My First (?) Time Crossdressing

[Mindy Jean]

It began one Halloween when I was still in grade school. My mom and I went looking for a costume for me at the local Five and Dime. I found a mask of a little girl's face and as I tried it on, I jokingly called out to my mom. She turned around to look and when she saw me, she laughed and said she thought it would be cute for me to go dressed as a little girl this year. She even said she could make an outfit for me to go with it. She often sewed tank tops and such for my brothers and me. It was the late 60's and it seemed we always had time for things like that. (Being the youngest of three boys, I think my mom had a desire for me to have been born a girl....)

After we got home, mom started sewing my costume for me. A couple of days, she had me try it on. It was a short skirt that was about four inches above my knees and a vest with a single button in the front, with both pieces made out of a light brown corduroy. She had bought a white shirt to go under the vest, white knee high socks and black penny loafers to complete the outfit. I wore a pair of shorts under the skirt. (Looking back, it's a shame she didn't buy me some cute panties and a training bra, but I'm sure I would have refused to wear them.) She told me to go into the laundry room to try the outfit on and when I came out all dressed up, we laughed about my costume and what a joke it would be for me to wear it this year.

Halloween day, I got all dressed up and got on the school bus. Having always been a jokester and very out going, I played the role up to full hilt on the way to school.

Once at school, it was a pretty normal day, except for the fact that we were all dressed in our costumes. At one point in the day, we had an assembly in the gym, where all of the kids got to parade past the principal, teachers and the staff and show off our costumes. As I passed the principal, sitting in his chair, I stopped long enough to pinch him on his cheek and say, "Hi, Cutie," before walking away. (He later ended up molested me and as we all found out, several other boys at school... But that's another story!)

After that day, I can't say I was hooked on cross-dressing, (it was Grade School, after all....) although I can say that the feeling of being dressed as a girl did have a certain effect on me. I don't think it was sexual.... I don't think I even knew about sex at that point. I think the feeling was more from the attention I got that day. Everyone wants to fit in, to be accepted, to even be the class clown if that's what it takes!

That was my first experience with cross dressing and my last for a couple more years. Although I had a younger sister and both her and mom's dressers were full of lingerie, neither the thought nor the desire to try them on ever entered my mind. (As I think about this now, this may not be true! And this may have not been my "first" time, either!)

It all started again for me one Christmas after I hit puberty. Every year, we would go to my aunt and uncle's house to celebrate with them. All of the kids would usually go down to the basement to play, while the adults talked upstairs.

All of my cousins were girls, with some them younger and some older than me. While I was downstairs with two of my cousins, the older of the two, who was a couple of years older than my 13 or 14 years, turned on some music, dimmed down the lights and asked me to dance with her. Of course, at that age, I thought she was beautiful and since I was just finding out what these creatures were all about, it didn't take much persuading from her to get me to dance. As we danced, she had an way of bringing her thigh up between my legs and rubbing me in a certain place. She was an expert tease and although the thought of (sex) was on my mind, of course it wasn't to be!

After everyone was called to dinner, my still horny mind decided to get some revenge. I went into the laundry room and found a pair of panties and a bra. It really didn't matter if they were her's, I had my reward! I quickly stuffed them down my pants and joined the rest of them upstairs for dinner.

After I got home, I didn't know what to do with my new found treasure, so I hid the panties and bra under my mattress. Most of my sex life consisted of my new found joy of masturbation. I discovered that my pillow could be my temporary lover and soon found the pleasure of stroking myself against "her". It didn't take me long to figure out that I could dress my "girlfriend" in "her" new panties and bra. One thing led to another, until soon I was dressing myself in the panties and bra before I masturbated.

One day, it all ended too soon. While my mom was cleaning my room, she found the panties and bra and promptly made me throw them in the trash. (I had hidden them in a empty model box in the heater vent on the floor behind my bed. She decided to vacuum it out and found them!) I don't think I will ever forget the humiliation I felt as a carried that small box with my treasures inside to the trash can, as my brothers laughed and teased me the whole time!

I didn't experiment with cross-dressing for several more years after that, until I finally had an apartment of my own. I discovered the apartment laundry room and the joy of mail order.

The laundry room was a great place to get the panties and bras I wanted. It was just a simple matter of being a "good neighbor", taking a load of clothes out of a washer, putting it in a dryer for someone else and "forgetting" to put their bras and panties in. I got caught stealing a pair of panties and a bra one time by the downstairs neighbor! As I was taking a load of laundry back to my apartment, she confronted me at the stairs and TOTALLY WENT OFF, accusing me of what I had done! Luckily, her boyfriend was there to calm her down, saying that she had no proof that I had taken them. I had just enough of a beer buzz that I didn't care! I had what I wanted!

Mail order was also a good place to get what I wanted and even the joy of looking through the catalogues while I waited for my order to arrive was a turn-on. Here's a little story for you.... Several years ago, I ordered a garterbelt and a pair of seamed stocking from Fredericks of Hollywood. I just couldn't wait for them to get there and would go home at lunch everyday to check my mail. One day, THEY FINALLY ARRIVED! I was SO EXCITED! I tried them on and figured I'd wear them for the rest of the day, so back to work I went. I probably wasn't there for 15 minutes before I heard one the ladies (I use that term loosely... she was an older, butch looking broad) yell out, "OH, MY GOD! WHAT THE HELL HAS HE GOT ON?!?" What I didn't realize was that as I walked, my jeans would stretch across the back of my legs and you could see the outline of the garterbelt straps! I don't think I've EVER ran to the bathroom as fast as I did that day! Needless to say, I took everything off and stuffed them down the front of my pants! Just thought you'd get a kick out of that one!

Halloween came around once again and this HAS TO BE the best time of the year for a cross-dresser. I went to a local store and bought my first wig. I also bought a vampire cape, just to hide my true intentions. Although I have never been questioned by a sales clerk when I have bought panties and such, I have found that Valentines and Mother's Day also make a great time to buy lingerie. If you can't wait, just buy a birthday card and a box of candy at the same time.

By now, I had quite a collection of lingerie and discovered the joys of a VCR camera that I had borrowed from my brother to go on vacation. I even made a tape of myself getting dressed and walking around wearing my panties, garter belt and stockings, a stuffed bra, high heeled shoes and wig. I shot a lot of it using my reflection in a mirror, always being careful not to show my face. It wasn't very good, but it was better from a cross-dressers point of view than those lame transvestite films that show them getting spanked when they get caught stealing panties.

My cross-dressing came to an end again when I moved in with my new girlfriend. Of course, there was no place for my panties to go, except in the trash. I wondered what it would be like living with her and soon found myself wearing her panties and bras when she was gone. Even doing laundry was a turn-on for me as I folded her lingerie.

After awhile, we broke up (I found out she was into shooting up Crank and would disappear from Friday night until Monday morning, with no word to me where she was going or what she was doing. Not that I was an angel! I was still drinking my beer and smoking weed! I finally just couldn't take it anymore and threw her out!) and she ended up leaving with little more than the clothes on her back. That was good for me because I would only give her what I wanted to and kept the rest. This also included her makeup, which I soon started experimenting with.

I would usually start by putting my wig on. (Another Halloween purchase after I had to throw away my first one.) Then I would tuck myself between my legs and put on a tight pair of panties to keep it in place, followed by another pair of my pretties panties. Next I would put on my bra and stuff it with two water filled balloons for my breasts. From there, I was on my own and would try on teddies, camisoles, slips, garter belts and stockings and would keep layering them until I got the look that I was after. Then I would start putting on my makeup. I would put on some blush, pencil in my eyebrows, put on some bright red lipstick and use some blue mascara over my eye lids. After a little bit of practice, I actually started getting good at putting it on. (At least I thought so at the time!) But the makeup made a world of difference in my appearance.
After I was all made up, I would parade back and forth between the mirrors in the bedroom and the ones in the bathroom and admire the way I looked as I swished in front of them. Even after all of that, there seemed to be something missing and I found out what it was when I completed the look by trying on some of the dresses that had been left behind. That's all it took, as now I could not only watch myself get dressed, but could actually do a slow strip tease in the mirror as I got undressed.

I'm still cross-dressing and have no intentions of stopping! I've been buying dresses in a more conservative style in hopes of SOMEDAY getting out of the house and mixing it up with the other Girls! (or Guys!)

I'm sorry if this is too long... I was going to divide it up, but decided to just post it all at one time. I hope you enjoy it. (And the many other experiences I have to share!)

Hugs,
Min

[Janet_Johnson]

Thats a very interesting story, thanks for sharing it dear.