September 16, 2025
Tuesday
I wrestled with the idea of calling Jer, a friend that I have known for over twenty years now. Sometimes it is months even years that we go without communicating. There's no bad blood. It is just how life plays it for us.
He is pretty handy with fixing things. Boss and I know we can always call him to fix it, whatever it may be.
August 11, 2025
When Boss was in rehab, I called him to see if he would help me assemble a mobility device for Boss. He came by with no delay even though he is about an hour out from us.
We chatted. He shared that he is seeing a guy but they were taking things very slow for now.
We first met at a gay men's group when I first started discovering the gay community, support groups for newbies dealing with their identities and learning to be more comfortable with who I am.
He was kind enough to offer me rides home from our meetings and social gatherings.
We became friends and would share about what was going on in our lives. (This was a little before I met Boss.)
We both were attracted to each other but were hesitant to cross that line out of fear of making things awkward.
One evening he gingerly tipped toed around the possibility of us getting together. I remember being so giddy and thinking to myself, "I thought he'd never ask."
From then on we were the true meaning of friends with benefits. We had a unique chemistry. We were both versatile although more than not he would end up topping me. I was more than happy to oblige. Of all the guys I have been versatile with, he is one of the few that I would be more than content bottoming for. He just knew how to lay it down. As a matter of fact whenever we would get together I would automatically assume the position. There was just something about the size that fit perfect. Not so big that it was too much for me but still big enough to allow me to enjoy it thoroughly.
About a year after Jer in 2003, Boss came into the picture. As we were getting to know each other Boss became familiar with some of the people in my circle.
Time goes by. Things change, people change and we go our separate ways. Eventually the play time we used to have stopped as we got into our own relationships.
Fast forward to this year, I called him up to help out with assembling the device. He came up and helped out. We chatted about the new guy he is seeing.
He is pretty content with what he has even though they are taking things slow. His one complaint is that his new partner is not as versatile. Jer bottoms mostly all the time for him. His partner hardly ever bottoms for him. Though Jer doesn't make a fuss about it, I know he is an ass man. He shared with me that if he would just give it up more that he would be most content.
As we were putting working on the project we caught up on some of the play we have been getting into. We are pretty much the same with our views on hook ups. He is so much more content with his guy. But there is always that occasional meet up.
I found myself getting somewhat turned on by our conversation. It took a while for me to admit it. But, I figure it was now my turn to gingerly tip toe and make my confession. He smiled and reached to feel the bulge in my pants.
"Yep. Conversations like that will do it to you." He said with a smirk.
We finally finished up. Ready to bring the device up to the facility, made plans to load it in his truck.
Before we walked out the door I asked him to follow me down the hallway.
I stopped and reached out to feel the bulge in his pants.
"Do you mind?"
"No. Go right ahead." He replied.
I got on my knees and took it out of his shorts. I remember that he hardly ever wear underwear making it much accessible.
I began sucking it getting it semi hard. I didn't get it all the way hard; just enough to give him a taste of what he's been missing out all these years.
"We got to head up to the center so we don't miss Boss's physical therapy," I interrupted.
"Well, now look at what you done. Got me all hard. Hope I don't start leaking," he said.
"Well that's what you get for not wearing underwear!" I laughed.
That is as far as it went.
September 16, 2025
I gave Jer a call. I had that day in my mind.
I shared with him that I was very much interested in getting together with him some time if he was up for it. I just wanted to make sure that it wouldn't interfere with what he has going on with his new interest.
He shared that one of the reasons why he never felt inclined to hit me up was because he had much respect for Boss and didn't want it to be weird for any of us. The ironic thing is that Boss asked me in the past and recently if we ever fucked around. Actually if we ever dated steady. I was honest with him and told him we didn't date. It was more of a sexual thing. Boss actually mentioned that he really likes Jer and if there was anyone he felt most comfortable with me playing with; it would be him.
Boss knows I enjoy meeting other guys occasionally for sex and kink. But for him to give his explicit okay for Jer means he holds him in the highest regards.
When I did bring up the proposition, there was a dead silence for a few seconds. My heart stopped. I just knew I went over that appropriate line. He did say that he would give it some thought.
He repeated that he is content with where he is now. I shared with him my point of view; How I would love to be more versatile as a bottom and how difficult it is to find a top that will top, someone who is patient enough to take their time with me and who I already have a good chemistry with. I also reminded him that his desire to top more with my desire to bottom more is a perfect combination.
He again mentioned that he would give it some thought.
It did sound a little promising as he did throw out a few dates available on his calendar. Time will tell.
