When I was 16 I had two male friends that I would fool around with. The first was Jason, he was a year older. The second was Joe, a year younger. Jason and I had been doing things like masturbate in front of each other for a few years and it had recently progressed to him asking if I wanted to try sucking each others dicks. I was reluctant at first, eventually came around. Joe was very much a fem boy. Everyone knew he was gay. I only hung out with him because I was nuts about his older sister. Thats how that started, he would dress up in his sisters clothes when she wasn’t home and we would make out. Eventually turning to mutual oral there as well. Neither of them knew about the other, mainly because I was still embarrassed and scared people would find out. One day it finally reached a point where Joe wanted me to fuck him. Jason had mentioned that he wanted to try it sometime as well too but we hadn’t gotten there yet. Then at our usual sleep overs, he brought it up again. Not wanted to let him know I fancied myself as a professional already, I agreed to try it. We both tried but neither of us ultimately wanted a dick in our ass. So I confessed what I had been doing with Joe and told him that Joe was interested in having a threesome. I invited him over.
When Joe got to my house he was wearing a coat that when he took off he was wearing some of his moms lingerie. It was a black lacy see thru thing that looked great on his feminine body. Jason and I wasted no time pulling our rock hard cocks out. Both of us sitting on the bed, Joe knelt between us taking a cock in each hand. Joe began licking and sucking both of our dicks. The moment became too much and Jason and I started kissing. Our tongues danced around each others mouth as we both sat there being pleasured. Jason got up and positioned himself behind Joe. He slowly entered him sending all three of us into bliss. I could see how good it felt by the look on Jasons face and I certainly knew what it felt like to be inside Joes tight ass. As Jason finally broke thru, Joes sucking became more rigorous. I was about to explode, but Jason beat me to it. I could see he had every inch of his 7″ cock inside Joes ass as he came. Seeing that only made me cum harder. Joe swallowed every last drop I put in him. After a short cool down, Jason and both began playing with Joes little 5″ dick. Jason said he wanted Joe to try fucking him since he was considerably smaller than me. This time Jason handled it well, and Joe began fucking him. Not wanted to be left out I got behind Joe. There was still some of Jasons cum dripping from Joes ass and my big throbbing cock slid in with no resistance. Moments laters I feel Joes ass tighten up and he lets out a big gasp of air. Knowing that he just came instantly make me cum. The intensity of my second orgasm has me shaking so much that I slide out of Joes ass. Without hesitation and much to my surprise Joe turns around and starts sucking me. He sucked every last drop my balls had that night. The three of us had sex a few more times that night and continued to do so for another year or so.