First time dressing Fem, with help from my Mom
My first sexual experiences, in my early teens, were sucking off older boys. I loved it and the more I had, the more I wanted.
I was never the typical boy, never played sports, actually spent more time with girls, but not in a sexual way. My features were more fem than masculine, slender, no body hair, even the hair on my legs was thin, and sparse. On more than one occasion my mom mentioned that I would have been a pretty girl.
When my mother caught me sucking off an older boy, she was very supportive. Shortly after that I found an erotic novel (she left it on her nightstand for me to find) about a young guy who dressed as a woman and would go to a couple's house to help the wife take care of her over-sexed hubby, especially sucking his cock and drinking the cum...the wife wouldn't, but the cross-dresser loved cum. I saw myself in him, or should I say the gurl! It never dawned on me that the book was left for me to find. So, naturally I went looking through my mom's clothes, and right on top, black lingerie: bra, panties, garter-belt, nylons, nightie. Again it never dawned on me that mom did this deliberately. I started dressing as often as possible. I felt so good expressing my feminine side. I would dress, but covered it in regular clothes when I sucked off the boys.
Two years later, after dad passed, mom brought those clothes into my room, and said these are yours...she had bought them for me. I was able to be open with her. She helped me and introduce me to a nice loving couple with a trans husband.
2022 Update
I want to add that Mom did this out of love. Some here on xhamster call he an abuser, which is not true. She was not abusive and initially let me explore myself, which at the time was in secret. I was 13 and immediately when I slipped into panties, then garter belt, hose and heels, I felt sexy. This went on for 2 years, again I thought secretly. During this same time I continued as a boy sucking off older boys, many times at home, with Mom knowing what I was doing in my bedroom and in the rec room with the boys. So at 15 when Mom came into my room with the lingerie, she was lovingly helping me be who I am. She helped me with picking out clothes, helped me with make-up, like the parents of transgenders do nowadays.
I was never the typical boy, never played sports, actually spent more time with girls, but not in a sexual way. My features were more fem than masculine, slender, no body hair, even the hair on my legs was thin, and sparse. On more than one occasion my mom mentioned that I would have been a pretty girl.
When my mother caught me sucking off an older boy, she was very supportive. Shortly after that I found an erotic novel (she left it on her nightstand for me to find) about a young guy who dressed as a woman and would go to a couple's house to help the wife take care of her over-sexed hubby, especially sucking his cock and drinking the cum...the wife wouldn't, but the cross-dresser loved cum. I saw myself in him, or should I say the gurl! It never dawned on me that the book was left for me to find. So, naturally I went looking through my mom's clothes, and right on top, black lingerie: bra, panties, garter-belt, nylons, nightie. Again it never dawned on me that mom did this deliberately. I started dressing as often as possible. I felt so good expressing my feminine side. I would dress, but covered it in regular clothes when I sucked off the boys.
Two years later, after dad passed, mom brought those clothes into my room, and said these are yours...she had bought them for me. I was able to be open with her. She helped me and introduce me to a nice loving couple with a trans husband.
2022 Update
I want to add that Mom did this out of love. Some here on xhamster call he an abuser, which is not true. She was not abusive and initially let me explore myself, which at the time was in secret. I was 13 and immediately when I slipped into panties, then garter belt, hose and heels, I felt sexy. This went on for 2 years, again I thought secretly. During this same time I continued as a boy sucking off older boys, many times at home, with Mom knowing what I was doing in my bedroom and in the rec room with the boys. So at 15 when Mom came into my room with the lingerie, she was lovingly helping me be who I am. She helped me with picking out clothes, helped me with make-up, like the parents of transgenders do nowadays.
5 years ago
