Many of you have written about my first anal experience in an earlier story segment. Obviously it wasn't the greatest experience, and I wasn't anxious to repeat it anytime soon. After about a year and a half, though, I did actually get it up the ass again. Although this second time wasn't all that fantastic, it was a little better than the first. At least I knew a little about what to expect. Again, this is a true story.
College Town Kid Figures it Out Pt. 10
"The Second Time To Get Screwed"
Now I was about 19 or 20, I don't remember for sure, but I was a college freshman. I travelled home some weekends to see family, and then would return for classes on Monday. In order to do that, I drove through a major midwest city, which had a couple of adult bookstores in it. I had seen one right off of the interstate, and so I decided to check it out on my way back to campus on a Sunday evening.
It was almost empty when I went in, and the video area was in the back, up a short flight of stairs. It was spacious and well lit, which was different than the other adult bookstores that I had been in. I picked out a booth, and started watching a film. After a couple of minutes, I heard the door next to me open, and I peeked through the hole. I could barely see the guy who had came in, so I exited my booth as soon as the film started.
I casually watched from the end of the hall when he came out of his booth. He didn't look bad at all. Brownish red hair, a little bit of beard scruff, brown eyes, and probably in his mid to late 20's. He looked pretty clean, and dressed preppie and I figured he was a college student.
I went in a nearby booth, and left the door open slightly. After the film started, I saw him standing right outside the door, and I pushed it open a little further. He got the message and slipped in.
"How's it goin'?" He mumbled. "Ok, here," I whispered back, and inserted a token in the video. We both watched as I flipped through the channels until I found a gay flick. "Do you want to come over?" He whispered, "I'm not too far away from here..."
(Here I was, once again with a total stranger in a strange city, and I agreed to follow him home. Geesh- it's a wander I survived!)
He told me to leave my truck, and that we would come back later to pick it up. His car was pretty nice, and still had that new car smell to it. As we drove, he reached over and rubbed my leg, while we made small talk about college, and such. It turned out, he was some kind of medical student. I never could figure out if he was interning, or what level he was at, but it had to do with med school. I saw hospital clothes tossed in the back seat, so I thought that he may have stopped at the bookstore on his way home.
We pulled into an average apartment complex, and I followed him feeling like I was a puppy in heat, or something.
When we got inside, he poured some type of alcohol for me, and refilled it after I downed the first shot. I was a little bit nervous as to what was going to happen next. After about three or four shots, I was starting to relax.
"So what do you like to do?" he asked.
"I guess I'm up for about anything," I replied, sounding pretty naive.
"Anything special?" he asked.
"No, I guess whatever you like will be good with me," I said as I downed another glass of liquor. I was really feeling the booze, now, since I rarely ever drank anything alcoholic.
"Let's get undressed and go in the bedroom,then. Is that ok with you?" he asked, while starting to pull off his sweatshirt.
I followed him into the bedroom, undressing as I went.
I watched him as he finished taking off his pants, then his shorts. He had fine, curly brown hair all over his body, with some freckles scattered around, and he was small to medium build. His cock was hard, and was about 7", cut. I knelt down in front of him, and took it in my mouth.
It tasted good, and I took it all the way to the base, holding it in my mouth and throat for a moment, then beginning to slowly take it in and out. He rubbed my head and his hips slowly pushed into my face.
"You like my cock, don't you?" he murmured, in almost a purr. "Here, lay down on the bed."
I laid down on my back, and he said, "Roll over for me, ok?" I rolled over, and he traced his finger down my spine and into my crack, then parted my butt cheeks. "You have a nice ass," he said, then reached down and licked up my crack. "Mmm. Very nice."
I was thouroughly enjoying this new experience. I had never felt a tongue on my hole before, and with the alcohol in my blood and his mouth on my butt, I was soaring.
He reached over to the nightstand to some kind of liquid and squirted it on his finger, then started rubbing his finger around my hole. I think now that it might have been some kind of numbing agent like lidocaine, because I didn't feel much until I knew that his finger was inside me, gently probing me.
"Do you like this?" he murmured.
"Yeah...feels good," I whispered back.
"You ready for my cock inside you? Hmmm?" he asked, while rubbing my back with his left hand.
Boy, I had made up my mind that I would NOT be fucked again. Been there, done that, and it wasn't that fun.
"I dunno....I did that another time and it wasn't too good. I'm a little nervous to try it again. Maybe we can do something else...." I almost pled with him.
"Sometimes the first is pretty painful...but I think you'd like the way I do it. I can be very gentle. Can we just try something?" he said, softly, "Lay sideways, facing the other direction, and bend your knees up a little."
I rolled over, feeling like I was in a doctor's examining room and thinking to myself, "I'm going to regret this'.
"Yeah, that's it. Now I'm going to lay sideways behind you, ok? Just relax..." he said, as he laid down sideways behind me, near the edge of the bed. He wrapped his arms around my chest, and pulled me close to him. "So far you're ok, aren't you?" he whispered in my ear, then kissed it.
"I'm ok." I answered, still a little giddy from the booze.
"Good, now just relax a minute," he said, as he reached down and positioned his cock. I felt him probing my ass, until he found what he was looking for. With his left hand on my hip, he held me firm and pushed. Instantly I felt pressure on my hole, and knew he had entered me. Apparently the cream or medication he had applied, must have numbed me, because there was only one sharp quick pain, and then no pain hardly at all.
I could feel his size inside me, as he finished pushing in. "I'm all the way in, Reid," he whispered in my ear. "How's it feel?"
"It feels ok..." I answered. "It doesn't hurt very much at all." I lay there, just enjoying the feeling of this young guy huddled next to me, arms around me, and attached to the insides of my body. It felt intimate, for a moment. I could feel the chest hairs against my back and his legs against my legs.
"Now let's try something," He said. "I'm going to move around in my position and you rotate until your on your back, ok? Just go really slow..."
He started to move, and I felt his cock twisting inside me, trying to rotate around inside my body. Instead of the cock twisting, I felt like me insides were twisting. It was too tight to work.
"I don't think I can do it....it's too tight" I groaned, hoping he would stop. Unfortunately, he was already over halfway. He hesitated a moment, with my left leg now over his shoulder.
"Let's stop for a second and catch up, ok?" he questioned, like someone in an anatomy class. "You'll be ok, don't worry." His cock slipped partially out of my hole, and the rotation seemed to work. When he had my right leg on his other shoulder, he pushed quickly until he was all the way back in. "We made it," he said, "It's all the way in." Whatever the rotation trick was, it had definitely loosened my hole up, some.
I was now on my back, looking up at him, feeling very full. There was a lump in my throat. I felt very vulnerable, but the pain was only slight. My cock was very hard.
He reached down, pushing my legs closer to my chest as he went, until our faces touched. Instead of just kissing me, though, he pushed his wet tongue in my mouth, and just held it there, as his hips ground into my ass.
I always kind of liked kissing, even when it was with girls- and guys usually turned me on, too, even though their kisses were a lot different. But this wasn't as much a kiss, as a wet tongue fucking my mouth. I was turned on by this guy, but I wasn't sure about this experience. But he definitely was enjoying it.
He finally pulled back, leaving plenty of saliva on my lips and face, then took hold of my ankles and said, "Are you ready to get fucked?"
Not knowing how to answer that questions, I just looked up at him. Apparently he didn't need an answer, because he pulled slowly out and then shoved his cock all the way back in. I could feel the momentum pushing me into the mattress, but it really didn't hurt that much- just a little pinch like feel when he first shoved.
"Can I go on?" he asked, smiling.
"Yeah, I guess so...I'm ok..." I answered.
He began to pump in and out, and I closed my eyes and started enjoying the ride. It did feel kind of cool. I imagined his cock inside of me, and I even imagined what it would be like to be a girl, getting fucked. I opened my eyes as he leaned over again...ooo, here comes the tongue again. "He's really into this tongue fucking" I silently thought to myself, as a hard, wet tongue penetrated my lips and probed my mouth.
I still wasn't sure if I liked the tongue thing, but I at least pretended to like it. It gave me a little break from the screwing. Finally, he withdrew, and began to shove his cock in me harder, and faster than before.
I thought he was getting close, so I started thrusting back in response. It felt good as we got in a kind of rhythem, thrusting and withdrawing, thrusting and withdrawing. His groans got louder, and so I grunted and groaned, too, sure he was about to shoot his load.
This went on for a long, long time. After a while, I was starting to get a little tired, and felt more and more soreness. Embarrassed, I finally asked him, "Are you getting close, yet?"
He smiled, "I don't usually cum inside a guy. I'd rather he finish me off with his mouth. It takes a lot to get me to cum. You wanna change positions?"
"Yeah," I groaned, "I think I better. I gotta pretty major workout, here."
He pulled slowly out, and let my legs collapse on the bed. Then he laid down beside me.
"Wow!" he sighed, "That was pretty cool!"
I lay there a moment, then worked myself up until I was between his legs.
"Let me get it close, for you," he said, as he started masturbating himself.
I wondered how you could get sucked, then fuck for almost an hour and not be 'close.' But I laid my head on his thigh and watched while he jerked off. His cock looked much smaller than it felt when inside me. In a few minutes, I heard his breathing grown heavier.
"I'm almost there," he groaned.
I pulled myself up, wanting to finish him off in my mouth, but before I got in position, he was squirting all over his groin and lower chest. His hand was still jerking on his cock, so I couldn't get it in my mouth in time.
He finally stopped, and let go of his tool. I reached over and took his cum covered hand and held it to my mouth. For a guy that was scared to touch cum a little over a year before, I was pretty fascinated with it now. I licked the palm of his hand and the cum between his thumb and index finger, then reached over and began licking his chest and groin. It was thick and was starting to gel- an almost gooey consistency in my mouth.
Finally, I saved his cock for last as I gently took it in my mouth. It was soft and sticky, and still smelled like ass. I carefully extricated the cum that was clinging to it, then laid my head down on his thigh next to his cock. We lay there until I was almost ready to doze off.
"You wanna spend the night, or do you want me to bring you to your truck?" he asked.
"No, I gotta get going." I murmured back, not wanting to go at all.