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Curiosity Prevails

My 15 year monogamous relationship was coming to an end (at least until the end I thought it had been monogamous.). I felt like time was running out and if I wanted to have fun and get back in the game the time was now. No more bars which I had always enjoyed for meeting guys. For some reason everything had switched to online. I guess it did make everything more convenient being able to meet a guy with the flick of a few buttons. I did not have a circle of gay friends to help me meet people. Also what could be easier whenever I felt the urge or need to get myself some relief or fun I simply clicked on Grindr or Scruff and within twenty minutes you could be in a sweaty mess with someone.

I had heard people talk of the apps but had never been on them myself. I did a quick study and finally came up with a profile, I wish I had not deleted my profile or I would post it. I will post some of my pictures of myself that I used, I felt like I was learning a new language, don't laugh, top, bottom, pnp, daddy, bear, twink etc all pretty new to me. I mean who knew there were so many different categories within the same community. I actually used the urban dictionary to look up some of the terms.

Mike after ending 15 year gay relationship

I was already missing the bars where you could be attracted to someone's smile, their eyes and flirt a bit. Not that I had that many one night stands in the past but I never had thought much about if I was going home with a top or a bottom, everything would just sort of work itself out. I mean there was nothing more exhilarating than a glance or a smile when your eyes meet another across the room and your heart starts pounding out of your chest and for some reason in that moment you both know you want each other without even having to say a word.

Picture of Mike asking are you top or bottom?

Well first things first I was middle aged and I was determined to be a bottom

for once and see if I enjoyed it. They say the male g spot is in the ass, so it would be stupid not to find out what it is like. After all it must be there for a reason. I had never tried it and wanted to. Many many years ago someone did try and top me and I practically flew out the window, I am not crazy about labels, but after that i guess i considered myself a top.

Mike playing in a sling 30 years ago.

I noticed everyone was pretty specific on the sites so I decided I would put that I was a bottom and put an end to the curiosity I had. The replies started coming but there was a steep learning process involved. It took me a while to figure out who was serious and who wasn't, who just wanted to have some sort of weird texting relationship, who was being honest and if I could really trust the persons pictures. I still don't understand why so many people on there use fake pictures and where does it get them, It actually took me about a year of being on grindr and scruff before I could figure out all the ins and outs of the sites. Eventually, I learned that I could usually tell in the first two minutes if I was interested and if it was going to be a go.

I remember I was out for drinks one night with some friends when I got a message from someone on scruff. We texted for a minute or two and it seemed we both wanted the same thing, I explained that I wanted to bottom and he was up for it. He was a top. Perfect. When he came over, I was surprised he looked so much better than his pictures. I was curious why he used such mediocre photos. He told me he would rather have people surprised than disappointed. Makes sense.

The fun was about to begin. At least I thought it was. We spent a little time messing around. It was time for the big moment. He tried and tried while I tried my hardest not to yell and crawl away. I don’t know who gave up first. We talked a bit, he was a nice guy and he told me to buy a dildo and practice and we could try again sometime. I was kind of disappointed all my hard work for nothing.

The next day first thing in the morning I went running to the sex store in the west village. I thought it would most likely be empty and I could get some help. I really hadn’t done serious shopping in a sex store before and was a little nervous about it.

I was right the store was empty. I went straight to the counter and told the guy I was looking for a dildo. He asked if I had any preferences. What brand and how big I wanted it. Fuck me I thought to myself. I'm a bit of an excitable person but very calmly told him my predicament.

I explained I was trying to bottom and the guy told me I was too tight and needed to practice. The shop assistant wanted to know how big my friend was. I said I had no idea I knew it wasn’t small. He then asked if he was bigger than me. I told him no. He wanted to know then how big I was. I have always hated that question and told him the truth. The same thing I say to everyone. I have never measured. I also told him I never had any complaints. The shop assistant then told me I must be at least 8. How thick was I. I showed him by pretending to hold my hand around my dick. . He said I was thick.

Next he started showing me a variety of dildos explaining the pros and cons of each. It was a pretty funny experience just seeing a long line of dildos all lined up the different shapes and sizes. I felt like Cinderella trying on the glass slipper to see which one would fit perfectly. We decided I should get one with a stand. I suppose so I could practice sitting on it. Material was one of those rubbery ones. Of course I went for a big one after always hearing “bigger is better, “. no, no he said I was going way to big. He said I should start out with a 6 inches. He told me I did not want to get too stretched out. He was right about one thing even that six inches felt huge at first.

One thing out of the way. Next I decided to look at cock rings. I didn’t really know anything about them except everyone seemed to have one but me and I thought they were supposed to keep you harder for longer. The guy recommended one and he was nice enough to let me try it on. In the dressing room I was really in a quandary. I could get my dick through it but not my balls. I’m still the only one in the store so I yell out to him my problem. He tells me to put my balls through first. I don’t know if it was the pressure I was feeling but I was having no luck getting my balls through first and then my dick. It was like some complicated puzzle at first. This time I opened the curtain and instead of yelling to him I asked him to come over and told him my problem. Being the helpful shop assistant he was with a naughty smile on his face he took the cock ring and my dick and did it for me. Eureka. I think he might have kept his hand on my dick a little bit too long but hey I wasn't complaining. Finally I now felt prepared for anything.

Picture of cock rings and dildos.
Shopping Delights

I went home, showered, put on my cock ring and started to play with my new toy. If I do say so, what a great toy it was and it's definitely safe to say and I think my ass would agree that I am gay. After a few days of practice and feeling my way around from the bottom up I was ready and called my friend. When he came over the first thing he wanted to know was whether I had done my homework. Like the good student I was, I thought it would be best to show a demonstration. He was impressed with how hard I worked, and we ended up having hours of fun and opened me up (pardon the pun) to a whole world of new experiences. I think I was lucky I found such a good guy to show me the ropes and broaden my horizons after all that's what makes sex so exciting and fun. Finding all these different turn ons and pleasures that make every inch of your body euphoric. So after experiencing both sides of the coin I think i’ll call myself versatile.

Picture of Mike asking do you want to flip?


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