Ok so the first time I was successful with this whole thing was a couple of weeks ago. I was going to this work event that was kinda far from my place and I wasn’t sure if we were heading to a happy hour after, so I decided to call an uber.
The uber driver that accepted my ride was probably around his late 40s, very good looking, a bit built, not muscular tho, almost like a bear kinda type. His name was Cliff. As soon as I entered the car, he greeted me very friendly. He asked me how my day was going so far, where I was going so well dressed, you know the regular nice guy stuff. As we were casually talking I noticed he was married, cause I saw a very noticeable ring.
I asked if he was working for a long time as an uber driver and he said it has been 5 years. This gave me the opportunity to ask more about him, like if he was in fact married (yes), had kids (2 boys and a girl), etc. As we were chatting about being an uber driver, I said: “you have probably seen some real weird shit”. I was hoping he would say something like being propositioned by some guy or girl, or something like that, but unfortunately no. He mentioned how he was involved in a car crash once, and how another passenger was really rude to him almost to the point of being physically aggressive.
After that I tried something I saw someone mention in another forum website. This guy said he ofter started some topics about men’s health and urology and how this lead him to some more saucy conversations (older guys seems to be interested in health topics). So I asked if he used to work for long hours driving without taking some time to rest. He mentioned how some days are so busy he cant even stop to pee. This gave the opportunity I wanted.
I remember I stumbled upon this article about prostate health, so I had some ideas in mind. I made up this story about a friend of mine who is an urologist and warned me about sitting for long periods of time, and how bad this is for men’s health, specially for the prostate (this was in fact written in the article). As I said this, he immediately went “Really? Because the other day I was reading something about this! How sitting still for hours can be bad for the prostate, and this left me wondering if that might be happening to me, because I have an history of prostate conditions in my family.”
Since he talked so openly about this, I continued the conversation. I told him my friend warned me about some symptoms I might find if that was becoming a problem for me, since I work at an office job and also sit still for hours. I went “My friend says you can check for a few things in your penis to see if this is affecting you”. He then asked what were those things and kept looking at my face like he was anxious to hear the answer. “Well you can simply check if you feel a burning sensation when you pee. You can also check if you frequently have random erections while you are sleeping. Another one is trying to see if your penis head often gets red or purple ish.” I knew most of these are pretty common so he would relate to this.
He stopped for a moment and then asked: “well… did any of these helped you? I mean did you notice any of these?” and again kept looking to wait for an answer. I said: “well all of them!” then I laughed. “at first I got worried about the color of my penis head because sometimes it does get a bit red. But I wasn’t sure if that was a normal type of red.” He immediately said: “exactly! How the fuck am I supposed to know?” Then I said “yeah that was my concern too. Since this friend of mine is really close to me, we practically grew up together and he had seen me naked before, I asked if he could have a look to see if that redish type of color in my penis was normal or was in fact a problem. He had a look and said it wasnt a problem, to my relief”
As I said this, the driver nodded and stopped talking for a few seconds. Then he said “well this doesn’t help me” and laughed. Then I asked “is this happening to you? Does your penis often gets red?” He confirmed. Another brief moment of silence. Then I asked: “but wait, how much of a red are we talking about? Is it really really red?” He went: “sometimes yeah”. I couldn’t believe I was talking to my uber about our cocks! Lol
To keep it natural I said “I think you should probably seek an urologist just to make sure”.
He agreed and said: “yeah absolutely! I mean, us men we hate going to the doctor but at my age there’s no way out”
Then we started talking how the male culture makes us feel uncomfortable about doctors and talking to other men about intimacy and other related stuff, and how much of a bullshit that was. I even said: “look, we dont even know each other and we are talking about our cocks LOL this isn’t so hard, is it?” He laughed out loud it was funny. Then to break the ice I asked: “and what about the burning sensation when you pee, do you feel it?” And he went “almost every time, but that is pretty common I think. What is bothering me is the red penis thing” and uncomfortably laughed again.
After a brief moment of silence, courage struck me and I asked very casually: “well, we are both men here, do you want me to have a look?” He stood silent again for like 5 seconds and looked straight at me. Then again to break the ice I said “if that doesn’t make you feel uncomfortable, of course. I just want to help”. After another moment of silence, to my surprise he said “well fuck it” and started unzipping his pants. I think my face went red like instantly. I could not believe that was happening! lol
He pulled his penis out and looked at me. I obviously had a VERY GOOD look and asked him to turn it to the side a bit. His cock wasnt even that red. He was uncut and average I would say. it had a normal tone of red. Id say that was a nice cock. That moment is going to be engraved in my mind forever lol. Then after almost like 20 seconds looking at it I said: “I think you have nothing to worry about, dude really. To be fair, the color is almost like mine, look...” Then I did like I was going to unzip my pants too. He immediately, like IMMEDIATELY looked at my hands. I quickly unzipped and pulled my cock out, to give him almost no time to think. It was funny cause of course I was a little bit aroused, I almost had a semi. He also took a really good look at me dick lol.
Again to make it look less uncomfortable after like 10 seconds I quickly put my dick back and said “don’t worry, if Im clear you are too LOL” and we both laughed. I remember I kept talking very calmly and casually to make it seem like nothing had happened. Then I said: “im sure you are a very healthy dude, but hey just check with a doctor, just to be safe, right?” He agreed. He looked very relieved to be honest.
The rest of the ride was really nice, we kept talking about so many random stuff, He was a really nice guy. As I was leaving the car once we got to my destination, I remember I said: “stay healthy Cliff, go talk to a doctor just to be safe ok?” And he went: “I will, you too! And sorry if I made you feel uncomfortable”. I said “not at all! We gotta take care of each other man!” And I left.
to this day I can’t believe I pulled that off. I jerk off to his cock sometimes I gotta admit lol