Trans On Sissy Stories

357,668 results
Orientation
Length
Source
Infinite Scroll

House Party

by Brav0tm on Sep 16, 2017
Group Sex

You come out of the room and you look fabulous you are wearing a short black skirt with thigh high stockings and a white blouse that has a silky touch to it and you are wearing some kickass boots. Your hair is done up in pig tails and as I look at you I can feel my cock stirring to life in my pants! You ask me how you look and all I can say is stunning!! I c...

Nude and Erect

by aaronburr on Dec 8, 2017
Exhibitionist & Voyeur

At Grover Cleveland High the swimming classes were held in the vast echoey basement pool, smelling of chlorine. There were bleachers rising on both sides to be packed out in the event of a competition. There were Corinthian columns and painted windows in the upper walls. The atmosphere was gloomy and... Well, full of possibility. For one reason. Classes...

Blue Bloods Meet Castle Pt. 19

by baranbrat on Sep 11, 2018
Celebrities & Fan Fiction

One of my readers requested adding pictures of the new characters, but this is not allowed by Literotica. When a new character is introduced, I will put in parenthesis the character's real name so you can look them up on the internet. *** Tragedy struck the Reagan family a mere two weeks after everyone returned to work after the incredible 4th of July org...

Britnee Busted XXX Ch. 11

by gfunk45 on Oct 7, 2019
Group Sex

This is the penultimate chapter of the story. I will probably take a short break after chapter 12 and work on a few shorter stories in the Britnee 'universe". ***** Britnee sat on Dr. Ritter's exam table clad only in a small hospital gown. She was bored and tired of waiting. She looked around and hummed quietly to herself, wondering if the procedure was go...

Swing Club Adventure

by Scorpio08 on Sep 25, 2017
Group Sex

Stacy reread the ad two or three times. "Why not? It will give me an excuse to buy something sexy to wear, which I probably won't have on long," she said, with a laugh. "Are you really sure?" I asked. "I am! It sounds like what we've been talking about. Will the distance getting there be a problem?" "No. We'll need to get a hotel room. We would do that an...

Stocking Wearing Cocksucker

by LuvStockings on Sep 26, 2017
Fetish

This is a story of fiction, didn’t happen, but I can dream, can’t I? It was a Saturday night and my wife said, “I want you to take me to one of those movie/peep shows with you. The ones where you jerk off while you watch the movie. I want to go with you.” “Why?” I asked. “Because I want to see what you like about them. You could watch a porno movie here...

Kate's Heavenly Hell Ch. 02

by Duke567 on Sep 11, 2017
Fetish

For those of you who read the first installment, you already know how a typical week went for us when we had Alexa over for dinner. We had been having here over for 'dinner' on Friday nights about once a month for the last couple of years. This story started about 4 weeks ago. It seemed just like any other week... Kate, my wife, liked to surprised me. I t...

Katrina Gets A Role

by nextcenturyromeo on Sep 19, 2017
Celebrities & Fan Fiction

IMPORTANT: This is only a fantasy. No harm intended to anyone. The sexy, hottie Katrina Kaif submits to this director to get a role in his movie. Please send your feedback. * * * * * It was 10 PM and she was due any minute. She had called me in day to ask if I would see her, she was a successful model, well not a supermodel, just some magazine and TV a...

Shipwrecked Pt. 03

by JJ122964 on Sep 13, 2017
Transsexuals & Crossdressers

I am Sorry, but I have to break up the forum portion of this story. Otherwise it would be too long. I hope you like the series and please comment. Thanks J. ********** The tasting house. I woke up to the feeling my ass being penetrated by something. I was still on the X and being cleaned again. I saw that my loincloth was on the table and the ooze was on...

The First Time I Watched My Wife At

by welshcpl53 on Sep 12, 2017
Loving Wives

After I watched my wife fucking a guy from a local pub in a quiet underpass. It became an obsession for me see her do it again. The problem I had was Kim didn't know that I watched them fucking because I never told her that I seen it all happen. So Kim was quite unaware of what I seen and how much it turned me on. I mean how the hell do you tell your wife t...