First Time 177

In 1962, I lived in Arlington Heights, Illinois. I had celebrated my 18th birthday and was looking forward to graduating from high school.

College would be my escape from an environment where sex was mainly whatever my right hand could do for me, encouraged by my parents' sex books and an occasional girlie mag from the Park Ridge Pharmacy. Girls would let you fondle their breasts through their blouses but that was it. Masturbating was my sex life.

I lived down the street from a man in his early 40's who was a traveling salesman. "Charlie" was a single guy and gone a lot, sometimes for a week or two. I shoveled his snow in the winter and cut his grass in the summer.

I also brought in his mail. He paid well and trusted me with his house key.

One day I was nosing around in his garage and found some nudist magazines, MALE nudist mags. I had never seen those before. Naked men playing baseball, doing gymnastics and sun bathing. These guys had BIG cocks. I got hard almost immediately. Why, I wondered?

I had never thought about sex with a man before. I remembered that I also got hard reading about the description of the grounds keeper's penis in "Lady Chatterley's Lover". That should have been a clue that I was attracted to men in a sexual way.

As I turned the pages, I started rubbing my cock and thinking about the guys in the magazine. I decided to masturbate while sitting on the riding lawn mower. I dropped my pants, leaned back, put my feet on the steering wheel and went to work. Spit was the only lube I had but that worked pretty well. What an orgasm! All over the mower!

I went back over to Charlie's house every day after school. I imagined I was naked with the guys in the magazines and we were jacking off all over each other. More sperm gone astray.

I searched around for more magazines and found a stack of old Playboy's. More Jacking but with the big titted girls displayed in living color. Wow! When I came while looking at these girls I realized that naked men and women turned me on. (That would be a big advantage when I got older.)

After a few days of intense pleasure I decided to move into Charlie's family room. His couch was more comfortable than the lawn mower. For the next several days I pounded out climax after climax.

One afternoon, without any warning Charlie found me, pants around my ankles, cum on chest and dozing, enjoying the afterwards. He just stood there with a grin on his face, no clothes on his body and the biggest erection I had ever seen. I guess he had come in while I was going to it, watched a little and then decided to join me.

He sat down next to me on the couch and proceeded to beat off, cumming all over his chest. He didn't say a word until he came, and then only "Watch this!"

What a pair we were! Two naked guys, one much older, staring at the cum on each other's chests. Eventually I recovered and told him I had to go home for dinner. He said "Come over any time." And that is what I did.

After my initial experience with Charlie, I couldn't wait to see him again. The next day after school I went over but he was gone. On the road again I guessed. I went inside, took off my clothes and got into his bed. I masturbated furiously and came all over his sheets. I was secretly hoping he would "catch" me again but he was really gone. I got dressed and went home.

Every day after school it was the same. I made his bed after each time I came on his sheets. Several days of cum gave it a nice aroma. The next Sunday on the way home from church, I saw Charlie's car in his driveway. Hooray! I told the folks I had to go over and get paid and maybe get a tip(the tip of his penis is what I was actually hoping for).

I knocked on his door and he answered, wearing a bathrobe. After I stepped in, he closed the door and let the robe fall open to show me he was naked underneath. "I was hoping you'd come over. Follow me," he said.

I did as I was told and he led me into his master bath. Charlie dropped his robe and said,

"I was just getting ready to take a shower. Care to join me?"

I immediately took off my clothes as he sat on the toilet and watched me. He smiled when I started getting hard. He reached out and gently took my penis in his right hand and pulled me to him. When I was close, he jacked me slowly while he ran his tongue over the tip of my cock. I was really hard now and he said, "Time to wash up." He led me into the shower holding my erection.

This was a BIG shower. Two heads on the ends covering at least seven feet with brown unfinished tile, like in a locker room. It had a seat in the middle against the wall. I could only imagine what that was for.

We faced each other, hot water beating our bottoms and washed. He soaped himself all over and then handed the bar to me. With trembling hands I lathered up. When we were both hard and soapy he turned me to face the wall of the shower and told me to bend forward. As I did Charlie began scrubbing the area around my anus.

I had never done more than run the soap through there but he massaged my opening as he washed it. When my bottom was clean Charlie began to soap my hard penis. The last straw was his soapy finger in my bottom. He pushed it in and out a couple of times and I came me all over his tile wall. He caught me as I slumped back against him. I felt his cock against my back and wondered, what next?

We stood in the shower for a couple of minutes, letting the hot water beat on us.I was drained but Charlie kept his finger in my bottom. Finally he said, "Let's get dried off" as he removed that wonderful finger and helped me out of the shower.

He used a fluffy towel to dry me off but when he turned me around and dried my bottom he got dropped to his knees and spread my cheeks. He ran his tongue up and down on my anus. He really liked my ass. I was still soft but I knew he was hard. Licking my bottom got him harder. After I was really slippery back there, Charlie stood up, took my hand and said "To bed."

We climbed into his king sized bed and pulled the sheets over us. Snuggling with him was great. In a minute or so he rolled me over to face away from him and snuggled into my bottom. His cock filled my crack. I was imagining if it would fit in me. I knew nothing about fucking. I understood the anatomy. I just didn't know exactly how it happened. I soon found out.

Charlie pulled a small jar of Vaseline from under his pillow, got a finger full and began to apply it to my anus. I liked the feeling even though I wasn't sure what was going to happen next. "Have you ever put anything like a penis in your bottom?" Charlie asked as he re-inserted that wonderful finger. In truth I had been using my mother's enema nozzle in my bottom as I jacked off, experimenting and enjoying the way it felt.

I told Charlie and he laughed saying, "Well, my injection won't be as filling but it will make your ass feel good." With that he touched the head of his cock to my anus and began to push. I was OK at first but as he went in further I froze. It really hurt. I squirmed and finally said "Stop!" To my surprise he did.

I was embarrassed that I had stopped him but Charlie didn't say a word. He got out of bed and went into the bathroom. When he came back he had a long thin black thing made of plastic with one end that looked like a penis. Charlie explained, "this is called a dildo and it will help you open up." He slid in behind me began probing. He soon found the target and slowly pushed it in. I don't know how much went in but it felt good. He finally stopped and said, "Let your ass get used to the size".

For a few minutes we lay there. He kissed my neck and held me. Finally I told him I thought we could try again. He slowly pulled the dildo out and then handed me a pillow with instructions to put it under my hips and lay down on it.

As I was settling down on the pillow I felt Charlie straddle my bottom, spread my cheeks and lay his cock in my crack. As the tip of his penis pushed on my anus I thought here we go and in it went.

I had never been fucked so the sensation of Charlie penetrating me was both painful and exciting. I had wanted it, I had fantasized about it and now I was getting it. He pushed the head in and stopped. I was squirming and sweating.

I did not know my anus could open that wide. but in a minute or so he went all the way in. I could feel his groin pushing against my

bottom. Charlie covered me, laying on my back with his cock buried in my bottom. In a soft voice Charlie asked, "Are you OK?" and "How does it feel?"

I replied, "OK, do it," and he did.

Charlie slowly pulled almost all the way out and then paused. Without warning he slapped my bottom, hard, and said, "You are a bad boy. You jacked off in my bed and you shot cum on my shower wall. I am going to punish you." With that he slammed his cock home. Hard. I saw stars. Then he pulled back out but immediately went in again. No hesitation, no let up, no slowing down. Pound, pound, pound. He slapped my ass with every stroke.

I could feel my ass cheeks getting hot and my anus ring was on fire but at the same time, I was getting hard. The more he plowed me and the more he spanked me, the harder I got. Soon he was in a rhythm and I was swept along with him.

He wrapped his arms around my shoulders. I wanted more. I could feel his penis start to swell and then he came, yelling, "FUCK,you are so tight!" and he shot load after load into me.

Charlie collapsed on my back and his cum ran out of my bottom into my crotch. I was really sore but I wanted him to stay in me. What a ride!