Bi-Sexual Male / 50
Grandma Started It
This is something basically I never spoke and likely never will. My father was introduced to crossdressing by his mom when he was kid, he had a trauma about it and never actually stopped dressing, he would spend time alone each weekend and my mom (and I) knew he was around crossdressing… my mom told me the story she knew about him and his mom, it was somewhat weird and something that was never spoken or addressed beyond my father confessing it to my mom.
Well, little did my mon know that my grandma actually used to dress me with panties and girl clothes every once in a while when “I needed a shower “ but had no spare clothes with me in her house…
I don’t really remember how much this happened, probably only a few times before I was like 6-7 yo, but that was it for me, I developed a taste for feminine clothing and started to use my mom’s underwear, lingerie and dresses around 10, and spend all my teen days crossdressing as much as I was able. My mom has a very nice collection of sexy lingerie and I wear all of them for years each time I was alone in our house… she would go visit her parents each year and I was in heaven dressing all day long while my dad was working… and lingerie was just the first part, on my exploration in her drawers I found also her toys and had so much fun when I was teenager, I had a real addiction to fuck my ass while dressed with many of her clothes… then I went to college 1 hour from our city and moved on to buying my own clothes, and wearing my GF clothes, I was lean enough to fit in girl clothes even when I was much taller… I also “developed” a talent to steal clothes and I dressed in clothes from all neighbors, I even went as far as to learn how to break into houses and dress with the underwear of many girls and woman living in the surroundings… later I was living with my GF and another girl as roomies… the other girl was friend of my GF but used to flirt with me when we were alone, we never went further but she was hot enough for me to want something from her, so I started using her clothes when I was alone, I loved her clothes because she was tall and fuller body, so her mini skirts and jeans fitted me perfectly, I’m amazed that I was never caught, I stopped dressing around 30, but nobody close to me knew about it… I guess I was able to move on from what my grandmother started in my and my dad…
Well, little did my mon know that my grandma actually used to dress me with panties and girl clothes every once in a while when “I needed a shower “ but had no spare clothes with me in her house…
I don’t really remember how much this happened, probably only a few times before I was like 6-7 yo, but that was it for me, I developed a taste for feminine clothing and started to use my mom’s underwear, lingerie and dresses around 10, and spend all my teen days crossdressing as much as I was able. My mom has a very nice collection of sexy lingerie and I wear all of them for years each time I was alone in our house… she would go visit her parents each year and I was in heaven dressing all day long while my dad was working… and lingerie was just the first part, on my exploration in her drawers I found also her toys and had so much fun when I was teenager, I had a real addiction to fuck my ass while dressed with many of her clothes… then I went to college 1 hour from our city and moved on to buying my own clothes, and wearing my GF clothes, I was lean enough to fit in girl clothes even when I was much taller… I also “developed” a talent to steal clothes and I dressed in clothes from all neighbors, I even went as far as to learn how to break into houses and dress with the underwear of many girls and woman living in the surroundings… later I was living with my GF and another girl as roomies… the other girl was friend of my GF but used to flirt with me when we were alone, we never went further but she was hot enough for me to want something from her, so I started using her clothes when I was alone, I loved her clothes because she was tall and fuller body, so her mini skirts and jeans fitted me perfectly, I’m amazed that I was never caught, I stopped dressing around 30, but nobody close to me knew about it… I guess I was able to move on from what my grandmother started in my and my dad…
