His Wife Turns Him Into A Tranny Sissy:
He Takes His First Cock

J.S. Lee

This is a work of fiction. All characters are 18 or older.

He wasn't supposed to be here, well not like this anyway, completely hard and with a line of sweat that ran down his forehead, half nervous, half incredibly turned on. If Melanie ever caught him like this, there would be no lying about it. The lingerie store was far too great a temptation to walk away though.

In the back were the bins full of panties. Tiny lace g-strings, silky thongs and then his favorite, the full cut, satin ones, just feeling the material on his fingertips made him shiver and if he'd been alone here, he would let out the moan that he felt rising up in his chest. He was too far gone and grabbed half a dozen pairs of the underwear, in a variety of colors and forced himself to quickly walk to the cashier.

"Do you want a gift receipt?" the tall, thin blond at the register asked him.

"What?" he could hardly breathe, let alone speak. "No, that's fine," he was fumbling, his palms were damp and he couldn't pull the wallet out of his back pocket.

"What if your wife needs to return them?" she wouldn't leave him alone and he wanted to scream.

"It's fine, what's the total?" his pulse raced in his neck, the throbbing beat at his temple made everything else pale by comparison. He had to leave.

Finally, with his bag of forbidden treasures, he made it to the car. He was breathing so hard that he felt as if he'd run a mile, but it was like this every time. When he opened the bag and ran his hand through the pile of panties, he smiled and the wet spot in his underwear seeped through to the crotch of his pants.

The cell phone disrupted his slow, dirty daydream, it was his wife was calling to give him more directions. "Matt, when are you coming home?"

His voice was hoarse when he spoke, his hand still fingering the panties and his erection beyond his control, "Soon, honey. Do you need anything?" he went through the usual routine.

"No, I'll see you when you get here. Love you," when she would say that, especially at moments like this, the guilt would rush back and he imagined coming clean and telling her everything and the words would be right there, on the tip of his tongue, but instead he just said the usual good-byes and hung up quickly before he did anything stupid.

She would never understand.

That night, he held her until her gentle breathing had become rhythmic enough that he knew she'd never hear him leave. Matt eased his arm out from under her and stopped, watching her sleep. Melanie had gotten even more beautiful over the years, if that were possible. Her long, dark mane of curls spread out on the pillow beneath her, her full, pink lips that always looked as if she were ready to blow a kiss, her body may be softer now than it had been in college but her curves remained and it drove him crazy to watch her bottom bounce as she passed him.

If only that were enough. He shook his head to rid himself of the thought, he needed it and the need was powerful, palpable and after all, he'd been so good.

In the den, he found his hiding spot. In the corner, behind some shelves, where all the dirty, little secrets that he would come and visit lie in wait for his next slip, he retrieved the new bag of panties. His pajama pants came down quickly, he stood naked and his hard-on slapped against his pelvis as he pulled up the pink, silky panties that he had chosen for this evening. Matt knew which DVD he would watch and once he pressed play and sank back in the black, leather chair, he knew that it wouldn't be long.

The woman walked across the shabby motel room, she was dressed in a tight, black dress, the dark stockings ran up her slender legs and the high heels completed her outfit. Her ankles were unsteady in the shoes and you could see immediately that she was unaccustomed to stilettos. She sat down and her long, blond hair hung over one shoulder, she licked her red lips expectantly and a door that out of view opened.

The man stood at the foot of the bed and handed her the crumpled bills, her hand was trembling as she slid the money into the handbag that she had placed on the mattress. When he unzipped his pants and produced the enormous cock, Matt started rubbing his shaft back and forth through the satin panties. The man grabbed the blond roughly by the shoulder and pushed her down on her knees, with the other hand, he rubbed the wide, throbbing head of his dick on her lips. She looked up, hungry and eager for all of it, and opened her mouth wide to take the thick shaft in her mouth. Matt's panties were soaked now as he watched, shivering and biting his lip to keep the moan inside.

The camera zoomed in on the woman, bobbing her head up and down to take more and more of the monstrous penis that fucked her red mouth. A dribble of her saliva trickled down and hung from her bottom lip and Matt knew it would only be another minute or two before he exploded. The blond pulled up the bottom of the dress, drug it up over her hips and her small bulge in the red bikini panties she wore was exposed. She rubbed herself in her panties, the front of the material soaked with her sissy cream, she touched herself while servicing the man on her knees.

Matt felt his dick jolt and his orgasm shot out, coating the inside of his slick underwear, he gripped his shaft and felt wave after wave of his hot load cover him and the moan he'd been holding back for so long finally erupted from his throat.

"That's interesting, Matt," Melanie's voice, hard as glass, cut through the air and his hard-on withered as his heart sank. There was no where to go and no way he could hide it, he turned the chair around slowly and felt his cheeks burn and his stomach lurch. He couldn't meet her stone, cold gaze.

Melanie walked toward him, silent as she crossed the carpet, he should have known that she would catch him, she'd always been smarter than him. When she reached his desk, she looked at the movie on the screen, which had continued to play and she watched as the blond held her tongue out to catch the long spurts of the man's orgasm, her red lipstick smudged and her chin dripping with cum.

She looked down and saw his ruined panties, he realized that his hand was still on his tiny, soft penis and tore it away, hoping she hadn't noticed.

"So this is what you do in here, night after night, huh?" her lips pouted, her short tee-shirt barely covered her bottom and if he hadn't just came all over himself, he'd grab her right now and reach for her round cheeks. "Do you want to say anything to me?" and he swallowed hard, trying to form the words, even more nervous now that she was so close.

Matt could only mumble something unintelligible.

"I see," Melanie shot one eyebrow up and her round upper lip became a sneer, "Well, be careful what you wish for."

She left him to his imagination and he didn't dare return to their bed. After he had cleaned up and threw the shameful panties away, he tossed from one side to the other on the couch, picturing what she would do next. In the morning, his back hurt and his heart ached, he noticed the puffy, purple circles under his eyes and when he saw her in the kitchen with her coffee, he didn't understand how she could look so beautiful. Her long hair was up and two perfect ringlets caressed her neck, the fitted, dark blue dress hugged her curves and her face glowed.

She never smiled but before she left for the day she told him, "Be home at six o'clock tonight," and her shoes tapped to the door without another word.

Matt spent the day checking his phone for a sign of her, flashing back to the movie and the panties and nervously watched the time, which had never passed more slowly. When he arrived at the house, five minutes early, he called out to her, "Honey? Where are you?"

"Up here," she answered and he felt a glimmer of hope as he made his way up carefully, step by step. She didn't sound angry and he wondered if she weren't in the bedroom, wearing lingerie of her own, waiting to take him into her arms.

There was no sign of her on the bed, he walked through the closet and opened the bathroom door. Melanie sat on the edge of the large, sunken tub and waved to him, "Come here, Matt," and his heart hammered in his chest as he reached her, trying to press his lips to her but she evaded his grasp.

Melanie loosened his tie and unbuttoned his shirt, whisking the clothes off and when she grabbed his belt buckle to pull it loose, he murmured, "Oh baby, I want you so much," and the goosebumps that started at his neck ran down to the back of his thighs as he felt her fingers along his bare skin. He was standing at attention for her once he was naked, his dick waved to her and he longed for her touch.

"Get in the tub," she told him and he did as she directed, hoping that her blue dress would come off, over her head and he'd feel her legs open as she slid on top of him, he'd hold her bottom in his hands while she fucked him in the water.

She was silent and let him soak while she rummaged in the cabinets. Returning with a razor and shaving cream, she said, "sit up," and rubbed a dollop of the cream on his chest.

"Melanie, what are you doing?" he suddenly realized that she still hadn't smiled and the suspense was killing him.

"Shaving you," her voice was flat, she didn't care to elaborate.

"Wait," he tried to move, avoid the pink razor that was about to slide down the center of the white goo and remove his hair. "What's going on, honey?"

"Well, Matt, as I see it," and it was too late, she had already taken two long strokes across his chest, "you want to be a girl," and he forgot to try and stop her, his heart was in his throat again as her hands passed back and forth over his skin, "a girl in a dress, wearing panties and sucking cock, right?" Melanie moved her hand lower to the top of his belly and he felt the razor scrape across his skin there as well. "First thing a girl has to do is shave."

She was halfway done with his belly before he could find his voice. "Melanie, I don't want to be a girl, it's," his voice trembled but he pushed out the rest of it quickly, "it's just something I masturbate to sometimes."

"Bullshit, Matt," she was almost finished and he was hairless from neck to stomach. "Give me your arm," she sprayed more shaving cream and continued working the razor along every inch. "I've known for a long time what you really were, but I chose to go along with your little game."

Matt grabbed her forearm with one wet hand, "what am I?"

She finally looked him in the eye and a cold, wide smile spread across her face as she answered, "a little, sissy girl."

Melanie continued to shave and Matt trembled now under her touch, he was ashamed that his small dick bobbed up from under the water, as if it knew better than he the truth of what she said.

He complied when she told him to stand up and he looked down and watched her shave his legs. He couldn't help but let out a sigh when she reached his ball sack, a trickle of precum bubbled from his slit and slid down the length of him and puddled on her hand. "Don't you dare get your nasty sissy cream on me," her voice was as sharp as the razor. She raised her hand to his face and demanded, "clean that up."

Matt shook his head no and felt Melanie's sharp nails dig into his chin as she forced him down, "don't you ever tell me no, sissy."

He obeyed and tasted himself on her hand, the little salty droplets dissolved on his tongue and he couldn't deny that he felt more like the girl in the movie already. He closed his eyes and opened his mouth and in his mind's eye, the images of her sliding to her knees rolled by slowly, Melanie interrupted him with an audible click of her tongue.

"What did I tell you?" and she smirked and jerked his dick in this direction and that while she removed every last piece of hair. When she was finished, she told him to bend over and put his ass up in the air. Matt clenched and heard the groan that came from him as his beautiful wife ran her hands over his cheeks, then up to his crack, it was a dreadful combination of lust and fear when the razor blade moved along the tender, pink skin around his asshole.

"There you go, much better," she was finished and rinsing off the pink razor. "Rinse off," she told him and he sank back into the water, grateful that he could try to hide his erection again.

Melanie let the water out of the tub and handed him a towel to dry. "You'll need lotion, sissy, to keep your skin silky smooth," and she opened a tub with a pink lid, scooped up a hand of the perfumed cream and slowly slid her hands from his neck down his back. Matt melted under her touch and hoped that this was the last of it. After she rubbed his body, she'd take pity on him and take him by the hand and walk him to the bedroom where he could show her what a man he still was.

His hand trembled in hers as she led him out of the bathroom, through the closet once more and gently guided him to the bed. "Baby, I love you so much," he reached behind her to press his hands to the soft, sloping curve of her cheeks, if she would stay there, standing between his legs, he'd push the dress up and feel her bare bottom that bounced beneath the lace of her panties.

"You're not done yet, sissy," she dismissed him with a look and walked back to the closet. She approached him with a handful of lace and satin. "It's better to put the garter belt and stockings on first," Melanie pulled him up and before he understood what she was doing, she had hooked the back of the white, lace garter belt behind him. It was snug on his hips and when he looked down, he saw the white ribbons with the tiny, pink flower bows that dangled and brushed against his legs. At the sight of what he was wearing, a large drop of precum oozed down his thigh.

"Thought you'd like that, sissy," she looked up for a moment and rolled her eyes at him. The sheer, white stockings had seams up the back and she started pulling one up his leg. Michael could hardly breathe as he saw the silky material rise up on his thigh, the top edge of the lace was snug on his skin and when she fastened the stockings to the garter belt, he hadn't meant to say a word but he whispered, "oh God."

"Now for your favorite part," she stayed on the carpet and grabbed a pair of white, see-through panties, "put these on," she said as she helped guide them up his long legs. When he felt her tuck his dribbling penis into the front of the soft material, he grabbed her hand as if to keep her there.

"Please, Melanie," he didn't know what he was begging for, did he want her to stop or finish his transformation?

"Don't get grabby," she freed herself easily, his grasp was getting weaker the more feminine she made him. "Let me help you with the bra," she rose up and turned him around to place the matching sheer fabric over his hard nipples and hook him from behind. When she brought him back to face her, she couldn't help but giggle when she touched one of his pink, pointy buds, then jiggled his flesh, "you almost have little titties!" she exclaimed.

"Now sit down," she had walked back to the bathroom and spoke to him through the door, "you need help with your face."

It was no longer a turn-on and his pulse raced and his dick drooped instantly. "What do you mean?" his voice sounded higher as well.

She returned with a bag of brushes and containers, "Your make-up, what did you think?" she shrugged her shoulders as if this had happened a thousand times before.

"Wait," Matt put his hand up, seeing it tremble, he put it down quickly but continued his protest, "this has gone far enough. Come on, I know you're mad, but no make-up."

Melanie's hands were on her hips and she shook her head. "Don't you remember what I said, Matt?" the brush touched his cheeks and she swirled it around in a container of pink before she twirled it on his skin once more. "Be careful what you wish for."

He whined and hung his head, all of the fight had left him and he felt limp, she turned his face, touched him here, told him which way to look and to pucker his lips. She stood up, and with a look of satisfaction, rubbed her hands together. "Looking good," she said, more to herself than him and walked away once more, returning with a long, blond wig.

"This is going to be perfect on you," Melanie pulled the wig over his head and tucked his hair in underneath. "You're going to adorable for company."

Matt slipped back to the scene in the movie that he had jerked off to so many times before that he knew every second, every move, every sigh. He had pictured himself taking her place over and over while touching himself in the damp panties, but now, the image frightened him.

"Company?" it was the only word that came out and he didn't understand why he asked in a high, girlish pitch.

"Of course, Matt, we're having some guests over," she was walking back and forth from the closet to the bed. "I have to pull this dress on over your hips, don't want to mess up your hair, girl," and there was nothing to do but comply, giving her his feet, watching the pink material glide up over his stockings cover the panties, up to his bra and then she zipped him quickly inside.

"You're going to have to practice a little to walk in these," she warned Matt, holding the hot pink high heels in front of her, "and I want you to impress him." The word him sent a new wave of fear through his body, and he jammed his feet into the shoes.

"Who is "him"?" he meant to shout but it just came out in a pathetic whimper.

"Just look at yourself in the mirror," Melanie stood to the side, and gestured to the full-length mirror that hung on the back of the closet door. Matt walked with tiny steps, trying to keep his ankles straight, finally he arrived and he was mesmerized by the beautiful woman that stared back at him. The blond curls touched his shoulders and the dress pressed against his small breasts, the curve of his new hips enticed him and his legs shimmered in the white stockings. He puckered his pink, shiny lips and the girl blew him a kiss. She winked and twirled her hair like the coquette that she had always been. She shimmied when she walked and after a few minutes of practice, she could twirl, the hem of the pink dress fluttering around her thighs.

"I told you that you'd look beautiful, sissy," Melanie touched his shoulder and suddenly he was her husband again and puckered his lips in her direction, wanting nothing more than to feel her round mouth on him and melt in her arms.

"Yeah," she grimaced and pulled away, "save that for our guest." The doorbell rang at that moment and she called over her shoulder as she made her way out the door, "you wait there, sissy, the stairs are too much for you."

Matt sank to the bed, and strained to listen to the voices, Melanie laughed, a low voice chuckled, his heart beat so loud in his ears that he couldn't catch the words. Sweat snaked down the back of his neck and he felt it dribble on his long, blond hair and dripped down into his dress. Every footstep that he heard coming back up the stairs seemed to echo in his chest.

Melanie opened the bedroom door and peeked at him, "Richard, I'd like you to meet Maddie!" she made the introductions with a smile on her face. The man that walked in behind her was taller than Matt by at least six inches, even if Matt had stood in the heels, he would look down on his blond head. He strode briskly and reached the bed, Matt saw that his chest was far wider, his neck thicker, his hands looked as if they could break him in two easily if he but chose.

"Maddie," he nodded to the girl on the bed before sitting down, his massive thigh touching Matt's, sending fingers of sensation, something hot was running along his leg and up to the small, pink bit of flesh that simmered in the silky panties. "Melanie tells me that you have never sucked a dick before."

"But that she's always wanted to, isn't that right, sissy girl?" his wife stood in the corner and finished the sentence.

Matt could only shake his head yes.

"Well, Maddie, is that true?" Richard's large paw was on the girl's knee, and then slowly moved back and forth on the soft stockings, up a little higher, almost reaching under the hem of her dress. "Are you a virgin, little girl?"

Without thinking about it, Maddie spoke for him. "Yes," she cooed and batted her eyelashes at the handsome man who was touching her.

"That's so hot," he said as his wide palm reached up, over her little belly, to her right breast, skimming over the fabric of the dress and sending a long, hot ache down the entire length of her body. "Are you ready to show me how much you want to suck my cock, sissy girl?" he asked and his hand held her chin so that Maddie had no choice but to look her in the eye.

"Yes," she whispered and slowly, she moved off the bed and dropped to her knees, in a way that seemed strangely familiar and waited as the tall man unbuckled and unzipped, his pants made a jangle as they dropped to his ankles. Maddie could see the tip of his cock bulging above the waistband of his underwear and the clear outline of the solid, meaty shaft still hidden. She licked her lips and reached her hand up to touch him.

"Do you like touching that big, hard cock?" the man pressed her small hand to his erection and moved it up and down.

"Oh yes," she couldn't take her eyes off it and felt a throb in her own wet panties.

"Take it out for me then, sissy," he told her, his voice was low and authoritative and Maddie instinctively knew he must be obeyed.

She pulled down the underwear with both hands and gasped when she saw the long, pink dick, it was enormous and too wide for her to hold with one hand.

"What do you want to do with that cock, Maddie?" it was a rhetorical question, her mouth was wide open, she held it by the base with two hands and she felt the drool drop down her bottom lip and slide down her chin.

"Suck it," her whole body was shaking as she confessed.

"You know why you want to suck that cock, sissy?" he forced the girl to look up, his strong hand lifting her face once more, "Because that's all a sissy is good for. Now show me how you respect a real man," and he moved his hand off of her chin and reached around the back of her head to push her down to take the throbbing dick inside.

Maddie touched the tip of her tongue to lap the head of his cock, licking up his salty liquid that oozed there, then moved down to run her mouth around the ridge of his bulbous head. She felt him pulse in her two hands and with a whimper, closed her mouth around the head and swirled her tongue slowly, tasting him between her lips.

"That's it sissy, open your mouth and take it all," he commanded and she knew that the alpha male must be obeyed. She puffed her cheeks out and moved her head back and forth to take another inch and then another of the handsome man's solid erection. Soon she had half of the thick penis in her mouth and when she realized that she was only halfway there and the head of his cock touched the back of her mouth already, a splatter of her sissy cream soaked the front of her panties.

She was going to be absolutely stuffed with cock. Relaxing her mouth, she plunged ahead and took him inside deeper and deeper, until Maddie felt his slick head in her throat. She couldn't spread her lips any wider and she worked them up and down there, she was almost to the root and she gagged a little, a wet line of her spit wet her chin.

"Take your hands off now sissy, only use your mouth," he must be obeyed and she placed her small hands on his inner thighs now and the feel of his skin on her made the wet spot on her white panties even bigger. She started sucking him faster, her head bobbed as she had seen the woman on the movie do, the sound of her wet sissy hole being stuffed and released, just to be stuffed even wider with cock made her pick up the tempo.

"That's it, sissy, suck that cock like you were made to do," he man's hands on her head weren't even necessary, she wouldn't dream of stopping now until she swallowed his load. Her tongue lashed up and down and soaked him and teased him, she licked every ridge, the veiny line, she sucked him down to the tips of his bush of pubic hair and back up to his thick head.

The man started to pant and his hips thrust up, off the bed, driving into her mouth, he fucked her face, in deeper than before and back out until her greedy little mouth reached forward to take him back inside. Maddie could feel the tremor that ran down the length of him and she knew that in a moment, he would fill her to the brim with his buttery jizz.

She rammed her head down so that she would feel the first shot course down her throat. He howled as he spurt, shoving the salty mouthful deep inside. Maddie moved her head back to taste the next spasm on her tongue, feeling his sticky juices cover her there, she swallowed and when her lips were closed he coated her lipsticked mouth with another dollop of creamy semen. Maddie licked it up and kept her mouth open as the rest of waves left him and slapped her chin, her lips, her cheek and finally felt him weave his hand through her hair once more as he told her, "clean me up, sissy."

Maddie sucked up every last drop, lapping at his head again and tasting his slit, she licked around the head once more and then dropped her face in his lap, her breath coming fast and her entire body on fire with her girlish want. Melanie reappeared from the corner and now spoke to the man. "Did she do a good job, Richard?"

"Oh yes," he patted her head, the wig moved under his touch. "Maddie knows her place very well."

"Good sissy," Melanie touched her arm and when Maddie looked up and saw her pouty lips curl into a smile, Matt tried to speak.

"You wait there, Maddie, while I walk our guest out," she told him and once they were gone, Matt looked in the mirror and watched as he took off the wig and wiped his ruined lipstick off. He slid out of the heels and unzipped the dress with the damp place where his dick had leaked. He was attempting to remove the bra when Melanie returned.

"What are you doing?" she was shocked and rushed over to pick up the dress and shake it out. "You're not done, we've got to fix your hair," she leaned in to inspect his white encrusted lips, and wash the cum off your face.

"What's happening now?" all Matt wanted to do was take her in his arms and feel her chest to chest and feel her velvet lips on his neck, her soft kisses up to his ear and then feel her under him, wet and ready for him.

"We have several guests coming tonight, Matt," she had reverted back to his name and suddenly he could taste the load of sperm that rose up in his throat. "I hope you enjoy it," she licked her round, bottom lip once and then smiled, "I know I will."

His Wife Turns Him Into A Tranny Sissy: He Takes His First Cock

His Wife Turns Him Into A Tranny Sissy:
He Takes His First Cock