First Time Crossdressing Stories

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First Time Blowjob

by MyWhoreWife on Dec 10, 2019
First Time

I'm a man and I love crossdressing. I love the feeling of nylons on my legs and wearing strappy high heel shoes. While wearing them I would wonder what it would be like to suck a COCK in them. Kneeling between a man's legs and sucking his hard and meaty COCK. I started to go to adult cinema's in the downtown area after accidentally discovering their existen...

My First Time Sucking Cock Pt. 01

by katiecdsub on Sep 13, 2017
First Time

I was first seduced at 18 in the steam room of a community health club by a strong black married retired football player in his late 30's. He was 6' 2", 220 with a 9 1/4" (measured with my school ruler later) uncut cock that was thick and veiny. It was something that just happened at a lucky moment in time and we both enjoyed it for many years in private. We...

A First Time for Everything

by miniwritessmut on Jan 11, 2018
BDSM

"You know, when I bought this I kinda hoped *you* would be the one wearing it tonight." "You told me you'd do anything for me tonight, right? 'It's your birthday, babe, and I'm totally at your disposal.' Exact words, there." Michael looked in the mirror and sighed. She was right, of course, and he should have known by now that things rarely, if ever, went...

Diary of First Time

by hubbyofprincess on Sep 11, 2017
Loving Wives

This is the journal of my life and the evolution of my sexual awakening over the past four years. My name is Nina and I am a 40 year old Caucasian woman who is happily married with four wonderful children, a devoted husband, and a good job. I am your average neighbor who lives right down the street, or you see rounding up the kids at school, and you would mo...

Showing Off For My Wife's Pleasure

by HotJennieh on Sep 19, 2017
Fetish

A first time effort based on real events. * There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my face and chest and r...

It All Started With A Dildo

by AmyMaid on Apr 22, 2025

It all started with a dildo and experimenting with crossdressing and after the first time I jizzed like a girl I was a wrap from that moment on. I started doing it more often and eventually I was able to make it happen several times in a row with a toy but I had trouble having a man do it for me. I was a little self conscious about it and I wasn't sure how s...

A Fantasy with Lisa

by chastityfan on Sep 13, 2017
Fetish

I met Lisa for the first time just after finishing a workout at the local gym. Over the next few weeks we ran into each other on a regular basis and ended up going to out for a few pints. Spending time together eventually put us in bed together and we decided out relationship was best left as a friends with benefits situation. Over time we discussed each oth...

Happy 21st Birthday

by lpacphantom on Sep 1, 2017
Group Sex

This is my first submission, the first time anyone but me has read my work. I would like constructive feedback. I hope you enjoy. The events are fictional, but the desires and characters are based in real life. This story contains male on male action and hint of crossdressing. If that offends you, don't read it. It all started before I even had my first...

Crossdressing Exhibition Fun

by iwant2suckabig1 on Oct 6, 2020
Exhibitionist & Voyeur

I have had a bunch of adventures that utilize both my fascination with dressing up in the sluttiest clothes I can find and doing nasty crazy things in public. I travel all around the world for work so have plenty of opportunities to pursue my fetishes in strange towns and cities where no one knows me. I will share some of these TRUE experiences with you. I...

A Fantasy Night Exposed Ch. 01

by tfrah on Sep 12, 2017
Fetish

This is the first part in a story based on my fantasies which my wife has long been encouraging me to finish writing and publish. In my defence this is also my first ever submission and the first time I've tried to properly finish a fantasy story so I'm also very curious to see its comes out purely self indulgent or if it actually works as an erotic story. I...