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Original poster

So if a new guy tells you this....how would you feel????

42 replies

OhToBeFree · 13/05/2011 10:23

OK so getting to know a new guy. All ok but he's going through some issues with his ex so we're taking things slowly.

Last night he tells me that he once dressed up as a woman to fulfil a fantasy his ex had.....

I really don't know how to feel about it...........I find it a bit Confused

OP posts:
TurnipCake · 13/05/2011 10:25

Hmm, I'd be less bothered about what was said vs getting into something new when there are still issues with the ex.

Do you know what the issues are? Financial lose ends, unresolved feelings etc?

squeakytoy · 13/05/2011 10:26

He was doing it to please his ex, it doesnt sound as if it was something he did for his own benefit, so I wouldnt really worry about it.

madonnawhore · 13/05/2011 10:27

Hmmm, it's a little bit , not to mention bad manners to talk about kinky peccadilloes you indulged in with an ex.

Why did he tell you? What was the context of the conversation? If he was trying to demonstrate how he is willing to experiment in order to please his partner, then that's a good thing (even if the example he used was a bit clumsy and insensitive).

Or was he talking about how great his sex life was with his ex? That's bad.

Or was he trying to subtly tell you that he likes to dress as a woman sometimes during sex? Not necessarily bad, depending on what you're into.

mummyplonk · 13/05/2011 10:27

hmm, sounds like he was testing the water with you there ohtobe, I cant see how that would be another womans fantasy?, hairy legs in stockings, but it takes all sorts.

madonnawhore · 13/05/2011 10:28

Oh I dunno mummyplonk, I've always had a bit of a crush on Eddie Izzard, but only when he's in heels.

madonnawhore · 13/05/2011 10:30

On a serious note though, it is a slight red flag that there are still 'issues' with the ex, and that he's bringing up his sex life with her in conversation with you.

Cross dressing stuff aside, that isn't really a good sign early on in a relationship. What are these 'issues' with the ex?

JessicaDrew · 13/05/2011 10:32

my guess is its something he enjoys doing during sex and he would like to do it with you
bit like my DH confiding he liked fetish wear, and telling me Blush and i am completely ok with that

Original poster
OhToBeFree · 13/05/2011 10:33

Well we were talking about perhaps going away for the weekend and what we'd like to do (just random talking really, not actually planning) and I asked if he likes sexy underwear, not on him but 'whatever floats your boat' type of thing.

Then he replied with, 'well I once dressed up for ex to fulfil a fantasy of hers, had to down a few shandies before hand though'.

???

OP posts:
tethersend · 13/05/2011 10:34

I agree, he's testing the water. I think he enjoys dressing as a woman and wants to see how you react.

The ex thing is a bit of a red herring; I think he only mentioned her so that if you reacted badly to the thought of him dressed as a woman, she could take the 'blame'.

Out of interest, how did you react?

BluddyMoFo · 13/05/2011 10:35

This reply has been deleted

Message withdrawn at poster's request.

Original poster
OhToBeFree · 13/05/2011 10:35

The issues with ex are to do with kids and legal stuff really....it's all rather complicated but told him we cannot get into a proper realtionship until he's totally settled from all that so I'm being careful, I think.

OP posts:
Original poster
OhToBeFree · 13/05/2011 10:37

I replied with 'wow, that took some courage......well done' and laughed a bit as he was laughing too.....

OP posts:
Original poster
OhToBeFree · 13/05/2011 10:38

Whilst they were going through the divorce his ex tried to knife him, the list goes on and on ........

OP posts:
JeremyVile · 13/05/2011 10:38

I agree, testing the water.

Dont think its a big deal but you might, and really thats what getting to know each other is for - finding out if you are comatible or not.

Original poster
OhToBeFree · 13/05/2011 10:40

I don't actually mind stuff like that but never got into anything 'out of the ordinary'(if there is such thing) with my ex so it was just a bit Shock

OP posts:
JessicaDrew · 13/05/2011 10:41

hope you both have lots of "one size fits all" lingerie
for your weekend away
enjoy Grin

Original poster
OhToBeFree · 13/05/2011 10:45

hehe thanks JD

OP posts:
Thomas1969 · 13/05/2011 11:15

He is a transvestite. Can't admit it to himself so says it was his x's idea. He is testing you to see whether you'll accept it. I guarantee if you do he will just cross-dress more and more and convince you it was your idea.
If you're into it, thats fine just remember, if he cant be honest about what he is now, what will things be like later on if you grow to love him?

madonnawhore · 13/05/2011 11:20

Woah there Thomas with your crystal ball, how can you possibly know that?!

OP, if you're open minded about that stuff then give it a whirl, see if it does anything for you. If it does, great! If it doesn't, then you need to have a chat with your DP and see whether you can find a compromise on both your needs.

LittleHousebytheRiver · 13/05/2011 11:22

My NM has told me he dressed up in his Ex's underwear as a joke to surprise her and she was very cross with him. Not sure if that was because he ruined her best matching bra set or because she was uncomfortable about him cross dressing. I thought it was funny. And offered to buy him some of his own.

Why is it a bad thing to talk about past relationships/sex lives? Surely if you are getting to know someone you want to know what makes them tick, and past hurts are part of that.

Original poster
OhToBeFree · 13/05/2011 11:28

Thanks Madonna and LittleHouse.......Thomas, that was a little suprising to read!

Yes I am open minded and if he asked me to try out a bit of cross dressing, I probably would give it a go Blush but he didn't ask, he was telling me about his past experience with ex.

To be honest, I know it's not for everyone, but I would like us to feel able to talk about stuff that's happened in our pasts, be it good or bad. I just want that sort of relationship now. No secrets so guess I'll just see how it all pans out!

OP posts:
JessicaDrew · 13/05/2011 11:30

you could go to ann summers togther on the weekend away
let him spoil you both with his credit card

madonnawhore · 13/05/2011 11:35

Oh I don't have a blanket ban on talking about exes or anything; obviously you are the sum of your experiences so past relationships are relevant. I just prefer not to know too many details IYSWIM. And I certainly would rather not go on any 'trips down memory lane' with a new partner.

It's all about context.

JessicaDrew · 13/05/2011 11:37

i think the ex in OPs story was just thrown in for good measure
just hope OhToBeFree doesn't end up doing more of the pumping and less of the grinding she hopes for on the weekend away Grin

Gay40 · 13/05/2011 11:41

I wouldn't think too much of it. But if he has got a fancy for it, I'd rather know early on - not that I'd be much bothered anyway, to be honest.
I don't want to know the intimate details of ex-partners, but I like to know what floats the boat of my current arrangement.

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