'My cross-dressing fella's obsessed with lesbians!'

(22 ratings)
Cross-dressing sex stories
I've been dating this awesomely sexy man for a little over a year now. He's always had this mysterious air about him which made him more captivating to me. Believe me, we've had our ups and downs. Added to the mix of things, I am much older than him by 17 years and he has bipolar depression and a few other issues thrown into it all. Those things aside (and they're enough as it is), he's recently trusted me with the knowledge that he likes to dress in women's clothes.

He almost always wears thongs, sometimes two at a time to cover his 'boys' and his extra large manhood. Once he saw I was okay with it, he started feeling free to wear nylons, bras, dresses and mini-skirts just hanging around with me at his place. I'm still okay with it, it's cute actually. I know I made him very happy with my acceptance of his fetish. And as is almost always the case with cross dressers, he's a heterosexual. I've set boundaries because I'm also heterosexual and don't want him dressed as a woman when we're having sex.

But now I feel there's a further problem. He's fixated on lesbians, wanting me to go to bed with one (or more) while he watches me 'have fun' with them, which I can't and refuse to do! And as if this wasn't enough, I'm worried that when he dresses up as a woman, he likes to dress 'hooker' style with mini-skirts, garter belts hanging out, tank tops and he stuffs his bra to make his 'breasts' look huge.

He then drives to a local park that's supposedly famous for sleazy men who go there to have sex or whatever and he likes to strut around, teasing them. He normally goes after dark - I've been with him on a couple ventures and he's exhilarated by the experience. It was funny at first, seeing him darting behind trees and prancing around the circle in front of the parked cars. But I'm bored with it all now and he wants me to join in which I don't feel safe doing. Those people are freaky yet he enjoys it!

What's going on here? Why does he like behaving like this? Does he want to be a lesbian and that's why he obsesses about them? He says he's not gay and when he's in his male mode, he's very manly and strong. He wants to have me in his life forever he says, but I'm not sure how to cope with all of this!
Please help.

What do you think she should do? Have you experienced anything similar? Share your advice in the Comments section below...

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Leave now. U got bored of what he loves to do every day, within a couple of days. Leave. No other way. He is trying to drag u into his fetish world. U obviously cant take it.


It's obvious he has issues. Make him go to therapy for his identity crisis, or leave.


Two things: accept it or run. Whatever feels most comfortable.


I dont think he actually follows through with it.


Run. Run like the wind. Leave now before you get too attached to him. It will just get stranger, you'll be pushed and pushed. It starts with their fantasies - what they would like you to do...until you want to keep them and try to please them. If it isn't remotely your thing don't encourage him by going with him to the park, let him go alone...and don't agree to the lesbian thing if you're not!

chris moss

first thing you should do is get rid off him he is not normal,cross dressing is one thing,but going to the local park for sex is a totaly different ball game,what if he catches aids or some other disease,then passes it on to you,also he needs reporting to the police if he is soliciting in the local park,he is just prostituting,plenty off sexy men out there that are normal?

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