Risy Business at a Hotel

It was one of those lonely Saturday nights. Swiping through all the possible matches on a dating app. There was nothing interesting on the tube.

As I was about to pour myself another drink of vodka when I remembered I've been daring myself to explore my bi-curious side. I excitedly opened the tinder app and turned on "everyone" to show me any men as well as women. At 38, I preferred older men, the younger crowd didn't catch my fancy at least not for my first time of being with a man.

I kept swiping for 10 minutes before realizing the odds of someone swiping back, having a conversation and then making plans to meet, were slim. Giving up, I prepared myself for some television re-runs.

I head my phone beep and almost didn't trust my ears. There was a match. A 55-year-old chubby, short, older man with a thick mustache. We chatted for a bit, and he let me know he was married and was here on business and was staying at a hotel close by. Asked me if I would like to meet for tea. He came across as a confident sure of himself kind of guy.

I was excited and nervous. Meeting women was what I was used to, that too at a Café. I had never met a man, let alone in his hotel room for tea. So many 'What if's' kept darting around in my brain. What was a harmless try on tinder had now become a reality, within half an hour I would be driving to the Hotel, which happened to be close by. What if someone saw me... what if... what if... what if.

It was now or never. I quickly threw something on and drove to the Hotel. Parked without the help of the valet, so I knew where my car would be in case I needed to make a quick getaway. Not making eye contact with the security at the door, I entered the hotel. There were people up and about in the Lounge chatting and having coffee. I took a deep breath and made a beeline for the loo, took a leak and asked myself if this is something I really wanted.

It has been years of pondering and wondering and imagining. It was time to take the plunge and be bold. I zipped up my pants, washed my hands and whipped out my phone to see if he had replied to the message I sent him before entering the loo. 'I'll be right down' is all that I read.

As I got out of the loo and looked around the lounge I saw him walk toward me, he looked like top management. Was decent. I just said Hi and he asked me if I wanted to go to his room, I followed him to the lift where he used his Card to get in and hit the floor. Small talk is easy for me to make especially while I'm nervous, we spoke about how easy it was for me to find the place. As we walked through the well lit carpeted hallway all I could think of is, if I wanted to leave, now would be the time. Something made me stay and follow this stranger to his room.

The room was nice and dimly lit, I sat on the sofa as he asked room service to bring up the tea. I have to be honest, I was kind of impressed by his composure, he was married, on a business trip, probably going to charge everything to his company. Yet, he didn't seem nervous, it did not seem like it was his first time, like he said it was. Confident. Stoic.

We chatted about what I do and what we're looking for, now, in those days, it was hard to admit to oneself that I was a bottom. It was something I was struggling with, being bi curious was ok, being bottom, somehow, had some stigma due to the macho way I was raised to be 'a man'. I let him know I am a top, and he said he was one too. He smiled and told me that is fine, and it was fun to meet, and we could just have some have tea and go our own way, a real mind reader he was, like he could sense what I wasn't thinking before I even said anything.

As I sipped on the tea, I calmed down, relaxed a bit as we kept chatting. I then told him I could try if he liked. He watched me undress and eyed my circumcised cock. He dimmed the lights a bit more and got into bed next to me.

Rubbing the hair on his chest felt nice. I felt comforted being in his arms. Running my hands over his chest and tummy. He was a big man, but there is a vibe you get when you are in physical proximity of someone who can overpower you easily, you feel helpless, a good kind of helpless. Submissive.

I ran my hands down his chest and kept going down till I found his already hard cock, it was nice and small, I liked it, uncircumcised. I stroked it for a bit before wondering if I wanted to suck on it or not. Not only that, but I played it cool and thought he would ask me if he wanted that. I kept stroking for a few more seconds before I apparently unleashed a dragon. He, in one swoop gesture, turned towards me and within a split second had spread my legs and was in between them.

It was exciting to see how excited he was. I was pinned and his big chubby body was nice. I kept running my hands over his chest. He thrust his hips forward, and I could feel his pre-cum lubricating my asshole. I didn't make eye contact with him and when I did, he realized I was about to say no, and he said, he just wanted to rub his cock against my asshole and was not going to put it in.

At that time in my life, I had never had penetrative sex, I didn't own a butt plug, I had not stretched myself out. I was simply not ready to have anal sex. Let alone unprotected anal sex. It was just a big no for me. Blowing a guy, sure, but sex was not on the cards.

He grunted as I rubbed my hands over his back and he kept jabbing his cock at my asshole, I could now feel pre-cum trickle down my asshole, and I was quite wet with it. His grunts got louder next to my ear. He then said, 'Can I put it in?'. I must admit, I knew I wouldn't and most likely couldn't but at that time, in the heat of the moment, I feel it would have been nice to get fucked by him.

I said no, he got off me, I went to the loo and washed off his cum from my asshole. Put on my clothes at the speed of light, felt like James Bond. I said I'm sorry I can't do this.

He pleaded that we could take it slow, I think, looking back now, just the fact that he was so well-read and still didn't think it's smart to use a rubber, scared me, a lot. It meant he wasn't in control. That probably was a red flag for me on some unconscious level.

Don't get me wrong, he was a nice chubby man, who was not getting sex at home, and it felt exhilarating that he was so excited to be with me. I hope in the future to have more exciting encounters like this one.