Shemale Cum Filled Condom Gloryhole Stories

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Connie at an Adult Bookstore Ch. 01

by cmorehead on Sep 13, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * Let me start by introducing myself. My name is Connie and I am a 40-something tr...

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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Cum-mania at the Gloryhole

by jptune on Sep 13, 2017
Fetish

Well, I guess I just can't resist my girl friends imagination. She comes up with these ideas that wind up driving both of us nuts. She keeps thinking of different ways for the both of us to load our mouths with cum. Last time she got filled with cum in all her holes and I posted the experience in the story named "fill er up". This time it was the gloryhole....

Her

by St_eve on Sep 16, 2017
Fetish

I could never say no to Her, I was helpless, if She said frog, I jumped. She called me into the bedroom; She was on the bed naked, lying on Her side, ass out towards the edge. She told me to take off my clothes and play with myself. I started slowly, looking at Her bare backside, the side of Her breast, Her long dark hair and finally at Her ass. She could se...

First Time Buttslut

by missyminx on Sep 12, 2017
Transsexuals & Crossdressers

I just got home from the adult bookstore, let me tell you what happened to me. Arriving at the abs I went inside and purchased a debit card from the clerk and went into the arcade. Inside the arcade there are eleven booths, two are side by side, I saw that one was occupied so I entered the one beside it took my pants off and sat there in my pink panties stro...

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

Gloryhole First Timer

by SluttyChrissy on Oct 5, 2020
Transgender & Crossdressers

This is a true story of an experience I had a few years back. I hope you enjoy! It all started on a random Thursday on my lunch hour. I was feeling especially girly that day and I decided to make a detour to my favorite little adult bookstore/lingerie store. I walked in and slowly browsed around, looking at the lingerie and dresses, just enjoying the feel...

Adult Shop

by LucyFrance11 on May 7, 2019
Transgender & Crossdressers

As you will have noticed from my previous stories, I am gay. But for the last 20 years I have also been crossdressing and I now spend over half my time dressed. Over the years I have become more adventurous and now regularly dress in public. I live in the South of France not far from Cap D'Agde which during the summer is the sex capital of Europe. There is p...

Journey to Trans Submission Ch. 01

by bluev on Jul 15, 2020
Transgender & Crossdressers

It has been at least thirteen years since I first discovered my kink and one year since I started to think about making it come true. This is a kink I have not shared a word with anyone for a fear of being judged and a fear of being told that it was not right to indulge in such objectification. Finally I came to the point where I said "screw the world, it's...

Purgy's Birthday Blowout Ch. 01

by rikkusguardian on Sep 13, 2017
NonHuman

Purgy is the (c) of :iconmatthewbrandon: Vipra reference is the (c) of :iconVipra: Story is (c) :iconrikkusguardian: This story contains one of my new found love of condom filling/popping! X3 I always wanted to read/see more condom inflation, but there isn't much here, at least not at the levels i like it....so i decided to add it to this story and leave...