Crossdresser First Time Stories

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Hot Couplings: Cumming in Olympia

by LYMYCWTKYB on Aug 30, 2017
Erotic Couplings

Another true story. Comments and story suggestions welcomed... --------------------------------- Jake and Traci were back on again, this time after a disconnect of a week. Apart from whatever was said or done, they always came back to that essential truth: they were crazy about each other and couldn't bear to be apart....especially when his hard cock and h...

New Toy Ch. 01

by DeSadesDisciple on Sep 16, 2017
BDSM

I was so nervous sat there waiting for her. We had been in contact for 5 years now and had 'spoke to' each other, whether by chatroom, Instant Messenger, Text Message or Telephone, every day of those 5 years, but this was the first time we were going to meet in person. First meeting in a fetish chatroom when she was a bored, unfulfilled housewife with 2 kid...

Voyeuring a MILF

by Irish Moss on Sep 14, 2017
Exhibitionist & Voyeur

Jen’s mom was even hotter from five feet away, on the same side of the window, and peeling off her clothes. I was sitting naked in an armchair in her living room, my rigid cock protruding from my lap like a rocket ready to blast off, just watching her. This time she knew I was watching and was doing a little striptease just for me. She peeled off her white b...

Enterprising College Sluts Ch. 02

by FantasyRed on Sep 13, 2017
Erotic Couplings

Coming up with a good activity for my next session with M. Stewart was a challenge. Not because I couldn't think of anything, but because I couldn't decide what I wanted to do next. I'd already flashed him my tits and given him a lengthy showing of my tight, auburn-haired pussy. I'd even climaxed unexpectedly as I rubbed up against his desk, my ass in full v...

An Unexpected Gift

by Ninegoodreasons on Sep 13, 2017
Erotic Couplings

Most everything about my life could be classed as normal. I have a boring low paid job and the only minor exception to my normalcy is that I live with my sister, not being able to afford a place of my own. Life was looking bleak at home with my parents and things started to fall apart. Fortunately my sister offered me a room in her house at a dirt cheap pric...

Even Exchange

by endgambit on Aug 18, 2017
First Time

I was 18 years old when it happened. My first handjob. I was an A student and pretty much kept to myself. I had a few friends. But mostly all we did together was hang out and play video games. This did not exactly bring in the girls. I had made a few aborted attempts to ask girls out in High School. But I was incredibly shy and frankly, afraid that I would...

And I Have No Name

by JakeJoyce on Sep 14, 2017
Loving Wives

Her name is Miranda, and she is one to be adored. She is 5 foot 1, thin, has the most beautiful red hair I have ever seen, and the cutest face that is speckled with freckles. No one could possibly resist her. Her breasts are the first asset on her that you notice. They are a B cup and incredibly perky. Her nipples are a magnificent shade of pink, they always...

Futanari Breeding Agency Ch. 03

by Sonatatre on May 7, 2019
Transgender & Crossdressers

"Suspended? What do you mean I'm suspended?" Alina said. "I don't have much of a choice. Heck, I think I'm being nice not reporting you two to the police. You got her pregnant for god's sake," Principal Pulcher said. "But I've never been suspended before," Alina tried, knowing it wouldn't work. "My parents are going to freak out," she added, mostly to hers...

Trouble at the Farm Pt. 02

by SeekerOfHerself on Sep 12, 2017
NonHuman

I. She kept her promises, I'll give her that. Amanda and I had snuck off to the barn one day and we didn't expect this little surprise. It was a cool summer's day. Amanda had a half-day finish and she knew I'd be waiting there for her. I had started to really enjoy making love here. I came to associate this place with the countless times I had waited for...

Sister's New Interview

by Ideas64 on Sep 14, 2017
Erotic Couplings

This is the third instalment in the ongoing adventures of Anne-Marie, who, at the time of this adventure was 19, a trainee physiotherapist living alone in her family home in an English Midlands city. Her parents and older brother had all left within the last month to work on the continent. There is no incest in this episode, but, as recorded in the "Siblin...