Sissy Pregnant Stories

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Reality TV

by JJ Neal on Sep 25, 2017
Transsexuals & Crossdressers

I didn't recognize the number, but I certainly recognized the voice and understood the message, 5:30, Jackson, Bride. My Master isn't given to long conversations with me, or any explanations. My role is to make it happen. I met Master Fred in a sissy chat room and he swept me off my high-heels. By way of background my sissy name is Jamie Jo. I'm 44-years...

Covid 19 - Pete Turned into Charleigh Pt. 05

by His_fag_wife on Sep 14, 2020
Transgender & Crossdressers

It was a long night, Charleigh drifted off, but the warmth in her ass, the stretch and lack of comfort as her hands were padlocked together made restful sleep almost impossible. She kept on drinking but in the early hours became aware of an ever increasing need to piss. She thought she'd be able to hold on, but she was getting more and more desperate. By 5...

The Sexy Cuckold Couple Pt. 10b

by cuckcpl4play on Sep 19, 2017
Fetish

Precursor: This is part 10b of the series and it is about the fantasy we have as a cuckold couple. We have engaged in many acts of cuckoldry, but the story itself is fiction. If you are offended by this type of lifestyle than please don't read. It amazes me that we continue to get such negative comments to this series from people claiming that we are uneduca...

Young Sissy Ch. 02

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

I was walking in a field, the cool grass crushed softly between my toes, the sun warm on my skin, the smells of spring were in the air and every deep breath I took filled my lungs with the promise of a fresh start and new hope. The sky was a flawless blue and looked clear enough to take a swim in. Everywhere I turned, all I could see was endless rows of roll...

Owning The Girl Next Door

by Frognut on Sep 11, 2018
Sci-Fi & Fantasy

Chapter 1 The Beginning It started one afternoon after I had gotten off work with my Dad, I was tinkering with my car in the driveway when I hear my name being called. I looked down the street and a friend of mines girlfriend was walking to me, I said hey Sherry what's up? she asked what I was doing tonight? I said going to cruse the beach for a couple...

On the Beach Ch. 03

by Turbidus on Sep 25, 2017
Exhibitionist & Voyeur

The fallout from the previous night's festivities continues... Thanks to LarryInSeattle for his editing. Any errors that remain are my own. ***** I gave up on the idea of jerking off. Something was going on with Bill. I realized that this was the first time in my life I was worried about my brother. He'd never gotten in trouble. He had been about the l...

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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Eve Quest Pt. 02

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed so much more acceptable than an enema. I tossed my gown on the bed and fill...

My Fat King

by ChewToySub on Sep 16, 2017
Transsexuals & Crossdressers

I always wanted to be owned. I wanted a big man to have me, keep me, use me for his pleasure. I don't think it's anything to do with power, I think I just like pleasing people, but with men I just love going that extra further and showing him how much I want him to be happy. So I surrender myself. He can do whatever he wants, when he wants, my body is a toy...

Card Shark

by Turned on Sep 14, 2017
Loving Wives

I returned to my hotel room from a poker tournament and realized I'd forgotten my key, so I knocked. After a few moments the door swung open and my pretty, young asian wife was waiting for me behind it. "Hi honey," she said, giving me a very strange look, "How did you do in your poker tournament?" "I did ok. Third place. I made a little money," I said, s...