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I Caught My Brother Wearing My Clothes

A couple nights ago, I came home from volleyball (I'm a senior) and my parents were at dinner for some thing for my dad's work. I knew my brother was home but I thought he was doing his homework or something so I ate downstairs and didn't announce myself when I got home.
Long story short, I walked upstairs and saw my brother (sophmore) dressed head-to-toe in my skirt, my top, and wearing makeup. He stared at me for a little bit while I sat there staring. I started laughing and found it hilarious (and kinda flattering?) but I obviously had a lot more to think about.
So I forced him to talk about it and yeah.. He full on wore my clothes for a long time. He wore my panties, and that is super gross so I told him this had to stop... Well at least some of it. I told him the following things: His makeup wasn't awful but if he wanted to do makeup, he could just ask me. He shouldn't wear my clean clothes and then put them back in my closet, cause I wouldn't want to wear them anymore. And that he needed to stop wearing my underwear completely.
After talking until my parents came home, I decided not to tell them and my brother begged me to keep it a secret.
So here's what I'm thinking... I really want to treat him and take him to the mall one day, but I don't know where he would "hide" this stuff or if he would be too embarrassed. He's shy about it but I can tell he enjoys it, he's not gay but kinda acts like a girl. So yeah that's my rant about my brother.
Jessie407 · 70-79, M
As a crossdresser myself, I can tell you that the feminine underthings are the biggest attraction. He is NOT going to be able to just STOP wearing them. The best thing you can do if he is embarrassed about it, is to get money from him & buy him some panties, bras, pantyhose & slips in his size & help hide them for him. The best place, obviously, would be among your things but with a special mark so that you both know they are his. That way he will be sure to leave your lingerie alone.
My sister hid my things in with her clothes until she moved out. Then the items got hidden in the attic ... They were gone when I returned home from the Army!! SOMEBODY found them & either discarded them or took them for themself!
sally1981 · 41-45, F
Many Brother's wear their Sisters and Mother' s knickers and nighties in secret until they get caught.
Jessie407 · 70-79, M
@sally1981 I did.
Although, my sister would invite me in to her slumber parties & the girls would dress me up in lingerie & nighties.
Many times they would take off the panties they were wearing & give them to me as a gift for being such a good sport. Little did they know (or maybe they did) that I would wear all them to bed one pair over top of others in layers. The sensation was FANTASTIC!!! I would never dare cum in them, I wanted them with their scent on them for the next time!
sally1981 · 41-45, F
@Jessie407 Great reply on knickers and Men wearing them.
Sally💋
Jessie407 · 70-79, M
@sally1981 You see, they thought they were forcing me to dress in their clothes! I can only guess that they figured it out that I was a crossdresser from a very early age. I collected panties, bras, slips & pantyhose for years!
My sister only got mad when I had taken too many of her things at any one time.
She even helped me with my long hair & make-up a couple of times.
DiegoWolfe · 36-40
Take him to the mall and also buy a cheap duffle or backpack to keep his stuff and store it in your room, your parents wont think twice of girl clothes in your room, and many straight men dress in girls clothes for comfort so good on you for accepting him so fully
Highskirt · 56-60, M
Treat him to clothes you would wear and give them to him .he must respect you and your boundaries
ninalanyon · 61-69, T
Couldn't he hide his stuff in your room?
Quimliqer · 70-79, M
Your hearts in the right place, but the dilemma would be keeping it secret.
Jessie407 · 70-79, M
@Quimliqer My sister hid my lingerie in her room. I could go in & take what I wanted of mine & even a few pieces of hers for an evening of enjoyment. The only rule was that I couldn't soil her things.
Our parents never caught on.
joe438 · 61-69, M
He would be very lucky indeed if you were a supportive sister. My mother caught me in my sister's clothes and my sister was none too happy about it. I of course agreed to stop, but I didn't. After a bit, my sister began spanking me for my continuing - but honestly, I loved the attention even if it meant having trouble sitting.

If my sister had simply asked me to stop, let me wear her old clothes without yelling at me, etc., I would have been floating on a cloud. It all worked out and we're the best of friends now. I felt really bad at putting her through that.
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morbidraccoon · 31-35, M
SW-User
Boy oh boy. You made an account on here just to say that!
I am surprised you are so supportive of this. If your brother is becoming a man, he has no business dressing up as a female in any woman clothes.
laurennnn23 · 22-25, F
@GundamWing: wtf it's not a fetish?
@laurennnn23: If you talk about it on this site it might as well be. Excuse me if it isn't. But all in all I don't agree with your choices.
Jessie407 · 70-79, M
@leavingthissiteforgood10 Do you wear slacks or jeans? If so, then you are a crossdresser yourself. Is it a fetish for you? No, society accepts women embracing their male side, but closed-minded people like you keep men from embracing their feminine side,
If you expect a man to be sensitive to your feelings, then you are expecting him to embrace a part of his feminine side.
Our non-dominant side manifests in ways we often don't want, or can control.
UserNameSW · 46-50, M
Glad he has you to support him
Late comment here, but you handled it the right way. Crossdressers can control their behavior, but not the desire.

He needs his own clothes to wear. Maybe you can "store" his stuff amongst you own clothes?
Well he could hide it in your room 🤔 but yeag sharing underwear is nasty

 
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