Interesting Proposal

[Alyssa]

So as you all know my girlfriend is super accepting of my choice to crossdress even to the point of taking me shopping and having me try stuff out for her to judge. I think she enjoys dressing me up more than I do. However recently she suggested something that I find interesting, and by interesting I mean I don't know what to think of it.

She knows a guy and said it would be cool for me to go on a date with him while dressed, she would tag along with a girlfriend and call it a "Double date". Now I'm not intimidated by the prospect of another man, considering that when I'm not Alyssa I'm a martial artist. But I can't help but feel like something is turning in the girlfriend's head and it is somewhat worrisome.

Don't get me wrong. Dressing all day and playing the part of a girl all day with a guy sounds like fun, but idk why she would suggest it so out of the blue o.o

[Stephanie47]

I'd be worried too. And, what is next after the date? And, what will the man expect of his date? You and a guy, she and a girl? Interesting to say the least.

[Allisa]

Hmmmm, sounds like your girlfriend has another motive or a fantasy she wants to play out. She knows a guy for you to "date"? Now I'm worried for you.

[crystaltvco]

Has the topic of intimacy with others been brought up before? I am jaded and smell an ulterior motive.

Ask her flat out where this idea came from.

And, this is none of my business, are even attracted to guys when you are Alyssa?

Food for thought.

[Alyssa]

I would assume she's trying to fulfill another fantasy. Worry isn't so much the word for what I'm feeling it's more a matter of knowing the why behind it. I asked her and she just dances around the subject and, tells me that it's just for fun. Ive stressed to her that I will go along with certain things as Alyssa, but not as Alyssa I am still a man who knows what he wants and is interested in. As far as being attracted to guys, I've mulled it over before but I consistently come to the conclusion that the only person I'm attracted to is her. It's just a weird situation and ultimately the thing that concerns me is developing a fear of her leaving me if I don't do as she pleases on things like this.

[Tracii G]

You are a man put your foot down and say no.
I'm jaded too so I smell a rat.
If she dances around the issue its obvious she has ulterior motives.
Your first mistake IMO is you ASSUME and we all know women don't do things without a plan.

Is your GF your same age and how long have you been a couple?
The reason I ask is women in their 20's are very devious and deceptive.

[Alyssa]

I am coming up on 24 and she is 22, we've been dating since last May, so that's almost a year now. I'm probably going to let her know that she can't have her way with me just because I like being feminine.

[Mayo]

Obviously everyone is hinting that she may be interested in a MMF threesome. I'd suggest asking her straight out. Say that you have thought about her request and don't have any objection to roleplaying but you have no interest in taking it further (and be very clear about where the roleplaying will stop for you). I'd also encourage you to have this conversation in a non-confrontational manner in order to keep the lines of communication open - just because you may not be interested in this activity specifically may not preclude you from being interested in other, ah... 'non-traditional activities' and you don't want to shut her down about kinks in general (unless you do...).

[Maria 60]

Hm! Never came across something like this before on this site. I will say a few Halloweens back we dressed up and went friends house hopping, the last house we went was my friends brothers house. When I was leaving he came up to me and told me how great I looked as a women and he lifted my skirt and felt my leg from ankle to waist exposing my panties and telling me I have beautiful legs. My wife caught this and asked me if I enjoyed it, I was honest and told her it was the first time I felt like a women, but she made a comment that what I made him do I was more of a sl$t. She admitted it later that she got aroused seeing that guy feeling me up. I don't know I thought I was the weird one but I think women have a weird imagination. In my situation it wasn't planned but I would believe that if my wife would have asked me to let my freinds brother feel my legs I don't think I would be OK with it. Just talk to her and try to find what her true feelings are, who knows mite be fun. Lol let us know how it goes.

[ReineD]

Don't get me wrong. Dressing all day and playing the part of a girl all day with a guy sounds like fun, but idk why she would suggest it so out of the blue o.o

Because she knows that you'd like to do this? My guess is that she wants to make you happy.

It's just a date, right? Four friends going out in public together, with you getting the chance to feel what it's like to be a girl out on a date with a guy?

I'm probably going to let her know that she can't have her way with me just because I like being feminine.

I have a feeling this is more about what she thinks you want.

[Alyssa]

I would gladly accept that if she were more straightforward about it. I mean dancing around the subject when I ask and voice concern is no way to reassure me that there's nothing else on her mind. If she truly means for me to be happy and give me an experience she thinks I would like, then 10 times out of 10 I would do this for her. But when she dances around the subject and brings something like this up so suddenly, I feel skeptical to say the least.

[docrobbysherry]

You're both very young, Alyssa. Neither of u can be expected to know what u want yet. I suggest u go along with her ideas. It sounds like u want to. This may be the only way to find out what she's up to.

She may think you're bi or she may want to try that out herself. I predict you'll be sorry if don't experiment safely while u have the chance. Life is about finding out what u do and don't like. What r u afraid of? U can always say no when she/they want u to leave your comfort zone.

Who knows? U mite have a lot of fun. And, if nothing else it will be a great story to tell to your future girl friends! (Or boyfriends?)

[Jess S.]

Be careful may be fun but think it thru and talk about it a bunch with her first.

[ReineD]

I mean dancing around the subject when I ask and voice concern is no way to reassure me that there's nothing else on her mind.

What do you mean? Can you give me specific examples?

[heatherdress]

Seems more than just trying to make you happy. She wants to double date with you with her girlfriend. No one here knows anything about your girlfriend to know her motives, which could be to please you, test you, please her, experiment or something else. We also do not know your date or her girlfriend. Or where she wants you to go. But it seems like you should have an appropriate explanation (not "dancing around") from her before you agree to the date. It could be a real mistake unless you both understand each other before doing this.

Also, since you just started crossdressing a few months ago and since you have not told anyone else except your girlfriend, do you really want to go out dressed with people you may not know well who could take pictures and tell others. Is that OK at this stage for you? You have to assume they will tell others. You girlfriend might be well-intentioned but might not realize the risks of exposing your new hobby before you are ready.

[NicoleScott]

The guy pays for the date, right? Yeah, go.

[sarab]

Sorry, Im in the be cautious camp. Something just seems wrong, especially if she's evading giving you a reason why she wants to do this.

[Robin414]

I'll say it's interesting!

I've read every reply and with each one I go from thinking "Ya, somethings fishy 😞 ", to, "Hey, that's a great idea 😀 " and back again 😐

[ReineD]

Well yeah, everything looks fishy until there are specifics. Until Alyssa comes back and describes what exactly the girlfriend danced around, anyone can make wild stabs about what is going on. My guess is based on what I know about GGs (because I am a GG and I've spoken to many other GGs here over the years). Other people will make guesses based on wishful thinking or worst fears.

[larry]

Did I just click on a different site ? Hehe

[Robin414]

You DO know I was siding with your take on this one Reine! 😉

[ReineD]

Yes Robin, (I did use a smilie in my post)

[chelyann]

drag your feet for a little while and see what she says, then go and have fun

[emma-louise]

go for it, look at it this way its a free night out and a meal, just be careful of your gf,s motives

[Krisi]

I suspect the intention of this "date" may be sexual. That she wants to watch you being "done" by this guy. Are you ready for that? I could be wrong of course, but my wife has never suggested anything like what you're talking about.