I'm a crossdresser who got asked out on a date by a male friend. Should I go out with him?

[Anonymous]

I'm a guy who likes to crossdress, from time to time, and most of my friends know that I do. Recently, one of my guy friends asked me out on a date. Obviously, dressed as a girl. He admitted that he's into crossdressers, and the he's attached to me when I'm dressed as a girl. I am kind of curious, but not sure if I should. What should I do?

Go out with him

Tell him that I'm not interested

Updates

1 y

So, I did say yes and we went out the night after I posted this question. It was my first time going out on a date with a guy. He took me to dinner at Thai restaurant. I wore a pretty cocktail dress with slingback pumps. I truly felt like a woman that night. He treated me like a lady. I loved it. Whether or not we go out again, I will always cherish that night. I don't like to kiss and tell, but I did spend the night at his house ;)

Updates

9 mo

I'm still seeing the same guy 6 months later. It's been one of the best relationships that I've ever had. He treats me better than anyone ever has ❤️

[Flower7]

If you’re not attracted to guys, then you shouldn’t go. If you are, it would probably be okay to go on the date.

[Asker]

@flower7
I'm not particularly attached to guys but I'm open to seeing what happens.

[Asker]

@flower7
I said yes. I've never actually been on a date with a guy. I'm excited all the same.

[Flower7]

Have fun.

[Asker]

@flower7
Thanks.

[Asker]

@flower7
We're still together. I never would have imagined.

[Flower7]

Wow, that’s amazing.

[Asker]

Yes, it has been. I never imagined that I'd fall in love with a guy ❤️

[Sasha0426]

Go for it! I think you’ll have a great time. If you do go, give us details 🥰

[Asker]

@sasha0426
I'm definitely leaning towards going out with him. I'm curious, and why not I already know him. As far as details are we talking kiss and tell 🙄

[Sasha0426]

I guess what I meant was let us know how it went.

[Asker]

@sasha0426
I know lol
But who knows 🤷
Wish me luck if I do.
Thanks for the encouragement.

[Sasha0426]

Good luck 🍀

[Asker]

@sasha0426
I said yes

[Sasha0426]

Yay! 😄 So when’s the date?

[Asker]

@sasha0426
Tonight. I don't know the details yet, but I can't wait. I've never actually gone on a date with a guy.

[Sasha0426]

Awesome! Well, have fun and be safe ☺️

[Asker]

@sasha0426
Thank you and I will 🤞

[Asker]

@sasha0426
I had a great time. He took me to dinner, out for a few drinks after, and then back to his place 😍

[Sasha0426]

How exciting! I’m so glad you had a good time. Are you guys going to go out again?

[Asker]

@sasha0426
Possiblity. We'll have too see. I'm still at his place, if that says anything.

[Sasha0426]

It does! Hope you two go out again. You seem you like each other 😁

[Asker]

@sasha0426
As far as going out again it looks good. He was a complete gentleman. He treated me like a lady. Whiich was very nice and different since I'm usually the one treating a woman like a lady 😍

[Sasha0426]

Awesome! So happy for you 😄

[Asker]

@sasha0426
Thanks. It was very different. I found myself in a different role. It was wonderful, and I have no regrets. We'll see where it goes

[Sasha0426]

A Thai restaurant. Fancy 😁

[Asker]

@sasha0426
😍😍

[Asker]

@sasha0426
We're still together. I never would have imagined. Thanks again for the kind words.

[Guy13]

NOOOOooo. It is a friend and always bad idea.

[Sasha0426]

There’s been a lot of cases where friends dated each other and ended up as a couple.

[Guy13]

@Sasha0426 I don't know any personally so you're experiences are better than mine... No Wins from same workplace either... are

[Sasha0426]

I’ve been talking to them and they did go out and had a great time 😄

[Guy13]

@Sasha0426 There you go... Cupid is out and about already...

[Asker]

@guy13
I don't know if Cupid has anything to do with this, but I did have a great time on a date with a wonderful guy.

[Guy13]

Somebody deserves it so might as well be you...

[Nikki1989]

Go for it. Have a great time.

[Asker]

@nikki1989
I think that I'm leaning towards going out with him. Why not, right!

[Asker]

@nikki1989
I said yes.