Asked out on a date

[Fiona_44]

Jessica,

A few words of advice:

1. Do not drink too much, have one or two max depending on what your tolerance for alcohol is. If your "date" insists on trying to get you to drink more kindly tell him to f*ck off.
2. Do not be overly nervous. Nervousness telegraphs to others that something is wrong & will cause them to examine you more closely.
3. Someone recently posted on another thread that "people see what they expect to see". If you look & act female, that's what they will see.
4. Let your date order for you so you don't have to worry about your male voice.
5. Act confidently, walk in like you have done this dozens of times before.

Above all enjoy what is liable to be a very interesting & unique experience.

[Stephanie47]

Assuming this post is on the level I think it may be a great experience. It must be terrific to have a wife and friends, who are supportive; especially a male friend who is willing to assist in this adventure. My adventures outside my home have been solo strolls in the evenings with an occasional Halloween thrown in. You mention Las Vegas which I think would be a good place as "Whatever happens in Vegas, stays in Vegas," and, posts by others makes it seem Vegas is "anything goes."

If I were in your heels I'd make sure my wife or one of her girl friends would do my makeup. I'd get a really nice wig. It would be full femme; attractive dress and heels and hosiery. A nice restaurant with booths, not tables out in the open. Follow the dining up with a run to a casino. If you have some time, practice walking in heels (try a low block heel) and practice female mannerisms.

You mentioned the adventure is with a "few friends." If you want to get your feet first by going out en femme; suggest your wife and some female friends take you out on a dry run.

[docrobbysherry]

Jessica, I see a lot of BAD advice here.

You're not going on a date. This isn't about romance, eating or drinking. It's about your 1st time out!

You're going out dressed with a friend. As such u 2 should discuss this in advance. Your comfort will depend on his comfort.
And, I only know a few men who would be comfortable out with a CD/trans!

Go somewhere where u will both be comfortable and have fun!

[jessicabf]

Wow. So many responses!

I'll see if I can hit them all...

I understand the thought to do dry runs. It's a good idea, just means I would have to delay my date!

Yeah, my SO and friends will be in a nearby booth/table as support (and likely lots of giggles).

As far as the sexuality of it all, sure CDing has that component since we are sexual beings. But not everything has to be focused on that, IMO. I mean, what's the goal? If it is to "be a woman" then focusing on the non-sexual parts of femininity is good. Women don't get aroused by wearing a bra and skirt. This is a subject for a long other thread, so I'll end it there. In this case, it is focused on enjoying the feminine experience of a polite date, that's it.

No worries about getting drunk. Ain't gunna happen.

Great advice on having him order. It's my voice I worry about. I don't have an overly masculine voice, but have never tried voice training. My SO tried to get me to practice in the car the other day. Just ended up laughing alot.

There isn't any chance of being left alone with no ride. So I'm good there.

Motivations of my date? Honestly I don't claim to know completely. He isn't an entire stranger, as we have met before. Never would have thought he would ask me out one day. Haha! Is he interested in a CD'er? Maybe, I will ask over desert.

Good to know about the restroom. I was worried I would have to insist the place have a unisex restroom.

At first we were thinking formal, but it may turn to semi-casual... I look good in my jeans (with my hip/butt pads).

As far as makeup... I have to admit, my skills are raising above my SO's in some areas. Her sister is jealous of my make up brush kit. I have the wig in my profile pic... deciding now if I should find another. *thinkingface*

And YES, I am very thankful to my SO. I know many here have less positive situations, but in my case, she and her sister have been the driving force in many ways. I'm just trying to keep my skirt from flying up during the ride!

Thanks again ladies for all the advice! If I do the solo thing first it may be awhile before the date and there fore any reports on how it went.

[SIZE=1]- - - Updated - - -[/SIZE]

Hey docrobbysherey, I didn?t see your post when I posted my reply?.

That is a great way to think of it. First time out! Just with friends?. on a date? okay, so a little different, but point taken!

The guy is totally aware of the situation. I think he likes the idea of being ?used financially? more than dating a ?guy in a dress?. But it should be fun.

The goal is for all to have fun. I?m sure after the date we will all chat about it, have some laughs and down the road have some interesting inside joke giggles when not ?enfem?.

[TheHiddenMe]

It sounds like you, your wife, and SIL have it under control. So just go for it, have fun, and report back here, because we will all be interested how it went.

One more revisit on the bathroom issue. If your wife and SIL will be at the restaurant, just have one of them go with you. I've done that with my girlfriends before (gone solo too). But I always remind my girlfriends that I don't like to chat "over the stalls", because I don't want others in the restroom hearing my guy voice.

And as to your voice, it's really not that big of a deal. The wait staff are generally trained to be professional and respectful.

It's interesting the guy has his own reasons for doing this (rule #1: every guy has a kink). Sounds like your "friend" has a bit of a findom thing going on, not only with you, but also your spouse and SIL (a/k/a the "ringleaders").

Again, do it, have fun, report back. And pictures, of course!

[closets]

What an awesome opportunity to wear something dressy and have the ultimate accessory - a guy

[Just Dana]

That sounds like a blast. Have fun!

I'd skip the dry run, if I were you. Having three plus people for support, especially one of them a guy as your date, seems more safe/comforting to me than going out alone or just with your wife.

Dana

[Rachel Anne]

Hi Jessica,

I had a similar event for a Christmas party this year. A long time good friend who is the only person who knows, asked me out. It was also my first time out with people, and I was very nervous, but he was a real trooper and everyone was awesome, and I had a great time.

I was super self-conscious, and it was semi-dressy, so I wore a nice dress with an Ann Taylor jacket over it, and some comfy heels (don't forget the comfy part!) and it worked out fine. Don't forget some makeup for touchups in your bag.

[jessicabf]

Thanks Rachel for the story. I know I'll be nervous. Unsure if I should go dresser, or nice-casual. Still need to know where he is taking me.

Good point Dana. SO thinks maybe taking several days off work, head to town and maybe do a mall walk all dressed. Then next day, get ready and have the date.

"accessory - a guy" .. haha... maybe I'm the accessory? Once thought is that I'm middle size (5'9" and about 160lbs). My date is a bit over 6' and likely a good 40-50 larger. So it will be an interesting feeling being the smaller one on the date. (besides wearing what I'll be wearing. lol).

[Patience]

Thanks Monica! Great suggestions.

Dark subdued restaurant, or a loud and bright one?

I was going to suggest you should narrow it down to establishments with gender neutral restrooms, since that seems to be a big concern.

Since there's seems to be no real chance of a relationship and you'll have an entourage in tow, this "date" seems highly farcical.

If you're uncomfortable going to the ladies' room alone, have your wife go with you. Going in twos to the restroom is a famous female trope.

Enjoy your outing enfemme, as at least that part of it will be real.

[Valerie Louise]

Update? Still on?

[Adelina]

So envious! Enjoy it.

[countrygirl]

So envious. Have a great time.

[Di]

Closing as it has been over six weeks since this was written and no updates and she has been online.
The OP can pm me to reopen if she wants to update but before the next weekish because it will then be closed permanently as we close older threads as maintenance.