Strapon Stories

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Sissy for Mommy's Nipple Cream Ch. 05

by ppeaks42 on Nov 2, 2020
Transgender & Crossdressers

The evening after Jaime's doomed attempt at seducing Julia found the young sissy crying into her pillow as she tried to reconcile herself to the whirlwind of changes she'd gone through. Less than two months ago "Jaime" had been nothing but a shared figment of imagination, a character he dressed as for his regular breastfeedings with his mother. When he'd tri...

Pegging Tales: Justin's First Time

by hfernandez1983 on Sep 13, 2017
Illustrated

*-*-* Pegging has been a topic that I have wanted to write about for a very long time. In my personal life, I have yet to do it. It has long been a fantasy that I felt has been left unfulfilled for a while. I have read a lot of stories on the topic and have loved most of what has been published on Literotica. So I thought it was time maybe I write a story o...

A Birthday Femdom Fantasy Realised

by KinkyAussieDave on Aug 13, 2019
Erotic Couplings

It was my 37th birthday but my first with my new girlfriend/partner. We had been together for just over 6 months. We had enjoyed a pretty enjoyable sex life and were open to trying new things throughout our relationship. She was a few years older than me turning 40 a month later. We had shared some fantasies and engaged in a few firsts within our 6 months to...

My New Life with Her

by humbleslave on Sep 16, 2017
Transsexuals & Crossdressers

(This is a continuation of "My First Session with Her" and incorporates Staci from "Domination Road Trip." I have attempted to make this story stand alone, but it may make more sense if you read the other two stories first to get a background on the characters.) My owner, Ms. Andrea, was finally satisfied with the blow job I'd given her strapon, and relea...

Seeing Stars Pt. 01

by Silverhunter409 on Sep 13, 2017
Celebrities & Fan Fiction

It started like any adventure starts. I was in LA on business, business that I had finished with after one day of my week-long trip. I found myself with nothing to do except spend time on the beach and explore the city. It was my first visit to Los Angeles and I had expected to see celebrities everywhere, but that is just another Hollywood myth since I didn'...

Man Is Humiliated By Escort

by fun4all6969 on Sep 12, 2017
Transsexuals & Crossdressers

I am a very adventurous, open minded married guy. I am 6'2", 150lbs and I have a 5" cock. My wife (Mary) is great but she is very straight laced and doesn't like to have sex but twice a year so I decided to look elsewhere to fulfill a few fantasies. I am sure my size and stamina have a lot to do with my wife's lack of a sex drive. I recently replied to an o...

Fun Down Under Ch. 02

by watchdwag on Aug 30, 2017
Fetish

After catching John and his girlfriend Jayne in a little extracurricular behind his wife's back, I knew I had the old boy in a spot. I'm not really a bloke that would ordinarily take advantage of another man's bad fortune but this fella' seemed to enjoy my having my way with him. There wasn't any doubt in my mind that the chap was "bi" the way he sucked my c...

The Matriarch Ch. 01

by AMurphyWriting on Jan 8, 2019
BDSM

*This chapter deals with much of the administration that new pets at The Matriarch must undergo. As a result, it doesn't contain as much of the good stuff as the introduction did. Rather, it lays more solid groundwork for future chapters.* ***** *When last we left off, our young protagonist had just been hired on as a pet by the notorious Violet, owner of...

The Law of Attraction Ch. 07

by hottchic on Sep 14, 2017
Transsexuals & Crossdressers

This story is a transsexual fantasy. Before reading this chapter I highly recommend that you read chapters 1 to 6. The first four chapters of this tale were told from the prospective of James/Jamie who started out as a shy cross dresser. This is the third chapter to be told by Ashley a hard core lesbian who becomes attracted and eventually falls in love w...

A Young Domme's First

by soledad123 on Sep 17, 2017
BDSM

A hers & his recounting of sex as female Domme and male submissive. Her: I tell him to strip and watch carefully as he exposes himself to me, eyes downcast and demure as he slips off his clothes. I can sense that this overt submissiveness is an act, and my grin widens at the challenge. I want more than anything to watch the act fracture and give away to r...