intro to the world of cross dressing

My family was middle class mutt of a family. My mom brought two daughters and one son, Tammy, Lilly, and Teddy, or “Tee” as we call him, into the marriage; she had with my dad, and they had two, my brother and me. My full brother’s name is Ken, and I’m Sam. My dad was an accountant and a part-time college professor at the local community college, and my mom stayed at home as a housewife. We were all dragged to church every Sunday and when we became of age we were allowed to choose whether or not we would go. Tammy was nine years older than me, and she as well as the others gave my parents such a hard time with the rearing process that by the time it got for me to choose, they weren’t having it for me. As I said Tammy is nine years older than me, Lilly is two years younger, Tee is another year younger. Ken is only two years older than me, so there was kind of a divide between the siblings, but “us-against-them” still rang true within the sibling versus parental unit battles—we would vouch for each other and corroborate the stories. We had more than we needed and had a reasonably happy life in all in all, however, drugs and alcohol started becoming a part of the children’s lives and became the pivotal point of our daily living, but that will come into play later…

When I was but a toddler, my sister would like to dress me up in her panties when her friends were over for a sleepover. I didn’t disagree with this being that I was only a toddler, but it sparked in me an appreciation for the feminine fabrics and fashions. I would sneak into my mom’s intimates and put on her slips and panties, and nylons. She didn’t have anything sexy; my mom was forty when she had me and my dad, forty-six—nothing special. I would get into her nightgowns and parade around the house, and the girls in the family found it cute, so they would call me “Samantha”.

When we would go out to the department stores I loved the feeling of the women’s underwear, the satins and silks, lycra and spandex, it all felt so wonderful to me. I remember I would raid my sister’s panty drawer and sneak on her panties, one time when I was in kindergarten, I wore some of her panties to school and didn’t remember about it until half way through class, but being only five my attention was diverted rather quickly and I carried on as any child would.

In my late elementary school, early middle school days, I would wear the panties I stole from my sisters, their friends, my friends’ sisters and masturbate… a lot! I probably jerked off more than necessary; I was a pretty horny little devil.

One time when I was thirteen, Ken and I were up late watching a porno flick that he had gotten his hands on and he asked me if I’d ever had a blowjob before. I said I hadn’t with a little trepidation, and we made a deal. If He sucked me off, then I’d suck him off—agreeing that we wouldn’t even have to look and we would just watch the porn going on. He got down on his knees and I sat down on the couch facing the TV and readied my dick, and he put it in his mouth briskly sucking it, as I reflect he probably wanted to just hurry up and get his end of the bargain complete so I would then be sucking his dick. I imagine his mouth started hurting or something because he asked for a change in position. As he pulled down is pants and revealed a rather sizable dick, I took a hold of it, and was about to put it in my mouth when I tensed up and got nervous and couldn’t. I told him so and he said it was ok, and we promised to never speak of this again.
The next night I invited my best friend from across the street over and invited him to the same deal. He went home and showered and came back. As I sucked his dick it tasted very soapy and I wasn’t sure if I liked it or not. When he got down to sucking my dick, he didn’t seem very thrilled I asked him what it tasted like and he told me “hand”. Like I said, I liked to masturbate a lot. That would be the end of my experimentations for a little while until later on in life.

As I got older my panty wearing fetish subsided and wouldn’t rise up again for a little more than a decade. All my siblings got wonderful grades except Ken and me. We weren’t exactly the brightest of kids, sort of day dreamy and idealist, pot head alcoholics is what we became. Every day it was smoke weed, and cigarettes, rebel and anarchy, punk rock and girls; standard fourteen year old mentality. However, my thong fetish was discovered. The girl who sat in front of my during my eighth grade biology class would lean way forward and it was there that I discovered the thong. Seeing a huge grey suede sissy style satin g-string whale tail; it was glorious. After that I started noticing a lot of girls at my school wore them and I loved seeing the whale tails, the visible thong lines, I became absolutely obsessed with the thong and g-string and ever other panty after that had become boring; I was in heaven.

Throughout middle school and high school I had girlfriends, and I would somehow or another find my way into their dresses and thongs, one girlfriend even complained because I looked better in a particular dress than she did. I can’t help if I have, what I guess is called a swimmer’s body; very curvy. But my fetish ebbed and flowed and became lost and found again.

It wasn’t until I became an adult that it started up again. My sister was moving around to another apartment and she was throwing away a bunch of her old thongs. Well, I couldn’t just let those go to waste so I volunteered to throw them away, and I swiped the whole lot. There were all sorts of colors and styles. It was a treasure trove of blues, pinks, reds, lace, cotton, strings and mesh.

That lasted for some time, but then I had a moment of guilt and shame, not knowing what was going on within me and I proceeded to cut up all the thongs and through them discreetly away, neatly stashing the fetish away for about a year until it surfaced again and I bought my own pair, pretending it was for my girlfriend. Man was I nervous. But I went through with it. I still have it today and it’s my favorite thong I have. I would periodically steal my sisters’ thongs and panties, but I have my own stash now.

I’ve since become sober and have accepted the fact that I am a cross-dresser, I don’t want to be one full time but I enjoy in my own time being as I am. I no longer feel guilt and shame about it, though I’m not ballsy enough to walk out in public dressed as such without some occasion allowing it like Halloween or a convention or something.

I have a lot of stories that I plan on writing; some true, some fantasy, some fictional completely. I’d love to tell them if you’ll let me. I know this hasn’t been exactly a sex story, but what you read is one hundred percent true within this text, names have been changed but the events are all real. Let me know what you like and I will add my own as we go along. I’d love to write for you, and with you. I’m hoping to express a fantasy I have next involving my cross-dressing, panty peeking, and my oldest sister Tammy.

Wish me luck! Thanks!

–Joni Alabaster