The what ifs of the memories of the past.
When I was 16 years old, my mom use to work as a cleaning lady at a motel with another woman. She had became friends with her and I use to go with her to her house every once in awhile. Well, I met her son and daughter when I went there.
I hung out with them and played videogames for the most part while my mom and their mom went out back to go tanning and we use to wrestle. And one day I was there we were hanging out and the boys sister was telling me how he can make his wiener grow. At this point in time I already knew I liked boys so I was curious but didn't say anything.
Later that night, I ended up staying the night. His sister didn't stay in the room but I did. He grabbed my hand and made me grab his dick and told me to smell it. Of course, I was too shy at the time so I never did anything. I mean I did Jack off in the bed when he went to brush his teeth but he never knew.
But this is where the story comes into play. The what if. If only I would have done it, but I can only image but I would have grabbed his dick and started to stroke it. I know at that time he had never been with anyone so I know he wouldn't object to it. I would have then asked to try something. Same as I never have done anything like this before at the time.
Once he said yes, I would have gone under the blanket and started to suck his dick slow at first and start to speed up. Once I knew he was getting close I would stop and ask if he wanted to try something else. I'd wait for him to ask if he wanted to fuck for the first time and strip down and get on my hands and knees and point my ass towards him.
Of course he knew what to do, he grabbed my hips and shoved his dick inside of me and thrust inside of me as hard as he could. It shocked me at first but he was pretty small, but his being the first time fucking anyone, he was actually pretty good. He hit the right spot every single time. He didn't slow down at all, he kept fucking me harder and faster.
With each trust I could feel his body starting to tremble. I knew he wasn't going to last too much longer, so I gripped the blanket and held myself steady until he was ready to cum.
A few more thrusts, he said that he had to pee. That made me sure that he was ready and that he had never cum before. So I said to him to go ahead. He said ok and and he started to slam it inside me as hard as he could. Seconds later, I felt his dick pulse a few times before he squirted all of his cum inside of me.
Once he was done, he lay his body on top of me then pulled out as it dripped out of me. I then roll over on my back with my dick pointing straight in his face so he grabs a hold of it and starts to jack me off. He seemed to know what he was doing as he gripped a hold of my dick and started to stroke it.
What caught me off guard was when he wrapped his lips around it and started sucking me. His head bobbing up and down on my dick got me closer to the edge and I wasn't going to last much longer. I told him I was close and he then started going faster. I few seconds later, my dick started to pulse and I grabbe the top of his head and pushed him further and held him while I shot my load into the back of his throat.
Surprisingly enough he swallowed every drop, including licking the tip afterwards. Afterwards we lay down and went to sleep and we haven't seen each other since then. But I wish we could see each other again and experience something that could have been.