I had known Janet since Junior High school. She lived around the corner from me.
We were boyfriend and girlfriend for a while but that had ended and now we were just close friends.
Now in High School together we would spend afternoons listening to records, doing our homework and discussing events at school. I'm not totally clear on exactly how it happened but as I remember it we were in her room. I was doing our homework as usual and she was fusing over what to wear on a date she had for the coming weekend. I said something about one of the dresses I saw hanging in her closet. She grabbed it and left the room to try it on. When she returned I commented that it looked fantastic on her and paired with a particular pair of shoes I saw on the floor of her closet she would be radiant. Janet giggled and said I had a good eye for fashion to bad I wasn't a girl because she thought it would look even better on me. I scoffed at her suggestion outwardly. Inwardly I was dying to try it on. She left the room to change back into her shorts a top. When she returned I'm sure out of silliness, Janet held the dress out to me and said, you should try it on I know you will look so cute in it. I froze. OMG! how did she know? I'll be the laughing stock of the whole school if I do this. I would die of humiliation I thought. Oh come on its just for amusement she said. So overwhelmed with fear and excitement I burst into tears. I'm sorry she said, I thought we might have a little fun I didn't mean to upset you. It all came pouring out of me. Though the tears I confessed that I really did want to try it on. That I wanted to wear not only the dress but bra and panties too. That I had always wanted to wear girls clothes. She hugged me so tight and said that my secret was safe with her. Janet reminded me that I was the first boy to ever kiss or touch her and that I knew of all her exploits with other boys so we both had secrets to keep.
After a good cry and many words of comfort from her I dried my eyes. Janet went to her dresser and pulled out a matching pair of panties and bra then picked up the dress from the bed where she had tossed it during my break down. She handed me everything. I'm going to the kitchen to get us a couple of cokes, while I'm gone put everything on. I know you will look just darling in them.
I had been wearing my sisters clothes behind closed doors for years so I had no trouble putting on any of the garments on that Janet gave me. When she returned I was sitting demurely on the edge of her bed with my legs crossed very ladylike. You look as cute as thought you would she said upon entering her room. Stand up and turn around let me see. With a big smile, I stood and twirled around causing the dress to fan out. I was in heaven. You look better than I do in that dress girl she said giggling. Do I really I shouted in excitement? Yes and with a bit of makeup no one would think you weren't a girl at all. We spend the rest of the afternoon with me trying on everything she had in her closet. She did my makeup with each outfit. Then had me wash it all off and we started again. Unfortunately my hair was to short to do anything with but Janet had several hats we made work with certain clothes. It was one of the best afternoons I ever had. Janet and I would now spend our afternoons as girlfriends. Everyday after school that whole year I would change clothes as soon as we arrived at her house and we would spend our time looking at magazines, talking about clothes and doing all the things teenage girls do when boys aren't around. Janet and I were so lost in our new found relationship that neither of us would bother to leave the room when changing clothes anymore. After all we were both girls. We lost touch after High School. She married and moved away. I went off to college. To this day I believe she never told anyone my secret. I am so grateful for her help, kindness and friendship.
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