One of my biggest fantasies is to proposition a stranger on an elevator or on the street, not knowing if he likes men or is flirting with me, and end up having sex with him. Has this ever happened for you? Details.
Have you ever propositioned a stranger on the street and then tricked?
- Thread starter Capitolhillguy
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Yeah, it has been a thing for me, mostly years ago. At a time when it was risky to be known as gay and a crime to be in gay bars there were areas where "trade" hung out, looking for tricks. DC had several spots in public and a few bars where you learned the trade hung out. Baltimore was rife with it in a number of lower economic areas and near bars that were gay friendly.
Earlier than that - before gay bars and cruse areas there were notorious restrooms - usually in department stores there the legendary toe tapping preceded grindr by about 40 years. Same idea, just more primitive.
With #metoo and feminists on the war path trying to control everyone's sexuality. I'd be very careful about propositioning strangers, even if the guy (or girl) reciprocates it only takes one busy body bystander to spin the scenario into harassment or attempted sexual assault etc... and make allegations or claim they're being exposed to harassing behaviour, even when the proposition isn't toward them.
I must admit that is what held me back.
You're not alone. A lot of people are apprehensive about approaching people, even for a chat now.
halcyondays
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Never. Somehow I've always been the one approached. 
I have asked strangers out and we ended up in bed in short order but I've never asked one explicitly for sex.
I have asked strangers out and we ended up in bed in short order but I've never asked one explicitly for sex.
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When cruising for sex was young and so was I, most consent and interest and passing over were non verbal. I've had sex with more men I never said a word to..thousands maybe? There is a look that either tells you to drop to your knees or that you've found an eager, respectful and focused cocksucker. It's a hot look because sometimes you don't know which way you will fold. I had a stint with "lets try this bizarre pick up idea for shits and giggles" and then things went screwy because guys decided cruising was about rating and judging and being a raging bitch on wheels if you didn't get your penis of choice...then internet, then...
I find those guys who rate, judge and compete are fixated with 'types' are mostly socially inept and have difficulty with relationships.
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It's the logical outcome of a superficial commercial gay culture. Those invested in archetype and myth get hung up on the artificial rules that define these typologies and use them to try and make sense of their friends is toio be is pedantic and miss the point
I have had 3 different occasions when on the streets of NYC I was approached. One guy grabbed my hand and said where’s you apartment, once I was sitting on the steps waiting for a friend and a guy came up to me and said where can we go to fool around and the last time a guy followed me into a store and grabbed my ass and wanted to go into a bathroom near by.
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I was out of town and went to an adult bookstore. When leaving, I saw a hot guy headed in. I asked him if he wanted a blowjob. He said no, and looked a little startled. I think he was totally straight.
In one of the more well-known (and famously slutty) gay resort towns in a country in southern Europe, I had just escorted a trick to the exit of the building I'd rented an apartment in at about 6 AM when a guy who said he recognized me from the beach passed by. I took him up to the apartment and did him, too.
One guy stopped me in the streets, while walking home from work, in his van and asked me if I fancied giving him a blowjob. I declined in shock but then again, it was such a long time ago before I accepted the hoe inside of me lol
