Sissy Stories

6,529 results
Orientation
Length
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Infinite Scroll

Career Fair

by embracelust66 on Sep 15, 2017
Group Sex

Bethany Cooper was feeling old, lonely and depressed. This was partly due to the hundreds of college students milling around her in the atrium of the Prentiss College Student Union. For her, they were a reminder that she had recently turned 36 and that her prime years were well behind her. She felt this way every time she attended one of these career fairs,...

Tara of Vietnam

by RAMJET69 on Sep 14, 2017
Interracial Love

"Oh my god, we're gonna crash!" a woman shrieks. White knuckled passengers tense as the plane's cabin pitches upward then noses down like a diving roller coaster. The woman's screams sound like Faye Ray in King Kong. I've flown a lot but this ancient airliner is rattling like it's held together by loose bolts. A Vietnamese flight steward stumbles down the...

The Devil You Know Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Brian Davies sat on the hard toilet seat in a cubicle of the men's room on the twelfth floor of the building housing the large publishing company he worked for; he was reading the Daily Mail and trying to kill the last half hour before quitting time. As a middle-management employee he didn't really work mandated hours; he was expected to work whatever hours...

The Oval Ball

by CanadianLover on Sep 1, 2017
Group Sex

I and Charlotte, my wife of more than ten years, had moved to a new neighborhood of the Southern French city of Lourdes. Now you may have heard about this city as a famous pilgrimage site. It is what makes us Lourdes citizens relatively wealthy – and in fact, both Charlotte and I work in separate hotels here. But beyond the everyday business of hosting inter...

Do You Believe In Magic?

by griffin57 on Sep 13, 2017
Transsexuals & Crossdressers

This is dedicated to my editor and muse. Love you MJ. ***** "So when are you going to ask Megan out, Mark?" I caught my best friend Danny Tyler smirking out of the corner of my eye. We were headed home from a movie and bantering back and forth as usual. I mentioned that I liked her in passing, but Danny was all over it like a duck on a June bug. "When I...

Bringing Out the Animal

by Daveest on Sep 1, 2017
Group Sex

It had been a busy and very hot day at work for Dave Gleeson; the sweat was running down his back and from under his arms. He smelled like a horse that's was ridden hard and put away wet. All he looked forward to was a cold beer and a dip in the pool. As he entered the drive to his duplex he noticed a moving van, parked in front of his garage. He was immed...

When Darkness Falls

by smhgirl2002 on Sep 17, 2017
Non-Erotic

“See you when you get back from vacation Stephanie,” I said as I took off walking down the sidewalk. It was 9:30 on a beautiful Sunday night. The sky was clear and all the stars were shining brightly. I was quietly humming as I walked home, looking up at the sky often. When I was only a few blocks away from my house, an arm tightly wrapped around my neck. I...

New Neighbours, New Love

by sirhugs on Sep 15, 2017
Group Sex

I had only moved next door four months ago, but in an effort to fit in, I had hosted a get acquainted barbeque. Since the house I had bought came with both a heated full size pool and a hot tub, most of the guests either arrived in swim wear or had run home to change after we ate. The few reluctant ones had joked about how even the hot tub couldn't make them...

The Daddy-Son Dance

by neverless on Feb 26, 2019
Transgender & Crossdressers

Note: This story contains transvestite gay sex between a father and son. Do not read if this offends you. ***** "So what is this place?" I asked as we turned from the road and down a tree lined lane. "It's a surprise," my Dad smiled at me both happily and enigmatically. We were close, me and Dad, I'd not know my Mom, she'd left when I was so small she w...

Just One of the Guys Ch. 05a

by CraptainPlanet on Aug 26, 2019
Exhibitionist & Voyeur

We were all tired when we got back to the house. By that I mean that Rachel, Mike and I were tired. Andrew and Kyle were buzzing with excitement. They’d only received Mike’s pictures from the swimsuit shop as far as I knew. My first thought was to insist that nothing else out of the ordinary happened, but then they saw Rachel, who was clearly still covered i...