• 5 years ago
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I am a (23) yr old man that enjoys wearing women’s underwear. I grew up with a younger sister. She’s four years younger than me. Me and my sister have separate rooms. Around when I was 18, I was running late and groggy while getting ready for school. I was scrambling to get my clothes out of the dryer and realized my sister put her clothes with mine for the laundry load. I was fine with putting on my button up shirt and socks, but I grabbed what I thought were black boxers were really hip huggers. The underwear felt oddly slick and smooth. It hugged my hips in a way that my boxers didn’t. I just went with it, put my jeans on and headed out the door.

The entire day at school from the bus ride, through the duration of my classes, and especially gym warm ups, I just felt so… s***. It was like some taboo turn on. It was an accident that just ended up changing my outlook (and underwear ha) about men and women’s clothing. I managed to get my sis’ p****** washed and back into her pile without anyone noticing.

After that incident (fast forward like a year and a half to when I turned 20), I still thought about what that old feeling was like when I one day got ready for college. I don’t dorm as I’m not that far away and it’s more affordable. My sister does and sometimes she comes home for holidays and other special occasions. I decided to take a pair of satin white p****** and a matching s*** bralette from her room. I go into my room, look in the mirror and just adore the way it feels and the way I looked in that moment. (I’m no beauty pageant model, but trust me, in that moment I felt like one).

I felt guilty taking from my sister like that, so when she came home from college on winter break, I asked to talk to her privately in her room and I explained to her my fiasco from high school and how it got me into this urge. (I left out the parts you can guess that I did while wearing the s*** stuff). She didn’t seem to care or be supportive either. Just kind of put off by the thought I wore it, but I told her I washed it and put the ensemble where I got it. She went to her closet after processing everything I dumped on her lap. She did something I didn’t expect. She went to her closet and gave me the pair of white satin p****** and matching bra. I asked her why she’s giving this to me and if she’s not the least bit freaked out. She gives me a hug and says “I don’t care. I haven’t worn them once. You can keep them.” I was overcome with so much relief and happiness that I cried and hugged her back. Ever since then, I felt more comfortable wearing women’s clothing in the house.

So, cut to now, and I still have this urge to just put on a bra, p****** and even some garters from time to time underneath my clothes when I go out. I’ve amassed a considerable collection since then (I bought these myself, no more taking from my sister). I store my prized stuff in my sister’s room and my casual stuff in mine. She has agreed to cover for me when she can. It doesn’t bother her. It’s just simple as “Yeah, I ordered that online” or “I used bro’s credit card for that” if packages ever came up in my name. She doesn’t ask about it, she doesn’t even threaten to tell anyone.

The part that makes this bittersweet is just, even though my sisters might be supportive (for lack of a better word) I carry this guilt of shame if our parents were to find out or my friends. My sister’s covered for me when our mother would often find other s*** clothing mixed in the wash “accidentally”. There was one day where she caught me u********* and was wondering why I had a white satin p**** on. And I covered it up by saying my sister let me borrow it since I didn’t have clean underwear for school that morning. It worked, but my mother said “Okay, well, just don’t do that again.” My heart sank. It’s not like I committed a sin or some heinous crime. But it sure felt like I had. And I tried my best to get over this urge by not buying as much lingerie or dresses. But once I wore something to the point that I got desensitized to it, I ended up just buying something more risque. It made trying to hide this secret all the more stressful. I want to point out that I still identify as straight, but whenever I close the door of my room and look at myself in the mirror all sexied up (yeah that’s how I describe it) I just end up feeling like wanting to be more like a woman. Don’t get me wrong, I don’t hate being a man. I’m fine with what I was born with and how I’m treated. I still feel like a guy and still like to date women like any other straight guy. It’s just when I put on those clothes, sometimes I fantasize about sucking a guy off, and just feeling empowered like the clothes I wear make me feel. It’s such a conflicting feeling with what all the societal messages and expectations tell me (I’m talking about being considered gay or bisexual). I don’t get turned on by men. At most, men that convincingly appear like women. I’m still attracted to the female form. Right now, I’m just dumping 4 years worth of shame, guilt and uncertainty.

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