Sissy Bikini Stories

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Orientation
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Infinite Scroll

Fender Bender Ch. 03

by SissyAndi on Sep 14, 2017
Transsexuals & Crossdressers

Author's Note: The following is purely fiction and the property of the author. Any feed back would be greatly appreciated. Susan called me early Monday Morning and asked if I wanted to come over and lay out by the pool with her, she told me that Mark had a business meeting and would be gone most of the day so it would be just us girls. I remembered what h...

Shelly and "Jenny's" Story Pt. 02

by akak28 on Sep 26, 2017
Transsexuals & Crossdressers

I saw my wife leaving out of the corner of my eye, and I knew it was time. I hadn't spent 15 years at this company to be fired for no fucking reason. I was a man, and I was going to take what I deserved. I had already decided I was going to talk to Marcus at this party, but when I looked around I couldn't find him. Instead, I found Chantlle, Marcus' wife by...

Kimmy the T-girl

by sissy_in_denial on Sep 16, 2017
Transsexuals & Crossdressers

Introduction: Hello. My girly name is Kim, but in my every day life, I am known as Ken. I am 5"5, 135 lbs. I'm eighteen years old, and this story begins on the last day of school before spring break. I have been a closet cross dresser for the past two years. I started off from stealing my sister's panties and bras and wearing them when I was home, alone, an...

A Mistress to Obey Ch. 03

by gbr2004 on Sep 12, 2017
BDSM

I woke up when she whipped the cover off the cage. I had been able to curl up enough to sleep on my side but when I tried to move I was very stiff. She opened the cage door and I backed out. She told me to go take a nice long shower and that my clothes would be on the bed when I finish. She was wearing a pair of tan slacks and a yellow blouse and looked like...

How I Became Sissy Willow Ch. 01

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

Description: A married cross-dresser's fantasy to dress and serve becomes reality at the hands of his wife and her lover. Fern and I had been married for three years. Our sex life had become bland, routine, and, frankly, I preferred masturbation to the work it took to cum by intercourse. I was pretty sure that Fern felt that way, too. You see, my cock is, a...

Sarah Gets to Wear a White Bikini

by SarahCD on Jan 29, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more detail and corrected some...

Second Meeting with Master Gene

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Friday evening comes finally as this was the slowest week of my life waiting for this day to get here as so looking forward to tonight even though I am still a little leery about becoming a sissy submissive of Master Gene's. I have shaved my entire body and sent pictures for proof as he demanded and now sitting in a pair of my pink with lavender lace bikini...

My Wife Takes Me Much Farther

by Godscountry on Sep 26, 2017
Transsexuals & Crossdressers

It's been three weeks since my wife turned me out at her book club and turned me into a cumslut. That event seems to have really opened up my wife's imagination and made her hunger for more dominance over me. For the last three weeks, she's kept me locked in chastity, even though our deal was that I would be released after the event. She's also made me kee...

Samantha Finds a Dom Online

by SamanthaSatine on Jun 19, 2018
Transsexuals & Crossdressers

A true story - pre-chastity episode from this sissy slut.. It's Friday... It is 9.30am... Text message received "Are we still on for today" her reply "Yes, I believe we said 10am" Bag packed she takes the short journey across town to the meet. Samantha checks in for the final directions having been once before but it is a secure address with locked a...

Jesse's Journey Down a Rabbit Hole Ch. 04

by sadkins116 on Sep 19, 2017
Illustrated

As I mentioned in the previous chapters, this story is a collaborative effort between me and Rebeccsm. She has provided the art, and a lot of the plot, god I love how her mind works, and me for the text. Please let us know how you feel about our efforts. Comments and votes are welcome. It is the only way we will know if you like our work. I would like to th...