First Time Swap Stories

351,083 results
Orientation
Length
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Infinite Scroll

Who's Who

by TopherLovesLeigh on Mar 2, 2020
Group Sex

This story describes a moment in time (December 1990) and was written shortly after it occurred. The descriptions of the people in the story are accurate for the time however, their names may have been changed to protect the innocent. Understand that like all works "Based on a True Story", there may be some artistic license taken. *************** Shortly...

Quarantined Pt. 04

by Kabba118 on Jun 15, 2020
Group Sex

If you missed parts 1-3 please feel free to read them. Thanks for hanging out with this throuple during the Stay At Home orders. I hope you all are continuing to stay safe and healthy. -KK ~~~~~~ Day 10: I woke up curled in a fetal position. I open my eyes and Peter was in front of me, watching me, waiting for me to wake up. He smiled at me and then I sm...

Don & Lisa Ch. 02

by adamgunn on Sep 14, 2017
Erotic Couplings

Seventy Five! I think 75 is a milestone, don't you? Particularly when my final objective is only 100. I'm three quarters of the way there. On the way to what, you ask? My 100th guy. I designed a stickpin just for the occasion. It's the symbols of the two sexes, interlocked and made out of platinum for, of course, 75. The center of it is a ruby for my red ha...

Two First Times

by litpervgrrl on Sep 12, 2017
First Time

Losing my virginity was the biggest anticlimax ever. I was 19, a freshman in college, and I just itching to get laid. It may sound stupid now, but I hadn't dated much in high school, and I was really afraid that I would die a virgin. I was shy, and I didn't have a very good self-image. Also, I had discovered the joys of penetration early, and I had built up...

Hemingway Beach

by CEFrenchman on Jul 17, 2018
Exhibitionist & Voyeur

I was a young woman when I first came to realize the effect my body had on men. Because I was an ugly duckling and then a late bloomer, I became hyper-aware when men started to notice me and quickly learned to appreciate it. I loved that my looks made them nicer to me and got me special favors and attention. It wasn't until I was old enough to purchase my ow...

Part of The Procedure? Ch. 02

by magmaman on Sep 12, 2017
Mature

Once again, nothing erotic in this tale, not really. My wife is home from school now, thank God. For some reason I just don't feel like writing when I am living all alone for weeks at a time. Perhaps it is because nothing happens? Anyway, just some updates here, lord knows what will come up next. +++ I drove the 150 miles up to Portland in my wife Debra...

Lt. Gordon's Transformation Ch. 06

by DMaster_14 on Sep 12, 2017
Celebrities & Fan Fiction

"Personal Log: Stardate 46128.2. Lt. Jamie Gordon recording. Note: all log entries pertaining to Lt. Jamie Gordon classified under authorization Alpha Omega One Three and voice patterns of Jamie Gordon and James Gordon. "It has been five days since I reported aboard the USS Korvan. The transporter malfunction that transformed me into a transgender individua...

My First Fuck

by Glenalk on Aug 18, 2017
First Time

I was 18 when I first met Ben; he was tall, slim and had extremely boyish looks. He was confident and from what my friends had told me, a bit of a Jack the Lad, whereas I was shy and certainly lacked confidence in myself. We were both in the RAF, he was a driver and I was a clerk. My friend Susan was going out with his best friend Jeff, and she asked me if...

If Not Tracy, Mother Will Do

by alexcarr on Aug 18, 2017
First Time

My name is Jacey Turner and Tracy is my daughter, the result of a very unhappy marriage with a dick-head I'd rather not talk about thank you. But Tracy has been the perfect daughter and we have been that close - but now I have to face up to change because it is likely that, with Tracy having at last found herself a boy friend called Jack, I could soon be lo...

Matt and Brad: Gay Lovers Ch. 07

by SplitLicker69 on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 7 Brad Joins the Party Brad closed up the course and drove to Matt's house. He was looking forward to spending a quite evening with Matt and his lovely mom Katrina. He arrived to find Matt his mom stark naked, sleeping on patio lounge chairs. He walked back to the front door, opened and slammed it shut announcing loudly" "Hey I'm home! " "We're...