Journey to Bi - Beginning Pt. 04

After Scotty and I stopped seeing each other, I didn't get much playtime. The pandemic lockdown happened and there wasn't much going on but the craziness. I was retired now and spent my days working in the garden, watching YouTube and online porn. The relationship with the wife had settled into a routine. She had finally reached the end of the hormone changes women got through and was a lot easier to live with.

I took the time to assess where I was in my sexual life and where I wanted to go. I had come to accept my desire for sex with men and women as natural. It wasn't something I wanted the wife to ever find out about though.

I found a fellow on KiK that I would communicate with. He was gay and had a boyfriend who couldn't visit due to the lockdown. We sent pics of our cocks and occasionally shots of jacking off. That too faded away.

Finally, the lockdown was lifted and life slowly started moving back to normal. Craigslist was not an option as it had shut down the personals section in 2018. Over the years I had created a few profiles on different websites to meet other men. I was contacted by several men and contacted a few myself. There were the usual email exchanges and pics swapping. Most guys were only interested in quick hookups but few could host. I couldn't host since the wife was retired now also.

I expressed an interest in finding a man who would like to walk the local greenways and hiking trails. One guy said he had an interest in walking.

Another man wasn't interested in hiking but had a big interest in sci-fi movies and shows. We had a few conversations about the shows we liked. He also said he had never had a guy cum in his mouth before and he was thinking about trying that with someone. He lived very close to where I did and he was married and could host at the right time. He agreed to do a meet and greet whenever I had the time.

I contacted the first guy and set up a time and place to meet and walk a short trail near the boat ramp in the neighborhood. I arrived early and was waiting on the bench at the trailhead. When the guy arrived I knew he wasn't the least bit interested. Older, chubby, not the least bit in shape. I could tell he hadn't done any walking or hiking in years if ever.

Sitting beside me he was breathing hard just from the short walk from the parking lot. He proceeded to tell me about himself. He was a former federal employee. He told of his wife, who was in ill health from cancer. From the attitude he had talking about her, he considered her a burden to him now. I didn't like this guy at all. He eventually started to talk about his extreme right-wing politics. I had enough at the point and got up and started up the trail leaving him there.

Going down the trail I shot an email to guy number two to see if he wanted to the meet and greet that day at the boat ramp. I was surprised he responded so quickly. He was all for meeting and said he was going to jump in for a quick shower and would meet me in about 40 minutes.

I finished the hike, drove over to the parking lot at the ramp, and waited. The guy showed up like he had said in a large pickup truck. It was raining slightly and chilly. No one was in the parking lot so we had the area to ourselves. He pulled up next to me and I got out of my car and got in his truck.

He was a smaller, thinner man with dark hair, in his mid-forties. We chatted a little bit, I asked him what he did for a living and he replied he was a truck driver for a local company doing short trips. Always back home at night.

Since we were there and the conversation was drying up I asked if I could see his cock. He unzipped and took his cock out. It was nice, about 6.5 and cut. I took mine out and he complimented me on how good mine looked. I reached over and took a hold of him and he did the same to me.

"Do you mind?" I asked. Meaning could I taste his dick.

"Sure," he said.

I leaned over and ran his cock in my mouth. The console in the middle of the seat was making it difficult. I leaned back up and said so. He pressed some release on the console and lifted it out of the way. I went back to his cock. He was rock-hard. I was enjoying this. I worked on his cock doing my best to make us both feel good.

I had never played with a guy in a vehicle before. I had played with women before, especially back when I was a young guy going to the local make-out spots. Being in the truck, in public, and sucking a dick was exciting for me.

After a few minutes, I let go and sat back. He leaned over and took my cock in his mouth. As he was sucking me, I remembered how he said he had never taken cum in his mouth. That was about to change.

He was down in my lap sucking me. I knew I was about to cum so I put my hand on his head and held him there as emptied my balls into his mouth. For a guy that said he had never taken cum, he was doing a good job catching and swallowing mine.

When I was done, he raised up and sat back in his seat. I moved over and took him in my mouth again. It didn't take long before he began to moan loudly. I could tell he was having an orgasm but I wasn't feeling or tasting any cum on my tongue. He groaned and huffed loudly. His body shook as the orgasm rolled over him.

He calmed down and I sat back. We both zipped up and I said I guess I should be going. I got out of the truck in the misty rain, got in my car, and went home.

I emailed him later that night but he never responded.

I met up with another local guy and we traded oral in the back seat of his crew cab. That was another one and done.

I didn't make a habit of having sex in vehicles, but it was exciting to me. Several guys, I did a meet and greet with ended up with some looking and touching. I've sucked cock five times in a vehicle and only three of those ended up with the guy cumming.

Searching on the web I came across a Craigslist replacement and started going through the listings there. One posting caught my attention. A man was looking for a 'workout' partner who would be interested in getting together to exercise a muscle. I contacted him and stated I was interested in working out. He said his name was David and he lived in the same town as I do. We exchanged emails to break the ice and get a feel for what the other was looking for. He was naturally cautious, and so was I. You never know what the other is really like so it's a good idea to find out as much as possible before meeting. We chatted on the phone and David said he was looking for a guy to come over and watch porn and jack off. Possibly, if we were comfortable enough with each other, we would jack each other off. I told David I was fine with that, it's what I was looking for when I first started playing with men that was several years ago.

It took David a few weeks before he finally was comfortable enough to set up a visit at his place. Even on the day of the meeting he called me and was hesitant. He had yet to give me the address to his house. I didn't push the issue with him. I was out anyway and if he wanted company then I'd come by since I was in the area. He called back later and gave me the address and directions to his home as I drove. His instructions were to come straight in, be sure, and lock the door. He would be in the back bedroom waiting.

I arrived in just a few minutes making only one wrong turn. Parking in his driveway I went to the front door, entered, and locked the door as he had instructed. The hallway was off to the right and I went down the short hallway past the bathroom on the left, on the right was a bedroom that was decorated bright and colorful. I figured that the bedroom was where his wife slept. He had said he was married and that he and the wife were also in a sexless relationship.

At the end of the hallway was a bedroom on the left, and on the right was another bedroom that was set up as an office. I stepped to the bedroom and David was lying on the bed naked. He was a big guy. Even lying on the bed I could tell he was taller than me. I'm 6' myself. He was a large guy, I say he weighed close to 280 or 290. He was in his early fifties. He had short hair and a beard that was grey. He wasn't someone I would consider hairy, but he was beefy.

I've always had an attraction to women that are fluffy. I find ladies who are commonly referred to as BBW to be sexy. I also find a large man to be desirable. I have a size limit though, I'm not attracted to those that are very obese. I'm more into men under 300 and women under 230 tops.

'Hello," he said. "How's it going?"

"Hello," I replied. "You not that far from my neighborhood."

"Oh, that's good," he said.

David was lying naked on the bed playing with his cock. He wasn't very big in that area. His dick was what I think of as an arrow. The head is more pointed than mine, which is more of a mushroom shape. I estimated his cock was about 5.5 inches long, possibly close to 6. Being such a big guy his cock looked small in comparison.

There was porn on the TV screen. It was straight porn, two good-looking people having sex with a lot of moans and groans. I wasn't very interested in that. I prefer seeing older couples, chubbier girls, and more natural sex scenes than what he had playing.

I stepped beside the bed and got undressed. I got in the bed beside him but kept a comfortable distance between us. I could tell he was very nervous. I lay on the bed and started playing with myself as I pretended interest in the movie.

David was staring straight at the movie, but I knew he was wary. From our conversations, I knew what he wanted. He wanted to be jacked off and to jack me. He was wanting to make me cum, to see the cum come out of my cock. He had told me about watching porn clips of guys cumming and he wanted to see it for real. I had sent him a video of me jacking off one morning and he said he played it over and over several times. It was a pretty good gusher.

I looked at David and said, "Do you want me to jack you?"

"Yeah, that would be good," he confessed.

I moved to get between his legs and took his hard, pointed cock in my hand. David felt nice. I worked on him for a bit and took his balls in my other hand. He was enjoying the feeling with apprehension I could tell. He had closed his eyes and was beginning to go with the flow.

I thought if he liked this he'd really like my mouth on him.

I leaned forward and put his cock in my mouth. David bolted up from the bed. "No, no, no!" he blurted. He pulled away from me and jumped out of the bed.

He was very upset. I knew I had screwed up big time.

"I'm sorry," I said.

David was agitated and said, "I can't do that. That wasn't what I wanted."

"Oh shit," I thought.

I apologized several times as I started putting my clothes on. I was confused. In some of our conversations, we had discussed oral. He had stated that he had never done oral on a man, he was curious to try it.

After getting dressed I walked toward the front door. David followed. I apologized again and left.

Driving back home I was confused over what happened. What type of guy was I dealing with? I was a few miles down the road when the phone rang. It was David.

"Hello?", I answered

"Hey. I'm sorry for what happened," he started. "I didn't want to do that."

"I know," I said, "I didn't think you'd mind if I did oral on you."

"I don't think I'm ready for that. I have issues about oral."

"You do oral with a woman?"

"Yeah, but with a guy there's some issues that go back a long way."

"Look I'm really sorry. I didn't mean to upset you."

"I understand. Would you be willing to come back?" he asked.

I thought this over for a few moments.

"Ok, I'm just now pulling out of your street so I'll turn around."

I went back and he was again on the bed naked. I got naked again and got in the bed. This time I wasn't going to make the same mistake.

The porno was still on the TV, but I ignored it. I got between his legs and started playing with him. I moved up close so our cocks could rub together. With my hand, I held both of our cocks together and stroked. I could tell he this was more of what he wanted.

He started cumming and I used his cum to coat his cock, making it slick as I was rubbing and squeezing cum out of the slit. When he some empty, I rolled over and lay on the bed on my back. My dick was stiff.

David was still for a bit. He looked over and me and asked if he could jack me now. "Sure," was my reply.

He took my cock and started stroking. I didn't try to hold off my ejaculation and came fairly quickly. David watched my cum ooze out with an interest. When it was over, David said I could use the bathroom that was attached to the bedroom. I got up and took some toilet paper to wipe off the cum on my stomach.

I stepped back into the bedroom and started getting dressed. David was standing at the foot of the bed. After dressing we walked to the front door. I said thanks for the invite and he said he'd be talking to me later.

A couple of weeks went by before I heard from David again. I had given up on ever getting an email from him. Again we exchanged mail, he was still working from home so he had time to play. His wife worked also, but she had to commute to the neighboring town. During the course of the exchanges, we discovered that we both had a thing for BBWs. He said he used to have a BBW girlfriend that he would go see whenever he could. He and another guy had a threesome with her and he sent me some videos and pictures of her and them together.

We got to the point of emailing at least one day a week. Some weeks he blocked off some time when he'd invite me over. Usually, those were the days he got a little high and that made him horny. I found out that the higher he got the hornier he was and the more willing to play. Since he knew I loved the big girl, he'd have some big girl porn on when I got there. That was a lot more stimulating for me than the 'skinny girl straight' porn.

One day he was high and horny with some spare time and asked why don't I come over. As usual, come in and lock the door, he'll be in the bedroom. He was naked on the bed. I've never seen him dressed any of the times I've been there. I got undressed and got in the bed. Some big girl porn was playing and I commented on how hot the girl was. His cock was agreeing with that, being hard and up.

I got beside him and started stroking and sucking his nipples. I could tell he was very high. Taking a chance I asked him if he'd like a blow job. To my surprise, he agreed. I moved down between his legs and started sucking him. I made sure he could still see the TV, hoping that would keep him going and he would not react in a negative way in the middle of the blow job.

It was a short blow, he was cumming in no time. I took his load and swallowed him down. He was rolling from the sensitivity of cumming. He was pushing on my forehead to get me to release him. I did, but I licked the cum pooling on the end of his dick. I could tell he enjoyed the orgasm. Then he did something unexpected. He got up and went into the bathroom got in the shower and started washing. I stood at the door and asked, "Did you like it?"

"I'm still processing it. I'm not completely comfortable with that yet."

"That's OK. At least you let it happen this time. I'll tell you, I enjoyed the hell out of it."

I went and lay back on the bed. He got out of the shower, dried off, and came back into the room.

"Do you want me to jack you off?"

"Sure," I said.

He stroked me and I came fairly quickly. He liked that, he kept rubbing my cum on my cock. Once he released me I went into the bathroom and washed up. I dressed and he walked with me to the door and I left.

A couple of weeks passed and I received an unusual email from David asking if I had ever done anal. I replied I never had. I told him I was more interested in oral than anal. The email chain ended with David saying that we are on different pages at this point.

I didn't hear from him for a month after that. Taking a chance I sent him an email saying was interested in trying anal with him. I reasoned that if I gave him what he wanted I'd get what I wanted. I didn't say anything about oral to him. I could tell he was excited to do anal and he invited me over.

I came over and got naked. David had a condom and some lube. What would be the best position? I suggested he get on the edge of the bed on his back. He lay down and brought his knees up. This wasn't going to work. He was too low for me to get near his ass and was putting me in a stressful position.

"Get off the bed and bend over," I said.

David got off the bed and bent over. This was better I could get closer to his hole this way. I still wasn't fully into this. I just didn't have a lot of desire for anal, not even with women.

I squirted some lube on the condom I had on and some on his butt hole. Spreading his buttocks I pushed my cock toward his hole. I didn't go in. I pushed some more, still not getting in. I rubbed my dick between his butt cheeks. My cock was slipping in and out of his cheeks like I was fucking him but I wasn't getting in his ass one bit. I grabbed his hips and tried again and again.

Then it happened, the motion of my pushing my dick between his cheeks made me cum. I spilled my sperm in the condom and never got inside of David at all. My erection began to soften.

Dang! What now?

I released David's hips and stepped away. I was pretty embarrassed.

"I'm sorry. I couldn't get it in."

David stood up and said, "That's ok, we'll try again some other time."

"Let me jack you off," I offered.

David lay on the bed and I gave him a hand job. I dressed and left after that.

End of Part 4