Sissy Neighbor Stories

22,255 results
Orientation
Length
Source
Infinite Scroll

Caught In Pink Panties

by NikkiCD on Sep 13, 2017
Transsexuals & Crossdressers

I just got home from work at the local coffee shop; it's around 3 in the afternoon, about the same time I get home every day during the week. I recently graduated from high school and I'm working this job until I decide what I'm going to do next. I live alone with my mom, my father left us when I was 11 years old, and I'm 18 now. My memories of Dad are that...

The Neighbours Situation Ch. 01

by Missclo on Jun 19, 2019
Transgender & Crossdressers

Being my first story, any constructive criticism is very much appreciated! :) A massive thanks to Macktosh for the editing! * It was a standard afternoon in my area, quiet with very little to do and the usual dull weather. Being single and living on my own meant that when I wasn't working, I had a good amount of spare time. Born in a quiet town in England...

Found - Again

by BufordTJusticeTX on Sep 16, 2017
Transsexuals & Crossdressers

This story is a work of fiction, if it has any similarities it's all in your head. It does have graphic descriptions of sex; all participants are above legal age. This is the second story in the set, I encourage you to read part one, Found. I appreciate all feedback. ***** FOUND, AGAIN. Sally finished the evening by telling me to go home and get some res...

The Perfect Age Ch. 06

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

He's up over the top of me, slighty off to my side with his left nipple in my mouth. He has his hand on my penis and strokes me softly as I suck, nibble and kiss him. I can still taste his cum in my mouth. I can taste my rear end too, it was all over his cock when he came in my mouth. After he fucked me for over an hour he finished in my mouth. It's the fi...

A Mistress to Obey Ch. 05

by gbr2004 on Sep 12, 2017
BDSM

Continuation of this story that involves forced fem, forced bi, discipline, humiliation and submission. Not your thing, move on to another story. * We got back to her house and she opened the car door and let me out. I followed her into the house and she went and set down in her chair and I just stood there in front of her. 'Present sissy boy.' I droppe...

My Neighbor Husband is a Jerk Pt. 03

by justme6996 on Dec 24, 2019
Fetish

The following story contains forced bi, pegging and cum eating if those are not your things please look for a different story. As always i would love to read your suggestions, comments and messages. *** I had a lot of trouble falling asleep that night, her words kept on echoing in my head, I was so afraid that she would actually make me suck her husband b...

The New Neighbors (Black Femdom)

by Dunn81 on Aug 12, 2019
BDSM

Hi my name is Julia i'm 42 years old and i'm with my daughter Sofia who's 20. I'm a pretty fit girl who are vegan. I Lost my husband 5 years ago and since that i never dated anyone. I'm a 5'2 brunette with medium size boobs and a medium sized ass too. I weighted around 130 pounds. My Daughter is 5'5 big boobs and small ass. She trained at the gym a lot since...

A Game within a Game Ch. 02D

by doberinca on Sep 16, 2017
Transsexuals & Crossdressers

Author's Note: This is the second story. I still have sometimes trouble to find the right syntax. I hope you still have fun in reading this second story. A third will be following. The characters involved will appear more 'human', not real good and not real bad, and make sometimes bad decisions. Chapter 2D. Another session - or not. The next morning...

A Freshman's Summer Class Ch. 09

by CapnSteelBoy on Jul 6, 2020
Transgender & Crossdressers

**All characters are of legal age for adult content.** We Continue from where we left off with our brave hero, as his adventures at home draw to a summer conclusion! Sorry this may be it for a bit, its very difficult to decide which direction to take this story at now. I mean, can't keep calling it a "Freshman's" anything now that he is a sophomore...I may...

A Panty Boy Confession Ch. 01

by Creativekink on Sep 13, 2017
BDSM

When I moved to Connecticut for a new job, I knew I wouldn't have a lot of friends right away. That was not out of shyness, it was just to be expected with being in a new town. Thankfully my neighbors were very friendly. I was in mid-20s when I moved into the small apartment complex in Danbury. Since it was late in the summer, I made sure to cook outside as...