Sexual Relationships
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I found my brother wearing my clothes and his girlfriend told him to. How should I deal with this?

I came home for the Easter holidays a couple of days ago to my mum and my little brother who's 16. I found him home alone in my room when I came home early from meeting friends, wearing the uniform for my waitressing job. A black blouse and mini-skirt with black tights. I would have confronted him right there but he then began to work on his hair, which he has been growing really long and then used my makeup. From the work he did, he'd definitely done it before and to give him some credit, he really passed for a girl. After that he tried on some of my shoes and locked himself in his room.

I listened outside his room and heard him make a Skype call to his girlfriend who is on holiday in Spain. When she connected, I heard her start gushing over how my brother looked, calling him pretty. My brother kept asking if he had got his makeup and hair right and if she thought that he looked hot. They talked for while and from what I could gather, she was the one who started this and leading him along in it as she asked him to wear a dress next time they Skyped and he agreed. After hearing enough, I left the house and came back later to find him acting like it had never happened.

I don't want to tell my mum as I've literally just told her that I'm dating a girl and she was disappointed and I don't think finding out her youngest son is crossdressing would make the situation better.

My main problem is with his girlfriend who seems to be orchestrating the whole thing. If it was just him trying on my clothes and makeup, I'd sit down and talk with him and give him support but I don't want to encourage a girl's fantasy in using my brother like this in case it gets worse. He's too young for anything like this.

I really don't know what to do, I only want to help my brother and don't want to alienate him but what he's doing with his girlfriend seems wrong and manipulative. Aside from my girlfriend, I have literally no one else to turn to so any genuine advice would be amazing.
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Most Helpful Guys

  • My step sister caught me dressed like a girl and freaked. It was her friend who had me do it. It wasn't thefirst time we role played and I liked it. Stepsister caused a seen got in fight it got out. This was 20 Yeats ago and haven't talked since until 2 months ago when mom passed. My wife now (same girlfriend) apoached my step sister and told her see I was not talking advantage. or using your brother, I loved him then and do now and whispered in her ear and I still make him wear pantiez, he is now. My wife walked of sister cried apologized and we are now talking and her and wife are friends. Step sister has been living here for a month and is now and asked me if I was gay last night. I said I'm far from gay but do what wife wants and will always do anything to please her. I asked her if she still thought I was a fag for dressing clothes for someone I loved ciz she liked it? My sister immediately cried apologized said no. We talked about it for hours aND step sister now understands I do it out of love and respect for woman and to submit. I now know how much superior woman are and I even try to listen and do anything any woman asks. My wife told me to tell her she could stay as long as needed while she was being divorced as long as she knew my wife runs everything and expects me to obey. She also told me to tell her she is superior to me and if she lives with us she has understand and be okay with it. My sister told me that my wife instructed her and she had to admit that she only freaked out back then because I stole her friend who she had a crush on. To end story let be and do what they want, right now I'm sitting here with wife and sister in panties and shirt and so are they. Actually I'm wearing sisters she took off and she in boxers.

  • I mean I don't really see what the problem is with the girlfriend. It's a strange request and all but lots of people do weird things just because it's their SO's fetish.

    you should still just sit down and talk to him alone. if you don't want him using your stuff tell him and find out if he's into crossing or if he's just doing it for his girlfriend. And then if he's just doing it for her, make sure he understands he can say no if your worried she'll try and take it to far.

    • My problem with the girlfriend is that she's controlling him. He may not have started all this if it wasn't for her and I don't want him being used. Like I said, he's being growing his hair long and this only started when he started dating her.

    • no no, I get that, but if he doesn't mind doing it I don't think it's an issue. Which is why I said see if he's into it himself or not. If she's pressuring him into doing it against his will, then it's an issue and you should deff talk about that.

    • I guess I'm just worried about her stringing him along, getting him to do more and radical stuff then dump him when she gets bored. I think maybe getting to know the girlfriend more is best before talking to him directly.

    • Show All

Most Helpful Girls

  • If she's making him do that theirs a chance that she could be getting him to do other stuff maybe even sexual you should deffo speak to him about it but theirs also the chance that he enjoys doing it just a quick question does he wear your underwear aswel because if he does it could be a sign that he enjoys it as he's girlfriend isn't able to see what he's wearing underneath but talk to him and if it really is for him I'd take him shopping and let Him choose what he wants so then you can pretend it's yours and he won't be embarrassed

    • Great answer, I wish my step sister had done that.

    • When I checked the washing hamper, all the clothes he had worn were in there stuffed at the bottom and some of my underwear was in the pile too. Even still, she still could have asked him to show them her after I had left, especially if they're doing sexual stuff as well.

  • If you’re concerned, I would talk to him about it. Be very careful with how you approach it. Emphasize that you know this is an awkward conversation for him to have with his sister, but you’re willing to get through the awkwardness, because you love him and want him to be happy. Tell him that you love him no matter what. Tell him that you’re not going to tell your mom, because it’s not really your place. Tell him that you love and accept him—no matter what he does. ...

    • ... Emphasize that you’re not talking to him because you think that there’s something wrong with him for doing that or you’re disgusted by it. Your main concern is him and what he wants and what’s good for him. Ask him if he actually enjoys doing that, is indifferent to it, or hates it. Tell him that he doesn’t have to answer if he doesn’t want to, but you feel it’s a question he at least needs to ask himself and know the answer to in his own mind. Stress that he needs to be careful if he’s only doing it because his girlfriend likes it, and he has some negative feelings towards it. If he’s making compromises that go against his principles or his personal needs, then it’s not good for him or the relationship. If that’s the case, he’s compromising fundamental principles that are integral to who he is as a person. This isn’t to say that all compromise is bad or anything. However, compromises that go against one’s core beliefs and what makes them who they are as a person are destructive...

    • ... Tell him again that you love him and that you pass no judgment on it—especially if he’s into it. Tell him that, if he wants to talk, you’re here for him. If he doesn’t, you will respect his space.

  • If that was my brother, I would be concerned. Obviously him dressing up as a girl doesn't mean there's anything wrong, but I still wouldn't let it go. He would get an ear full for a while after.

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What Girls & Guys Said

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  • Talk to him about the invasion of privacy, then offer to take him shopping so he can get some clothes, makeup, whatever, and people will just assume it's for you. What does it matter if it was her idea or his? It wouldn't have got that far if he wasn't into it. You said he's 16; that is definitely not too young to be exploring one's sexuality.

    • If it was really what he wanted, I'd be more than happy to go shopping with him but from what I can tell it's all her and he's doing it for her not himself. Sure you start discovering things at 16 but full blown fetishism is not a great place to start.

  • Looks like someone hasn't gotten manhood pounded into him yet... 😒

  • Maybe give her my number and tell him to break up with her:))))) lol

  • Talk to him, ask him how long he's known her, where he met her, who she is. Tell him its definitely not normal and you want to doubke check that she's not using him cause you know how a girl thinks.

  • Don't judge them for having a fetish. Judge them for using your clothes when they could have used others.

  • people like different things so dont make him feel bad but maybe ask him not to wear your work stuff

  • First of all I wouldn't say he's to young to experiment at 16. Many kids I deal with as s counselor start far younger. My big worry would be is he doing it because he wants to or because his girlfriend wants him to. Also at that age if his friends found out it could cause a pretty big emotional issue so he needs to be super careful about this girl having photos or videos of him dressed. But just to reiterate the fact that it is far more common than people realise for teenage boys to wear female underwear lingerie or clothes

  • seems like its all in good fun, i wouldn't worry about too much but keep your eye on him if you're worried

  • Your brother is a faggot (and not as in gay, but being a whim), his girlfriend gets off of having poer over him and both of them violated your privacy.

    You are up for a big talk with him. Considering you turned out a lesbo and I think it's environmental more than anything than some things went wrong in his upbringing as well.

  • You should talk to him about this.

  • Let them do their thing, just ask your brother to buy his own clothes and makeup

  • You need to talk to your brother.
    She is turning him into a hardcore sissy cuck. Tell him that he needs to be a man and dump her. She probably gets off on fucking guys in spain while her boyfriend is dressed like a girl. Do what you must to save him.

  • Id say talk to him and yell him you support it but then tell him if he wants to be a crossdresser he needs to get his own clothes and make up i wish i had a sister who would help me crossdress and i dont think his girlfriend is manipulating him she probably told him she likes that but if he didn't want to do it he wouldn't

  • some people have that kind of fetish.

    • by the way your brother's girlfriend sounds like a bitch. she could also be making fun of him like that. either way, do something that they both break up

  • Sit down and talk to your brother. Ask him if this What he likes and wants to continue. I know it was and is a shook but just support him. What ever his decision respect it. It takes a lot for you and him to be open to all of this.

  • I wish I had a sister like that.. one of the fetishes I have is playing dressing up and wearing cute girly outfits... There's definitely a difference between men's and women's clothes women's clothes feel sexy to wear.. and knowing it turns me on makes it even better.. now if you want to help him explore further you should arrange a playdate to see where it goes

  • They could be messing around but get angry at them for using your clothes, if his girlfriend really wants him to do this she should've given her clothes

  • he must have a fantasy

  • He needs an older brother in this situation to take the piss out of him.
    If you try to advise his it won't work.

  • I guess he can like what he wants but I recommend talking to him. Even if it's just to set boundaries around your stuff

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