A few weeks had passed since my first encounter with Jason. It seemed like we were settling into a more manageable schedule of once or twice per week. I was starting to enjoy being on the receiving end of anal as much as I was in giving it. I wasn’t sure if that was because Jason was on the petite side or if I was just that sort of sexual entity. I was hoping to expand my sexual horizons, but there were only two candidates that stuck out.

First of all, was, of course, Aaron. While he was easily my first choice, things had really cooled down sexually between us. It had been a couple of months, at that point, since we had experienced one of our encounters.

The other candidate was my friend, Todd. We had become close friends in our later high school years. He could also be a very complicated individual, though. Todd was an only child and was rather spoiled. He was also a bit of a germophobe.

As far as I knew, he had never had a girlfriend. He had either gone alone or brought a female friend to all of the school events. Of every guy in my class, he was the most obvious choice to be gay or at least be sexually adventurous. Well, other than the two that I had already corrupted, at least.

I had tried several times to initiate an encounter with him, but he was always quite standoffish. I suspected that his resistance was mostly a smokescreen. There were a couple of times that we had watched adult films together. He always seemed to want to be seated at the back of the room behind me. I was never quite sure if that was because he didn’t want me to see what he was doing or if he wanted to have a more subtle angle to see what I was doing.

On this particular day, Todd had stopped by the house for the afternoon. We hung out in my room for quite a while, both listening to music and playing video games. That was the usual activity when Todd came over. He never had a video game system at his house. I suspect that it was because his parents didn’t want him distracted from his studies.

A while after he had arrived, my parents headed out to a community banquet. I eventually coaxed Todd outside and we headed to the pole barn. He seemed confused when we walked past the four-wheeler and I opened a storage cabinet located in the back corner of the barn. I pulled out a motor oil box that was full of shop rags and then opened up another box of motor oil that was underneath it.

As I did, Todd’s eyes lit up. The box was filled with about fifty adult magazines. It was my dad’s porn stash. I would have never found it on my own. My sister, Sara, had found it somehow. She had a knack for finding things that people were attempting to hide. For some reason, she always felt motivated to share such things with me. Perhaps because she had been witness to so many of my unintentional displays of sexual angst.

I had only been aware of it recently and had only perused through it a couple of times. Inside, there was an assortment of standard nudie magazines, high-end adult magazines, and swinger magazines.

I carefully pulled a small stack of magazines out of the box and placed them on top of the box that we had removed. We each picked out a magazine and nervously shuffled through it.

After a few minutes of looking through our magazines, I placed mine back in the order that it was previously in. I searched deeper into the box and pulled out a few more magazines. There were several high-end magazines in that group. I found one with Asian girls that interested me and I quickly dove into it. Todd sorted through the stack and found an unusual one that seemed to catch his attention.

The magazine that Todd latched onto featured all sorts of lactating women, some were solo and others were sharing their bounty with gentlemen. He seemed to be quite intrigued by the magazine. I am not sure that he even knew that he was interested in such a thing before he actually saw it. He was clearly quite riled up at that point. His hands were shaking noticeably and he kept muttering “Oh my god!” and “Jesus!”

After we had sorted through magazines for about a half-hour, I told Todd that we needed to start packing things back up. I knew that we had a couple of hours before my parents would arrive back home, but I had successfully managed to get Todd worked up and I wanted to see if I could initiate something.

We headed into the house and back to my room. Todd couldn’t stop talking about the lactation magazine, which was exactly what I had wanted. It seemed quite clear that his mind was not going to be derailed from pervy thoughts very easily.

We both sat down on the edge of my bed and fired back-and-forth comments about what we had just seen. It was hard to hide the excitement that either of us was feeling. Todd’s excitement was a bit more obvious than mine, though.

My friend Todd was not the best-looking guy in my class by a long shot. He was a freckled redhead with skin that was a pinkish shade of white. He usually had a half-grown mustache that didn’t help matters either.

He was roughly the same height as me, 5’10”, but he probably weighed around one hundred and eighty pounds, which was about forty pounds heavier than me. I wouldn’t describe him as fat by any means, but he was pretty doughy.

Todd did, however, have one standout feature, which was the one that he was trying to wrangle inside of his shorts. Todd had a long, thick cock that had a blunt, pink head. In my class at high school, there were three guys with standout cocks, Todd was one of them. He was also the only one that I associated with or thought might be interested in an encounter with me.

Somewhere in the middle of our talk, I decided to pull out my cock and began to slowly stroke away. Todd acted freaked out and he slid away from me. I was not surprised by his reaction. I decided to not let that affect me and I continued on anyway.

Todd kept pointing out what I was doing as if I didn’t already know. I also noticed how often he was looking down in my direction. I told Todd that was what porn was for, you get excited and then get off.

A bit later he finally relented and started to unzip his pants. He pulled his cock out slowly and I tried not to stare as he swung it around and to an upright position. At that point in my life, it was the largest cock I had seen in person. It was over eight inches long and thick.

Once he started to participate in the masturbation session, I started to remove some of my clothes. At first, I kicked my shorts off and spread my legs out a bit. A bit later, I peeled off my shirt, as well. Todd kept his shirt on, but he did kick off his shorts also.

I stood up and turned so that I was facing Todd. We gave each other a look and then I made an obvious downward look at his cock. I slowly dropped to my knees. Todd started to lodge an unconvincing protest as he strangely pulled his hand away from his cock and placed both hands on his thighs. As I reached in and my hand wrapped around his cock, the protest stopped immediately.

I started to stroke his cock slowly. It was every bit as thick as Aaron’s cock at the base, but it did not have much taper at all. The thickness combined with the length had me doubting how far I wanted to go with this monster. It was also becoming increasingly clear that nothing that Jason and I had done would prepare me for the size of Todd’s cock.

The closer that I got, the larger his cock appeared to be. Todd’s sack hung low as it was weighed down by his large, prominent balls. From tip to balls, it must have been roughly a foot of manhood.

I leaned in and my tongue met him at the top edge of his scrotum. I slowly worked my way up the length of his cock. I could hear Todd’s jagged breath rattling the entire time. As my tongue explored the ridge on the underside of his cock and finished its first pass I could hear Todd sigh.

“Just let me know when you want me to stop,” I said sarcastically as I looked upward.

Todd retaliated, “Don’t you have better things to do with your mouth than talk?”

I wrapped my right hand firmly around the base of his cock as I wrapped my lips around the tip. I worked the two in tandem for a while as I rubbed Todd’s inner thigh with my left hand. Todd occasionally placed a hand around the back of my head, but he never forced me at all. It seemed like it was more of a gesture of affection than it was of aggression.

I continued on until I could tell that Todd was getting close. I was strongly considering making him cum in my mouth. I didn’t because I feared that it would be the end of our encounter far too soon. I wasn’t going to give up on the challenge that I had set for myself.

I stopped stroking and pulled my mouth away from Todd’s cock. I slowly stood up and told Todd to slide back on the bed. There was a brief, unplanned kiss exchanged.

I headed over to my closet and pulled out a condom and a small bottle of lube from my hiding spot. As I was scrounging around, I told Todd to take his shirt off. At that point, we were both stripped down to just our socks.

I tore the condom wrapper open and tossed it to the side. I leaned over the bed, placed the condom over the head of Todd’s cock, and started to slowly roll it downward. I could tell that he had never had a condom on before by his reaction.

Then I grabbed the bottle of lube and put a generous amount in my hand and slathered it all over his cock.

Todd was staring at me.

“Are you going to…”

I smiled at him and said, “Yeah, are you okay with that?”

He responded with a nod and a rather low, “Yeah.”

With that bit of formality completed, I coated my ass with the remaining lube that was left on my hand.

I climbed onto the bed and positioned myself in a squatted position over Todd. I grabbed his cock with my left hand and tried to lower myself down on it. After the first push, I was beginning to believe that it would not fit. It felt like he was striking bone on both sides. I began to wonder if my slender anatomy would even allow this to work.

After a couple of failed attempts, Todd broke the silence.

“Your ass is even tighter than I had imagined.”

I smiled down at him and said, “Busted!”

At that point, we decided to try something different. We both climbed off of the bed and I presented myself bent over the edge of the bed with my ass in the air. Todd grabbed the bottle of lube and gave my ass an extra squirt.

As he pressed the head of his cock against my ass, I started to force myself backward. As I did, he was pushing quite forcefully. After a couple of tries, it finally breached. I had absolutely no idea how deep it went inside of me, I just knew that it felt like he was going to tear me in two.

I cried out, “Oh fuck, oh fuck, oh fuck…” about one hundred times.

Todd asked if I wanted him to pull out, and I told him to leave it in. I thought that the strain would ease up after a little bit, but it only seemed to get more intense.

I finally surrendered and asked him to pull it out. It took me a couple of minutes to steady myself before I was ready for him to go again. Once I was ready, I gave him the signal. It still took a forceful shove to gain entry, but there was certainly less resistance.

It still hurt about the same amount as before. Once I had steadied myself, I gave Todd the instruction to start slowly. He gave a few slow, subtle strokes. He was quite considerate of my situation. Eventually, though, I had to beg off once more and get a bit of a break.

I growled at Todd, “Jesus! That is such a fat, fucking cock!”

He asked me if I had ever been fucked before. I admitted that I had been with one person a few times, but that he was much smaller. He immediately mentioned Jason’s name. I didn’t admit to or deny those allegations, but he clearly had a strong suspicion as to whom I was referencing.

I was ready for our third attempt and I was determined to fight through the discomfort. I crawled a bit further up onto the bed so that I was lying flat on it. Todd climbed up on top of the bed and lowered himself into position. He drove his cock inside and lowered himself down on top of me.

I could feel his body heat radiating against my back as his soft midsection pinned me down.

He started to thrust away slowly until I gave him permission to be a bit more aggressive. Todd wrapped one arm around my neck in a sort of hugging motion. I could feel each of his hot breaths on the back of my neck and I think that there were a few kisses or nibbles back there also.

The longer that he was inside of me, the more that I could feel the heat of his cock. He continued with slow but forceful strokes. I was pretty confident that he was as deep as he could get from that angle as he was nudging me forward with each thrust of his cock.

The strain had eased up a bit and I was starting to enjoy it a bit more, but I was very quickly starting to get sore.

After several minutes of deep thrusting, I felt Todd’s grip around my neck tighten. There was one last quick flurry of thrusts before he completely ceased movement. Todd groaned, “Oh, god!” a couple of times and he actually sounded like he was being tortured back there.

I could feel every pulse of his cock as he came inside me, as well as the heat as he filled the condom with his hot cum.

He lay prone on top of me for what felt like forever. His body weight was making it difficult to breathe. He eventually started talking a bit and expressing how much he had enjoyed the experience.

I asked him to take his weight off of me but to leave his cock inside. It felt like it was still relatively hard. I raised up slightly, bracing myself up with my left hand while I grabbed my very hard and neglected cock with my right hand.

I asked Todd to thrust away gently. I started to stroke away aggressively as I felt his cock gently massaging my ass. It may have lasted a minute before the first spray of my cum rocketed over the edge of the bed and onto the floor. The following sprays all splashed onto my bedspread.

It was one of the most powerful orgasms that I had ever experienced. My vision got a bit sparkly for a second and I collapsed onto my cum-soaked bedspread.

I asked Todd to pull out and I started to turn over and climb off of the bed. Todd was still semi-erect, but his condom was sagging down at the tip. It was heavily weighted with a rather large load of milky white cum.

We both cleaned up slightly and I stripped the bedspread off of the bed. I headed downstairs to put it in the washing machine. Then I suggested that we should continue the fun and hop in the shower.

Todd asked, “Aren’t you worried about your folks coming home and catching us?”

I answered, “Oh, yeah. I forgot to tell you earlier. They won’t be back for at least another hour.”

So, we both headed into the shower. We were in there for quite a while. I would have loved to go another round with Todd’s cock, but I was way too sore for that. Instead, there was an exchange of oral as well as a fair bit of general exploration.

While things were never terribly romantic, there were a lot of body kisses and an occasional mouth-to-mouth kiss. We wrapped up the shower and put our clothes back on. They didn’t seem to stay on for very long as we kept trading favors for most of the night.

We did have everything back in place and the bedspread was washed and dried before my parents got home.

Although it took a good week for my ass to recover from that night, we became quite regular partners over the next few months. At times, I thought that Todd wanted me to fuck him in return, but he never asked me to do so. To be honest, I didn’t really want to fuck him, so I did not pursue the issue. I suspected that his understated nature would never allow him to ask me to do so anyway.

Todd moved away to go to college after that. Still, whenever he came back home for the next several years we would usually hook up somewhere.