Spin The Bottle

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Wendy froze when she felt Steve's fingers glide across her panties. She was rock hard and incredibly uncomfortable with her erect penis confined along her perineum, held there by her pantyhose. She knew that they were going too far but maybe they had already crossed the Rubicon because when Steve slipped his fingers between her legs she nearly fainted with the delight of it.

Steve felt the shape of Wendy's' cock pressed into her crotch and to his surprise he was not repulsed. He slipped his hand down the waistband of her pantyhose and freed it so that it lay along her lower belly and then extracted his hand and pulled her pantyhose and panties back over it. He could feel the shape of it through her panties and pantyhose and that was ok; he wasn't actually toughing the flesh.

He crushed his lips against hers, drove his tongue into her mouth and pulled her tight. He rubbed her hard cock through her panties and listened to her moan like slattern and writhe like a whore. Wendy gripped his cock tighter and stroked it and Steven gasped into her mouth and it was his turn for his knees to buckle.

He lifted Wendy up and sat her on the desk and she opened her legs so he could hold her close and she wrapped them around him and he pulled off his shirt so he could feel her legs on his flesh. He stroked her thighs and found her cock again and he stroked that too and he was so excited that it didn't matter who or what she was. She was his!

His hand slipped under Wendy's buttocks and he pulled her closer to him and eased her hand off his cock and pressed it against hers and rubbed it there. Driblets of precum soaked into her panties as Steven frotted her, their cocks rubbing together through layers of nylon and satin. Neither of them had ever felt anything so outrageously decadent, delightful and lecherous and they clung to each other and rutted, Wendy scissoring her legs along Steve's flanks to encourage him.

Steve's cock slipped inside Wendy's panties and now there was just a flimsy layer of pantyhose keeping their cocks from actually touching. The sensations were delightful, the slinky nylon igniting scintillas of pleasure as they kissed and dry-humped each other.

Steve pulled Wendy's ass closer or the edge of the table so he could press his dick harder against hers and he mistimed his thrust and slipped between her buttocks.

They both stopped. Wendy alarmed and Steven suddenly aware that his cock was close to Wendy's sphincter.

"No! Not that!" Wendy whispered.

Steven ignored her and pushed his cock into the crevice between her buttocks.

"No! Not that Steve. That's too much," Wendy nibbled his ear, hoping he would comply with her wishes.

But to Steve the nibble was encouragement.

He looked frantically around the enclosed space until he found what he was looking for.

He eyes zeroed in on the shelf that held the cleaning products. There was a squeeze bottle of moisturising hand cleaner on the shelf and it was perfect the purpose that Steve intended to use it for.

"Don't do that please?" Wendy sighed but she didn't unlock her legs from around his waist.

Steve gripped the waistband of Wendy's pantyhose and yanked the front of her panties nylons down until her cock sprang free and it stood stiff and proud. Steve pressed his cock against it and they both watched fascinated as Steve rubbed his cock on hers, their precum comingling and lubricating the shafts.

Steve was able to reach out and press down on the trigger of the cleaning emollient and took a generous gobbet and applied it to their conjoined cocks and stroked them with his hand and Wendy leaned up and kissed him passionately as rings of pleasure radiated from her cock. She could feel the blood pounding in Steve's phallus as they rubbed them together.

She was drowsy with the hypnotic bliss as their penises ground against each other and their lips crushed together, their tongues entwined when she felt Steve reach for another handful of the emollient. This time it dribbled into her ass crack and it tickled her and she smiled around the kiss.

The smile became a stifled scream as Steve pushed his cock into the cleft of her ass and pierced her sphincter.

"No! No! No! No!" she screamed and pounded her fists on his shoulders but Steve held her still.

"Shut up you silly bitch! They others will wonder what's happening," Steve hissed.

And wonder they did as they pounded on the door.

"What's going on in there are you ok Wendy?" Christine called.

"Tell them you're ok," Steve hissed.

"You bastard," she whispered; but Steve still had the head of cock inside her and he wasn't going anywhere.

"I'm ok. I slipped off the desk but it's alright now," Wendy scrambled for an excuse to explain her cries.

Steve took the opportunity to slide another inch of cock inside Wendy's tight cleft.

An amazing thing was happening. After the initial pain, the stinging went away and was replaced by a pleasant fullness that was quite bearable.

"What are you doing on the desk?" Christine sounded confused.

Steve looked at Wendy; an amused look on his face. He pushed another inch of cock into her and saw the look of surprised delight on her face.

Wendy was amazed at how wonderful it felt having Steve's cock inside her. She could feel all of her girly attributes: the satin panties clinging to her buttocks, the pantyhose swathing her legs, the high heels on her feet, the satin blouse on her tender flesh, she could taste and smell the makeup and perfume. She had never felt so feminine and so desired and she also felt wanton and lecherous. She wriggled her ass a little to get more comfortable.

"I'm perched on the edge of it so Steve can fuck me," she whispered and she and Steve supressed a muffled chuckle.

"I'm just sitting on it and Steve's kissing me is all. How long do we have left?" Wendy asked.

"Two minutes," Grant called through the door.

"Well fuck off and leave us alone then. There's kissing to be done!" Steve growled but he was staring at Wendy lovingly and pushed the remainder of his phallus into her.

Wendy had never felt anything so amazing. He sphincter was tingling with delectable little sparklets, her anus felt stretched and full, but comfortably so and Steve's cock was pressing on her prostate evoking a deep pleasurable throb.

"Two minutes," Wendy whispered and locked her legs around Steve's waist encouraging him to fuck her.

He leaned down and she raised her head so that they could kiss while Steve began to fuck her with long slow strokes that slowly began to build. He took her hard cock in his hand and stroked it in time with his trusts.

Wendy was writhing on the table in wanton lust, her anus burning with desire, her cock tingling with pleasure, her mouth filled with Steven's tongue.

Wendy's anus felt so tight around Steve's cock. He'd never fucked a girl in the ass and he'd fucked a few licentious older women but they were nothing like this. Wendy's anus felt like it was milking him with a velvet glove as he slammed his cock in out of her tight cleft. Her kisses were wild and wonderful and she kept sliding her nylon-sheathed legs across his sensitive skin and her high heels were raking his flanks like a cowgirl encouraging a bronco to gallop.

Wendy was just a girl. A slattern. A whore. William Mitchell was somewhere far away in another universe as Wendy enjoyed having Steve Townsend's jock-cock jackhammering in and out of her anus whilst she clung to him, kissing him so hard that their teeth were clacking. Steve was wanking her cock faster and faster and suddenly her whole conscience exploded with overwhelming pleasure as a huge orgasm began to build in her prostate and spread along the tight passage that was her anus down to the tingling ring of her sphincter and finally to her throbbing penis which erupted like a geyser, spraying her sperm everywhere.

Steve was amazed at the intensity of Wendy's orgasm as she writhed on the table, scratching his back, raking his flanks, spraying her issue all over him as her mouth sucked on his like a succubus. He rammed his cock deep inside her and ejaculated and Wendy bucked as she felt his scalding issue fill her bowel.

Steve felt an overwhelming wave of pleasure engulf him as his cock juddered and quivered as he filled Wendy's back passage with his hot load. He clung to her and she to him as they rutted like animals.

Neither of them heard Grant Butler hammering on the door yelling out that time was up.

They remained cleaved to each other, quivering and mewling until their orgasms subsided and then they had to live with the consequences of what they had just done.

Wendy lowered her legs and Steve pulled his cock out of her ass with an audible plop and watched amazed as a rivulet of cum dribbled from her sphincter and soaked into her panties and nylons. He snatched at the paper towel and gave her a handful so she could dry the glutinous mess before it soaked into her black velvet skirt but she didn't quite make it.

"Oops," she smiled up at him looking like a pretty whore with her lipstick smeared around her mouth, her blouse wide open, her skirt hiked up and her legs spread.

They cleaned up as best they could but Wendy's panties and pantyhose were cum-stained and her skirt had silvery trails of semen on the hem. Her makeup and hair was a mess but she had managed to put on her brassiere and button her blouse which was when she found semen stains on the purple satin. She shrugged her shoulders; there was nothing she could do about it.

The front of Steve's jeans was wet with his cum and some of Wendy's but try as might he couldn't get it dry. He pulled out his shirttails out to cover it hoping no one would notice.

What was noticeable was the stench of semen when they opened the closet door to the annoyed glare of Christine Baker and a bemused grinning Grant Butler.

"Don't tell me you two were just kissing in there! Look at the state of you both!" Christine tapped her foot angrily.

Grant smiled conspiratorially at Steve Townsend who at first stared at him blankly but then broke into a victorious grin.

"Ok. That's enough! The party is over but don't you guys go anywhere. Start cleaning up down here while I take Wendy upstairs and clean her up and give her back her real identity.

Wendy actually felt sad that she was going disappear and be replaced by William Mitchell but she knew that the fantasy had to end eventually. She followed Wendy up the two flights of stairs and was once again rewarded with the sight of Christine's pretty pink panties encasing her pert buttocks.

Wendy followed Christine into her bedroom and stood in the middle of the room feeling like a naughty little sister.

"I can't believe you did what I think you did! No! What I know you did!" Christine's chest was heaving with anger.

"You had semen on your legs when you came of the closet with Grant so I'm guessing you gave him a handjob or most likely a panty-pop but I'm pretty sure that Steve fucked you," Christine stood with her hands on her hips and Wendy thought she had never looked so beautiful.

"What's a panty-pop?" Wendy asked meekly.

"It's when you let a guy rub his cock on your vagina but you keep your panties on... Jesus Christ Wendy do you know what you've done?" Christine was livid.

"Why do you care Christine? Are you jealous that the boys went for me more than they did for you?" Wendy countered.

"Steven Townsend, the jock bully who loves himself and Grant Butler the dumb stoner who will do whatever everyone else does regardless of the consequences? Really? I have boyfriend who goes to college. He's a proper man; not some oversexed teenager!" Christine snapped back.

Wendy stepped into Christine.

"So you're no virgin?" Wendy whispered.

Christine just smiled conspiratorially.

"Well neither am I now," Wendy grinned.

"Well yeah, technically you popped your cherry I guess; but only in the ass," Christine said levelly.

Then they both realised the absurdity of the situation and they burst out laughing.

"I suppose I was a little jealous. If there was any boy in our group of friends that I'd let fuck me it would most likely be Steve Townsend," Christine admitted.

"What about Will Mitchell," Wendy pretended to pout.

"Nah. Word is he's a sissy who takes it up the ass," Christine giggled.

"You bitch!" Wendy laughed along with her.

"But Wendy Mitchell is hot and if I was ever going to have sex with a girl it would be with her. Besides she has a dick so it would be the best of both worlds. Lesbian sex but with a chick with a dick," Christine chuckled but suddenly the room went quiet.

They fell on the bed ruining the perfectly made-up pink stain comforter and scattering the fluffy toys and throw pillows. Their pantyhose-clad legs intertwined as their lips locked and their tongues explored each other's mouths. They could taste each other's lipstick.

"Hurry. We don't have long with those boys downstairs," Christine broke the kiss long enough to pull down her panties.

Wendy didn't even bother with that. She was rock hard in anticipation and she tore a hole in her pantyhose and poked her hard cock through it. Christine took the long meaty phallus in her fingers and stroked it to full tumescence while they kissed then she rolled on her back and opened her legs.

The feel of their pantyhose rubbing together as Wendy climbed on top of Christine was so overwhelming that Wendy nearly came but she held back long enough for Christine guide her cock to her nylon shrouded vagina. Wendy hooked a fingernail in the crotch of Christine pantyhose and ripped a cock-sized hole and Christine opened her legs wide and Wendy pushed her cock through the hole and into Christine's warm, moist, fleshy cunt.

Christine had been wet for a while. She had been aroused when she kissed Wendy in the kissing circle and whilst she listened to her having sex with Grant and Steve in the closet. She wrapped her legs around Wendy and lifted her crotch as Wendy ploughed her with her rampant cock. Wendy was awestruck with the feeling of Christine's tight, slick vagina around her throbbing phallus. They kissed and pawed at each other, their nylons swishing as they scissored their legs together to maximise their pleasure.

To Christine it was an amazing experience to have a girl lying on top of her, kissing and probing her tight pussy with her steely rod. She began to shake and shimmy as a huge orgasm welled up from between her legs as Wendy's pubis pressed on her clitoris and her cock pounded her tight pussy, hammering at her G-spot.

Wendy came along with her, driving her cock deep into Christine's tight, warm, moist cleft and depositing her seed.

The two girls clutched at each other, legs locked, mouths joined in frenetic kisses as they climaxed.

When they were done, Wendy lay between Christine's legs in post-coital bliss.

"Ok. Get off me you slut. Let's get you changed out of those clothes. You smell like a cum-bucket," Christine playfully slapped Wendy's ass.

Wendy was bitterly sad that the day had to end. She used Christine's moisturised makeup-wipes and scrubbed hard at the eyeliner and long-lasting lipstick which was particularly hard to remove. She showered and washed away the last vestiges of Wendy. She disappeared down the plug, a colourful rainbow of eyeshadow, rouge, foundation, powder and perfume.

Will Mitchell came out of the bathroom with a towel around his waist carrying the cam-spattered clothing he had worn when he was Wendy.

"Where do you want this? I figured you wouldn't want it in the laundry basket," William blushed.

"Just dump it on the floor. I'll put it in the trash except for the jewellery and the high heels of course," Christine said, sitting at the vanity fixing the makeup she had ruined when they fucked.

"Can I have it? A souvenir?" Will blushed; he was a blusher just like Wendy.

"You can have all of it, including the heels and junk jewellery and the Polaroids I took. There are plastic garbage bags under the sink," Christine put the finishing touches to her lipstick.

Will noticed that she had changed her pantyhose and saw the ones she had fucked in discarded on the floor. He added them to the pile of clothes and high heels in his arms and went into the ensuite bathroom and double-bagged his stash of clothing putting the pictures Christine had taken on top.

Will dressed in silence and he and Christine hardly spoke until they were back in the rec-room which was had been cleaned up in their absence by Steve and Grant. Grant had poured one last round of JD and Coke for them all.

Christine addressed the room, looking at them individually in the eye as she spoke.

"You realise that we can never tell anyone about what we did today," she said soberly.

"Never," the others spoke in chorus.

"Then one last drink," she held up her cup to make a toast.

"To total secrecy and goodbye to Wendy forever," she said.

They clicked plastic cups together and drank, Will blushing at the mention of Wendy.

They all wondered if they would keep what happened in the rec-room a secret and if Wendy was gone forever.

One Year Later

Wendy Mitchell was dressed in a red satin evening gown, slit to the waist it showed off her long legs encased in sheer taupe holdup stockings. She was wearing tight red spandex panties so that they didn't ruin the line of her dress and they also held her penis and scrotum tight along her perineum.

Her blonde hair was coiffed and her pencilled brows plucked and shaped and that was the only hair on her body. Her makeup was heavy put perfect and she knew that she looked beautiful. Over the last twelve months she had become an accomplished female impersonator.

Wendy's housemate had gone home for the two week break between semesters but William Mitchell had stayed in the little apartment they rented close to the college.

Wendy opened the door and welcomed her visitors. Christine Baker looked stunning in a little black cocktail dress, tan nylons and black pumps. Steven Townsend and Grant Butler were both dressed in letterman jackets and jeans.

Wendy closed the door and Steve and Grant put down the sacks they had been carrying. Grant took out a 1.75 litre bottle of Jack Daniel's and two six packs of Cokes while Christine took ice out of the fridge.

"I brought along a memento," Christine smiled as she held up the iconic contour-fluted Coca-Cola bottle they had used in the rec-room one year earlier.

"Don't think we'll be needing it," Steve said as he swept Wendy into his arms and kissed her passionately.

"Guess not," Grant agreed as he reached for Christine.

The End

Author's Note: I would deeply appreciate a comment or two as a scant reward for my efforts. An intellectual once wrote: "Writing should almost always be a communication between writer and reader, and therefore feedback is the best way to sample how that communication is developing"

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55 Comments
Shawna_RichardsonShawna_Richardsonabout 2 months ago

Great story, pantyhose are amazing as is the crossdressing. I love this story and wish it would have been me.

Stacy_LovingStacy_Lovingabout 2 months ago

A wonderful story. I loved how the sexual tension built over the course of the evening and the sexual activity progressed accordingly .Very erotic. It also reminds me greatly of some of my early adventures in dressing and experimenting with my friends. Thanks for the delightful read.

AnonymousAnonymous3 months ago

I loved the kissing! I love dressing and being the submissive, I loved this story and would so love to be Wendy!

KinkyEnglishBoyKinkyEnglishBoy4 months ago

Loved it! HAving the guys actually desire Wendy from the start really made the story. Humiliation of TV/TG girls is a very common theme, which is cool, but the story was much better the way you wrote it xx

ClessaWintersClessaWinters4 months ago

(Okay well also your bio say that you are transgender 😅 I forgot to peek over at that)

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