Quite a few summers ago, when living in London, I (mid-20s at the time) matched on Bumble BFF with a straight student (early 20s) who was studying at Cambridge University. He had been in London for the day, but by the time we started chatting he was on the late-night one-hour train back to Cambridge.

As we were talking it became clear he was a bit bicurious, so I steered the conversation to be more sexual, complimenting his looks, asking him what he was curious about, telling him what I wanted to do to him. I could tell he was getting really into it.

As he was approaching his stop, he said “you’ve got to stop being sexual as I am super hard and can’t hide it in these shorts.” 

“Send me a picture.” When one pinged through, it was clear that he was going to have trouble hiding his nice-looking seven-inch outline with what appeared to be the beginnings of a wet spot.

Naturally, far from backing off, I went into overdrive, complimenting his cock, saying how sexy how was.

“Does it turn you on that people might see that, or you’re embarrassed?”

“I don’t know man, a bit of both.”

He gets to the station, hustles to the taxi rank, and jumps in a taxi back to his college. I decide to see how far I can push this, as he seems to be riding the wave between anxiety and excitement. I had some experience in the erotic hypnosis community and start to guide him to where I want him to be.

“Are you still hard?”

“Yes man.”

“Still leaking?”

“Yes.” 

“Are you enjoying this feeling?”

“Yes.”

“Do you want me to get you more horny?”

“Yeah.”

“See if you can get a bit more flow going by squeezing the muscles that contract when you orgasm. Imagine the precum starting to flow out with each squeeze. Squeeze about once per second.”

“Ha ok.”

“Just keep doing that. Feels good doesn’t it?”

“Ha yes it does.”

“Can you feel more precum oozing out?” 

“Yeah, I just got a huge drip.”

“Good boy! That’s great!” He tells me the wet spot is getting bigger. 

“Are you enjoying pleasing me?”

“Yes, it feels good.”

“How horny are you right now?" 

“Extremely.” 

“Out of ten?” 

“Ten for sure”

“Do you want to cum?”

“Yes.”

“Out of ten?”

“Totally a ten”

“How much further do you have in the taxi?”

“Maybe five minutes.”

I then encourage him to start squeezing faster, more like the speed of when he is orgasming and to keep his breaths shallow. He says he is feeling close to an orgasm. Imagine how good it will feel to just let it all flow out, I say, just keep squeezing. I can tell he is super close. The messages are coming thick and fast, and I am repeating the encouragements over and over, like a mantra, intoxicating him. 

“Feels good to please me doesn’t it?” to which he would always reply, “yes.” He tells me he is super close and feeling breathless.

He goes quiet for a moment, and then he texts to say he just came in his pants hands-free. That it’s a huge mess. That he let out a sigh when he did and the driver looked at him strangely in the mirror. He sends a pic, which is hard to make out in the dimmed light, but you can now see a huge puddle in his pants.

He comes down from his high pretty quickly and goes into more of a panic as the taxi drops him off at his college. He texts me five mins later saying he was back in his room and he had to run past people he knew to get there, his hands covering his shorts as best he could. I loved the visual of this.

“How was the orgasm?”

“Intense mate, never experienced anything like that.”

“And did you enjoy the humiliation of it?”

‘Hmmmm not sure, maybe not, will sleep on it and get back to you.”

We slept on it. In the morning he had unmatched me. Maybe he will stick to women after all.

Getting used by my much younger hispanic building doorman (Part 1) TRUE STORY 

I (30 at the time) moved into a large apartment building when studying in an American city for business school. From early on I thought the 20-year-old guy on the front desk was super cute: Hispanic, twinkly eyes, nice smile, tattooed muscly arms, tight jeans that showed off an epic ass and nice-looking bulge. He had been the subject of a few jerk-off sessions, but I had always thought he was straight (my gaydar is rubbish.) 

This all began to change when I asked Carlos (not his real name) about whether a package had arrived for me. He went to the post room to check and came back with a small box, which was clearly insufficient for the toaster I had ordered. “Oh that’s not what I was expecting. Damn.”  

“What were you expecting?”

“Something bigger,” I said, intending only the single entendre.

“I would hate to disappoint you with a small package,” Carlos replied, keeping it straight faced enough to be professional, but somehow communicating with his eyes that the porn star line was not entirely unknowing. And in that held eye contact I thought, “OMG, I think is he flirting with me?”

I made a quick-enough gear change to reply, “I’m sure you wouldn’t” in way that acknowledged his double meaning and returned it with a stolen glance at his crotch bulge. Then we smiled at each other in what I took as an admission that I was gonna suck his cock, but nothing more happened that day, cause someone else was waiting to speak with him.

But from then on, I resolved to get his dick.

This proved harder than I had initially thought, and when I saw him the next time it was totally normal. Maybe he had second thoughts, or was worried about getting in trouble? I spent quite a while ordering everything I needed from Amazon (and more besides) as separate deliveries, so I had more daily reasons to interact. But I was finding it hard to move it on; I didn’t want to hit on someone in their workplace and make it awkward for them (or indeed me).

The breakthrough only came when I split with my BF and downloaded Grindr. I started chatting with a close-by muscled torso. He said he was a dom top with a big dick, and thought my face was cute, and that I was his type. He knew it was me, but I didn’t know at that stage it was him (his tatts were cropped out, and it was a really big building and a university town, so the distance thing didn’t reveal it was him). He sent me his dick pics, it was a 7.5 inch, thick banana cock, with a lovely loose foreskin. Totally delicious. 

The chatting on Grindr happened for quite a while. He said he didn’t share a face pic cause he was mostly straight. He asked for my nudes, but I don’t usually send them. But over the course of chatting with him, he convinced me to take some pics for him, increasingly revealing to the point of humiliatingly exposed. When I’d see him at the front desk he would keep it totally normal, and not let on. I thought he had lost interest, if he ever had any. 

But the chats on Grindr were extremely explicit, and we had talked through all the kinky things we wanted to do to each other. There was some discussion about whether I would do an ass-up anon scenario, but I wasn’t too keen (ironically, I said I had to go and let hookups in or they wouldn’t get past the front desk).

In the end I said I wanted to see his face and that I can promise I was discreet. He sent it as a big reveal, perhaps nervous at what I’d say when I realized it was him. But actually at first I didn’t recognize him as his hair was styled more trendy, less work like, and it was not a good likeness. But then I clocked it was him. I was both extremely turned on and a bit miffed I had sent a load of submissive nudes to someone I knew. But then I reflected how hot it was that he had directed me into positions to pose in, knowing it was me, and the power imbalance, and how he'd kept things so above board when we actually interacted, and it was a huge turn on.

Finally at last we could meet, and we did the next day he was at work. We ended up hooking up three times in one day, but this is getting a bit long, so I will save that for a Part 2 if any interest.