This might be hard to explain, but... I had a fuck bud about a year or so ago. Incredibly handsome and masculine, with a ripped body (former marine), very high sex drive, and the first time he dropped his pants my jaw hit the table and I started shaking a bit, both from excitement and fear. He strapped a cock ring on and warned me that I was in for a long session. I started off blowing him to get him fully erect, more than anything out of a sense of adventure - I wanted to see how big the damn thing was going to get. Filled my mouth so much that I couldn't move my tongue. It was almost comical. Terrifying, but comical. I was like, I don't know what what I'm going to be able to do with this.
When he was fully hard his cock was - and I am not exaggerating in the slightest - 10.5 inches long and as thick as my wrist. Mind you I have thin wrists for a guy my build but whatever. We're talking wrist.
It took a lot of work to get that piece of meat inside me. I may have been freaked out at first, but this was bar none one of the hottest guys I'd ever been in bed with and the biggest cock I'd ever seen. There was no way I was not going to let myself get thoroughly, completely fucked.
He was patient, really patient - I think that's what makes a great top at the end of the day, reading the signs and taking your time so that your bottom becomes the one who claws at your back begging you to dick them within an inch of their life. He went with gradual penetration, massaging my shoulders and back while he snaked his way into me, talking dirty and telling me I'm about to be fucked better than I ever have before.
When he finally bottomed out in me... I was on a couch on my back facing out, and he was kneeling on the floor between my legs (which were just kind of dangling in the air around his shoulders) we both sighed. I never felt so full of cock, and his gradual entry made the feeling incredible. No pain, just fullness, warmth, it was amazing.
Then he started to fuck me. Holy shit did this guy know how to fuck. Steady rhythm, alternating between short fast strokes and slow to-the-hilt deep dicking... I just remember my fingers clamped on his nipples like they were handlebars and moaning uncontrollably.
The first, well, orgasm, that I had was about 10-15 minutes into the fuck. I didn't actually come (even though my cock was hard as a rock). I just got hit with this uncontrollable pleasure sensation that was seeping out of my prostrate area and soon made my entire body feel warm and flushed. Based on descriptions I've read of female orgasm I could relate. It was a sustained rollercoaster of pleasure that lasted long enough that he had to stick his fingers in my mouth to keep the loud sounds coming out of my mouth from traveling too far. I was babbling like a moron, my limbs were useless, and I had never felt pleasure like that in my life. And all through it he just kept thrusting that mammoth cock into me and working my insides over.
He was clearly getting off on what he was doing to me big time. After he (finally) came and we took a breather he said, "What the fuck was THAT?!" And we both started laughing and I said I didn't know, but that he made me cum - and cum HARD and LONG - without me really coming.
So we geared up for round two and at that point I felt like I could take him on plus USC's entire starting line-up. I could not get fucked enough. I begged him to dick me harder than I ever would have had the guts to before that, and I told him I wanted him to fuck me all afternoon.
I had two "anal" orgasms in that session before I finally came (while he was fucking me the third time).
Greatest sexual experience of my entire life. So if you can find a toy that can do that - LET ME KNOW.