Sissy Enema Stories

10,114 results
Orientation
Length
Source
Infinite Scroll

My First Time Sucking Cock Pt. 05

by katiecdsub on Sep 16, 2017
Transsexuals & Crossdressers

I teasingly undid his pants as I laid in the bed. I giggled as his big hard cock sprang out of his shorts as I pulled them down. What do I do with this I asked shyly? You are going to ride Daddy now boy, he said. He then tugged off my shorts and then pulled off my shirt. Doesn't daddy want me as a girl today? Plenty of time for that later. Lube up sissy and...

Opening Him Up Ch. 03

by humbleboy on Sep 12, 2017
BDSM

Amy laid down next to Tim exhausted. “Tim, now I want you to suck on ALL that cum you just shot in my pussy.” Tim without a word placed his mouth on her trimmed pussy and began to suck and lick her hot organ. “That's good. You love this pussy, don't you?” Amy had always liked the way her husband eat her out, but now it was the power trip getting her off. “D...

Hung like a Grape Ch. 03

by sissysherry2 on Apr 10, 2018
Transsexuals & Crossdressers

The story of our sissy heroine concludes... this is the third chapter. Lisa had pegged and tagged Sissy Sherry in the last chapter and took her shopping for new lingerie for the evening's festivities. She opened the door in a sexy pink nightie with full makeup. I plan on concluding the tale here but that will depend in how well it is received. Thanks to th...

I Love my "My Cum Slut"

by Red10Dog on Feb 26, 2019
Transgender & Crossdressers

Getting a text saying "I need my cum slut." I rush to get myself ready. While taking a shower, I take the time to shave my entire body. Giving my self an enema, and I clean my boi pussy hole. Making sure I am perfect for you. Applying my makeup and bright pink lipstick that screams "I want to suck your cock." I lock my cock in a cage because he says it's...

Unexpected Mistress Ch. 03

by Scottt on Nov 16, 2020
Fetish

Paul is pushed to his limits in this installment. Deborah accepts her role as Mistress, and is empowered by it. I hope you all enjoy chapter three...I had a lot of fun writing it. I awoke early, and showered and shaved. Debs white bikini was scattered about in our bedroom, and I put it on. I fixed her breakfast, and at seven o'clock started her massage. Deb...

Recruiting of a Sissy Maid Ch. 08

by Sissy_Chantel on Oct 15, 2017
Transsexuals & Crossdressers

Chapter Eight: Chantel Moves Up at The Jade Maid Club. Six months now into Chantel's new life as a t-girl maid and slut at The Jade Maid Club has her progressing well. Hormones have aided in her feminization and she has proven to be a very good and docile enslaved sissy girl. Not perfect but impressive to see that Mr. Luftgrin, Mr. Jenkins in reviewing all...

Bird of Prey Ch. 14

by Sputnik57 on Sep 14, 2017
BDSM

The women now gave their full attention to the newly subdued mail; he would be like this permanently without the need for drugs within a few short weeks. Gloria retrieved some of the more expensive of the ex-owner's wine from a cabinet and the three stood triumphantly over Fox-Janner, who was pacified by the drug but able to comprehend what was happening as...

The Prostate Exam Pt. 04

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by not being able to resist pushing back against her finger, forcing her finger deeper into asshole. At that point his female doctor had decided to test just how submissive he was. She gave him the option to back out if he...

Uncovering the Sissy Beneath Pt. 04

by jefferyscott745 on Jul 10, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part four of my previous work. Be sure to read parts 1-3 if you wish to understand the background of this section. After we reach the bottom of the stairs, Madam Victoria leads us back into the cell. She locks the sliding bars, and b...

Danni Ch. 02

by Coder3445 on Jan 20, 2020
Transgender & Crossdressers

This story starts where the last left off, read Danni to understand what is going on in this story. Of course all character are above the age of 18. The following story contain feminization and female domination. * Also another description Tara, Danni's Mother Unlike Danni Tara had tanned skin, she was five foot four inches tall. She had green eyes and...