Sissygasm Bbc Stories

1,544 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

How I Became a Sissy for BBC

by Caged4goddessd on Mar 12, 2019
Transgender & Crossdressers

It really all started in college. I was a fairly typical and somewhat popular guy. I was involved in a few different clubs and a member of a popular fraternity on campus. Of course, this led to me knowing quite a few of my classmates and at the time I had my share of success with the females in my classes. It was my junior year and at the time I was dating...

Sissy Wants Her Wife's Boyfriend Ch. 01

by SissyArlene on Aug 21, 2018
Transsexuals & Crossdressers

I knew that my secret sissy life was about to be exposed. Cindy, my wife, had been dating real men since my hormone therapy had rendered my sissy clit useless to her, but she was still trying to keep our "unique" marriage hidden from friends and family. Two months ago, Cindy said, "I'm tired of trying to keep your transition a secret Arlene. I'm not going...

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...

First Multiple Sissygasm Today

by JessC on Sep 16, 2017
Transsexuals & Crossdressers

I had my very first multiple sissygasm. I own a fucking machine. It has been the source of much pleasure since I bought it. I decided recently to try for a really great sissygasm. For those of you that don't know, a sissygasm is having an orgasm with a soft cock from ass/prostate stimulation. Well, I decided that I was going to prep myself to have a nice la...

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...

Sissy Pills Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

There's nothing like waking up like this. This being after being fucked. Not fucked but riding a dildo until you have a sissygasm. And yet that's not the first thing in my brain waking up. It's the cum. It's that eating my own cum. And really feeling this need sort of burned in my brain from the semen and the pills. I really, really want to suck a co...

Cockland Island Pt. 06

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

I woke up and I was sucking that realistic dildo cock like a soother and it was so weird and right and made me smile as I pulled it out trying to make my lips do the pop you can do sometimes with suckers. I giggled and did it a few more times then pumped it in and out of my mouth trying to get that dick lips feeling going on. That's a sexy sissy trick, all...

White Boi Learns his Place Ch. 06

by sissyashley4bbc on Oct 31, 2018
Transgender & Crossdressers

Sunday arrived and vacation was over. As I sat in the backseat of the Jeep with Daddy, I could help but think of how much had changed. 4 days ago I was a straight guy on the mend from a breakup just looking to start fresh by getting fucked up with some new friends. While that definitely happened, so much more did too. I was completely seduced by Daddy and...

Simone

by Sissyhalo1 on May 11, 2020
Transgender & Crossdressers

I'm so sick and tired of my life. It was like I'm cursed. I wasn't a great looking guy in high school with bad skin and bad grades because well... I was poor. My old man was a night watchman and mom was a stay at home mom because she was poor and had no real education past junior high when she started popping us out. So everything was tight and for the m...

Family Business

by fantaseeboy on Jul 27, 2020
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Laying on my bed in my room in my mom's trailer, my laptop was set on the table beside me with my webcam aimed where I lay. White, satin, bikini panties were looped around my left ankle. The snug-fitting, stretchy crop top clung to my narrow, smooth chest and left my midriff bare....