Interesting Proposal

[Mayo]

I find it interesting that many posters are using words like 'fishy', 'rat', and 'sneaky' to describe the girlfriend's motives. It could be that she simply likes the idea of a MMF scenario or finds something else about the situation arousing and is either unable to articulate it or is embarassed to do so. It's not like most North Americans have open and honest conversations about sex without hang-ups. I wouldn't attribute 'negative' motivations to her without knowing more. Now, if she wants to get him drunk and have her friend take advantage of him or pimp him out as a CD prostitute, okay, that would be shady, but I want to give people the benefit of the doubt - when I'm not being a cynical misanthrope. :D

[ClosetED]

Very unusual proposal. I see it as
1) She thinks you want to experience more of life as a woman, even if you are scared to ask for it. Possibly based on your comments/actions. This is her way to give you that experience in a safe way, with her there to protect you.
2) She is testing you - wants to see if you will like being with a man more than with her. You can say 'I only want you', but until she has you experience this, she will not feel assured.
3) She wants to embarrass you

How much do you know about the guy? Is he bi? Homosexual? While you are capable of defending yourself, is it fair to play with his emotions if he might be led to expect more?
If only a social lunch, rather than date, it might be better.
some thoughts ...
Hugs, Ellen

[Krisi]

She thinks you want to experience more of life as a woman, even if you are scared to ask for it. Possibly based on your comments/actions. This is her way to give you that experience in a safe way, with her there to protect you.

There are ways for her to do that without involving other people. Use your imagination.

[NicoleScott]

All the speculation about the girlfriend's intentions. Why not cut through it all and ask her "why do you want me to do this?"

[Amy Lynn3]

Alyssa, I am in the corner of ReineD on this. I think you need to really consider the request of your GF. Go and have fun and if it ever gets to a point it is not fun. Just say stop. If you go out you will find out for sure what the GF wants and I think it will be a great outing for you.:2c:

[Pat]

Obviously everyone is hinting that she may be interested in a MMF threesome.

I don't find that obvious at all. I think you're projecting.

Alyssa: In the end it comes down to you. Perhaps I'm the one projecting now, but it reads to me like you don't have a problem with the proposed date, you have a problem with the feeling you're being manipulated and that if she manipulates you successfully she wins and you lose (somehow.)

If it was me, I'd go (but I've always been a risk-taker.) If I didn't go I'd spend the rest of my life wondering what might have happened. If I go, I find out and it's over in a few hours.

[Alyssa]

Hmm. Well there is a lot to address now lol. Sorry I haven't replied I just got to taking my lunch. When I say she dances around it I mean the following; we are both business to business sales people. She keeps using a tactic called acknowledge and ignore whenever I voice a concern. She will say something like "I understand Hun, don't worry if will be fun... So what do you want for dinner tonight?" I confronted her about it yesterday and she did this exact thing. Now maybe she's just trying to build up my impulses, but it would be nice to know what exactly she wants from it. Cause let's say I go and I am not aware of her wants for this "date" then I can't make sure it goes well for both of us, and if it is something that I'm not ready for that she's trying to experiment with then I news to know before it does some kind of damage to my psyche.

[Jenniferathome]

There's a really easy way to solve this mystery: ask her directly and do NOT allow her to skirt the issues. "Honey, exactly why do you want me to go on a 'date' with a man?" Exactly what will you get out of it and exactly what do you expect me to do on this 'date'?"

An inability to answer implies something nefarious.

[raeleen]

As a few other folks have mentioned, I think a sit-down conversation about what the expectations would be for the date would be useful. Even some role-laying scenarios, if that works for you guys. If she dances around the subject still, I think laying it out that you will be more comfortable and able to enjoy something like this (if in fact that's what you want) if you know what expectations are going in so no one has their feelings hurt later would be good. Ask her point blank, 'what happens if he starts to kiss me. are you ok with that?' 'what happens if x happens?' keep diggin with the hypotheticals and hopefully that'll help to unearth what she's thinking.

It sounds kind of fascinating, and I hope you keep us posted on whether you ultimately decide to go. Good luck, girl!

[Tina_gm]

3 things come to mind. What ReineD said makes a whole lot of sense. 2nd, she may be doing this to see how far you will go with the whole dressing thing. 3rd.... I once talked to a woman who was just flat out into anything and everything. And didn't care that anyone knew. She had a bi-sexual husband and proudly admitted to me and to anyone willing to listen to her that she loved watching him have sex with other men, and then join in of course too.... Some people are just like that. Maybe she is just one of these people.

[rachael.davis]

OK so your girlfriend enjoys you crossdressing, and from your first post encourages it. She's suggesting a "threesome" date - you, her, and a straight (?) guy
best (?) case scenario - she wants to go out with a crew, and is interested in seeing how you do in a social situation with a man
middle case scenario - she is looking expand your relationship gradually, and wants to see how you deal with it
worst (?) case scenario - she is interested in a threesome with you, and a straight guy - how quickly is anyone's guess
I've done sales there is a point in negotiations where you pass, or you play

[Pat]

She's suggesting a "threesome" date - you, her, and a straight (?) guy

That's not the setup explained in the OP. It would be Alyssa and The Guy, Alyssa's girlfriend and a female-to-be-named-later. The scenario was labeled "double date."

[heatherdress]

You only started to crossdress a few months ago. No one else knows except your girlfriend. Do you want to her friends to know? There is no way to maintain privacy if others know. There will be pictures of you in a dress on a date with a guy. Are you ready to explain that to others?

[ReineD]

Alyssa, thanks I read your post #32. I agree with Jennifer. Next time she changes the subject, tell her that you want her to stop doing this and tell you what her motives are. Ask her if she really wants you to date men, or anyone else other than her for that matter. It's a valid question.

And while you're in the conversation, ask her if she understands the difference between enjoying the role-act of being a woman on a date with a guy, and fundamentally being attracted to the guy whether you are dressed or not. Who knows. It could be a test ... (is there anything in your past that would make her believe that you are, indeed, attracted to men)?


<Edit> - Just so you know, the majority of women who find out about the CDing wonder about two fundamental things: whether their SO actually wants to be a girl and whether they are attracted to men. A lot of wives/girlfriends believe that the reason to dress is to attract men. And if your reaction to her suggestion is positive, then she might think she has her answer.

[summerbunny]

Its a trap,a catch 22,a condudrum, a setup
Don't be "the gimp",don't be the Mark
DON'T DO IT!
its psychological romance, its SMBD

Its a mind game. It a mind F***k.

Fair warning,run,run away,run fast

You've been warned!
You'll be in a intricate predicament from an intricate plot

[ReineD]

No. lol. Best to just talk and ask the girlfriend to say what is really on her mind.

[summerbunny]

It could be a" Fools proposal".
You can't win with those.

She's trying to "Do you"
Talk ,fight are flight

[Mayo]

Obviously everyone is hinting that she may be interested in a MMF threesome.

I don't find that obvious at all. I think you're projecting.

Maybe I am

She keeps using a tactic called acknowledge and ignore whenever I voice a concern. She will say something like "I understand Hun, don't worry if will be fun... So what do you want for dinner tonight?" I confronted her about it yesterday and she did this exact thing. [...] it would be nice to know what exactly she wants from it.

Thanks for that clarification. She's definitely dodging the question, and that's not helpful. You have a right to know what it is that she wants/expects and what your role in this event is supposed to be, and you have the right to say no if you aren't interested. In my opinion, you should tell her that you'd like to discuss it and to know exactly what she has in mind; if she refuses, then just reply that you're not interested if you don't know what you're committing to.

[Lorileah]

OMG, really people? You get offered what you want and you immediately suspect the worst? You know sometimes a cigar is just a cigar. No underlying agenda. At worst I would suspect that this little exchange was more a fantasy (for either or both parties). In my experience this type of thing would have led to marvelous night or...romance, between me and my GF and never set foot outside the house.

But it DOES bring up one thing I really press for here...trust. Alyssa you just proved you don't trust your GF by even WONDERING if she had other ideas than what she told you.

[Alyssa]

I can't explicitly say I want this. It's something to think about, but not a priority or an immediate desire. I do trust her, it's just that when you bring something like that up, and then avoid and real answers, then you make the other person question what you truly want. I spoke with her tonight over dinner, and ReineD was right, my girlfriend was just curious to know if I was into guys and if I actually wanted to be a woman. She said she was feeling a little insecure, despite being supportive. I reassured her that while being a woman sounds like a lovely endeavor, I only like dressing for the sake of looking pretty when I'm relaxing. I very much enjoy dressing in designer men's suits for work, and when I go out to a bar just as much as I do wearing pretty dresses and high heels. She said her friend is not straight, he's bisexual, to which I replied that if it actually made her happy for me to 'go on a date' with her guy friend so she could see my girly side in action then I would love to do it for her. I was however clear that I don't feel any kind of inclination to let a man touch me in any way other than an arm around the shoulder or maybe holding hands. She said that my concerns were fair, and that she danced around the subject before as to appear more confident, rather than appearing "weak" in front of her "beautiful gf" over the feeling of being potentially unwanted. I'm going out this weekend, and I'll be sure to share with everyone my experiences

[LeslieSD]

You guys are over thinking it.

Just go with it, but state your boundary up front. If I were you, I would say "Sure, I would go with you and your friends. But I want to make it clear that I have no interest into men. We can go hangout and have some fun time *as friends*", and really emphasize on "as friends".

Have fun and come back to report what happened. You have the envious situation for most of us here.

[Genifer Teal]

You can guess all you want, the only way to know learn and grow in who you are and who you want to be with is to go and see what it's like. You are a far better judge of your girlfriend that we are. You've been with her; we can only guess what she's like. Knowledge is a powerful thing you will both learn from this experience. you will by being with the guy, she will be watching you with the guy as well as being with her friend. maybe there's more there too. the only way to find out is to go and see if you have a good time. maybe you'll learn you like it and lose interest in her. maybe she will learn she likes it and lose interest in you. whatever the experience teaches you both the future is uncertain. it's far better to know now than to find out what you missed or might like better or who knows what. like I said too much uncertainty to not want to find out. this could bring your relationship with each other to a different level. sometimes you need to take a little risk to get a reward. stop overthinking it.

[Robinsinclair]

I agree with Genifer and Leslie.

Go with it.

Enjoy. If it's not fun or becomes not fun - stop.

Regardless of how it turns out, you will learn something about yourself and your girlfriend.

[lingerieLiz]

When I was a couple years younger than you are, I had a friend who was gay and we went out on several "dates" so I could dress and he could be seen with a girl. A guy he liked had a cute sister who was open to my dressing. We double dated on several occasions. The guys would sit in front while us girls would sit in the back. It was fun for all.

In your case there will be 3 girls and 1 guy, is your girlfriend going to play as a lesbian?

[Amy Lynn3]

heather, I think you are thinking what I am thinking.