the money had come from. He would have been shocked and stunned if he knew what was running through his mother's mind.

They turned into a long tree-lined drive. At the house, a pretty, sexy girl came out to open his door before going round the car to open his mother's. She could not have been more than 16 but she was stunning. Perfectly coiffed and sumptuously dressed in a designer dress that looked like a $2000 Thierry Muggler with what had to be $300 Charles Jourdan, strappy sandals tied onto her dainty feet. Her face was impeccably made up and her hair had the sleek look of having just left a salon.

Sarah told the girl to put the car away and take her daughter's things up to her room. She then took Marcia by the hand and walked her into the house. Their heels click-clacked on the white marble floor of the entry. A door opened and Denise Hardon appeared. She was wearing a white, jacquard corset, the cups of which barely supported her splendid breasts. Her neatly trimmed pussy hair was visible beneath the lower edge of the garment. Ten frilly garters fastened to silky, white, seamed stockings stretched over her thighs. On her feet she wore 6" stiletto, white patent leather heels with ankle locks. She was carrying a whip.

Denise crossed the foyer, took Sarah in her arms and kissed her deeply on the lips. Marcia could see Denise's tongue snake between his mother's open lips. He watched with fascination as his mother lifted her hands up Denise's spread thighs and began to stroke her exposed pussy. Denise began whimpering and wrapped one leg around her mother's thigh, humping her cunt against his mother's trapped hand. As Denise kissed his mother his head filled with images of Denise being fucked by three horny studs. Her presence was as erotic now.

It took all Sarah's will power to extricate herself from Denise's passionate embrace. She turned to her daughter and said, "You remember Nicky's mom don't you dear?"

"Yes. Hello Mrs. Hardon."

"Call me Denise, darling."

Denise smiled and slowly slipped her hands around Marcia's neck. Without breaking her gaze or saying anything, Denise tantalizingly pushed her lips against Marcia's perfectly painted lips. Marcia closed his eyes and thought he would faint as Nicky's mother open her lips and pushed her wet, soft tongue into his open mouth and at the same time, felt Denise begin to rub her wet pussy against his thigh and her hand reached up Marcia's skirt to feel his penis held captive by his pink thong.

"MMmmmmm ... oooooh, Sarah dear, isn't he just the cutest thing! You were so right all this time when you told me what a hot little number Marcia had turned into. Aren't we going to have fun with him? I adore pretty young men in dresses. Oh! He's erect already and I just gave him a little kiss ... Mmmmm, it's quite wet too and really hard. Ungh! I can't wait to get at it."

Marcia shook with excitement as he was kissed and fondled by the woman who had given him six orgasms just watching her being fucked so many years ago. She was also the first 'real' woman who had held him so intimately.

Sarah reached over and laughing, slapped Denise's hand away from Marcia's skirt.

"Denise, mind your manners. I don't want to devour the poor little thing before he has a chance to unpack. I believe you have some guests to attend to?"

Marcia glanced into the room Denise had left to come out to greet them and caught sight of two upturned white asses with whip marks on them. Denise smiled up at Marcia, licked her lips and click-clacked her way back to the room she had left. She left the door wide open so that Marcia could hear the whistle of the whip as it came down with a crack on the bright red-welted ass of the person nearest the door and the sharp cry of deep pain and then the begging for more.

" Gillian, would you please show Marcia to her room?"

The same young girl curtsied in front of them and, taking Marcia by the hand, they went up to his room.

Marcia had been left alone. He drew a bath and luxuriated in the feel of the hot water as it soaked into his body. He was beginning to get the shakes and he knew he needed his medicine soon. He got out of his bath, dried off and put his see-through pink chiffon peignoir on and walked back to bed. He lay back on overstuffed pillows and let the white lace curtain of his framed bed close around him. He smiled in anticipation and his heart started to beat as he got out his kit and heated his hit in the blackened spoon.

He was just finishing tying off his thigh when he looked up to see his mother standing at his bedside. He started to cry out in shock and terror at being found out but his mother put her hand up to Marcia's mouth and stopped his cry. She leaned down so close to Marcia's face that Marcia could smell the perfume of his mother's hair and feel the warmth of her breath. They stayed like that for what seemed like minutes, staring into each other's eyes and then his mother bent down further and whispered into Marcia's ear, "Let mommy help you baby. You don't need to hide anything from mommy. I love you with all my heart and I have been dreaming of the day when I can have you all to myself. The Warden told me of your little habit and I think it's just fine, cuz now I have you where I want you... where you belong... giving your mommy all the pleasure she deserves while I give you what you need."

Slowly Marcia's mother removed her hand from over her son's mouth and replaced it with her soft wet, painted lips. Marcia was in shock, but not enough to deny the incredible eroticism of being caught shooting up and being kissed by his mother. His arms went up and around Sarah's neck and instinctively pulled Sarah down on top of him as he ground his lips against his mother's open mouth and drove his tongue deep into his mother's mouth.

Sarah pulled up and reached down to her daughter's thigh and delicately tightened the rubber strap that wound round it. She took Marcia's kit and slowly drew up the precious brown fluid from the spoon's bowl into the needle's chamber. Marcia had broken into a sweat as she watched, wondering where his mother had learned how to shoot heroin and hoping to God that she'd do it right and hit his vein and that he'd be floating in a cloud of bliss real soon.

Sarah lifted his thigh and slapped the vein that appeared behind his knee and as his mother slipped the needle into it and slowly pushed the plunger down Marcia felt the jolt of his medicine hit him. He gave a little soft laugh and floated back down against the frilly satin pillows of his bed. Lifting up his arms he embraced his mother and pulled her down onto him.

He reached down to the hem of his mother's dress and sliding it up and over her ass and hips he slipped his fingers down the front of Sarah's sexy La Perla panties. He was surprised but pleased to feel the copious amount of lubrication that was oiling her wonderful cunt. He rolled Sarah over onto her back and pulled her panties down her legs and off of her feet. He was on his knees between his mother's outspread stocking covered legs and looked into her glistening, heavily made up eyes as he lowered his head and softly licked his tongue up and into Sarah's fragrant gash.

Sarah cried out in ecstasy and held her son's mouth tight against her pussy as she ground it against that incredibly talented mouth and lips and tongue. She whimpered and screamed and begged for more and said she couldn't stand it and suddenly pulled him up on top of her and reached down to guide her baby-doll's hard girl-cock into her yawning cunt.

Marcia was in heaven. He had never fucked a woman before and it was a revelation. He had never felt how delicious a pussy could be. So different from fucking a boy's ass where just the sphincter was tight. Here, the whole length of his cock was being milked by an incredibly hot and wet and soft glove. He knew that he was good for only a few pumps before he would pour out his cream.

As he started to stiffen and his juice spewed out his cock, Marcia felt his mother go completely rigid and heard her scream out her orgasm. Just as his mother's orgasm was subsiding Marcia felt the second wave of H hit him and he slumped down into a drugged stupor of overwhelming sexual bliss. He was so lucky to be home and he couldn't help but wonder about what the next phase of his life would hold. He knew he would have to give up his beloved heroin and now that he was in the loving arms of his mother-lover he knew he would have the strength to do it. Could he give up men and cock and cum too? No way. Those were the only things a sexually loaded girl-boy like him lived for. Instinctively, he knew his mommy would help him get all of the cock he could handle and he drifted off to sleep.

Copyright - Jenn Stewart and Marcia St. Denis