Stefanie's Crossdressing Memoirs Vol. 1
I've been crossdressing for quite a while now and experiencing all the ups and downs associated with it. I figured it's time I share some of my experiences with you all out there--at least, those of you out there that I haven't already had experiences with ;) I'll be breaking this down into multiple posts since I have a decent bit to talk about. But I'll do my best not to be too boring :)
My crossdressing started like many others, in my early teens (late 90s) I stumbled across mom's pantyhose in the laundry room, and when I went to move them out of my way I was stunned at how soft and smooth they felt. I never really noticed them before but after that I seemed to pay more attention whenever I would see a woman in public wearing nylons. Eventually I found myself back in the laundry room and those tan pantyhose found their way back to my locked bedroom and onto my legs. The feeling of knowing it was so wrong but felt so amazing was difficult to process at the time. But this newfound interest was very difficult to indulge, as it was my parents, two older siblings, and myself in a small/medium sized house. Needless to say, I had a couple very close calls of getting caught. There may have been some suspicion here and there but I never got caught in the act as far as I know :)
However my mom wasn't the most fashionable, and as a teenage boy I quickly outgrew the few things she had that I liked wearing as I wanted to try wearing more and more girly things besides pantyhose. This continued through high school in the early 2000's, and around this time I discovered that the internet CD community was pretty decent sized, so it made me feel good to know that there were others like me out there. But when I would get access to a chat room or message board, I found very few people my age, and most folks understandably weren't interested in chatting online with a teenager. The age of only one shared desktop computer in the house made this online community difficult to access though, and I had to be very careful to cover my tracks online. Through the internet, I had been exposed to many facets of the crossdressing lifestyle at this point, however I still considered myself a straight guy who liked wearing panties and stockings/pantyhose, since that was most of what I could get my hands on.
The college I attended required full time students to live in the dorms, and the rooms weren't very big. They didn't offer much for storage either, so hiding the few girly things I had was out of the question. It was during this time that my only outlet for the urge to dress up was watching more and more CD/TS porn.
After graduating college in 2009, I finally got my own place and started my job. My dressing up didn't actually take off as much as you'd expect, given my strong desire to do it for so many years that I largely had to suppress, or simply didn't have the means to satisfy that desire. It was mostly a function of being a recent college grad who didn't have too much money to spare on this pastime, but also a function of I didn't really know how to progress with dressing up, now having so much freedom to do so. I slowly began acquiring more clothes, not just stockings and panties, but a dress or two, some tight jeans, and even my first pair of 4" high heels, which I immediately fell in love with even though at first I struggled to walk in them. And my taste in cd porn that I enjoyed had slowly evolved--I found that I now quite enjoyed not just pictures or videos of solo cd's or cd on cd, but also crossdressers having sex with dominant men.
As time went on, I wanted to be more and more like all the other crossdressers I had seen online in pictures and all sorts of videos. And I had the revelation of what I needed to take my dressing to the next level, which in retrospect was more of a "no duh" moment than a revelation. I realized I needed a wig and makeup to complete my look. And that's what I did; I ordered an inexpensive wig online, and purchased very basic makeup at a pharmacy: lipstick, eyeshadow, nail polish, and some foundation.
This all ultimately built up to one critical moment, one which I never would have predicted the first time I slid those tan pantyhose up my legs so many years ago--the first time I not only dressed up in front of another person, but also the first time I sucked cock.
This is where I'll end Vol. 1, as this was a turning point for me and my dressing up. I was no longer just a fan of occasionally wearing something silky or lacy and watching CD porn--I was ready to become a fully dressing crossdressing cocksucker.
Thanks for reading and I hope to see you at Vol. 2 where I share the next stage of my crossdressing journey!
Muah!
xxoo
Stefanie
My crossdressing started like many others, in my early teens (late 90s) I stumbled across mom's pantyhose in the laundry room, and when I went to move them out of my way I was stunned at how soft and smooth they felt. I never really noticed them before but after that I seemed to pay more attention whenever I would see a woman in public wearing nylons. Eventually I found myself back in the laundry room and those tan pantyhose found their way back to my locked bedroom and onto my legs. The feeling of knowing it was so wrong but felt so amazing was difficult to process at the time. But this newfound interest was very difficult to indulge, as it was my parents, two older siblings, and myself in a small/medium sized house. Needless to say, I had a couple very close calls of getting caught. There may have been some suspicion here and there but I never got caught in the act as far as I know :)
However my mom wasn't the most fashionable, and as a teenage boy I quickly outgrew the few things she had that I liked wearing as I wanted to try wearing more and more girly things besides pantyhose. This continued through high school in the early 2000's, and around this time I discovered that the internet CD community was pretty decent sized, so it made me feel good to know that there were others like me out there. But when I would get access to a chat room or message board, I found very few people my age, and most folks understandably weren't interested in chatting online with a teenager. The age of only one shared desktop computer in the house made this online community difficult to access though, and I had to be very careful to cover my tracks online. Through the internet, I had been exposed to many facets of the crossdressing lifestyle at this point, however I still considered myself a straight guy who liked wearing panties and stockings/pantyhose, since that was most of what I could get my hands on.
The college I attended required full time students to live in the dorms, and the rooms weren't very big. They didn't offer much for storage either, so hiding the few girly things I had was out of the question. It was during this time that my only outlet for the urge to dress up was watching more and more CD/TS porn.
After graduating college in 2009, I finally got my own place and started my job. My dressing up didn't actually take off as much as you'd expect, given my strong desire to do it for so many years that I largely had to suppress, or simply didn't have the means to satisfy that desire. It was mostly a function of being a recent college grad who didn't have too much money to spare on this pastime, but also a function of I didn't really know how to progress with dressing up, now having so much freedom to do so. I slowly began acquiring more clothes, not just stockings and panties, but a dress or two, some tight jeans, and even my first pair of 4" high heels, which I immediately fell in love with even though at first I struggled to walk in them. And my taste in cd porn that I enjoyed had slowly evolved--I found that I now quite enjoyed not just pictures or videos of solo cd's or cd on cd, but also crossdressers having sex with dominant men.
As time went on, I wanted to be more and more like all the other crossdressers I had seen online in pictures and all sorts of videos. And I had the revelation of what I needed to take my dressing to the next level, which in retrospect was more of a "no duh" moment than a revelation. I realized I needed a wig and makeup to complete my look. And that's what I did; I ordered an inexpensive wig online, and purchased very basic makeup at a pharmacy: lipstick, eyeshadow, nail polish, and some foundation.
This all ultimately built up to one critical moment, one which I never would have predicted the first time I slid those tan pantyhose up my legs so many years ago--the first time I not only dressed up in front of another person, but also the first time I sucked cock.
This is where I'll end Vol. 1, as this was a turning point for me and my dressing up. I was no longer just a fan of occasionally wearing something silky or lacy and watching CD porn--I was ready to become a fully dressing crossdressing cocksucker.
Thanks for reading and I hope to see you at Vol. 2 where I share the next stage of my crossdressing journey!
Muah!
xxoo
Stefanie
7 years ago
