Wore My Mom's Clothes As A Kid.

Like the poster a few posts down, I pretended to be sick sometimes when I was a kid so I could stay home from school and wear feminine clothes. In my case it was my mom's clothes. She was a single working mom, and in those days, it wasn't as big a deal to leave a kid alone as long as he wasn't too young or immature. At the age I was, her clothes fit me perfectly. I'd put on her make-up and lipstick and wear one of her short skirts or a pair of her hot pants, with panties and pantyhose, heels, and a bandeau tube top. She'd call me a few times during the day to see how I was feeling. Little did she know that as I was talking to her, I had my hand down her panties rubbing myself off, and sometimes I'd come as we talked, doing my best to hide the ecstasy in my voice. I kept from staining her panties by wearing a condom I had filched from her purse (she didn't have a steady boyfriend but she dated sometimes). I tried to make sure I didn't damage her clothes.

One day she came home early and caught me. She was a wonderful, open-minded mom however, and did her best to hide her shock. The only thing that miffed her a little was that I'd snagged her pantyhose on something and put a run in them. Lol, she also told me I didn't know shit about putting on make up, and she wondered what was the use of wearing a tube top when I had a flat chest. After some pretty calm discussion considering the situation, she told me I needed to quit malingering and go to school, and if I wanted to dress I could do it when I got home.

The next night I got mom's make up kit and sat in front of the mirror. When I finished, she just glared at me and said, "My god, Danny, you look like Bozo's girlfriend. If you're going to do this, learn to do it right." Then she sat down beside me and taught me how to apply cosmetics step by step. In time she showed me how to cut and style my hair in a way that looked quite girlish while at home, but could be combed out to look boyish enough for school. It took a lot of pleading, but she agreed to pierce my ears when summer came (she'd worked in a boutique before and knew how to do it safely). She let me borrow some of her earrings and other j*welry, and she let me have some of her clothes to keep, but she teased me that I only seemed to want her "sluttiest" items. It was so much fun to be able to just sit around and do my homework while wearing mom's strappy heels, daisy dukes, and a sexy bandeau top. I used to love looking at my flat bare stomach and legs in the mirror. One time on impulse I even asked mom if she thought I had nice legs. She said, "They're nice, your calves and thighs are sorta curvy I guess" and didn't say anything else. I don't think she wanted to encourage me too much, but she didn't want to discourage me either. She wanted me to be happy, and I'll always be grateful for that. I became so proud of how I looked when dressed that I asked mom to take some polariods of me, for our eyes only, and she finally agreed.


I knew the question would probably be coming, and sure enough she asked, non-judgmentally, if I was gay. I said no, I didn't think so, I always fantasized about girls. I also told her I didn't want to be a girl full time, but at the same time, I didn't want to stop dressing. I told her truthfully that I didn't have a need to dress in public, but I had a feminine side I needed to express at home. She said she'd been reading on these subjects and she told me I was probably a hetero transvestite and that was ok. She didn't want me to be ashamed. I said I wasn't, but I didn't want anyone else to know.

When I grew out of mom's clothes she bought me my own. Whatever I wanted, no matter how skimpy, slutty, or mismatched, she bought them. She even got to treating me like a daughter when I was dressed, calling me cutie and pumpkin and things like that. I asked her to call me Danielle, a feminine form of my name, and sometimes she would but sometimes she'd forget.

Puberty took a really long time for me to completely go through, but when I did, I was classically masculine. I slowly dressed less and less. I could never give it up completely though, and I still dress now and then. Luckily, my gorgeous wife of 25 years understands. We've got a 22 year old daughter and she already knew I dressed, but I recently showed her some of the old polaroids mom took. She thought they were fascinating and said, "Dad, you made a really hot girl. You were cuter than I was at that age!" My incredible mom's still alive and well, and she has regaled my daughter with tales of those days. I've had a good life, and I hope there's a lot more to come.