Sissy – body change – panties – satin – feminization – lingerie – cocksucking – gender swap
He swallowed hard, his body tense with anticipation and admittedly a small amount of fear. He didn’t _really_ know this woman and her beauty was no guarantee of her honesty. He was exposing himself as he had never done before, all in a desperate attempt to capture his dreams, to experience the most intense pleasures.
Looking around the bathroom he saw that it was finely appointed with grey and pink marble and fine Italian tile.
The towels were Egyptian and felt wonderful. The whole penthouse suite was luxury but for the money he was paying her, it felt appropriate.
The money had almost stopped him before jumping in but after twenty years of desperate fantasies and a collection of partial experiences, he couldn’t resist. She’d described things in such detail that he was completely convinced that she’d done this before. Some things had been left vague but tantalizing.
Maybe it was desperation that took out the five thousand dollars but he preferred to think of it as hope.
His skin was tingling as he dried off. Her instructions had been very detailed and had taken him awhile to comply with every item. He’d cleaned himself all over and then used a special depilatory cream from his toes to his hair line. With some embarrassment, he’d given himself an enema. He’d never felt so clean and his skin so smooth.
Leaning close to the ornate mirror, he took a good look at himself: fit, toned, a little on the lean side, a little shorter than average, longish black hair that he kept combed back loosely. He’d never been unhappy about his build. The fact that he could dress off the rack at women’s stores made his secret life ever that much richer. Most guys were too big, too tall, or just shaped too masculine.
Maybe the genes of his mother had given him a just little extra curve here and there. It had been embarrassing as a k** but when his secret fantasy life had blossomed he’d cherished any little thing that made him feel more feminine.
Once he was dry he stepped back. It took him a minute to recognize himself. Gone was the moustache he’d had for the last decade and there wasn’t even a hint of five o’clock shadow.
He definitely looked younger and, if he wasn’t just delusional, more… if not feminine, well, at least androgynous, less obviously masculine. He found himself daydreaming.
It had taken shockingly little time to set the whole thing up. He wasn’t deluded that his particular fantasies were “mainstream” so he was pleased that Coleen had understood his descriptions so quickly and well. She’d added suggestions that had given his hard-on an almost painful rigidity in excitement.
She’d spoken of applying her talents in very similar situations with other friends. She never spoke of clients or customers. Everyone was a friend which he felt was a nice touch.
He’d only discovered her after an awkward first visit to a swinger’s club where he’d been too scared to join in the fun. He just couldn’t get my courage up to strip down to his favorite lingerie in front of strangers though he had masturbated three times in the men’s room.
Maybe it was his reluctance that caught Coleen’s eye, but just before he was about to give up and head home, she asked to sit with him. She later admitted that she recognized his panty lines first and then the tell-tale bumps of his garter belt. For a long time he’d thought she was a run of the mill prostitute, even in a swinger’s club. But she had such a warm and easy way about her that he found himself telling her some of his secrets.
They’d exchanged emails. A follow-up dinner at a secluded restaurant brought the rest of his secrets to light and she revealed that she was a ‘fantasy maker’. While their arrangement would have to remain a secret from any legal authority she claimed that she was not a hooker. Somehow her veiled anecdotes of previous experiences seemed more than just trying to sell him on the proposal. He admitted he could have been completely deluded but he felt they had a real connection.
The rest had come together in a matter of days.
Glancing at the time, he only had a few minutes left. The experience he’d arranged was not one of submission to a cruel dominatrix. Nothing killed his desire and his erotic mind-state more than someone trying to hurt him or cruelty. No, Coleen would be in charge but sensuously and kindly. At least that was what had been arranged. Still he wanted to comply with her directions in every last detail to make sure nothing would upset the experience.
He walked out of the bathroom and on to the warm, soft carpet. Looking out through the breath-taking large penthouse windows he saw Chicago arrayed out beneath him in the setting sunlight. The Sutton Place Hotel had been an excellent choice and he loved her taste.
The robe slipped over his arms and shoulders like a caress. It was a women’s satin robe that fit him perfectly and he started to get erect.
The satin just felt so amazingly wonderful on his tingling skin that a moan escaped him. From his toes to his nose, his skin seemed so sensitive that even the light brush of the satin was thrilling. His skin definitely felt different but he loved it. The fleeting thought of masturbating caught his attention but Coleen had been very explicit about him not masturbating for two weeks up to their encounter.
The chunk of the suite’s door’s lock opening made him freeze.
The door swung open and she came in. Her perfectly straight red hair flowed past her shoulders. Her emerald green satin blouse was modestly buttoned but was still cut tight enough to showcase the curves of her large breasts. Her hips and legs were accentuated by a pair of tight jeans that looked like they’d been sprayed on. High stiletto heels clicked on the tile of the suite’s foyer until she reached the carpet.
The door drifted shut and locked behind her.
“James!” she smiled as she walked up to give him a warm hug. He hugged her back and shuddered as he felt her body against his own and the robe shifted on him deliciously. She gave him a kiss on his lips, not quick and chaste, but also not overly lingering. “I’m so glad you could make it. We’re going to have so much fun.
Her enthusiasm was a wave of energy over him and he couldn’t stop smiling himself. He watched her put her purse, the room key card, and plastic shopping bags on a side table, taking the quick opportunity to enjoy the view of her bottom, her curves, and that fluidly shifting hair. The bags were clearly from Victoria’s Secret, Frederick’s of Hollywood, and Cupid’s Boutique.
“Were the instructions clear enough?”
“Very clear and finished completely.
“Great! We can jump right in. Now remember we don’t have to rush anything. This isn’t a sprint. We’ve got the suite all night. Also, it isn’t a marathon. When you’re sated and tired, we can stop for the night. We’ll see how it goes. We might be able to catch a little sl**p together later. “
Just sl**ping with her sounded wonderful to him.
“As we discussed, I do have some techniques that are rarely used by others but I think really elevate the experience to something you’ve never reached before.
If you think back to the first time you touched panties and wanted to put them on… the first time you slipped your s****r Sarah’s panties on you… the first time you braved Victoria’s Secret to buy a teddy for yourself… That first time intensity is what we’ll be experiencing tonight. “
He nodded, not trusting his voice with his nervous excitement. His cock was rock hard and he hoped it wasn’t leaking against the satin robe.
She read his mind and glanced down.
“I think you’re happy to see me,” she gushed and that line between a purchased experience and sl**ping with a lover was blurred in his mind again. He’d been to Vegas a few times to try and have his fetish indulged. The experiences had been enjoyable but there had always been a clinical side to it all, an emotional detachment. He felt none of that with Coleen.
In fact, most of their dinner together had been talking about things besides sex. He’d really enjoyed her company.
She reached into her purse and pulled out a foil pouch. He recognized it as a condom. He gave her his hand as she got down on her knees, giving him a disarming giggle while she did so. She divided the front of the robe to reveal his smooth, hairless cock beaded with precum on the tip.
She reached out one red-nailed finger to catch the bead on her tip and then lifted it to his mouth. He opened and let her rub the precum softly on his tongue. She winked and returned to her knees.
“Such a beautiful cock, James,” she said softly, staring at it as her hands tore open the condom packet. “You must really please the ladies, so long and thick. ” Her words were like honey and he grinned at her praise.
“Here’s a little trick I learned that I think you’ll like,” she continued. She took the condom out of the packet and placed it in her mouth. After a moment of moving it around behind her lips, she opened her mouth and began to take his cock in between her lips.
He groaned in pleasure as he felt her teeth and tongue gently pulling the latex condom on his cock, stretching and unrolling it down his shaft as his cock disappeared in her mouth.
He closed his eyes and absorbed the sensations of her heat and wetness, her eager tongue. She was massaging his cock head with her tongue as her teeth unrolled the condom. His tingling skin made the pleasures even more intense. Looking down at her, her beauty, his cock disappearing into her mouth, he gulped and felt his orgasm rushing up on him.
“Wait, I…” he blurted but she continued getting the condom unrolled 3/4 way down his shaft when she couldn’t take any more of him in her mouth.
His balls clenched, sending his brain a blast of sexual joy and then throbbed and flexed, pumping out his cum. “Oh god yes…”
Coleen’s hands gently grasped his thighs and she kept him fully in her mouth as he came, moaning softly as she enjoyed the feel of his throbbing cock and the flowing cum. When his wave finally subsided, she helped steady him as he felt momentarily weak in the knees.
“I’m so sorry, I…” he began as she pulled her mouth off his cock.
“No, don’t worry, honey,” she cooed. “I’m pretty flattered actually. I’ve never had a lover come so quick in my mouth. ” The condom was still firmly on his cock and the end was drooping and heavy with his seed. She cupped the end, feeling the amount and heat of it. “That’s a lot of cum… we’re lucky. “
She carefully slid the condom off his cock, keeping the reservoir filled with cum carefully protected.
He watched as she walked to the suite’s kitchenette and got a glass. She poured the come into the glass, working the condom to get out every last drop. After fetching a fresh packet, she returned to him.
This time she slid his cock in her mouth without the condom and quickly cleaned it of lingering cum. His erection renewed quickly. She let it come out with a pop and licked her lips.
“I might just have to steal some of that later,” she teased before wiping off the remaining wetness and rolling down the new condom with her fingers.
“Come with me,” she said with a purr. He followed her into the bedroom of the suite where he sat on the edge of the bed. The pink satin comforter felt wonderful against his bottom and legs.
Coleen brought a chair over and placed it facing him.
She sat down and looked at him. Several moments went by as their eyes were locked before she spoke.
“Look at my breasts…” She slowly undid the buttons of her satin blouse, the green material slipping open further and further to reveal her large breasts held in the sheer black lace cups of her bustier which did little to hide her nipples and their hardness. The black satin bustier hugged her body tightly.
Sliding the shoulder straps of the bustier off her shoulders gave her enough play in the material to slowly work the lace cups down. Her beautiful breasts became fully revealed, round and firm.
Taking one hand, she gently touched her left breast, cupping and squeezing it. He could see her nipple stiffen further. “Do you like my breasts?”
“Very much!” he blurted and he could feel how hard he’d become.
She began to run one finger very slowly around her breast, in a circle around and around her nipple.
“Watch my finger… Each time it goes around, you’ll feel more relaxed, more comfortable with whom you want to be. ” The finger circled again slowly. “Relaxed and natural… relaxed. “
He opened his eyes after an odd blink to see her still circling her breast but from her face he could swear she’d just cum. Her free hand slipping out of her unbuttoned jeans added to that conclusion. He could glimpse black satin panties in the little gap in the top of the jeans.
After a few moments, she stood and put the chair back. She waved him to standing as well. “Take off your robe, sweetie. ” He slid the satin from his shoulders and let it slide fluidly down his body to a heap around his feet. Even the current of air of its passing felt wonderful on his skin.
Coleen walked to the other room and came back with the Cupid’s Boutique bag.
Leaving it on the chair, she pulled out a pink satin blindfold and stepped behind him to place it on him. She pressed into his body as she reached around to adjust it on his face, her breasts making him shudder with pleasure as they pushed against him.
Once the blindfold was secure he could see nothing but a very dim grayness. She didn’t leave but slid her arms under his and around to hug his chest.
Now he could feel the undone snap of her jeans against his ass too.
“Breasts are womanhood,” she began softly, talking into his ear. Her hands moved to his pecs and began to stroke him. They massaged his skin and he felt it all tingling. “Full of life they are very sexual. Full, round, supple breasts are beautiful, entrancing men and women alike with the desire to kiss, lick, and suckle them.
His chest was really tingling now and he felt her fingers pulling at his skin. Something was happening.
“Oh the pleasure they bring a woman… so sensitive and sensual… making her clit tingle when they are brushed and throb when they are worshipped…”
“Feel my full breasts against you; imagine how they would feel to have, their weight, their size transforming your figure into a gorgeous woman…” She was pulling more now and he felt a weight on his chest.
“Beautiful breasts inside delicate bras or bikini tops, always threatening to escape and be free, to be seen and admired, to be lusted for…”
He sighed as a wave of pleasure washed over him and he realized that she was cupping and massaging his full breasts. Blinded by the satin over his eyes, he could only strain to interpret the sensations, the way she would move them, lifting them and stroking them, the tingle he’d feel in his toes and balls when she brushed his full nipples.
He’d never felt these sensations before and he felt transformed.
“Oh god yes,” he breathed and she let his hands replace hers. He felt them, warm and real flesh, truly transformed to have the young, full breasts he’d always fantasized about. She stepped away and came back after a few minutes.
“Good girls wear pretty bras on their breasts,” she said softly, slipping the material around his waist and then pulling it slowly upward, letting the satin cups, the underwire, and the elastic straps all play against his skin.
She guided his arms through the shoulder straps and then brought it up. His breasts strained the cups as she fastened the back hooks but he thought the tightness felt divine. He’d worn all manner of bras and lingerie wishing he knew what they truly felt like full with breasts and now he was experiencing every bit of it.
His cock was throbbing with his heart beat and he knew that he was more than ready for another orgasm.
He realized that the cream Coleen had made him shower with had so heightened his sexy smooth skin’s sensitivity that every brush of her skin or pretty lingerie was amazing. It was a thousand nights’ fantasies come true.
Coleen loosened and removed the blindfold, letting him look down at his breasts in the pink satin bra. He continued to cup and stroke them happily.
“Oh my!” exclaimed Coleen gently. “You have no panties! Girls without their panties are just little cock-sluts, aren’t they?” His mouth gaped but just before he recovered to say something she continued, “We’d better get you a pair.
He nodded although it was a bit half-hearted. He wanted the panties but being a little cock-slut sounds pretty good to him too. She fished a pair of pink satin string bikini panties out of the Victoria’s Secret bag. He noticed they had the same black threaded ornamental stitching that he saw on the bra itself.
She knelt behind him and nudged him to turn a little so he could see himself in the full mirror.
His hands were still cupping and feeling his breasts as he let her lead his feet into the panties. Then her hands pulled them slowly up his legs, letting the satin, the ruched elastic waist, the soft cotton gusset stroke his skin. He was trembling with pleasure as the panties reached his upper thighs.
“There is nothing,” she began as she started to pull the material into place. “like the feel of satin panties, tight on a girl’s bottom…” The waist pulled up and he felt the satin slide up and then taut over his own bottom.
“And delicately over her pussy…” Her fingers brushed his asshole through the satin, tucking a little material between his cheeks.
She left the material bunched under his cock. There was no way it would nestle inside at its current state of raging erection. He owned plenty of roomier pairs of panties at home but they always fit him like a bag. He didn’t want to give up how perfectly these panties seemed to fit him, touching his skin the right way in every place.
Moving around to his side, she pulled another pair of matching panties out and lifted them over his cock. He watched everything in the mirror as this beautiful woman d****d the panties over his condom-wrapped penis and then began to stroke him with her hand.
“Pretty girl wanna cum in my panties?” she asked him. On top of the sensations racing through his body, those words blew his control.
“Oh god yes yes yes,” he blurted as his balls clenched fiercely, electrifying his body with pleasure and then throbbed with powerful contractions and even more cum shot into the condom.
He had to sit on the edge of the bed before the orgasm began to subside as his legs had gone silly on him.
“Mmmm, good girl,” mused Coleen as she stroked all of the come out of his cock into the condom. She tossed the panties on the bed and teased the hanging bulge of come in the condom with her tongue as she looked up at him. One final ejaculation boiled up at the sight of that, pouring out, and then he was spent.
She quickly handled the condom and cleaned him with her tongue. Finally, his body was relaxing and his cock got soft. She deftly pulled the panties in place and smoothed the front of them with her hand. She kept pulling them a little this way, a little that way, tugging on the waist band, until she asked him to stand again.
“Do you like your panties?” she asked. He stood and looked in the mirror.
He was stunned. He was looking at a beautiful woman with full breasts and panties smooth over her pussy. He saw no bulge in the panties at all and they looked perfect.
Coleen stepped behind him and tugged in the waistband a little on either hip until the satin was perfectly smooth between his legs. “You look good enough to eat…” she whispered.
He had to sit on the bed.
As soon as he sat he had to lie down. His head was spinning in amazement and a rush of arousal. When he looked up, Coleen was slipping out of her blouse and heels and peeling down her jeans. She was left in a black satin bustier and matching satin thong panty. She climbed on to the end of the bed.
“Janey, you are such a beautiful girl, I just have to have you,” she purred and then he watched as her head dipped down between his legs.
He felt her hands stroke his thighs and urge them apart. He felt his panties shifting as he complied, stroking his electrified skin. His breathing was ragged in his excitement. She urged him further up the bed until he was propped up on pillows and she could comfortably lie with her head at his panties and he could watch everything.
His panties had pushed down a little when he scooted up and he watched Coleen nose against the satin of them, rubbing them against her face.
Her fingers snaked up to tug them back into place and pull them tight enough that he saw the outline of a perfect pussy through the satin. He could hardly breathe.
She caught his eye and watched him as her tongue extended and began to touch his pussy through the satin panty. Her tongue moved in a circle over the material and he could feel it rubbing his swollen labia, the tingling and pleasure of it, of seeing her kissing his pussy.
His previous eruptions were still dragging on him so she was able to lick and suck him through the satin for over ten minutes as he squirmed in pleasure and moaned his appreciation. The only chance to relax came when she shifted him and settled over him into a 69 position.
He eagerly grasped her ass cheeks and put his own mouth to her panty-covered pussy. Her panties were soaked with her arousal and he loved the taste of her sex.
Soon, her hips were squirming like his as they moaned and moved together. Her toned stomach pressed against his satin-covered breasts while her breasts pressed and moved against his bare skin.
“Oh god, Janey, come with me,” she moaned. There was a several second pause and then, “Pretty girl wanna cum in my panties?”
He felt his body clenching and throbbing, pleasure washing over him from nipples to clit to toe to his lips.
Over and over it rose and spread over him. His hands felt Coleen’s body doing the same thing, muscles contracting and relaxing as she came. Her panties got wetter and he eagerly lapped at them.
After a minute of lying in that position, Coleen shifted around to lie with him face to face. He loved the way their feminine bodies and lingerie felt together but he was also entranced by her. He watched as she lapped up some pearly white cum from her lips and swallowed it with a smile.
He knew that he dozed a little that way, spooning with her arms around him and her breasts against his back, her breath in his ear and her hair brushing his shoulders. He’d never felt so feminine and so happy.
He didn’t feel that too much time had gone by before she slipped her arms from him and got up. He watched her stretch, her curves moving smoothly. She brushed out her hair with her fingers until it was all flowing straight again.
“I’ve got more pretty things for you, Janey,” she smiled. “You ready?” He nodded and sat up in the bed. She padded on bare feet over to the bags in the salon and returned with the remaining bags.
“We girls need to always look our sexiest,” she began as she pulled out some plastic-wrapped packages of thigh high stockings and some garter belts. “Now watch me and then you’ll dress yourself.
She brought the chair back over to the bed and sat on its edge. After she unwrapped the package she drew out two thigh high silk stockings. She took a moment to indulge herself and stroked her cheek with the soft material. Next she picked up six garters which she proceeded to clip to the bottom of her bustier. Each was black elastic ending in shiny silver clips. She stood to clip them on and have them hang properly.
Sitting again, she rolled one of the stockings up over her hand in a delicate bunch. Pointing her left toes, she slipped the bunch over her foot and drew it carefully and evenly up her leg. Wrinkles in the silk disappeared one by one until it was simply a sheen over her lovely skin. Standing, she carefully attached one… two… three garters to the stocking. The first ran to the inside of the top of her thigh in front.
The second ran over her hip. The last curved to hug her bottom snugly. The black lace on top of the stocking pulled taut with the garters.
“Maybe you should put my other one on me,” she mused. She held out the second stocking and he took it, his fingers trembling with arousal. He mimicked her motions, ones he’d practiced on his own for years dolling himself up time and time again.
She held out her foot and he slipped the silk over them, carefully drawing the stocking upward. He made sure he didn’t snag it and ruin the perfection of it.
When he’d pulled it snug up to her thigh, she rose, leaving him kneeling. He swore he could feel the heat of her sex and smell the perfume of her arousal. He began in the front and kissed her thigh just above the stocking.
After a few soft touches with his lips, he pulled the garter and clipped it to the stocking.
Moving to her hip, he repeated the process, kissing her skin longer before drawing back and shutting the silver clip over the lace. She turned to present her bottom to him. He saw the narrow elastic disappear between her cheeks leaving her virtually naked before him. Smiling, he began to kiss.
This time the kissing was no momentary diversion from his task.
He nuzzled and suckled the slight crease where her perfectly round bottom became her thigh. He kissed up her cheek, all over the soft, warm skin. He reached the back of the thong and caught the elastic with his teeth, pulling it gently again and again, working it between her cheeks. Her throaty moan was his reward.
His lips journeyed to her other cheek, all over. His finger lifted the clipped garter to not miss a spot.
Slowly, he moved closer to her crease, the heaven point at the crux of cheeks and thighs. He slithered his tongue into the crux, brushing the elastic and tasting it soaked with her juices. He inhaled all her aromas, pressing his lips between her cheeks. His tongue sought deeper and when he touched her anus, it flexed and she gasped.
She hurriedly got on the chair on her knees, facing the back and bent down over the top of the back of the chair.
Her knees were spread as wide as the chair allowed. She practically yanked her thong down until it caught against her garters at the top of her stockings.
Grasping her thighs, he pressed his face again to her, enjoying more freedom of movement now. With his nose spreading her cheeks, he moved deeper until his lips touched her anus and kissed it. He felt her shudder. His tongue snaked out and probed her, coating her with his saliva and urging her to open.
Slowly he felt her relax and his tongue pushed into her hot, raw flesh. He worked slowly, working more and more saliva in until his tongue could thrust into her with perfect ease.
“Oh god yes, do it,” she gasped. He felt her touching her pussy and possibly her breast as well. He shifted slightly, enjoying the weight of his own breasts and the way his curvy body moved. He slipped one of his hands free to cup and squeeze his breasts, still amazed at the transformation and how good it felt to finally feel what he’d dreamed of for years.
Putting his pleasures aside again, he slid his hand up between her legs and stroked her labia as his tongue thrust in and out of her ass. His fingers became slippery in an instant and a slight shift was all it took before two of them were thrusting in and out of her pussy.
“More, yes, please, more fuck me…” she begged, her fingers swirling around her clit. He added a third finger and felt her have to stretch to accommodate all three.
Thrusting with fingers and tongue, she moaned louder and louder until her body clenched up. He had to work hard to keep his tongue from being expelled from her ass. Not a second later, her orgasm crested and he felt her ass clenching over and over on his tongue just as her pussy grabbed at his fingers. He’d never stopped thrusting and she rode him, her hips grinding herself against him.
He lost track of exactly how long she came but she finally pulled away from him to drop into the chair, her panties still around her thighs and her face still flush with pleasure.
“You continue to surprise me, Janey,” she grinned as she ran her fingers through his hair.
He carefully attached the final clip to her stocking and pulled her thong up and into place around her pussy. She relaxed as he stood and slipped another pair of stockings from her pile along with a pink satin garter belt that was obviously part of the set he was wearing. It had six silver clips matching Coleen’s set.
Watching her carefully, he went through the delicate process: rolling, unrolling, smoothing, pulling taut, and snapping the clips. When he was done he had to walk around the room, feeling the delicious silk pulling at him, the garters taut over his panty-covered bottom, the swish of his legs.
“You’re missing something,” said Coleen as if she were pondering. He turned back to her to see her holding a pair of black ankle-strap high heels dangling from a finger.
He grinned and swished his way back to her. He sat on the bed and she went to her knees to slip each shoe on his stocking-covered foot after first kissing his toes. The shoes slid on and felt perfect. He felt very excited as she buckled the ankle straps on him and stepped back.
He stood up and began to strut, out into the salon in back, each foot placed perfectly in front of the other, shifting his hips in time to give his ass that little bounce women in heels get.
His calves felt stretched and slender, arched by the shoes.
“You little slut, you know how to walk in heels!” laughed Coleen. He smiled back, flipped his head as if his hair was much longer and did a catwalk turn.
“You watch enough Victoria’s Secret Fashion Shows and you get a clue. Then its just practice,” he said happily. He loved the way his body was moving, the shifting of his breasts in the bra, the swing of his hips.
Even his ass seemed toned, firm, and deliciously curvy.
“We’re almost there. ” Coleen stood up and walked over to the bags. She’d slipped on her own pair of high heels though he noticed hers were higher than his, almost 5″ of thin heel. She opened the Frederick’s bag and drew out a voluminous satin dress, full of puffing, lace edging, flared skirt and taffeta petticoat. It was 100% fetish and he loved it.
“This is going to feel better than it ever has before,” she whispered in his ear before kissing him and stepping back to arrange the dress. Using her shoulder to steady himself, he stepped into the dress as she held it open for him. He took care not to snag the material with his stiletto heels. Once his heels were back on the ground and clear of the material he let go of her.
“Watch yourself in the mirror,” she said quietly. He drank in his beauty, the stockings, the flat feminine panties, the full breasts in the bra, the high heels. If he wasn’t mistaken he even looked like he had makeup on, pushing the transformation toward absolute heaven.
The dress was bulky enough that Coleen had to work at it a bit to bring it up his body. It moved very tight past his hips and bottom and then snug against his torso.
He slipped his arms into the sleeves and she pulled to get it into place. He felt a little out of breath with how tight the dress as but that felt perfect. Skin-tight dresses are what he’d always dreamt of wearing and now he could do the dress justice.
She pulled the top up and over his breasts. The material was tight enough to give him glorious cleavage in the scoop neck of the dress.
A quick click of some hooks behind his neck and she was done.
Coleen stepped back and let him admire himself in the mirror. He turned this way and that to see the dress and his body from every angle. He cupped and pushed his breasts. He smoothed the skirt down over his curvy bottom only to have it flare again from the stiff taffeta. Every swish and shift of material made him more and more excited.
The dress was tight and really showed off his transformation to a voluptuous woman.
He felt flush and light headed as his hands slipped down to get under his dress in front. His panties were soaked and he quickly began to stroke his pussy. His sensation overload sent him to orgasm in mere moments; moaning loudly in the room and feeling Coleen slip her arm under him to steady him. His whole body spasmed in pleasure and joy and he never wanted to stop stroking his clit.
At last, he relented. When he could stand, Coleen slipped to the salon for a moment before returning and fussing with his pussy for a few moments.
“This is the moment I’ve been waiting for, Janey,” explained Coleen facing him. “You are gorgeous and femme now and you deserve to become a real woman in every way. “
He swallowed as his mind raced with the possibilities. At her bidding, he knelt and the blindfold was returned over his eyes.
He waited a minute or more before he felt her near him again. Her finger tips brushed his face tenderly.
He waited a little more and then he felt her fingertip rubbing something on his lips. His tongue slipped out to taste it and tasted cum. He flushed with latent embarrassment but licked it up regardless.
“Every real woman has a slut inside her, a side of herself that wants to get and give pleasure, which wants to drive a man wild for her.
Every real woman craves cock, honey. She wants to feel it in her mouth and feel it throb. She wants it to pour salty cum in her mouth. Do you want to be a real woman, Janey?”
“Oh yes,” he began and then felt the tip of a warm, very real cock touch his lips. He stopped speaking but he didn’t close his lips.
“Suck my cock, Janey,” moaned Coleen. “You know how you like it, how it feels when I sucked yours.
Open wide to keep your teeth from scr****g me and enjoy. “
He could hardly breathe as the hot, tender flesh pushed against his lips. He opened wide and took the head in his mouth. He let his lips close around the shaft just after the head and he began to lick the head. His first taste of precum nearly made him cream his panties. He’d wanted this so long… to be completely femme and pleasure a big cock.
Past images of porn blowjobs came to his mind unbidden along with watching Coleen suck him. He opened his eyes and looked up at her, her face partially hidden by her breasts. He smiled widely to let her know that this was everything he wanted at this moment, to suck and please her.
Glancing down, the cock seemed enormous right in front of his face. It was hairless along with her tight balls.
Her panties were tucked under the balls, lifting them up toward the shaft.
He bobbed his head on the shaft, slowly testing how far he could take her in him without gagging. He pushed himself, recalling the times he’d practiced on a soft dildo aching for this chance. Further and further he pushed his lips down the shaft until he felt the big head push into his throat.
He couldn’t breathe but he pushed another half inch until his lips fully pressed against her skin at the base of her cock and then he popped back off.
“Holy shit, James! I mean, Janey,” gasped Coleen. “You’re a natural cock-sucker!”
He winked at her and began to bob again on the upper part of her length while stroking her with his hand on the lower part. His tongue was everywhere, lapping, stroking. He would seal his lips around her head and suck until his cheeks pulled in, desperate to bring out her cum.
This continued happily for nearly fifteen minutes when his jaw was starting to ache from all the effort.
He started stroking her firmly and fast with his hand while his lips and tongue zeroed in on her head.
“You’re going to make me cum!” she moaned, her hands working her breasts firmly.
His mind was awash with pleasures and satisfaction, and amazement at this experience and a desperate need to cum again. She started bucking, fucking his mouth with her cock and he held still with his hand a firm tunnel on her shaft and his mouth a tight hole for the head.
“Pretty girl… wanna cum in my… panties,” she choked out before giving into a wail as she came. He came at the same moment. His body flashed with pleasure from his clenching pussy to his nipples and everywhere. He felt her cock swelling and then throbbing, her balls clenching against his hand.
And then the cum erupted! Hot, salty, slimy, sexy cum! Spurt after spurt flowed into his mouth. He literally had to swallow quickly and still his mouth filled up even with the tip of her cock only barely past his lips.
When her flow slowed, he snaked a cum-coated tongue out to lap up the last dribbles of hot seed from her cock. She flopped back on the chair in front of him, spent but glowing with her orgasm.
“Show me the cum, Janey,” she urged with a wicked smile. He opened his mouth and sloshed the pool of cum around for her to see.
“Swallow it. Swallow every last drop…”
Shuddering with aftershocks of his own orgasm, he happily complied; the cum sliding easily down his throat in to his stomach.
He swept his mouth with his tongue to get it all off and sucked it all down. He opened his mouth to show it was clean though he could still smell the potent aroma of his service to her.
“Next time, maybe I’ll cum on your breasts and let you lap it all up?” she mused. He flushed in embarrassment while grinning big.
“It’s getting late,” she finally concluded. “Let’s go to bed.
” She pulled up her panties which now had a large bulge of her flaccid cock in them. She took off both their high heels and helped him out of the dress. They took off their stockings and garters and stripped off the other lingerie. She did have him keep the bra on.
“You’re not used to sl**ping with a pretty rack like that. The bra will help you keep ‘the girls’ in check,” she explained.
When she was down to her panties and he to panties and bra, she pulled out the last present: matching soft pink satin nighties. He realized that they were the same height out of heels and probably the same size in clothing, at least with his new figure. Regardless, they both looked smoking hot with the satin dr****g their bodies beautifully.
After shutting off the lights in the penthouse, she drew back the comforter to reveal satin sheets and they slipped into bed together.
“Was it everything you’d hoped for?” she asked after a few minutes.
“Far beyond my wildest dreams,” he confessed. “I don’t know how you did it, but it’s just wonderful. I’m so glad I could experience it… with you. “
She snuggled closer to him, spooning against his bottom and pressing her breasts into his back. “Me too. “
She gave him a kiss on the cheek and he drifted off into restful slumber.
Early dawn light was starting to filter into the room when he woke up. For a moment he was disoriented and then everything rushed back to him. He couldn’t help but smile.
Still, things felt different now. For starters, he was sl**ping behind Coleen, his arm d****d over her waist. And it didn’t take much movement for him to realize that he felt very… normal. Gone were his large supple breasts and his cock had found some morning wood nestled against Coleen’s ass.
At least they were still dressed in the pink satin nighties.
He didn’t want to move and wake her. He felt like he was in a frozen moment, peaceful and happy. The light grew slowly the room moved from shadows to grays to pale colors. Sitting on the nightstand next to the bed was a large strap-on cock and a dirty glass. The glass was the one she’d been saving his cum in and it looked like it had been quite full last night.
Even slight movements against the satin sheets told him that he was still baby butt smooth all over. He pressed his cheek to his shoulder and felt the barest hint of emerging stubble. He moved his tongue around his mouth and knew that he’d really had cum filling it and he was sure he’d swallowed all of it. Now he needed a toothbrush or at least a mint.
“Regretting anything?” she asked softly, not moving from her position cuddled back into him.
“No…. well, maybe just one thing. “
She shifted on to her back and looked at his face. His fingers passed over her clearly cock-less panties and ended up across her body with his hand lying gently on her breast through the nighty.
“Last night was… so special and powerful that I could never thank you enough. You really brought my dreams to life in a way I never thought possible.
I don’t know how you did it, but I guess… I guess I don’t really want to know. I don’t want to spoil the magic. “
“It was special for me too,” she smiled, running the tips of her fingers along his forearm.
“But something else was happening, Coleen. From the moment I met you, all through our dinner together, making the plans for last night… I guess you could say I was smitten before you unleashed my fantasies.
Right now all I can think about it not getting to see you again, to see you smile, to learn everything about you. “
She was quiet for a long time but he held his tongue. He needed to hear how she felt.
“So you’d rather go to the movies together than have me doll you up and transform you?”
“What happened last night was magical, powerful more than I can describe.
But yes, I’d leave it as the once-in-a-lifetime experience that it was if I could take you on a date. If we could have a chance of seeing if there is something more powerful between us. “
She looked into his eyes so long that he could see her irises change colors as the dawn light strengthened. Finally, she leaned over and kissed him on the lips. It was a soft, tender kiss full of possibilities.
“How about Friday night?”
He grinned wide and kissed her back eagerly, pulling her to him. They both laughed and held each other.
She slid a hand down his back, over the satin nighty and down to his panty-covered bottom. His cock stiffened noticeably against her leg.
“I’m guessing that you wouldn’t refuse to play dress up too?” He moaned in obvious appreciation, pulling her tight to him, his cock pressing urgently against her.
“Good guess…” he whispered before kissing her.
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