(Note: This is a story of sexual encounters among teenage boys - all characters are minors. It is strictly fiction and fantasy. It involves sexual practices that are considered unsafe and is not an endorsement of these practices. Please comply with the laws where you live concerning such literature, and read it only if you can do so legally. If you are offended by this sort of material, please find other things that will not offend you. If you like this kind of material, please donate to Nifty to ensure that this free resource can continue.)
I was envious of Buddy. His suave approach to getting laid had netted him a dozen and a half conquests during the course of the summer. Half of those had been virgins before Buddy got ahold of them. I had been one of those virgins, but I was very much okay with being a notch on Buddy's bedpost. I was also pleased to have Buddy as the first notch on mine. It had been past time to take advantage of the python, as Buddy had aptly named my boner.
So far, the only other guy that the python had penetrated was Jared. Jared was a great kid, and my fuck buddy for sure. But the python was anxious for some new adventures.
Lying in the sun at the swimming hole, I was still wearing my shorts because I wasn't the only one there. Further over on the grass was Ryan, a guy I knew from school.
At sixteen, Ryan was was the ultimate nerd - a technical genius and social misfit, complete with black-framed glasses. It was rumored that he had been one of Chad's coerced conquests after being photographed next to the swimming hole screwing his younger brother.
The way Ryan kept looking at me indicated more than casual interest. It was time to bait the hook.
I stripped off my shorts and went into the creek for a quick swim. When I came out, I sensually stretched my athletic five foot seven inch frame for Ryan's benefit. The snake between my legs got lots of attention, but what deserved more attention was my one hundred sixty pound muscular body. I had worked hard lifting weights, and I was proud of the results.
Back on my blanket in the warm sun, the python quickly grew to its full nine inches without any intervention on my part. A glance towards Ryan revealed that I had his full attention.
"Come on over and join me," I invited him. "There's plenty of room on my blanket."
A second invitation was not required. Ryan was on his way immediately.
"Pull off those shorts and get a complete tan," I suggested with a smile.
There was a brief hesitation, and when he was naked it was clear that nude sunbathing wasn't a regular habit.
"This is such a great place," I observed. "I've had a lot of fun since I started coming here a few weeks ago."
"I like it too," Ryan replied. "But I haven't been here for a while. Are you gonna be on the wrestling team again this year?"
"You know it," I assured him with a grin. "Wrestling's a lot of fun. You should turn out for the team. I see you at all the events, so I know you're interested."
"Thanks, but I'm not good at sports," he responded. "I would rather just be a fan. I especially like watching you. You've got some great moves."
"Thanks for the compliment," I replied with a grin. "We appreciate our fans too."
When I had seen Ryan at the wrestling events, he was often stroking his boner through his jeans. That suggested that he was a groupie rather than a fan, the difference being that groupies became sexually aroused by hot wrestlers.
Groupies also tried to develop a close personal relationship with their wrestler of choice. Ryan's comments about watching me and liking my moves suggested that I was his wrestler of choice. It looked like relationship development was under way.
"You may not be good at sports, but you're very good at other things," I said, continuing the conversation. "Rumor has it that you're particularly good at wiping contents off computers and closing online accounts for others."
"No comment," Ryan said. "But rumor has it that you also had a hand in curbing a particularly obnoxious jerk."
"I can't verify that either," I replied. "You never know about rumors."
I closed my eyes, enjoying the warmth of the sun. Soon, I felt Ryan's fingers stroking the python, apparently the next step in developing a close personal relationship. The big snake was happy with the attention, and it leaked a few drops of boy juice in appreciation.
There had been locker room discussions about groupies. Several of the guys had bragged about getting laid. Groupies wanted to be controlled, pinned and fucked while they resisted and tried to escape, so the experienced guys said. I decided to test that principle on Ryan. Nothing ventured, nothing gained.
Thanks to the wrestling and weightlifting, I was fast and strong. Before Ryan knew what had happened to him, he was pinned to the ground and I was grinning down at him. The grin he returned and the excitement in his eyes told me I was on the right track.
I smiled with smug satisfaction as Ryan struggled helplessly. Every move he made, I countered immediately. I had him right where I wanted him.
As Ryan twisted under me, the python slid into place between his wide-spread legs. He squirmed again, and the python popped its head inside. Ryan gasped, and a look of surprise replaced his grin as his fantasy of being fucked by a wrestler became a painful reality.
"Oh my God!" he exclaimed. "That thing is huge!"
"You bet it is," I replied. "It's not a computer simulation."
"I don't know if I can take it all," he said, sounding disappointed.
"I bet you can because you want it," I responded with a grin. "We're gonna find out, aren't we?"
The python slowly and relentlessly crawled inside. I grinned into Ryan's pain-glazed eyes as he tried unsuccessfully to escape. There was no doubt about the outcome. The python was going all the way in, and there was nothing Ryan could do to prevent it.
Once fully inside, the python began to slowly slither in and out . Each time Ryan struggled, it quickly crawled all the way back inside.
As the pain passed, Ryan's grin slowly returned. He was living the groupie's fantasy, and the python and I were happy to be making it a reality for him.
Ryan and I grappled for nearly a half hour, sweating from exertion in the warm late-summer sun. With each passing minute, the pleasure provided by the python steadily increased. Finally the the critical point was reached.
"I'm gonna cum!" I warned him.
As Ryan continued to struggle underneath me, the python escaped my control and took over. Fighting for traction on the blanket, I repeatedly pushed in as far as possible as the python released a flood of cum with each thrust.
Pulling the snake out, I sat back and smiled down at Ryan. At some point during our encounter, he had shot a couple of loads onto his stomach. On a whim, I reached down, spread his cum like finger paint, and signed the resulting work of art.
"I think you enjoyed that little wrestling match," I observed.
"Fuck, yeah!" he said with a grin. "I've wanted to do this with you for two years, but you seemed unapproachable."
"Well, that's changed," I replied, grinning back. "I'm ready to wrestle any time you are. I enjoyed the hell out of it too."
"I've got some friends who would like to do this with you," Ryan informed me.
"Send them my way," I replied. "I'll be happy to take them on."
"My brother Kevin would like it too," he added.
A light bulb went on in my head.
"My buddy Jared is gonna be on the team this year," I told him. "He's got a good-sized boner and he likes to fuck. He and Kevin are the same age. I bet Jared would like to have a little wrestling match with Kevin."
"I'll suggest it to Kevin," he replied. "I think he'll like the idea."
Not bad for one day, I thought, smiling to myself. A great fuck and contacts for more. Buddy's strategy of scoring by seduction at the swimming hole was fine for him. As a hot wrestling hunk, I would develop my own clientele by groupie referral. The python was going to get lots of exercise.
Lining up an opportunity for Jared had been an inspiration. Jared was a great fuck buddy, but the little guy needed some new adventures too.
(Watching from his hiding place in the bushes, Jared smiled. Eric had called him his buddy. He knew that meant fuck buddy, but Eric couldn't exactly say that to everyone. He had watched how Eric had fucked Ryan, and he was looking forward to doing the same thing to Kevin. Being on the wrestling team was suddenly developing fringe benefits, and Eric was becoming his mentor as well as his fuck buddy. It didn't get any better than that.)