Sissy Pills Stories

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Jerry becomes Jill Pt. 05: July 4th

by gasissynora on Apr 27, 2020
Transgender & Crossdressers

Jerry becomes Jill: Part 5: July 4th Week End This is the fifth part of my story about how I became Jill. After having started female hormones, Jill is introduced to group play by Mistress Rikki. The Fourth of July is on Monday and that Thursday evening at dinner Mistress gives me some information about the holiday weekend. She says, "Tomorrow you are done...

Tranny Chasers: Shirley and Chrissy

by 1946EW on Sep 12, 2017
Transsexuals & Crossdressers

Shirley looked around as she entered Cavalier d'Eon, hoping to spot Ron and Bernie. She had promised that she would be there, and fully expected them to be waiting for her. Her survey caught the eye of many a hopeful tranny chaser. She had not known of the breed a week earlier, now she could spot them with ease. And there easily were over a dozen or two at t...

Wife Humiliates, Hubby's Turned On

by Quietoldie on Oct 21, 2019
Transgender & Crossdressers

The wife Carol is the main narrator of this story with some comments from her hubby Bernard. I've tried to give a slightly different twist to cuckolding and cross dressing compared to many stories on Literotica. ***** CAROL "You're not much of a man are you?" I said to Bernard. I was angry and unfairly blamed my hubby after receiving the news that his spe...

Braincocked

by Sissyhalo1 on Nov 16, 2020
Transgender & Crossdressers

I saw the ad. Psionic experiments ongoing, volunteers are requested. And there was an e-mail set of links and snail mail there. I looked into it. Honestly I was always interested in this stuff. And now with Covid...I was out of work and needed the money. There was some back and forth and there was no pay. But there was a room, they owned an old motel...

Contentment at Last

by Sissyelaine on Nov 26, 2017
Transsexuals & Crossdressers

At school I was hopeless in class but excelled in all sports and in art. I left school as soon as I could and much to the amusement of my friends and family, I started a hairdressing apprenticeship in Mayfair, London. I worked hard and became very much in demand but to the outside world I played all the manly sports and chatted to all the girls maintaining m...

Fantasy to Reality Ch. 02

by CuckoldDesires on Sep 15, 2017
Transsexuals & Crossdressers

I faded in and out of consciousness My mind was pulsating from the excitement of a glorious dream, it involved a sissy kneeling subservient at the feet of her master, a single drop of cum dripped from her bottom lip and landed in the small puddle on the floor. The sissy's eyes looked up at the recently serviced glistening cock, thick and bulging from the hu...

Miss Guided

by MissMarianne on Mar 12, 2019
Transgender & Crossdressers

My name is Susan and my husband Charles, we are both 25 years old and have been married for one year. Recently Charles has been very depressed and He lost his job when the company moved to Malaysia. Lately his performance in bed has been sub-par and , in fact, he can't get it up most of the time. We feared he was becoming impotent but the doctor said the pro...

Anklet Adventure Pt. 02

by dometoo on Oct 29, 2018
Interracial Love

Day two of our cruise started with the sun shining through the open balcony slider and a slight, warm breeze dancing over our naked bodies. The rhythmic sound of waves breaking against the hull was memorizing, almost hypnotic. My beautiful wife of 20 years and I lay exhausted on the cum stained sheets she and her bull made without me last night. We were both...

It?s Either Break Up Or Make Up

by felicia_rene on Sep 12, 2017
Transsexuals & Crossdressers

PART 1 Synopsis: I always was put off by the unsuspecting stupid love sick, pussy whipped guy is transformed against his will because the will wants to run off and have an affair, I never understood why they don't just pack and leave. The underlying theme is transformation and sexual punishment of the main character with anti gay womanizing feeling for hi...

My Medical Vacation

by sissymissyct on Jul 10, 2019
First Time

BRENDA'S MEDICAL VACATION by Brenda Finally on the way to the airport. My first trip to Europe. I wish my wife was coming with me but she was just dropping me at the Laguardia international terminal. I certainly hoped we would get to go to Europe together and do the normal sightseeing and partying that most couples enjoy, but this was a special trip for me....