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My Crossdressing Story
It started when I was pretty young. I want to say around 2nd grade. I was at my Aunt's house for my cousin's birthday, and I was downstairs playing video games and stuff. At one point, some other kid saw this pink suitcase and brought it out. Inside was a bunch of dresses and costumes that belonged to my cousin. All of the kids, even the boys and of course myself decided to dress up. I had never even thought of the idea of wearing girls clothing until that night, but I was just following the crowd. I think I ended up wearing this Disney princess dress. Everyone was wearing their own outfit the rest of the evening. It was a weird night, needless to say. Eventually everyone took their stuff off and got back to their original clothes when it came time to go home. This was the night that started it all! I continued to sneak downstairs and wear some of the other clothes from that pink suitcase whenever I came to visit after that. I did kind of enjoy it.
About a year later, I was in our own basement. I was tossing some darts at a dart board. That's a safe activity for a 3rd grader, right? Anyway, I saw Inside this bag was a pink shirt that came from my sister. I suddenly got the thought of what it would be like to wear it! I ignored it at first, but after a few days, I remembered that night at my cousin's birthday, and I wanted to try it again! I caved and put on the pink shirt! It felt pretty good, and I continued to wear it for a bit. I almost got caught when my mom called my name at the top of the stairs. Thankfully there were walls around them, so she couldn't see me unless she actually came down. I just responded like normal, and continued on
After doing this a few times, I saw some of the other shirts inside that bag. All of them from my sister! I brought the bag over to the crawlspace, and climbed inside. I blocked the entrance with a piece of plywood board. That gave me extra privacy to wear some of the other shirts. I wore them all at once, and then tried some of my favorite by themselves! Again I really enjoyed it, and eventually I decided to take one up to my room by wearing it under my normal shirt. I almost got caught again because I ran into my mom heading into my room. One awkward conversation later and I was in! I kept it hidden in the bottom drawer of my desk, and started wearing it to bed. That was the only time I could actually wear it in private for an extended period. I started bringing up a couple of others that I liked as well! This continued on for a bit, but then there came a point where I stopped doing it. There were a couple of years after that where I never put on a girl's shirt.
We'll skip to somewhere around middle school. I remembered my time wearing those shirts, and I suddenly started doing it again! This time though, I branched out more. I started wearing my older sister's and my mom's clothes when everyone was out of the house! I even started wearing some of the dresses too inside of just girly shirts! I definitely found that I enjoyed the dresses more, and I started wearing their clothes to bed whenever they stayed the night somewhere! Middle school was of course around the time that I hit puberty, so you can guess where that took me. My sister had some amazing dresses and outfits that I really enjoyed! I even snuck in after school some days to wear her stuff for a bit, since I know she wouldn't be home right away. It felt amazing!
Once I turned 18, I already had a job, and I started getting some of my own clothes. Mostly online, but I did kind of like the rush of picking up a dress or something in person. I always did my best to make it seem like I was buying it for someone else! There were a few times where I bought a dress from a store, and I brought it into the bathroom stall so I could try it on! I would then put on my normal clothes over it, and just walk out while having it on underneath! My collection got kind of big, so I started hiding them under my mattress instead. I continued to wear these girly clothes to bed nearly every night!
Today I'm a little bit older still, and I haven't stopped! I'm just really into the pink and cute stuff. Especially with skater dresses! The more cute and girly it is, the more I want to wear it! I'm still a straight guy who likes women, but I can't get enough of this crossdressing thing! I love it so much
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I wear my older sister's undies and twirl around feeling so girly
Similar story here. Used to wish I could wear dresses and stuff. A couple of times at school I was in plays where I had to wear tights. One time I was a tree and had to wear green tights and a brown tunic which was basically a mini dress and a second pair of green tights cut in two and put over each arm. I used to wear the tights on my legs and the tunic around home saying I was practising. Then for ages after I'd wear the tights under long pants.
Fast forward until I was 15 with raging hormones and there was a mannequin with a leotard on it in the shops I walked past on my way home from school. I started taking the train to places where no one would know me and looking. Finally found another shop. Took a deep breath and went in and bought one.
Got home and would wear it in bed. Started masturbating in it. I'd wipe it clean but not wash it. I kept it under the mattress. Huge feelings of guilt. Sometimes I'd try to stop mast eating but that would only last one to two weeks before I'd give in. One day while I was at school, mom decided to turn the mattress over. She found it. Washed it. Folded it and put it under my pillow with my pyjamas and a pair of plastic pants.
I was mortified when I went to get ready for bed. For ages I lay in bed. She came in and sat on my bed and said boys have this pressure and that was perfectly normal. She said the plastic pants would help contain the mess and that I should just wear them every night as men get aroused in their sleep.
It ** keeping it hidden and the fear of being caught. I dream of the day when boys can wear dresses, skirts, tights and girls clothes.