Slut in the Woods Ch. 01

In the summer following my sophomore year of college, right before I was twenty-one, I had a routine, and I followed it to the letter. Once I knew my parents had left the house and would be gone for at least a few hours, it'd start: shaving all the hair off my body as best as I could, showering with floral shampoo and soap, then clothes--first panties, then the bra (I still used rolled-up socks back then to stuff it, give myself more of a C cup), stockings, styling my hair just right (I kept it long, and let my parents believe the half-truth of being kind of a punk/metal sort of guy), adding a little bit of makeup--just some eyeliner, mascara, lipstick, making sure the latter didn't get on my teeth--then adding a skirt, a top, and Mary was back to visit.

When I was Mary, I didn't do much; I mostly just kept to myself, stuck in the house. I didn't want anybody in the neighborhood to notice me, so I rarely left, and when I did, it was as inconspicuously as possible, dressed as a guy with my femme stuff in a bag on the passenger seat of my car. Instead I sat in the living room, listened to some hardcore punk, and roamed the internet for sex hookups. It was a bit of a hopeless vicious cycle, signing up, dealing with a lot of jerks who expected me to just give them pics of myself, as well as married men who thought that I'd willingly help them cheat on their spouse, and the occasional completely deluded creep--then I deleted my profile, and repeated the process the next time I was dressed up.

I was a coward. I didn't know what Mary was to me, whether it was just a fetish or something more, but I knew I wanted to have sex with a man as Mary--and I wussed out every time that an opportunity arose. I'd get something going on Grindr or Sniffies, and be so close to inviting a guy over to my house or drive over to see them, and then at the last minute decide that it wasn't worth the risk and ghost; I'd look up cruising spots and message boards and announce that I'd be going somewhere, only to either not show up, find nobody there (such a common occurrence, actually), or, in one or two cases, actually meet someone there, take one look at them from the safety of my car, be immediately creeped out, and just turn right around and go home. I hated myself for it, in a way; I hated that I couldn't just go through with something like this, and it made me feel guilty to leave people hanging. Sometimes I wished that someone in my neighborhood would catch me, some guy who secretly was into girls like me, and I'd wind up being their little slut for a few hours, sucking their cock, riding it, all ending up with them cumming on my face--but my neighborhood was so conservative and religious that the chances of this being possible were so slim that it wasn't even worth putting much thought into.

And then, one day, my folks went on a vacation to Florida for a long weekend, and as soon as they'd left and I was in my Mary clothes, I realized that this was the time. I didn't want to be a coward anymore; I wanted to be a slut; I wanted to go through with it, finally.

So I went on Grindr, signed up on a new account and, with a pit in my stomach, started sending out feelers.

Grindr isn't always the best place to be a crossdresser, in my experience; the overlap between gay men and crossdressers isn't nearly as big as someone might want to believe. More often than not I was simply ignored, though inevitably I'd get some hit from some guy with no profile picture, asking for pics, or saying something awful to me. I really hated Grindr, honestly. I still hate it, and I don't go on it anymore. After going through about ten guys, all of whom had no profile picture and were some degree of married or creepy, I gave up; I deleted my profile and wondered if I was just kidding myself about actually going through with it. But instead of getting too discouraged, I instead went over to a cruising spot that I knew about. It was a trail behind the mall; most of the time it was pretty unused, so guys would often go there, walk on a trail, and, presumably, fuck somewhere on it.

Outside sun had a nice feeling to it, as if it would lightly warm but not burn. As I went through the woods, I realized that nobody was here, and decided that if I was already out, I might as well have fun with it. I saw a big flat rock a few feet off the trail, and went to it, sat on it, and began to undress until I was in my lingerie, and started touching myself. The idea of being out there in the middle of the woods, where anybody could potentially see me in such an exposed position, was incredibly hot; and I found myself getting harder and harder. I came close to cumming more than once, and had to slow myself down or just stop altogether, and stare out at the woods, and listen to the birds nearby and the wind rushing through the trees and shaking the leaves.

And then: I saw someone. Someone who had already seen me, and was coming closer. A guy about my age, with a smile on his face.

"Looking good," he said, as he stopped near me. "I assume you're looking, then?"

I nodded. "Please," I said, in my best female voice I could.

"Turn around," he said, as he came closer.

I turned around, and back.

"Keep turned, and pull your panties down, really spread that ass for me."

I did so, not knowing where this was going.

I heard him unzip his jeans. "Fuck, yeah, you little fucking slut. Just dying for dick."

"I really am!" I found myself saying.

"Well, come get it."

I turned around and saw his massive cock jut out from his pants. I'd only practiced on a dildo--a much smaller dildo than that--but I had some idea of what to do, and sank down to my knees and took the big head in my mouth, and began to bob up and down.

I loved it. In that moment I realized I was a cockslut. I needed dick to suck and to fuck. I could taste the sweet beginnings of his precum and knew that I needed cum as well.

He held the back of my head and pushed me into his cock. I felt it hitting the back of my throat and I gagged, but tried to keep his dick in my mouth as much as possible.

"Good girl," he murmured, as I continued to slurp away.

A few minutes later he groaned.

"I'm gonna cum," he said, "where do you want it."

I took his cock out of my mouth and began to jack him off. Ropes of hot jizz splattered across my face, and I sat there getting progressively more and more covered.

"Fuck..." He said, as I stopped jacking him off, and took the cum on my face in my fingers and licked my fingers clean. "You dirty slut."

I smiled, and turned around for him, and dropped my panties again, spread my ass. I looked back at him with an innocent smile. "You think you have another one in you?"

"For you? Anything," he said, with a laugh. "But I think we've got a little bit of company." He pointed to his left, and I turned to see two more guys coming up the trail, pricks in hand.

"Oh. Wow!"