The Rest Stop

bySkimpylilpanties©

I was sitting in my dorm room one night bored as ever. I so wanted someone to chat with online, but there seemed to be no one interesting as usual. Just random bots and webcam offers that annoy the shit out of me. Now I enjoy talking to women and having sex with them, but I also have a passion for being one.

There is something so great about dressing as a girl and performing sexual acts on men. I can still remember the first time I dressed up as a girl, I grabbed a wig that my mom had in her room, it was long and black. I put on a pair of my sisters panties and bra, then proceeded to gather more items. Before I knew it I was standing in some black leather pants, and a tight girly white t-shirt that said SEXY in pink glitter across the chest. The pants fit great, nice and tight, hugging my ass which made it look so sexy and hot.

I then proceeded to try my hand in some make-up and before I knew it I looked like a completely different person. I couldn't believe it! I was shaking from the excitement on how good I actually looked, I was beautiful, sexy, and wondering what it would be like to be with a man. For the most part, at least in the beginning, I never really found men all that attractive. But over the years of experiencing different things and becoming more in tuned to my feminine self, I have totally become attracted to men. The best ones for me are the masculine, alpha-male types. I love a man who when they hold me in there arms I feel powerless to their touch.

Like I said before, I was in my dorm room bored as ever, and it was the perfect time to dress. Now I've dressed several times in the room while no one was around, or I'll dress at a friends house for a little fun, but never have I dressed in public. Well, tonight was the night, I finally made my mind up and now time to find and outfit. I pulled out a black leather skirt that sort of has the same design as a cheerleading skirt, just more gothic. To go with that I have this pink corset, and a pair of shiny black knee high boots. I also have these great black leather panties that go great with the skirt. I took all of my stuff including my long black wig and make-up, put it in a bag and go to my car. After about an hour of driving around I find this rest stop along side the road.

I figure it will be a good place to stop and start changing into my other self, in which I've named Brianne. The first thing I do is strip completely naked, I look around nervously to so if anyone can see me, but the cars are few and far between. It was pretty dark at this rest stop, which was basically a pull off on the side of the road with picnic tables and a few trees. I then started in on my make-up, getting the base down before I put my wig on. Then I slid my panties on which feel so nice on me, hugging me in all the right places. The skirt went on next, then the corset and finally the wig. I put on my eyeliner, which really makes my eyes look so sexy, and then I followed that with some blue eye shadow.

It wasn't until I started on my red lipstick that I noticed someone walking toward my car. My stomach turned and I got so nervous. I didn't know what they wanted, nor how they would react to me. The next thing I know he was at my window, he gave a little wave as he looked in on me, so I slowly rolled the window down. He asked me how my night was going, where I was headed, things like that. I answered in a quaint little voice that I was just on my way home and got tired so I stopped here for a few hours. I couldn't get over how cute he was, a trimmed goatee, sexy wavy blonde hair, a nice build that my skinny ass feel even skinnier, which I liked. He was wearing a dark t-shirt and some jeans with a classy brown belt and silver buckle. I only remember the buckle because I couldn't help but glance down there from time to time as we talked to get a look at his crotch.

Eventually I felt comfortable enough that I got out of the car and we chatted on just various things. I could tell it was just small talk leading into what he really had in mind, which I knew was my ruby red lips around his cock. What was nice is that he knew the whole time I wasn't really a girl, but treated me as if I were one the whole time, this turned me on so much. With a laugh he would do a little teasing touch to my arm like he was testing the waters, trying to see how far he could go.

I would slowly get closer to him until we were only inches apart, still talking our nonsense about whatever. The next thing I know he leaned in and I was attracted straight to his lips as we met and kissed right by my car. I was wondering if anyone else could see me, but at the time no one else mattered, because this guy totally hit my hot buttons, and now I knew I was going to give it to him. As we deepened our kiss I felt his hand slide down to my ass and he gave it a little squeeze. I let out a girly moan as he caught me by surprise. I had my hands on his broad chest at the time, but I couldn't resist and I slid one of them down to the bulge in his pants.

He broke the kiss and looked around. He ask me to follow him, so he took me by the hand guiding me down this concreted path. I could hear my heeled boots tapping so loud as I walked. He led me to this tree and leaned up against it. I was so hot by then that I immediately dropped to my knees, I had to see what he had down there. I unbuckled, unzipped, and out sprung a semi-erect beauty. It was long and thick, the kind that will intimidate you at first look when it's just hanging there in front of you. I bet he was at least 8 inches maybe 9 and I was so hot for it.

I took it in my mouth, hearing him moan as he felt my warm wet lips wrap around him. I ran my tongue under the head of his dick as I began to take in more of him. I felt him place his hands on the back of my head, putting a little pressure to go deeper and deeper, in which I desperately wanted to do. He was so massive that I couldn't take him all the way in, so I was gagging on him after so many inches. Being somewhat experienced at sucking cock, I have been able to relax my throat enough to swallow a thinner cock, but his was too thick, occasionally it would slide all the way down my throat, but it didn't stay there for long.

I sucked him to a rhythm as his hip began to gyrate. By this time he was fully erect, filling my mouth completely. I grabbed his dick with my hand and ran the length of it, still sucking him with my ruby reds. I cupped his cum filled balls, massaging them. Occasionally I would pull his dick from my lips and lick all the way down the shaft, giving his balls a little tongue action. I could feel his cock lying against my face as I tickled him. I started to take him in again, but he pulled it away from me and took me by the hand again. He started walking me to a set of picnic tables not far from the tree but they were more out in the open than the tree was, so I was kinda nervous.

He told me to get up on the table, so I put me knees on the bench seat and laid across the table top. I felt him lift my skirt around my waist, sliding my panties off. Then I felt the head of his prick on my ass and began to feel pressure. With a pop his massive head was in along with some pain. He slowly guided it in, then pulled it out, then in again, going deeper each time. It hurt only at first then my muscles started to relax. I felt his hands on my hips as he pumped it into me deeper and deeper. I felt him thrusting faster and harder and all I could do was hold on to the table as he fucked me like a whore.

I felt the so dirty and so aroused, that I didn't even care every time a car would pass by with the headlights just barely hitting us. I couldn't help but let out a moan when he would thrust it in me so deep his balls slapping against my taint. I could hear our bodies slapping together in a rhythm, while our sweat dripped on the table. All at once his pounded me hard and held it in deep, letting out a pleasurable moan, he spurted his white hot cum inside me. I could feel his cock pulsating as it unloaded in me, wave after wave, until if started dripping out. He pulled out of me and made me clean him off with my mouth, as I sat my ass on the cold wet seat. As I finished, he put his cock away and said thanks for the piece of ass. And walked away. It was just then I realized he had my panties in his hand. I guess they were his trophy.

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bySkimpylilpanties© 16 comments/ 75286 views/ 16 favorites

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by Anonymous

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by Anonymous05/29/14

Amazng Story

I loved everything about it. It reminds me so much of my first time. Keep it up!

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