Crossdresser First Time Stories

351,031 results
Orientation
Length
Source
Infinite Scroll

Guys Next Door Ch. 01

by flyingfish33 on Oct 3, 2017
Loving Wives

Chapter 1 - It begins This is a story about the start of your wife's promiscuous ways, and when you first learned to enjoy the benefits of an open marriage. You and your wife (Beth) live in a standard suburban area, with nicely mown lawns, lots of parks, and neighbors that still talk to each other. In your particular street, there is one rental property t...

Weekend of Love Pt. 07

by IcelandSpar on Sep 19, 2017
Transsexuals & Crossdressers

(continued from the first six parts) Leland and Helda leant over the edge of the Jacuzzi, and I guided Martha in this act of wonderful exploration. I had got a bag with a few items I thought we'd need, and I opened this and placed a jar of oil on the ledge between us. "First," I said, "let's slick em up nicely." I dipped both hands in, and smacked his...

Alien Experiments Ch. 02

by evanescent82 on Sep 19, 2017
Transsexuals & Crossdressers

The weekend was finally over and Gregg had managed to drag himself to the office somehow. He was there, at his desk, staring at the pile of business reports he had to process but his mind was not on them... Between his legs, his cunt felt sore, almost painfully so. Jose had spent most of that first day in bed with him and then had come for more on Sunday. Th...

Tuition Teacher Fucked by Student

by anilsahotra on Sep 12, 2017
Erotic Couplings

Hi, I'm Anil from Delhi. This was the another sexual experience I had when I was studying in 12th standard. I was always poor in the subject of geography, so my mother asked the lady next door to give me special tuitions for it. Her name is Ekta. She is an old family friend of ours. She is an extremely sober natured lady with a very sweet face and milky whit...

A Different Kind Of Tutor

by sunandsteel on Aug 18, 2017
First Time

Growing up in a small farming town in the early 90's is not what anyone would call exciting. Most times, it was about as fun as watching paint dry. Weekends could be fun, if you liked to go out and drink, or if you had a girlfriend. I had no girlfriend, did not like to party, and was not a typical small town farm boy. Needless to say I had a lot of free time...

Dianne in Panties

by eliasroticatwo on Sep 12, 2017
Fetish

If you're lucky, every once in awhile you fall for someone. Sometimes its love, sometimes its lust but its usually some sort of mixture. I was more than lucky when I first met a woman named Dianne B. Dianne was working at the company I'd just joined. She was assigned to mentor me and we got along well. I was pleased to have made a new friend, one I continue...

A Walk to The Paradise Garden

by sack on Sep 12, 2017
Romance

Note: The title is shared by a wonderful piece of classical music by Frederic Delius. If you can acquire a recording, you will find this story mirrors the music, and with a little luck, when the music stops, the tale will be near the end. This story is dedicated to the exquisite Honey123, her contributions to Literotica are priceless, and I will always cove...

Inventory

by Devil Woman on Sep 12, 2017
Erotic Couplings

As she sat in the car waiting she still couldn't believe that she was actually going to go through with this. Of all the places for her company to send her to inventory, why did it have to be an adult bookstore. At least it was during the store's downtime so she didn't have to contend with the "regulars". Still shaking her head and laughing she saw the oth...

Time For Dinner

by hafnium10 on Sep 13, 2017
Erotic Couplings

We were anxious to get to dinner before the snow started to fall again. After some online talk and flirting, we had decided to finally get together during my science teacher's convention in Denver. The conference was over but I had scheduled a flight the next day so I could finally meet you. I had booked us a quiet room at the Copper Mountain Resort so we wo...

The Spider & The Fly

by lucky lady on Sep 17, 2017
Mature

I had never thought too much about the cleaning ladies who came once a week to go over my apartment. I left their money before I went to work and, when I returned, things had been tidied up, the dishes washed and the carpets vacuum cleaned. Some were more conscientious than others; not that I was that bothered. I hardly saw them from one year to another; whe...