Early years

I had several girlfriends in high school. I'd started looking at lingerie in my mum's mail order catalogues and wearing some of her underwear. Then I borrowed men's magazines from a friend but started buying Mayfair when I was 16. I took my name Karen from my first love. We only ever did foreplay, I used to struggle to get my hand inside her tights and panties to finger her wet pussy as we kissed. I used to wear stockings and suspenders at that time and always thought they gave better access and were sexier to look at. I kept in touch with Karen over the years and would have loved to tell her about how I dressed and went out as a woman. I remember at a party being amazed how glam and sexy she looked in a new dress. I would have liked to have worn it too. Soft silky blouses were the fashion with lacy bras often being seen underneath. It's a look I still love today. Fashions from the eighties have a soft spot for me. One girlfriend did buy some stockings and a suspender belt to wear without my asking and it added to my excitement a lot as we made love. I did think her belt was poor quality as her stockings weren't held up that well, I would have loved to tell her how and what I liked to wear. It was around this time I discovered Fiona Cooper videos. The girls and their outfits drove me wild. I love the clothing, hair and lingerie. I never thought they would have sex at the end of the photoshoot. Mind you I ended up doing things that I wouldn't have thought of when I first started dressing. After I'd been with a girl, I always got the urge to dress and after dressing always wanted to get to grips with a girlfriend. The two things seem to be two sides of the same coin. I was able to pretend I was buying clothes for girlfriend as I started buy my own things. It was many years later that I was able to tell some of my adult girlfriends about my dressing.
Published by yorkskaren
2 years ago
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yorkskaren
yorkskaren Publisher 2 years ago
I'd been wearing women's clothes in my teenage years secretly. I used to wear lingerie under my clothes to go around the shops. I wanted the women to know I too was wearing lingerie and knew how it felt to be wearing a bra. At night I'd drive to quiet locations and have a quick stroll in skirts and heels. All very exciting but I wanted more. Moving amongst women in shops whilst wearing lingerie under my men's clothes was exciting as well but not enough. I decided I wanted some female company and was prepared to pay, so I went to a little brothel. I had my femme stuff in a holdall. I explained to the young woman I wanted to dress up and talk, maybe more and she was ok with that. I got changed, wore a wig but no makeup. We sat on the bed and chatted; I told her all about myself. I then stood up and walked around so I could enjoy the feeling of wearing high heels and started asking her more things about her clothes, what she liked to wear and how she felt about wearing sexy lingerie and stockings. When I started talking about sex, she was still ok with things. I was steering things towards some sort of lesbian thing. She stood up hugged me. Feeling her hands over my body, knowing she could feel my bra and suspenders under my blouse and skirt made me feel great. I'd done the same to my girlfriends during foreplay, telling them how sexy they were and now someone was doing it to me. When she slid her hand up my skirt to my stocking tops I thought I'd cum in my panties. I kept thinking of my girlfriends and how I done that to them, it all felt so sexy and femme. I asked if we could lie down, and she lie on top of me. I pulled up my skirt and spread my legs. Then she lay on top of me, and we rubbed our panties together. Again, thoughts of " so this is what it's like " went through my mind. To be lying on my back, my skirt up around my hips and this woman guiding me through it all. I felt like a virgin, like the girls I'd been with. It wasn't long before I came in my panties.

Karen
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Sandy_Woo
Sandy_Woo 2 years ago
I remember "sharing" mail order catalogues with friends before I was teen. xx
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