Pregnant Sissy Stories

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AliExpress and Sissy Downfall Pt. 10

by His_fag_wife on Jan 23, 2019
Transgender & Crossdressers

As Charlie with her head raised off the cushion admired her new sissy pussy, she felt a complete head rush. As she and Tim had discussed just one guiche piercing at such length, over and over, texts flying back and forth on the crest of a wave of horniness and a submissives deep desire to please, she had fixated on the idea of being pierced without her wife...

A Little Bit Feminine

by ThatGuyMan on May 12, 2020
Transgender & Crossdressers

"Are you sure I can't help?" The reply was cut short by the sound of Jason retching once again. The sound came from their bathroom at the end of the bed, where it had for the last five minutes. Tammy leaned up in bed, concern on her face, as she made to kick the sheets off and go help her husband. Jason, ears like a hawk despite currently revisiting last n...

Uncovering the Sissy Beneath Pt. 07

by jefferyscott745 on Aug 6, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part seven of my previous work. Be sure to read parts 1-6 if you wish to understand the background of this section. Three days had gone by, since Sherry and I had our intimate session together. We had practiced multiple times after t...

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...

Playing Pregnant

by theonewhowas on Sep 16, 2017
Transsexuals & Crossdressers

I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to...

Sissy Jessica Kinky Office Shagging Ch. 02

by Sissy Adele Howells on Aug 18, 2017
Fetish

Hi again this is Sissy Jessica Howells , the kinky 0lchfa schoolgirl with an excited cock inside her navy, blue panties. At this moment my cock is inside Georgina Harris's mouth. Georgina, my 23 year old ginger girlfriend, has her head between my legs, giving me a fantastic blow job. Just feeling her long, red hair against my balls, gives me a weird sensatio...

Three Old Tarts and a Sissy Ch. 02

by Sissy Adele Howells on Oct 13, 2017
Fetish

We all sat in the living room of Diane Bennett's house. I was proud to be sissy Charlotte Church. My wife to be, Joan Harries sat naked on the sofa next to Sonia White. Joan's body could have done with being ironed over, but for 70 years of age, she had a fantastic figure. Having kinky sex with Joan, two hours earlier was the icing on the cake. For her to ex...

A Sissy's New Daddy Ch. 06

by sissyneko on Sep 25, 2017
Transsexuals & Crossdressers

A loud crack of thunder broke the silence and Billie smiled in his bunk. Lights had been out for almost an hour and he couldn't sleep. The prison had gotten a new influx of prisoners. The first night was always the hardest and it was hard on Billie too, he could never sleep listening to the crying. Plus Billie had gotten a new cellmate in the process, a cell...

The Visitor Ch. 10

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

I don't know how long I slept for, how long my poor battered mind floated in the warm sea of mindless contentment, before I came to. I stretched yawning, my body feeling stiff and strangely aching. All the memories of those things that I'd been subjected to were still a distant dream, until the realisation that I was still dressed in that horrible adult baby...

Pregnant Pause and Free Delivery

by clinton09 on Sep 13, 2017
Erotic Couplings

[©2010 BY CLINTON09; ALL CHARACTERS OVER THE AGE OF 18; NO EVENTS DESCRIBED ARE TRUE; STORIES HAVE A 'HARDER EDGE' THAN MOST; BE WARNED; HERE BE DRAGONS] [Elements of incest are touched upon but are not integral to the story plot.] * "You DO understand me, don't you, I? I am saying that you are a no account bum that will never amount to anything. You cert...