When I was younger I would always enjoy seeing many different pictures of cocks in porn. When I turned 17 I posted an ad on craigslist looking for my first gay experience. An older bear type man had messaged me and got my attention. We discussed that I have never had sex before nor have I gave oral over email and he got even more interested in me. I finally broke out of my shell and went to his house. I remember him answering the door naked and him telling me to take off my clothes within 5 minutes. It was kinda awkward and exciting at the same time. I have always secretly wanted to suck a dick and take it in my ass. After I got naked he took me to the bathroom and made me shower and clean up. When I got out of the shower I went back into the living room to find him stroking his cock to some gay porn on his couch. When I walked in he immediately told me to get on my knees and suck his dick, when I put it in my mouth I could feel the warmth of his slowly hardening cock. I enjoyed the feeling of his cock grow in my mouth while I gave him oral trying my best not to let my teeth grind up against his cock. Once he was hard his dick completely filled my mouth up. He was rock hard at this point, and I as well was rock hard from just blowing him. At this point he got up and got some lube, a butt plug, and some poppers. We proceeded into his bedroom where he layed down a towel on top of his bed where we were going to have sex. He started off by just getting a little lube and putting it on my asshole and his fingers. He started with his index finger. It hurt at first, but once my ass had gotten used to his finger it had started to feel pleasurable. His finger would hit this part inside my ass that instantly got me harder. He started to slide his finger in and out. And then he handed me the bottle of poppers. I was 17 and he was 49, I had no idea what poppers was. But I'll try everything once. So he showed me what to do. I took a deep breath and then inhaled the poppers, within seconds I felt a sudden rush go through my body, I could feel my heart beating in my ears (it was a weird feeling) I also felt very tingly and horny as well. Once I used the poppers he said that this will hurt a little bit but the pain will go away. At that point he inserted his middle finger in my ass while his index finger was still in there. Yet again it hurt at first but then started to feel amazing. He then proceeded to repeat sliding his two fingers in and out of my asshole. Once he was done with fingering me. He lubed up his butt plug and slowly pushed it into my asshole even though I was flinching from the pain of my ass stretching. He didnt even stick the butt plug all the way in, he got half way and said, that will be enough to fit my cock in there. He continued to twist the butt plug around to make sure that my ass will be just big enough to fit his head in. He then made me lay on the bed with my head off of it and upside down. He then said to suck him off again so he can get hard. When I looked at his cock I realized he had lost his boner. So I proceeded to give him the best oral I could give him, once he got semi hard, he started to facefuck me until he got rock hard again, at one point he thrusted his cock so deep in my mouth, that it forced my mouth open to let air flow through my mouth Instead of my nose, which caused me to cough and gag on his cock. I felt his hard smooth head hit the back of my throat with force. It was painful, yet very hot. Now I was recovering from that harsh blow to the throat. But before I could say anything he said "turn around, on your hands and knees" so I followed his Instructions, as I got into position, I looked behind me and saw him covering his cock with lube, while I saw him lubing up his cock, I realized that his cock was average length about 6.5-7inches. His head was the size of what an average 7 inch cock should be. But his shaft was what made his cock different. The shaft of his cock gradually got thicker from the head all the way to the base. The thickness of his cock where it was at the base was double the size of how thick it is at his head. I then said "man thats a really thick cock, I dont think I can take it" he then looked at me and said "just relax" and then handed me the poppers again. I took a deep breath again, and this time I inhaled twice through both nostrils. I got the rush going through me again. At this point I was ready to face the pain until I got used to his cock. His head didnt hurt when he inserted it, but as he slowly thrusted his cock deeper and deeper it started to burn and hurt very badly, I had to pull away cause the pain was too much. He said its okay its just that he needed more lube for it to hurt less, so I let him lube his cock more to the point where u couldnt grip his cock even if you tried. He started at it again. Except this time it didnt burn, it was just painful. He slowly started working on my ass by squeezing it and spanking it lightly while he slowly inched deeper Into my virgin ass. And then he hit the same spot he hit earlier with his finger. I can feel my cock standing as tall as it could be. So I decided to start jacking myself off. He finally had gotten balls deep inside of me, and I could tell how far his cock was inside me and how exact the shape was just from feeling it throbbing in between my butt cheeks. He then whispered to me "is this what u wanted boy?" I replied "yes daddy" and he started to slide his cock all the way in and all the way out, with deep thrusts grabbing my hips. It hurt when he took his dick out and repeatedly inserted it inside my ass. But the pain went away, now I could feel his cock going in and out, in and out. I was enjoying it. I came so hard from jacking off while he fucked me from behind, after I came I startedto lose interest in continuing to have sex with him, but I decided to let him finish. Soon after I came he had pulled his cock out of my ass and started moaning deeply, he started to take short breathes with his moan, "ugh ahh mmm" I felt a sudden warmth on my back it was a slim line reaching from my lower back to my shoulder, each short breath was his load shooting all over my back. Afterwards he got his camera and took a picture of my back covered in cum, I looked at it and was amazed, I had never came as much as he did in my life. He then asked me how I liked my first time having gay sex? I said I loved it and proceeded to get dressed. And I had left I had some mixed feelings about my first gay experience. It was looked down upon by society, but its not a big deal at all. I was a bit scared of going back again, because it was awkward for me, I rarely talked to him when we fucked. But I did enjoy sucking his thick cock and feeling it slide in and out. About a week later he had emailed me, he said he enjoyed his time with me and would like to be Friends with benefits, along with that email he gave me a number to text, so I decided to just not care about what society thinks, and just wanted to enjoy myself, so i texted him letting him know it was me. He told me that the first time is always weird. I believed him, he wasn't wrong about telling me to relax when he penetrated my ass, he wasnt wrong about the poppers either, so he shouldn't be wrong about that either. This time I went late at night after work. I knocked on his door very lightly since it was midnight and he lived in an apartment complex. I didnt want to wake the neighbors. He answered the door, naked again. I found this very hot, he would open the door and hide behind it so no one can see that he was completely nude but after I walked in he shut the door, and there he was, his big attractive bear body, and his cock semi hard from watching gay porn, I undressed myself in front of him while he fondled with my ass and cock, then we went to the shower and he said to hop in, so I did, except this time he came inside with me. He got the soap and started lathering my back all the way down to my ass, then he turned around for me to do the same to him. After we rinsed off all the soap he started to spoon my ass with his cock, I could feel his cock getting bigger and harder just from spooning me. We got out and dried off, he offered me some bud and we smoked a little while we sat down in the living room, while we were sitting, he started plauing with my cock, so I decided to start playing with his as well, he then said "so I assume u enjoyed last time" I told him that it was painful at first, but then it was pleasurable. And I also told him that I lose Interest as soon as I cum, so he said this time to let him take care of it. I voluntarily got down and started giving him oral, and as soon as he reached his full erection he took me to the bedroom and proceeded to lube my ass, his fingers, and cock. He used his fingers to stretch my ass just enough for him to fit his head in there. Then he started to slowly thrust against my ass. It wasnt as painful this time, and I enjoyed myself even more than last time, this time I didnt come while he was fucking me, I decided to hold off and just enjoy the ride he was giving me. Halfway before he was done he shoved his dick as far as he could up my ass as hard as he could and he whispered in my ear "u like daddy's thick dick" I replied "yes daddy, I love ur thick dick" he then said "your ass is mine now" I thought to myself "whatever bro, ur just a phase in my life, this is my experimental phase and I'll get over it just like I did with videogames and skateboarding. This time when he finished he came inside my ass. He pulled out and as soon as he did, I felt his cum drip out of my ass and down my ballsack. I got dressed and left, I went down to the car and realized I had a boner still, so I decided to jack off in the car, ot was 2am and no one was awake, I started jacking off and when I came, I shot so hard that my cum hit my roof, luckily all of my cum didnt shoot that high, but that night was one of the biggest times I shot my load. I got home and fell asleep by 3am, and while in bed all I could think about was his amazing thick cock. I woke up at 10am the next morning. I had morning wood and I thought to myself "round two?" I texted him to see if he was up yet, he replied that he was wide awake and really horny. I went over and we had sex, after sex this time we started talking about when we figured out that we were attracted to men, and we slowly realized that we had many similar thoughts about it when we were younger. So after the 3rd meet up, we started to become actual friends with benefits. He also informed me that he had another guy that he hooks up with on a regular basis, but he prefers me cause he likes younger guys, I told him that I didn't mind him having another sex buddy, and that it actually sounds kinda hot to fool around with 2 guys. We did have a 3 way and it was super steamy and erotic. I am now 22 and he is 53, I still go over to his house at least twice weekly to suck and fuck his amazing cock. And we have 2 planned threesomes each month with his other fuck buddy. This old man, took my anal virginity at 17, and I havent regretted a day since it happened. I know many of you will think its wrong to have such an age gap between partners. But I am very attracted to older overweight men. And btw, he wouldnt be considered a pedophile for that since I had given consent, and the legal age of consent in my state is 16. This was my story about how how I lost my anal virginity to an old man and became his regular sex buddy.