My First Time and a Little More : Part 3 Anal

Previously in “My first time and a little more” and “My first time and more, part 2,” I related how my best friend, Sean, was enticed to suck his cousin’s dick, but the cousin didn’t suck him in return. Sean asked me the next day to suck his dick, and we ended up sucking each other regularly for three years until I moved away. In the meantime, another boy, Michael who was three years older, moved into the neighborhood, and we all three got together to suck each other. Read the stories above to find out about those exciting, naive three years.

After I moved away from Sean and Michael, there was no one I felt close enough to explore sucking dicks with. I wasn’t aggressive like Sean, and I would never have asked to suck someone without really knowing them for a long time. I wasn’t shy as much as I was cautious about being exposed. In my first story, I related how Sean and I were naive and didn’t consider our relationship abnormal. Well, after three years of sucking each other’s dicks and maturing, it became apparent that sucking dicks with your friend is not to be discussed, but rather, it is to be hidden.

We moved to a farm far away from my neighborhood and friends, Sean and Michael, and there was no one my age near. A couple years went by, and I hadn’t had sex with anyone since Sean and Michael. Those were lonely years. Jerking off was routine, and I learned to fantasize about some of my friends at school but I missed my suck buddies. When you are young, you are resilient, so while I missed Michael and especially little Sean, I didn’t dwell on it. I had great friends at school, but we didn’t visit each other. Looking back, I see that I wasn’t at all like Sean. Sean would have asked a guy to come over for the weekend to play games and watch movies. We were at the transition age when a sleepover visit was just not cool. Geez, my friends were dating, so they weren’t thinking of sleeping at some guy’s house on the weekend. Sean probably could have pulled it off, but I just couldn’t.

One day, I got appendicitis. While recovering in the hospital, a male orderly named Lee stopped in my room. He reached out and tapped my dick but acted like it was an accident. I smiled which cued him that I didn’t mind. Just as aggressive as my old friend Sean, Lee bluntly asked if I had ever been sucked. I said yes. He took my dick out and sucked it briefly but not very long because someone could have come into the room. Wow, was that a surprise! That was the first time my dick had been sucked in two years.

There was no privacy in the hospital, so we made plans to meet up after I got out. I was initially reluctant because Lee was several years older, probably in his mid twenties. Lee lived 30 miles away from me. Since I had just started driving, I couldn’t just leave with the car for the length of time that it would take to get to Lee’s and to visit. My parents would ask questions. I wasn’t calculating enough to make up a story, so I decided to go to Lee’s after my piano lesson on Wednesday.

On a Wednesday after my piano lesson, I went to Lee’s apartment for the first time. He didn’t hesitate to start undressing as soon as the door was closed, and I got naked too. His dick was smaller than mine and was about 5 inches, but it was fairly thick. He was also not circumcised, but I didn’t notice that until later since he was completely hard. I had never seen an uncircumcised dick before. Since the only hard dicks I had ever seen before were Sean’s, Michael’s, and mine, I now had something to compare them with. Since Sean hadn’t matured the last time I saw him, I had only myself and Michael’s dick as reference. Lee’s dick was different from Michael’s and mine, but it had a nice symmetrical head and very hairy balls underneath.

He briefly sucked me as I was standing naked, and then he asked me if I fucked. Well, I had absolutely no idea about anal intercourse whatsoever. Let me repeat, I had no idea. To me, fucking meant sticking your dick in a girl’s pussy. Sean and I used to stick our dicks on each other from the rear as we were lying down to tease each other during foreplay, but we had absolutely no idea that you could actually stick your dick all the way inside. If we had a clue, believe me, Sean would have been the first to try.

Anyway, when Lee asked if I fucked, I told him yes and thought this was simply part of his foreplay. He told me to lay face down on the bed with a couple of pillows under my pelvis, and then he got on top of me. He teased me by caressing my ass with his dick. He used his dick to caress me all over my buttocks. Then, he stuck the head of his dick just a tad into me. I pulled away thinking that he didn’t mean to do that. He did it again, and I resisted and moved kind of forward so his dick wasn’t inside of me. Then he pinned my pelvis to the bed with his hands so that I couldn’t move around and pushed just the head of his dick inside me, and I squeezed it out. He repeated this a few times. Dang, I wasn’t expecting that. Talk about a true virgin, I was shocked to say the least.

Lee must have used a lubricant because as tight as I was, he was able to push his dick into me as I resisted. I kept trying to pull away from his thrusts and squeeze him out, and he continue pushing his dick in. He started pumping, and I got the idea that this could actually be done. So I stopped pulling forward, and I lay there feeling somewhat helpless to resist but not abused or anything like that. It hurt. It really hurt. Yeah, it really hurt a lot, but it was bearable.

Lee sensed fairly quickly that this was new to me. He gave me innocent advice while he fucked me. He said to push out slightly and relax. Easy for him to say, but I managed. He told me that he was going to go in further just before he thrust his dick all the way in. It wasn’t a warning for me to get ready, but rather it was a bit of playful sadism because he thrust his dick all the way into me at the very same time that he warned me.

He paused while holding his dick firmly inside of me. That was good. Finally I was able to relax a little. The moving in and out is what made it difficult, if not impossible, to relax. As he paused with his dick all the way in, the aching sensation eased off a bit. He told me to try to push him out, and that gave me a little more relief as I squeezed as hard as I could. I continued trying to squeeze him out and I tried to relax my muscles as he held his pelvis hard against me with his dick pushed all the way inside of me.

I remember experiencing his hair on my buttocks while his hands held my pelvis down. It was very sensational, but none of the good feelings overcame the aching during my first time being fucked. As Lee continued working his dick back and forth inside me, he paused once again with his dick all the way in. I was beginning to be more relaxed. Then suddenly, he pulled his dick his all the way out really quickly. Then he edged it back in. I thought I was going to die.

I told him not to take it all the way out again since I lost my relaxation and my muscles tightened up again. I tried to relax all over again, but this time I couldn’t relax because Lee was thrusting faster in order to force his orgasm. He wasn’t going to pause inside of me again until he came. I had my eyes closed at this point hoping he would stop soon. I was gripping the pillow with my hands and biting it with my teeth. I was pretty tough and I wasn’t a wimp, so I didn’t yell, grunt, protest, or say anything. I was completely quiet for the time it took for him to cum. I watched the alarm clock next to his bed, and he had fucked me over 10 minutes.

He continued to fuck me fairly fast until I felt his cum squirt inside of me. He pushed all the way into me and held his dick firmly inside of me as I felt about 5 or 6 squirts. Well, it could have been 8, I wasn’t counting. I was just trying to survive. His cum was warm as it pulsed into me. I enjoyed that feeling very much and remember it vividly.

Holy gosh. I remember thinking, wow, I had just been fucked! I didn’t like the sensation except for feeling Lee's warm cum squirting inside me, but I was always logical and reflecting after encountering something new. That moment was just about as mind-altering and profound as the first time that Sean sucked me over 5 years ago at which time I experienced my first orgasm. I just couldn’t believe a guy could fuck me! Looking back, it was great that I didn't know that this could be done. It was so exciting although I ached badly.

Lee held his dick inside of me for at least 30 seconds or more after he came. It seemed like a long time. I relaxed a bit. He knew how I must have felt because he pulled his dick out of me very, very slowly to allow me to adjust back to normal, if that was possible.

He was very considerate at that point. He gently pulled me to a sitting position on the side of the bed and put one of his arms over my shoulder as he sat next to me. He kind of nudged me to stand up and escorted me slowly me to his bathroom. His bath was very tidy, and it had the scent of a tasteful cologne, but I don’t remember the name. I stood in front of the mirror with both hands supporting me on the vanity. I thought I had fooled him into thinking that it didn’t hurt me as bad as it did. He brought me an ice cube. Then he shut the door to give me some privacy. All of this time, Lee hadn’t said one word. He knew what had just happened.

It was my first time getting fucked, and it was also the first time a guy had shown affection for me. At that time, I didn’t see that as a milestone, but reflecting back to that very moment, it was very significant to be the object of attention. I didn’t have friends old enough to live on their own, so I suddenly felt very mature and independent since I was treated as an equal in an adult’s apartment.

After I cleaned up and went back to his bedroom, he put Vaseline on my dick and laid on his stomach. He didn’t say anything and gave no directions. He just waited for me to insert my dick inside of him. I pushed my dick into him all the way. I had no technique since this was my first time. It felt good, but the new sensation from my anal area after being fucked prevented me from getting an orgasm. Yes, I know many people brag that they are turned on after having anal sex, but my first time gave me sensations that didn’t translate into sexual arousal. I developed that a long time later, but it just was not there for me now. I was a guy who just lost his naivety as well as his virginity. It was getting late for a school night, and I had to drive 30 miles. I didn't care. When I got home, my parents were watching TV and didn't ask about my coming in so late after my piano lesson.

It would take me time to adjust to these new feelings. After I got home, I jerked off using Crisco heated in the microwave just like Sean did years ago. The next day I was surprised that I was not sore at all. I was able to concentrate at school, but I did think about being fucked that whole day. Geez, I dwelled on it the rest of the week. I wasn’t in love, but I knew that I had changed.

Before I saw Lee again, I practiced getting fucked by inserting a lubricated brush handle in my ass each morning before I went to school. It was along ride home on the school bus, and I couldn’t wait to get home after school to practice again before jerking off. It didn’t take long before I was inserting the handle inside of me while I was jerking off. I really wanted to get the hang of this before I met with Lee next Wednesday. I thought of Sean as I discovered this new technique and wondered if he had been fucked yet.

It may have helped a little to practice at home, but each time Lee fucked me, I was relieved when I felt Lee’s cum squirting inside of me, and I couldn’t wait for him to pull out. So you might say that I enjoyed allowing Lee to get his pleasure while fucking me, but the sensation of being fucked was not sexually arousing to me to a great extent. Over the months that followed, each time Lee fucked me, I had a choice of fucking him, jerking off while he fucked me, or getting sucked after being fucked. I kind of rotated. Don't ask me why, but I didn't like fucking Lee as much as getting sucked or being jerked off, so after I while I stopped fucking him.

Lee liked if best when he jerked me off while he fucked me. It wasn’t my favorite, but I eventually let him do the reach-around method using a lubricant more and more. Lee knew I liked being sucked so he would start sucking me, and then after he got me going, he inserted his dick into me and reached around to clasp my dick with his lubricated hand.

I got to say that doing it together was easier than lying face down. It takes your mind off the pressure in your anus. Lee would regulate how he jerked me off so that he could cum before me. Sometimes we would cum together. That was a treat.

He always put a towel out before we began so that my cum wouldn’t get on his sheets. That was better for me, and he knew it. One time I came before he did, and I blew cum so hard that it went beyond where he put the towel. I was kind of proud, and Lee didn’t say a word. I cleaned it up after he came inside of me. Lee started using three towels in front of me after that. Eventually, I learned to control myself after being fucked so that I didn’t have to run to the bathroom afterward. I was proud that I could make it all the way home without stopping at a restroom. Such little milestones made me feel very mature at this influential age.

I craved Wednesday’s and craved to let Lee suck me, fuck me, and jerk me. I was growing up, but I hadn’t fallen in love even after experiencing Lee’s affection for me. To me, sex was still a fun game. After all of these years, I still missed Sean. I met Lee in the fall, and I continued to see him just about every Wednesday until the next summer when I starting working as a waiter for the summer and met another older guy.

Please read “My first time and a little more part 4” if you would like to continue this true story and find out another first time episode that occurred in the summer.