Sissy Boyfriend Stories

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She Forces Me into Cuckoldry

by hismasterdivine on Sep 25, 2017
Loving Wives

This is my first fiction and features many aspects of cuckolding and BDSM. Forced feminization, spanking, body worship etc play a part in this tale, where a deluded subby boyfriend's thoughts run riot. If the story is a success, I might write a follow up, particularly due to its frustrating climax! ***** Dominant girlfriend wants a black lover, deluded b...

Neighbourhood Terror to Sissy Pt. 17

by Fibaro on Feb 3, 2020
Transgender & Crossdressers

Chapter 19 The drive back home was pretty uneventful, Lisa just sat behind the wheel smiling ear to ear. She had had an awesome day so far, making out with two gorgeous women and now she would spend some quality time with her sissy boyfriend. Marcy was very worried about that quality time. She hoped for sure that it wouldn't involve that dildo going up her...

The Blackmailed Sissy

by jmanrules on Sep 13, 2017
Transsexuals & Crossdressers

Jon walked into his roommates bedroom looking for the phone charger he loaned Eric the night before. As Jon was looking around he saw several pairs of panties, bras, and pantyhose. Not thinking anything of it Jon just grabbed his charger and left with it in hand. After he sat down it dawned on him that Eric has never brought a girl over and even if he did th...

Black Cuckolding Journey Trois

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

Salutations, my friends and devoted readers. Wanda Philogene here. Your favorite Haitian dominatrix, taking the beautiful City of Brockton, Massachusetts, by storm. Ladies and gentlemen, I have some good news. I've dumped Sean Prescott, my favorite white dude, on account of him becoming possessive of me. Sean and I were cool, and we had some fantastic sex, b...

Mistress Chantel, Tranny Dominatrix Ch. 03

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Three: My Saturday Meeting with Kerri. Well another busy but fun week for myself as Mistress Chantel begins to wrap up. It's a bright, sunny Saturday morning about 7:30am. My typical femme routine is to shower, dry off, moisturize with fragrant, moisturizing cream then to shave my face. Luckily for me in recent months I have begun to use a beard ret...

A Well Groomed Sissy Boy Pt. 02

by keptsissy on Jun 19, 2018
Transsexuals & Crossdressers

I was scared to death. I think I was visibly shaking, at least it felt like it. I was at the door as soon as my doorbell rang dressed as my boyfriend told me to dress—to kill. I had on a micro-mini soft pink flexible tight rubber skirt. It was so short you could see the soft little head of my penis if you looked just below the bottom of it. My butt was lubri...

Chastity with Ex as Keyholder Ch. 03

by chastity_sissy on Mar 12, 2019
Fetish

Back at my apartment, I wanted nothing more than to just get the chastity device off of me, but I still couldn't help but be aroused at my humiliating situation. Here I was, chastised by my previous girlfriend who now controlled not only my orgasms, but whether I could have sex with another woman. Suddenly, my phone buzzed, notifying me of a new text messa...

Sissy Keven Jeanne Bardot

by nancyvasquez on Sep 14, 2017
Erotic Couplings

After Jinky and I had been married about a year, she began to make gay references about me being gay. When I'd get mad, she'd laugh and say, "I'm only joking!" I remember she always used to squeeze my breasts, which were quite prominent, and say, "Wow, sweetie, nice development!" And then she'd laugh. My feminine breasts had been a source of embarrassment f...

BoyTrainers, Inc.

by LicoriceOrElse on Sep 19, 2017
Transsexuals & Crossdressers

Peter was taking a long time in the shower again that morning. His mother pressed her ear to the door, and detected soft moaning. Inside the shower, Peter stood, pumping his penis with his hand, eyes squeezed shut. He was a little underdeveloped for 18 – short for his age, and didn't seem to be going through the final stages of puberty just yet, but he was...

I Learned My Lesson Well Ch. 03

by Angelscuck on Sep 2, 2017
Exhibitionist & Voyeur

Well the weekend had arrived. My Fiancé, Angel, had given me a complete makeover at the salon. I looked ridiculous in my maid's costume with full makeup, heels, stockings, garter belt and leach with collar. She looked amazing with her slutty makeup, hair worn up and completely naked under her trench coat. We were on our way to her gangbang. Her black maste...