Karen – Dress-Up (F/m)


(Male Version)

It started as a simple game.

“Would you like to play dress-up?” she asked, giggling. That childish giggling that made him melt. So innocent. So contagious. So lovely.

He raised his eyebrows in surprise. He would do anything to please her. But…

“Play dress up, Karen? Isn’t that a little… childish?” he asked.

“Oh, I’m not talking about this kind of dress-up, Pete. I’m talking about the… adult kind.” she said, her voice changing into a sexy whisper. It was still followed by her giggling, but it was much more mature. Much more sexy. Almost devilish. Devilishly sexy.

“I…” he began to say, searching what to say, how to say it. He would rather play dress-DOWN than dress-up.

“I’ll go first.” she said, smiling, her voice becoming sultry, hot, whispery, and her eyes lighting up, like ready to strike.

Oh she did strike, alright. Right on his groin. She noticed it growing under his jeans.

“Just wait here.” she said, entering her bedroom. The last thing he saw was her butt, wiggling in her tight jeans, before the door closed, softly, almost silently. Teasing.

He stood there, in the middle of the kitchen of her apartment, wondering. It was only their fifth date after all, and the first time she invited him to her place. All the other times was at a restaurant, or at the club. On this date, he felt confident. He invited her to his place, but she refused.

“Lets go to my place instead.” she had said with that giggling. “It will be more fun there, I’m sure.” she had added, again her voice changing, almost like a predator about to strike its prey.

“Ah… Yes. Sure. Why not?” he had said, thinking about the wine he had specially chosen for that occasion, the rose petals he had put on the satin bed sheets he had bought especially for that. The soft playlist he had chosen, ready to play at the touch of a button. Even the dimming of the light has been well rehearsed. 

He hadn’t been very lucky in love lately and he felt that Karen was the one. She had that little je-ne-sais-quoi that attracted him like a moth to a light. Was it her laugh? Her smile? Her eyes? Her tight jeans? Her heels? A mix of all of it?

He wanted so much for things to work out with Karen. He was willing to do anything. Well, almost.

“Just a few more minutes” she said, slightly opening the bedroom door and poking her head in, not showing anything of her body, although he thought he saw her fingers. Sleek, black, like in a glove. A shiny glove.”

“Uh… Okay.” he said, his voice shaking.

Shortly after that, the door opened, and he saw a feet, wrapped in a strappy, sparkly high heel sandal, a change from the wedge heels sneakers she was wearing a few moments before.

The feet got up and down, then he saw a leg, a long leg, almost wrapping the door frame as she got out herself, hugging the door frame, rubbing her body against it.

She was wearing a tiny red bikini and black shoulder length gloves. All very shiny.

She softly, sexily, approached him, moving her hips in an exaggerated manner, lowering her head, slowly moving her shoulders, looking at him in a sultry, almost scary manner, smiling. For a moment, he thought she had become a tiger.

His brain almost hit the overload. Darn! She was so sexy. She made a gesture of her finger, telling him to approach. He did, almost like a zombie, hypnotized by the sight. He touched her, touched her shiny bikini. He knew what it was. 

“Hum! Latex. I like that.” he said, rubbing his big hands on her breasts, feeling the latex, feeling the mammary glands, gently squishing them as he reached for her mouth, for a hot kiss.

She received his tongue, but at the same time, her hand reached down, to his crotch. She slipped her hand inside his jeans, taking in his throbbing manhood inside his latex gloves hand, going down to his balls, then gently squeezing them. He liked the feeling of the latex touching his penis, his balls. Soft. Sleek. Exciting.

“Well, your turn.” she said, taking her hand off, and softly scratching his chin with her other hand’s index finger, making the ‘follow-me’ gesture. “Come…” she whispered from her hot breath. He almost melted there, on the spot.

It was as if this index finger was pulling an invisible leash. He followed her to the bedroom. It was a very womanly, girly white and pink bedroom, with the bed covered with white and pink satin sheets. The white desks were covered by stuffed toys and porcelain trinkets. So girly. That’s what he expected from a sexy girl like Karen. He liked it.

She picked something in rubber from her bed and showed it to him.

“Well, your turn, bad boy.” she said, showing a pair of latex panties, but with two tubes. One going outside, and another one inside.

“What are those for?” he asked.

“Well, this one is obvious.” she said pointing at the external one, with the little pouch for his balls, “ and this one is, well… for the plug.” she said, her eyes turning almost evil. “If we come to that.” she added, whispering to his ear as she got closer to him, putting the garment in his hand, reaching for his jeans and expertly undoing the button with one hand while the other was unbuttoning his dress shirt, all while she was passionately kissing him.

Hand shaking, he took up to the task, at the same time, not willing to let go of her tongue in his mouth. She gently pushed him.

“In good time, Pete. In good time.” she said, giggling.

He never undressed that fast. In a flash he was standing naked in front of Karen. She approached, pouring some lubricant in her rubber  hands and spreading on his manhood.

“Will be a lot easier to put on.” she said, picking up the already well lubricated garment and helping him pull it up his legs. While kissing him, she directed his erected member inside the penis sheath. It was a tight fit and he felt the tight rubber gently squeeze his penis.

He liked that. She went behind him, using her finger, gently pushed the butthole sheath up his rectum.

“Not exactly…. Pleasurable.” he whispered.

“You’ll come to like it, Pete. Don’t worry.” she softly whispered, getting back up, picking his erected latex manhood in her gloved hand and gently stroking it.

The latex of her hand slid easily on his latex coated penis, sending tingling waves of compression and release. His breath began to shake.

“You like that, don’t you?” she whispered in her ear.

“I would be lying if I said no.” he said, gently grabbing her head and aligning with his to give her a kiss, while he tried to lead her to the bed. He was ready to roomba, and with the thick condom he had on, plus Karen’s internal condom, he was not thinking about any added protection.

“Not so fast, boy.” she said, giggling. “Dressing up is more than putting on underwear.” she added, gently pushing her away. She went to her desk and picked up two large pieces of rubber and handed one to him.

“Here. Take this and… follow the leader.” she said, again giggling, this time her brat giggle.

He unfolded the rubber garment and it unrolled into a complete catsuit, with attached gloves and toe socks. He was turning it on all sides, but the only zipper he could see was at the crotch.

“You… You don’t put this on through the crotch, don’t you?” he said, puzzled.

“No, through the neck.” she said, stretching it and feeding one foot inside, having already removed her shoes. Her suit didn’t have attached gloves or feet, and her foot easily popped up at the other end..

He tried to do the same but his balance was not as good. He settled in sitting down, slowly feeding the cold and stretchy material up her leg. This was a lot less sexy looking then Karen’s way of putting it on.

“Geesh. That’s quite tight. Sure it will fit me?” he asked, realizing how much he had to stretch the collar to get it over his large hips.

“Yes, it will. No sweat.” she softly said as she was already pulling her gloved arms through the sleeves and in amazement, he saw the suit ride up, engulfing her curvaceous body in its tight and shiny black embrace, almost enhancing every curve.

She helped him get up and pulled the suit over his chest, helping him fold his arms and get them inside the sleeves, guiding the fingers of his right arm into the attached gloves.

With his left arm in, he now felt the suit riding up, squishing his body everywhere, equally. He didn’t feel any kind of tugging.

“Told you it would fit.” she said, smiling, getting her hand to his crotch and opening the zipper, letting the throbbing member rush out in its own latex coating.

“Very good.” she said, kneeling, taking the large rubber shaft into her mouth and gently stroking it, pushing it deeply.

That was good, but at the same time, it felt… disconnected. He could feel the pressure, even the teeth, but not directly. It was like he was wearing a glove. A penis glove.

He reached for her head, feeling her hair though his latex wrapped fingers. They were clinging to it, getting entangled. Latex and hair don’t make a good match. She softly rose back up, hiding the fact that he was inadvertently pulling her hair.

“All in good times.” she said.”, sultry walking back to her desk where she picked up another large piece of rubber: a corset.

“Care to lace me in?” she said, as she wrapped the large garment around her already tiny waist.

Pete obliged. He felt powerful. He felt strong. He pulled hard on the lace while the woman of his dreams was putting her hands on the sides of her waist, moaning with each pull, evidently enjoying being crushed like that.

He couldn’t believe that the large gap that was there at first had practically vanished as the two sides met.

He tied a strong knot and had her gently turn around, as he felt her tightly encased waist in the unforgiving heavy rubber garment. He raised his hands to her breasts, gently squeezing them from their tight latex enclosure with his own latex enclosed fingers. The feeling was special. Not what he expected. Well, he didn’t know what to expect.

He was feeling her breasts, but at the same time, it was just like a firm balloon. A firm rubber balloon.

She picked another large item from the drawer of her desk and showed it to him.

“Good. Your turn, now.” she said, opening the large leather garment. “I’m sure you’ll look good in it.” she said, as she gently began to wrap his waist with the leather corset.

He was not sure, trying to hold the garment, but at the same time, not holding it.

“Now, just let it… embrace you, like a gentle yet firm hug.” she said, beginning to lace the garment.

He felt his waist getting squeezed.

“Expel.” she said. “Fully.” she added, her voice changing to a long and soft blow in her ear.

He did, sucking his stomach in as much as he could while she gave a yank he didn’t think she was able to do, considering her small frame.

“It’s all in the wrists.” she said, as if she had heard his silent comment. “That should do it. We can always come back to it later.” she said as she tied the laces.

“Later?” he asked. “Am I going to shrink?”

“No, but your organs will move.” she said, “only about 4cm to go.” she added, stepping her feet into her high heeled strappy sandals.

“Well, my shoes are on. Time to get yours.” she said. “Oh, no, I will provide.” she quickly intervened as he was about to aim for his own sneakers.

She opened one of the lower drawers of her dresser and retrieved two ankle high booties. He frowned.

“You’re kidding, right? Those are women’s shoes. I… I can’t wear those.” he said, eyes wide.

“Well, as they say, you have first to try before saying that you can’t.” she said, gesturing to him to sit on the edge of the bed.

He did, It was strange feeling the soft satin of her bed cover though his latex sin. She kneeled in front of him and proceeded to put his feet inside the dreadful footwear.

“How do you know it’s the right size.” he asked, trying to weasel his way out.

“Remember at the club, I wanted to have a closer look at your sneaker?”

“Yes… oh.” he said, figuring it out.

“So, yes they will fit.” she said as she began to lace it, tightly, then did the same to the other one.

“Here, slowly.” she said, taking his hand and pulling. He took a hold on the bed, turning facing it, bending forward on it, trying to stand up then immediately falling back on his hands.

“Damn! I don’t think I ca… what the fuck?” she startled as he felt something being pushed up his ass while he was ‘bending over’.

“You’re in the perfect position for the butt plug, dear. Just relax, it will go easier.” she said as she pushed harder.

He couldn’t run away, not with this footwear. Damn, now he couldn’t even flee her apartment! He felt the rather large intruder stretching his rectum, He was afraid it was about to rip open. She was gently, yet firmly pushing it in.

“Just relaaaax.” she whispered softly, then feeling the opportunity, she gave a strong push. He moaned, but it was in, as  he felt his rectum close around the narrowest part of the plug, and then closing the crotch zipper of the suit from the back down to where his latex covered erect cock was still protruding.

“Feels… feels like I have a dump half way out.” he said, blushing, trying to reach it with his hand.

“No, no. Do not touch it.” she said, slapping his hands. His face conveyed that he was quite uncomfortable.

“Here.” she said, pushing him forward on the bed where he landed on his stomach. “Let me help with that urge.” she said. 

Sitting on his legs, she grabbed his wrists and wrapped something heavy and large on them, fastening them tightly. He then heard a series of clicks as his wrists were brought together and locked into wide leather cuffs.

“Just stay put. I have two more to put on.” she said, gently sliding off him and wrapping more leather cuffs on his ankles, then locking them, and linking them with a short chain.

She slowly helped him turn on his back and then sit on the edge of the bed.

“Oh? And… how about you?” he asked with a grin.

“Of course!” she said, picking up a set of leather cuffs, putting them slowly and tightly on her wrists, ankles and even her upper arms and tying them tightly, before adding a little lock to every one of them.

“There. All cuffed and locked.” she said.

“Yeah but… you’re free.” he added.

“But of course, dear. If we are both impaired, where will be the fun?”

“Ah… of course.” he said, lowering his head, feeling that he had the low-end of that deal. “Anyways, when my time will come, you will have even more… anchor points.” she said, gently rubbing her elbow cuffs.

He simply looked, evidently making scenarios in his head of how to use those cuffs when it will be his turn at tying her up.

“How about we try that corset one more time?” she said, helping him get up on his wobbly legs. “Now, I’m going to untie your wrists. You think you can behave?” she asked.

“Yeah…” he whispered. The latex, the corset, the boots, the cuffs, all that was overloading his senses.

“Good, now put your hands way over your head and stretch upward as much as you can…. Perfect.” she said as she gave the first of many strong yanks, often putting him off-balance on his extreme footwear.”

“It’s going well, just a few more squeeze… Expel…. Again… Perfect!” she said as she knotted the laces.

Pete put his hands on each side of his highly compressed waist, feeling the rigidity, the tightness. This thing will not yield anything.

As he turned to his side, he saw his own reflection in the mirror. He was stunned! He never thought he could look so… sexy? Sleek, shiny body, thin waist, long legs.

The buttplug was annoying him. He reached for it, but she was quick to grab his hands and tied them back in his back again.

“Oh, no, naughty boy. You don’t play with the buttplug.” she said, pushing him on the bed again, where he fell on his stomach, laughing. “I’ll go get the last item, a wonderful latex hood.” she said walking away to the dresser.

He had landed on his hard erect cock, wrapped in this tight rubber. He unconsciously started to rock his hip up and down.

“What are you doing?” she asked with a hard tone. “Oh no, you’re not.” she quickly added, walking to the closet where he couldn’t see her.

She came back. He felt something hard being pressed against his butt, between his legs and something put over his corset.

“Turn around on your back.” she ordered.

He did.

He saw a steel band being wrapped around his tiny waist. She yanked on it, as it was a tight fit even over his corset, and snapped the two ends together.

Reaching between his legs, she grabbed another steel strap, then took his erected cock and forced it into a tube from the front flap. It was painful.

“You don’t play with yourself, dear.” she said as she yanked the front flap of the chastity belt upward, forcing his erected penis painfully downward into the tube and locked it to the belt.

“Now, get up!” she said.

That was painful, as much as her backward folded erected cock as well as the buttplug being pushed in. He struggled with the tight corset and his arms tied in his back, but he had no real choice.

She took the rubber hood she had thrown by his side and walked back to the dresser with it, taking another one.

“Apparently, I will have to go harder on you.” she said, coming back with what looked like a heavier garment and walked behind him.

“Open wide.” she said as she pushed a long and hard rubber lump inside his mouth and then wrapped the latex hood over his head. He felt it getting tighter and tighter as she struggled to pull the zipper down on the obviously too small rubber hood, which only pushed deeper the rubber gag filling his mouth.

Without a word, she walked back to the dresser and came back with a large leather band and a… gasmask?

She wrapped the leather band, a large collar, around his neck, hiding the zipper of the hood and forcing his head erect.

She then, without any explanation, added the gasmask over his head, pulling the straps tightly.

“For one, one never knows the harmful chemicals that are present in the air, and for two, it allows me to do this.” she said as she put his hand over his air intake.

He struggled to breathe, walking away, closing his eyes. His cock had reacted, painfully, in its confinement.

She smiled.

“Even better.” she said, snapping a leash to his collar and giving it a gentle tug, leading him out of the bedroom.

“Come, darling. The night is young.” she said, slowly walking, waiting for him, impaired by the high heel boots and the hobble chain to follow.

Once in the corridor, she let go of the leash and walked to another room. She pushed the door open and the corridor, as well as her shiny suit was flooded with a reddish light.

“This is the, shall I say, playroom. You want to get out of this and have your turn on me? Just join me here.” she said, smiling, then her smile changing for a devilish grin. “I give you two minutes. Every 10 seconds late is one more hour before you get your freedom back.” she said, then smiling again, she entered the room. “Time is ticking…” she said, joyous.

He struggled to walk, counting in his head.

“One Mississippi, two Mississippi, three…”

The butt plug, the chastity belt, the corset, the hood, the gasmask, the heels, the latex enclosure, everything was a distraction.

He was getting to the door, but had lost the count. Was he on time or late? If yes, how much late.

Finally, he reached the door frame.

“You’re almost out of time, dear,“ she said, awaiting for him in the middle of a real medieval torture chamber with crosses, benches, stocks, frames and enough attachment points to fill the room with a spider’s web of rope.

All he had to do is two more steps to stop the countdown. He would then get his freedom and the role reversal. But then again, she never said how long was the time she originally intended to keep him like that.

“Well, darling, time’s up. Remember, every 10 seconds late is one more hour of this.” she said, making a broad gesture to all the devious devices in the playroom.

He stayed there, thinking, weighing his options, looking at the devices, the tables, the posts, the crosses, the wheels, the cages, feeling his painful cock wanting to grow… and began to count. One Mississippi, two Mississippi…

© Pete / monsterp63, August 19, 2020.

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