So, just to establish who and what I am, I'm a 52 year old real estate agent in a small town. Standing a very average 5'9", I weigh 170 pounds, with thinning salt and pepper gray hair. I'm bi-sexual, which in my case means that while I'm attracted sexually to both men and women, on an emotional level I only connect with women. I'd been curious about sex with men since high school, but my first sexual encounter with a man didn't happen until my mid 40s. After that, things were sporadic until my marriage failed 3 years ago. One the divorce was final, I was free to indulge my needs, and I did so, with the help of online sites where a guy could locate other men with similar desires. Right away, I learned that I was a bottom, liking how a hard rod felt up inside me, and I was lucky to meet another bi fellow who was an eager top. He was married, but we still managed to hook up fairly often. We explored the full gamut of positions and sex acts, from blow jobs, to rimming, to bareback fucking. He had a nice 7" cock of decent thickness, and once I was broken in, he could enter me with ease. Unfortunately, he suffered a heart attack while working in his garden. After his recovery, they moved to Arizona.
That had been 3 months ago, and I hadn't been motivated to find another partner. I was also between girlfriends, so my sex life was at full stop. A Saturday morning found me at work, clearing up paperwork, when I heard the door to the outer office open, so I got up and walked out to see who it was. To my great surprise, it was a guy I'd known years ago in high school. Roger had been 3 classes behind me, and had an older brother that had been my teammate in football. Unlike his brother, Roger gravitated towards marching band and drama class. Later, when I was in college, A friend told me that Roger had gone gay. We shared a laugh over it, and I forgot about it. Years later, I heard he was living with a guy. Now, he was standing in my office, and looking pretty damn good. He was shorter than I by a couple of inches, and stockier, with his blonde hair cut short. His eyes were gray, over top of a thin mustache colored same as his hair.
"Roger, how are you? What brings you back to town?" I stuck out my hand, and received a firm handshake in return.
"Oh, I need to get something done with my aunt's place. I'd like to list it with you, and let you take care of selling it. I'm too far away, and too busy to do it myself." We talked for a few minutes about what he'd hope to get out of it, then spent a while catching up. He worked for the postal service in the city where he lived, and casually mentioned Doug, the guy he lived with. He had heard about my divorce, and seemed curious that I wasn't seeing anyone. When I said that I was keeping my options open, he just gave me a funny smile. I had to admit, I found him very attractive, and if the opportunity came up, I was going to say yes. It came sooner than I expected.
"You know, we should hang out sometime, over a drink, get caught up on what my classmates around here have been doing. You ever get over to the city?" There was my opening.
"Yes, we have several properties listed there. I actually need to go and get some pictures of a new listing. I'd planned to do that later today. Too soon?" His face lit up with a big smile.
"No, no, not at all. In fact, my roommate is away for the weekend, so the timing is perfect. After you get your pictures, send me a text." We exchanged numbers, and he left. Later, while driving to the city, I thought about what he had said, about his roommate being gone. Maybe Roger had something more in mind than drinks? I sure hoped so. After taking care of business, I sent him a text, and he responded with an address for a bar. I found the place, parked, and walked in. At first, it looked like any other bar, just a few guys sitting at the bar and tables having drinks and chatting. But, after I ordered a beer and sat down, I took a closer look, and saw a poster for a Gay Pride event. Other things like the pictures on the wall clued me in, I was in a gay bar. Oh well, no one knew me, so I relaxed. Roger arrive a few minutes later, got his drink, and sat down next to me. We had a nice conversation, and ordered another round of drinks. He sat back, and looked me with a thoughtful expression.
"You seem pretty relaxed, Stan. You know this a gay bar, right?" I knew he was looking for a reaction, and perhaps an opening, so I gave it to him.
"When I got here, I was pretty sure it was. It's cool, I don't mind." I smiled at him, and he nodded.
"And you know I'm gay, right?" I sat down my glass, and looked at him.
"I had heard that, yes, but until you told me I wasn't sure. But, it doesn't matter, I'm open minded." I wanted to say more, but hesitated. He must have sensed it.
"How open minded are you?" There it was, and I decided to go for broke.
"More than most, I'd say. I've had sex with men several times, if that counts?" Roger's eyes widened, and he didn't say anything for a minute. Then he smiled, leaned forward, and put his hand on my arm.
"Yeah, that is definitely open minded." We looked at each other, and broke out laughing. The ice was broken, and I decided to press, just a little.
"So, you said your roommate was away. I've heard he's more than your roommate, which is fine by me. Can I ask, what the boundaries are in your relationship with him?
