Three’s Company

My first threesome. I remember the events leading up to it well, even though it was more than two decades ago! I was about to start my freshman year in college, and was living with a relative while I got to know the local gay community. I made a lot of friends, including an older…

Bottoms Up!

A gay man’s first time bottoming is usually a memorable experience. Sometimes it is a good memory, sometimes it is a bad one, and sometimes that memory is if, well, a very awkward experience! Now, can you guess which category my first experience falls under? Back in my college days, my friends and I would…

This slut takes a tumble…

Orgies are, by nature, awkward. Awkward, but really fucking hot! I had seen many of them in pornos, but had never experienced one in reality. So one year, on New Year’s Eve, as I was stumbling around in the dark of my favorite naughty woods, I was ecstatic to come across an orgy!  There were…

Pop-what?

When I was 19, I lived in a small town with no organized or visible gay community, so I had few gay friends around me.  Sexual encounters were a very rare thing in my life at that time. There was a local adult bookstore that I had been to several times before, and enjoyed going…

No scrubs (in the closet)

I recently tried hooking up with a guy I met on an app (Scruff, for the curious). We had been chatting for over a month, and I was horny with a bit of free time on my hands one night, so went for it!  He was a hot young Cuban dude, and spoke very limited…

Chase

Since yesterday’s SINday post would have been in Xmas, I decided to postpone it by a day. Here’s this week’s SINday awkward sexiness! Use the comments to let me know how you’re liking the blog! One night, I was walking in my favorite naughty woods looking for some action. It was a slow night but…

SINday Tradition

Happy SINday everybody! Just a note before my next adventure post. Going forward, look for an adventure post weekly to celebrate each SINday! Please follow me to be sure you never miss the fun, and share with all your friends!

Crackhead

One time, when my partner was out for a weekend foray with friends, I decided to visit a nearby adult bookstore. I knew they had a video arcade area, and thought it would be fun to get some glory hole action. I hadn’t done this at a bookstore for over 20 years, so thought what…

Oh, it’s you!

One night, while sitting around a campfire at a private resort, I was thrilled to be talking with a very handsome young man. I had noticed him the previous day, and was quite smitten. We sat and talked for quite some time and, to my joy, he propped his feet on my legs. Have I…

Shall we?

Let’s have an adventure, shall we? Step into my world. There will be humor, there will be sex. There will be loads of akwardness! Stay tuned…