Guys of Reddit, what is the strangest thing you’ve put your dick in?

Not sure if this story fits in this question, but this triggered a fairly recent memory that fits somewhat. A couple years back, a 21-year-old new client of mine was someone I recognized from being a waitress at my local dive bar, and on her first appointment I brought this up (that I recognized her) and she immediately was being very flirty and almost aggressively giving me "the signals." I can say she was instantly into me for sure because I am very average-looking older-ish man (super, super rarely hit on by strangers) and this woman was the type that would never, ever give me the time of day when I was her age. When she asked me for a drink, I said yes but honestly thought it was a prank of some sort. We went out a few times before she told me she had a specific sexual fetish that involved our age differences, my graying hair, my professional look, etc. and also said I looked like someone very specific in her life she wanted to fantasize about/roleplay with and that I seemed like a safe and discreet person to try this out with. I am very tame and not adventurous at all, and had a few different conversations with her to make sure I was not taking advantage of her or anything, and I was also single and lonely so thus led to the most strange and satisfying and certainly intense sexual relationship of my life, which lasted about six weeks in total. Based on her sexual roleplaying (which I only told my friend about) he said that she was probably insane, but I honestly think she was just a normal person who wanted to try something specific out, both enjoyed it, and then we went our separate ways, but I don't go to that bar anymore because I have a weird feeling it may be awkward, but anyway seems like she's doing well. Nothing like this has ever happened to me before and will never again, so I just look back at it fondly really. And obviously it was the best sex of my life.

/r/AskReddit Thread Parent