Sissy Bikini Stories

40,840 results
Orientation
Length
Source
Infinite Scroll

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Sarah Shows Off Her New Panties

by SarahCD on Dec 12, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some grammatical mistakes. *** I was posting a picture of me wearing black ruffled panties on a "Men in Panties" website when I remembered something naughty th...

Cheap Sissy Whore To Call Girl Ch. 03

by HardSoft on Sep 15, 2017
Transsexuals & Crossdressers

My first few days at the hospital wasn't the typical hospital stay. I'd get fucked by everyone who worked there. Most of the time I was too dazed to realize what was happening but there was always a cock or a pussy that needed attention. The doctors would come in during their breaks to ass fuck me. The nurses would make me lick their pussies clean. I didn't...

The Domme Club: The Fucking

by NancyPan on Sep 14, 2017
Fetish

This story will likely be most enjoyable if it is read after reading The Domme Club and one or two other stories in the series (for background of Tom and Monica's relationship and how Tom has previously been humiliated in front of the Domme Club.) Respectful comments are appreciated. ***** Mistress Monica left Tom the standard list of chores to do while s...

Black Licorice

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

My name is Jamie. I am 19 years old. This is the story of what happened to me Halloween one year ago. It was the last week of October and the leaves had turned brilliant shades of orange, red and yellow. The nights were getting cooler. Everything you could imagine was pumpkin flavored. Usually I get psyched for this time of year but things were different f...

A Day at the Beach

by lorenqt on Sep 14, 2017
Transsexuals & Crossdressers

I lay face down on my towel, basking in the sun, almost falling asleep. My boyfriend Jake, he would be my husband if it were legal where we live, walked up and sat next to me. He gently stroked my left arm, "The water is great, Loren. You should try it." Without opening my eyes, I turned my head towards him, "I think I'd rather just lay here in the sun." H...

The Ex That Kept Me Pt. 02

by sissythongluv on Sep 15, 2017
Transsexuals & Crossdressers

I nearly passed out, just lying on the floor, my ex's new boyfriends cum mostly gone, but leaving a sticky feeling on face. I couldn't believe the slut I had turned into once I started sucking that beautiful cock. I understood why me ex couldn't help herself cheating on me. My boi pussy tingled as I wondered if Jack would fuck me. The door creaked open and I...

My Medical Vacation

by sissymissyct on Jul 10, 2019
First Time

BRENDA'S MEDICAL VACATION by Brenda Finally on the way to the airport. My first trip to Europe. I wish my wife was coming with me but she was just dropping me at the Laguardia international terminal. I certainly hoped we would get to go to Europe together and do the normal sightseeing and partying that most couples enjoy, but this was a special trip for me....

Sissy Boy Chuck Becomes Just Sissy

by Krazy35 on Sep 14, 2017
Transsexuals & Crossdressers

A long time ago, I realized that I had a thing for women's clothing. I used to sneak into my sister, Jessica's room and get all dolled up in her clothes. She was a year older than me, but we were practically the same size. I got an incredible hard-on looking at myself in her full length mirror. I quickly undressed, put everything back the way I found it, the...

Yes, Mommy Ch. 03

by searic on Sep 17, 2017
BDSM

Here is the third installment of a story of loving spouses, the husband a sissy submissive to his Mistress/Mommy. She has invited over a girlfriend to witness and perhaps participate in his humiliation and degradation. At the end of Part II, the women were on the couch and the little sissy was on the floor. He obeys his wife's command to beg. * "Oh, please...