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Jessica Chronicles Part 2The

Jessica Chronicles Part 2

The Beginning 

I guess every crossdresser has a back story. I think times are different now days versus the 1980s when all this began for me. Of course I was young, but the world has changed, we have grown some and maybe taken some steps back. I started reflecting on the culture back then. My journey started around 8th grade. 1984. If you go watch the movies back then, lots of sex and nudity. Think about like revenge of the nerd and all those types of movies. Many adult men also purchased playboys and other magazines. I think you kind of did it on the down low back then but still I think every guy had a porn mag. My dad had Penthouse magazines. Besides having boxes in their closet, some in the garage, he always had a few magazines stashed away in the bathroom.  I moved a lot up to that point, like 8 times and many different schools. We finally got a small house with the help of my dad's grandparents in Northern suburbs of Chicago. I was a little chubby since 3rd grade probably due to moving and some apartment living. That has carried through my life as well, but I kinda like being curvy as Jessica now days. Socially, and this is around 8th grade, I played sports all the time and was pretty active. I was a pretty serious baseball card collector and other things like comics and coins. I guess maybe puberty probably started playing a role. As I started maturing at end of 1984, I found my dad's magazines under the counter in the bathroom. First it was just amazing to see women's body parts. Back then I think we actually also read the magazines like playboy and penthouse as there were articles, jokes, and in penthouse, stories. The house we bought was an old summer house and it didn't even have a shower until the next year, so used to take baths all the time. I would always after I found those mags, read them while taking a bath. The first time I masturbated was during that time, in the bathtub. I found that I gravitated to lesbian stories at first. Anything lesbian would immediately turn me on.  I also found stories about crossdressing, feminization, female domination and stuff like that and found that really turned me on.  Sometimes there were stories about how a girlfriend or wife would participate and dress their boyfriend or husband up and have sex. Sometimes go further and go out or even further, involve other people, and making him/her service others or her friends. All that stuff was all I started looking for. My dad also had penthouse letters and penthouse forum. I think maybe I was destinedestined through genes and external influences. I do sometimes wonder if those mags weren't part of my yourh, would I have found all this stuff about me. Most likely as cds always seem to find their way back to dressing. So there i was, 8th grade, freshman, year, finding that these feminization stories really resonated with me. I have a sister that is 18 months older. Eventually I decided I wanted to see what it felt like to wear girls intimates and eventually found myself in her room going through her dresser one day when no one was home....to be continued in part 3

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Jessica Chronicles Part where

Jessica Chronicles Part 3

.....ok. where did I leave off? Wearing my sister's clothes. At first it was trying on panties and cotton night gowns. I masturbated from the beginning though. I would go through her dresser and try on different panties as the fabric also felt so incredible against my body and umm, well, a specific part. EventEventually I moved on to trying bras, other clothes and then makeup. At that age I didn't have any facial hair yet so it was easy with mullet like longer hair to put on some eye shadow and lipstick and look pretty good. It always led to masturbating. Eventually I started putting objects in my butt. The stories from penthouse fueled all this exploration. It was tough though at this time to find an appropriate toy to put in me. I actually started with a pencil lol. Then a marker. I then scavenged the house for any type of phallic object. Kitchen drawers, nothing really, until, I found an unused plunger which had a hot dog size handle and rounded top. I could stick it to the floor and lower myself down on it. Most of the time then my sessions included putting things in my butt and dressing up as much as I could. Things mostly stopped with this around sophomore year. Maybe a combination of spending time with friends and those things. I do remember though one day I was fully dressed and at that time found cheech and chong stuff and fell asleep on my bed all dressed. My parents came home after work and turned on my light and woke me up and found me like that. We never said anything about it but I think they played a role in me pausing in that stuff for the time. It wouldn't be until college that these feelings and this stuff popped up again in my life. To be continued to Part 4.

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