First Coupling - Part 3

First Coupling

a story by M…

Part 3

As the weekend went on the weather got rainy. The boat had a full canvas top and we stayed inside most of Sunday. We were nude enjoying a wine buzz looking at Playboys and using toilet paper roles on our erections. Let me explain. Earlier in the trip Jim found a small bottle of Vaseline. My dad used Vaseline to coat electrical terminals to prevent corrosion.

Jim took the cardboard tube out of the toilet paper roll and put a bunch of Vaseline in its place. Than he forced the roll over his penis and started to jerk it up and down. I followed his example. The feeling was like no other. Using your hands and oil was good. But this seemed to excite every nerve in my penis. In fact I couldn’t do it for long. I felt I was going to rupture something so I finished masturbating using my hand.

Later Jim was again masturbating but this time he greased his penis. I was watching him when he asked. Would I let him fuck me in my ass? We had talked about guys fucking and we both had thought about it. But to really fuck?

I lay there. I was very nervous. Sure, we had been messing around for a year. But his erection in me was kinda scary. His erection was a solid 7 inches, and he was a very strong guy. My ass was very small and I wasn’t sure I could take his boner. We talked and slowly masturbated our erections. I proposed a solution. Since he was bigger in body and penis size, I should do it to him first. If I couldn’t do it or it hurt him to much than no way could he fuck me. Jim agreed on the spot.

I remember him "draping" himself over one of the folding deck chairs in the boat. His ass very smooth and tight looking.

I put Vaseline on my erection and parted his cheeks. Looking at his anus I was totally thrilled. Even though I was a small guy my erection seemed much to massive to fit in his small asshole.

We didn’t know anything about foreplay or preparing an ass for fucking. I aimed my erection at his asshole and slowly pressed it into him. At one point my penis bent rather than enter him. Thats how tight Jim was. I got the Vaseline and put some around his anus than I tried enterng him again. I remember seeing some of the hair in his crack being forced into his hole as my penis entered him. He seemed to stiffen up and inhaled a loud breath as I slowly forced my boner way into his ass. It was a very intense sensation watching my penis slowly enter his ass.

I got about halfway in, his anal ring very tight around my erection. The hot feeling of his rectum along my penis was incredible. I slowly started to pump him. In and out. The vaseline quickly warmed up and helped my entry and pumping motions. While fucking him I saw pink tissue as I pulled out of him gripping my penis. With every stroke I went further into him. Jim was breathing very loud and at times would give a little grunt. I stopped, asking him if I was hurting him. He was in a very submissive state. Enjoying it as I slowly continued to make love to him.

I pressed my pubic bone tight against his asshole several times and just stayed deep in him for a few seconds on several deep thrusts. I didn’t get the chance to stay in him long. My nuts were very tight and churning with sperm. I ejaculated into Jim in a very short time. The sensation was again, something I had never experienced. I was out of control, my legs were weak and my deep thrusting uncoordinated into my lover as I spasmed and filled him with my immature seed. At the same time my sperm made the fucking easier as it lubricated my cock even more. I remember just slamming as much as I could into Jim while I was ejaculating. It was an incredible experience.

I withdrew from Jim almost immediately. As I did I saw Vaseline, sperm and some of his shit clinging to my penis. I went and used a towel to clean my erection off. At the same time I saw Jim turning around. He was flushed and very erect. I watched him; his cock really swollen. And he said it’s my turn.

I was very nervous but I promised him. I got over the same chair Jim was draped over. I remember feeling him grip my smooth tiny cheeks and spread them. He had greased his penis earlier and put the head against my hole. I felt him press it against my anus and breathed in at the pain. He stopped but that seemed as painful as if he would just continue.

I wasn’t sure but I told him to go slow. He kept pressing against me and I felt my anal ring continue to stretch. I gripped the chair with my hands my knuckles white and continued to feel him enter my ass. He pushed his cock against my unyielding virgin anus. I could feel pressure build as Jim pushed harder. I winced and squirmed from the pain and he stopped. He backed off and put more vaseline on his cock. Then he remounted me and started a second time to enter me. I tensed again, Jim waited a few seconds, after I settled down Jim started pushing again. As he pushed I felt him start to enter and streching my anus as well. After a few long

minutes I felt his glans pass my anal ring and he continued to enter into my rectum. All this time I was tense, my breathing very hard as he entered my virgin 16 year old ass. I was grunting and moaning, as I look back it was a combination of pain and pleasure, desire and intense passion.