Being A "Girl" For A Weekend

I'm a gay guy in my late thirties but discovered my crossdressing fetish in my early twenties. About a year after I started crossdressing, I met a guy on craigslist personals but instead of just hooking up for sex, I spent the weekend with him as his "girlfriend" and that experience was hotter than any hook up could have been. I really got into it and was so turned on by him treating me like he would if i was his girlfriend. I was turned on by him watching me clean up his place and how he called me by a girls name. I was nervous when he told him his buddy was coming over but it was hot how he told him I was his "girl". That weekend was like nothing else I've ever experienced and since then I've fantasized about doing it again. Of course, we had sex multiple times that weekend, but playing the role of his "girlfriend" was hotter than any sex. My only regret is that I refused to outside dressed up. But if I ever get the chance to do it again, I'd definitely like to go out dressed up.

Comments

Anonymous

by Anonymous on Jan 4, 2025 at 7:15 AM

My wife dressed me up a bunch of times and we go out to eat or shopping. I love being my wife's girl friend.

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Anonymous

by Anonymous on Jan 4, 2025 at 9:27 AM

I have a friend that loves dressing up. We will meet out of town at a hotel bar. We pretend we just met and I will feel him up in the bar. We end up with a room for the weekend and enjoy all the sex we can. I love taking him to dinner dressed up.

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Anonymous

by Anonymous on Jan 4, 2025 at 9:55 AM

Me and my best friend dressed up in our sister's things as grade school boy's and continued even after we were told it was gay. Yes it was because both of us are bi 19 year old smooth attractive sissy's.
We have no problem passing and as middle schoolers we had boyfriends.
We've had both boyfriends and girlfriends throughout high-school and lost our gay virginity in 7th grade. It's way good being with men now that we're older though it's important to use discretion more now than when we dated boy's.

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