A first date - what to wear?

So after meeting a fellow cross dresser at my local pride event on Saturday I’m going on a date with them on Wednesday.

The problem I have this will be the first time I’ve dressed up “normally” for a date with another cross dresser and have absolutely no idea what to wear :disappointed:

We’re planning to go bowling then dinner and drinks (their choice not mine)

Can you lovely people give me some advice please?

I’m sure @Melody1 will be able to help :blush:


You need to wear something you can move in so you can swing your arms to bowl, so nothing too restricive. And a pattern would be better to hide any sweat marks if you’re a sweaty Betty like myself :wink:
My pick would be jeans and a shirt or smartish polo shirt but something with a bit of flair :tipping_hand_man:t2:

Thanks @JoCat :blush:

Definitely thinking something not too. Restricting for bowling! Wouldn’t say I’m a sweating person but was thinking a nice summery dress if it’s hot.

Let’s be honest, nothing goes well with bowling shoes :joy:

If you want to match the bowling shoes perhaps a clown outfit ? :rofl: :rofl: :rofl:

A summery dress would be perfect and the bonus is the breeze you’ll get on your thighs :wink:

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That was my thought exactly @JoCat just got to go not too short​:joy:

@Latex73 i do have a Harley Quinn outfit but that’s more for the bedroom :joy:

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I’m a cross dressing tomboy so for bowling, the go to would be:
Hoody, short shorts, stockings and suspenders, with some cute trainers. . (the rainbow fishnets are from Lovehoney and would also work for bowling)


Thank you @Melody1 :blush:

I have got some rainbow tights too but I’ve just fake tanned and wanted to show the legs off :joy:

Cute trainers with frilly socks was my plan!

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Short shorts or mini skirt it is then

@Melody1 think it will have to be :blush:

Haven’t been so nervous for a date in years :relaxed:

Thank you for your help x

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Be yourself and wear what you feel comfy in :blush:
If dressing normally then why not go with some jeans and a nice top… can always wear some lingerie under it if makes you feel more comfortable


Thanks @AJSTAR think after emptying my wardrobe I’ve decided on a lemon yellow midi dress with denim jacket can cute lil trainers with frilly socks :blush:

I’m now thinking about underwear and that’s a bigger minefield than the outfit :joy:

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Fantastic!!! Sounds like you’ve got this all sorted :smiley:

@AJSTAR I have all except underwear (just in case things go really well :crossed_fingers:)

Due to the dress I’ll need something that doesn’t cause a VPL :joy:

If you’re looking for knickers that work under a dress, these are good. Have fun, hope it goes well :smiling_face_with_three_hearts:

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Thank you @Kitty-Cat01 :blush:

I had decent on a thong but these are so cute I’m now undecided (I appreciate the model probably looks 1000x better than me! :see_no_evil:)

I’ll keep you posted how it goes, very nervous which isn’t normally like me!

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So keeping a eye on this good luck​:+1:

You know I have never been on a first date, first girlfriend well I would only see her at weekends it was just a fun relationship no sex.

Second proper relationship we were friends to start of with well she was a mates sister so it was kind of a forbidden relationship at first alot of sneaking around.

Third relationship silly me got her pregnant before we could be proper and go on a first date.

Thanks @teacake its my first date in a few months so very nervous but will keep you posted :blush:

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I shall keep my fingers crossed :crossed_fingers:

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Thanks @AJSTAR I’ll keep you all posted how it goes :blush: