Knowing for Sure Pt. 01

Phil and I worked in the same building for a couple of years after I had transferred into the corporate downtown office. Phil was in our communications department, and I was in finance. Our offices were near each other's, but we didn't routinely work together.

We'd see each other in common areas and when there was extra food placed out for anyone to graze over. If you've been in a big office, you know what I mean: Leftovers from lunch meetings, birthday doughnuts, holiday treats sent in from consultants. The makeshift buffet was always right outside Phil's office. If I happen to check out the treats, I'd usually be friendly and say hello to Phil.

Phil was a little older than me. He was about 6 feet tall and very fit. I always admired him for that. One could say he was attractive. He wasn't married, but based on the pictures in his office, it appeared he had been. I never consciously considered his sexuality, or so I thought. In retrospect, the signs were all there.

One night during the holiday season, we had a work holiday dinner. Phil wasn't involved as he wasn't in the finance department. However, at the restaurant that evening Phil was there with another group. The group Phil was with had been having a holiday gathering in one of the side dining rooms of the restaurant.

As that group broke up for the evening and headed out, Phil walked past the table where I was seated. I waved politely and said hello. He stopped to chat for a moment. He said that the group dinner that evening he was attending was a men's group from his neighborhood. He explained it was a group of friends that get together occasionally.

I said to Phil, 'That looks like a fun group,' not really implying anything.

My comment was based on the laughs they were sharing as they left the restaurant.

He said, 'It's just a group of friends I've gotten to know over the years since my divorce.'

He continued, 'You might hit it off with some of the guys. I'll let you know the next time we get together if you're interested.'

I tucked that away as polite conversation, not giving it much thought.

I saw Phil at work on and off throughout January and February. Towards the end of February, Phil made it a point to stop by my office.

He said, 'Hey! that the group of friends I was with at the Christmas party is planning to get together again soon. We wondered if I would be interested in joining us.'

I said, 'Yes, that sounds like fun.'

He said, 'Great. I'll let you know when we firm up our plans later in the week.'

A few days later, Phil let me know the group was getting together at his place. He said that because it's been so cold, they decided to stay closer to home and get together at his place.

Perhaps that should've been another clue about this group of friends. His neighborhood has a large gay community.

As the weekend approached, I had mixed feelings about going to the party. I enjoyed Phil's company and conversations around the office. We seem to have a lot in common. But I started to put more and more of the pieces together about the group of friends, and I wasn't sure if that was my crowd.

My situation at the time was that I was recently divorced. It had been a marriage too early in life, before I really had a chance to get to know myself, and there were frustrations with it, including the physical relationship.

Still, I never thought myself to be anything but straight, so I figured I would feel like an outsider if, in fact, Phil's circle of friends were mostly or all gay. Even though there was some trepidation, I still went, looking forward to meeting some new people.

When I arrived at the party, there were about eight or nine people there. The cocktails had already started flowing and people were relaxing and just chatting. Phil introduced me around and gave me a tour of his home. I'm not that intuitive in social settings, but it became clear to me that my speculations were in fact true. This was a group of gay friends.

Phil offered me a cocktail, which helped with some of the nerves, just social nerves. The party was enjoyable and went on very late. I met several new friends, all of which were very engaging, roughly my age and collectively a good-looking group of men. Some seemed to be couples, others were singles.

Towards the end of the evening, everyone was helping Phil clean up. I was in the kitchen, rinsing out some glasses and stacking them in the dishwasher when Jonathan came in to help me.

I had talked quite a bit with him earlier and we seem to have hit it off. We hadn't talked about anything other than hobbies, work, sports, etc. But the conversation was about to get more personal.

'Do you need some help?' he asked.

'Help always makes chores easier,' I replied.

'Great!' he said. 'We were all excited to have you join us this evening.'

'Thanks,' I said, 'Everyone's been so nice. I appreciate the warm welcome.'

'I wasn't sure how you would fit in with this group," he said, "but you seem to fit in nicely. I've heard only good things about you this evening.'

Again, I thanked him for the compliments.

Maybe it was the alcohol, but his next comment was a little more personal.

'So, none of us are sure although some have an idea... are you gay?' he asked.

It was a direct question. It caused me to panic a little bit, not knowing what to say. I don't know if that's because I didn't want to run the risk of being uninvited to future gatherings, or because deep down I didn't know myself. That was my answer.

I said, 'I don't know. I've never considered it.'

He said, 'Are you sure about that? Because most people that aren't gay know that and answer that way.'

He had me there. Maybe I was questioning my sexuality at that moment, having felt so comfortable with this group.

I said 'That's a fair point. I guess I've never had the chance to find out.'

Then he asked, 'Do you want to find out? Are you open to finding out?' He said.

'That's another tough question.' I answered.

He asked if I would you like to get together with just him next weekend.

'Like a date?' I said.

'Yes, like a date, but no pressure,' he said

'To be clear I never really had anyone ask me out on a date much less a guy ask me on a date," I said.

He said, "Like I said, no pressure, let's just get together, spend the evening out get to know each other a little better and we'll go from there. Either way, I'd like to get to know you. Besides, you will never know if you aren't open to the idea of at least considering it.'

We agreed to get together. I headed out shortly after that, the first one to leave since I had the longest drive.

The following week, there was a lot of anticipation on my part as the days in one sense seem to go by slowly, and then in another sense seem to be rushing towards some self-realization that I might not be ready for.

Getting ready that Friday evening presented a different kind of anxiety -- what to wear. I found myself entertained by that.

"How should one dress for their first date with another man?" I thought to myself.

My closet was not full of fashion-smart items. Just the basics. I pulled together the best outfit that I could. Jeans, a lavender button down left untucked, and some tasseled, preppy loafers. Maybe too cliched, but I felt comfortable.

I headed off to Johnathan's house with my heart racing the whole way. As I circled the block looking for a parking space, I found myself questioning what I was doing.

'Was I taking this too far? Was this path going to lead somewhere I wasn't ready to go,' I thought to myself.

I parked, walked up to Johnathan's door and rang the doorbell. I remember wanting to run, but then Jonathan answered the door so running was out of the question. I kept telling myself, just say "yes" to each next step.

To my surprise, we had picked out very similar outfits, but he looked much more put together than I did. I wasn't sure what that said about me being fashionable or that Johnathan was dressing down to help me feel more comfortable. I took it as Johnathan dressing down and being nice to help me feel comfortable.

He invited me in and we chatted a little. He showed me his home, which was a beautifully decorated, turn of the century brick home historic to the neighborhood.

He suggested we grab dinner a couple blocks away in one of the local taverns. It was a tavern with which I was familiar so, I agreed.

We walked down the street to the tavern, which had a reputation for being frequented by gay community members on the weekends.

I had only been there during the week for business lunches. It was a different crowd, for sure, that evening. But, for some reason I didn't feel uncomfortable. We started with drinks at the bar until a table was available.

We had dinner and shared a bottle of wine. At that point in my life, I knew very little about wine, but Jonathan seemed to know his way around the wine list, so I followed his recommendations. I found myself throughout drinks and dinner looking at Jonathan in a different light than I'd ever looked at another man.

I kept thinking to myself, 'He's on a date with me and at some point he may want to have sex with me!'

Johnathan was about six feet tall with a medium build, not muscular but ruggedly handsome. I had never interacted that closely with a man whose intentions may be to have sex with me in the near future. It was both scary and exciting and the roller coaster ride of emotions continued throughout dinner.

After we finished the bottle of wine, we both joked that it was good we had walked to the tavern and not driven because each of us was feeling our alcohol. When the bill came, I insisted we split the tab, but he would have nothing of it.

He said. "This is your night to consider new possibilities and it is my treat." He assured me there were no expectations.

The tab was paid and we headed back to Jonathan's house. When we arrived, we sat in his living room and continued our conversations. He commented that his buzz from the dinner cocktails and wine was starting to wear off and asked if I was interested in another drink. I wasn't driving right away so I took him up on the offer.

We sat in his living room on opposite ends of a large overstuffed couch, turned slightly facing each other. He began to ask more questions to get to know me better and how I got to this point, especially this evening on a trial date with a man.

I gave him a quick summary of my relationship experience from high school to my failed marriage. He wanted to know more about my roller coaster ride in my marriage that ultimately ended in divorce. Not intentionally or consciously, but I guess I had used the word "frustrated" a few times in my recap.

He picked up on that and probed a little more.

"Frustrated about what?" he asked.

Trying to dismiss the question I said "Everything."

"Surely it couldn't have been everything," He said.

"No, I guess you're right. Perhaps I wasn't ready and that situation was overly confining," I said.

"Was that the first person you had sex with?" He asked.

"Yes, as a matter fact, it was. How did you know?" I said.

"I guessed. Was it good?" he said.

"Having no reference, it seemed good," I said.

"Did you ever feel fully connected through your physical relationship with her?" he continued to probe.

"In some respects," I said, "but never felt comfortable enough to be vulnerable."

Where was my openness coming from, I thought to myself.

"Was that part of your frustration?" He pressed forward.

"I guess," I replied.

He continued, "So you didn't feel a consistent emotional connection with her when you were having sex?"

"Yeah, now that I think of it, I think that could've been part of it," I answered candidly.

Lubricated by the alcohol, our conversation seemed to be coming easily, or maybe it was Johnathan that was making it easy. I don't know. Both were intoxicating at that moment. Clearly, I was looking at my past in a different way deep down.

"Is that why you accepted my offer for a date this week?" he asked to put an exclamation point on the matter.

"Well, that may be deeper than I can unpack tonight after four or five drinks. That may be better suited question for some time in the future," I said.

"It's OK to process it slowly," he agreed, "It takes time."

He put his hand on my thigh and began to gently caress my leg. He said, "Maybe you just need something different to see if that fits better."

"That may well be the case," I replied.

He said, "Good, so another date?"

I said, "Absolutely, I'm enjoying our time together. But next time it's my treat."

He said, "OK, but no expectations. Right?"

I laughed and said, "I can't promise that."

It was later before I was ready to drive home, so we continue to talk. Our conversation made me feel more and more comfortable with Johnathan. He was easy to talk to and seemed to empathize with where I was emotionally. I was opening up in ways I had never opened up to anybody else before.

Fast forward to the next weekend. Johnathan and I got together for our second date. He lived in a metropolitan area, and I lived in a nearby rural community. Given that, there were many more options for entertainment and activities in the city, so I drove to his house again. Looking back, that had the effect of making me feel like I was pursuing him more than just geographically, maybe emotionally, too.

For the second date, Johnathan suggested we go to a local gay club. Understand, I am not the club type. I pointed that out to him jokingly after he made that suggestion.

"It's OK. You'll do fine. I just think it will be good for you to be around that kind of energy," he assured me. I agreed and off we went.

The club scene was very foreign to me, so Johnathan ordered some drinks to help us relax. He seemed to know several others at the club and introduced me around. The night was enjoyable, but I never really had enough cocktails to get out on the dance floor. Straight or gay, that was not part of my personality.

But there was a lot of banter and flirting amongst the group. The attention I was getting was arousing, but I couldn't quite tell why. I don't know what Johnathan had told them about me or my situation, but I assumed he had kept my confidence. Maybe they could just tell that I was exploring possibilities and Johnathan was serving as my guide.

We hit one other late-night club before retiring back to Johnathan's place that evening, or morning as it was at that point. We flopped on the same sofa where we'd started that probing conversation the week before, assuming similar positions.

"So, what have you been thinking about this week? Any new realizations? How'd you like this evening at the clubs?" That was a conversation starter if I'd ever heard one.

"The clubs were fun. Probably still not my thing, but I did enjoy the people and energy," I said.

"And?" he asked.

"What do you mean?" I responded.

"You only answered half of my questions. What about your thoughts this week after our conversation last weekend?" he asked.

I hesitated.

"Maybe some deeper realizations than you'd expected?" He pressed again.

"Maybe," I said, continuing, "It was certainly a lot to think about. I hadn't ever thought about being gay as an undercurrent to my marriage. But I guess it could make sense. Still, I don't have a reference point to compare."

"Isn't that why you've gone on two dates now with me? Aren't you wanting to find out?" he said, "You keep coming back so clearly there is interest."

He was causing some deep reflection on my part. If I was going to explore my sexuality, this seemed to be the perfect situation and timing to do so. Johnathan was patient. I was attracted to him. He was showing interest in me. It was all good.

"Saying yes to the next step is scary," I said, "It is a big step."

"I know, I've been there. But if you are going to know, it is a step you need to take if there's any question at all. I'm patient, but if you are ready, I'm very interested in taking that step with you," he said encouragingly.

I paused in thought, staring at the ice cubes floating in my cocktail. Our growing connection made me feel safe. I wanted to know, badly. Thoughts were going through my head like cars around a racetrack: "Am I gay? Is this the source of my frustrations, emotionally and physically? Am I ready?" "What if I am, how will things change for me?'

"Yes," I said, "I want to know. I'm ready to know. I want you to be the one."

"I was hoping you'd say that," he said," Ever since meeting you at Phil's party, I've had a feeling about you. Let's go upstairs."

I felt like at that moment I began an out-of-body experience. I followed Johnathan upstairs to his bedroom. He suggested we start with a shower to freshen up from the club-scene. The shower was big enough for two people, but it could easily fit four.

Johnathan turned on the water to heat up the shower. Still in the dim light of the bedroom, we began to undress. I hesitated, then Johnathan began to take off his shirt motioning for me to do the same.

He came up to me, placing his hands on my bare chest and looking into my eyes. He let his hands roam over my torso for a minute, then leaned in to kiss me. I had never been kissed by a man, but, by the response in my pants, I was clearly enjoying the experience.

He began to loosen my belt and unbutton my pants. He slid my pants and underwear down and helped me step out of them. I removed my socks and stood there naked in front of him.

He told me to take off his pants, so I did. My cock was hard at this point, but when his cock emerged from his pants as I slid them down I didn't realize how much harder I could get.

My out of body experience continued as I seemed to see my self from above, naked, in an embrace with another man. It didn't seem scary anymore. It seemed natural and comfortable.

He broke off the kiss and we stepped into the shower. We let the hot water flow over us from seemingly every direction from body sprays on each wall. His hands slid over me, cupping my balls, squeezing, stroking as we kissed.

He turned me around and placed my hands against the wall in front of me. He began to lather me up with the manliest soap I'd ever smelled.

He completely covered my body, probing the most intimate spots. I reciprocated exploring his body in the same way. It was the first time I'd ever touched a man like that.

There were no regrets at that moment, and I didn't see any in the future. I was only remiss in not having done this sooner.

We finished in the shower, dried and moved to the his bed. I emphasize "his" bed because this was the first time I'd ever been in another man's bed. The night was full of first times.

He laid me back on the bed and took a position beside me. His hands picked up where he'd left off, wondering over every inch, literally every spot, on my body. My hand drifted to his cock which was as hard as mine. I was having fun while learning, he was having fun showing me. We were both enjoying it.

He started to focus on my cock, which concerned me because I was afraid I'd climax too soon and end the night early. He moved down and took my cock in his mouth. His technique was artful, teasing and stimulating every part of my penis. But he was careful to edge me in such a way to keep my first homosexual experience going.

"Are you ready to try that?" he asked. My lack of hesitation at the offer to pleasure him must have been too obvious because he laughingly commented, "We have a convert! I knew it!"

I moved down to his cock and began to kiss and fondle him in every imaginable way. I wanted him in my mouth but knew that was the tipping point.

It was time to know for sure. I eagerly engulfed his cock with my mouth and began to slowly bob up and down. It was soft to the touch but rigid. His pubic hair was meticulously trimmed and neat as not to get in the way. The taste was new and intoxicating.

His physical and vocal response to my efforts was validation for me. It made me ever more eager to pleasure him. I took him deeper and deeper, as much as I could take into my mouth and throat. His hips began to move in rhythm with my head. We were in synch physically and emotionally.

I felt him getting harder and bigger so I knew what I was doing was bringing him closer to orgasm. I didn't let up. I wanted all of what the experience could offer.

With that, he put his hands on either side of my head and held me close. I felt his body begin to spasm, then I felt the flood of semen in my mouth. It was an amazing moment of self-realization. I had never felt that kind of connection with another person. I had given him intimate pleasure and consumed what his body offered in response.

"Was that the right way to do that?" I jokingly asked.

"Yes, are you sure you've never done that before? If not, you are a natural." He replied trying to catch his breath.

We laid there for a few minutes, my head at his waist, and me fondling his cock as it returned to its relaxed state. But, the emotions that were running through my head kept me aroused and firm.

"Your turn," he said. He rolled me onto my back and then began to stroke my hard cock. We were face to face.

"I'm not going to last long," I said.

He skillfully edged me while reinforcing and imprinting my new self-awareness while my mind was pliable in his care.

'You did a great job sucking my cock. Did you know you were that good?" he asked.

"No, I guess I didn't but I'm glad you enjoyed it," I said.

"Do you like this? Do you like being with a man? Do you like sucking cock? Is this what you thought it would be? Is this your new self?"

I answered "yes" eagerly to every question. "Do you know now?' he added.

'Yes,' I barely voiced under his intense touch.

'I want you to come. Show me what you've got,' he whispered as we were face to face.

With that, I released years of pent up mental and physical frustration. I felt wave after wave of satisfaction course through my body and mind. The out of body experience was over and I was fully present in my own body for the first time during sex. It was deeply emotional.

As I lay there post orgasm with Johnathan stroking my relaxing cock covered with cum, emotions began to flow. Johnathan had promised to help me take that next step, and a doozy it was.

"We're only getting started," he said as he kissed me. "So much more, so much more to know. I'm glad you decided to trust me."