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Surprising Kid

Surprising Kid, Sexual Memoir

This boy was a great kid. Raised well. Quiet and polite. Good-looking too. You don’t have to be gay to admire the look of tall, skinny, blond boys of Nordic descent who wear their hair long.

I’ve known his mother for quite a while. In fact, we dated back before he was born.

Now, having just graduated from high school, he didn’t know what he wanted to do. She was secretly relieved he didn’t want to go to college, because after his father left, they were in poverty and she could never help pay for his education. She hatched a plan, which turned out quite well, and all she had to do was one thing. She suggested he ride with me for a week.

I wasn’t at all interested in having a kid tag along, but I did it because it seemed important to her.

Monday morning, I pulled up in front of their shabby little garden apartment and he met me promptly in front with an eager greeting. If he was reluctant to participate in his mother’s experiment, he didn’t show it to me.

It was a half-hour drive to the first appointment. Trying not to offend him, I let him know in no uncertain terms that he was to be as invisible as possible. I figured the last thing my clients would want is to deal with an 18-year-old kid. Other than that, it was mostly small talk on the ride.

We got there and he helped me drag the air conditioner out of the truck, and unboxed it while I set up the lift and removed the old air conditioner from the motorhome. I appreciated the help. Maybe dragging him along wasn’t going to be so bad after all.

I had asked him to be unnoticeable, but what was the first thing he did? He started a conversation with the motorhome owner. The client seemed to like the kid. It kept the client out of my hair while I finished the installation, and so that, too, turned out alright.

We went to the other appointments of the day – trailer brakes, a generator that wouldn’t start, and sealing a roof. Driving between jobs, the kid told me he admired my truck. It is something I’m proud of, and so it was nice to hear him speak about how much he thought it was cool. He went on to call it a ‘Swiss army knife’ of vehicles. It’s true. Although the truck is big, and sometimes annoying to take into narrow driveways or to park in tight places, it carries a lift, welding equipment, and every tool you could possibly need in the RV repair business.

The week wore on. Having the kid around turned out to be good. He was helpful. He would just do grunt work, such as spreading cat litter on an oil leak and sweeping it up, without even being asked. He was intelligent too. For instance, I’d be on a roof, and without me requesting it, he’d climb up the ladder with a 7/16″ wrench, handing it to me right when I needed it.

I have to admit too, I had been kind of lonely rolling around in that old truck by myself. I enjoyed the chatter between jobs.

Until one day, he stopped me dead in my tracks by asking whether I ever masturbate.

We were at a traffic light at the moment he asked. I think I turned red in the face, and was concerned that the people stopped next to us saw me, maybe even heard him ask the question. Geez! How does one answer that?

I must have formed three or four answers in my head before I finally said, “Well, sure, doesn’t everyone?”

Slowly, he wedged masturbation into several conversations during the next week or so. I gradually opened up becoming more used to these conversations, even enjoying them. Secretly, I had jerked off the past several evenings, remember our conversations. He had admitted having phimosis, and seemed to want to know how ‘ordinary’ people jerk off.

I acted like I knew what that was, but didn’t have a clue. I tried to look it up on the internet that evening, but couldn’t remember the word. I tried “flamotis” and all sorts of things, and so didn’t find an answer. I was very, very curious. What could possibly be wrong with the kid’s penis? Or was it something affecting his semen production? Something about his balls maybe?

The next day we had a case where the client wasn’t around. I was replacing the CV joints in a classic old GMC motorhome. I admitted to the kid that I didn’t know what phimosis was.

He said, “Here, look.” With that, he stood up, unbuckled his belt and lowered his pants and underwear. He grabbed his penis pulling it forward and showed me.

My heart leapt into my throat. I would not have expected that reaction. I was suddenly feeling very horny, and from a kid, an 18-year-old boy! Who knew that I had any homosexuality in me at all? Oh, sure, I goofed around with the kids in my neighborhood when growing up once or twice. I remember giving and getting a couple of blowjobs. They were alright. I kind of enjoyed the experiences, if also feeling guilty about them. Mostly, I played with the girls as I was growing up. I knew much more about pussy than dick and by the time I met the girl who became my wife, I was already experienced in the ways to please her. I still miss her. To this day, I’m afraid of small cars.

But I’m getting off topic. There he was showing me his penis. He acted as ordinary as if he was showing me a pocket knife. My heart was unaccountably racing. I didn’t understand what he was trying to show me. I saw a nicely formed uncircumcised penis, with the foreskin totally covering the tip, and coming to a point.

I had seen uncircumcised penises before. Who hasn’t seen some online porn involving an uncircumcised guy? He must have seen my confused look so he came right out and told me: “The foreskin doesn’t pull back.” He demonstrated by pulling his foreskin somewhat. I was starting to understand. So that’s phimosis. The foreskin covers the tip of the dick and can’t be retracted.

His pants were back up in an instant. I didn’t know how to react. I didn’t know what to say. I turned back to the brake rotor which I was putting back in place.

That evening had me jerking off big-time in response to that little scene earlier in the day.

Nothing more was said for the next couple of days about phimosis, although the kid did bring up masturbation a couple more times. So did I. It was mostly him asking silly questions, like “Do you think it’s OK to jerk off more than once per day?”

I would respond, telling him things like ‘In my day, we weren’t very open about sexual matters. I discovered masturbating on my own. I wish times then were like times now. We were all isolated and afraid.”

By now, the kid was on my payroll. He had become officially my apprentice. To my delight, he was loving the work, and never complained even when there was something repetitive or difficult to be done.

He started asking to see my penis. First it was very shrouded, like, “I wish I knew what a normal penis was like.” or “I’ve seen circumcised men online, of course, but have never seen a circumcised dick in person.”

Within a week, it became blatant. “Hey, when are you going to let me see your cock?”

I kept refusing. It just wasn’t right. Was it? I mean, here I was more than three times his age, and I was having strong sexual feelings about him. In a way, I was starting to feel that having invited him to ride with me was a mistake. This sexuality was making me very uncomfortable. At night, I was jerking off resulting in crashing orgasms, with memories of looking so briefly at the kid’s dick in my mind. I was fantasizing about sexual activities with him.

One morning, I asked why he didn’t just get circumcised. He said he had read about adult circumcision. It requires a painful recovery. I offered to give him time off so he could get that done. He winced, saying that he would never, ever let anyone cut on his dick.

I asked whether he’d rather go through life with phimosis. He replied that he’d rather die than get surgery. It’s true, in other conversations, I had discovered that he’s deathly afraid of the medical system. He hadn’t had a physical exam since before he could remember. His fear of doctors was like my fear of small cars.

He said that he didn’t have to go through life with phimosis. He had read about exercises that would eventually stretch his foreskin as long as he was patient.

I was like, “Ok, so do the exercises.”

He replied that he couldn’t.

Now I was confused. “Why not?”

“I’ve tried a few times, but I just won’t pull on the foreskin enough to do the job. I kind of hurts a little bit, so I stop. I need someone to do it for me.”

I’ll bet you know there this conversation is going. He asked me to do it. I refused, knowing secretly that I’d like nothing better than to get my hands on his penis. Over the next few days, he kept bringing it up. Finally, he was practically begging me to do it. I kept pretending that I didn’t want to, because I knew that… Well, what did I know? Was there something wrong with helping a kid in need? Was it gay? Af it it was gay, what was so wrong with that? Would my wife look down on me from heaven with shock, horror? No, I knew her. She’d be amused. Actually, if she were alive today, she’d probably talk me into it. She’d want to watch. Or participate. That’s the kind of girl she was. Very bold and forward and I loved her for it.

He wore me down. One Thursday driving from the first to the second job of the day, we arranged that I’d take him home to my place and do his exercises for him. I was so nervous and jittery the rest of the day I could hardly work. I actually dropped a screw into the panel behind a refrigerator and had to spend time fishing it back out. The kid seemed kind of nervous too. What a long afternoon it was!

Finally, finally, we were in my place. I offered him a beer. He refused, saying he wasn’t going to follow in his deadbeat father’s footsteps. He didn’t even want one sip of anything alcoholic. Good for him! I handed him an orange juice, and got myself a beer. I couldn’t drink it. My throat was tight. My hands were shaking a bit. Weird, eh?

“Well, how are we going to do this?” I asked.

“Um, let’s go in your bedroom.”

We went in. He started pulling off his shirt.

“You don’t have to take off everything. You can just pull your pants down,” I offered. As soon as I said it, I figuratively kicked myself. Of course I’d like to see the kid all naked.

He said, “No, it’s probably better to do this one hundred percent,” and continued removing his shirt. Then his shoes and socks, then his belt, his pants, and finally his underwear.

He was erect! The minute his pants were off, his penis bobbed right up at a 45-degree angle. There wasn’t any hair there. The kid was evidently into manscaping. The skin was quite white, especially his small, tight scrotum. His erection was smaller than I would have expected. Not much wider than my thumb.

My heart was racing! I was visibly shaking. I could hardly stand up.

“C’mon, you too!” I was surprised, and delighted. I was always body dysmorphic, thinking I’m not very good looking. But, he wanted me naked. I pretended to balk, but he insisted, and soon, my clothes were entirely off also. I was erect. I too, had been manscaping my genital region. Somehow, I was slightly embarrassed for him to know that.

The boy looked at me, and quietly said, “Beautiful.”

Who knew? Later, I came to realize that this boy was not only mostly homosexual, but totally into older guys. And not just any older guy. He loved me. Right from the first day!

As our relationship grew, I knew there was something I had to do. I was dreading the day. I had to let his mother know what was going on. It’s not like I was a pedophile or anything. The kid was old enough. But still, it was highly unconventional. And old guy and a young kid. And both male, for heaven’s sake!

I invited her to lunch. I sheepishly started trying to bring up the subject of me and her son. Just as I was taking my first crack at opening that conversation, she said, “I know about you and Tony.”

Hearing her say that scared the crap out of me. She said it calmly, but what was going to happen next?

“And I approve,” she quickly added, evidently seeing my agitation.

She went on to explain that this had been part of her master plan, that it went farther than she expected, yet she was delighted.

She knew her son needed a trade. She knew I was in a lucrative business. She figured her son was mechanically inclined. She went on to say that she also suspected, more.

She knew that I had been without what she called ‘company’ for several years. She knew that her son was gay. She knew he seemed attracted to older men. She thought, maybe, if everything worked out just right…

So now, Tony lives with me in my house. We continue to ride together to all our clients. He has continued to grow into the RV repair business, knowing almost as much about the repairs and installations as I do. Oddly, we seldom argue. I think it may be because of the vastly different perspectives, him being so young, and me so old. Then too, his mother raised him well.

As to his mother, she and I have recently been kind of half-dating. She’s almost as bold, outgoing and adventurous as my wife was. She and I haven’t had sex, but we have masturbated each other. What a joy!

Now, I’m not one to do things behind anyone’s back. Before I did anything with his mom, I asked Tony whether it would be OK. Not only was it alright, he was very supportive of the idea. To my shock, he suggested all three of us could have a masturbation session together some day.

When I told her about his idea, she smiled big, and said she’d love that. Fact is, so would I. I’m sure it will happen soon.

So what about the kid’s phimosis? From that first day, we worked on that. He laid down on my bed. I pulled up my rolling chair next to the bed while my heart continued to race. My knees were so weak I had to sit down. I gingerly put my thumbs and fingertips on his foreskin and pulled down slightly.


I wouldn’t have expected it would be that sensitive. Phimosis is a real and bothersome condition. He encouraged me to pull down a little bit again, even though it was mildly painful for him.

He was still totally erect, so I guessed it wasn’t too painful. I, sitting in the chair, was totally erect also. I didn’t do anything about it. After all, this was about Tony, not me. But he was staring at my dick like it was the only thing in the world.

I worked the next several minutes, balancing pulling down on his foreskin to the point where it hurt him, but not too much. Suddenly, he ejaculated, writhing all over my bed.

I was so delighted that I ejaculated a moment later without even being touched. I must say, it was the first hands-free ejaculation of my life (but not the last.) It was a very strong orgasm.

Days turned into weeks. We faithfully did his exercises every morning and evening. For the longest time, the exercises ended with him ejaculating prematurely. He’d then turn his attention to me, jerking me off to a crashing orgasm. Sometimes, after doing me, I come back to him, jerking him off in an ordinary way so he could cum again. He was often good for twice in a row. Sometimes I could do that too, but generally, once was enough for me.

We experimented with other sexual techniques. We kind of liked giving each other blowjobs, but we mutually agreed they didn’t measure up to our lovely – and loving – handjobs.

Our experiments with anal intercourse turned out to be non-experiments. I really like the look of his puckered pink asshole, but it’s small. Maybe because he’s tall and skinny, but there’s no way a guy could get a cock in there. Well, maybe that’s an exaggeration. I’ll bet he could be buttfucked, but he’s not into it, and neither am I. We both very much enjoy me putting a finger in his anus. He’ll finger me too.

For the longest time, there was no way he could buttfuck me, not that I would have wanted that. I’m just a mutual masturbation guy, through and through. The phimosis would have prevented anal intercourse. I don’t know what would have happened if he tried putting it in someone’s vagina, but we never found out. In time, the phimosis did reduce. He can now pop his foreskin back behind his fully erect glans, but then it still takes a minute to get it to pop back into place. It no longer gives him any pain at all, but we’re still doing the exercises. Might as well do it one hundred percent. Doing things ‘one hundred percent’ is one of Tony’s favorite expressions.

As to his mother joining us, all three of us are excited by the idea. However, we haven’t quite made the move to make it happen yet. Maybe we’re afraid of the dynamics it could set off. Personally, I believe we all have great personalities, and our relationships will only improve. I’m sure it will happen soon.

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