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The time I (accidentally) kept a crossdresser in chastity for over 50 days [M27, T23]

This story took place in June, July and August 2015. It was between myself and a crossdresser I’ve been meeting for a few years. She’s called Kyla – and I might as well shout out to her as she’ll be reading this story. If you have any questions for her, post below and I’ll try my best to get an answer. Kyla is 23 in this story and crossdresses only part time, really as an outlet. We’ve had a few deep meaningful conversations over the years and I’ve learnt that Kyla would transition but for the good things she’s got going in her life.

My husband not only understood, but encouraged

I made a post last week about my outing and that i loved it, but was unsure on how to tell my husband. Three days ago I spoke to him and he didnt quite know how to react, but then he told me his only regret was that he didnt get to watch me.

A perfect trip visiting a friend. (m/f)

Like any other person living in the 21st century, I spend a fair amount of time online. A few years ago, I became friends with some absolutely wonderful people from all over the world, and of course one of those people just had to be a handsome little fucker who lived nearly 4,500 miles away from me. We spent quite a bit of time flirting, at first I tried to be coy and cute but eventually I just unzipped my Batman onesie and sent him a topless snapchat. That's what every guy wants, right?

College Orientation [M/F]

I’ve browsed this sub for a while and figured I would finally contribute some material. I’m graduating from college in May and was thinking about some of the times I have had over the course of my career and thought others might like to hear them. The first memory is about my time as an Orientation Leader at my school. It was an easy gig that paid decent money to essentially just walk kids around campus. Most of these sessions were just day sessions but there were always 2 overnight sessions.

[M]y story (and pics) about my first time with a hotwife and losing my virginity part 1.

About me: 22 and a virgin. Never been on a date, never kissed a women, and never had sex. Including never having a hand job or a blow job.

All you need to know about her: 22 as well, married, and this was her first time meeting with another man.

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