Letters

Growing up I read letters to Playboy, Penthouse Forum and others. Not from the types of magazines I would buy, but from the magazines I had access to. Most of the stories were girls and guys, a surprisingly high number were about girls and girls, and very few were just about guys. The ones about guys I read over and over. Here are a few letters inspired by those old ones.

Letter 1 Cutting Lawns

A year before I could drive, I started cutting lawns. I dropped flyers in mailboxes twenty houses in each direction and soon I had a few clients. I charged from five to eight dollars plus two extra if I provided the lawnmower and gas. Most of my clients were older, a few were people who arranged for me to maintain their lawn when they were travelling.

I responded to one call and met a guy who was quite young. Maybe thirty. John wanted me to cut his lawn. He seemed reasonably in shape and capable of cutting his own lawn, but I wasn’t going to turn down business. I looked at his front and back lawn and quoted him the high end of eight dollars, in part because I thought he should be doing it himself. He wanted me to start right away even though his lawn could have waited a few days. I used his lawnmower, and he stayed outside to show me where to put the grass clippings and guide me on how he wanted the lawn cut. In the end I stepped into his kitchen, and he gave me a ten-dollar bill. I didn’t have change, and he told me to keep it.

He wanted me back often when the grass was growing quickly in the spring. Every time he sort-of watched me and he gave me ten dollars. When the school year was done, I switched my lawn cutting to daytime so I could have nights free to hang with my friends and have fun. I cut John’s lawn on Wednesday afternoons. When I was done with his lawn on that first Wednesday, he had a pitcher of lemonade ready in his kitchen and offered me a glass. He did that each week. It was great. The pitcher had cut lemons and lots of ice. I would stand there, and he would ask me questions. He was very attentive. I told him about my business, about school, my friends and mostly about what car I wanted. He didn’t talk much about himself. He lived alone and had an office but could set his own hours.

The first Wednesday of July was a scorcher. I ended up taking off my shirt and cutting his lawn in my gym shorts and a wide brim straw hat. When I came into the kitchen, I took a glass of lemonade and drank it down in one long drink. I closed my mouth and let the ice press against my lips and then I took a cube into my mouth. I stood there holding my shirt and hat. I don’t usually sweat because I was thin and stringy, but that day I was glistening. I put my glass down and he refilled it. He asked a few questions and I answered, but he seemed a little dazed. He asked me the same question twice. Then it got awkward. I finished my second glass as quickly as I could and headed off to the next client.

The following week was more of the same. It was hot and he even suggested that I take off my shirt. This time when I drank the lemonade, I made sure he didn’t refill it. He wasn’t as clumsy this time with his questions. He talked to me about sports. He suggested that I try basketball or wrestling. I didn’t bother with sports. For me it was just about hanging out with friends and making money.

The next week after I drank my lemonade, he told me he wanted to show me something. He had some magazines about wrestling and he thought I would be interested in them. I took off my shoes and followed him into the living room. He sat with his back against the couch and pulled out a box full of magazines. I sat beside him on the floor, and he handed me a magazine and took one for himself.

The magazine had articles about wrestling technique, summaries of tournaments and diagrams of wrestling moves. This was real wrestling, like college wrestling or high school, not the crazy stuff you saw on TV. There were sections of pictures that showed wrestling. The picture would capture the match at one moment and you saw the two guys grappling with each other in all kinds of positions. Some were pretty wild. I don’t think I could join the wrestling team if somebody would be pressing their crotch against me in front of a crowd. John put his magazine down and leaned over and pointed out various moves and positions. He explained how you would go from one position to the other. After each time he pointed at a picture his hand would go back down and land on my leg.

The wrestling outfits seemed tight. They revealed a lot. Muscular asses partly exposed and in a lot of the pictures you could see the outline of their penis through the tights. When I turned the page, I would scan each image and check out each shape that was revealed. He kept pointing things out and crowding me. His hand was landing higher up my leg. I turned the page and there was a full-page picture of two guys standing. One was behind the other, lifting his arms and pulling them back. The front wrestler's suit was so tight you could clearly see the shape of his dick. It was up to one side, and you could see a length of shaft then the edge of the tip. The balls were outlined, and the tightness separated them. The guy behind him was pressing up against his hip with a tent of his own. John pointed to the grip they guy was using and when his hand went back it was right on top of my dick.

I held the magazine afraid to move. My erection was pushing up my underwear and shorts and John would be sure to notice. I held the magazine in front of me so he couldn’t see. I was tensing up and I was afraid to even turn the page. Finally, something moved. My dick swelled up and moved against his hand. His hand moved a little. I thought he was moving it off, but he didn’t. It just shifted. Then I felt his fingers and I was sure he could feel the underside of my shaft. I was frozen. His fingers moved a little more every few seconds. I must have been holding my breath because all of a sudden, I gasped. Everything happened very quickly after that.

John shifted down and pulled off my shorts and underwear. He pushed my legs apart and got between them. His hand was on my shaft and then a second later his mouth was. I was frozen, but the feeling of his wet mouth and tongue lowering onto me made me shake and sink backwards against the couch. I watched as my whole dick disappeared into his mouth. I didn’t think it was possible and I felt like my dick head was in his throat. Then he pulled completely off, pushed my dick up and started licking my balls. He alternated between my balls and putting my dick deep into his mouth. When he clamped down with his lips and tongued my shaft I felt like I might shoot my load, but, whenever I came close, it was like he could sense it and he would slow down, or just tongue the tip. Soon however, my body was tensing, and an orgasm was imminent. I couldn’t slow down. I started rolling my hips as he was bobbing up and down and wildly flicking his tongue. My buttocks flexed and tensed, and I pushed up as he clamped down. My dick throbbed and my cum shot into his throat. I sputtered over and over until I was merely shaking and thinking I wanted him to let go.

He did. He moved back onto the floor facing me with his hand wrapped around his shaft and his pants and underwear pushed past his knees. He was long. Longer than anyone I had seen in a shower or bathroom, but I had seen few adults erect. He had a large head with a very defined ridge. His balls were very large. One rested on the wood panel floor and the other rested on top of the other. They were the size of local plums. He was thrashing his hand from the bottom to the top frantically. With his hand at the bottom of his shaft he stopped. His balls lifted. His dick shot out a string that landed along the floor. His fist pumped three more times as he fired criss-crossed on the floor. His last ejaculation was as much as I put out in a masturbation session. Then he slowly pulled his clamped hand up his shaft and more jizz dribbled out. That image was something I recalled many times in the years afterward.

The room was suddenly quiet. The spell was broken. I pulled up my shorts, put on my shoes and I got out of there.

Letter 2 A bike ride to the beach.

Kevin was a new kid at school. I was hanging out with him more and more. I liked to wrestle and horse around with my friends, but some of them got mad. Not Kevin. I would pin his arms back or trip up his legs and hold him down and he would just get me back. He had a smile on his face and afterwards he gave me a little grin.

A couple times when he came over to my house our wrestling turned a little grindy, if you know what I mean. Afterwards he gave me that grin. Nice.

In the summer he would bike over. One day he suggested we bike to ‘ghetto beach’. There was a lake in our town and a little beach. It wasn’t the greatest, but it was an Ok place to go for a swim on a hot day. So, after dinner we met up and biked there. We locked our bikes and changed into our trunks. There was a change room with a bench and a few shower heads. When Kevin changed, he stood, and he bent over to remove his pants and underwear and again to slip on his bathing suit and I got a good look at his ass. Nice.

The beach was not too crowded, there were only a handful of cars in the parking lot. We sat on our towels to check out the girls. None our age, but a couple of mothers filling out some two-piece bathing suits. Nice. Just to shock him I slapped his belly when he was not expecting it. A few minutes later he twisted my nipple.

The beach was not the best, mostly pebbles instead of sand, but if you went out far enough in the water it was sandy under your feet. We wandered out past the beach area along the cliff, and we started horsing around. Lifting each other, pinning each other’s arms, climbing on each other. How long can two boys horse around in the water? A long time.

By the time we wandered back, I noticed the last two towels on the beach were ours. I suddenly wanted to make sure our bikes were still locked up. I saw our bikes and only one car was left in the lot. It was a bit of a ride to get back, so I suggested we change and get going. As we approached the change building, a couple was getting into the last car and pulling away.

Once in the change room Kevin stripped and walked over to the shower head. He turned his head back towards me and told me I should wash off the lake water. Great idea. I walked over and stood under the shower head next to his. The soap dispensers were empty of course, but Kevin found a little cake of soap and started soaping his chest and armpits. I had seen plenty of boys naked in showers before, but it was easy to look at Kevin because he kept talking to me as he showered. He looked me up and down as well. Under the circumstances my dick was pretty hard. It had been hard for the last few hours. He handed me the soap and I cleaned myself off. When I put it down, he picked it up and stood behind me. He said he would ‘do’ my back. He scraped my back with the soap and rubbed with one hand, then both. He really took his time. Nice. This was even better than wrestling with him in the lake. His hands went all the way down past my waist and onto my buttocks. He spent some time there and washing the crack and all the way down beneath. Now I was so hard, it felt like my skin was stretching.

He stopped and started soaping himself. He was soaping the front of his legs, his knees and all the way down to his ankles. Oh my God. I was staring right at his asshole. I saw almost all the way into the pink area. Then he stood up and half turned and handed me the soap and told me to ‘do’ his back.

I stood behind him scraping his back with that little bar of soap. He adjusted his position and the head of my prick bumped into his hard smooth flesh. Now I was washing his back with both hands. I had to stand six inches back, if you know what I mean. But I came closer, and he backed up. Now as we moved the tip of my shaft slid over his crack even poking its way in. I stepped back and washed his ass as he had done mine. I made sure he got clean, all the way to the back of his balls. I pressed a finger all the way in and rubbed his pucker. His dick was sticking straight out. I moved my hands back onto his back and, as the soapy water ran down, I pushed myself into him. I could feel his wrinkly spot against the head of my penis. I pushed and he pushed back. I plopped the head in. He let out a gasp. I kept moving a little at a time. I was about halfway in when I reached around to feel his dick. It felt swollen and my fingers meet his.

I straightened out and continued to rock into him. It was getting greasier, and I was sliding farther in with ease. I put one hand on his hip and grabbed his elbow with the other. I started pushing in and out faster. It was going to happen. After a brief time, he gasped and moaned and felt him orgasming deep within his ass. I felt a pulsing and shaking. That put me over. I held his arm and hip tight as I thrust my dick in and out. A few more pumps and I was cumming hard. After pushing and grunting like five times I let myself slide out.

I grabbed the soap and cleaned myself off. I handed him the soap. He gave me that Kevin grin. Nice.

Letter 3 Reading on the porch.

On a summer day, my front porch was shaded and the most comfortable place to hang out. I had a soft wicker chair, and I was sitting there reading Penthouse Forum. The houses on my street were mostly surrounded by woods and I had a long driveway. No one could see me from the road because of the evergreen shrubs in front of the porch. I could only see into the woods and halfway up my driveway. I didn’t expect any surprises because I had a mailbox at the road, and I would hear a car coming up my driveway before they could see me.

That was important because when I read your magazine, I usually got a massive woody. I would try to read as many letters as I could before I would have to go inside and spread some magazines on my bed and take care of things. By my third letter I was straining in my shorts. This pair was a little tight, so I shifted my erection out of my underwear and shorts and had it sticking up one side. During the best part of the story, I would rub the head or run a finger along the bottom from my balls to the edge of my head.

I was getting to the best part of the third letter when I heard a little sound. A gasp. A breath. I looked over and there was a teenager standing on my deck at the top of the stairs not five feet from me. He had a baseball cap on, a t-shirt and shorts and a cloth bag was slung over his shoulder. He had a piece of paper in his hand. A flyer.

He was staring right at my crotch. I was going to try to get it back in my shorts, but what difference did that make now? I asked him ‘Is that flyer for me?’

“Aaa ha”

I held out my hand. “Well bring it to me.”

He came close and put the flyer in my hand without ever looking away from my erection. I just let like half a minute go by, but he never looked away. “Do you want to see all of it?”

“Aaaaha”

I unbuttoned my shorts and moved them over, so my balls fell out. Now I was sitting back with my seven inches pointing straight up. Another minute went by and still the kid was kind of frozen staring. I was going to ask him what color my eyes were, but I didn’t think he would get the joke. “Do you want to feel it?”

“ya”

He reached down and touched it with one hand and then both. He kind of brushed up against the skin and squeezed it a little. Then he lifted his hands with a giggle. Now he was back to just staring. I was thinking of putting it away and telling him to leave, but I was too horny. I asked him if I could see his. When he didn’t react, I had to repeat myself.

He looked down at his own shorts. He was tented. He pushed his shorts and underwear down in one motion and stood there again looking at mine. So, we were back to staring. I asked him if I could touch it.

“Yeees”

I sat up and reached over and gently touched his hardon with my fingertips. I moved my fingers along his head, his edge, down his shaft I felt his balls. He made a squeaking noise and a drip formed at his tip. I smeared it around. Then I put my palm along the bottom of his shaft, wrapped my fingers around it and slid my hand forward and back. Finally, the kid was looking down at his instead of mine. After just a few pulls and pushes he looked skyward and squirted some cum onto my wrist and my forearm. He shook and bent and something more solid came out to pour onto the porch. I cleaned up my arm as the kid stood there staring down at the pool he had made on my porch.

Well, he had seen me and now I had seen him. I straightened my shorts and went into the house to wash my hands. When I came back to the door he was still there. “Well, I am going in now.” I told him.

He didn’t respond, but he wasn’t walking away either. Then he surprised the hell out of me by asking “Are you going to jerk it?”

“Maybe.”

“Can I watch?”

I opened the door wider, and he came in. I walked into my bedroom. Next to the bed was my lotion. On the bed was a playboy and a towel. I had a routine. He followed me into the room. “Not a word to anyone ever.” I said. He nodded

I unbuttoned and removed my shirt. I lowered my shorts and underwear. I crawled onto the bed and lay back. I positioned the towel next to me and was going to grab the playboy but then I noticed him staring at me. He had moved to one side of the bed as close as he could be.

“Do you want to get it hard?” I asked him. He nodded.

“Put your fingers on it.” “Rub the tip.” “Gently.” “Slowly.” “Now put your hand around it and slide slowly up and down the shaft.” “Not so tight.” “Keep it up.” “Now feel my balls.” “Gentle.” “Yes. Like that.” “Now with your other hand rub the head.”

He got on the bed and knelt beside me when he started using two hands.

“Smear that wetness around.” “Ok gently up and down the shaft for a while.” “Mmmm.” “Ok Stop.” “Get the cream.” “Put some on your palm.” “Now gently again along the shaft.” “Yes.” “Good.” “Oh ya.” “That’s good.”

His other hand was back on my balls. I didn’t have to tell him.

“Aahhhh.” “Not put some cream right along the top of my shaft.” “Yes.” “Now work it in.” “Keep it up.”

He was leaning over me staring straight down at my crotch. His eyes were wide. When I stopped giving him directions the only noise was my breathing and the sound of the creamy stroking. He obviously had some experience. I watched him slide one hand up and down my shaft from by balls the edge of the top. He kept his other hand on my balls, occasionally moving his palm against them. I was started to tense. I watched his hand. I listened to the slap of skin. I felt the cream pool on the edge of my balls.

“Use both hands on the shaft.” “Just like that.” "That's good." “Yeees.” “Keep it up.” “Don’t Stop.” “Don’t.” “Stoppp.” “Doeeeown.”

My hips shook and my dick flexed against his hands. Goobers of cum shot out as my body was wracked by convulsions. I squirmed one way then another, but he held me in place with his two hands on my shaft. When the last spasm left me, I pushed his hands away.

I grabbed the towel and wiped off my jizz from his forearms and neck. Then I pressed the towel into a pool of cum on my stomach. I told him to wash off.

A minute later he was putting on his shoes and leaving. When I went and got the flyer, I realized it was the same flyer that came every week. I guess I would find out in seven days if he was going to put it in the mailbox by the road or bring it to my door.