Why does my boyfriend wear my underwear and masturbate?

I've found my panties in his drawer a couple times & I talked to him about it (a short, awkward conversation). We have lived together for 5 years and our sex life is great. We're both pretty sexual I guess and watch a lot of porn, and he's not a cross dresser or anything. It doesn't gross me out or bother me, I just want to know why. He was too embarrassed to answer detailed questions about it. Like, does he want to feel feminine or is it the taboo or does he just like how big his d*** looks in them? I just want to know what turns him on!
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Most Helpful Girl

  • I have a lot of experience with this.First of all,I will tell you that I do enjoy seeing a guy dress in drag,and have enjoyed transforming many guys.I will also tell you that,this is very common,more so than you could ever imagine.It's also perfectly fine.Who's he hurting,right?It's not like it's beating women,or disgusting kiddie porn,or anything.So ,he likes feminine clothing,so do I!If you do too,now you've both got something in common.Go shopping together!It's normal for the guy to be very embarrassed about this,especially at first,but keep telling him,that you like the idea,and want to explore it with him,help him,and both of you will have lots of good times together.It will get easier. I've gotten lots of guys,who were very reluctant ,at first,to eventually let me dress them fully,do their makeup and wig,and actually take them out shopping or to a club.Smoe of my girlfriends even help out and go along.It's a lot of fun!

    • I don't have any problem with it as long as our relationship & sex life is good. I just get really interested in what turns him on & usually they wind up being big turn ons for me too once I get into it. I just have to figure out what he likes about it & stuff before I'd feel confident to bring it into our sex life together.

    • I understand.It's a little different,if you're just finding these things out,for the first time,because it seems so out of charachter,for most men,but it doesn't mean he's still not a great guy,or doesn't love you.

    • Wow... she catches him with her panties and then feminizes him? Sounds like something out of Literotica!

    • Show All

Most Helpful Guys

  • one thing to try is to tie him up and blondfold him and put ur panties onto him and have fun like that and see if he gets more aroused by it. or else make a bet with him and if he loses he has to wear them for u...it give him no choice but to do it...and while he is wearing them he may become more honest about what he likes...good luck with it and keep having fun.

  • The answer is totally with him, but if you really want to know, say so: "I'm totally down with you beating off in my undies. I know you don't like to talk about it, but I'm just curious what's in your head when you do it."

    He may just tell you. Or not.

    • I tried to let him know I would be into it if he wanted me to be. I think he got that "I can't believe I got caught" feeling & clammed up. Once I asked him to put them on so I could see & he said he wasn't in the mood for it, but he didn't seem too freaked out. I like to hear about the naughty things he does by himself, but that might be a private pleasure that he wants to keep private.

    • It might be. As long as he keeps getting the message that you're cool with it, it'll turn out for the best.

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What Girls & Guys Said

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  • umm I know I tried on my step sister... and it was amazing! not in a gay way like crossdressing, but just the knowledge that your wearing them, the look, the feel, and just there's a feeling about having them on that just turns you on soo much. at least for me

  • i don't see anything wrong iwth it..

    to each their own I say

  • All I wear is panties and thongs girls underwear r more comfy thenmebs