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In college, I had a friend who introduced me to some kinky stuff. I trusted him a lot and liked him. One day I was hanging out at his place with him and his friend that I didn’t know too well. I was wearing gym shorts, a shirt, a snapback, and shoes and socks. We were sitting around drinking beers and chatting the three of us. Somehow the fact that I can do a handstand came up in conversation and they asked me to demonstrate. I did but due to the beer and my shirt falling off it wasn’t very good. My friend’s friend suggested I just take my shirt off, and my friend agreed and quickly stripped my shirt off me. I redid the handstand and held it longer. I didn’t know where he had put my shirt so i just chilled shirtless for the rest of the time. A beer or two later, My friend mentioned he had gotten some bondage equipment and asked if i wouldn’t mind modeling it off for him and his friend. I had been tied up before by a guy and since it wasn’t a sexual thing this time, I had no reason not to.

My friend showed me his set up, a chair with arm cuffs attached and a set of stocks attached to a nearby table slightly higher than the chair. When I sat down and put my feet in the stock holes, this had to effect of raising my feet and making my shorts slide down my thighs slightly. My friend tied my hands to the cuffs, which were angled so my arms were away from my body, while his friend closed the stocks over my feet. I tested out my bonds and realized my range of movement was severely limited. I looked up at them, expecting them to be looking at how my range of motion was limited or maybe how the arm cuffs looked or something. Instead…

“So bro, are you, um….ticklish at all?” My friend asked. I realized what his plan was and freaked out, thrashing in my bonds to try and prevent that from happening to me. Unfortunately for me, I am extremely ticklish everywhere on my body. I can’t stand being tickled. It’s true torture!

“Um…no im not tickliyyyyish at ahhhhhhhll” I said as i felt his friend’s nails drag along my helpless soles. He laughed at my reaction and dragged his nails down my soles a second, third, fourth time. I squirmed in my bonds but there was nothing I could do to shield my feet from his fingers, and each time he went down my foot I got closer and closer to letting out a gigantic and uncontrolled laugh.

“Cmon guys don’t tickle ahahahah tick hahahahaha” I couldn’t get my sentence out as my friend tickled up and down my sides, much more firmly and aggressively than his friend was doing on my feet. I tried to close my arms but the cuffs held them away from my body, adding to my vulnerability. All i could do was do my best not to react and hope they’d get bored and let me go. But then I heard…

“Hey, cover up his feet with this,” and after a moment I felt baby oil being slathered onto my feet. My friend’s friend held up a small hairbrush for me to see. I looked into his eyes in panic and said “No cmon bro PLEASE don’t use that Im serious Im so ticklish bro I can’t take it!” He listened to me for a moment then took the brush and dragged it mercilessly over my helpless sole, tickling over and over while I began laughing uncontrollably.

The sensation on my sides and feet was too intense and I realized to my horror that I had a hard on. I hoped they wouldn’t notice, but as some point my friend’s friend stopped tickling me and said “Um dude are you not wearing underwear?” I looked at him and saw that he was looking up my shorts and could see my cock and balls.

“I…uh…cmon bro don’t look!” I blushed beet red and stared at the ceiling, trying to avoid eye contact with him.

“Oh I’m looking dude, you have a nice tool and a great bush!” his compliments made me blush even harder.

“Do you want to tickle him there?” My friend asked his friend. I glared at him and was about to demand he let me go, but before I could, his friend said “YES!” enthusiastically. My friend picked up another tickle toy, a stiff feather, and handed it to his pal. My friend held my shorts open so his pal could have easier access to what he wanted to tickle. I soon felt the feather sliding along my balls and along my shaft. I screamed in ticklish agony and my legs began shaking but due to my bonds I couldn’t prevent him from tickling me there, and I realized that my erection had gotten even more firm from the feather tickling, and I am sure he saw this too.

They laughed at my predicament, and my friend was enthralled with my reactions to the feather tickling my genitals. He guided his pal too, saying things like “Make sure to get along the curve of his balls” then giggling hysterically when the new sensation made my laughter go up an octave. They both noticed when a spot of precum appeared on my shorts. They teased me about it and asked if I needed a break. I said yes and began to beg for one but they just kept tickling.

After a few minutes the guy holding up my gym shorts let go, and the guy with the feather grabbed hold of them himself, while the first guy began tickling my feet again. I couldnt take this sensation and told them that they had to stop or i was going to reach the point of no return.

“Bro, you’re really gonna cum on yourself while we are tickling you like this?” feather guy asked

Only the best of friends pants you exposing your tighty whities and wedgie you while you squirm to be free :-) 

We were bopping to the music and my friends were laughing and talking shit as we floated around with the pulse of everyone else, when I felt a hand on my back, clearly intentional contact. It only lasted a second though, and there were so many people around me I had no way of knowing whose it was, so I ignored it.

Next thing I know, my best friend Kyle is behind me, with his arms gently wrapped around my waist, and his hands travelling lower towards my shorts. As I got ready to turn around and question him, he whispered in my ear,

“Don’t turn around, just act natural and let it happen bro.”

Maybe it was the alcohol, maybe it was just the rush of the moment, but I obeyed, and he slipped his hands down my shorts, grabbing a firm hold on my dick, which, to my surprise was almost immediately rock hard. The way we were all bobbing in the water meant his boner was now rubbing against my ass through our shorts and I could feel his muscly chest pressed up to my back. It was the most unsettlingly comforting feeling I’d ever experienced.

I continued to look straight ahead, trying to focus on what my other friends were talking about, but that was rather difficult when your best friend is stroking you with one hand and stripping you with the other. My shorts slowly drifted down my legs and off into the abyss of the pool. He must have done the same to his because suddenly I could feel his bare dick against my skin and it sent shivers down my spine.

This fucker had his dick against my ass, his hands around my cock, and he was still talking to our friends like nothing was happening! I couldn’t believe it, but I also didn’t want it to stop. I had never felt my body tingle so much as it was now.

Without warning, I felt him push his dick up to my asshole, and I could feel myself stretch to allow him inside. It hurt like HELL. I had to clench my fist to keep myself from screaming, but he kept pushing and then with a pop he was all the way inside me and I nearly blacked out from the intense pleasure I got from his fat cock pressing against my insides like this. Surrounded by other people completely unaware that I was getting cored out by my best friend.

He let out a muffled moan as he started to pump away, matching the beat of the song blasting from the speakers only feet away. I could hardly hear the music though over the throbbing in my ears from every time he hit my prostate. This was the first time I’d ever felt a man inside me and it was amazing! While he fucked me he was stroking me vigorously, and I could already feel myself getting close. Was he really going to go all the way like this right here?

“I’m gonna cum inside you right now bro, get ready.”

That put me over the edge. He was jerking me just perfectly in rhythm with his thrusts, and I came harder than I ever had before, but he didn’t stop stroking me, and I started to convulse in pleasure as my head was so sensitive post-nut, and he was wringing it out harder and faster, my cum giving him even more to play with on my skin. Then, I felt it: the final shove. He pushed himself even further inside me and unloaded. I felt every pump of his warm cum shoot its way out of his throbbing cock, and I felt him shake from the orgasm. I never wanted it to stop.

After a few moments of us floating there, still completely unnoticed, him still inside me, Kyle whispered,

“Let’s go inside and find a room, I want you to do that to me now.”

I felt myself go hard all over again. Without turning around, I nodded my head in the affirmative, and I felt him slip out of me. He ducked under the surface for a moment, then came back up with both our shorts. We slipped them on and excused ourselves from our friends, and made our way out of the pool, across the yard, and into the house.

I had never been to this house before, and it was completely dark inside. The music same was playing on the house’s surround sound system, and there seemed to be speakers on full volume in every room; however, the house itself was completely empty. Kyle led me through the vast kitchen, into the hallway, up some stairs, and into the first bedroom. This room was huge and had windows looking down onto the pool below. Off to the side there was a private bath as well.

He pushed me down onto the bed and climbed on top of me, and kissed me for the first time. I don’t know why, but even after all that just happened in the pool, I wasn’t expecting this. It felt so good though, and I didn’t stop him. He ripped my shorts off again, and slipped his way out of his own, and pressed our hard dicks together, stroking them slowly and firmly. I let out a small whimper of excitement as his tongue explored the insides of my mouth. I could smell the sweat on his skin mixed with the salt water from the pool.

“You wanna fuck me now or what?”

I again nodded my head, and he scooted up further, straddling my torso as he lined my throbbing cock up with his hole, and sat down. Now I’ve fucked many girls in my day, but not any one of them compared to what I felt the moment I slipped inside my best friend’s ass. It was so warm and tight, and I could feel his muscles contract around me. I couldn’t help it, I moaned so loudly. He started to ride me, jerking himself off with one hand, and feeling my body with the other. He kept kissing me, too, which was absolutely euphoric.

“I want you to cum inside me this time.”

I grunted in approval as I could feel myself once again getting close, the sensation completely overwhelming and out of this world.

He kissed me so tenderly as I climaxed, this one feeling even better than the one in the pool. I shot my cum deep inside my friend, and I knew in that moment our relationship has completely transformed. There was absolutely no going back now.

When I had caught my breath, Kyle climbed off me and took my hand and pulled me off the bed and led me to the bathroom. The shower was massive and cavernous. He closed the door behind us and locked it, before pushing me backwards into the shower and pinning me up against the cold tile wall, my arms stretched out above me, and his tongue once again buried in my throat.

He ground up against me, our dicks still hard and rubbing together, and then he turned me around, used his foot to spread my legs apart, and without any sense of gentleness he shoved his dick back up inside me, which caused me to scream in surprise and pleasure. He was huge, I’m not joking. It was so fucking awesome. He fucked me again, and came inside me for the second time that night. Afterwards we showered together, making out and touching each other all over, before going back down and joining the party. Our friends never questioned it.