sissypantyhoseboy90's Blog

[Story] June 3rd 2011, Dream Come True!

Friday June 3rd, 2011, I went out to a local bar. Not crossdressed, just the man in me. I am normal on the outside, beer drinker, hell raiser, party kinda of guy. So anyways, im sittin at the bar with my buddy sam, drinking coors light and shots of cuervo. well sam had to cut out early cause his wife was getting bitchy, so he left and i stayed and got d***k. at the other end of the bar i was eyeing this gorgous red head, id say, 5'3, slim body nice tits, drinkin beer, which is a turn on for me when women drink beer!! And she noticed i was lookin at her. So i got up with my beer and went outsid... Continue»
Posted by sissypantyhoseboy90 3 years ago  |  5

[Story] My first time with another crossdresser.

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my b*****r and s****r. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer to waist with reinf***ed toe suntan wolford pantyhose. They were incredibly silky and soft. i rubbed t... Continue»
Posted by sissypantyhoseboy90 3 years ago  |  19

[Story] First time getting caught wearing Pantyhose

When I was 16 years old, I babysat for my moms best friend. I had know Joanne (my moms bff) all my life, she was my second mother. and a single mother at that. And Joanne was smokin hot! Had thee biggest crush on her since i can remember. Joanne always wore pantyhose or stockings, and i mean always, one night i slept over at her house, i peeked in her bedroom and she was wearing a teddy and pantyhose, and ofcourse i had to masturbate, because like i said, she's a woman who gives an instant boner at first sight. Anyways, she had asked me to babysit her 2 boys on a friday night. Not a big deal e... Continue»
Posted by sissypantyhoseboy90 3 years ago  |  28
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