This remembrance piece contains explicit descriptions of gay sex. If you're below legal age to read adult stories, or are uncomfortable with gay themes oar explicit gay sex, stop reading now and close this file.
Only a few minor details have been changed. The main characters are on PrEP and their sex is raw. Please respect yourself and others enough to always play safe -- use condoms or get on PrEP and Doxy-PrEP. Get tested regularly and please get vaccinated for mPox, hepatitis, and COVID. Help keep our community healthy.
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Years long foreplay
I have been friends with Mark since the mid-80s. We got naked and jerked off a few times together early in our friendship. But, this was in the age of AIDS so we never sucked or fucked. As time went on, we didn't even jerk off with each other very often, but there was a lot of sexual innuendo thrown around. If I had thought it was safe to fuck, I would have asked him repeatedly to take my cock.
A few years later, my partner (now husband) and I moved from New England to Chicago. Mark and I only saw each other sporadically for the next two decades.
A few years ago, Mark came to Chicago to see my husband and me. He made the trip to help a friend move but arrived a couple of days early for a visit! We did some touristy stuff. While working around Millennium Park downtown, I told him about my experiences with a group of bears that had regular naked sex parties and how much I enjoyed topping men there. Mark said he was jealous as he had not been fucked in months. I told him I'd be happy to end his drought. I think Mark was a bit taken aback since we had not been sexual with each other for a couple of decades except with verbal teasing. He smiled and then, somewhat conspiratorially, said he was interested. I told him my cock just chubbed up at the thought of plowing his hot ass.
Later that afternoon from the bathroom, I texted him a couple of pics of me Ð one of my fully erect and thick cock and one of me fucking a buddy. When I returned, Mark looked up from his phone with a big smile. Later that afternoon, he declared, "I want that fat cock in my ass. No, I need it in my ass." I grabbed his ass, saying, "My cock needs to be inside you."
I always stayed up later than my husband so I told Mark to come downstairs to the TV room after 10. My husband and I are open but we rarely play together with others. I wanted Mark's ass to myself.
Mark appeared in the TV room, wearing workout shorts (commando) and a t-shirt. I was dressed the same. I had pulled out a bottle of lube and a couple of towels and put on my cock ring before he arrived. We started kissing and then quickly undressed each other. I could not wait to get him naked. I licked his neck and then started sucking on his nips. His cock got quite hard without either of us touching it. My cock was already hard from kissing him. Mark was an excellent kisser. I loved pulling his sexy body against mine and feeling my chest hairs pressing onto his chest. I grabbed his ass to pull him closer and our hard cocks rubbed against each other. So hot!
We then sucked each other's cocks a bit. But then I wanted to move on to the "main event." I asked if he was ready for my cock to fill his ass. I had already shared I was on PrEP. So was Mark and he begged me to fuck him raw. He didn't have to beg. That's what I wanted too!
I had him kneel on the coffee table on top of a towel. I lubed up my fingers and began to explore his asshole. It opened up easily and within about 30 seconds I had three fingers in. Quite impressive for a guy who had not been fucked in weeks! Mark told me he needed me to fuck him Ð hard! I lubed up my thick cock and slid it in. With most men, I need to enter slowly until they get used to my girth (slightly bigger around than an empty roll of toilet paper). Mark's hole was a little tight, but the resistance to my mushroom head was minimal. Within a couple of gentle thrusts, my pubes were nestled against his ass. I reached around and stoked his dripping cock. I wiped off some of the precum, then rubbed it on my cock as I pulled back for some extra lube Ð mostly because it was hot to fuck Mark with his precum. I paused for about 30 seconds for his ass to start getting used to having my cock inside. But Mark had other ideas. He wanted me to pound him, hard and fast and deep. Who was I to say no to that request?
Mark began moaning loudly as I fucked him. He wanted it hard so I pounded even harder into him. I thrust quickly and was balls deep with every thrust. I also spanked his ass a few times as I fucked him. He grunted and moaned as I discovered the right angle to hit his prostate. I loved fucking him. Mark was so responsive to my fucking and pushed back to get every inch. He kept saying, "I love how thick you are." It may have been flattery, but I liked hearing it. I reached around and stroked his dick and tweaked his nipples as I fucked him. I bent over, pulled his head up and to the side and kissed him. I felt his cock throb in my hand as we kissed. Then, I put both hands on his hips and fucked him as hard and deep as I could. Mark made some indecipherable guttural sounds and pressed his ass towards me for more!
Finally, I was getting close and told Mark. He started stroking his rock-hard cock. He gasped and moaned as he erupted with a big volley of cum right before I shot my loads deep in his ass, grunting quite loudly. As he came, his asshole contracted tightly. That tightness was what caused me to shoot. I was not complaining. That orgasm was so intense. I probably had six or seven blasts of cum. I stayed inside Mark as long as I could until my hard cock eased. But then, I pulled out, accompanied by a satisfying "pop" sound as my mushroom head emerged. Mark laughed at the noise, then turned around and licked my cock clean. When done, he climbed off the coffee table, stood up, and hugged me tightly. We kissed for several minutes. I wiped his ass off and offered a shower. Mark replied he wanted to smell me in bed and headed upstairs. He paused at the second step and said, "I do have one regret, Daddy. I regret we waited so long to do this. That was so fucking hot. I haven't cum that hard since I don't know when. I need that cock in my ass, again and again..."
I can't wait until we fuck Ð again!