On School GroundsbyPenanceS©
It’s amazing how good the cloth feels against your bare skin. I had never thought of myself as anything but a straight and regular Joe. I didn’t think that I’d get a stiffy wearing woman’s clothing like this.
I looked at myself in the mirror, just to see if my padding was well, there. I had borrowed one of my ex-girlfriends bras and stuffed it with a pair of socks. The purple dress that I was wearing didn’t fit me at all, but hey, that was borrowed too. This was all for a college prank, and most of the guys in the dorm were doing it. My roommate thought that I, and the rest of us, were all freaks and summarily I couldn’t get him to talk to me for the rest of the semester.
I wanted to go sans panties, and just let my dong hang out if you know what I mean, but I did have classes to go to on this fine day, and I didn’t really want any of my professors to see my package and then have my little old self end up getting hauled off to the slammer for indecent exposure or something.
I hefted my satchel around my shoulders, being careful to align the shoulder strap of the bag right in between my “cleavage” area, and therefore set off my “breasts”
My roommate who didn’t have any classes that day – lucky bastard – considered me an abomination, but I didn’t care; I was always one to set off the status quo - I hated being labeled as different.
I loved showing off, and since we weren’t allowed to streak, than this was the next best thing.
My professors for the most part were very understanding, as I had chosen to go to all of my classes in a dress, now I knew what boy George felt like. Several of the “girls” or was it guys (it was gender bending day, you know) were hitting on me. But, for the life of me I didn’t know if it was just the novelty of being the opposite sex, or if they really DID like me.
My blonde hair was tied up in a ponytail, and I’d made sure that I’d managed to shave off my mustache the night before. Several of the girls (uh men) were sporting eyeliner mustaches and beards, and had taken the opportunity to hit on me.
It felt kind of good to be on the opposite spectrum for once and be the hitee instead of the hitter. When we went outside to switch classrooms I was given yet another surprise as the wind decided to lift up my skirt and blow right through my boxer shorts. I couldn’t believe how big of a turn on this was, and I couldn’t wait to get back into my dorm room and strip out of these damn clothes.
Part of me wanted to keep the dress on and to jerk off feeling the fabric as it caressed my body, but it was a “borrowed” dress and there wasn’t any way that I was going to let something that someone had lent to me fall into a dirty stain, just because I couldn’t control my hormones.
Classes seemed to drag on for me and it wasn’t until later that night that I was finally able to get the dress off (much to my chagrin, I wanted to keep it on). My poor cock was red and swollen as the images of me in that dress, and the feeling that the fabric elicited seemed to play through my head.
I finally managed to get into my room, lock the door (my roommate would have a class until 9:00 that night so I had a good three hours to go ahead and goof off), peel off the dress, making sure that it was placed on a chair and that nothing would happen to it, and play.
I stared at its gorgeous velvet coloring as I began to jack myself off, feeling my cock in my hands as I imagined the smooth satiny softness of that dress as it was wrapped around my rail-thin form.
This was all that it took and suddenly I was cumming like nobody’s business. My orgasm lasted for what felt like a good four or five minutes but it might have only been a minute or so (or less). My cum spurted up so much that the first globule landed in my hair, and then the next several went downwards from there until the last dribbles eked their way through into my pubic hair.
I did think as I fell to sleep, pulling the covers over me, that I had never thought that cross-dressing would be a thing for me… little did I know.