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Feels different
I'm 18, guy, and have this same age buddy, we were always togather. Two months ago he started saying ** things to me, telling me I had a hot looking **, wanting me to were tighter fitting jeans. One night at his house he got me to put on a pair of his sisters **, and her lowrise jeans. I didn't know what to think about it, but I did feel comfortable doing it. Two Friday nights ago we were driving around outside of town, I was dressed like his sister, and I ended up letting him ** me. It didn't hurt, but I felt different things during and afterwards, excitement, embarrassment, confusion, but all in all, I liked what he did. That was two weeks ago, we still hang around togather, but he has never mentioned it, neither have I, but when we're togather, I get this weird feeling, and remember everthing that happened that night, and I'm sure he does too.
Sucking ** while cross dressing isn't gay, it's just real hot role playing. I will only do it while dressed up, otherwise I like women.
A bit odd and there's a possibility he may have used you to fulfill his ** fetish, which is a little skeezy especially if he didn't mention it... and I'm sure his sister wouldn't appreciate knowing someone wore her clothes for **... lol. But all in all I reckon no harm done if you don't mind and there's no hard feelings. If nothing else happens, no biggie, you had a good experience if I'm any judge, so all seems well.
Just make sure you don't let him manipulate you into doing something you don't want to do in the future. The thing about him wanting to control what kind of clothes you wear kinda weirds me out. Just be careful of boundaries if it looks like you two might bump off again, okay?
Kinda hot!
You should take it to the next step and let him know you enjoyed it and might be willing to be ** buddies and maybe more later on.