Sissy Bet Stories

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My Submission to a Real Man

by gbr2004 on Dec 28, 2017
BDSM

This is total fantasy and would never do many of the things I discuss. If not into really kinky play, humiliation, verbal abuse, and forced fem and strong discipline, please pass on this story. For all you other submissive boy and dominant men hope you like my fantasies. ***** MY SUBMISSION TO A REAL MAN It was our first actual meeting. We had emailed bac...

Cruise Ship Cuckold Ch. 08

by Angelscuck on Sep 14, 2017
Novels and Novellas

Story from Angel's point of view: My husband asked me to write this next installment due to the fact that he is a bit tied up at the moment. I am more than happy to tell you our story. As you may or may not remember, my husband and I were in the captain's wife's cabin with him and his nephew Daniel. We were there to pay up on the bet my husband lost to Ev...

The Bet

by ksu328 on Aug 31, 2017
Fetish

Let me first setup the situation, I have been friends with this guy for about the last 10 to 12 years. His girlfriend, Tyler, had this friend named Jen. I was totally in awe of Jen, she was so beautiful. I am not exactly good with the ladies, so when I finally asked her to go out, she gave me an emphatic "NO!!" So now she knew that I liked her, she took full...

Do I Want To Leave My Wife?

by Gretatv on Sep 16, 2017
Transsexuals & Crossdressers

Dear Readers, hope you enjoy my little fantasy. * I sat there thinking, turning my glass between my hands, not listening to what was happening around me. Why did it happen? Once again I had had a quarrel with my wife. This time it was too much. I knew I shouldn't have raised my voice and yes I should have been calmer and maybe even docile to her. I mean it...

Panty Jerkoff Encouragement

by dirtywordygirl on Sep 13, 2017
Exhibitionist & Voyeur

Right now, I just want you to lay back on the bed and show me what you have down there... No! I DIDN'T SAY YOU COULD TOUCH IT! That's very naughty of you to do that. First you have to ask me, so let go of your cock and show it to me like a bad little girl...you're a very bad little girl, aren't you? Let's get you a little wet and slippery, ok? Ask me if y...

The Training of Sissy Paula Ch. 4

by submissive~pet~ on Sep 14, 2017
Fetish

Mistress Carolyn Found the biggest cock she could find. He had to be 16 inches and his cock was fatter than my wrist. He told Mistress it takes him around 4 hours to cum. Mistress told me she would not make me try to swallow his big cock, but it would be visiting my asshole that night. I was dressed in my red velvet mini, no panties, silicon breast as big a...

Turned So Totally

by gbr2004 on Oct 8, 2019
BDSM

It was our first actual meeting. We had emailed back and forth about what we were both looking for and found we had similar interests. He wanted to take a straight acting guy, take his masculinity away and turn him into his submissive sissy bitch. That is what I had been thinking and fantasizing about continually but could I actually do it? From our email ex...

Betrayed by Her

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

I am surprised when Her husband answers the door and mumble hello awkwardly as He smirks at my discomfort. "Come on in," He offers expansively letting me in the door. He stands close while I shut the door steadily forcing me into the corner. "She told me about you," He whispers. "Huh," I grunt not wanting to believe what He just said. "She told me about yo...

Girl's Night Pt. 03

by DifferentBreed on Sep 14, 2017
Fetish

Fisher climbed the stairs slowly, wary of the quiet that hung over the upstairs. As he hit the landing a soft moan emanated from the bedroom and his heart raced as he entered the doorway. There, framed in the soft light of the bedroom lamps, was Sophie kissing another woman. Her crisp white shirt was unbuttoned, exposing the top of her supple breasts, and gi...

Doing Three Ch. 2

by Royal_Prince on Sep 12, 2017
Loving Wives

Chapter 2: Submission I had been lying on the couch most of the night wondering where the night had gone wrong. At first fantasy after fantasy was coming true. I was able to watch my lovely girlfriend make love to the beautiful sex goddess Mary and then watch her explode into an orgasmic frenzy on Mary’s husband’s 8-inch cock. Both Angel and I had fantasi...