Sissy Halloween Stories

12,071 results
Orientation
Length
Source
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Halloween Pool Party Pt. 03

by sissymissyct on Sep 15, 2017
Fetish

I soon headed to town and told the apt manager that I was sorry but I would have to move out immediately. It was a family emergency and I would be leaving the area the next day. I asked if he knew anyone that would purchase my furniture, appliances and household stuff, and he asked to see it. It was all quality furniture and he said he would take it and offe...

Happy Marriage

by yesplease8 on Sep 25, 2017
Group Sex

Over the years of our marriage, my wife and I have been very open sexually with each other. After 15 years of wedded bliss, my sexy wife and I have come to a mutually satisfying understanding. I am sexually submissive and bi-curious, while my wife is sexually dominant and loves to humiliate me like I so desire. In the last few years, we've really enjoyed mo...

Halloween Sissy

by Jst439 on Dec 1, 2020
Transsexual

You take a step forward and pick up the dress and immediately realize that you’re going to have to try it on. But first you decide to pick out the perfect pair of panties. You run to her drawer and find a pair of black satin thong panties. After stripping down you quickly pull them on, enjoying the sensation of the satin sliding up your legs before tucking y...

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Truth or Dare Sissy

by maxy007 on Sep 12, 2017
Transsexuals & Crossdressers

It was your usual high school gath. At the time I was just an innocent 18 year old enjoying life with some friends. My name is max, and this is the story of how a small 20 person gathering turned me into a sissy. It was mid-year of the final year of high school, and my friend Isabel was holding a gath on Saturday night. It was a welcome break from study, a...

Panty Posers Ch. 06

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

We entered our building and bumped into our downstairs neighbor Jerry. He was taking his trashcan back to his apartment. He set it down at the landing and gave us each a good look. He wasn't at all phased by our appearances. "Little early for Halloween, isn't it...boys?" he asked. We both were fully aware Jerry knew we were sissies. It was fairly obvious...

Panty Posers Ch. 05

by EROTICbearscribe on Oct 5, 2020
Transgender & Crossdressers

I certainly wasn't in Kansas. I was dressed as a private school girl tease and standing in front of an adult bookstore superstore. What did my sissy sister have in mind? I tried to find some sort of hint but his poker face offered no clues. We were certainly dressed for more than just shopping for DVD's. So I didn't think we were there for the sales. We ha...

Tell Me what You were Thinking

by trixie_leigh on Oct 12, 2017
Fetish

I'm on my knees. It's Halloween. We're at a party. I'm dressed like a slut. Which, I guess I am, since I'm on my knees. Giving blowjobs. It was only supposed to be one. You said a friend of yours from work would help me live out my fantasy. Really, your fantasy for me. My fantasy is much simpler. You let me dress in panties and sleep in lingerie. And let me...

Sissy Bitch Ch. 01

by sissy_memories on Sep 12, 2017
Transsexuals & Crossdressers

After I moved out of my parent's house, I found an apartment with my a girl called Laura. I was nineteen, she was eighteen and, as one of the few left in town after everyone we knew took off for college, we had little choice for room mates. I didn't even know Laura that well: we had mutual friends and that was about it (though I did know she was good fun aft...

Happy Marriage Ch. 02

by yesplease8 on Sep 25, 2017
Loving Wives

Well, our marriage just keeps getting better. My wife and I love that I'm submissive and that I was bi-curious. I say I was bi-curious, because my wife set me up to realize I am truly bisexual. After begging her to use me like a sissy slut with a strap on, she not only treated me like a slut with her strap on, she happily watched me with another man. She se...

Halloween Pool Party Pt. 05

by sissymissyct on Sep 14, 2017
Fetish

We arrived home and Annie greeted us warmly, then stepped back to get a good look at me from head to toe, having me turn to see the full look. Satisfied with what she saw, I was told to bring in my clothes, put them away and then pick something pretty to wear as dinner would be ready shortly. Miss Maddy and Annie headed into the main house and I went about m...