A Cruising Life Ch. 05

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Two Firsts in One Night.
3.3k words
4.63
11.2k
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Part 5 of the 8 part series

Updated 06/09/2023
Created 04/25/2020
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tommydntx
tommydntx
45 Followers

As always, thanks for reading my stories. The comments and feedback are appreciated.

This is the longest story so far. As with all my stories, it is a recollection of true events from my life as an over-sexed, bisexual male. Picking up where Chapter 4 left off.

Over the next several months I checked out a few other local arcades. After some successes and a few failures, I wound up with a nice network of four places that I considered acceptable based on things like location, cleanliness, security and setup. The most important single criteria though was that there was action.

One of these places was on what is called Dixie Highway, which is the direct route from Louisville to the US Army base, Fort Knox. This place was up on the Louisville end, and was part of a motel. The motel itself probably dated to the 1950's when Dixie Highway was a primary north-south route.

By this time though it had turned into not only a motel for hookups, but also a bookstore and arcade in the part of the building where the office would have been. I never checked out the rooms, but heard stories of people, male and female, leaving the curtains open while they fucked and stuff like that. It was a long, horseshoe shaped layout and I was never comfortable just strolling back into what looked like a place one could get trapped.

The arcade was pretty good, with about ten booths arranged in a semi-circle on the other side of a wall behind the counter. Booths one and two had what was probably the largest gloryhole in town. You could easily get your hand through the hole while sucking someone to play with his balls and even his ass.

There was also a small theater in the arcade area. At this point in time, I still wasn't comfortable with being in the same room as the other person, so I didn't have much interest in the theater. One day when business was slow, I did step in and check it out when I knew I was alone. This one wasn't particularly well laid out, but I did get a little excited wondering what kind sex went on in this room for everyone else to see.

The fourth place was in the city of Louisville going towards downtown on the corner of Hill Street and 7th Street. The most interesting thing about this place was there were absolutely no markings on the outside telling anyone what it was. It was in an old building with the door on the corner.

The arcade was behind a wall on the right with the entrance about halfway down. It was directly across from the counter. The booths were in a straight line. There were about twelve to fifteen of them and most had glory holes. I never figured out why, but this place was particularly good on Sunday mornings, with lots of guys looking to get sucked. I spent many Sunday mornings there, sucking as many cocks as I could.

Between these two, the one I called Number Two in the last chapter, and my original place I had options if action was slow at one, or I happened to be in the area of another. The total distance between all four of them was less than thirty minutes and there were times when I hit all four in the same day.

While the other three were acceptable, I was always drawn back to the original. As I've said before, it was comfortable to me. So, it was when I was there one night that I had another first-time experience. It wound up being two first-time experiences in one night.

I'm not sure if this is true of everyone who frequents arcades, but along with having a favorite establishment, I even had a favorite booth. There wasn't any logical reason I favored one booth over the others, other than I was comfortable when I was in that booth.

On this night, my favorite booth was occupied, as was the one next to it and the three on the opposite side of the hall. Busy night. This meant I had to go across the store to the other hallway, a place I rarely went. I found a booth and started my usual routine of getting out of my pants to be comfortable.

As soon as I sat down and began stroking my cock, I noticed movement through the hole. The booth wasn't occupied when I went into mine, so he must have entered right after I did.

There was a lot of rustling around over there and I leaned in for a peek. The guy was getting completely naked. While I wasn't far behind, having only my shirt on, I was instantly rock hard at the site of a fully naked man right in front of me.

With me still peering through the hole he did the finger thing. I stood up and slid my cock through. He didn't even wait for me to get it completely through the hole before he started licking and sucking on the head. Like most arcade professionals, this guy was very good.

Since I had just arrived, I was in no hurry to get off and hoped to enjoy a little back and forth with this guy. The glimpse I had gotten of his cock let me know he was cut, (which I prefer), and probably about six inches plus when hard.

After a while I tried to pull back so I could signal him that I wanted to suck, but he was having none of that. When I attempted to pull away, he clamped down hard with his lips.

After what must have been about ten to fifteen minutes, which is an eternity in most of these situations, he let go with his mouth. I instantly tried to pull back, but he grabbed my cock with his hand and started stroking it. I know sometimes in a marathon sucking session my jaw will just get tired and need a break, so I thought that might be what was happening for him.

I could hear more rustling around, but he continued to stroke me. Then I felt something cool and wet on my cock while he stroked.

The next feeling was what I thought were his lips on the head. I still couldn't figure out the cool, wet feeling but at this point it didn't matter as long he went back to sucking.

As he took more of my cock it just felt different. It was warm and smooth, just as it had been, but somehow different. When he had it all the way in, he just stopped for a couple of seconds. The next feeling was of him pulling off, them plunging back down. When he hit bottom, there was a noticeable thump on the wall.

While this felt good, I was dying to know what was different. His up and down movements on my cock were into a slow, steady rhythm now. After less than a minute of this I couldn't stand the suspense any longer, so I quickly and unexpectedly pulled my cock back through the hole.

When I looked down my cock was slippery and glistening. I looked to the hole, expecting to see his mouth and him telling me to put it back through. Instead, I saw what turned out to be his ass crack. In an instant, it all made sense. When he stopped sucking me, he applied lube to my cock, turned around and took me in his ass.

While I was developing a serious liking of playing with my own ass and inserting things into it, I had never fucked another man and had never been fucked. Now that I knew what it felt like to have my cock in an ass, I wanted more.

Before he could move away, I shoved my cock back through the hole and into his ass. Now that I knew what was happening, I took over and started sliding my cock in and out of his ass. At first, I was trying to match what had been his pace when he was controlling the action. Man, this felt good.

I kept fucking him slow and steady. I started wondering what he was doing on the other side of the wall. Was he stoking his own cock? What would his ass feel like when he shot his load? Would I even know when he had cum?

After a little while he started moving again. I took this as my signal to pick up the pace. I began thrusting a little faster and holding it in him just a split second longer on each thrust. As funny as it sounds, through all of this, cumming had stopped being my goal. I was more interested in enjoying this new experience for as long as it could last.

The guy on the other side was obviously focused on cum. Mine. He started moving again and I started going faster, eventually slamming into him harder and faster than I had ever fucked any woman.

At this pace, and after this much action, it wasn't going to take long for me to cum. When the feeling started, I tried to go even faster, but I'm not sure that was possible. I just kept driving my cock into him.

Then, the question popped into my head of where was I going to cum? I immediately realized this wasn't my decision and that I should leave that to him. If he wanted me to cum in his ass, who was I to deny him that pleasure?

Turns out that was just what he wanted. As I kept up the fucking, he stopped moving. I pictured him standing with his hands on his knees, backed up the wall taking my cock. As I processed this imagine in my mind my cum shot deep into him. I buried myself in his ass and shot spurt after spurt.

I caught by breath and began to soften, easing my cock out of his ass. As I looked down at my cock, I remember being pleased, and a little surprised, that it was perfectly clean. There was a little cum dripping from the slit which I used as lube to stroke it lightly.

I dropped to my knees to see him sitting in the chair, still naked, watching the movie and stroking a very erect cock. I put my finger through the hole but saw him shake his head. I stayed there watching him and after a short time he came to the hole. He thanked me for what he called a very good fucking, but said he wanted to be fucked at least once more before he got off.

I found it quite incredible that after all the sucking and fucking he hadn't cum. I told him I would need a few minutes to recover but would fuck him again. He thanked me but declined, saying that getting fucked by different people was part of the thrill.

I told him that when he was ready, I'd still really like to suck him off. He told me to get dressed and leave the booth, but to keep an eye on it when people entered. He said I would know what to do when the time came.

Not really knowing what I was in for but certainly intrigued, I dressed and exited the booth. I was enjoying the fact that I had just checked another first of the list, of fucking a guy through the hole.

I got a soda from the vending machine and was wondering how in the hell I was going to kill time. I was enough of a regular that most of the guys that worked the counter knew me by sight and I could probably have gotten away with just loitering in the hallway, but as I thought about it, that might scare guys off.

Fortunately, the guy on the counter this night was someone I had talked with previously. Hanging out with him was fine and I could see the doors to both booths.

We stood there just talking about anything that popped up while I tried to not make it too obvious that I was watching for something to happen. I didn't want him to ask me what I was waiting around for because, frankly, I didn't know.

A couple of guys went down the hallway, but didn't go into the booth I had been in. It took a while, but a guy came out of the hallway on the other side of the store and went down the one I was watching. On his way out, he pulled open the door, looked in, and entered what had been my booth.

So, now I'm waiting for something that will tell me what to do next, but what the hell is it? Fortunately, it didn't take long to find out.

Pretty soon, the door to my old booth opened and the guy peeked out into the hall. I quickly turned away from the direction of the hallway so he wouldn't catch me watching him. I waited just long enough before turning around to see him entering the booth next to mine.

Bingo! This was my signal to go back to the booth. My cock immediately got hard at the thought of watching two guys through the glory hole. This was something I had hoped I would luck up on one day, but never had. Being both and exhibitionist and a voyeur, I was incredibly excited.

Again, not wanting to be too obvious, (not sure why), I continued to make small talk with the counter guy until a customer came in needing tokens. This was my opportunity to make a break and I went straight to the booth.

I slipped in quietly, not letting the door slam or anything like that. Even though it was obvious putting on a show was OK with my recently fucked friend, this new guy might have other ideas.

I slowly and quietly locked the door and eased towards the hole. Remember, this place had wooden floors that would creak and make all kinds of noise.

When I got where I could see through the hole, what a sight! I had waited long enough for the new guy to get really worked up. He was naked, on his knees giving what looked like an enthusiastic blow job. At first glance this was exciting, and I began to strip. By the time I was naked I got a little worried he might make my new friend cum and I would get cheated out of a load.

I went back to looking through the hole, stroking my cock and enjoying the show. The guy I had just fucked tapped the new guy on the shoulder and motioned for him to stand. He then reached down and grabbed the new guy's hard cock, about seven inches and slender. He said something in the new guy's ear which was probably asking to be fucked.

He then turned around and bent over, grabbing his ass cheeks and spreading them wide. The next guy starts sliding his hard cock up and down the other guys crack. The other guy must have had lube sitting on the chair because the new guy reached down and picked it up from a place I couldn't see. He smeared it on his cock and up and down the other guys ass, even sliding a couple of fingers in.

I had a great view as he positioned the head of his cock at the other guy's hole and pressed forward. He was going slow, as if he was afraid that he was going to hurt him. It was all I could do not to reach through, tap the guy's leg and tell him to pound away because this guy can take it.

The other guy must have let him know because soon he was buried in his ass. He held it there for a bit, then began pumping in and out, going faster with each thrust. This was the hottest thing I've ever seen in person and my cock was so hard it ached. I was stroking slow, doing my best not to cum. I really wanted to wait to do that when the new guy filled the other guy's ass with his load.

I watched and stroked as the fucking continued for a few minutes. I heard the new guy ask where he should cum. I didn't hear the reply, but since he kept pounding the answer was obvious.

The new guy pumped fast for the next few strokes, then slowed way down. This is difficult to pull off, but I love it when I can slow down at just the right time before cumming. Cumming while thrusting slowly is a great sensation and I guessed that was what this guy was trying to do.

After three or four slow thrusts he slammed it home, pulled hard on the other guys waist, arched his back and unloaded. He'd pull back just a little and slam in again, and again. It must have been quite a load.

I was kneeling to be able to look through the hole and when the guy pulled his cock from the other guy's ass he turned towards the hole. The sight of that semi-hard cock dripping cum from the tip sent me over the edge an I blew my load on the wall and floor in front of me.

I crawled up into the chair and rubbed the cum that I had gathered in my hand all over my cock, which stayed hard for quite a while. I just sat there for a while not paying attention to much of anything enjoying the feeling of checking another item off the list of watching sex through the hole.

The slamming of the door to the next booth brought me out of my dazed state. As I was moving towards the hole to make sure by new fuck buddy was still there, his cock came through the hole. At last, was going to get to suck it.

I knew if this guy really had not cum through two serious fuckings he had to be ready and may not last long. That didn't really matter to me because the cum is always the best part.

I licked all over the head, tonguing the slit and running it along the bottom of his shaft. I wrapped my lips around the head and took it into my mouth. I tried to ease the rest of his cock into my mouth, but I just couldn't make myself slow down.

I was sucking at what I thought was an aggressive pace when he started thrusting his hips. I sped up, and so did he. Eventually, I stopped and just let him fuck my mouth. This did the trick and soon he slowed. He pulled all the way out of my mouth and let the first blast hit my lips. I opened wide and he stuck the head in, filling my mouth with a very hot, sticky wad of cum.

As he slowed and then stopped cumming, I swallowed his cum and continued making love to his cock. I hadn't wanted this to ever end, but now I was sure it was about to. I sucked, licked and cleaned his cock for as long as he would let me. Finally, he withdrew and pulled back through the hole.

I must have done a pretty good job cleaning him off because he pulled on his pants without any wiping off or anything. I was looking at him through the hole as he left. He turned, gave me a thumbs up and out the door he went. I got dressed and did the same. It had been a very good night.

tommydntx
tommydntx
45 Followers
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AnonymousAnonymous4 months ago

Mmmm........reading these makes me want to relive my hot, gay whoring days in the 90's, I'd use any excuse to get away from my wife to suck some cock and/or get fucked in my tight, shaved, slutty asspussy! Hope our friend gets it in the ass soon!

CuriousPeteCuriousPeteover 3 years ago

Very Hot!! Enjoyed it. And as I've said before, that it is supposed to be true makes it all the hotter. Keep going.

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