Ok you panty wearing, crossdressing perverts! I’m going to get the ball rolling by telling you girls all about the first time I got all dressed up in sissy clothes.
For some of us, wearing women’s clothes was a gradual thing. Maybe as a young boy you sneaked into your sisters room and tried on a pair of panties, or more. Maybe you slipped on your moms high heels and felt really good about it. Maybe you started to wear panyhose cause it felt good.
For others it came later in life, maybe as a costume, or a dare, something that just made you think “hey, I like this”! For me it was really by accident. The first time I crossdressed was only about 3 years ago. I was living with my two friends, Kelly and Ashley, and still am. They are a lesbian couple. I have known Kelly for, oh, 24 years or so, a long time! Ashley I have known for about 2 years.
Anyway, it was Christmas time, and I wanted to do something different. We always had a running joke that I was their “little bitch” cause they always asked me to do stuff for them. So I decided for Christmas to dress up as a maid and be their slave for a day, lol!
So, having never dressed up before, I went to a costume shop. I bought a maid costume. But it was too small and I ripped it trying to get into it! So then I went to a sex store downtown and got another one, this time bigger. At first that was all I was going to do. But as I kept thinking about it I decided to do more and more. I got a wig. Then nail polish. Then a cheap makeup kit.
Finally I said to myself, heck I’ll do the whole thing. I went to my local walmart and got a bra. Then I needed high heels, boy you have no idea how fast I tried those on! It was like a quick look around, sat down, shoved them on. Yup, they fit, ookk now I’m outta here!!
So on the big day I got up early and put all my stuff on. Outfit, wig, high heels, nail polish, lipstick. I started to make Ashley breakfast, Kelly was at work until noon. Ashley walked out her bedroom, saw me in the kitchen. The look on her face was priceless! She laughed for a long time, but kept saying how great my legs looked!
Then later Kelly came home and she reacted the same way. I must admit, I was feeling sexy and yes, was getting turned on being dressed like that. They gave me a few spankings and had me clean the refrigerator, lol.
Soo, that was my first time I ever crossdressed. They kept asking me when “Betty” was going to come over again. So I did it a few more times, and that is when I knew I loved crossdressing. The rest, well, I’ll tell you in other post! So what about you, lets hear your story. How did you get into crossdressing? I’d love to hear it!