Shemale First Time Stories

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The House of Lights Ch. 05

by Pgup on Sep 16, 2017
Sci-Fi & Fantasy

I was nervously pacing up and down in my little room and all the time I was thinking, "For heaven's sake, shape up Abigail. This is not the first dance you have ever attended so get a grip on yourself." "Yeah, but it is the first one that I ever went to without a stitch of clothing to cover my nakedness! And, it is the very first one that I ever went to whe...

Against All Odds Ch. 02

by RandyHlms on Jul 31, 2019
Loving Wives

I woke up in a blissful fog that Saturday morning. Had it all really happened? After 25 years of self doubt and loneliness had I really just bedded the most spectacular woman I would likely ever meet? Even decades later it still seems like a perfect moment frozen in time. Terri was the ideal woman to lose my virginity with. Patient, caring, spectacular in...

My New Career - Diane

by Otazel on Feb 12, 2019
Mature

My accidental career as a gigolo began only recently and my very first customer was an elderly neighbour, Mary Shaw. I was penniless at the time due to the combination of a lost job and a broken marriage, and so I was only too eager to take up what might normally have been an unlikely occupation. I had initially intended it to be a one off with Mary, just to...

Taking Bunty in the Kitchen

by ur_firman on Sep 25, 2017
Loving Wives

I had popped in to see how Bunty was, knocking on her door she appeared Bunty was an elegant, tall, sexy brunette woman, with an hourglass figure and a face men pay to look at. Wearing a grey knee length skirt showing off her slim legs and matching rollover woollen-necked jumper, which you could clearly see the shape of her bra beneath. As normal moments l...

Stein's Girl Ch. 06

by Orfeo on Sep 16, 2017
Erotic Horror

[AUTHORS NOTE: This is the conclusion of a series and will thus make a whole lot more sense and, I hope, be more rewarding, if you read the first five parts before reading this final entry] Stein's Girl: 6 - Quietus Samuel stumbled into the room, still holding up his pants. Angelique followed right behind and she did not give him much time to collect his t...

Teasing Til It Hurts

by Jizaz_Jester on Sep 25, 2017
First Time

More than two years before I'd met Natalia through a mutual friend, and after nearly six months of almost intolerable teasing I finally got her to go out with me. That wasn't easy to go through either; it was our fourth date before she even kissed me, and that was on the cheek. More than a few times over the course of the courtship that I considered giving...

The Pirate King Ch. 13

by nakamook on Sep 14, 2017
Sci-Fi & Fantasy

This is part of an ongoing series - if you find yourself here without reading the rest, I highly recommend you go back and read the rest of the series. We'll still be here when you get back:) Alternate title: long live the fucking king Short chapter this week, just needed to collect the kids and get them on the road. A bit more lore, a bit more world build...

Bike Ride Ch. 03

by Justtoold on Sep 17, 2017
Loving Wives

This is the third chapter of three stories that are related. It continues on from where the first two stories ended. The idea for this story happened when a friend of mine bought a Harley trike from a guy, and my wife thought it was a neat machine. From there my warped mind took over and here we are. This story is like the rest of my stories in that I do no...

Costume Drama Ch. 05-06

by TonyDowse on Sep 14, 2017
Erotic Couplings

Chapter 5 As I have often found final performances are, ours went absolutely brilliantly - not only were there no technical glitches but everyone was in high spirits and so gave of their very maximum - and the audience's response was even more enthusiastic, bringing us all back for repeated curtain calls. Greg and I had previously agreed that as we would l...

Anal Anywhere, Anytime Ch. 02

by walterio on Jan 22, 2020
Anal

BEFORE CHARLOTTE As long as Walt could remember he had been drawn to a shapely female bottom. I didn't have sex until I was 18 but I had hundreds of boners from just looking at the outline of curvy buttocks contained in skirts and slacks. I found myself watching TV hoping to get a look at an actress's derriere. Even during commercials, I checked out a curvy...