The first girl I contacted turned me away at her doorstep because I look like a 16 year old when I'm shaved and had to go back to the car when asked to show the documents. The next gal I messaged was an average hooker, okay ass but small pointy tits. Came to her apartment, showed her the driver's license that I expected I'd be asked to show, took a quick shower. When I left it I transferred her the money (~90$ for sex + bj w/o condom + finishing in the mouth), she asked me to take off the boxers and lay down, so I did.
Naturally since I just left the shower I was still flaccid, but in like 2 minutes tops after she gobbled it up I was already rock hard, cause holy shit it feels good to be inside of a mouth. The awkward thing was, the next 15-20 minutes she spent sucking on it really fast and we even had to resort to a really speedy handjob because I just couldn't cum, at all. I wasn't flaccid and I was genuinely enjoying it, but I just couldn't finish no matter how hard we tried. After many failed attempts I grew impatient so I just suggested I put it in already, so we got into a missionary position, she puts the condom on and I finally thrust it in.
The feeling of being inside is a bit hard to describe, but to me it felt like my dick was inside of a warm, soft, wet hose that was slightly strangulating it from all sides simultaneously. It's definetly a thing worth feeling at least once in your life, that's for sure. Anyway, as soon as I start thrusting myself in and pulling myself out I realise that having sex is much more physically intense that I imagined it'd be - nothing you can't handle but nonetheless it tires you out. 5-10 minutes passes of me banging her to the best of my abilities and I begin to notice that I'm slowly going flaccid. It's still hard enough to bang but I start slipping out of her. A few more minutes pass and I'm no longer hard enough to put it back in - I jerk it a little, try to put it back in but nothing works so I accept defeat, take a quick shower, bid my farewell to her and drive home with the boys.
Still not completely sure what happened back there - it kinda felt like she chaffed my head when she was blowing me so it stopped being as sensitive as it usually is, or maybe I just wasn't horny enough - but when I went to shower for the second, I didn't even feel any regret or sadness, my thoughts were more along the lines of "oh well, shit happens and it felt good regardless". I spent this evening feeling good, and me being unable to cum simply felt like a missed opportunity, rather than an outright failure that'd ruin the whole day.
tl;dr I got rock hard at one point but I couldn't finish. The whole ordeal can be described as "pleasurable" - it felt really good in the moment but overall it was nothing extraordinary (maybe that's because I wasn't drunk lolz).
