Rest Area Stories

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Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

Time for a Break

by margobicd on Sep 16, 2017
Transsexuals & Crossdressers

So, I'm driving down the highway dressed in a cute little flowered summer dress. Kind of flimsy and kind of short but it's so comfortable and it feels so good on. I've been on the road for 4 or 5 hours and I'm feeling a little tired and am looking for a rest area or parking area to take a little break. Finally I spot a parking area coming up in a few miles...

Rest Area

by cockbelowtheknee on Sep 2, 2017
Exhibitionist & Voyeur

What was I thinking? Oh well it was a nice day for a drive. She probably wouldn't even show up. Sure we had been talking online for a while, and the idea of meeting ½ way for sex in the rest area was fun to think about but who was I kidding? We both agreed it was a neat fantasy but now the time was actually here. I pulled the truck off the interstate and tur...

Hogwarts: The House Wars

by Leto on Apr 29, 2025

Starting in the year 1995 This was the Trio's 5th year being at Hogwarts, They knew many things by now but they are soon to find out. This is a story about winners take all and losers getting fucked. How it works? It starts at the beginning of the year and goes till the end. Which ever house has the most points is the winner for that year. The second place h...

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Sissy's Decline into a Slut Pt. 02

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...

Rest Area Cigarette

by Alluring_Crimson_Shifter on Sep 16, 2017
Exhibitionist & Voyeur

They were driving all night to get home from a vacation road trip to the beach. Marie said over the drone of the engine, "Why don't you stop so I can get some cigarettes?" Bill was driving and replied in a controlling tone, "I told you, cigarettes are bad for you. Plus they are too expensive." She knew it was a useless battle so she quit before it turned...

Passerby Gets Lucky at Rest Area

by liljohnson46 on Aug 31, 2017
Exhibitionist & Voyeur

One night my wife was giving me a blowjob while we sat in our car in the parking lot of a rest area. She had removed her top and bra exposing her lovely 38DD tits. My jeans were down around my ankles and my stiff cock was warmly enveloped in her sucking mouth. I was rock hard and she had been slowly sucking on me for about ten minutes. A car pulled into th...

Parking Area 2 Miles

by Lovinhose on Sep 15, 2017
Transsexuals & Crossdressers

Prior to writing this next installment in my awesome sex life as a bisexual crossdresser, I thought I had already written about all of my worth while, true life experiences, but I had actually forgotten about this one. It happened in, I believe, 2008, during the end of the summer. I was driving my truck. I am a truck driver by trade. Three hours and a co...

Sailor Moon Ch. 02

by embarrassednakedmale on Feb 3, 2020
Transgender & Crossdressers

The alarm had been buzzing for a solid two minutes when a bleary-eyed Scott finally rolled over and slammed his hand down on the offending device. The harsh noise ceased immediately, and Scott groaned as he rolled back again and cautiously stared at the ceiling. It was still dark in his bedroom, although a single beam of light cut through a tiny gap in his...

The Rest Area Adventure

by stevew337 on Sep 16, 2017
Transsexuals & Crossdressers

I was going to be out of town all week and it would be a great time to dress up and look for adventure. I am twenty eight and have been dressing since I was in high school. I started with my sister's panties and bras and now have a closet full of clothes and underwear. My hair is down to my shoulders and when I am in makeup I look pretty sexy. I stopped wor...