First Time Crossdressing Stories

351,059 results
Orientation
Length
Source
Infinite Scroll

Jake

by Troughton1963 on Mar 18, 2020
Romance

Summer 2700 CE Jake was murmuring to himself, "What the hell am I doing here? I detest these people." Jake dismounted his new, sleek, state of the art hovercraft truck. Jake was in construction and having a hovercraft to levitate any size load was a plus. Earth ran out of fossil fuels, such as oil and gas centuries ago. Jake, yet again, got roped into goin...

For The Whored: Beyond Ch. 37

by Thatawfulwowporno on Jul 15, 2020
Sci-Fi & Fantasy

"So, your mother is Elunara, leader of the SI:7, and queen of Stormwind?" Calysta blinked at Lulu. Lulu blushed and fiddled with her bag. "Please don't treat me any differently. I don't like it when people do." "No, I don't imagine you would. It is just a bit of a shock to meet some of her family is all." Calysta shook her head. "I would have thought that...

Naomi's Big Bang

by happilymarriedguy on Sep 12, 2017
Group Sex

This is what happened when Naomi and I got involved with a couple whose thing was gang bangs. Except we didn't know that until they suddenly sprung one on us one night. Their names were Brad and Lynette, they were in their late 30s and we first met them at our regular swingers' party. Naomi and I went with them four times. The first time was at the party,...

What's a Sissy to Do?

by _pdy_ on Apr 14, 2020
Transgender & Crossdressers

The following story is a fictional re-imagining of a situation I found myself in. At this moment, I have no real plans to make it into a series like some of my previous work. It's loosely based on true relationships that I've had with some likeminded people over the years, but it is nonetheless fictional. Anyway, I think that's enough from me, on to the stor...

Paradise Found and Lost

by Blubik on Aug 18, 2017
First Time

This happened really back in "olden times" but it still seems so clear and so important to me! I went to a boys-only high school and had no sister, and so knew little about girls except for the stories other boys told. Mostly lies! In the summer I was 17 I went to a music camp for two weeks and there I met girls, which I confess was more of an attraction t...

The Five Conditions - First Time

by Davieg40 on Aug 18, 2017
First Time

The Five Conditions – First Time My heart almost stops as the tiles slam onto the table. Oh my god no I have lost again. My whole life could be good but my addiction to the tiles is going to spoil things. My name is Tui and I am an eighteen year old Vietnamese girl. My friends tell me that I am beautiful. I know that my fiancé thinks so. My long black hair...

Finding His One Pt. 02

by Chewie417 on Sep 17, 2017
BDSM

Their first encounter was tame but it felt like an awakening for both of them. They spent time after learning about one another, sharing only little details at first. The feelings were intense but both kept them back for fear of falling to fast. Days went by and texts were sent, A smiley face here and kissy face there, and when they were together they foun...

Good Morning

by theAmateur on Sep 12, 2017
Loving Wives

I slowly awake, gradually becoming aware of myself and the daylight entering the bedroom. The first thing I notice is Robert. He is snuggled into the back of me, his arm thrown over me and cupping my breast. His breath tickles the back of my neck in a slow, steady rhythm. I felt the heat of his body and realise I am naked. Of course! We made love last ni...

My First Time

by ElephantJuice on Jul 15, 2020
Transgender & Crossdressers

My very first time sucking cock was with a beautiful blonde trans-girl with a big tasty dick. Firstly, I guess you should know a little about myself. I'm approaching 40, married and consider myself straight, I know technically I'm not but it's the category that best fits me if you have to categorise. I don't particularly find men attractive and have no urge...

Immortal Lovers

by VixxTheLover on Aug 12, 2020
Fantasy

This is a continuation of a story from the Cum Addiction storyline, along the "Your Daughter" path, which I wrote. I would suggest reading that story, but if you do not, here is a quick recap. John was a doctor treating a disease commonly called by the name "cum addiction disease". The disease made life difficult for those with it, as the...

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