How can I be supportive of my boyfriends strange fetish?

My love and I have been together for quite sometime and I love him dearly. This is the man I am spending my life with. However, I recently discovered he has a weird fetish for “Lady boys” and cross dressing. He has always liked when I wear pantyhose and thigh highs during sex (the fabric feels good to him and turns him on) but I found out that when I am gone he has secretly been wearing my pantyhose and masterbating while he looks up videos of transvestites. Its not that I am embarrassed by it or that it upsets me (I always knew he was a little weirdo :) ) but I’m not sure what to think. We’ve begun experimenting in the bedroom to accomodate this fetish and (to my surprise!) I’ve been enjoying everything we do. The only thing is, he’s been pushing me to let him cross dress for me and I really dont think I’m ready for that. It confuses me to think of him cross dressing because he says he doesnt like guys, only women, and that he loves me (as a woman and for being a woman) but if that is so then why does he want to dress like a lady? Everything we have tried so far I was skeptical about but ended up liking (I like things a little freaky) but I really dont like the idea of him cross dressing. Even though we’ve been experimenting and he wears my pantyhose I’ve still been able to think of him as manly and sexy, but the idea of him dressed as a woman is about as feminine as you can get and it turns me off. (And its not just pink and frillies he wants to wear, he wants the pantyhose, dress, heels, everything) Any advice as to how we can find a way for him to cross dress and still keep his manliness about him?

Answer #1

this is kinds OK occasionally, its better to let him know that he’s the person which is turning you ON not what he’s wearing. let him know that you don’t like it.

Answer #2

It’s good this is out in the open instead of being hit with it 10 years into your marrage! Sounds like he is very lucky to have such a cool and fun sweetie in his life! Knowing some about fetish if I had to guess “and I don’t know this” he will keep going forward as long as you are cool with it. If it were just a pantyhose/underwear fetish he would be more than satisfied with where you two are sexually. But sounds like every time he gets you to one point he moves to something forward to push you further. If I had to guess, if you go to the next level of full drag the next step will be something related to him looking at TV’s, ie. asking you to wear a strap-on ect.. I don’t know this, just be aware that it’s possible with this type of fetish. I’m very lucky like he is to have a babe that’s up with my hose/foot/high heel fetish and we’ve been married 20+ years! I wish you the best!

More Like This
Advisor

Sex

Sex education, Intimacy, Relationship advice