The Perils of Pauline - Tranny at the Truck Stop

by

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Ma, Mult, NonConsensual, Reluctant, Rape, Coercion, Blackmail, TransGender, CrossDressing, Fan Fiction, Rough, Humiliation, Gang Bang, White Male, White Female, Oral Sex, Anal Sex, Masturbation, Exhibitionism, Voyeurism, Double Penetration, BBW, Leg Fetish, Public Sex, Transformation, .

Desc: Erotica Sex Story: Paul is a closet tranny who meets regularly with other transvestites for platonic get-togethers. He usually stops to change in a seldom-used rest room at a remote truck stop so that she can arrive at the get-together already transformed into Pauline. Tonight however, the restroom is a convenient place for some bikers to take a leak before they go over to the truck stop bar to drink beer. What will the bikers do when they find a foxy tranny hiding in one of the stalls?

Paul sat behind the wheel of his Mustang, the windscreen opaque with heavy rain. It had been raining hard for the last hour and he was hoping it would have stopped before he reached the truck stop. He looked through the windshield as the wipers lazily swept back and forth across the glass. The sodium vapour lamps bathed the parking lot in an orange hue. The blacktop was slick with rain and puddles had formed in the numerous potholes.

The lot was quiet; as it usually was at 8:30pm on a Tuesday night. A dozen big rigs were parked haphazardly here and there; an old Winnebago and half a dozen pickups made up the rest of the parking lot entourage. The Winnebago and the pickups were parked right outside Bob's Old Style Diner And Bar: "Cold Beer, Hot Food And Live Band Most Nights", the fading placard read. Underneath written in large italics was: "We're Famous For Our Ribs!"

"Famous for our fucking heartburn!" Paul sighed.

Paul Morecock was an executive on the board a company that represented local primary producers. He was well paid and mingled socially and professionally with most of the upper and middle class professionals in the area. He was also a closet transvestite. Now these two vocations do not sit well together for obvious reasons. Paul liked to dress up in ladies clothes and entertain himself in ways that the other members of the board may well frown upon and for this reason he is what is known in 'the game' as a 'closet transvestite.'

He had been dressing in women's clothes on and off since his early teens. Like most crossdressers he had started off wearing panties, hosiery and whatever lingerie he could lay his hands on and over the years his fetish had developed and matured. He now had a fully shaved body under his business suit and, give him three-quarters of an hour, he could transform from staid businessman Paul, to transvestite vixen Pauline.

He was thirty years old and over the years he had mastered the art of makeup, the finesse of picking out clothes that suited his slim build and that made him look both feminine and sexy, the knack of acquiring wigs that suited his facial features and maturity, and the dexterity to present himself as womanly as possible. The only problem was that his secret was so secret that he had only ever crossdressed at home. At first it was exhilarating and when the Internet came along with its various transgender friendly websites, chatrooms, and see-to-see webcam sites it had become even more exciting. But after a while this too had become mundane and boring.

Then Paul found a website for a crossdressing support group that was located only an hour away in the neighbouring suburb of Kneeling. It offered complete discretion and the reassurance that others with the same compulsion to crossdress could get together in a relaxed and safe environment and spend time together and share their experiences and help each other in secrecy. It was like AA for crossdressers!

When Paul had decided to attend the group he soon realised that he had to figure out a way to arrive and leave dressed as Pauline; there was no way he was going to let anyone know that Paul Morecock was a crossdresser. He had contacted the group online and he was welcomed and told how discrete they all were and that he could go there dressed as a man and transform in the comfort and privacy of whoever's home was hosting the meeting. About half a dozen of the group lived alone and had suitable accommodation such that they could host the meetings and keep them discrete. The group met each Tuesday evening at the home of whoever was rostered to host.

He had mused and plotted for a number of weeks; he so wanted to meet with other like-minded individuals who shared his penchant for dressing like a sexy coquette but there was no way he was prepared to disclose his identity. Then he'd found the truck stop during his travels.

Located on the interstate only ten minutes away from Kneeling; it was reasonably quiet on Tuesday nights and had exactly what he needed. A large restroom was located next to the blacktop parking area; far enough away from the Diner so that no one could see the patrons entering or leaving the restrooms. It was quiet, secluded and seldom used as most of the travellers were lured to Bob's Diner and took care of their bathroom business there. It was also clean and well maintained even though it was little used. And; he could park right beside it!

Except for tonight! Some asshole had parked a Peter-built prime mover and trailer right next to the rest room.

"Fuck!" Paul exclaimed; his frustration evident.

He looked at the drizzle, the puddles in the carpark and the big rig taking up his usual parking space and considered calling it quits and heading back home.

Usually he parked right next to the restroom and nipped inside with his carry bag full of girly accoutrements, transformed into Pauline in the privacy of one of the stalls and then quickly exited to his car and completed his journey. He did the reverse on the way home, transforming from Pauline to Paul in the seldom-used facility. As it was open twenty-four hours, kept clean and well lit but seldom used, it was perfect and allowed him to keep his identity secret from the other crossdressers.

Some of the other transvestites dressed at home before going to the meetings so he was not the only one who arrived and departed in female personas. He had found the meetings very exciting at first; all these crossdressers sitting around discussing crossdressing tips and telling tales. Some of the 'girls' sometimes allowed their stories to become a little risque but the office-holders of the group quickly shut such talk down. Any talk of sex was quickly quashed; the group was strictly platonic and any attempt to organise sexual encounters resulted in immediate excommunication.

Paul had to admit that he did get immense sexual satisfaction when he was dressed as Pauline; he almost always masturbated while crossdressed and found himself physically attracted to number of the members of the group. He really wanted to go to the meeting again tonight; he was sure that some of 'girls' held clandestine trysts and he wanted to find out how he could be included.

He had never had sex with another person whilst dressed as Pauline but he fantasised about it constantly. In his fantasies he was always with another attractive mature transvestite, exploring each other's secrets whilst clad in sexy skirts, silky satin panties and sleek nylons.

"Fuck it!"

Paul reached over into the back seat and grabbed his carry bag and opened the car door and made a run for the restroom, pressing the button on the remote locking device as he sprinted across the car park. He entered the restroom and a quick inspection revealed that it was empty as usual. He quickly went to the disabled person's cubicle and locked the door behind him. The disabled cubicle was twice as large as the other stalls and had plenty of room for him to lay out his clothes and also had its own sink and mirror. It also had a proper full-length door as opposed to the other stalls that had a large gap between the bottom of the door and the floor. It was the perfect place to transform.

Paul opened his bag and hung his female clothing on the hook on the back of the door, laid his lingerie on the toilet lid and unzipped his cosmetics bag and arranged his makeup on the ledge above the sink. He opened a small velvet jewellery bag and extricated the contents, laying them out besides the cosmetics. He took a pair of four-inch patent leather black stiletto high-heels out of the bag and placed them on the floor.

Paul stripped naked and carefully folded his male clothes and put then in the carry bag. In his mind he became Pauline.

Pauline stood in front of the mirror and carefully applied foundation and then a coating of finishing powder. Next she applied her eyeliner liberally to her upper and lower eyelids, from the inner corner of her eyes to the outer corners, gradually thickening the line as she went. She selected dark blue eyeshadow, which she applied to her eyelids and then blended with a shade of mauve which she brushed onto the upper part of her eye sockets and right up to her eyebrows. She rouged her cheeks to define her cheekbones and applied another light dusting of face powder. She carefully brushed a heavy coating of mascara onto her lower and upper eyelashes.

Pauline took her time putting on her lipstick; Covergirl two coat. The base coat was a deep plum red; once it had set she applied the clear topcoat. She painstakingly painted her fingernails with matching nailpolish while the lipstick set. The whole procedure had taken about thirty minutes.

Pauline shook the brunette, shoulder-length wig out of the net bag in which she had transported it and brushed it out She positioned the wig on her head and adjusted it so that her fringe was straight and hung level with her eyebrows.

She looked in the mirror and was happy with what she saw.

"MMmm, now the fun part," she giggled.

Pauline stepped into a pair of white satin full-brief panties, they had a lace trim and she savoured the feel of the cool delicate fabric on her skin. She adjusted the waistband on her hips so that the cute little lace bow was centrally located below her belly button. Next she stepped into a black satin garter belt sitting it snugly around her waist and carefully threaded the suspender straps under the waistband of her panties and out of the legholes.

Now her favourite part of dressing; she slid a pair of fully-fashioned, fifteen denier, high-sheen, taupe stockings onto each leg, carefully straightening the seams before clipping the dark welts to the silver garter clips.

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