Chapter 1: Teenage Explorations

I have always been a very sexual being ... For as early as I can remember I was fascinated with “private parts”. Both my own and those of others. At first it was the private parts of anyone, and then once I discovered girls, theirs private parts especially interested me, this was long before the internet, and pornography was hard to come by, especially for a pre-teen. I had found a magazine in the woods near a local trailer park that our land backed up to, and hid it away for my own reference. Most of the women displayed in it were shaved ... Which was very eye opening, and revealing.

When I was 14 my friend Eric and I spent a lot of time at each other’s houses. Usually on the weekends, Friday / Saturday night sleep overs etc, usually at his house. His parents were often out on Saturday, going to town, running errands, etc. because his dad worked during the week. They would normally take his younger sister with them, giving us time to explore the woods, creeks, barns, and fields in a fairly large radius around his house.

We would discuss everything, but most prominently ... girls. He had an older sister that I spent a lot of time admiring, she wasn’t around every evening I was there, she would go out, doing things with her friends most weekend evenings. I had managed to sneak a few lingering views of her in just a bra. She was very large breasted, even at 17 years old, the way her breasts moved beneath her clothes was a constant fascination for me. And I saw her once in her bra and panties ... That mental image was a source of material for self pleasure for quite some time But that was the most exposure I had ever had to a “not completely dressed” female form. Girls in bathing suits of course, but seeing her in her underwear made me tingle, made my cock hard, made me short of breath...

Eric and I were both very interested in sex and increasing our knowledge of it. We were pretty open with one another as I look back on it. We both knew the other masterbated, and we had seen each other naked on occasion, skinny dipping in creek, showers at school. So it became a matter of habit when we were alone in his room that we would masterbate in front of one another, it was a forbidden thing, so of course it was far more attractive to us ... This led to the suggestion that we use our hands on the other ... Which we did ... I will admit getting to touch someone else’s equipment was a turn on, we tried it with vaseline, which was an incredible feeling. We had a lot of discussions about girls doing it for us ... How it would feel for them to touch us.

One day when we had just finished a session, Eric mused about what a cock would taste like. We knew that men went down on women, and that women did the same for men. I replied that I had no idea, but he could taste mine if he liked. He looked at me with a shocked look on his face, but I think that was for my benefit, I really felt like he was fishing for me to offer. He asked me to take off my shorts, which I did, and he got down very closely to look at my cock. It was about 4 ½” long at that time, and it grew longer as I grew taller. He held it in his hand ... spent some time sliding his hand back and forth, and then touched the crown with the tip of his tongue. He must have liked the taste, because his next move was to take as much of me in his mouth as he could. This wound up being nearly all of me. I was amazed! He told me later that he experimented with a carrot that he had washed extensively. He was a natural ... He started sliding his lips up and down the shaft, stopping before the crown slipped past his soft lips, and then eventually sliding down until I felt the head bump the entrance of his throat. It felt better than anything I have ever had done to me ... I was a fan of having my cock sucked to say the least. He continued on for about a minute ( maybe) and I felt myself about to cum, which I told him, he kept right on sucking, and I warned him again, eventually I could not hold back anymore, and I filled his mouth with my cum. He leaned back, smacked his lips and said that I tasted good, and that he wanted more soon. Then he asked if I would taste him.

I moved around and stroked his cock til it was hard. It wasn’t nearly as long as mine, but I took a couple of experimental licks ... It didn’t taste bad, so I took it into my mouth and started sliding my lips up and down the shaft. It wasn’t gross like I had built it up to be in my mind ... I wasn’t exactly a fan, but if it led to him sucking mine again, then I would do it! After about 30 seconds I could feel his cock start to pulse, and he moaned that he was about to cum ... I kinda backed off a little bit, and held just the head in my mouth, and I felt him start to cum ... Several small pulses ( about what he shot when we would masturbate ) and the taste wasn’t bad, but I didn’t feel the same way about it that Eric did...

So for the next few weeks every opportunity to have time alone we would wind up masturbating each other or more often, with my cock in Eric’s mouth ... He knew I didn’t feel the same way about it that he did, but the fact I was willing to let him suck me was all he needed to do so at every opportunity. So that was normally what would happen, we would get naked I would lay back on the bed, and he would get between my legs and start sucking ... licking up and down the shaft and occasionally licking my balls. He was becoming quite good and could take my entire cock into his throat. I usually didn’t last very long after that happened. When I would start cumming, he would pull back so that I came in his mouth. He loved the taste of my cum.

One of the things we started doing was taking a towel with us whenever we were off adventuring. We kept the towel, a container of vaseline and some old washcloths in a backpack that we had dug out of an old garage in the neighborhood. We would find a secluded spot in the woods, and lay out the towel ... Normally I would lay back on the towel and he would get between my legs, und zip my pants and pull them and my underwear down, then he would eagerly use his mouth on my cock. There were infrequent times when he would ask me to go down on him, and if it meant that he kept on wanting to suck on my cock, then I was willing to do it. I got pretty good at making him cum with my mouth as well ... It usually didn’t take very long, especially if we had been talking about sex and girls.

We discovered that it felt even naughtier ... more forbidden, if we were both completely naked. Usually Eric would suck a couple of cums out of me, and I would use the vaseline to masturbate him. After we both came, we would lay on the towel and talk about anything and everything. During one of these times Eric casually mentioned that he had been sliding a carrot into his ass, and that he really liked the way it felt. We discussed that some, I asked why he decided to do that, and he replied that he had seen his sister using a carrot on herself, and she had cum several times. Since she had enjoyed something penetrating her so much, he decided to try it. Of course I asked how many times ... How large was the carrot. Did he get hard when he was doing it ... etc.

As he answered the questions I was getting more and more turned on. The carrot started off about the size of a dime ( he had trimmed the tip and rounded it some ) and wound up being a little larger than a quarter. He said he had only tried it a couple of times, and each time he had cum very quickly. The first time he slid the carrot in just a little way after lubing it with vaseline. A couple of inches or so ... The second time he had been braver and had kept working it deeper and deeper until it must have touched what I now know to be his prostate. He said that it was almost to the largest part when he had a funny feeling and started cumming like a garden hose. From the way he was telling the story, I could tell he loved the feeling of having something in his ass. I asked if he was planning on doing it again, and he said “yes”, then he added that he had brought the carrot and asked if I would like to watch him do it? I replied “YES!” This was something I wanted to see very much.

So he dug around in the backpack and brought out the carrot and the vaseline container. Opening the container, he got some on his fingers and ran them up and down the carrot, then turned over on his hands and knees with his butt in the air and started working the tip of the carrot back and forth across his rosebud. Finally centering on it and slowly starting to work the tip into it. The whole time telling me that it tickled and that he could feel it starting to stretch him as I watched it begin to slip inside him ... A quarter inch, then a half, a full inch, another half inch, and finally 2 inches ... his anus starting to stretch out around it. At this point he started to withdraw it and then slip it back in ... gaining a little depth each time ... I was fascinated ... Watching it go deeper and deeper inside him ... The carrot was about 8 inches long overall, and by this time he had 3 inches embedded in his ass and was working more steadily inside himself. I asked if it hurt, and he said only if he clenched down, that if he relaxed it didn’t hurt at all and it was starting to feel really good. He continued to slide the carrot in and out of his ass ... Still going deeper... 3 1/2 inches, and then halfway. I don’t think I was even blinking, and pretty sure I forgot to breathe for a while there. Then he asked if I wanted to hold the carrot and slide it in and out. I said “yes” and he had me grasp it with my hand before he let go so that it wouldn’t escape ( he had learned that if you let go, it would quickly slide out ). Once I had control of the carrot he asked me to go slow, but to keep working it in and out and deeper.

As I started working the carrot in and out of his ass, I began making longer strokes ... It seemed like the longer the stroke was, the more he moaned ... I finally had three quarters of the vegetable inside him, which was pretty much the largest part of the carrot, and Eric started shaking, and then cum poured out of his cock and hit the towel he was kneeling on ... I slowed down a little ... But kept moving the carrot in long slow strokes ... When I asked if he wanted me to stop, he shook his head “no” but never stopped moaning. The whole time the carrot had been in his ass from the very beginning, his cock had been hard, even after cumming it didn’t seem to soften. Since his answer was “no” to the “do you want me to stop”, I resumed working the carrot in and out at my original pace, but still working it deeper while making sure to keep enough outside to keep a grip on. It would seem that I was probing back and forth past his prostate, because it was only a couple more minutes before he was shaking and cumming again. He more or less collapsed forward on his folded legs, and started repeating “stop” “stop” “stop”... “ I can’t take anymore right now” ... So I slowed to a stop and gently withdrew the carrot from him.

Over the next few weeks this became the normal scenario for us, it was springtime and since we lived about a mile apart as the crow flies, we would meet near the midpoint between our houses in the woods. Afternoons after school, and Saturdays and Sundays. We would strip down, Eric was always eager to suck my cock and I was always eager to let him. After the first blowjob it became a ritual that I would use a carrot ( or a small cucumber a few times ) to fuck his ass. Until he came at least once, and usually twice. Then once he recovered from his orgasm he would give me a second blowjob. I guess it would seem like it got somewhat routine and boring, but it was anything but ... It was very easy for me to get lost in thought about how good his mouth felt on my cock ... how good it felt to cum down his throat. At the time I didn’t give much thought to it being homosexual ... I just knew that the sexual itch that I had been having for so long was finally getting scratched, and it was getting scratched regularly!

When we got out of school for the summer, we spent a lot of time adventuring around the community ... There were not neighborhoods like we think of them today ... There were houses along the roads, both paved and unpaved roads ... There was a large creek that we sort of used as a boundary, though we did cross the train trestle and explore beyond at times. We would fish in the large creek and any number of smaller creeks and streams that had water in them depending on when the last rain was. And we spent a lot of time naked and involved in sexual activities ... Remember, there was no internet at that time ... No cell phones ... No computer images ... Heck I had only used a computer a little bit at school in a class, and it was monochrome and text only. So ANY sexual activity was fascinating and awesome. We would talk about girls, which I was VERY keenly interested in. Eric would tell me about seeing his sisters in various states of undress, which always kept my full attention, and usually gave me a hardon, which he was happy to make use of.

Mid summer we were at our hangout near the midpoint between our respective homes, we had constructed a “fort” mostly for the purpose of being able to hear and see someone that might approach while we were “occupied”. Fear of getting caught was a real thing, but not enough to stop us. Also realize that this was a different time, parents didn’t worry about us being abducted ... If we did something wrong where another adult could see us, it was likely that they would discipline us, or at the very least our parents would know. So when I would tell mom that I was going to meet Eric, there was no concern unless I didn’t show up by supper time. Then at the least a call would be made to Eric’s house to see if we were there, and to inform me that I was supposed to be home. This was suspended if I had been invited to eat with his family, or if he had been invited to eat supper at my house.

Anyway, this particular day in late June we had arrived back at the fort after something of a trek and he had been telling me about seeing his older sister’s bare breasts, which had me very worked up. After we checked the fort for snakes and small animals, I was laying out the towel and started to undress when Eric mentioned that he didn’t have a vegetable that day to use as a toy. I replied that we could go to my house and see what we could find and sneak out. Then he suggested that we could combine the two things. I was a bit confused and asked him to explain. He said that I could use my cock in his ass, that way I would get to cum and he would too. At first I said “NO”, but he kept working to convince me. Offering to get me hard with his mouth, lube me up and then I could get behind him and slide into his ass. I would be lying if I said I had not thought about doing this before ... But I didn’t want to admit it, especially out loud. So I let him think that he won me over to the idea and agreed to give it a try.

We both undressed and Eric smeared some of the vaseline around his rosebud and pushed some inside, then turned and looked at my cock. He commented that I must like the idea because I was as hard as he had ever seen me and then took my cock in his mouth. He backed off after about 10 seconds, my cock wet with spit, he applied vaseline to me, and then spun around, stuck his ass in the air, and put his head down on his arms. I moved forward and rubbed my dick up and down his crack sliding back and forth over his anus. I said “are you ready”, and he shook his head “yes”. So I aimed the head at his anus, the first contact was electric, the tabooness of touching someone else’s intimate area with my private parts was nearly overwhelming. I paused with the crown touching, and he started to push back. At this point Eric’s ass had been penetrated by vegetables almost everyday for the past 3 - 4 months. So he was used to having his ass stretched. When he pushed back, his asshole opened up and swallowed my cock ... I wasn’t inside him, and then a very tight and hot ring was around the shaft of my cock just behind the head. He stopped at that point, I guess to give himself time to adjust to the intrusion, kind of wiggled his ass and I started pushing forward as he moaned at the penetration. The grip around my cock was amazing ... I had never felt anything remotely as good. So hot ... So tight ... Like a velvet wrapped glove squeezing my cock for all it was worth.

I slid in until my hips were up against his skinny butt cheeks. Completely buried to the root of my cock in his ass. I could feel his anus clenching me as we held there, not moving. We stayed in that position for a couple of minutes, Both of us amazed at the sensations, then at some unspoken signal we started to move. Small movements at first, slow shallow strokes, then more movement, until finally I was pulling back til the crown of my cock was pulling on his anus, and back in until I could feel him gripping the base of my cock. I could feel something deep inside him against the bottom of my cock, and everytime I touched it he moaned. After a couple of minutes of this Eric moaned even louder and I felt his stretched rosebud start to pulse and then clench tightly around my cock, and he came, and came a lot. When I was able to start stroking again, I made it about 4 strokes and then came deep in his ass. Emptying myself inside him until I didn’t think I had anything left in my balls.

When I withdrew, we both collapsed on the large towel that I had laid out. Both of us were completely spent. I was breathing like I had run a mile, and I think Eric actually went to sleep or passed out for a little while. We finally recovered ourselves, cleaned up with the old washcloths that we had. We were both still kind of stunned at the intensity of the encounter. When we finally started talking, Eric couldn’t stop talking about how intense it was, how it felt, how hard he had cum, how much he enjoyed it, how much better my cock was than a vegetable! For my part, I had never felt anything so good ... it was far better than my hand, way better than his hand, and better yet than his mouth, though that was pretty close. But the grip, The heat, the tabooness of the act of fucking his ass. All combined to make it a landmark experience for me. I still wanted to do sexual things with girls, but until one decided I was worthy, I was a fan of Eric’s ass.

An ass that was sore the next day, so we hung out at the fort and took it easy, he gave me a blowjob and I jerked him off, both were still very satisfying but I new bar had been set for sexual activity. The following day he suggested I let him fuck my ass. He had used a vegetable on me a few times, but I don’t think I got the same sensations of thrill out of it that he did, I enjoyed using a carrot or cucumber on his ass way more than having one used on me. However, in light of how much he enjoyed it, like the blowjobs that I had given him on the infrequent occasion. It wasn’t something that he asked for very often, he really did seem to enjoy giving them more than receiving them. So with the idea in the back of my mind that doing so would lead to getting to fuck his ass more, I agreed. Getting undressed, I got on my knees and put my shoulders on the towel, turning my face to the side, which had the effect of putting my butt in the air for his access. He lubed me up with vaseline, first on the outside of my anus and then started working a lubricated finger into my ass, then two fingers ... He worked the lube into every nook and cranny of my ass, and then he removed his fingers, and brought his slick cock to my asshole, and began to push his way in. I had learned from having my ass penetrated by the vegetables to relax, and push out, and the veggie would slide right in, so I did the same thing now, my ass was somewhat loose from his fingering, and once I relaxed he began to slide inside me. He slowly worked his way inside me, he was a little longer now than when we first started, maybe 4 inches. He stopped when the head popped inside, I guess remembering that he had to get used to me in his ass. Then he asked if I was ready for more, and to answer, I started pushing back onto his cock. He started to push forward, and pretty soon I felt his balls against mine. He was all the way inside and I could feel his cock head brushing something inside me and when it did my cock would jump and get even harder than it already was...

Eric began sawing his cock in and out of me, I didn’t get a lot of sensation of having my ass penetrated, it didn’t really hurt, I didn’t get that much from it, but when he would hit my prostate it made my head swim. He didn’t hit it everytime, maybe once every 4 or 5 strokes. This had my cock like a steel bar. Those bumps finally added up to making me orgasm. When I came, I apparently clenched down tight on Eric’s cock, and shortly after shooting a huge load of cum on the towel under me, he filled my ass full of his cum, then slowly slid his cock out of me, and we both collapsed on the towel to recover.

We laid there for a while until our breathing slowed some, and Eric Said something that surprised and relieved me. I think I like you doing that to me better than I like doing it to you. I was of the same opinion, I got way more enjoyment out of fucking him, than I did from him fucking me, at least at this point. Eric got on his knees and moved between my legs, putting his mouth on my cock and taking me as deep as he could ... Which was the whole way ... I watched as he did it, and his nose touched the skin on my stomach. My cock was rock hard again almost immediately, and he began to bob up and down on it. After about 15 seconds, he lifted off my cock and turned around and raised his ass in the air. I asked if he was too sore from yesterday, and he replied yes and to fuck him anyway. I grabbed the vaseline, lubed his ass throughly, moved in behind him, and for the second time in 2 days I slide balls deep into his ass. He moaned and asked me to go slowly, but when I pulled back to the crown of my cockhead, he would start pushing back onto my shaft.

I fucked him slowly for a couple of minutes, then sped up until my balls were slapping his so hard it was slightly painful. I was holding his ass cheeks apart to give me more access, and could see his anus sliding all the way down to the base of my cock. For some reason that was a huge turn on for me ... I guess to know that I was making him take all of me. After just a couple of minutes of sex at that intensity, I felt Eric’s ass start to clench me and knew he was cumming, then I head the wet splatter below as as he ejaculated ... That was more than enough to cause my orgasm as well, and I filled his ass full of my cum. I sat back on my heels and watched his ass gradually close up, capturing my entire spend inside him.