The Girl In The Blue Denim Skirt

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"You don't have to do that Dennis," she said, aware that it was Dennis's first time with a transvestite and what she had down there might repel him.

Dennis looked down at Charmaine's fetching countenance framed by that fiery red hair: her blue eyes enhanced by black eyeliner and mascara, her cheekbones rouged, those soft sensuous lips, her lipstick smudged a little because of their kisses and he breathed in her scent. The feel of her beneath him and those long legs swathed in the soft pantyhose was heaven. This was just how he dreamed it would be.

"I know what you are and what you do and it doesn't disgust me Charmaine. It fuels my desire and I want to experience every part of you and your body," Dennis's whispered and lowered his face to hers so the he could kiss her.

Charmaine was delighted and wrapped her legs around Dennis and squeezed his throbbing cock. Dennis stroked the front of Charmaine's knickers, the sleek satin sliding over the gusset of her pantyhose. She did something like a kegel and suddenly the smooth V of her knickers was filled with what felt like a small snake, coiled and waiting to strike.

Dennis took the appendage in his fingers and stroked the smooth flesh over the layers of satin and nylon and felt it awaken. It was both fascinating and exhilarating. The two lovers kissed while they caressed each other's genitals in the dim light of lamp.

Dennis wriggled out of his trousers but left the rest of his clothes on because the air was chilly. Charmaine was warmed by Dennis's body lying on top of her. Dennis wriggled again and Charmaine sensed his need and guided his cock to her crotch so that Dennis could rub his cock against hers through the layers of silky fabric.

Dennis was in heaven. The feel of Charmaine's hard cock trapped inside her tights and knickers against his own throbbing manhood was delightfully decadent and sensuous. He pushed his cock into the valley between her legs and felt those soft cheap pantyhose on his bloated manhood. The feeling was overwhelming.

Charmaine felt the warm wetness between her legs as Dennis's cock quivered and soaked her thighs with his issue.

"I'm sorry," Dennis apologised, absolutely despondent that he had come so quickly.

"That's ok. You're a virile man I'm sure you have more than one shot in you," Charmaine nibbled his earlobe and wrapped her legs around him.

Her own cock was throbbing and she too was close to extremis, feeling Dennis's cock pulse and quiver between her legs as the last of his issue soaked into her tights and knickers.

They continued to kiss and hold each other tight and Dennis's cock returned to full turgidity and Charmaine smiled.

"I told you,' she smiled up at him cheekily.

"I want to fuck you," Dennis looked down at her, filled with wanton desire.

Charmaine put a finger inside the gusset of her knickers and pressed it against the seam of her pantyhose and pushed it through the fabric making a cock-sized hole. She eased aside the gusset of her knickers and guided Dennis's cock to the hole.

"Are you sure? I don't want you doing anything that you might regret," she looked up at him with genuine affection.

Dennis kissed her and pushed his cock through the hole and nestled it in her puckered bud. She held him tight as he slid his turgid manhood past her sphincter into her snug anus. She scissored her calves against his flanks and Dennis relished the sensation of her velvety tights on his tender flesh.

Charmaine snuggled under him so that her buttocks were positioned perfectly so that Dennis could thrust his steely phallus in and out of her tight receptacle which he slowly began to do, clinging to her, kissing her passionately and delighting in the feel of her tight channel clinging to his throbbing cock. Being a working girl Charmaine had pre-lubricated herself and Dennis’s pre-ejaculatory secretions coalesced with the Vaseline inside her rectum and eased the way for his monster cock so that he could drive it all the way inside her tight channel.

Charmaine gasped with pleasure as the glans of Dennis's penis pressed on her prostate and her cock began to quiver inside her knickers. Dennis could feel it pressing into his belly and to his surprise; far from being disgusted he was delighted. He could feel the dampness of her pre-seminal fluid saturating the front of her knickers, warm and wet on his belly.

In a scene from the movie Tranny Streetwalkers one of ‘girls’ was leaning against the wall with her knickers and tights bunched around her knees whilst a punter rogered her from behind. He was sure that the actress was not just pretending to like what the man was doing to her and he was fascinated when the girl suddenly began to shake and moan and then with her penis still flaccid she spent herself, her issue dribbling from her soft cock into her knickers as the man fucking her from behind invoked her orgasm.

Dennis wanted Charmaine to do likewise, to climax without manual stimulation to her penis and he was rewarded accordingly when Charmaine buried her head in his shoulder and gasped, locking her legs around him and holding him close and she began to shake and quiver as she filled her knickers with hot steamy cream.

She was sobbing and moaning as her orgasm washed ever her and she triggered a likewise response in Dennis who thrust his hard phallus deep inside her and ejaculated.

He found her mouth with his and kissed her; the two lovers holding onto each other, quivering with lecherous desire as they climaxed. Dennis began to thrust again and Charmaine met him, rising her buttocks up off the bed to meet him and soon they established a steady rhythm and to the amazement of them both they climaxed again, this time Charmaine whimpered and held Dennis close, locking her legs and arms around him as he voided inside her for the second time.

They lay locked together like that for seemed like an eternity until the cold and the cramped conditions forced them apart.

Dennis helped Charmaine up off the bed, her skirt still rucked around her waist which was just as well as the front of knickers and tights were saturated with her spend and the seat of her knickers was also becoming damp as Dennis's issue dribbled from her anus.

She took off her heels and rolled down her tights and her knickers and wiped herself dry with them and took another pair of kickers and tights from her purse and sat on the cot to put them on. Dennis dressed himself and looked away while she did so, partly because he thought she deserved privacy but also because now that the coital bliss had dissipated he didn’t want to see Charmaine’s flaccid penis.

She gave him a cigarette and they smoked in silence sitting side by side on the cot.

“Any regrets?” Charmaine finally broke the silence.

“None. It was wonderful; everything I’d imagined it would be,” Dennis brushed a lock of hair out of her eyes and kissed her tenderly.

Charmaine crushed out her cigarette and took a compact form her purse and fixed her makeup and applied lipstick.

“It’s amazing what you can keep in the purse,” Dennis broke the awkward silence.

“I call it my Tardis,” she smiled up at him.

He helped her to her feet and held her jacket so she could put it on and then they walked hand in hand back to her place on the wall.

“See you again?” Charmaine stepped into him and softly kissed the side of his mouth.

“Tomorrow night,” Dennis whispered and then he slowly walked away.

*****

“So you did finally fuck her after all that back and forth over the last few weeks,” Steven smiled lecherously.

“Yes I did and it was fucking marvellous,” Dennis replied smugly

Dennis had given a full rendition of his encounter with Charmaine. The only part that he had left out and would never admit to was that Charmaine was a transvestite. Best that Steven just think Charmaine was a common brass like the other women who plied their trade along the wall just inside Aston Park.

By now Dennis was dressed and ready to leave for his shift at the Holte public house, Steven still had his towel wrapped around his waist but he pulled his holdall from his locker so could begin to get dressed.

“And she threw you a free one? Are you going to see her again?” Steven asked placing his holdall on the slatted bench.

“I think I might just see her tonight after my shift at the Holte,” Dennis grinned.

“I bet you she won’t throw you a freebie this time,” Steven chuckled.

“I don’t know; she seems pretty sweet on me,” Dennis's grin widened.

“Away with ya! Fuck off and go to work,” Steven waved a hand at Dennis dismissively.

When Dennis left the change room Steven locked the door behind him and checked his freshly shaven face in the mirror then he opened his holdall. He would dress in the privacy of the now deserted change room and then go work his second job

He arranged his clothes on the wooden slatted bench beside his makeup bag: a pair of white high heels, a freshly laundered mauve satin blouse, a red satin brassiere and matching full-cut knickers and a six-pack of cheap Tesco tights from which two pairs had already been used. He brushed out the fiery-red long-haired wig and lay it down beside the faded and frayed blue denim skirt.

The end

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
AnonymousAnonymousabout 1 month ago

Surprise !!,

LingeringViceLingeringVice12 months ago

The build up and the sex was great, that ending was a cherry on top. I'd be curious about how his wife could entertain or be his fantasy if there was a sequel.

Rapierwit24601Rapierwit2460112 months ago

Fuckin’ brilliant, mate!

AnonymousAnonymous12 months ago

Wow! I loved the ending. Steven must really love Dennis. I do wonder how Dennis will react when he finds out.

CaSlutCaSlut12 months ago

Oh, nice and unexpected ending.

Show More
Share this Story

Similar Stories

Teacher Surprise College student bumps into his high school teacher at a club.in Transgender & Crossdressers
Our New Babysitter Ch. 02 My wife is sober this time with the babysitter.in Transgender & Crossdressers
Spin The Bottle Need another girl to play spin the bottle so they make one.in Transgender & Crossdressers
My Catwoman Straight guy hooks up with trans girl after a costume party.in Transgender & Crossdressers
The Quickie Horny transgirl takes a coffee shop worker into a restroom.in Transgender & Crossdressers
More Stories