Gregshaw
Oct 18, 2022, 3:45 PM
Back when I was single I had my first experience with another guy. As a kid I'd had the usual curiosity driven urges to compare my cock to other boys & once dared a quick touch but I didn't really know what I was doing. Only age 19 did I follow through with a raging inner sex drive that no amount of pussy could satisfy & I got fucked by a contractor guy I worked with for a while.
But after that brief spell everything went quiet & I went back to girls exclusively (although i did occasionally give guys oral I had no more ass sex) until I turned 40 & the urge for cock started to drive me crazy again.
Craigslist Personals was still a thing so I posted an ad & tried to filter out the bots & fakes until one message arrived that actually seemed genuine. He was a bit younger than me, but looked handsome, toned body & was local. We exchanged emails & eventually I plucked up the courage to get cleaned up & head out.
His place was a dinky rambler 5 miles across town, he was fixing it up to sell so it was messy inside, but the bedroom was tidy. We sat on the sofa & chatted, I realized that I was a bunch of nerves so I gladly accepted a cold beer, the act of moving around meaning we went from "guy to guy" distance on the couch to something closer.
He was friendly, easy going & open about being married, kids & divorced (who knows if it was true). I explained my situation & he listened, assuring me that he'd treat me like a virgin since it'd been so long. As he spoke he leaned a little closer & soon his fingertips brushed against my leg. I smiled....he smiled....then he moved in closer, rising up on his knees so his hips were head height to me I looked up & then my hands slid up the bulge in his pants into the belt buckle & I undid it, unzipped him & yanked his pants down.
He was indeed toned, his flat stomach & muscular legs were now there for me to see & as he tossed away his shirt the rest of him was the same. His cock was about the same as mine in.length & thickness with a bright red head that radiated heat. I slid my hands over his butt & felt the clenched muscles there.
He was already stiff & a little dark spot at the tip showed he was already leaking pre cum. I wasted no time & tugged his briefs down & he wasted no time in thrusting forwards so I once again had a cock in my mouth. His groans assured me that I'd not forgotten how to do it right.
Soon he was pulling my clothes off & he whispered "I want to see that ass." I work out at the gym & he made it clear that he thought it looked just as good as the pic I'd sent, then he groped & massaged it all the time he kept going "Oh yeah!" He rubbed closer & closer to my hole & then diddled my tight ring before kissing, then slipping a tongue inside me. It was electric & I'd never had it done before. I could feel myself opening up & relaxing to let his tongue in & he said "You seem ready." I told him that I was & we went off to the bedroom.
Lying face down he continued on my ass, lubed fingers were next, first one, then two, then I don't know how many, while I grabbed pillows & put them under my hips. His fingers stopped & I heard the rip of a condom packet & a gloop of lube, then the unmistakable feeling of him moving in place to be over me.
This was it, the moment of trepidation. It'd been 20 years since a man had penetrated me & I was quivering. I tried to relax as the tip of his cock touched me but he was cool about it & teased me, swirling his hard cock around my sphincter until I was relaxed again and then the initial push into me. I groaned, it didn't hurt & he took it slowly but bit by bit he worked himself all the way in until he rested flat on top of me & he whispered in my ear "Oh fuck you are SO tight!"
His thrusts were barely nothing at first but he built it up slowly. Eventually he was bucking & thudding against me. I managed a few glances over my shoulder to see his shaft sliding in & out & how my butt cheeks shook as his groin came slamming down, but the growing ball of pure ecstacy that was deep inside my belly was beginning to radiate outward & soon it took away my entire ability to function.
20 years after my first fucking I was in absolute heaven & even unaware that he'd cum & was now a sweaty panting heap pressing down on me & moaning "Oh God! OH god!"
After a while we'd both recovered enough & he slid out, his beautiful cock hanging down, limp but still engorged. Later he sucked me off with 2 fingers slipped inside.
We had regular weekly fuck sessions for a while but he sold the house & moved to Arizona. He'd got back with his wife & kids so although we tried to hook up it was difficult & awkward for him so we drifted apart.
I was no longer a virgin for the second time & was determined never to let it happen ever again.
But after that brief spell everything went quiet & I went back to girls exclusively (although i did occasionally give guys oral I had no more ass sex) until I turned 40 & the urge for cock started to drive me crazy again.
Craigslist Personals was still a thing so I posted an ad & tried to filter out the bots & fakes until one message arrived that actually seemed genuine. He was a bit younger than me, but looked handsome, toned body & was local. We exchanged emails & eventually I plucked up the courage to get cleaned up & head out.
His place was a dinky rambler 5 miles across town, he was fixing it up to sell so it was messy inside, but the bedroom was tidy. We sat on the sofa & chatted, I realized that I was a bunch of nerves so I gladly accepted a cold beer, the act of moving around meaning we went from "guy to guy" distance on the couch to something closer.
He was friendly, easy going & open about being married, kids & divorced (who knows if it was true). I explained my situation & he listened, assuring me that he'd treat me like a virgin since it'd been so long. As he spoke he leaned a little closer & soon his fingertips brushed against my leg. I smiled....he smiled....then he moved in closer, rising up on his knees so his hips were head height to me I looked up & then my hands slid up the bulge in his pants into the belt buckle & I undid it, unzipped him & yanked his pants down.
He was indeed toned, his flat stomach & muscular legs were now there for me to see & as he tossed away his shirt the rest of him was the same. His cock was about the same as mine in.length & thickness with a bright red head that radiated heat. I slid my hands over his butt & felt the clenched muscles there.
He was already stiff & a little dark spot at the tip showed he was already leaking pre cum. I wasted no time & tugged his briefs down & he wasted no time in thrusting forwards so I once again had a cock in my mouth. His groans assured me that I'd not forgotten how to do it right.
Soon he was pulling my clothes off & he whispered "I want to see that ass." I work out at the gym & he made it clear that he thought it looked just as good as the pic I'd sent, then he groped & massaged it all the time he kept going "Oh yeah!" He rubbed closer & closer to my hole & then diddled my tight ring before kissing, then slipping a tongue inside me. It was electric & I'd never had it done before. I could feel myself opening up & relaxing to let his tongue in & he said "You seem ready." I told him that I was & we went off to the bedroom.
Lying face down he continued on my ass, lubed fingers were next, first one, then two, then I don't know how many, while I grabbed pillows & put them under my hips. His fingers stopped & I heard the rip of a condom packet & a gloop of lube, then the unmistakable feeling of him moving in place to be over me.
This was it, the moment of trepidation. It'd been 20 years since a man had penetrated me & I was quivering. I tried to relax as the tip of his cock touched me but he was cool about it & teased me, swirling his hard cock around my sphincter until I was relaxed again and then the initial push into me. I groaned, it didn't hurt & he took it slowly but bit by bit he worked himself all the way in until he rested flat on top of me & he whispered in my ear "Oh fuck you are SO tight!"
His thrusts were barely nothing at first but he built it up slowly. Eventually he was bucking & thudding against me. I managed a few glances over my shoulder to see his shaft sliding in & out & how my butt cheeks shook as his groin came slamming down, but the growing ball of pure ecstacy that was deep inside my belly was beginning to radiate outward & soon it took away my entire ability to function.
20 years after my first fucking I was in absolute heaven & even unaware that he'd cum & was now a sweaty panting heap pressing down on me & moaning "Oh God! OH god!"
After a while we'd both recovered enough & he slid out, his beautiful cock hanging down, limp but still engorged. Later he sucked me off with 2 fingers slipped inside.
We had regular weekly fuck sessions for a while but he sold the house & moved to Arizona. He'd got back with his wife & kids so although we tried to hook up it was difficult & awkward for him so we drifted apart.
I was no longer a virgin for the second time & was determined never to let it happen ever again.