I know this thread is ancient but I love hearing about other guys’ experiences in this space. If anyone has more to share, please do!
I have two instances where I’d paid for sex (or a special massage) with women who had memorable reactions.
The first was in Thailand, and I was both very nervous and very excited — I’d never had full sex with a woman before. So she led me to the room, closed the door and nicely told me to undress. Shirt off first, then shoes/socks, then I unzipped and dropped my pants, and BAM there’s my little woody sticking straight out at full mast in my undies. She could not stifle a giggle but recovered nicely. Until she knelt down to pull down my undies and she had to cover her mouth to keep from laughing again... she looked up at me with a big grin, took my joystick between her thumb and forefinger and said “well at least it work!” And of course as if on cue, it twitched and bounced.
The next was in Buenos Aires, where I was walking back home at night and feeling very horny, so succumbed to the sloppy sales pitch of the guy out front of a... “massage” place? Sex shop? Still unclear. But I came in, had drinks with the two girls (women older than me), and negotiated a price for some further attention in the back room. One of them took my hand and said, looking at my rather large body, “Mmmm, I bet you have a BIG ONE,” and I laughed, holding up a pinky and said “oh no, I sure don’t!”
Despite the warning, both were absolutely shocked when, after we’d kissed for a while, they unzipped me and “pulled it out,” to laughter so hard the bouncer came back to get a look himself. Immediately, sex was off the table, but they rolled a much-too-large condom down my wee shaft anyway and let me kiss and suck on breasts while I jacked myself into the loose rubber. Money not exactly well spent.
And then there are the many reactions I’ve had when someone asks me to slide it through a gloryhole. Mostly just a snicker or a snort and then the sucker walking away. Sometimes a more degrading laugh or WTF is this reaction. Which is what I get on the rare occasion I’m at a gay club or bar and getting a little handsy with someone.