Shemale First Time Stories

351,086 results
Orientation
Length
Source
Infinite Scroll

Petra the Lesbian Virgin

by MTL17 on May 16, 2018
Celebrities & Fan Fiction

Disclaimer: I do not own Jane The Virgin. I do not make any money from the writing of this story. This story takes place after Episode 15 of Series 3 of Jane The Virgin, a.k.a. after the time jump. **** Petra Solano was not in love with Jane Gloriana Villanueva! She wasn't! Because that would be weird, and awkward, and totally in character for her. Petra...

Great Sex and Nothing More

by Dinsmore on Sep 13, 2017
Romance

If you do not enjoy reading about successful, financially secure, accomplished and attractive people falling in love, fucking freely and living happily ever after, please do not read this story. In spite of the caveat, if you read it and feel compelled to leave a nonsensical, left wing, socialist rant about my lack of humanity or my lack of concern for the p...

Assumptions

by 62_goo on Sep 19, 2017
Loving Wives

A man assumes a number of things when he gets married. I am no different in that regard. I assumed that my wife loved me and only me. Wrong assumption number one. When our vows said, "To death do us part," I assumed that my wife believed that wholeheartedly. Wrong assumption number two. I assumed that when we said that our wedding rings signified our unen...

Work Related Ch. 02

by patricia51 on Sep 14, 2017
Erotic Couplings

Work Related 2 - Date With My Ex I woke from the nicest dream I could remember in a long time. Someone had been giving my pussy the most delicious tongue-lashing I had receieved in a long time. I kept my eyes closed as I could still feel the effects of it. Peter, my ex-husband, and I had our problems during our marriage, but his ability to go down on me was...

Everything for the Career Ch. 01

by HeavyHeartLaments on Sep 13, 2017
Loving Wives

(This part of the story does not contain any sex. If you are waiting for sex, wait till the third part comes out. This is a story of a strong career-oriented woman, who gives up everything, including her sense of responsibility to her husband, her duty towards her family and the security of her future to promote her own career. When she sees her mistake, s...

He Saved My Ass

by claw54 on Sep 17, 2017
BDSM

Chapter 1 It was March 1st, 2001 when I met the man I have committed my heart and body to. That day was cold and rainy. With my hood over my head, I did not see the car that almost hit me. Yes, it was stupid of me, not looking both ways. I didn't hear anything coming, so I took a chance. It's a good thing he was there. I took two steps and then I was looki...

First Time

by fahad on Sep 2, 2017
First Time

Shazia and I had known each other almost literally forever. Her family moved into our neighborhood when I was three. She was two months older than me and a serious tomboy. We played together almost every day and it didn't bother me that she was better at most things than I was. We slept together in the same bed frequently. We wore pajamas and it was non-sexu...

Twins

by jax on Sep 14, 2017
Erotic Couplings

My brother and I are twins, not identical, he's tall and dark whist I am tall and fair. Ever since out mid teens we have been active on the girlfriend front. But we have this one rule, 'No poaching Girlfriends' otherwise all things are fair. I have dated old girlfriends of his and he has done likewise. His current girl, Sue-Ann, is a curvaceous redhead who g...

A Dream Cum True Ch. 01

by skibum334 on Sep 14, 2017
Erotic Couplings

Alyssa pressed her tits together as I squeezed my dick between them and she kept urging me in a low sensuous voice, "Cum on me, Nick, cum all over my tits. Give me a nice thick rope in my mouth and let me taste your salty goodness." The combination of her dirty mouth and firm tight breasts pushed together pleasuring my cock finally did the trick and I sta...

Third Party

by pandsal on Sep 13, 2017
Group Sex

We took a long time - several months - before choosing. The decision was important because we are not an irresponsible young couple playing the field. We are both nearer fifty than forty, in the third decade of our marriage, still very much in love but wise enough to recognise that sex, though pleasurable, was fast becoming routine. Before we got together we...