My senior year in college I was living with my girlfriend of about 3 years in a two bedroom apartment. We were having some troubles in the relationship so I was sleeping on a futon in the other bedroom for a week or so at this point. It was late and I was horny as hell so started watching some porn on my phone, which quickly turned to watching videos of younger guys sucking and getting fucked by older guys. My favorite. Grindr had pretty much just came out and I hadn’t really heard of it, but a quick ad came on before one of the videos so I rushed to download the app. I had some prior hookups using Craigslist and loved it, so I thought why not. I created a profile and left it pretty blank, but made the title “cocksucker” and started messaging guys and just saying “hi.”

Before long I was messaging a handful of guys and sending picture of my ass to most of them. I quickly grabbed a couple of my butt plugs from the hidden stash I had and started playing with myself while talking to them. There was one guy who stood out over them all. He was exactly the type I’m always looking for. Late 50s (I was barely 22 at the time), bit of a belly, and a nice cock with big low hanging balls. I asked him what he was looking for and he told me he was a total top just looking for a boy to play with from time to time. I told him I was still a little inexperienced because at that point I was, and he told me not to worry, that he would take it easy on me and help teach me how to be a submissive bottom slut to an older man. I was hooked. It wasn’t 5 minutes later that I was getting dressed and ready to sneak out the door and drive to his house. I left my butt plug in my ass, slipped on one of my girlfriend’s thongs, and made my way out the door as quietly as I possibly could.

After a short 5 minute drive to his house, I was nervously walking up to his door. Before I made it to the front steps he opened the door and invited me in. I asked him where he wanted me to go and he said we could stay in the living room. He walked past me and sat down on the couch and immediately slipped off his athletic shorts exposing his soft cock laying in a bed of gray pubes. I wasted no time dropping to my knees and slurping his cock into my mouth. I moved my tongue around his cock feeling him stiffen up. I lifted my head off him and watched his cock grow between strokes, licks, and kisses. When he was fully hard he asked me to stand up and get naked for him. I did as I was told. His eyes lit up when I took my sweats off and he noticed the black thong I was wearing. He grabbed my hips and spun me around before slapping my ass hard. Then I felt both hands grab each of my ass cheeks and spread them apart. He laughed and said “a butt plug too huh boy?” I whimpered a “yes sir” as he slapped my ass again. “Come here and suck my cock again.” I spun back around and dropped to my knees before slipping his dick back into my mouth.

After a few minutes he asked “are you going to keep your ass plugged or are you going to give that ass up to me tonight?” I looked up at him and said “I wasn’t sure if you wanted to fuck me tonight or not.” He just laughed out loud and said “I think you knew showing up here like that you’d be getting fucked tonight.” Then he asked “how often do you leave your girlfriend at home to get fucked by old men?” I said “this is the first time really.” He smiled and said “it won’t be the last” and stood up off the couch.

He left the room for a minute before coming back in with a bottle of lube. He grabbed me and spun me around forcing me to my knees on the couch with my hands on the back of it. I started pulled my thong off and he told me to leave it on. He moved it to the side and started tugging at my butt plug. It popped out and he threw it to the side. He spread some lube onto his cock then slipped one, two, three fingers into my asshole. Then in a hurry he slapped my ass with one hand while lining his cock up with my asshole with the other and I felt his cock head push into me almost instantly. I let out a little whimper and looked back at him as his slid the rest of his cock into me until I felt his hips pressing against my ass.

He held himself inside me for a bit and let out a heavy sigh while digging his hands into my hips. Then he started fucking me with a pretty fast pace. I wasn’t ready for it at first but after a while I settled into the pretty steady rhythm of his fucking. Feeling his balls slap against mine while he gripped and slapped my ass pretty regularly. With every thrust I tightened my grip on his cock while he fucked me. I absolutely love having my ass slapped and he caught on pretty quick with every squeal and whimper. Eventually he slowed his pace down and said “I don’t want to cum yet” while he came to a complete stop with his cock buried all the way in me, his belly resting on the top of my ass. He had his left hand up on my shoulder pulling me back, and his right hand gripping into my hip.

Through his heavy breathing he asked me how long my girlfriend and I had been together. He seemed to really like that fact that I was cheating on my girlfriend with him, and he definitely loved the age gap as well. I told him we had been together for over three years. “When did you start letting men fuck you behind her back?” I told him a little over a year ago and he continued asking me questions while he slowly started fucking me again, taking his time pulling the whole length of his cock out, then pushing himself back in slowly. I answered his questions while gripping his cock with my ass, telling him about the first time I cheated on my girlfriend with an older man I met at a bar who bought me and my friends drinks all night before taking me home and fucking me until the morning.

By the time I was finished talking he was pounding away at my ass again. Then he stopped suddenly and said “I want you to ride my cock until I cum.” I quickly agreed and he pulled me off the couch and sat down. I asked which way he wanted me to face. He said “I want to watch your ass bounce” so I spun around and faced away from him. He grabbed my hip and aimed his dick at my ass while pulling me back down on him. He groaned and said “fuck yourself with it” and I wasted no time at all. I bounced my ass on his cock like my life depended on it. Within a minute he told me he was about to cum, I think he was expecting me to get up but I wanted his load in me. I continued bouncing until I could feel his legs tense up and he basically started screaming as he came. I slammed myself all the way down, tightened my hole around his cock, and grinded my ass back into him.

After a bit I felt his body relax and I started bouncing on his cock again until he went soft and I felt his cock slip out of me. He grabbed my hip with his left hand and said “don’t move.” Then I felt my butt plug slip right back in me with zero resistance at all. He moved the thong back over the plug, slapped my ass, and said “take that home to your girlfriend” and laughed to himself.

I went to the bathroom to get myself together and cleaned up and little and got dressed. I opened the door and started to leave when he grabbed me by the arm, groped my ass, and said “I can’t wait to see what you have to offer next time” and let me go. I drove home and quietly made my way back up to my room. I jerked off furiously before falling asleep. When I woke up still wearing the thong and the unmistakable feeling of my ass being plugged, I jerked off again, opened up Grindr, and sent him a picture of my ass still plugged filled with his cum. This man probably fucked me 100 more times during my senior year. In his house, in our cars, in public, and in my apartment with my girlfriend asleep in the other room.