Sissy Enema Stories

10,114 results
Orientation
Length
Source
Infinite Scroll

Husband Turned Fuck Hole

by Sjen451 on May 2, 2018
Transsexuals & Crossdressers

I'll share a sexual story with you. I'm in my early 30s now and have spent years exploring myself, especially my boipussy. Now it's even more exciting and pleasurable for me to fuck my ass than it is to masturbate with my cock. But that's not really something you can tell anyone, so I'd buy sex toys when I went out of town for work, had wonderful fun in...

Turned into a Slut Ch. 04

by xaitonnar22 on Sep 19, 2017
BDSM

After grabbing some quick sandwiches, Jennifer and I returned to her home. We found a note on the kitchen table from her parents letting us know that they would once again be out of the house for dinner. They didn't expect to be back until ten o'clock, it was seven right now. Once in her room, Jennifer commanded me to strip out of my jeans and bend over the...

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...

The Backpack

by ~Etoile~ on Jul 31, 2011
Fetish

Moving to a new place is always rough, but it can be rewarding as well. The Nuwisha Design College in Seaside City is a smallish school, but is known for its art and design classes. A lot of literature and word-of-mouth shows that graduates from this school often get very lucrative and popular jobs. Lucky for you, you were able to get in with some of your gr...

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The Marriage of Martin Hastings Ch. 15

by rik581 on Sep 12, 2017
Transsexuals & Crossdressers

M artin was in stunned silence as he walked hand in hand with Dorothy back to the house, their fingers interlocked. As they reached the house, Dorothy turned to face Martin and then, lowering his lashes, took Martin's hands in his hands and raised them to his lips and kissed them. "Good luck Martin," Dorothy said as he pulled Martin close. He kissed Mar...

Sissy Auction

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Authors note: this story is a fill in while I get over a block with the fifty shades part three. I also need to revise part two of sissy downfall as Literotica rightly pulled it due to excessive violence. I wish this story was autobiographical. It's not but has some elements of truth in it. I hope you enjoy reading it. I love feedback; even negative. All cha...

You're Like a Little Boy at Times Ch. 05

by Myneed on Oct 13, 2017
Fetish

This is a slightly twisted femdom love story of James and Mel, his Mistress. It will make most sense if the chapters are read in order. In the last chapter, Mel's boyfriend, Tim, left the costume party with Tiffany. Mel made James, who is dressed as a girl, cum in public. I hope you are enjoying the series. All characters are over 18. ***** The party co...

To the Manor Bound Ch. 02

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This is part two of a series; you'll probably need to read part one to get a grip on what's going on. As with the first part this focuses on forced feminisation including aspects of BDSM and non-con, so if that's not your thing, now would be the time to leave. Chapter 2 -- The Next Day Peter was barely able to find a second's worth of sleep that first nigh...

Making of a Porn Queen Ch. 04

by Scribler on Sep 25, 2017
Transsexuals & Crossdressers

On Monday we woke up early. I knew I was excited to go to my first porn shooting and Maria was excited to be working again. I dressed in my maid's uniform but I knew I would be changing as soon as both Tracy and Mark were dressed to leave. Mark would go in early with Maria and I following about an hour later. Tracy was coming along too but she said she would...

The Sexy Domme Next Door Ch. 02

by rickiee_2002 on Sep 19, 2017
BDSM

"Rickiee, you may get dressed and go home. I no longer need you today." Mistress Rebecca said in a serious tone. "Is there something I did wrong, Mistress? I asked. "No Rickiee, I am through with you today. You will return at 7:00 a.m. on Saturday morning." I looked at Mistress Rebecca. I was wondering why Saturday. I was about to ask ... "You will retur...