Sissy Neighbor Stories

22,255 results
Orientation
Length
Source
Infinite Scroll

Touched By Magic

by HighGrove on Jan 19, 2020
Fantasy

Throughout history, man has been driven by two primal goals: Getting Something for Nothing and Having Sex with Everything. Every great advancement in human civilization, from fire to philosophy to the electric guitar, can be understood as some combination of trying to fleece or fuck one's fellow man. And no single pursuit has more perfectly encapsulated the...

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New Gurl in Town Pt. 02

by GavinIsaNuisance on Oct 5, 2020
Transgender & Crossdressers

This story and its contents is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual manner are 18 and up. Andy begins his sissy adventures as Bianca, but will he be able to woo his crush Riley, or will he be forced to be Carol's bitch forever? We...

Journey into Feminization Ch. 01

by KneelingNancy on Jul 14, 2020
BDSM

***Chapter 01 - The Beginning Like so many of our beginnings, mine started to what some would call a normal life. I grew up in on the west coast and would consider my family upper class. Both my parents had successful careers and my brother and I had a lot of great experiences growing up (private sports clubs, investment in the arts, etc.). During my chil...

Mommy Adriana Makes Greta Become...

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, it took me a while because reality caught up with me, but now the next chapter is ready. I simply hope you don't get bored and enjoy also the 6th installment of my little story. * Finally I lay in bed. I heard Mommy Adriana was sound asleep while I tossed and turned. I simply couldn't sleep after today's events. I would never be the same man...

Shame Game Ch. 04: Jim is Used

by shamefever on Aug 29, 2017
Group Sex

Since Bill had just came to understand his true bisexuality, I told him to go sit on the couch while I grabbed a pair of my sexiest satin panties from the bedroom. When I returned, I threw them in his face and growled, "Put your girly panties on, cum whore." I opened the living room curtains fully and then stood next to our end table lamp. Standing sideways...

Fred Submits Further

by 0ra1Master on Sep 17, 2017
BDSM

It has been more than a few Saturdays since "Fred" went shopping with Mary Pat. If you haven't read the first three "stories" about how "Fred" became my cock sucker you might understand this one a little better if you do; but if you don't that won't matter too much! After all, reading about a formerly straight married man who learns to love being a sissy coc...

Sissy Hubby Ch. 03

by buttboi on Sep 19, 2017
Transsexuals & Crossdressers

As the sleepy fog cleared my mind, I felt warm sunshine on my face. Remembering the night before, I couldn’t help but smile as I pictured my wife Stacy fucking my ass with my pink dildo. Running my hands down my slim body I felt the baby doll nightie still spread across my chest. Finding the strength to sit up and greet the day, I found I was unable to open...

A Mistress to Obey Ch. 03

by gbr2004 on Sep 12, 2017
BDSM

I woke up when she whipped the cover off the cage. I had been able to curl up enough to sleep on my side but when I tried to move I was very stiff. She opened the cage door and I backed out. She told me to go take a nice long shower and that my clothes would be on the bed when I finish. She was wearing a pair of tan slacks and a yellow blouse and looked like...

Brianna Meets Mommy

by Sissy_Sammi_ on Jan 7, 2018
Transsexuals & Crossdressers

*Disclosure, all characters are 18+ years of age Brian had another distracted day of school. Dreading each minute of each class, desperately waiting for the day to end so that he could get home. During his breaks he would text Rick, asking about his wife and what Brianna should wear. Once the final bell rang, Brian ran home as fast as he could. He didn't ca...

Neighbors Sissy Son

by newfield1981 on Sep 18, 2017
Transsexuals & Crossdressers

About two months ago a woman and her son moved into the vacant apartment next to mine. I noticed right away how effeminate the son was, even though he was dressed like any other 18yr old boy, he couldn't have weighed more than 115lbs and his facial features were soft and delicate! Having a thing for femboys (twinks) I set my sights on this one! Since I wor...