Roughest fuck

[Guest subbttmhole]

What's the roughest fuck you have ever taken as a bottom, or given as a top? Was it planned to be a rough scenario or unplanned? Did you enjoy it?

I can say that while I enjoy rough sex now, I did not enjoy my first rough experience and it was unplanned. I responded to an old AOL ad back in the early 90's when Ilived in California. I was 19 and the top was in his 50's. It was supposed to be just me going to give him a blow job. He was a bigger muscular guy, I remember he liked to smoke cigars while getting sucked. He eventually talked me into letting him fuck me and he said would be gentle. He eased his way into me, but once he was in my ass and I relaxed a little, the gentleness was over. HE fucked me for about 15 agonizing minutes, holding me down, hands behind my back, no matter how much I begged he said that he wasn't stopping until he was ready. He finally bred my ass and told me to get out. He did tear my hole up pretty good.

[Guest barehole4use]

19 hours ago, subbttmhole said:

He finally bred my ass and told me to get out. He did tear my hole up pretty good.

Thats the way i like to be fucked to rough & raw, verging on *Y(*YO*HOH but hey you did consent.

[Guest subbttmhole]

Exactly, I did consent to getting fucked, but got WAYYYYYY more than I bargained or was ready for!

[Guest barehole4use]

Sometimes pain can be pleasure, i bet you whack off thinking about it now.........R.A.P.E.

[Guest subbttmhole]

Oh fuck yeah! I have had a couple of *Y(*YO*HOH role play scenes and fucking loved every second of it, even the painful ones.

[Hard8Stud]

I cannot pick just one because of 3 very different times that were extraordinary:

In 2006, I met a guy through one of the better "dating" phone systems at his apartment. I arrived in shorts and waist-up natural, and he opened his door wearing only low-rise briefs before I starting climbing the stairs. I was not quite 51, he was 28; we both had good, lean physiques, and we both stripped completely as soon as the front door closed. I already knew we had a lot in common sexually; but, I soon discovered it was a lot more than I thought:  He not only enjoyed interracial sex and preferred 3-ways & groups and outdoor sex as much as I did; but, he had lots of high-quality porn showing all that on his big-screen TV in his bedroom.  We must have played for over 2 hours because, by the time we started fucking, we were both extremely horny. I had brought a quart of Gatorade, and he had the A/C on. I often fuck for half an hour nonstop have fucked many times 45 minutes nonstop; a few years later, I fucked a group-party host for 3 1/2 hours including three 10-to-15-minute breaks to cool off & rehydrate, ending only so I could get a little sleep before going to work.  But, this time, I plowed this hot, young power bottom hard and nonstop for a full fucking hour. After no more than 40 minutes, the sheets on his double bed were soaking wet from our sweat; but we kept going.  After a solid, nonstop hour of fucking, I thought I was close to cumming but started getting overheated; so, he turned the A/C down some more, and I drank most of my Gatorade. That helped; but, I was too overheated and needed longer than either of us had for me to cool off and recover enough.  So, I had to leave without cumming, to the disappointment of both of us.  He contacted me again at least twice more; but, we weren't able to arrange a meeting again.

One man with a lean physique who looked almost ten years younger than he was was the best deep-throat cocksucker by far whom I have ever encountered.  He truly enjoyed the ecstasy he knew he caused by swallowing a big cock all at once; I have 8" (measured topside from pubic bone to tip) that's 2" thick (6" around), but he told me of nearly blowing the mind of a man with 10, thicker inches when he swallowed his cock whole like that.  Because he was such an eager deep-throater with no gag reflex, he also enjoyed rough skull-fucking, which he did several times.  Some guys enjoy it, but he made it super hot!  One of the last times we met, we got into the hottest 69 ever as we pressed our bodies tightly together, deep-throating each other while rolling around the floor well after sunrise and after having already played since sometime after midnight.

In March or April 2019, I met a now-40-year-old experienced bottom at a park one night for the 6th time. After taking in the entire situation, we knew we had no need to hold back while I fucked him on an outdoor picnic table; while we were fucking, another, younger guy got out of his car and circled around to watch from a distance. When he got close enough, we signaled him to come watch us up close; he not only did watch but started handling both of us, including feeling my cock as I fucked. After we'd fucked not quite 20 minutes, I made the bottom cum hand-free for the 5th time. As he got up, he gave one of the Magnums he had brought to the younger guy whom I could now tell was in very average shape but about 28 years old, probably partly hispanic, and very horny. He took the used Magnum off my cock, handled it to make it rock hard again, then put the 2nd one on my cock. I was soon fucking him hard & deep and like he'd never been fucked before!  The semi-regular I started with sat in his car and could often here the loud slap-slap-slap as I plowed that young man but good!  After half an hour of loud, hard, deep, outdoor fucking, I finally shot my load while deep inside him. Only then did the guy I started with drive away. As we got ready to leave, he wanted to know how often I visited the park because he wanted lots more!