We met again a few days later. This time I brought a towel to place under us so that the cold grass didn’t press up against us as we fooled around on the hill. Each time we met we moved over to the hill except for one time, the grass was wet from a recent rain, so we moved into the woods and stood against a tree.
Like so many times before we sucked each other from a kneeling position. Massimo seemed to like this more than I as he grabbed my hair and gyrated into me.
As fall went on, I learned to pay attention to the weather. We couldn’t meet up if it rained. One time Massimo failed to show up. He told me his parents were talking to him and he couldn’t get away. We agreed to wait fifteen minutes then give up when that happened.
One day at school we found ourselves isolated and able to talk freely during lunch break. We started talking about what we were doing. He told me that he noticed that I rubbed my tongue against his shaft each time and I told him about the first time in the park when I felt him squirt against my tongue. I asked him if he felt me when I came.
“Oh God yesss.” He said in a high-pitched voice. “The first time overwhelmed me. I couldn’t believe it. I couldn’t swallow it all. Every time there is a lot.”
I asked him about when we did it the other way, if he felt it.
“Not the first time in your basement, I was too distracted. But when you came inside me on my bed you held still for a moment, then I felt it. I felt your dick kinda expand and then a warm wetness.”
I was staring at him, imagining being with him again on his bed. He could tell what I was thinking as well because he practically blushed.
We met a day later, on the bench in the park. After he sat down, I put my hand on his leg. He pulled something out of his pocket. It was the tube of lube that I had last saw in his bedroom. I went into automatic mode. I took the tube and then his hand and led him into the woods to the tree we had leaned up against before. My hands were on him front and back under his shirt. I turned him one way then the other groping him. He could barely react, and he grabbed onto the tree for balance. I pushed down his pants and my hands were on him front and back. I held his dick with my left hand as my right roamed around. I felt his nipples and made them hard. I put my finger in his crack and rotated the tip dip inside of him.
We were facing each other with my hands on him front and back as I breathed into his neck. He moved his head and kissed me. I turned him away and squeezed the lube onto my fingers. I pressed the lube against his balloon knot and in and put some on my head and shaft. I lined up my turgid hardon against his hole and shoved it in. I felt so thick, and his opening clenched so tight. I started rolling my hips, sliding into him. It was like my hips were in charge and they just did what they wanted. He leaned forward holding onto the branch. For the next few minutes, I rolled my hip as my shaft went farther and farther in until the whole length was plunging in as much as it could. I never stopped moving and the sound of our breath combined with my hips slapping his fleshy butt. Eventually I leaned backwards and pushed into him and held. I grunted and thrusted. He whined, I grunted. Three times I grunted and came. Then my body went soft and leaned forward resting my face on his back.
Then he moved and I fell out of him. He adjusted his underwear and pants and got himself straightened out. We were standing face to face, and I was still breathing hard. He pressed his lips against mine. I stood there and let him kiss me and slide his tongue into my mouth. Then he left me and said ‘goodnight’.
I stood in the dark woods listening to his footsteps in the distance until all I could hear was my own breathing.
At school he occasionally looked my way and gave me a great smile. When I got close, he would whisper ‘not tonight.’
Finally, he gave me time to meet him. I had the tube of lube now, so it was my decision to bring it that night. At the bench I offered to go to the hill. Then I showed him the tube and asked him if he preferred the woods. He got up and walked into the woods. I could tell that he wanted to kiss, so I let him. I closed my eyes. I had kissed a few girls before and it felt the same. I used the opportunity to get my hands under his shirt and feel his wonderful skin. I wasn’t sure last time if he came or if he waited to go home to masturbate, but I wanted to satisfy him. Soon I was on my knees tugging down his pants. This time both my hands and mouth were on him. I actually kissed his ass at one point. Soon his stiff little prick was in my mouth, and I was giving it my all: suction, tight lips and flicking tongue. He moaned and I could tell he was on edge, but then he pulled his hips back and pushed me away. Then he guided me to stand up. He turned away and grabbed onto the tree branch and leaned over.
The tube made a small noise as I squeezed a dab onto my shaft and fingers. I greased his hole and soon had my head pressed up against his opening. This time I kept up a gently thrusting. When I was about three quarters in, he said ‘Right there. No farther.”
So, I slid it in him. In the darkness I almost saw my shaft sliding between his cheeks. ‘Yes’ he said a couple of times ‘Right there’.
I kept up my shallow thrusts. One of his shoulders lowered. He was holding onto the branch with one hand as the other was between his legs. We kept up a constant pace for what seemed like minutes. Then he gasped and I felt him cumming. I exploded in him. A couple short thrusts later my dick popped out and the last of my squirts landed on his back.
I reached down for my underwear to clean off his back and ass. He thanked me and straightened out. Again, I let him kiss me. I pressed my tongue against his. Then he stopped and walked away.
The next time I got to the park a few minutes early and waited on the bench. The minutes ticked by slowly and I knew he was late. I didn’t have a watch, so I tried to measure how much time had gone by. I wanted to see him, so I waited patiently. I heard footsteps. They were coming from the opposite direction than I was expecting. A man was walking down the path towards me. I tried not to notice him, but he stopped in front of me and then sat on the bench.
The whole park was empty, and this guy decided to sit on the same bench as me. I looked sideways at him. He was maybe 30, dressed in an expensive-looking jacket, with a nice hat and a scarf hanging down. Even his shoes looked expensive. A minute went by, and I was beginning to get seriously weirded out. I wanted to wait five more minutes, but he wasn’t moving on. Then he made a sound, as if he was trying to talk and failed.
Then he started again. “Waiting for someone?”
“Yes.” Why did I answer him?
“Is he late?”
Was he late? What was he talking about? Did he know? I didn’t answer and we sat silently for a while.
“Uhmmm”. He cleared his throat a bit and then croaked out. “I could take his place.”
I stood up and stepped away from him a couple of steps looking back.
He looked straight at me. A serious look on his face. “On the grass or in the woods. I would do either. Whatever you want.”
Holy smokes. The guy knew about us. I turned and walked quickly away towards the entrance that Massimo would have taken. I waited there for a few minutes making sure that Massimo didn’t show up and that the guy didn’t follow me. I eventually walked ahead and went down a side street to go home while avoiding walking through the park again.
I was a little freaked out when I got home. We couldn’t go to the park again, and I would have to tell Massimo.
At school Massimo apologized for not showing up the night before. I led him to a spot where we could talk, and I told him what happened the night before.
Massimo really freaked out. “He knows. He watched us. What if he knows my parents? What if someone else knows? He probably lives in my neighborhood. He knows who I am. He could tell people about me. We can’t do this again.”
“I agree. We can’t go to the park again.”
“No. Not just the park. We can’t do it again. Anywhere. I have to stop talking to you at school. Someone could know.”
I told him that he was being paranoid. But he said he couldn’t take the risk and walked away.
I never saw him alone after that day. We barely talked again.
The weeks went by, and I realized that it was over. I still looked at the magazines and I was still attracted to most chicks that I saw there, and I was attracted to a few at school. I had access to a car finally and I convinced a girl to go out with me. Shirly was cute, a little bigger than the more popular girls but with great skin. I had seen her in a bathing suit in the summer and I was impressed. She had sizable breasts and a nice round ass. Even rounder than Massimo’s.
On the first two dates we only held hands and kissed at the end of the night. The third time, when we kissed, I slipped my hand under her shirt and felt the soft skin of her back. I got my other hand in her shirt and felt her stomach. I loved the feel of it, although most boys would have called her fat or worse. I wanted to plunge a hand down her pants to feel her ass, or to check out how much hair she had above her pussy, but I knew that was too much.
She continued to kiss me and shook a little bit as I touched her, so I decided I would cup one of her breasts. As I raised up my hand and touched the bottom of her bra, she clamped down on it with her hand. She twisted away and stood back. She tersely said “Goodnight.”
The next day she broke up with me. She said I was ‘too handsy.’
She had no idea.