My boyfriend likes wearing women's bras and knickers and watches shemale p*rn. Why does he like it?

My 24yr old boyfriend & I (23) have been together since Feb2012. At the start of the relationship he told me that he liked to wear women's underwear & wanted to wear it during sex. At the time I felt shocked & confused, but as I'm an open minded person I said that was fine. This happened once during sex (I felt so grossed out during it) & he wore my underwear often. This was fine to begin with but overtime I became less understanding & wanted it to stop as I was feeling more & more uncomfortable about the whole situation. It was starting to make me feel angry & I was feeling less turned on by him. He always said that it was for comfort & that the panties "hold everything in right" - but then my question to him was, what about the bra, you don't have boobs...& also you asked if you could wear it during sex? He always denied that it turned him on. We then got into a major argument about it (I can't remember why) but then he promised to stop. This was great until he brought it up a few months later, I tried to be on board with it again but I found it so difficult, he would wear my underwear everyday & it disturbed me that I wanted to wear some particularly sexy knickers/thongs for him but he would be wearing them himself! He then suggested going out to buy his own, he did this for a while but it still really freaked me out, so we talked but got in an argument about it because he thought I was being unreasonable. He again said he wouldn't do it again but since then, every time we have had an argument, he has asked if he can wear women's underwear, claiming that he only ever said it to piss me off cos he knew I hated it. Very recently in Sept2013, our relationship was on the line due to a whole host of other issues. He said he wouldn't leave me if I could do 3 things, one of them being to be OK with him wearing women's underwear (both bras & pants) & to allow him to do it. As I didn't want him to go I said "yes" knowing in my heart I could never be OK with it, I just told him if he is going to do that I don't want to know about it & I don't want to see him wearing it. He asked if he could wear mine & I told him to get his own. He said he wants to do it so that he can get over his want to wear it & so that we can continue our relationship as normal. I found out that he wears the undies everyday and he wears the bras the moment he gets time too (when I'm not around). I've told him I can't really be close to him while he is doing this but that doesn't seem to bother him, it's like his desire to wear the underwear over-rules being close to me. I also found out that he likes to watch shemale p*rn & that has made me even more confused! I'm confused as to why he can't tell me the truth about why he likes it? If it is for comfort, why does he choose the sexier undies over plain 1s? Why does he like watching shemale p*rn? Is he gay? Does he want to be a woman? Is he with me because he thinks that I look like a man? Will he ever TRULY "get over" it?
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Most Helpful Guys

  • Being a crossdreser myself I can tell you it took a lot for him to even tell you about his hobby, let alone actually wearing women's undies in front of you. He holds a great amount of trust and faith in you, as well as being very comfortable with you.

    I have "stopped" on many occasions. Even going as far as throwing away all the lingerie I had acquired at the time. And after a short while, it returns, and I find myself in a bra and panty again. There is something very comforting about having that bra wrapped around my chest and the panties holding everything just right. I'm even wearing a bra and panty right now as I write this. It's quite the relaxing feeling to be wearing women's lingerie. Being a crossdresser is more of a "lifestyle" than a hobby or fetish. So it's not that his lingerie wearing is more important than you, it's just that it's as equally important as you.

    He's lucky to have you and your lucky to have him. Go ahead and take him out shopping with you. Make it a fun thing. He can help you find what looks best and works best for you, and you can do the same with him. And that way you might just have an extra bra or panty to wear on that special occasion when one of yours won't do.

  • Attraction is involuntary, something attracts you or it doesn't, it's not a conscious choice. Basically, he likes it because he likes it, has nothing to do with you.

    Obviously this guy is not for you. Stop wasting your time on him, you have no future together, so cut your losses.

    Go find a new man, every second you spend with this guy is a complete and total waste of your time.

Most Helpful Girls

  • Do you love him? That's the only question you need ask. If you do, then the mouth-breather concepts that paint our culture needn't distract you from the most important attributes. Talk to him. Listen. Open up yourself. Enjoy your life and your relationships, even if parts of it color outside the lines.

  • Its a tricky one and lots of this about. My friends know men that like pantys. In bed with you with sex is a worry. I like sniffing my girlfriends and been caught twice. I wouldn't mind if I couldn't see and I suppose he could cum in my pantys after sex but mmmm selfish with t eother

  • Ask him. And listen. S/He/s human. As are you. Open your heart and mind a little bit.

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What Girls & Guys Said

2 9
  • And again "You're still with him why?

  • He's getting off on it.

  • I don't think it really matters why he's doing it. I don't think he's gay because he wouldn't be having sex with you. The problem is that he has a few fetishes that you are not comfortable with. Your relationship will not work for this reason. It sounds like you need to accept the fact that the two of you are not compatible and move on.

    • I completely agree.

  • Most men who like to dress in women's clothing AND like watching "shemale" porn are imagining themselves as the "shemale" they are watching. If the porn he is watching depicts a trans woman with a cis woman then he likely sees himself in a somewhat lesbian relationship with you. If he is watching porn that depicts a trans woman with men then he is most likely bisexual. In any case he may very well be transsexual at least between the ears. One thing is likely, he will not stop ever. If you can't live with his cross dressing then you probably should break up with him.

  • I am also in same skin as you boyfriend, he is normal. Please help him with fantasy

  • Because he is a weirdo.

  • I'm impressed with how fast this user became "no longer a member." Less than 7 minutes from when this question was answered.

    Why don't they delete the question then?

  • It's hot

  • One of my exes wanted me to wear her clothes... I wasn’t expecting it and I didn’t do it... I knew her mom was a gay rights activist and a lesbian so in my mind I thought she would bring another girl into the fun but... nah. I’m more open minded now but that one didn’t just did not work out for other reasons. I moved on... met someone else and got married and now have 3 kids and no time for sex because of everything else that needs doing every single day... so have fun while it lasts and do whatever you want... sounds like if you surprise him with a strap on... you would be his dream come true. And if that’s the case... he needs to become your dream come true for you as well, perhaps in other ways, to be more compatible... if he doesn’t... buh bye.

    Relationships are both give and take and share and put each other first... it takes effort.

  • I'm. slowly getting gayer and gayer it started when I found a pair of pink knickers now I'm likw your boyfriend

  • Maybe he wants to be a she male.