Sissygasm Chastity Stories

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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...

Toby

by Sissyhalo on Sep 4, 2018
Transsexuals & Crossdressers

I found my real self the start of this year. A sissy gurl. Okay so, going back I sucked at being a guy. All through high school I never got laid. Not even close. I was a little short compared to the good looking guys at five six, I had unfortunately this whole soft chin thing and was never conventionally good looking. Add that to me being poor. Oh ye...

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...

White Boi Learns his Place Ch. 03

by sissyashley4bbc on Jul 10, 2018
Transsexuals & Crossdressers

After the group decided we should go to our pool, Emily came up to me and told me she had a bathing suit I could borrow. Daddy told me to go get changed with her, and the guys would start making drinks and rolling joints to take outside. I guess he didn't need to change really, all he has on was athletic shorts that would dry quickly. I followed Emily upst...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Caught in the Act

by taodie on Oct 6, 2020
Transgender & Crossdressers

As you sit watching TV while your wife gets ready for a girls night out, you are not able to pay attention as you just feel your penis strain against the chastity cage. You had been looking forward to this night all week knowing you would have it to yourself. It was during these rare moments where you could fulfill your girly desires you had never dared shar...

Cockland Island Pt. 02

by Sissyhalo1 on Dec 3, 2019
Transgender & Crossdressers

I knew I was messed up in the head and didn't care. I knew I was getting brainwashed but didn't care the videos, the drugs, the sex. These nice, big, muscular, handsome guys were there eating with us as we shared a table and were being really nice to Jill and I. In my normal life people are just sorta nice, not nice in this way. It was kind of cool and y...

White Boi Learns his Place Ch. 02

by sissyashley4bbc on May 30, 2018
Transsexuals & Crossdressers

I slept like a baby that night after the fucking I just received at the hands of Steve's big black cock. It was hard to believe that earlier that day I was a straight white guy sitting at my desk at work looking forward to a boozy cabin weekend with an old (and some new) friends. Now, I'm being little spoon for a black man who just took my sissy virginity, w...

From Her Ex-Boss to her Bitch Pt. 05

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story includes extreme themes of sissification, interracial domination, watersports, cock sucking, if any of these themes are not your thing, please don't read it. ***** "I think you should have tattoo on your back above your pussy cheeks and another above your little Sissy clit." "But I couldn't do that Master, my wife would see." Amber was almost b...