Sissy Bikini Stories

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Feminizing First Step Ch. 04

by antares34 on Dec 10, 2019
Transgender & Crossdressers

(All characters are age 18+) It has been months since my mom and therapist started my sissy transformation. So many changes have happened! Shortly after placing me in a chastity device, they revealed to me that the "male hormones" I thought I had been taking were in fact just the opposite -progestogen and testosterone blockers to be specific. To be honest...

Feminizing First Step Ch. 06

by antares34 on Jun 1, 2020
Transgender & Crossdressers

(All characters are age 18+) Today my mom was having her friends over for a pool party in our backyard. They had been here all afternoon --mainly lounging around the secluded swimming pool and patio area. Michelle had been first to arrive. She was my mom's old roommate from university and came wearing a black bikini and floral print sarong. Next was Kendra...

Halloween Pool Party Pt. 02

by sissymissyct on Sep 15, 2017
Fetish

Maddy Returns I noticed Miss Maddy getting dropped off at the main house around 10 am. I did a quick final check of the pool room and my "pink" room just in case I forgot anything and around 11 Miss Maddy came in. She greeted me warmly with a light peck on the cheek and asked, "How's Ronnie doing today? I have missed our time here in the pool house". Why do...

My Sissification Ch. 02

by sissy171 on Aug 31, 2020
BDSM

I had always planned to go to college, but I was already fairly secure in my business, so I entered college with no scholastic trepidation. My way bigger fear was that I was still sporting a bikini tan, which kept me conflicted; fearful of being discovered, constantly on a sexual edge, and woefully missing Beth. The bikini bra outline was her "brand" upon...

Feminizing First Step Ch. 03

by antares34 on Oct 21, 2019
Transgender & Crossdressers

(All characters are age 18+) *** I felt like I was losing control. My body and mind were becoming less and less masculine with every passing day. And I was secretly ENJOYING it. I couldn't help myself. Every time I looked in the mirror, I found myself loving the ever-changing reflection. First, my dyed pixie haircut. Then, my bikinis. Then, my nose, ear, a...

Marine Girl Ch. 02

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 2 - Bikini Girl The walk from the changing room to the outside pool meant a lonely exposed trek across the cold wet tiled floors. In front of the whole wide eyed class who all laugh like crazed hyenas. Sir was joined by Miss the girls tutor who looks at me sympathetically. 'Have you met our new girl?' Sir says briefly explaining the situation to...

Sun's Out, Bums Out

by Sissylexy on Sep 21, 2020
BDSM

"Lexy, come here," Miss calls, she sounds cheerful. I get up from the hall, where I have been kneeling naked for the past 2 hours. Despite the sunshine outside, there is a chill in this small room. I struggle to my feet and skip into the living room, hoping that Miss is as playful as her call to me suggests. "Sit on the floor Lexy, by the sofa, facing the t...

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

The Ex That Kept Me Pt. 03

by sissythongluv on Sep 15, 2017
Transsexuals & Crossdressers

I peeled my panties off and took off the rest of my things, not that it did much. I quickly searched through the bags, finding the pink itsy bikini and matching bikini top. I slid the bikini up legs and did my best to tuck my itty boy clit away. Kate knocked on the door, "hurry up sissy!" I put the top on quick before opening the door. The apartment looke...

Master and Four Subs

by totk6432 on Apr 17, 2018
Fetish

This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. ======= The rule is simple: I ring the doorbell and let myself into Master Daddy's house. Susan, my 25 year old personal assistant, is with me. She is in charge of me at work. Sh...