Pegging Crossdressing Stories

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Taken by My Wife

by BlondeKaryn on Sep 12, 2017
Transsexuals & Crossdressers

My wife had recently found out about my crossdressing. She was a little upset at first, but then seemed to be more accepting of it as time went by. I came home from a business trip a couple of weeks ago to a welcome that I could never have imagined in my wildest dreams. I had taken quite a few of my clothes with me, and spent every minute possible on my tri...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

My Journey Ch. 01

by npanxx on Sep 19, 2017
Transsexuals & Crossdressers

I found myself in a midsized college town working on a problem that didn't want to be resolved. With assistance from my co-workers two and a half hours away I was finally able to correct the issue, and system operation was restored. It was late, I was more than three hours from home, and decided I did not want to make the drive. Instead I chose to spend the...

A Wedding Night Pegging

by pwlrstr on Sep 12, 2017
Fetish

"It would be more of a big deal if it was the first time," Jon had said, instantly regretting that it sounded a bit negative, when his fiancée Naomi had asked if he was looking forward to their wedding night. "I mean, I don't really believe in saving yourself for marriage or any of that crap. I think it's definitely been a good idea to have lots of sex first...

A New Beginning

by DutchAlex on Oct 30, 2018
Fetish

Carla sat in her car in the parking lot of the sex shop. Staring at the front door and working up the courage to go inside. The Fantasy Adult Fun store had just opened a week ago, but she had been thinking about this moment for a long time. Ever since she found out Jim had been cheating, through the divorce, and the year between then and now. It hit her ha...

Rm 209: First Sex as a Crossdresser

by MelissaMwaz on Sep 16, 2017
Transsexuals & Crossdressers

This is a TRUE STORY. I've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a kid and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-...

Israeli Femdom 4 Muslim Slaves

by Samuelx on Sep 11, 2017
Interracial Love

You've been a naughty guy, I told Rahim Abdullah as I spread his dark butt cheeks and eased my strap-on dildo into his asshole. Immediately the young Somali man went stiff, as something I call the shock of penetration came over him. It happens with every new submissive who experiences the joys of pegging for the first time. Gripping his narrow hips tightly,...

Interracial Pegging: Female Giant

by Samuelx on Sep 11, 2017
Interracial Love

Why is everyone so damn afraid of interracial pegging? That's what I want to know! My name is Beatrice Levin. A six-foot-eight, red-haired and green-eyed French Canadian woman living in the City of Ottawa, Province of Ontario. Folks, I am a big woman. And I know it. I'm damn near seven feet tall and weigh two hundred and eighty pounds. I was afflicted with g...

Blonde Fucks Blacks Ch. 11

by Samuelx on Sep 11, 2017
Anal

My name is Villa Jane Smith. Friends simply call me V.J. I am the Heroine of this tale, and is this my first interracial strap-on story. If you ask me, there aren't enough interracial strap-on stories out there. Please bear with me. I am a six-foot-one, somewhat chubby Irishwoman with short blonde hair and pale green eyes. Oh, and I've got big tits and a fat...

Black Couple's Guide to Strap-ons

by Samuelx on Sep 16, 2017
Anal

I thought I could escape from it but I've come to realize that in the end there's no escape. It doesn't matter hard you try or how strong your resistance is, you will get what's coming to you. Fate simply cannot be avoided. It doesn't matter if you're an individual with exceptional abilities. The fabric of fate cannot be changed. My name is Jamal Trevor. Fri...