I met Matt on Craigslist, back when they still had the personals section. He advertised as a vers bottom, and when I saw pics of his body and cock I knew I had to meet up with him. He had a massive 8.5" cock. I told him I usually topped at that point, so he was looking forward to hook up as well. He told me he was poz, but undetectable, but I could fuck him bareback if I wanted. I told him I prefer to use a condom (in those days) and he was cool with that and he had some available. He was also in a open relationship, but was playing separately. We agreed to meet up one Saturday afternoon.

I got to his place and he was every bit as cute as his picture. About 6 foot 1 and a nice defined body with rather thick legs. We exchanged pleasantries and quickly got down to business, stripping off our clothes and getting on his bed. He was a great kisser, but I wanted a chance to suck on his massive cock, so we got into a 69 position and went down on each other. His cock was amazing. Even though I was mostly topping at the time, I definitely thought about bottoming for him. Eventually he wanted me to fuck him, so he gave me a condom and lubed his ass up as well as my cock. It was a great fuck with him on his back. I came in the condom, and he he shot a load all over his stomach, chest, and even his face.

We had exchanged numbers and agreed to hookup again a few weeks later. Same thing as last time, making out, 69ing, Me fucking him on his back with a condom. This time though, about 5 minutes into fucking him I felt the condom snap as I thrust into him. I pulled out and looked down, seeing the condom gathered at the base of my 6 inch cock. I told him the condom broke and asked if he had another one. He said no, but I could keep fucking him if I wanted. I wasn't sure, but horniness overtook me and I plunged back into his ass bareback, eventually shooting my load deep in his ass, with him again shooting his massive load all over his chest and face.

We didn't talk for a couple years until I was going through old text messages and I saw some from him.

"Hey, what's up stranger?" I sent him.

"Oh hey" he replied a few minutes later. "Crazy I was just thinking about texting you the other day."

“Oh really?” I said.
“Yeah, kinda disappointed I never got to fuck you,” he replied.
“lol, no way, I was totally disappointed I never got to ride that cock of yours,” I told him.
“Wanna?” He asked.
I told him hell yeah, and would definitely be up for fucking him again as well. We got caught up, he told me he was single and had moved from a house to a condo on the east side. We arranged for me to come to his place in a couple days.

The day of I showered and made sure I was cleaned out. I got there and we hugged and went to sit on his couch. He had a really cool townhouse style condo. He got me a glass of wine and we talked a while. At one point we both put our glasses down and leaned in and started making out. He was an incredible kisser and we did that for about 5 minutes. He broke off the kiss and said he’ll be right back and went upstairs to his bathroom. I figured he was cleaning out and getting ready for me to fuck him. We hadn’t talked about condoms at all, so I wasn’t sure if we were going to use them or not. I was kind of excited at the thought of barebacking with a poz undetectable guy again, after all u = u.

I got up after a minute and went over to his dining room table, which was bar height, and had a couple art books on it. I leaned on the table and started looking through one of the books. I heard him come down the stairs and then he came up behind me and slid his arm around me. I saw him put a bottle of lube on the table beside me. He started kissing the back of my neck and nibbling on my ears. I instantly got hard. I leaned back and turned my head so we could kiss a bit more. As we were doing that he started undoing my belt and jeans, pushing them and my underwear down to the floor. I stepped out of them and kicked them aside. He broke off our kiss and kinda pushed me up against the table. I heard him take off all his clothes and then he lifted my shirt off me, leaving me totally naked except for my socks. He kissed down my back until he got to my ass crack.

He licked down my crack, spreading my cheeks apart until he found my hole with his tongue. My cock was rock hard, knowing I was going to get fucked. I had told him before coming over I might not be up for getting fucked, as at that time it really depended on my mood as I was mostly topping. He was cool with that, but with his tongue buried in my ass, I was more than ready. Up to this point, we still hadn’t talked about condoms, and my heart was pounding at the thought of him sliding his bare cock into me.

I felt him stand up behind me and he leaned into me, his cock standing straight up in between my ass crack and his stomach. He started slowly sliding up and down along my crack, which I felt get a little slimy with his precum. He grabbed the bottle of lube and stepped away from me a bit. I felt a couple lubed fingers play with my ass, getting it ready for his 8.5 inch cut cock. A few seconds later I felt his lubed up bare cock head press up against my hole. My cock was so hard, and I was sure if I jerked it even a little I would explode immediately. He pressed forward and I relaxed, letting my ass expand as his unsheathed tool slowly made its way into me. He asked if I was okay and I nodded. He continued sliding all the way until I felt his pubes up against my ass. There was a little pain, but not much. My ass just felt really full. He slowly started pulling out as I leaned my head back on his shoulder. He pulled out to just the head and slid back into his pubes, slowly settling into a rhythm of long dicking me. He started with both hands on my chest, but after a minute sawing his dick in and out of me, he he put an arm around my chest and another on my cock and slowly started jerking me with his still lubed hand.

I was in heaven. His cock stroked my prostate and his hand kept working my dick. There was a clock in my eye line and I watched the minutes tick by as I was barebacked by this poz undetectable stud. I could see a faint reflection of him fucking me in one of his paintings, glimpsing his 8.5 inch cock as he pulled nearly out of me each time. After a full 10 minutes of fucking me tip to base with his bare cock, I felt him start to shorten his thrusts and speed up a bit.
“I’m getting close, do you want me to pull out?” he asked.
I shook my head no. “Breed me.”

He thrusting picked up pace even more, both hands going back to my hips to help jam his naked cock into me. I started jerking myself off and after only about 15-20 seconds, I felt the most amazing orgasm come over me, and I shot a huge load under his table and all over his hardwood floor.
“I’m cumming,” he moaned as he switched to quick, short thrusts in and out of my ass, finally bottoming out as his raw cock finally stopped pumping its load in me. He put his head on my shoulder for a few moments.

“Look between your legs,” he told me as he started pulling out his cock. I felt the tip of his bare monster cock leave my hole and a few moments later a stream of his white cum leaked out of my ass forming a puddle on the floor.
“Holy fuck,” I said. “I actually didn’t think you were going to fuck me bareback.”
“That’s okay, right?” He asked, concern in his voice.
“That’s the best!” I exclaimed.
He went to get a towel and wiped off his dick and my ass and cleaned the cum off the floor. We cuddled naked on the couch and finished our wine.