Within minutes he was done and climbed to his feet. Holding the vibrator in his ass with one hand, he twisted then turned, rinsing the shave creamand hair off of himself. Looking down at his newly hairless state, he grimaced then opened the curtain.

Her, sitting almost naked, was the first thing Jimmy saw. Then, the smell of her excitement hit him. His prick twitched and his eyes dropped to the crotch of her panties. They'd become see-through and he gaped at her tantalizingly spread pussy, the fingers of one hand still gently rubbed her clit.

He stood dripping, unable to do much more than breath.

"Please Heather, let me" his voice trailed off as she pulled the crotch aside baring her sweet pussy.

"Dry off, Jimmy. God, you look sexy all naked like that. I brought you the outfit I want you to wear for the rest of the day. Even found you some sexy slippers to go with it," she purred.

Without another word, he reached for a large white bath towel and began to rub it over his freshly shaven skin. His prick danced as he dried himself, and from time to time he pressed the vibrator back into his ass, keeping it in place.

Finished, he dropped the towel into the hamper, then ran his fingers over his stomach and the newly shaven skin.

"Don't touch. Don't you dare touch my cock," she snapped when he neared the base of his shaft.

He jerked his hand away as if burned, then looked beseechingly at her.

"Put on your outfit Jimmy, I want to see how you look in it."

Glancing down, he saw the tiny pile of lingerie and blushed, but said nothing. Picking up the camisole, he slipped it over his head, shivering as it slid down his arms and back. It fit snugly around his ribs and chest, accentuating his slender, almost girlish build.

The crotchless panties were then tugged up his legs, framing the shaven swell of his scrotum and shaft.

He moaned when the back of the panties slid between the cheeks of his bottom, pushing the vibrator deep inside again. A quick glance at her, then one by one, he smoothed the stockings up his long, shapely legs.

She watched his fingers tremble, and realized how much he was enjoying what was happening. When he was satisfied that he'd done the best that he could, he tucked his feet into the slippers she'd supplied and stood facing her.

"Very pretty, Jimmy. No, not Jimmy, that won't do. What will I call you?"

She rose to her feet and walked around him. Touching him here and there, she slid her fingers over his sleek bottom.

"I know Jamie, that'll work, or Joan. Which do you prefer baby? After all, it's going to be your name for a while, I suppose you should have some say in it," she teased.

She held the lace ribbon in her hand and rubbed it over his straining shaft.

"Jamie, that's the way I think of myself." He whispered almost inaudibly.

Taking his hand in hers, Heather pressed the ribbon into it, and replied,

"Yes Jamie, I like that. Now then pretty Jamie, wrap my cock like you had it when I came in. Use the ribbon and show me how you tie it".

"Reluctance gone, he took the ribbon and shook it loose.

She watched wide-eyed, as he wrapped the ribbon around the base of his shaft and behind his testicles. Pulled tight enough to look painful, then he carefully separating each round globe, he bound them in white lace.

When he'd finished, there was still about eighteen inches of lace left dangling on each side. He looked sheepishly at her, not sure what he should do. "Come here, come on get closer." She scolded.

Taking a strand in each hand, she wound them up his shaft. Crisscrossed and nicely patterned, she soon had it all the way to the crown. With a quick flip and tuck, a bow appeared tied tightly behind the head. Rising to her feet, Heather gave him a very quick caress then let him loose, just as he began to thrust his hips.

"Time for your make-up and hair. Sit down and be quiet." She instructed and he quickly obeyed.

Gingerly, he sat on the chair facing the vanity mirror and watched as she pulled his hair back, then skillfully applied make up. Light foundation, followed by blush eyeliner, shadow and lastly, a pale peach lip-gloss.

He marveled at the transformation, blushing when he saw her grinning at him.

"I really should pluck your eyebrows, but I think that'll have to wait. They're pretty shaggy for a girl though, so I expect it done by tomorrow night. No argument, just make sure it's done."

She primped and fussed over him, then dug out a pair of scissors, a comb and her blow dryer. While he sat quietly, she styled his hair. Taking a bit off here and there, then blowing it dry, he watched as his very feminine counterpart emerged.

"Okay Jamie, you're done. Not bad for a tall skinny slut. Now, I'm dying for a drink and I think you should learn your new position in life. From now on you're the maid, the dishwasher, housekeeper, servant and whatever else I decide you are".

"For now just make me a drink and wait for me in the living room, on your knees, in front of my chair. Whatever you do, don't touch your cock. Remember, that's mine now. Stand up and turn around for a second."

She waited while he quickly stood up and spun around. Her hand on his shoulder pressed him forward. With practiced ease, she tugged the strip of cloth between his cheeks aside and switched the vibrator to a higher speed.

His bottom clenched and he groaned, as his prostate was stimulated, almost to the point of climax. A sharp slap to each cheek refocused his attention and he managed to hang on, but for howlong, he wasn't sure.

"Okay, time to get busy. Off you go now and get my drink."

Heather gave his testicles a last gentle tug, before letting his panties slip back into place. Minutes later she entered the living room, just in time to see him release his erection. He hadn't seen or heard her, so wasn't aware of the trouble he'd just got himself into.

Heather quietly crossed the room and stood behind him.

"I thought you weren't supposed to touch. You know you'll have to be punished now, don't you?"

Although her voice had been soft, Jamie whirled around in surprise.

"Heather," he cried, the drink tipping perilously close to being spilled.

"Yes, I'm here and I saw you. Got an excuse you'd like to share, or should I just proceed with your punishment?"

His mouth dropped and he knelt speechless, while she took the drink from his hand. Setting it on the table beside her chair, she looked down at her kneeling man.

He's beautiful she thought, loving the sight of him so turned on. His erection was gently throbbing and leaked a clear long ribbon of pre cum, almost to the floor.

"Spread your legs. Show me how turned on my little slutis."

He swiftly spread his knees, allowing his cock to hang between his thighs. The ribbon squeezed him mercilessly and he ached to stroke himself, if only for a minute more. Whatever kind of punishment she had in mind, would only add to his torture he was sure.

"I want you to put your hands behind your back Jamie. Perfect, now hold still, don't move a muscle or it'll hurt," she said.

At first he was confused, but as she unfastened the bow from the tip of his cock then pulled it back, he gasped fully understanding what she had in mind.

The ribbon was long enough, but only just, to tie to his joined thumbs. His glans were pulled downward and rubbed against the carpet whenever he moved. No matter how he struggled, he couldn't get free.

"Oh yes, I like this," she said,as she sat in her chair facing him.

She was flushed as well, from the newfound excitement of dominating him. Leaning back, she spread her legs, offering him the sight of her swollen pink labia.

"Wouldn't you like to kiss my pussy, Jamie?

I'm really wet and would love to feel your mouth on me. Unfortunately, you've been very bad, so I don't think you'll get to taste me just yet. But, just because you can't behave, there's no reason why I should suffer."

She placed her feet together and lifted her bottom, then squirming, slipped her panties off.

"Lean forward Jamie, I want you to watch me really close" her voice had dropped to little more than a husky whisper.

He lowered his eyes and seemed hypnotized as he slowly bent forward. His jaw dropped when he realized that he was pushing his weeping glans across the carpet.

Sweat beaded on his upper lip and the closer he got, the more her scent captivated him. When he was mere inches away, she spread her lips and he watched, spellbound, as the dewy nectar slithered towards her anus.

"Heather please" his voice trailed off when she produced her own long plastic vibrator.

"Lick it, get it wet for me," she snapped, and held it while he lathed it with his tongue.

She pressed it against his lips and he opened, then, sucked wetly on the heavily veined toy. Satisfied, she pulled it free then reversing it, held the base against his mouth.

"Hold it in your teeth and fuck me. Don't drop it and you better make me come or you'll be in even more trouble."

Wide eyed, Jimmy took the offered base between his teeth and held it tight.

Lying back, she pulled her legs even wider apart and draped each over an arm of her chair. Tentatively, carefully, he leaned forward brushing her lips with the tip of the toy.

She sighed as he began his task. By nodding his head, he spread her wide, then, with surprising ease, he pushed the vibrator into her sopping wet sex.

Heather was almost beside herself with pleasure; the sight of Jimmy striving so hard was driving her wild. She arched her body and was soon on her way to an earth-shattering climax. The closer she got, the further inside he pressed her toy, until his nose finally connected with her clit.

Smothering, almost desperate for his own release, Jimmy sawed the vibe in and out. The sloppy, sucking sound that came from her, made it harder for him to hold off his own release.

He twisted and turned the vibe as best as he could. Anything he could think of to bring her pleasure, to stop from rubbing on the carpet.

He watched as her body gave the tell tale signs of her impending climax and intensified his movements, as much as he could.

He rubbed his nose hard against her clit at each inward thrust of the vibe. Her inner thighs tensed, then she grabbed his head and pulled him hard against her, mashing his nose against her clit.

Trapped,unable to breathe, in a last all out effort he shook his head back and forth. Her climax hit then, shaking her body and her guttural cry filled the room.

Grinding her pussy against his face, he could do nothing but watch her spasm again and again. He held still as long as he could, but his body was crying out for air.

Finally, he began to struggle and she loosened her grip, just enough to let him back off and take a much needed breath.

Wanting to prolong her orgasm, he moved the vibe slowly in and out. She collapsed before him totally spent, allowing him the freedom to do so. When she'd had enough, she pushed him away, ignoring him for a few moments.

Sitting back on his heels, he breathed deeply around the base of the vibrator still clenched in his teeth. Aching to relieve the pressure in balls, his hips quivered as he tried to wait patiently for whatever Heather decided to do. He looked down at his erection, the purple head leaking acontinual ribbon of pre cum.

"Messy girl." He jumped at her voice, and then blushed as she looked down at his lace bound prick.

Reaching forward, she took the vibrator out of his mouth and let him take several deep breaths before continuing.

"Seems you have a problem there, Jamie. You've been very naughty and touched my cock when you were told not to. So, I've decided on your punishment. I'll allow you to come, but you have to do it without touching."

She seemed very pleased with herself. He knelt staring at her, uncomprehending.

"W-what how Heather, how can I do that?"

His hopes of coming seemed to be dashed.

"You can get to your feet and come here, to start with. I'll unwrap you, well some parts of you, but I think your thumbs had better be kept tied."

Struggling to his feet, he stepped closer to her then, watched eagerly as she unwound the lace from around his genitals. Down the shaft, then she released his swollen testicles.

Heather looked up at him then with a smile, left the lace tied tightly around the base.

"I think you should be able to manage now Jamie. I'll give you a little help. Spread your legs."

Without a word Jimmy complied, desperate for anything, just as long as he could come. Heather slipped her hand between his legs and began to toy with the vibrator still buried deep inside his ass.

He groaned as she twisted the base, increasing the speed of the vibration once more. His erection twitched and she slid the slender vibe in and out of him, while he tried desperately to keep still.

"Tell me how you feel right now, Jamie. I want to know everything about what turns you on when you're dressed like a woman, but for right now I want to hear you beg for it."

"Right now, I feel like my knees are going to let go. I'm so close to coming, Heather I can't ever remember feeling like this and you're driving me crazy. Please, I need to come so bad."

His entire body was trembling, but she refused to speed up her gentle thrusting.

"I know you're turned on, but I want to hear you beg. Tell me, what do you want."

Each time she thrust in, the tip of the vibe touched his prostate. He thought he would go mad, he could barely breathe, let alone make sense of what she was asking him to do. She slowed then stopped, and he began to whimper. He was so close.

"Heather God, fuck me! I need oh God I need to come. I'll tell you anything, anything you want, just fuck me now."

His hips moved against her hand and she allowed it for only a moment, before she grasped his testicles with her free hand. The shaft of his cock throbbed against her forearm, as she squeezed.

"Hold still then. Don't move or I'll stop and you won't get to come at all. So you want to get fucked do you? You're sure dressed for it".

The vibrator began its slow tormenting movement, sawing in and out of his ass. He tensed himself, feeling the blissful churning in his balls.

"All right, Jamie.I want you to come now. Then we're going to see about some changes around here."

Heather gripped the shaft of his cock and rubbed her thumb just behind the head. Groaning loudly, he gritted his teeth and soared towards sweet release.

His knees almost gave out as the first stream shot from the tip and landed on Heather's breast. He shuddered and then shot another stream of thick cream, his cock wildly jerking in her hand. Twice more he erupted spewing his come across her chest each time.

She continued to stoke him until his prick began to lose its stiffness, then, let him sag to his knees. She switched off the vibrator, as he lost his feet and smiled at the dazed look on his face.

"What a kinky slut you are Jamie. Now you've made a mess that you'll have to clean up. Look at all this come on me."

She thrust her breast towards his face. Gazing at her breasts, he leaned forward and began to lick them clean. She stroked his hair as he slid his wet tongue over her lapping up the thick strands of come.

"Good boy, you're such a good slut. I think we've discovered something we're both going to enjoy." She couldn't see the smile on his face.

Report Story

byhardnose© 7 comments/ 101572 views/ 28 favorites

Share the love

Tags For This Story

Report a Bug

2 Pages:12

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartpurekink, Whowalks and 26 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous03/03/18

How do you know?

I absolutely love this story but how did you know what my favorite jack off activities are? For years I have secretly dressed myself, completely shaved and totally hairless, in crotchless panties, thighmore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 7 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: