Journey to Bi - Beginning Pt. 05

Part 5

The journey hasn't been linear. There have been lots of twists and turns. There were periods of overlapping experiences with men. I have met different men over the years, the majority weren't more than a simple meeting in a public place. Fifteen minutes to say hello and then leave with no further contact.

Then there were the long periods of not meeting anyone and wondering if I would ever play with another person again. I've long since given up on finding a single person who would be a regular partner long-term, it's just not realistic.

My bi-curiosity didn't begin when the marriage became sexless. It began as a teenager and a good friend gave me a handjob in the basement of my parent's home. It developed with the circle jerks with the other boys of my age on the camping trips. I didn't start pursuing my bi-nature until I was in my mid-fifties. Sometimes I wished I had started at a younger age, but that's not the way things worked out.

I had not heard from David since our last visit together. David emailed me when he got high and horny. It had been a couple of months since the anal incident. He was high this time because he said he had been thinking about doing oral. That must have been potent weed he was puffing to bring him to the desire of trying oral. He asked if I would come over so he could try it. He wanted to do it while he was high and horny or else he was afraid he'd change his mind.

I headed over to his place and found him in the bedroom naked as usual with a big girl video on the TV. I undressed and got in the bed. Piling up the pillows against the headboard I was ready for him.

David got between my legs and took my cock in his mouth. For a guy that was doing this for the very first time he was doing very well. Almost too well, I was getting very aroused I didn't want to cum too fast so I told him to slow down some. I was pretty sure he wasn't ready for me to cum in his mouth. David let go and asked if I minded if he put a cockring on me. I told him that was fine. He rolled off the bed and got an adjustable cockring and some coconut oil. He rubbed my cock with coconut oil and slipped on and tightened the ring. I thought he was going to resume the blowjob because he got close to my cock. Instead, he started stroking my cock. I kept thinking he was going to put it back in his mouth but he just kept working me with his hand until I finally came. He couldn't bring himself to put it back in his mouth.

I got out of bed and went into the bathroom and cleaned the cum off. I thanked him, got dressed, and left.

Meeting Mark

Reading through Doublelist I came across a posting of a man in the same town as me. I shot a response and received a reply within an hour. Mark and I set a meeting date at a local restaurant.

Mark was much older than I was at the time. He was pleasant and we had a nice friendly lunch. At the end of the meal, he invited me back to his place. He lived in a local retirement community close to the restaurant.

I followed him to his place and parked in the drive. We went straight to the bedroom and both of us got undressed and got in the bed. We lay there and cuddled for a bit.

Mark began telling more about his life. He had mentioned during lunch his wife of many years had died several years ago. He told me how lonely he had been since her passing. I asked him when he began playing with other men. He said he went to an adult bookstore one day went into a booth, and sat down in the chair to watch a video. He said a man came in while he was watching the porno on the little screen. He said the man, unzipped his pants and took out his cock, and put it near his face. Mark said, he took the man's cock in his mouth and sucked him until he came in his mouth. He said he just swallowed the guys' cum and that's when he discovered he liked cum.

We kissed and hugged, then I rolled over on him and moved down until I could get to his cock. It was soft and small. I began sucking him and he started moaning and being very vocal about how good that felt. I kept working on him, but he wasn't getting hard, at all. I sucked his balls and tried jacking him, but he wasn't getting hard. I stopped sucking him and looked up at him.

"I don't get hard," he confessed.

"Oh. Do you cum?" I asked.

"Yes I do," he replied.

I went back to working on him and he continued to be very vocal, moaning and groaning. Eventually, I knew there wasn't going to be an orgasm. At that, I moved back up beside him. Mark then said, "I'll suck you." And moved down to give me a blow. He was pretty good at it, and it wasn't long before I was climaxing and shooting a load of sperm in his mouth. Mark swallowed me and cleaned up the after drops that come when the cock softens.

I lay there in the after-glow for a time before getting up and getting dressed. Mark apologized for not getting hard or cumming. I said that was fine. I would have preferred to have been told that at first. He confessed that in the past when he told that up front guys would decline meeting with him. I have no problem playing with a soft cock, but I like to know upfront what the score is.

Meeting John

I met John through a gay website. He was close to my age and retired. We met at the local greenway close to his home. A very nice and considerate person that I liked when we first met. He was gay but not out to anyone but the person who lived with him. John insisted that the roommate and he were not together, even though the roommate considered themselves as a couple.

John was smaller than me, not as tall, and weighed less.

The roommate worked out of town for a few days each week. Those were the days he would invite me over.

The first time I visited John invited me in and we went to the bedroom. Soon we were naked in the bed and cuddling. John was very passionate which I was enjoying greatly. We kissed and hugged and rolled around in the bed. I'm very oral and I was soon on his cock enjoying giving him my best effort.

John and I had discussed anal a few times and I was more interested in giving it another try. My last effort with David wasn't a very good experience. At least with John, there wasn't any pressure. One day while we were playing I picked up one of the condoms that he always kept on the nightstand. I slipped it on and tried entering John while he was on his back. I couldn't get the right leverage so I rolled off the bed and had him bend over the side of the bed.

I rubbed my cock over his ass and slipped in easily. I was surprised at how good it felt. I pushed in deeper and he gave a low grunt. I began to slowly fuck him. Holding his hips I pushed in and pulled out slowly.

"Is this okay?" I asked him.

"Oh, yes," he said.

This was feeling good to me. I began to fuck him faster, my cock was beginning to pound his ass. My orgasm was building and I was going to cum. I released my sperm with a hard push into his butt filling the condom.

I pulled out slowly.

"Save the cum for me," he said, as I pulled the condom off. John took the used condom, climbed into the bed, and emptied the contents in his hand. He then started jacking off using the sperm as a lube. I got in the bed laying next to him. I watched as he jerked himself off with my cum.

Anal sex with John became a very pleasurable thing we did. I didn't always have an orgasm when we did anal, but the act itself was something we both enjoyable.

That became a regular thing with us. Regardless if it was anal or oral John would save my cum to jack off with.

Meeting Ryan.

Ryan was a musician like myself, only he a professional and I am strictly amateur. We were also the same age and he was in a sexless marriage. Ryan said he hadn't ever played with another guy, but he wanted to. He wanted to try oral with someone. He also lived in the same town as I do so that would make meeting easier. He was about 5' 9", around 170lbs, with grey hair.

We communicated for a week or so and then planned a meet and greet at the park where I had met the first guy, whom I had given a handjob.

I arrived first and didn't have to wait long. Ryan parked next to me and I got in his car. We exchanged greetings and engaged in some pleasantries. Ryan said there were days he could host, his wife worked part-time and on those days he could invite me over.

"Do you want to see my cock?", he asked.

"Sure," I said.

Ryan unzipped his pants and pulled out his cock. It was nice, cut, around 6" long. I reached over and gripped his cock. It was nice and warm. He started to get erect as I was touching him. He reached over and rubbed my crotch, that made the head to peek from under my shorts. Ryan started playing with the exposed head of my cock. This was getting me so aroused I couldn't stop myself from cumming. Fortuitously, I didn't cum that much by putting so much effort into not cumming. Having climaxed embarrassed me, Ryan didn't mind. He was happy to see me shoot, even if it was just a little. I told him how car play makes me so horny.

We parted with Ryan saying he would let me know when his wife was scheduled to work and we would get together. I got in the car and wiped up the cum from my leg and as much of it as I could from the short pants I had on.

Ryan shot me a text the following week saying his wife was going to work that day. Could I come over around 2:00 in the afternoon? He sent the address and I got ready to head over.

When I got to his house I sent a text that I was in the driveway. A few moments and the garage door opened and Ryan met me. He asked if I wanted to play in his car which was in the garage, but I said I preferred to go in the house. We entered the house and he led me up to the bonus room above the garage. It was a big open space with a big leather sofa.

Ryan said to take off my pants and I could leave my shirt on. I had the idea that he wanted to keep his shirt on for whatever reason. It didn't matter to me one way or another.

So I removed my shoes and dropped my pants. He did the same and we sat on the towel that was spread on the couch. I reached over and started to rub his cock, while he did the same.

"How do you want to do this?" I asked.

"I'll suck you first," he said.

"Do you want me sitting or standing?"

"Stand up."

I stood up and faced the couch so that my cock was level with his face. He stroked my cock a few times and then took the head in his mouth. I could tell it was the first time for him. He was very timid. He held my cock with his index finger and thumb and barely put the head in his mouth. He wasn't sure what to do. He would 'stroke' me with his finger and thumb, and then he'd bob his head on the end of my dick a few times.

"You don't want me to cum in your mouth do you," I said.

"No. Tell me if you are going to cum."

I figured one reason for the timidness was he was afraid I would cum in his mouth. Another reason is that he had no experience with this at all. I encouraged him by saying how good it felt and how well he was doing.

"You're so big," he said. I am close to seven inches and have a thick cock with a nice mushroom head. Guys never took the whole shaft in their mouths, but they do get the head and a couple of inches in.

Ryan was still trying to figure out how to do oral. I was hard, but I wasn't going to cum like this. I said lets swap now and let me suck you for a bit. Ryan got back on the couch and sat next to the arm so that his back was in the corner. He pulled up his legs and knees on the couch. I knelt on the floor and got his cock in my mouth. From my oral experiences, I had developed a few tricks that the guys seemed to like. I was just beginning to work on his cock when he stopped me.

"What's wrong?" I asked.

"I'm going to cum."

"Yeah, isn't that what you want? I'm all for it."

"I don't want to cum this quick. I usually don't cum as fast."

"Ha, like I did in the car?"

I went back to working on his dick. He was nice and stiff and I was enjoying it.

"Oh, I'm going to cum!"

"Mumhumm," I moaned.

He let go of what felt like a nice load. I felt it shoot up on my tongue and I let it slide down the back of my throat. I used my lips to pull out as much cum as I could get. He was pulling his hips back as I drank him in.

When I let go and sat back on my heels, Ryan was shaking slightly. I got off the floor and sat beside him.

He looked over at me. "Do you want me to suck you? You're too big to get my mouth around it."

"I'll tell you what. Just jack me off."

Ryan took some tissues from the box on the end table by the couch. Taking hold of my cock with his finger and thumb he did a few strokes.

"Look," I said, "get your hand around my shaft. Grip it like a baseball bat."

He wrapped his hand around me and started to pull the skin up and down my shaft. That was better. He was so new to this. I didn't try to inhibit my climax. I let the cum ooze out of my cock and he wrapped the tissue around the head.

I took the tissue from Ryan and wiped the head of my cock clean. That's when Ryan's phone rang, it was his wife calling. I got up and put my pants back on and my shoes. Once he hung up, we returned downstairs and I left for home.

A couple of days later Ryan sent me some pics of his wife naked. That was nice. That's something I don't have. There was no way in hell my wife was going to let me take nudies of her. He began a conversation about how much he'd like to see me fuck his wife. He talked about how he would like to see my 'big' dick fuck her. It was a fun fantasy. He wasn't the only married guy that had shared that fantasy with me.

It was a couple of weeks before we played again. He wanted to try oral again, so this time I told him to relax, don't worry about my cumming in his mouth. Enjoy the experience. He sucked me for a bit and then I said I wanted to do him, so he could relax some. His cock was limp when I took it in my mouth. It was just a few minutes and he begged me to stop.

"I'm about to cum."

"Good, that's what I want."

"No, I never cum this quick."

"OK, that's not a problem. Getting you to cum is why I'm doing it."

"No, there's something wrong."

"Just relax, it's ok."

He was insistent that I stop sucking him. He didn't want to cum so quickly. I stood up and he took my cock in his mouth trying to suck me. He did that for a time, and then just began to jack me off. I told him I was going to cum and he had the tissue handy. I looked down at his cock and there was a pearl of cum on the end of his dick. I reached down and wiped it off and licked my finger. I started cumming then and he was quick with the tissue to catch the sperm.

I left after getting dressed.

Ryan and I have texted since then, I haven't gone back for a visit in a while. He's still not completely embraced the idea of sucking cock yet. He likes to talk about it and ask questions. He will still bring up about cumming so quickly which never happened to him when he was with a woman. Later he began asking a lot of questions about if I had ever done anal. I told him I had topped a limited number of times. Ryan and I have not gotten together to go any further.

Meeting Johnny.

I met Johnny through a website that was geared toward older men. We hit it off very well trading email and pics. We were the same age and had similar experiences and interests growing up. When I mentioned one day I play a lot of disc golf he was all excited. He had been looking for a DG partner since he retired. "This was great!" he said.

We made a play date and met at the local course. It's a small local course that isn't busy during the weekday. It was empty the day we arrived. Meeting for the first time in person was great, we connected like we had known each other for a long time.

Starting on hole one we played our way around the front nine until we came to hole eight. Disc golf courses are often constructed in wooded areas. Eight is located in the middle of the course, the deepest part of the woods. There was a bench located by the tee pad so I went and had a seat. John came over and sat beside me for a breather. I put my hand on his leg and moved it up under the pant leg of his shorts. He caught on to the idea quickly and stood up and unzipped his pants. I moved him over in front of me and started playing with his dick. He got erect once I had him in my mouth. I had him positioned so I could see if anyone happened to show up. I had him deep between my lips when he came. It was a nice creamy load of cum that I let slide down my throat. I finished him off, cleaned the head of his dick of the extra leakage, and zipped him up. That's when I saw a couple of guys on one of the other holes walk by. They were too far to see what we had been up to.

From there we teed off and finished our round. We had other play dates after that. We had a running bet, the one with the best score by hole eight, gets the blow.

Meeting Jamie.

Jamie and I met through a gay website. Of all the guys I have met, he and I have spent more time conversing together. He's married and has a very sexy older wife. Jamie is a big man, over six foot tall, close to six-two, or six-three, broad and hefty. He weighs close to 300. As I had stated earlier I do like big men and women. His cock is about six inches long with a nice head.

Over the years one thing I have come to appreciate is communication. Jamie and I would communicate often about a lot of different things.

We have played a few times, I enjoy getting naked with him. I do like being next to a large guy. I enjoy rubbing his belly and sucking on his nipples. His cock gets very hard and fits nicely in my mouth.

Jamie has a desire to see his wife with another man. Many married men have this fantasy. Some have been fortunate to have seen it happen. We would share this between us. We would tell each other how we'd like to see the other with the wife, fucking her, eating her pussy, putting our cocks in their mouths. It got each of us very aroused.

There are times when he and I are playing and I would be sucking his cock, or rubbing my cock between his butt cheeks he would tell me about fucking my wife or having my wife's mouth on his cock. He'd say, "I'm cumming in your wife's mouth. She taking all my cum." I would say the same about his wife. When I'm topping him, he would say that it was his wife's pussy I was fucking.

I hope one day he gets to see her with another man, if not me, someone.

The way it is today.

It's been over 10 years since I started this journey. The wife and I have settled into a living arrangement where sex isn't going to happen and that is just the way it's going to be. She knows I watch porn and just ignores me when I do. I don't think she even considers what I do for sexual release. There was a time in the past if we went too long without having sex she would wonder if I was out running around.

Sometimes I wish that I could come out to the wife, only she would not understand the desire and I don't want to go that I have heard of guys who say their wife knows, but I've never met such a unicorn.

I've become comfortable with playing with other men. It's become natural and still as exciting as when I jacked off the first guy.

This is where the journey is now, where it goes from here I'll just have to see.

End of Part 5