Gay / Authoritarian / High School
This story is as true as I can remember it.
During summer vacations in my neighborhood, the guys would put on elaborate war games in the woods behind my house. They were so much fun, we actually continued them into our early high school years. This incident took place during the summer I turned 14.
Kenny was one of my good friends, and he lived across the street from me. A couple of times on sleepovers we had even gotten a little sexy. The first time, we were telling each other dirty stories, and just jerked off inside our sleeping bags. The second time, he got bolder, and reached inside my sleeping bag to jerk me. I reciprocated. While this was happening, he at one point drew his hand across my chest and that's when he discovered how sensitive my nipples were.
So that happened just those two times, and then here we were playing the war games. Kenny was on the other side. The rules of our game were that we had to act as if the sticks we were using for guns were real, and if someone got the "drop" on us, we either had to surrender, or if they said "bang" we were dead.
At some point Kenny surprised me and pointed his "gun" at me. I raised my hands in the air, and he said he was taking me prisoner. He told me if I told him where our HQ was right then he would release me (that was the goal of the game, to find and capture the other team's headquarters). I refused to tell him, and Kenny said, "OK, I'll have to take you to our dungeon and torture it out of you."
When he said that, I got immediately hard, and I think he could see it through the gym shorts I was wearing. Even before puberty I would get a "warm fuzzy feeling" when I saw a shirtless guy being tied up or tortured on TV or in a movie. Was I finally going to experience torture for myself?
Kenny marched me to his house at "gunpoint" and we went around back. He ordered me to climb the ladder up to his treehouse. His dad had built this really nice treehouse in their backyard. It was like a little cabin, completely closed in on all sides, and only accessible by a hole in the floor.
Once we were both up in the treehouse, Kenny asked me again to give up the location of our HQ. I refused, but this time added, "Even if you torture me I won't tell" to reinforce what I really wanted to happen. I think Kenny took the hint, that I was sort of giving him permission for what happened next, that I was telling him that I wanted it.
He ordered me to take off my shirt and stand with my hands behind my head. He slowly circled me, saying lots of things like a Nazi interrogator form a movie. At one point he reached out and gently pinched one of my nipples, and while I gasped, he didn't miss the look of ecstasy that came across my face.
He got a chair that was in the treehouse, set it down near me, and climbed up on it. The treehouse had a real roof with rafter beams. He reached up to the rafter above my head and started to uncoil two ropes that I now saw were tied to the beam a few yards apart. The dude had prepared for this! He had wanted to torture me! I started to get really hard.
One at a time he had me stretch out my arms into a Y and he tied the ropes to my wrists. He wasn't experienced at bondage knots (of course), so he tied a little too tight, but this was so hot I wasn't going to complain.
Then he stepped back looked at me for a while. I was pleased to see I could see a definite boner in his shorts as well. He told me since I wouldn't talk, he would call in their chief torturer. He went behind me and I heard some rustling for a few minutes. When he came out, he was shirtless, with two leather belts fastened around his chest, one above and one below his pecs. He was also wearing a black eye mask with eyeholes, probably left over from a party. He started talking in a German accent, and I caught on that he was now another character, the Dugeon Master.
He took off the belt from his shorts an slapped it on the floor a few times for effect. And then he whipped me with it, right across my chest. He really didn't swing it hard, but it was quite a shock, and immediately very sexy. I made sure to tell him he would never get me to talk no matter how much he tortured me. He then whipped me for quite a while, all over my chest and back, getting progressively more aggressive with the strokes.
After a while I was sweating, breathing heavily, and sagging in my bonds. He said that obviously I was stronger than he thought, and he would have to try a different torture.
He went into a little footlocker and brought out a bag of wooden clothespins. He removed a couple and held them open in front of my face. He asked, "Do you know what I'm going to do with these?" I shook my head no, but then looked down toward my now rock hard nipples. He laughed, and said, "That's right. You guessed it!"
He slowly brought the open clothespins down until he was holding them open over each nipple. As I looked down the sexiness of this was driving me crazy. Since I hit puberty I had been fantasizing about this. I sometimes put clothespins on my own nipples when I jerked off, and found that increased my sensations ten-fold. And now someone was going to do it to me while I was in bondage!
I told him, "I'll never talk! You can put those on me and I still won't talk!" I'm sure he could see the lust and eagerness in my eyes. So then he slowly allowed the pins to close on my nipples. Even though I'd felt it many times before, having it done by a friend while I hung helplessly in bondage was ten times sexier, and the sharp pain immediately turned to extreme pleasure. My cock was now tenting my gym shorts straight out and there was no mistaking it.
Over the next while Kenny put clothes pins all over my upper body. It really hurt at first, but was so sexy I settled into enjoying the scene. After a while he stopped and asked me again if I were ready to talk. Of course I shook my head no.
He seemed lost in thought for a while, then said, "Alright, then, you have forced me to use the ultimate torture." He stepped up to me and placed his finger inside the waistband of my shorts, and began to tug at it. He stopped and looked into my eyes, as if to say, "Is this OK?" I actually nodded at him, giving him a look of "Go ahead. I want this."
He then pulled my shorts and undershorts down quickly. I voluntarily stepped out of them and I was finally naked and bound helpless before my sexy best friend. He pointed at my cock standing straight out and said, "If I didn't know better, I'd think you were enjoying being tortured as much as I'm enjoying torturing you." I smiled at him, and he smiled back. It was the crossing of a line. We were both saying something we couldn't say out loud as adolescent boys in the 70s: we enjoyed playing with each other's bodies.
He got some more lengths of rope out of the footlocker and attached them to the legs of a small bed and a table, each of which were on either side of me. He had me spread my legs and tied the ropes to my ankles. He stood up, ran his finger along the length of my cock (which cause me to throw back my head and moan with pleasure), and said "Prepare yourself for the ultimate torture."
I was a little scared of what that might be, but all fear went away when he produced a bottle of baby oil and poured some all over my hard cock. He then wrapped his fingers around my cock and just was still for a moment. I think that was the sexiest moment of my young life up until then. It felt SO GOOD to have another guy's hand on my cock, while I was tied up and clothes pins were squeezing my sensitive nipples.
After a bit he began slowly stroking up and down my cock. He asked if I knew why this was the ultimate torture. I told him no. He told me I would find out. i soon did.
I was so horny it wasn't long before I was ready to shoot. My whole being was focused on cumming, But just when I was ready to go, he suddenly took his hand away. I looked at him like he was crazy. "Please, please don't stop!" I begged, all embarrassment and fear of being thought gay thrown out the window. He laughed and stood a bit away, staring at me and slowly stroking his own cock through his shorts.
After a while he came back and started again with the slow strokes. He repeated the torture I don't remember how many times. Every time I got close to cumming, he took his hand away and left me moaning and crying, hanging from my bonds. My whole world was now focused on cumming.
Finally I said it: "If I tell you where our HQ is will you make me blow?" (We hadn't heard the word "cum" yet, and we called an orgasm "blowing it.") He nodded yes, and I immediately blurted out the location of our HQ. He told me I'd made a wise choice, put more baby oil on his hand, and came over to stand right beside me.
With his dry hand he removed all the clothes pins. That was painful! Once they were all off, he began to slowly stroke me again. I closed my eyes and threw my head back, every ounce of my concentration on the wonderful sensation of his oily hand sliding back and forth on my rock hard cock.
Then he did something that blew my mind. With his other hand he reached over to my left nipple (he told me later that by this time he had figured out it was my more sensitive one) and began to gently squeeze and pull on it. That put me over the edge. Seconds later I shot a huge load, the first squirts of which shot halfway across the tree house floor. The orgasm was like nothing I'd ever experienced. I almost blacked out it was so intense.
After I calmed down, he untied me and gave me a roll of paper towels to clean myself up. I quickly left the treehouse as I think now that the sex play was over we were too embarrased to talk.
That was the first of many such torture games between us, though, and eventually I found it was almost as much fun to torture him as it was for him to do me!
Thanks for reading, and I'd welcome your comments or shared experiences. Email me at ibfoasm62@gmail.com