Sissy Pills Stories

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Kate's Mom Comes To Visit Ch. 05

by Catytheghost on Sep 16, 2017
Transsexuals & Crossdressers

Part 5 A wedding to plan Carmen OK, dinner was a total surprise for me, that's for sure: Ally and Kate getting married, and Mary putting the fear of the Gods into Maggie. Now that really was a shocker, as Mary gets along with everyone. I even asked her about Lady Jenna using me for her pleasure, and she said, "Honey, you just please her and all will be goo...

Amy Cuckold Brian Ch. 04

by CuckoldGuy on Sep 19, 2017
Loving Wives

Just a little over an hour later the lock clicked open and Chris emerged from the bedroom dressed and carrying his shoes so as not to awaken the children. Brian's cuckolding was completed. Very quietly Chris descended the stairs and looked for Brian. He heard the TV in the den. Entering the den he saw the top of Brian's head in the lounge chair. He softly c...

Compromised Pt. 02

by HorribleHenry on Jul 6, 2020
Transgender & Crossdressers

Many of you seemed to have liked my life story so far Chapters 1 - 5. I am very flattered; what girl wouldn't be? You've motivated me to reveal more about my life and career as a shemale (more of a 'she' than a 'male' if you don't mind). I've got lovely boobs you know. Just one thing, if you haven't read Part ONE you'll make it a little more difficult for me...

Sissy Blane's Liquid Assets

by EvelynT on Sep 14, 2017
Fetish

ONE The Plumrose Dossier I became familiar with the Plumrose Dossier one cool February morning when it was read to me in the private rooms of Madam Harding at the Clinic. I'd arrived that morning for my weekly 'therapy' and had only enough time to hang up my outer clothes in the Sissies' cloakroom and don my Eva Gabor wig before a facilitator poked her he...

Compromised Pt. 03

by HorribleHenry on Oct 5, 2020
Transgender & Crossdressers

COMPROMISED PART THREE CHAPTER EIGHT Park Green Private Hospital specialised, and probably still does, in mending wealthy people, particularly those with kinks. There was nothing that people did to themselves, or each other, that fazed the dedicated staff of the hospital. A patient with a torn arsehole caused by anal sex was very low down on their list of...

A Game within a Game Ch. 02C

by doberinca on Sep 16, 2017
Transsexuals & Crossdressers

Author's Note: This is the second story. I still have sometimes trouble to find the right syntax. I hope you still have fun in reading this second story. A third will be following. The characters involved will appear more 'human', not real good and not real bad, and make sometimes bad decisions. Chapter 2C. Dr. Catherine. The next morning when Rob wake-...

Sam's Panties Ch. 02

by Quietoldie on Sep 19, 2017
Transsexuals & Crossdressers

At the end of their holiday the two couples exchange email addresses and phone numbers. Jean and Ken live in the North East part of England whilst Mike and Sam live near London. The 250 miles separating them is no bar to them meeting up from time to time when Jean can enjoy her new found desire for extramarital sex with both Mike and Sam. Her cuckold Ken is...

The Bottoms of My Heart

by SEVERUSMAX on Jul 3, 2018
Group Sex

"And then there's me, but I don't believe in such stupid taboos, anyway. And you have some dirt on me as well, don't you, at least by the same idiotic moral code that so many give at least lip service. I don't personally give a fuck. So, be that as it may, perhaps we should kiss ... and make up, eh?" Marsha told Howard and Kristin with a wink. "Or maybe I c...

Backdoor Man - The Missing Chapter

by SevMax2 on Jul 14, 2020
Group Sex

Having settled the matter of who owns whom by everyone agreeing that I owned them all, I was very much engaged in what turned into the Orgy To End All Orgies, or so it seemed that evening, as we fucked our way far enough into the evening that by the time that we were all hungry, we didn't have time to cook. It was partly the fault of those blue pills, which...

Steve to Stevie to ?? Ch. 06a

by gbr2004 on Sep 13, 2017
Fetish

Ms Storm has videotaped me begging to suck her cock, and sucking it, and letting her cum in my mouth. I have been informed that if I don't do as told, everyone close to me will see a copy of the tape. I had been made to dress rather fem and go back to the gay lounge and hang around with some sissy fag boys. I even showed off for other men and let them watch...