Sissy Pills Stories

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Ian's New Job Ch. 02

by SatinSlip on Dec 10, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex, crossdressing, and humiliation. ********** Wendy wore the shortest skirt she owned. A blue, pleated thing that stopped a few inches short of her knees. Underneath she wore red lace panties Ian had bought her for valentines a couple years ago, an...

I"M Not, Really, I'm Not

by gbr2004 on Sep 14, 2020
Fetish

I'm finally getting settled in my new place. I have just moved to LA from Kansas a couple weeks ago and had been set up in an apartment by the sales office at the advertising agent who had hired me right out of college. I was so excited to be in a real city and it was so much different from the rural area I had grown up in. College had been fun and I had don...

Amazon Sissy Jock

by Sissyhalo on Mar 21, 2018
Transsexuals & Crossdressers

All parties involved are over 18 years of age. *** It started me going to a party. Now that's not unusual because I'm popular, I've always been popular like ever since junior high. I shot up like a weed getting tall and my dad worked me out while I was going through my growth spurts and had me in lots of stuff like to round me out before I got into footba...

Erotic Journey in Tunisia Ch. 02

by dan57 on Sep 19, 2017
Loving Wives

The third day of the holidays in Tunisia for Kira and her friends was centered by common decision a visit to the city of Tunis itself. Dan showed them the Bardo museum which seemed to interest particularly Kyrhan. The girls were wearing long kaftans (embroidered djellabas) but Dan and Kyrhan had forbidden them to wear any undies underneath. The weather was...

Dominating Ken Pt. 09-10

by oneguy4fun on Sep 26, 2017
BDSM

PART 9: THE POWER OF THREE Kimmee's (Ken's) heels clicked across the marble floor of the hotel lobby. He was in a hurry to go nowhere. He figured if he walked fast enough no one would notice the secret underneath the feminine facade. Mistress Kareena had done such a fabulous job at hiding his masculinity and highlighting his feminine qualities that someone...

Brick

by coldsteel on Sep 12, 2017
Erotic Couplings

Tuesday morning, Operating Room 9. The red-grey tumor stubbornly clung to the sides of the pelvis. For three hours, the two surgeons worked to coax it out. "I've got the view," said Brick. "Two Kelly clamps, scissors and a stick-tie." The instruments danced in her fingers. In seconds, the tumor was out and Brick was throwing one-handed knots deep inside...

Waking Holly

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It's been about a month since I told Holt, Holly the truth and moved her into my house. I never expected the side effects of what I did to her to be her to be her becoming a whole other person. I know it sounded like that's the point but the point is that you changed them, bent them, broke them and made them worse. And I fucking hated Holt, I really fuckin...

Jesse's Journey Down a Rabbit Hole Ch. 14

by sadkins116 on Sep 14, 2017
Illustrated

I want to thank everyone for reading, voting and commenting on our story. I submitted the first six chapters, and Rebeccasm submitted chapter 6 through 12. I will be submitting chapters 12 through 18. We have both worked hard on this series and as such both deserve to share the postings. Hopefully you will visit both of us and enjoy the series. As I mention...

Girlyboy

by Dennis_St_John on Sep 19, 2017
Transsexuals & Crossdressers

Sitting there looking at myself in the mirror while I touched up my makeup, I wondered what I'd become. The reflection gazing back at me with emerald green eyes was that of fresh faced young woman, 22 years old, dark blond, wavy shoulder length hair, a wide mouth with full pouty red lips, a strong chin and high forehead. A very good-looking young female, som...

In Need of Counselling

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

I knew my wife, Becky was unhappy just before Christmas. We had been married for five years and she seemed dissatisfied with everything. We had been incredibly unlucky. I'd been made redundant, we seemed incapable of having children and I had lost interest in sex. I refused to accept that there was anything wrong with our relationship yet she insisted we saw...