Crossdressing First Time Stories

351,059 results
Orientation
Length
Source
Infinite Scroll

Fiona

by Erotic Reverie on Sep 13, 2017
Exhibitionist & Voyeur

Fiona I wrote the words in black ink on the white cardboard and slipped the sign behind the curtain onto the windowsill facing her apartment. It read: 9-21-05 5:00pm Apt. No 1630---> The arrow pointed to the bottle of champagne placed next to the message. I knew she would see it well in advance of the date. I did not ask for an RSVP, intending to wait u...

Just One Night, The Aftermath Ch. 02

by maxfly on Sep 14, 2017
Loving Wives

I woke early, as usual, and lay there thinking for a long time about everything that had happened the day before, our first in Cancun. On one hand, it had not been as bad as I thought it would be. I can honestly say I enjoyed having sex another woman for the first time in over ten years. The way it had all played out left me feeling confident and at peace wi...

My Loving Family Ch. 14

by sealawyer on Sep 13, 2017
Novels and Novellas

Synopsis: The card players grow tired of bridge and play a torrid hand of strip poker, which leads to Peter and Sarah's first swing. Part III -- Our Story Chapter Fourteen Our relationship with the O'Conner's -- and my relationship with Sarah -- was changed forever. Now, our bridge games almost always ended early, usually when one of us suggested a trip d...

Chances Ch. 02

by Mistermister on Sep 13, 2017
Novels and Novellas

Cindy and I had developed a routine whereby every Saturday morning we went for a walk in a nearby park just the two of us. Christy usually took this time to go to the gym and usually Vicky would join her. Cindy loved this time she loved picking wild flowers for Christy and chasing butterflies. On Sunday afternoons, we would hang out in the backyard where I h...

Mary Smith, Escort Extraordinaire

by AAAtheist on Sep 17, 2018
Humor & Satire

I am an honest-to-goodness, flesh-and-blood, mostly friendly, often frisky, black adult American female person woman human. I am that no matter what I choose to do and no matter what someone else chooses to do with me. I am also a proud, ethical, and unabashed sex worker. My client rules of engagement are as follows. No piss, race, poop, rape, incest, slav...

Sandi's Erotic Adventures Ch. 24

by Scribe10Redact on Jun 19, 2018
Novels and Novellas

A semi-autobiographical account of my sexual encounters over many years. Chapter Twenty-Four. 2004. (May.) Mike W, mid-forties. It was an unusually hot weekend for mid-May and on the Sunday afternoon hubby suggested driving over to B. Country Park. Sounded good to me so off we went. Parking the car we set out on one of the main paths but had only been...

Tracy's Visit

by julesteve on Sep 13, 2017
Erotic Couplings

Continued from a previous story entitled; Meeting Tracy. * Travelling back from the bar Tracy sat in the back of the Taxi with me, Steve in the front chatting to the driver. Neither Tracy nor I had replaced our bras; our nipples were clearly visible so every now and again I would catch the Taxi driver copping an eyeful in his rear view mirror. Nudging Tr...

The Whore and Me

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

Pro I was at an adult theater watching a guy share his lady with others. She had a cock in each hand and a mouth on each tit. Her guy handed a man a condom and he was soon fucking her. She appeared to be in the middle of a feeding frenzy. After the guy fucking her was done another condom was handed out and she was fucked again. Her body was covered with cum...

Casey Blossoms

by jackie_em on Feb 7, 2018
Transsexuals & Crossdressers

As I grew up, I knew I wasn't a guy – not a normal guy anyhow. The normal boys liked doing rough things, fighting, playing war, playing sports, watching sports, hunting, fishing, all those male things. I didn't like any of that. On the other hand, I never wanted to be thought of as a sissy. I went through some of that, so I hung out with the boys and did jus...

The Wine Tasting

by pbon44 on Sep 13, 2017
Erotic Couplings

It was summer and oppressively hot. A job landed in Craig's, lap; he received a request for a focus group to taste wine. Craig a marketing consultant gets jobs like this all the time. He remembered a friend that has house in the hills that he rented before and thought that it would be a good place for his tasting session. While not running away from disease,...