Sissygasm Stories

121 results
Orientation
Length
Source
Infinite Scroll

Strawberry Milk Pt. 03

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

Now I was planning on going home for Christmas but given how I was changed and changing I'd need some sort of plan and to spend some thought on this. In the meantime I have a few things I wanted to do and that's well... Milking my titties and blending that milk into some of my body lotion and then going out for a walk, get some groceries and do some clothe...

Family Chastity Story Ch. 03

by antares34 on Jul 30, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My gimp son and I have settled into a routine. Permanent chastity with monthly releases. These releases occur on the first day of every month. I...

The Gender Pill Pt. 02

by MadisonWillow on Sep 14, 2020
Transgender & Crossdressers

**I highly recommend reading The Gender Pill: Part 1 to catch up on the storyline. To do so, view my works on my profile page, and please read my other works! Thanks for reading :) ** The Gender Pill: Part 2 I didn't always want to be a woman. Up until the age of 12, I don't remember ever wanting to try on female clothing or feeling as if I wasn't the boy...

Caught Out, Made Over

by TanyaCc on Oct 5, 2020
Transgender & Crossdressers

It had finally happened. To be honest, I shouldn't have been that surprised. But here I was, dressed in my favourite sissy school gurl outfit, heels on, lipstick, wig and chastity cage in place, bent over the kitchen bench, getting reamed to the hilt by an 11 inch dildo on the end of my own fucking machine. I had cum dripping down my thighs, moans and groans...

Sissifying Addictions

by Sissyhalo on Nov 25, 2017
Transsexuals & Crossdressers

They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it. It's somewhere in between and none of it either. It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass. It started for me...

Daddy's Little Sissy Diaper Slut

by Satanicsissybitch on Jul 14, 2020
Transgender & Crossdressers

I absolutely love wearing my adorable pink pull-ups for Daddy and I really love being his cute little sissy diaper slut! Daddy had always loved playing the dominant role with women but it was me who has him addicted to sissies and I've always been a little diaper slut. Well, a pull-up slut anyway. I always felt the adult diapers were not only boring and blan...

Coach Daddy Ch. 06

by whatcouldofbeen on Sep 25, 2017
Transsexuals & Crossdressers

I'd like to again thank teddie_grl for her awesome service of reading through my work. You are awesome. Also, the highlight of my day is getting feedback from my readers. Thank you so much and I am sorry it took me so long to get this chapter out. I hope you like it. ***** Daddy got up out of the bed and I admired his incredible body as he stood there loo...

Yet Another Story

by neoview on Nov 26, 2017
Transsexuals & Crossdressers

You're back? I guess my previous story was a hit. The comments stroked my ego enough to write this bullshit. Before I begin, shout out to: Anonymous user, Anonymous user and xploring96 for the feedback. If it wasn't for you guys I probably wouldn't even bother to continue this... I guess I should make it a series... Naaahhhh. Too confusing. Super narrator p...

Sissy for Mommy's Nipple Cream Ch. 03

by ppeaks42 on Mar 6, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Recap ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ While raising her son Jim as a single mother, Julia developed a special bond with him by never stopping breastfeeding, which had the side effect of growing her breasts to a monstrous H-cup. Once Jim hit puberty, Julia made him start d...

How I Became a Sissy Slave

by Sissy_Sasha on Jul 27, 2020
Transgender & Crossdressers

I had never been so embarrassed in my life. The woman in front of me looked at me with disgust that burgeoned on fear. Seconds prior, I was knocking on her door and ringing her doorbell expecting for a man to answer. This man was Anthony, or at least that's the name he'd given me when I asked. We'd met online a couple weeks ago on a gay dating site. For a...