The next Friday I again ask Coach H if the two of us could masturbate after baseball practice. Coach H invited into his office as usual. I undressed first and sat on the sofa and started to play with myself. Coach H stopped me and handed me an ice pack. “Put this on your groin and think of something non-sexual like physics. I want your dick limp” he tells me. I comply. After a few minutes my cock is cold and limp. It has shrunk to its non-aroused state. While I am holding the ice pack over my cock Coach H undresses and sits next to me. When he is sure my cock is fully limp Coach H lea... Continue»
To catch the readers up: I am an 18 year old in high school ( I got held back ). My baseball coach, Coach H, caught me masturbating in the locker room after a Friday evening practice. Coach H is 58, hairy, and athletic. He tells me masturbation is natural and does it as well. We went to his office and masturbated a bit before he fucked me in the ass. Since that evening Coach H and I have gotten together in his office Friday evenings after baseball practice and masturbated and he fucking me in the ass. When the baseball season ended Coach H invited me to come over to his place on Saturday evenings to continue our fun.
It took several weeks before I could rearrange my schedule so I could meet with Coach H on a Saturday evening at his place. All I could think about during that time was the how it feels to have the coach’s hard cock thrusting in and out of my ass. I would masturbate to the memory of our previous encounters. I arrived at Coach H’s house around 6:30. I was a little bit nervous. Coach H sensed this and gave me a bottle of beer to drink while we sat around his living room talking about how school was going and how much we both loved baseball. When I was relaxed enough Coach H got up and led to me his bedroom. We undress and sit at the head of the bed. Neither of us was erect. Coach H asked if I would like to watch some porn to get more into the mood. Without waiting for me to reply Coach H reached for the remote and turned on the TV across the room. A video started to play. It was Coach H having sex with some woman. “That’s my ex-wife.” he said. “I have hundreds of videos of the two of us having sex”. On the video Coach H was kneeling behind his wife and making long deep thrusts. The thrusts were long enough that you could see his cock as it slides in and out. It was very erotic and certainly got me in the mood. My cock was a full attention. Both Coach H and I started to stroke our own cocks. We soon stroked each other’s. All the time watching the video. After 5 minutes Coach H slid down and started to suck on my cock. Watching the video of Coach H fucking his wife and having the Coach suck on my cock was too much for me and I quickly reach orgasm. Coach H swallowed my load. But instead of stopping he continued to suck on my cock especially around the head. I started to feel pain from the sensory overload from the sensitivity of my cock. I tried telling him to stop but Coach H kept sucking my overly sensitive cock. I started to pull away and Coach H held me down with one arm across my belly and continued to suck my sensitive cock. I tried to wiggle out but Coach H shifted his position so his hairy chest was on top of my belly. As he was shifting his position he momentarily stopped sucking my cock and said "Trust me. You will eventually like this". I was flailing around. If Coach H had not laid his chest on my belly I would have been up off the bed. But he was right. While painful it was also pleasurable. The pain became more and more pleasurable as Coach H continued to suck on my cock. I felt another orgasm start. I groaned out "I'm cuming" and let my mind and body go. It was the most intense orgasm I have had in my life. By ignoring my pleas to stop when my cock was super sensitive Coach H brought me to a super orgasm. Coach H rolled over, looked up at my face, and said "See I told you that you would like it". Coach H shifted his position down so he was lying on my legs. He teased my cock which it was still sensitive.
Coach H started to talk. You know the first time I had someone do that to me was when I was younger than you. An older neighbor Mr. M. (must have been in his 40's) took me on a fishing campout at a lake. After we fished some we went skinny dipping. We horsed around in the water. When we got out of the water my neighbor had a hard on. When he saw that I saw it he said. "Don't be embarrassed. An erect penis is a natural reaction. Something else that is natural is masturbation." Mr. M started to masturbate right there in front of me. This got my body excited and I got an erection. Mr. M moved over to be next to me and started to fondle me while continuing to masturbate himself. The fondling turned into masturbation. "Do you want to feel something more pleasurable than my hand" Mr. M asked. I nodded yes. Mr. M leaned over and started to suck my cock. His mouth was more pleasurable than his hand. It only took a minute before I reached orgasm. Mr. M noticed that my cock was sensitive after the orgasm and continued to suck on it. When I tried to pull away Mr. M laid on top of me and told me "Stop squirming! I know it is painful but I know what I am doing! You'll thank me later". He was right. The sensitivity pain became pleasurable as he continued to suck my cock and brought me to another orgasm. Afterwards Mr. M lay next to me and masturbated himself to orgasm. I still remember the cum shooting out of his cock that day. Mr. M and I went on many more fishing trips. Never once did we go beyond oral. It was Mr. M who taught me that masturbation and oral sex was natural. For one of my birthdays Mr. M got the two of us a hooker and showed me how to fuck a woman. Mr. M also showed me how to DP a woman that night. Good memories.
We continue to rest a bit and watch the video. On the video you could tell Coach H just cummed in his wife as his cum started to drip out. Coach H switched to another video of him and his wife having sex. After watching that for a few minutes he says "Now it is my turn for fun.” I moved down and started to suck the Coach’s cock as he watched the video. After awhile Coach H tells me that he wants to fuck me. He roles me to my back and slides me to the edge of the bed. He parts my legs and kneels down in front me and starts to lick and finger my ass hole. After my hole is nice and relaxed Coach H stands up and moves in. I look over to the TV and notice that in the video Coach H and his wife are in the same positions that Coach H and I are in now. Seeing him thrust his cock into his wife I can’t wait to feel his cock in my ass. I do not need to wait long as the head of Coach H’s cock begins to push against me. I relax and feel the head of his cock enter my hole. Coach H leaves the head of his cock just inside my hole for a moment (image: the part of the head that curls in to contact the shaft is just visible from the outside) before he continues to slide his cock in. It feels good having his cock inside me again. It did not take the coach long before his thrusting fell into the rhythm of 5 long deep thrusts, two short sallow thrusts, a long thrust in, two short deep thrusts, then back to 5 long deep thrusts. I looked over and watched the video some. On the video Coach H had the same thrusting rhythm as he was doing with me. After several minutes Coach H pushes me far enough onto the bed that he can climb up. My legs are pushed up to and out from my chest as Coach H slides his cock back into my ass. I turn to the TV and see that again we are in the same position as on the video. Coach H notices that I noticed the video. "Yep I am going to fuck you just like I fucked my wife on that video. Except I'll be fucking your ass". As he thrusts Coach H leans in and kisses me. In the next position I (and his wife) am on our left sides and Coach H is straddling our left leg as he thrusts. Next Coach H is lying on his left side behind us as he thrusts. After that position Coach H is kneeling behind me/us while I/she am on all fours. Coach H deviates from the video as he starts to slam his cock harder and faster into me and moans. I can feel his cum as it begins to leak out my ass. Coach H takes his climax in stride and continues to thrust his still hard cock in and out my ass. Next on the video the coach is on his back and thrusting his cock up into his wife. Coach H and I role as one so he is on his back and his cock never leaves my ass. Coach H begins thrusting his cock up into me. More of his cum leaks out my ass. On the video Coach H starts to thrust faster into his wife and you can hear him moan as he cums in her. You can see his cum leak out of her vagina as he continues to thrust. I wonder if this is what it looks with him and me. As if on cue Coach H starts to thrust faster into me. It takes a little longer but Coach H begins to moan and lets the flood gates open as more cum spurts out of his cock and into the depths of my ass. I get off of Coach H's cock. It is still hard and shines with his cum. I squeeze some of his cum out of my ass and into my hand. I begin masturbating with that hand. His cum is very good lubricant. I kneel to the side of Coach H's chest. Coach H reaches over and fondles my balls. It does not take long before I squirt my third load of the evening onto Coach H's hairy chest.
Coach H and I lay on his bed resting. Our hands on each other's chests. "That was fun" I tell him. "It was fun for me to." he replies. We agree to meet again at his place the next time I can arrange it.