My first experience
Posted: Wed Oct 03, 2018 2:26 pm
Hello to all.
My first experience of the joys of crossdressing was when i was 17. I was dating a friends older sister. We had been invited to a Halloween fancy dress party. I am a rocker and at that time i had very long hair and always wore skin tight jeans and leather jackets. I was stuck in my ways and not interested in a fancy dress party. To be honest i looked silly enough. Lol. My firlfriend thought differently. She said i needed to make an effort. But it was alteady 1845 on a friday night and i was already 5 or 6 beers into the evening.... So no chance to get an outfit. I will spare you the discussion that took place. It ended with me dressed in my girlfriends school uniform. My hair in pigtails. Stockings, suspenders and a g string underneath.
Cut to the club............. I was very popular. Lots of free drinks. I did not feel any different about myself and definitely hadnt considered doing it again. To be honest the g string was uncomfortable.
That all changed when i went to the toilet to have a wee. I was at the urinal as always when an acquaintance walked in and said..............f**k me i thought my luck was in. Which made us both laugh. As i walked past him to leave he helped himself to a feel of arse and again complimented me. It was then i realised i liked being complimented about my appearance.
Up until that night i was lost in averageness. Average hight. Average build. Average penis. Never realy noticed at all. But now i was empowered. And from that moment i used my looks to my advantage. More free drinks and even made it into the dancers cage. With 3 other school girls. It was then i spotted my girlfriend arms around her former boyfriend tongues locked together. So i took a chance with what was by now the 2 remaining school girls in the cage with me.... I will save you the details but i had a great night with them both.
Ever since that night i have taken every opertunity to dress up. Always in secret. That is until i met my current girlfriend. Who is the most amazing person. It was one already messy christmas. When we were talking about fantasies and other naughty things. When she asked to see me dressed. I obliged and have never looked back. I now have a reasonable wardrobe, i have started to experiment with make up and wigs. And i really like my image.
Looking forward much more time in skirts and being admired by my amazing girlfriend.
Writing this is amazingly emotional. Fear excitement and a weight off my shoulders. Love to all. Write again soon.
My first experience of the joys of crossdressing was when i was 17. I was dating a friends older sister. We had been invited to a Halloween fancy dress party. I am a rocker and at that time i had very long hair and always wore skin tight jeans and leather jackets. I was stuck in my ways and not interested in a fancy dress party. To be honest i looked silly enough. Lol. My firlfriend thought differently. She said i needed to make an effort. But it was alteady 1845 on a friday night and i was already 5 or 6 beers into the evening.... So no chance to get an outfit. I will spare you the discussion that took place. It ended with me dressed in my girlfriends school uniform. My hair in pigtails. Stockings, suspenders and a g string underneath.
Cut to the club............. I was very popular. Lots of free drinks. I did not feel any different about myself and definitely hadnt considered doing it again. To be honest the g string was uncomfortable.
That all changed when i went to the toilet to have a wee. I was at the urinal as always when an acquaintance walked in and said..............f**k me i thought my luck was in. Which made us both laugh. As i walked past him to leave he helped himself to a feel of arse and again complimented me. It was then i realised i liked being complimented about my appearance.
Up until that night i was lost in averageness. Average hight. Average build. Average penis. Never realy noticed at all. But now i was empowered. And from that moment i used my looks to my advantage. More free drinks and even made it into the dancers cage. With 3 other school girls. It was then i spotted my girlfriend arms around her former boyfriend tongues locked together. So i took a chance with what was by now the 2 remaining school girls in the cage with me.... I will save you the details but i had a great night with them both.
Ever since that night i have taken every opertunity to dress up. Always in secret. That is until i met my current girlfriend. Who is the most amazing person. It was one already messy christmas. When we were talking about fantasies and other naughty things. When she asked to see me dressed. I obliged and have never looked back. I now have a reasonable wardrobe, i have started to experiment with make up and wigs. And i really like my image.
Looking forward much more time in skirts and being admired by my amazing girlfriend.
Writing this is amazingly emotional. Fear excitement and a weight off my shoulders. Love to all. Write again soon.