Sissy Boy Post Orgasm Stories

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Simon Sissy Slave Ch. 02

by Timewarp10 on Jul 30, 2019
BDSM

Simon's arse remained sore for days, a constant reminder of his new role in life. Over the weekend the pain was severe, but the overwhelming feeling of his humiliation was compensation enough, and produced a warm glow through his body. His mind had been in turmoil all week-end. Sometimes the pain was unbearable, but he bought a cream at the pharmacy that rel...

Submitting to the Neighbour Lady

by Stillherer on Jun 8, 2020
BDSM

I went to high school with the Post twins in the late 60's. Tommy and Belinda Post. The Post twins were new to our area and it was rumoured that their father wasn't with them. It was our senior year and being 18 we just wanted it over with so we could get on with being adults. Belinda never gave me a second look but before he knew better Tommy struck up a te...

Snap! to it Divina

by DivinaTellsAll on Feb 12, 2019
BDSM

Writer's note: The following story is 100% true THE DRIVE The drive to Austin was 8 hours in good weather. Today it had been raining, and it was going to be 11 hours in the car, by arrival time. I was acutely aware of how long the car ride had been so far, for several reasons. The biggest of which was the overly-tight pair of pink sissy panties, curren...

Using Her sub

by aSub2fems on Sep 13, 2017
Fetish

Early one September morning I awoke to find a strange letter laying on the pillow next to me. It appeared that Nikki, my girlfriend, had already gotten ready and left for the day. Assuming that it was just an "I love you" note, I went into the bathroom to begin my own day. When I arrived in the upstairs bathroom I found a pair of black satin fullback panties...

Humiliated Sissy Husband Ch. 02

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Max was very busy hand washing all of Tonya's underwear and lingerie in the kitchen sink. He dipped a pair of her panties in the clean rinse water dunking them several times before twisting them and squeezing out the excess water. He then placed them in the clothes basket on the counter. Tonya insisted he wear 6" heels around the house especially when doing...

Simon Sissy Slave Ch. 01

by Timewarp10 on Jul 30, 2019
BDSM

It was late summer in 1964, and it was Simon's first day at his new job. Simon had read his letter of appointment several times; and he held it in his hand now, standing anxiously outside the imperiously heavy door, embossed with "Post Room" in faded gold lettering. The door was probably victorian, Simon judged, and perhaps it had been a post room for many d...

The Dominatrix Order Pt. 04 Ch. 03 - Femdom

by Jwwsmith on Apr 23, 2019
Fetish

Sixteen days before the next supply of Medication 42 was due to be manufactured, General Callisto paid another visit to Femininus. Upon the General's arrival, she was nonplussed when she received an invitation to have drinks with Isabella at her castle. She arrived at Isabella's residence that morning, dressed in a modest black knee length dress. Servant Bul...

Thank You Miss 'Nessa

by Cleverlicious01 on Sep 13, 2017
BDSM

Of one thing, Vanessa was most certain: She savored the feeling of taking a typically, naturally dominant man, and turning him into a servile sissy. By chance, Mike already happened to have the secret calling encased in his DNA. His alpha male appearance, with lean muscular physique and beaconing hazel eyes, would have made any other woman weak in the knee...

A Sissy's Forced Gangbang Pt. 01

by sissy77 on Dec 3, 2017
Transsexuals & Crossdressers

I have always seen myself more feminine than most guys I grew up with. Slim and hairless throughout my body, more curvy than muscular. Until my early teens (I am 25 now BTW), being a sissy for me meant not being masculine as other guys both physically and mentally. When i reached my early twenties it turned to me brainwashing myself through sissy hypo vide...

Jasmine Fucks My Wife

by cuntenslaver on Sep 12, 2017
Transsexuals & Crossdressers

Hello, my name is Tim. I am a 30 year-old married man. I have been married for five years to my wife Danielle. She is an absolute beauty of a woman. I remember when we were married, I felt like I was the luckiest man in the world. Since I am no hunk myself, standing at just five foot six and extremely lanky, I felt like I didn't deserve such a nice, gorgeous...