Fun With my Girlfriend's Little Brother

I used to spend summer vacations with my girlfriend's family when I was in high school. She had a younger sister and a younger brother. 

The first summer the house we rented had my girlfriend staying in a room with her sister and me sharing a room with her younger brother. We’d do normal beach trip things all week and had a great time. At night her brother and I would head to our room and we’d talk for a while about all kinds of things. 

At this point my girlfriend was 15 and I was 16. He asked me all kinds of questions about girls and sex and it eventually lead me to ask if he had ever masturbated. He had no clue what it was. I asked him if he wanted me to show him. He responded by saying yes. I asked him to come over to my bed and I showed him on my hand and made a jerking off motion on my hand as if my fingers were my erection. I was so hard at this point and asked if he was hard as well. He said he was. I told him…

“It would be much easier if you took your pants off and I did it to you.” 

He didn’t want to so we both agreed we’d go under our covers and do it to ourselves. 

I could see his prick tent he was poking out from under his sheets though which got me hot enough to cum. He said he finished as well and we went to sleep.

The next summer we were staying in the same room again. I decided ahead of time to get more bold this summer. I was 17 and was regularly having sex with his sister and I was intrigued as to what it would be like to see her brother naked.

I whispered to him that I was going upstairs to jerk off. I went upstairs and 2 minutes later he came into the room. We both started masturbating under our sheets and I started giving him a hard time about him being scared to show me his hard on. I kept showing him mine with his face staring at my 6 inch hard on full of pubes. He kept deflecting but eventually gave in. 

He hopped out of his bed and he was wearing pajama bottoms. I told him to come over to my bed and made him lay down next to me. He then quickly pulled down his pants for a second and pulled them back up. I was amazed at his rock hard 3 inch dick with hairs surrounding the base of his penis. I moaned that I didn’t get enough of a look and he pulled it down again. I wasn’t going to let him not give me a good look this time so I held his pants down with my hand. What an amazing hard on he had. His balls were also tight as could be. 

Eventually everyone went to bed and I wanted to watch tv so I went down to the living room. After about 10 minutes he came strolling down and sat in the couch next to me. He looked at me and pulled his pants down and revealed his erection to me again. He said let’s masturbate. This is the first time we would masturbate together not under the covers. I agreed and we both pulled down our pants and started going at it. 

After a minute or two I couldn’t help it and I grabbed his penis and started jerking him off. I know he was my girlfriend's brother but it was hot and I had never touched a dick other than my own before. I was surprised with how hard and smooth it felt. He then grabbed mine and started doing me. Eventually he started to squirm around a little bit and started to lightly moan and pump his hips into my hand. When he stopped, I knew his orgasm was complete. He then went to work on me until I had the best orgasm of my life. My cum spurt everywhere for what must have been 20 seconds. 

This was my first experience with another guy and it was amazing. The next morning he approached me and said he was so glad we did that and he’s been wanting to do that and have me play with his hard on for a while after I taught him how to jerk off.