Came out to best friend from Highschool

[Ariana225]

It's been 10+ years since I last had contact with him. We exchanged pleasantries via texting over a few weeks. We both had a secret that neither one of us shared in highschool. He is 80/20 bisexual leaning towards men. He was a big time player in highschool and slept with plenty of women. He has been in a relationship with his boyfriend for 9 years.

So I said why not and told him about my crossdressing. He was equally blown away by that news. He showed me pictures of when he went to a club as a drag queen and he looked better than I could ever pull off. He had a professional do him up. I wonder how well I could pass if a professional did me up the way he was.

He wants me to go to the next one as he puts it "where men become women and women become men". He wants to reconnect and hang out and go to a nail salon to get a pedicure (I found out he sometimes paints his toenails).

My wife knows that I told him about it and seems okay that I needed another outlet and someone else to talk about my crossdressing with. (She gets tired of it sometimes haha).

My only problem is I haven't discussed with her about me hanging out with him at a club 60 miles away and ocassionally going to a farther away nail salon to get pedicures together.

I'm only interested in women and he is in a committed relationship for the last 9 years. What would be the best way about approaching this with the wife?

[Jaylyn]

I can only tell you what I would do with my own wife. If I was in your heels I definitely would not lie to her. Lay the whole plan out, let her know how far you would enjoy going with it. I would also ask her what she thought about it and in my case I would respect her opinions on this. I would definitely try and keep everything up front and not get caught up in the moment with something that was not discussed before the event. That's just my advice so take it for what it's worth I've only been married to the same gal for going on 47 years so not an expert yet.

[Pat]

I guess I'd approach it the same way you approached it here. Tell the truth.

[Tracii G]

Yep tell the truth.
You say you are both in committed relationships so why do I sense that you think you two hanging out will lead to something else?
Are you thinking because he is gay he is going to put the moves on you?
That sounds very stereotypical to me.
Along the lines of when somebody finds out a friend or coworker is gay and they say " I don't care but he better not try anything on me".
See what I mean, thats the way I read it.

I have been thru that with a few of my very very straight friends and I won't go into detail about what I said to one of them after what he said to me and the others after they found out that day.

[Stephanie47]

I think you should read your July 6th posting/thread. I think you're expecting too much from your wife. Even if she said it was OK to go on this trip I think it will raise a lot more questions about you. And in her mind, "Is there more going on than just reconnecting and getting nails done with a gay guy?" Stay home!

[Tracii G]

You could take your wife with you did you ever consider that option?

[Ariana225]

Traci, I wasn't trying to be stereotypical with my reply. That wasn't my intention. I just was implying I wanted to address it to my wife in that way. She trusts me, and I trust her. But I was implying the same as if I was to go with a straight cis woman 60 miles away that there wouldn't be no hanky panky going on. And yes I would consider taking my wife along, I don't think she would want to go if I asked.

Stephanie, I agree it's a lot asking my wife that. That's why i was looking for advice before I told her. If she is uncomfortable in any way then I bag the idea and don't go. She comes first always.

- - - Updated - - -

This isn't my first gay friend, or encounter. I have went to pride events before and got hit on. A polite no is very easy to do for me. Just like every straight woman isn't interested in doing me I believe the same is true with my gay friends. I didn't mean to offend you one bit!

[alexaxx]

My approach would be to have a glass of wine or two, make sure everyone is in a good mood, then lay it all out for her. I think it would help if she was good and relaxed to have that conversation. But hey, you’re the one with the heels on the deck, so go with your gut

[Nikkilovesdresses]

Invite him and his boyfriend to meet you and your wife, perhaps for dinner? If she sees him as part of a solid couple it will hopefully help. It all depends on whether she's the jealous type.

[Tracii G]

You assume she doesn't want to go?
Why don't you ask her or is it because you would rather she didn't go?
You do know cheating on a spouse is still cheating even if you are with a gay man. How do you think his man feels about you coming up to hang out?
I think all 4 of you should meet for dinner like Nikki said

[Ariana225]

Tracii, I would rather she go. She is still fairly new to my crossdressing so I doubt she would be ready to witness it in that type of environment but possibly might be ok if she wasn't there. I will be asking her both of those questions.

Also, I would never cheat on my wife nor hang out with anyone behind her back, man or woman.

Nikki, thanks for the advice! We have already discussed meeting for dinner some time. we haven't seen each other in a long time and would like to meet each other's families.

Thanks everyone for the response. I guess it won't hurt to take it slow and ask the questions. The worst that can happen is my wife says she isn't comfortable with it, which then it's a no go.

[ellbee]

Agree with the others.


All 4 go out together *first*! And no clubs, no "gettin' yer nails did"... Just an average dinner out.


Let a bit of time pass, *then* bring up the club thing. Ask your wife if she wants to go. Tell her you'd like her to be there... But if she replies she's genuinely not interested, then explain that you'd still like to go, yourself -- as it's something you'd feel would be kinda fun & a healthy "outlet" for you.


This is the way to do it, IMO, for best results. :)