First Time Was By A Homeless Guy In The Woods

By tomboy

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Tags: homeless, guy

Added: 23 Dec 2011 Views: 46422 Avg Score: 4.32

cutting wood for gramps and ended up getting fucked
My first time was just after I turned 16, I was born a boy, but always had a girly type build, that caused me to get lots of razzing at school. Just after I turned 16 my grampa wasn't feeling good, and needed some fire wood, the neighbor had a logging crew on his place a year ago, and told me I could cut all the wood I wanted over there.

It was good seasoned oak wood, so Saturday afternoon I took gramps truck over there with the saw to get him a load, I liked cutting wood and was glad to do it for him. The neighbor was gone, so I opened the gate and drove back into the timber, it wasn't very cold, and about half way I came onto a tent with a small camp fire in front.

I stopped and there was a middle aged guy sitting there, shaggy hair, patched jeans and jacket, reminded me of the homeless guys I'd seen in town. I asked him why he was camping there, he told me he had come into some money, and was heading for California. But he didn't like staying in motels, and had gotten permission from this land owner to camp here for a few days.
I told him I knew the owner and that sounded like him, I'm kinda short and small built, 5-5 and 130, and that day I was wearing a pretty snug pair of girls Levi Lowrise jeans, and knew that they showed off my girly figure.

I caught him looking at my ass a few times and had an idea of what he was thinking, I'd had older guys look at me before and some had made comments, and a few of them I'd teased a little. Knowing that this guy was looking got me kind of excited and started slowly teasing him with body language. It didn't take long until he told me that I had a hot looking ass and if I would be interested in showing him more of it. This got me more excited, I'd played with a friend's dick a few times, but had never let anything happen, but out here in the middle of the woods alone with this guy was making me want to go a little farther.

It wasn't long until he asked me to remove my jeans, and as I started undoing my belt and the button, I saw a bulge start to grow in the crotch of his pants. I slowly pulled them down, that's when I remembered that I was wearing a pair of my sister's white Fruit of the Loom bikini panties, but it was too late then. My dick and nuts are very small and there isn't much to see even wearing tight fitting panties and jeans.

His face lit up when he saw the panties, then he asked me to pull my jeans off, I shucked my boots and removed my jeans. Then he had me stand in front of him and he ran his hands up my legs to my crotch, turning me around so that his hands were on my ass. This made goose bumps run all over my body and I was loving the feel of his hands on me, then his fingers were under the leg band and touching my ass. I spread my legs and leaned forward just a little, he asked if I'd ever been with another guy, I said I had only played with the dick of a friend of mine.

He asked me to take the panties off and play with his dick, as he undid his pants and pulled them down I saw he was wearing boxers, so I reached into them and my hand found his half hard cock. It didn't take but a few seconds for it to get hard, he told me to take it in my mouth, so I got down on my knees and started to lick the head of it. As I opened my mouth he pushed forward and shoved about half of it in, it wasn't reallly big, but it was quite long.

A few minutes later he told me to lay belly down on his sleeping bag, it smelled like stale sweat but it was soft, then I heard him getting undressed. He got down beside me and started playing with my ass, I heard him spit on his finger, and then he was sliding it in and fingering me. I parted my legs and he asked if I wanted to get fucked. I was really nervous, but at the same time was wanting it, so said, yes fuck me. I felt him spit right on my ass.

Then he was getting on me, I felt his dick brush my cheeks, he was holding himself up with his left arm and guiding his dick with the other, it felt really warm and he was slowly trying to penetrate me. He told me to just relax and I did, and a few seconds later I felt the head of it starting to part my ass, and then the head slipped in and he got fully on top of me. He didn't move at all for a little while, then he told me he was going to fuck me just like he would a first time girl, and I would love it.

He very slowly started making hunching moves, and with each one I felt him going deeper into me, it didn't hurt at all, and when he told me that I had his whole cock in me I was suprised at how good it felt. At the same time he started to slowly thrust into me, he started kissing my neck and my ears. I thought I was going to piss, he pushed into me hard, then made short easy, then short hard thursts, long easy ones, long hard ones, all the while kissing my neck and ears, I could feel his breath on my face.

I wanted to push back to him, but he weight wouldn't let me, he had his legs outside of mine and started stroking a little harder and faster. I could feel him breathing harder, then I felt his whole body tense up, and then with about a dozen good hard strokes that almost took my breath away, he finished fucking me.

He stayed right where he was and I couldn't help but squeeze his dick, he told me that doing that was telling him that I liked what he'd done, and he was right, I had liked it. After he started going soft he pulled out and got off, I just layed there feeling spent and weak, embarrassed, ashamed and didn't know just what to think or do next. But he said that he could tell that it was my first time, and I would feel a little undecided about things right now, but not to worry about it, I had found out something about myself. He said lets get dressed and have a cup of coffee. I couldn't really look him in the eye for awhile, but things soon started to wear off, and we started talking about where he was going.

Then I remembered I was supposed to be cutting grampa a load of wood, told him I had to get busy, and headed a little farther on and started cutting wood. I cut a little more than a load, and as I went past his tent I threw off some of it, he said thanks for the wood, and for making him happy. I went on to gramps knowing that I got fucked for the first time and had liked it, and was thinking that the next time a guy made a suggestion that I just might get fucked again.