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female
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anonymous
writes: I have been with my boyfriend now for 7 months, it has been great and he is a very caring and fun guy, we fell in love and he is moving in with me next month. I was very excited about this until I one day I discovered whilst looking up an item of furniture he was selling on the internet, that he had bought and sold some items that I found rather strange, they were mainly very high heeled shoes in a size 8 (his shoe size!!!) and also discovered that he has bought women’s clothing (yes it could have been for a past girlfriend) but I also saw items he bought that could have possibly been wigs, as the person he bought the item from mainly sold wigs from his internet store, I have since discovered he is currently selling 3 more pairs of high heels in a size 8 that have been slightly worn?? To me the only explanation is that he was or still is a cross dresser. I am so concerned, I have read up a little about it and I know most cross dressers don’t necessarily end up wanting a sex change but in some cases they do, I don’t want to marry someone who may one day turn round and say he wants surgery to be a woman or discover he is gay!!! I don’t know how to approach him about it and part of me doesn’t want to hear the truth, he has never given me reason to be suspicious until I found all this stuff on the net. Please help, Thanks!
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reader, anonymous, writes (1 March 2007): This is verified as being by the original poster of the questionThanks again for your advice, yes I will talk to him about it and will approach him in a kind manner. I need to know how far into all of this he is and all his thoughts before I get too involved. I can handle it if its a past phase but if I am honest I dont think I could handle it seeing him all dressed up like a women!
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female
reader, TELLULAH  +, writes (1 March 2007):
 Hi,
It tells me he dosnt want you to know, and is really embarassed. You really do need to talk to him, and tell him what you know. It does sound to me like your right about him, but its not the end of the world.
When I first started out with my B/F, his ex sent a bag of clothes to us. Well i nearly died when i opened it up, there were things that i never thought i would see. Bondage gear, strange underwear(hers) and high heels in his size.
I was really shocked to say the least. Apparantly he used to wear some of this gear to the rocky horror show.
But we talked about it, and he threw it all out. I know his past and I shared a few secrets of my past. And we are really very happy.
If he wanted to dress up again I dont mind, its only dressing up after all.
But you must get things out in the open.
I hope you get on ok and sort it all out. XX
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reader, anonymous, writes (28 February 2007): This is verified as being by the original poster of the questionThanks for the advice. My gut feeling is telling me its not just that, I havent found any evidence in his house to back this up but the fact that he has all these shoes in his size and that have been worn just leads me to thinking he wears them. plus apart from the shoes on ebay he has added a couple of items I knew he was putting on there, but when I offered to check the bidding activity as he has no internet at work, he lied and said he had not put them on yet, so what does that say??
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reader, anonymous, writes (28 February 2007): This is verified as being by the original poster of the questionThanks for the advice, I know I have to talk to him about it, I am just so nervous bringing it up. It is possible it could be a phase because as far as I can make out the period of time he purchased this stuff was only over the space of a year. I dont have anything against cross dressers but personally I would not feel comfortable with him doing it around me.
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male
reader, kenny +, writes (28 February 2007):
 Lets not get carried away here, you may be jumping the gun a little.
It could be something as innocent as he has found something that sell's well on what i assume is something like Ebay. He could be just buying and selling items of clothing, many people do it.
Have you ever found any evidence that he has actually been wearing any of this gear?.
If you have real concerns that he is cross dressing, sit him down and ask him outright, get comfortable maybe pour a glass of wine for you both and ask him why he has womans clothes and shoes in his possession.
Good luck x
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female
reader, TELLULAH +, writes (28 February 2007):
Wow, thats a tricky situation,
You must do the only thing you can, and talk to him about it. Its the only way you will find out.
My guess is though, he wont admit it for a while (if he is). You will have to be very kind and understanding about this, and try not to get upset with him.
Its possible he may have gone through a bit of a faze, and was just experimenting. So dont automatically think the worse.
But you should deffinatly try to deal with this, sooner rather than later.
Would it bother you if he is cross dressing, but has no intention of being gay or having a sex change.
Could you live like that, because believe me it becomes a lot less shocking after you see it a few times. It really wouldnt bother me, as long as it was just at home.
It depends on your views really.
Be kind though, he is bound to be embarassed XX
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