Sissy Girlfriend Stories

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Savannah's Hypnotic Socks Pt. 21

by Fibaro on Dec 24, 2019
BDSM

Chapter 25 After a few intense nerve wrecking minutes of waiting Roxanne felt a rather pleasant feeling much to her surprise. Someone was rubbing some kind of cream right above her pussy in circular motions. It felt rather pleasant yet at the same time it also felt so wrong and embarrassing. To make it worse she couldn't help herself from moaning around the...

Nick and Sandi Meet for Lunch

by sandifeettv on Dec 3, 2017
Transsexuals & Crossdressers

This happened a few years ago, but I fondly remember the day. I'd been cross-dressing for years and had yet to meet someone that was a dominant type. Mostly I met men that only wanted me to get a room, tell them the number and they would stop by and I'd blow them. I passed on that. I met TV/CD's. This was more fun, as we modeled for each other, but every one...

The Virgin Tranny & the Bride Ch. 07

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Firstly, on behalf of Roberta and myself may I thank you all very much for your very generous votes. We now continue Roberta's story and it is the morning after and tranny Roberta views the video of her big wedding day before a shopping trip and an exciting public photo call. * * * * * Next morning, I was awoken by a very excited John. "Come and see this...

Rebound Sissy

by Sissyhalo1 on Jun 1, 2020
Transgender & Crossdressers

John had broken up with Angie, his girlfriend after what was like three years. They dated their first year of college then they moved in together and were serious for three years. And none of our friend circle saw the break up coming. And we sort of rallied around John as he tried to pick up his life. Which included going out and getting him to go out wit...

Sissy's Decline into a Slut Pt. 02

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...

A Downtown Moment

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the company. While I never went out with Loretta, we did have the od...

The Perfect Age Ch. 03

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

"Hold still!" Felt his hand come down across my rear so hard I saw stars, wanted to cry out, stifled it as best I could. He slapped me again much harder, loud 'crack' as his large hand came down across my bare butt, made my cheeks quiver. I pulled forward but could not get away. He had the index finger and thumb of his left hand in a vice-like circular gri...

Revenge?

by magmaman on Sep 15, 2017
Loving Wives

When a young man is barely 19 years old, hormones rage. It's just the way of life. Ricky was that way, having discovered the joys of sex just a few days earlier. He decided he really did like that. That one time had been in his old Chevy Camaro and it was not all that easy to do. The beach party earlier had been a kick, Ricky spent most of the evening dan...

Steph's Descent Ch. 09

by 62_goo on Aug 31, 2017
Fetish

Steph woke up and looked at the sleeping form next to her. Her first thought was of her husband, Phil. But a split second after that thought entered her head she realised that it was Amanda her girlfriend sleeping next to her. She thought about how much in love with Amanda she was and also of the situation she found herself in. It had started when she was f...

Mistress Emma's Revenge

by sissymissyct on Oct 15, 2017
Fetish

Hi I'm Ken. Well I was, now I'm called Brenda. Here's a bit of my story for you. I hope you don't make the same mistakes I did. Because until I got caught misbehaving by my mistress, life was pretty good. At 38, I had a great job as an office manager in charge of 25 or so employees, mostly women, a really good salary, a nice office and plenty of job securit...