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A Booty Call for Every City

BearLover1694

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Alright, so I found some free time, and just dove in writing my next story. Another one that I'm writing as I go. I already like the way it's starting, so I hope you guys read it and enjoy too!

Chapter 1:

As spring rolled around once more, another full season's traveling schedule began. My name is Nick and I worked as the assistant to the manager of my home city's MLB team. I really liked the job itself, but there were also a good handful of qualities I didn't like. The travel got old fast, and being an in the closet gay guy at 48 years old being around a traveling boys club locker room all the time wasn't exactly how I wanted to spend my time usually. But, alas, I loved the job itself, and although they were a bunch of obnoxious jocks sometimes, getting to see a bunch of youthful men in their prime wrapped in just towels and what not certainly wasn't something I'd hated.

Anyway, the new season was starting so I began preparing myself for the travel schedule. Our first series of games was out of town, of course just my luck. I had managed to go all this time in my life without raising any suspicion to my sexuality, and a large reason for that was actually my job. To people in my family/friend circle, my job took up so much of my time and it moved me all around that my life was too unpredictable for a relationship. To my work acquaintances, I told them I was divorced because of the toll of a strenuous travel schedule. It was perfect.

My sex life was nothing to be ashamed about however. I got laid usually a few times a week. I had been on the same job for a long while and thus had over time built up some regular contacts for booty calls in basically each city I traveled to. And if that failed, there was always craigslist or a hookup site. My only drawback was that usually it was hard to find my type. Being an older guy like myself, I typically attracted either other guys my age or twinky boys. Now, my type is some kind of mix. I love, cub type guys. Young is my thing for sure, I'd take an 18 year old in a heartbeat, except the only thing is that most 18 year olds are skinny little twigs. I look for the husky, thick and juicy, jock type guys. The ones that are overdeveloped for their age. Hairy is a plus but it's alright if they aren't.

The one saving grace for this first trip was that it was to Boston. Usually the Boston, blue collar type guys fit my criteria better than a lot of other areas, and needless to say my one regular fuck buddy there was hot and exactly what I like. Once we got to the hotel I checked in, showered quick and then went to the hotel bar while I texted my boy. We texted back and forth for a bit trying to set things up as I had a couple drinks with my colleagues. Luckily he was free and said he could be over in about 45min. I ordered one more drink, called it a night and went upstairs. Not long later I heard a knock at the door. I checked through the peephole, and opened up to let him in.

I think he'd gotten a little bigger since the last time I saw him. He was about 20 now, 5'8", but was beefy. He didn't have much tone, but was bulky and thick and I loved every bit of it. I think my main attraction to this type of boy was the versatility that could come along with it. You could either have a power bottom with a thick ass that could take it like a man, or you could have an alpha jock type that can fuck you like a machine with all that young energy. This boy, this boy was the first type I described.

He walked in and took his shirt off and kicked off his shoes and socks. He started to undo his pants but before he could I pushed on the top of his head so he could get down on his knees. I was your run of the mill hunky businessman. At 48 I had salt n pepper hair, I stood at 6'0" tall, and some permanent scruff/stubble. My body was a little harder to describe perfectly in words. Basically, I filled out all of my clothes in every area. I worked out usually 3-4 times a week, but I wasn't a physical masterpiece, it was really just to maintain my body and keep from getting out of shape. Other than that, I'd say I was a fairly hairy individual. I groomed it on the back just because I don't like that, but on the front I just let it grow, I liked being the hairy, manly man that boys lusted over.

Now that I had the boy on his knees in front of me, I unzipped the fly of my pants, reached in and through my briefs and pulled out my cock and balls. My package was just overall moderate but impressive. I suppose like the rest of me, and just like the rest of me it was filled out. I was probably 7.5" and cut, and my balls were not necessarily bull balls but they were plump and round. I proceeded to thrust forward so that the boy would take my cock in his mouth. I liked to start by facefucking my boys so I held his head still with both of my hands and just humped forward and back as my cock slipped in and out of his wet mouth.

After a little while, I let the boy do the work as I started to unbutton my shirt and undo my tie. I took them off, and then unbuttoned my pants and slid them down to my ankles along with my briefs. I saw the boy look up to me, taking in the sight of the grown man above him. He ran his hands up my body to my chest and just groped at my meaty pecs with his hands. I stood him up and planted him with a kiss as I unbuttoned his pants and he slipped them off. He was wearing bright red, very tight briefs. The bulge in front showed his visible full hard on, and I turned him around to get a full view of his big ass.

I sat down on the edge of the bed and bent him over my legs. I gave him some gentle slaps (I'm not big into any real spanking/kink/pain play but some mild slapping is hot) and massaged his butt through his briefs. After a little while I slid his briefs off and his bare ass was mine. I moved him off of my legs and onto the bed as I got up to grab a condom. I loved fucking bare, but the lifestyle I live, I fuck enough different people that condoms are practically necessary. I rolled one on to my throbbing cock and positioned myself behind him. He was laying flat on his stomach, so I put one leg on the outside of each of one of his and slowly squeezed my dick in. God this boy was tight.

I knew both from the past, and from the boy's reactions to my behavior tonight he liked being controlled somewhat. So, being behind him and kneeling over, I decided that my method of balance would be to take both of my hands and just put my weight on his upper back, pinning him down on the process. I started ramming into my boy's ass hard now and by his moans I could tell he loved it. I flipped him over and entered his ass again, in missionary position this time. I leaned over and kissed him once then straightened back up in order to get a nice fast rhythm going. I took my boy's cock in one hand and slowly stroked him. Not long after I had him begging me to keep going and moaning as he busted his nut all over his body and the bed.

"Where do you want my cum boy??" I asked him as I pulled out and ripped the condom off. "I want you to cum all over my chest please." the boy said, his eyes grown big looking up at me. I jerked my cock as he massaged my body while I knelt beside him. I felt it starting at my shaft, and the warm feeling spread throughout my body as my cock exploded. The boy was covered in both our cum. He stayed there as I went and got a towel. I got on the bed beside him, and kissed him as I wiped his body. "Alright boy, I think it's time to go." I said as I got up and slipped my briefs back on. He got up and got dressed.

"I doubt you're here for long, but next time you're in town hit me up again, I'll be more than happy to help you out again." the boy said on his way out the door. The next morning I was on my way to the next town, hoping the remainder of the season would be even half of last night's grand opening.

============================

If any of you guys liked this start, but haven't read either of my last two stories I'm posting their links here

My Former Teacher:
http://www.justusboys.com/forum/threads/437349-My-Former-Teacher

So Wrong, But So Right:
http://www.justusboys.com/forum/threads/437950-So-Wrong-But-So-Right
 
That's a great start, BL. I can see we have a hot and horny man, just like the sailors...a guy in every port... I know this will be very interesting as he arrives at each city.

Craiger
 
What a lot of fun to read. I look forward to a hot summer with a lot of adventures with hot guys!
 
BL,
You've certainly got me wishing your young, bean town stud was in my bed at the moment.

Nice start - can't wait for the CUMming attractions.
 
Thanks guys! The next chapter should be up at some point today. Likely later this morning or in the early afternoon
 
Took me longer than I thought to get this one done, but alas here's chapter 2. Enjoy.

Chapter 2:

The next stop was Miami. When we arrived, instead of going to the bar after showering, I decided to just go to sleep, and I'd try and find a guy to hook up with for the next night or the night after maybe. I woke up the next morning and immediately went onto craigslist and logged onto the hookup site I used to try and find a fuck buddy asap. I usually only post Craigslist ads if I'm super desperate, but I just reply to ads. None jumped out to me as my type of boy so I was heavily relying on the hookup site. There were always tons of users online, even a good bunch that matched my preference, but unfortunately many were either phonies or totally not serious about following through.

I messaged a few guys but none really seemed totally willing to meet. So, I went downstairs and went for a run on the hotel treadmill to kill some time. Much to my pleasure, when I wrapped up I had a message from a boy in the area. We messaged back and forth and decided for him to come to my room around 11:30 that night once my workday and the game at night had ended. I was really excited, he was a Cuban boy, 23yrs old and decently muscular. Even that was kind of pushing it for how I like my boys, I don't like too much definition or the body builder type, but it was mainly just his pecs that were really built, and I love a hot chest so it was alright with me.

The game went a full nine innings, but for a good few innings it was tied so I was praying we didn't go to extra innings. Luckily the tie was broken and we all moved on with our lives. Even though it went normal time, I was still running a little late getting back so I rushed to the hotel alone instead of going with any coworkers like usual. I made it back before him, showered up and was just getting out when I heard a knock at the door. I went and let him in, and he was hot!! He was wearing a tight tshirt, it was tight overall but it really strained over his chest. "Come on in." I said softly to him as I stood there wrapped in my towel. He did as I said and as I closed the door he loosened the towel so it dropped to the floor and I just stood there exposed.

"Just seeing what I have to work with here." he said. He had such a cute voice. Deep, but soft. He had a thick accent and I could tell he spoke softly because he was unsure of his English. His eyes scanned up and down my body taking in my large frame and slightly above average endowment. "Can you turn around fast?" he asked me politely. I did as he asked. Well, I guess I should explain. In our online talking he said that he likes to decide once he's met the guy whether he wants to top or bottom. So I think this was him making his choice. "God man I don't know..." he said conflicted. "Well, I think then it's only fair if I get to see you and maybe I can decide." I said as I went over and kissed him, moving my hand to his pants. He grabbed my hand before I could do so and pushed it away.

"I chose, I'm going to fuck you papi." he gently let out. I lead him over to the bed, I stood behind him and wrapped my arms around him rubbing his body as I kissed his neck. "You have a beautiful chest boy. Time to get this shirt off so I can see better." I said as I lifted his shirt over his head. He was no exception to typical Cuban hairiness which was not a problem to me. I went for his pants to finally get a glimpse of what the boy would be ramming me with. I dropped both his pants and briefs to the floor and out flopped the most magnificently long, and fat looking uncut cock. Wow, like seriously, I was amazed. Like 9.5" and I'm not one of those to overplay the size.

"Wow, that's an impressive cock boy. Why don't you lay on your back and I'll work it over with my mouth a bit." I said as I turned him around. "Oh no papi. I have penis that is very sensitive. I won't last long in your tight ass even without being blown." my boy explained to me as he instead maneuvered me around and put me on all fours on the bed. I could hear him stroking off as I simultaneously felt his tongue on my hole. He wasn't totally wrong to assume I'd need to be loosened a little, it had been awhile since I'd been fucked so I'd be a tight squeeze for any normal man let alone his big cock. After he licked and fingered my ass to get me ready I heard him rip open a condom wrapper and apply it to his prick.

Before he could enter me I told him I wanted to be able to adorn his chest so I flipped on my back instead. Now in position he slowly but surely started pushing into me. I started making loud moans. "Sssshhhh ssshhh sh. It's ok papi, I won't go all the way til you're ready. You'll get used to it don't worry." he whispered in my ears before he kissed me. I felt up his chest and God was I in heaven. This furry muscle bound Cuban boy with a nearly ten inch dick was treating me so well as he was mounted over me. I had one hand on his chest and the other was on his waist in case I had to push him back if he went in further than I could take.

I will give him credit, he was huge but he knew how to use every inch. It wasn't long before he was balls deep and it felt amazing. I told him he could just pound it out and he had no hesitation as he started just really fucking away. He kneeled back straight and started jacking me off and, and with that and the sight of his pec flexing and bouncing up and down as he jerked my cock I was already close to cumming. "Ohh fuck you've got me close don't stop boy. Use that hole. Oh yeah here I cum!" I moaned as I shot all over my hairy body. Soon after he let out some muffled moans but just kept on fucking me, but I could feel every inch of his cock throbbing inside of me as he filled up the condom. He pulled out of me slowly, took off the condom and leaned down to kiss me, his somewhat sweaty and furry chest resting on mine.

He got up and started to change and I just slipped my briefs on. "Thank you papi, call me next time you come to Miami." he said in his adorable accent as he stepped out the door. I went to bed that night with a slightly sore ass, completely satisfied, and hopefully a new regular hookup in Miami. Overall a good trip I'd say.
 
BL,
I really enjoyed "our" encounter of the Cubano kind.
 
Exciting, Miami treated him well. Nothing like a sexy Cuban man. Will his next encounter be as nice??? Thank, BL.

Craiger
 
Hey guys, sorry I've been away and busy since Thursday afternoon so haven't gotten the chance to really breathe let alone write. New chapter should be coming tomorrow or Monday latest
 
Hello, guapo. Is that a plátano in your pocket or are you happy to see me ?

What a fun post. Can't wait to see where we go next.
 
Chapter 3:

After two series on the road, we finally were back home in Chicago for a bit. I always had mixed feelings about being home. In one hand it was nice to not have to live out of a suitcase for a little while, but on the other hand I kind of liked the anonymity and promiscuity that my travel schedule allowed me to have. And as far as my sex at home goes, it's just totally regular which again, can be good or bad depending on your mood and train of thought.

I usually started looking for my type of boy online right when I arrived, the sooner I found one the sooner I could plan my sex each night during the stay at home. This particular day, I hadn't found a boy by about 4pm so I called up Jason, and he agreed to meet me that night around 8pm at my place. Jason is like my good old dependable fuck buddy. We go way back, and I mean waaayyy back. Jason was about 59 at this point, but I met him back when he was 31 and I was only 20. Jason and I met in the locker room of the gym we both went to. I'd seen him around, but somehow not really noticed how hot he was, but one random day we seemed to just not be able to stay away. The only locker when I arrived was next to his and he was just getting there, and as our workouts progressed we just kept doing the same exercises. As we were both also leaving at the same time, Jason introduced himself and invited me to his place for a party.

His party was fine, no real prospects or anything especially for a guy in the closet, but I did end up just spending a lot of time talking to Jason which I really enjoyed. This is when I really started to take notice of him. Back then I had a different type of guy, and he was it. He was tall, really dark hair with a nice amount of facial hair and stubble, a thick body with somewhat of gut/stomach but certainly not fat, and just thick features all around from his ass to his legs to his arms (which had the sexiest hairy forearms showing by the way). Back then I was a fairly lean and trim boy.

As the party went on, we just kept talking and talking. Before we knew it, the last person other than us was saying their goodbye to Jason. We were sitting on the couch, each with a cocktail and talking. All of a sudden he put his hand on my shoulder. "Nick, feel free to tell me if I'm way wrong or out of line, but I think you're really cute and it might be in my head but I feel like you've been checking me out all night too. I think I've had just the right amount of drinks to risk making my move too, because I'm not usually so forward." Jason said. I didn't really know what to do. I had never really done anything with a guy, let alone one so hot as Jason or even been hit on like that before. I was nervous so I started to grab his arm to take his hand off of my shoulder but just the feeling of his thick hairy forearm in my hand made me freeze and I just gazed into his eyes.

Flash forward back to today 20 some odd years later, and Jason was coming over. I'll spare the details of the first night since I don't want to spoil any of our moves that we use today but I'll summarize our relationship. We did have some great sex that night after his party, and essentially since then have just became best friends who also fuck on the side. I tell him about everyone I fuck and so does he and we couldn't be any more comfortable with that or better friends in general throughout the years.

The doorbell rang and Jason came in. We hugged and exchanged pleasantries, and we sat down with a glass of wine. I told him all about my regular boy toy from Boston and then about my new Cuban stud from Miami and he told me he hadn't fucked anyone since the last time I had gone to his place a couple weeks ago. We continued talking for a bit and then took things to the bedroom. Jason was a total top, and since my days as a boy he was the one daddy I always stayed attracted to even though I now tended to like the jock boys these days, so I've just always loved bottoming for him for the last 28 years.

As I began to undress Jason and he did the same to me we got into bed totally naked, and I really realized how Jason really aged like a fine wine. He went from a thick young thirties stud, to now being perhaps just a tad bigger all around, a little hairier, and what really got my dick hard was that he now had salt n pepper hair, he was just such a hot rugged man with now even more experience, so I would be a fool not to be his bottom for as long as he still wanted me to. I had Jason lay back and I got on top of him. I started kissing him, then began making my way down his masculine hairy body. He had a piercing on his right nipple which I always paid a little extra attention to. By the time I made it down to his penis he was hard as a rock and man was it a great welcome home sight.

Three general words, long, fat, and cut. Jason was about 8" and really fucking thick. Like beer can thick, and on top of that he was cut and just had the most amazing mushroom head. I just began sucking away like I had done so many times before. Jason's balls were really sensitive so instead of licking and sucking those like I would for other guys, I just cupped and gently massaged them with one hand like I always do. I eventually came back up for air and went back up to his face to kiss him. He pulled me up a little farther, and popped his dick into my hole.

Jason was the only man I've ever fucked raw, and ever since we became extremely close friends with benefits he played safe with others too. He just started humping away when he got inside of me. I let out a series of moans as his thick cock stretched out my ass. I was in heaven. Don't get me wrong, the Cuban boy was huge and he fucked me really good, but there was just something about the sex Jason and I had that was on another level. Jason rolled over after awhile so he was in between my legs and I was on my back. He kept fucking me like that for awhile as I rubbed his hairy body. Finally, Jason pulled out and shifted around me so that we were both on our sides and he was behind me. He lifted one of my legs in the air and pushed back into me. He always said that this position felt best for him, and I certainly had no problems with his hairy body against mine and his magnificent tool inside of me.

Jason started stroking my cock as he thrust in and out of my ass. It wasn't long before he was groaning out loud and burying his cock deep as he breeder my hole. The feeling of his body shuddering behind me, and his cock inside me sent me over the edge and my cock pulsed in his hand as I shot my load onto the bed. We fell asleep like that. He was the only man I ever let spend the night too, because I knew he wasn't going to wake up attached. We hugged as he left the next morning and I continued searching for a boy toy in Chicago over my morning coffee.
 
Always nice to have a plan B, particularly a good friend to back you up. Sometimes it's nice to just sit back, knowing how things will go and partake in some hot and heavy. Also knowing that the attraction is purely friendship and sex. Thanks BL.

Craiger
 
I decided that since I took so long between Chapters 2 and 3, I'd give a little extra and pump out Chapter 4 today as well.
Chapter 3 was kind of meant to build a little more character to Nick, but Chapter 4 is right back on track with more of his traveling sex adventures. Enjoy!

Chapter 4:

My short time home quickly came to an end and I didn't find a boy to fuck, either as a regular thing or a one night lay. As the years have passed I've found myself thinking in my head that I probably didn't have a regular fuckboy in Chicago because of Jason. I don't mean I was in love with him or wanted to be exclusive or anything, but just knowing he was in the area I think I subconsciously found looked to find something wrong with anyone else. Whatever, on to the next city.

The next team we faced was located in New York, which was always a place I looked forward to visiting. I always seemed to get lucky more than once on my few day trips. I had a regular bottom boy that I usually met up with once, and then I typically managed to find one other boy for a one night stand. I've decided over the years it's just because it's so populated, and it's a common travel place so my odds are just greater in general.

We got to New York and I checked in at the hotel. Before I jumped in the shower I texted my regular boy so I had an idea which of the following two nights he would be free, after my travels I was kind of tired even though it wasn't a long trip so I decided I'd probably just chill and sleep for the night. I had a few texts back once I got out of the shower saying he was out of town both of the next nights but would be able to do tonight in like 30 minutes. I told him that I was exhausted so the only way I saw it happening was if he did all of the work. I was half joking, but I got a quick reply back saying that was fine and that he thought my cock was worth the extra effort.

I decided to just stay in my towel since he would be at my room shortly, and in even less than a half an hour there was already a knock at the door. I opened and in he came, he rushed in and I closed the door behind him ready to get it on. My little Italian New York boy was shorter than my usual at only 5'5" but he made up for it with his body, and the fact that he was like a little ball of energy that could just keep going and he was also flexible so I've fucked him in some precarious positions in the past. He was in really good shape, but wasn't toned so he was just bulging and tight all around. He had a slight six pack forming but it wasn't on a thin or lean body so it was right up my alley. But his best feature was yet to come.

He was wearing pretty loose and casual clothes so he got right to undressing. Flip flops that he quickly kicked off. He slipped down gym shorts and kicked those to the side, and lastly he pulled off his tank top and threw that to the pile that had formed. Now he was stripped down to just a jockstrap. I wanted to get to my favorite part of this little muscular bundle of joy, so I turned him around and got down on my knees as he pushed his hips back and put his hands and chest against the wall. I was face to face with this beautiful bubble butt. If this boy's ass wasn't the world's perfect ass, then it was probably second place. So round, so tight, so perky, and although it wasn't usually my thing he kept it totally smooth which for some reason really sends me over the edge with a tight little ass like this. Today it looked even better since the straps of the jockstrap just rested underneath each cheek accentuating just how marvelous it was.

I wasted no more time and I just dove in. I spread his cheeks apart, one in each hand, and put my mouth right on his hole. He moaned out as I slid my tongue all over his pink pucker. I must've continued for almost ten minutes like this, making sure to squeeze each beautiful cushion in my hands continuously throughout. I got up and stood behind him pressing my hairy chest against his back, and I had removed the towel so the bottom of my shaft was against his hole as I thrusted sliding it up and down to tease him. I wasn't totally hard yet though, and he could tell. He turned himself around and jumped up, wrapping his arms around my neck, his legs around my waist, and I grabbed on to his ass (half to help keep him up and half just because I loved touching his bubble butt). I walked over and sat on the edge of the bed, we didn't stop kissing the whole time. He leaned me back and knelt on the floor between my legs which were over the end of the bed and my feet on the floor.

He slowly and gently started sucking my dick, and once it was nice and wet he totally just stopped sucking it. I began to lift my head to see what he was doing when I felt his hand grab my shaft, and then he put his mouth on my nuts. He started massaging my cock in his hand, vibrating it fast which felt good, but he really went to town on my balls which felt even better. I honestly don't think I've ever felt anything like that before. He alternated which of my balls was in his mouth, at one point had them both in his mouth and was just juggling them around with his tongue, and periodically was just rapidly licking my sack. "Holy shit that's amazing." I managed to sigh out in pure bliss. Eventually that ended and I heard him reach for a condom, and then I felt him slip it onto my now fully hard cock.

He stood up and got on the bed to straddle over me, about to ride my dick. "Take your jock off so I can stroke you off boy." I told him before he put me inside himself. "Nope. You're exhausted daddy, this is all about you tonight. Lay back and just enjoy the way my ass feels on your dick." he said as he reached around to position my cock at his hole. He made the cutest little wince of pain as I slowly entered him, once the head was in and he got used to my girth he slid all the way down to my balls. I put my hands on his hips as he started to rock back and forth on my cock, it really did feel great just laying back while I watched and felt this boy using his ass to please me. I moved my hands to his globe-like ass cheeks and just held them in my hands. He put his hands on my chest for support now and started going up and down on my prick now. "Oh you're getting me close now boy. Fuck that feels good." I groaned. He dismounted from my cock.

"Time to switch positions before you blow then. Hope you enjoy the view this time." he said as he turned around facing his back to me. He put my dick back in his ass. And the view really was amazing, first watching my cock get swallowed by these big round cheeks and then just the sight of his ass grinding back and forth and jiggling up and down on my cock was so hot. I put my hands behind my head and just watched as he worked my dick over. It wasn't long now before I was close again. "You're getting me close again boy, if you want my load anywhere specific you better stop now and finish me off how you want it." I warned him right when I started getting that feeling where you know it won't be long but it's not too late to switch around before you nut. He just kept going and going. As much as I tried to hold off it just built more and more and before long I was blasting my load inside of the condom in his ass and he just kept going. The feeling of his tight warm ass on my sensitive cock just kept milking more out. By the time he slid off of my cock, it just flopped onto my stomach still full length just limp and surrounded in my semen inside the condom.

My New York boy leaned in and gave me a kiss to end things off. I slapped his ass as he got up, and I took the condom off as he got changed. "Thanks boy, you were amazing tonight. Next time hopefully I won't be as tired and I can repay the favor and let you relax as I do all the work on that gorgeous ass of yours." I told him. He said that sounded nice as he left out the door. I stayed naked in bed, slipped under the covers and got one of the best nights of sleep I've ever had.
 
Your latest story is another winner! Thanks for sharing it with us:=D: :=D: :=D: :=D: :=D:
 
Ok so even though I posted two chapters within a few hours yesterday to redeem my procrastination prior to that, I've decided to try and get back on the schedule of posting one each morning/afternoon. So here's the next installment!

Chapter 5:

I woke up the next morning feeling well rested and just overall great. I went on to my hookup site and craigslist to try and find a boy for either of the next nights. On the hookup site I mainly just found really twink type boys, and typical craigslist was largely a bust. I did come across one ad though, it was for a boy who just turned 18, wanted a manly man to be the first to fuck his hole, and said he was a jock body type. We talked and were really both into the idea of meeting up. Only a couple of times in my life have I taken a boys virginity and I was dying to do it again.

I sent him a couple of pics and he said I was exactly what he was looking for, an experienced manly daddy type. I was hard as a rock just talking to him. Then he sent me his pic....he either lied in his ad or was totally delusional when it comes to how he sees himself because he was all skin and bones. I ended that conversation and went on with my day. Gym, shower, and off to work. It ended up being one of my coworker's birthday so instead of finding a boy for the night I just went to the dinner/drinks party and went home afterward. The next day ended up just about the same, except for the birthday stuff, so after the work day I just decided to go to a bar in the city. I usually went to hotel bars because they were quiet so I could have a few drinks in peace, but in New York at least at my hotel that wasn't the case so I had found a bar that was typically pretty quiet.

It was really right around the corner so no cab ride even, it was really perfect. I got to the bar, sat down and ordered my whiskey neat. There were only three other customers there, a couple in a booth, and an extremely young looking boy a few seats down from me at the bar. He got up to go to the bathroom, and when he got back the bartender was over in my area making me my next drink so the kid sat next to me, I thought it was a little weird but didn't think much of it. I was starting to get a little drunk after a little while and was starting to get in a bit of a bitter/angry mood, about how I was 48 and alone, that my family didn't know the real me, and that I'd been in the same job that prevented me from putting down roots for years.

"You here on business??" the boy said. I thought I had noticed him making eyes at me but between my buzz and my anti-social nature I hadn't cared really. I nodded slightly hoping he would get the hint and just shut up, but he had other plans. "Well you know, there are some really interesting things you can do here in the city..." he said flirtatiously as he put his hand on my thigh discretely. I gulped down the rest of my drink and stood up as his hand slid off my leg. "Well lets go then." I said motioning for him to follow me, my voice gets very raspy and deep when I drink which I think made him find me even hotter. He followed me out the door, and I admit I didn't really plan it through so I ended up just leading the way down a back alley.

"What do you li..." the boy started to say before I put my hands on his shoulders and pushed him to his knees. I was drunk and a little pissed off from the drinking so I was just going to use this boy for a rough fuck to let some stress and anger out. He actually was exactly my type. He had brown hair, had some meat on his bones, and was young. He went ahead and unzipped my pants and before I know it my cock was in his mouth, I just leaned back against the wall behind me and enjoyed. Due to the booze it took me a little while to get it up, but when I did I was just totally ready to drill this boy's brains out. I grabbed his head with both of my hands and started fucking his face. It felt great, so warm and wet, and just the noise of him choking on my member was hot.

I lifted him to his feet and turned him around so he faced the wall as I slipped his shorts off all the way and threw them to the ground, he had no underwear on. I took a condom out of my back pocket and made quick work putting it on and just rammed right into him, I've learned over the years to just always have a rubber on me just in case. I undid my tie as I fucked him and stuffed it into his mouth for now to muffle his moans. Now I put my hands on his hips and just fucked away. I humped this boy fast and hard, meanwhile I stroked his cock. His muffled moans intensified and his ass squeezed tight around my penis as he shot his load down to the ground.

I turned him around and he took the tie out of his mouth and slung it back around my neck. Now I lifted the boy up, lowered him onto my cock and pinned him against the wall. He unbuttoned the top few buttons of my dress shirt and played with my chest, I could tell he was into the daddy/boy type relationship because he loved my masculine features (fat cock, hairy chest, stubble, strength). I started fucking him hard again now against the wall. The boy started moaning loudly again and trying to talk dirty, but I just wanted to get off and wasn't in the mood to hear him talk and moan like a bitch so I just took one hand and covered his mouth and pounded his hole even harder now.

Being in the alley, dominating this boy, I was getting close now. "Get on your fucking knees boy." I commanded him as I pulled out. He did as I said and I ripped the condom jacked off until I shot a big load right on his face. I stuffed my slowly softening cock back into the fly of my pants, zipped back up and left the boy in the alley still with his shorts off and covered in my jizz, and went to the hotel to get some sleep before my travel the next day.
 
I don't derive any pleasure from treating people this roughly, and I certainly don't like to be on the receiving end... the fact that I get a little shiver of excitement reading about it probably says something about me that I don't want to think about too deeply!

Thanks for brightening up an otherwise dismal Tuesday evening!
 
Rough and humiliating sex seems to thrill some, however I'm too much of a romantic to participate in it's practice. Always though, to each his own. Thanks, BL.

Craiger
 
Here's the next installment. I honestly couldn't agree more with you guys' feelings on the roughness/dominance. Every once in awhile I find myself a little bit intrigued by it but not to the point where I'd condone it myself.

But anyway, I think after Nick was in a bad place doing that last chapter he redeems himself now. Enjoy!

Chapter 6:

I had a decently long layover on my way to Seattle, and still kind of felt like shit so I decided to just go and sit with a cup of coffee and start browsing online for a boy, because why not right? Also we were there really for only one night, I was going to be exhausted and nursing a hangover tonight when we arrived, the first day was just a single game, then the second day was an early game and we left later that same day so the earlier I start looking for a boy the better. Seattle was kind of peculiar because there was really no specific type that was common there so there was a little bit of everything when I searched.

I found one that I liked and sent him a message. He was 5'9" 19 years old, brown hair and a rugby player type build, so muscular/stocky but not lean by any means. His profile said he was looking to be shown the ropes so I figured who better to do that than me. He answered me back pretty quickly and said he was excited by my profile and would definitely meet me at my room the next night. Well that was pretty easy. A couple of long hours and ibuprofen tablets later and I was finally on a plane to Seattle. The whole layover and plane ride after I found the boy, I couldn't stop feeling a little bad for how I treated the New York boy. Don't get me wrong, it wasn't rape or anything like that, he liked the sex, and it felt good for us both, but I'm just not usually one to take the dominant/rough sex to that level. I never treat the other person like some form of object and for that I felt bad. But I suppose it was over now and I had to move forward.

We touched down and surprise surprise, rain!! In part of my mind I can see the slight charm of the frequent rain in Seattle but for the most part I really hate it. I got to my hotel room and just opted to go right to sleep. My headache was mostly gone but I decided the extra sleep couldn't hurt anyway. I think the rain threw me off because I slept through my alarm that morning and had to skip my morning workout. I had a text from the boy I messaged the day before reaffirming a time, so I told him 9:30 should be good. I showered and put my suit on as I went to meet up with my colleagues for work for the day. It really could not have gone any slower, and the fact that I couldn't stop thinking about all the things I'd do with this young boy certainly didn't help.

Finally the game ended, I wrapped up my work for the day, and I was back at my hotel at 8:15. I texted the boy and told him I was there already, and was going to shower then anytime after 15min from then would be fine. I showered quick, because I was excited for what was to come, it had been two days since I fucked the guy in the alley so I was more than ready to go. I got out of the shower and saw a message that said he was so excited for tonight that he was already downstairs in the lobby and I could just text him when I'm ready. I did just that, and in no time he was at my door.

I had slipped on a pair of briefs. I knew that it was either his first time, or at least one of his first few so I wanted him to enjoy the pace and not just rush through everything. Plus, when I was around his age I loved playing with and admiring older guys in their underwear showing off their hot daddy packages for a bit before getting down to it. From the fact that he couldn't take his eyes off of the bulge in my briefs I could tell I made a good choice. I kissed him on the cheek as I closed the door. "Come on in, why don't you strip down to your briefs and we can get started." I suggested and in the blink of an eye all of his clothes were off. I led him to the bed and we both just laid there next to each other, I could sense how nervous he was.

"How many times have you been with another guy before?" I asked him as I got onto my side facing him and gently stroking his hair to calm him down a little. "This is my first time." he admitted. "That's what I kind of thought. Well I'm going to make this as good for you as possible. I'll go slow and teach you as we go. But I'll still be a little bit of your dominant daddy type. I'm going to take charge and tell you what I'm doing as I do it, but you have to tell me if it's something you're uncomfortable with or you don't want to do ok??" I told him trying to make him as comfortable with everything as possible. "Here's how we'll do this. Except for kissing because we do that at the same time, and fucking because I'm just going to top you, everything else we do, I'm going to do first to show you and then you're going to copy me ok?" I asked and he gave me a slight nod. With that it was time to take this boy's cherry.

I leaned over and kissed him gently and passionately before making my way to licking and nibbling on his nipples. I then shifted to my back and gestured for him to do the same on me. I think he was hesitant because of the hairiness of my chest but as he got used to it I'm pretty sure he liked it. It became apparent that he liked my furry body as he began running his fingers through the hair on my chest, abs, and forearms. I pulled him so that now he was straddling my waist, and I reached up and pulled his head down so we could make out some more. My cock was pretty stiff in my briefs now so I positioned him cuddled next to me so we were side by side on our backs. "I think it's time to finish undressing." I said as I slipped my briefs off and he did the same. He was fully hard, probably only about 5.5" and normal girth. I could tell by the look on his face as he saw my penis he was a little self-conscious.

I pulled him in tighter and kissed his forehead. Now that we were side by side in all of our glory I noticed what a stark contrast we were. I was fairly endowed and he was probably on the lower end of average. I was taller, dark and experienced while he was shorter, hairless and a virgin. I took his cock in my left hand and slowly jerked it, and told him to do the same. He hesitantly wrapped his hand around my dick and started moving up and down. "Ohhhh that's it boy. Feels good. don't stop." I said, slightly exaggerating to make him feel good and then serious at the same time as my cock really was in need of a good massage. I maneuvered myself around so that I was between his legs. "Now I'm going to show you how to suck dick boy." I stated as I took his cock and put it in my mouth.

He groaned out in pleasure. Although his cock wasn't big he did have a decent set of hangers, which needless to say I periodically took my mouth from his dick to play with them a bit. I came up and said it was his turn now and we alternated. He struggled trying to take me all the way. "It's alright boy, if you can't go all the way down just do what you can." I said softly, his warm mouth as inexperienced as it was felt good. He kept going and going "notice how I switched my attention to your balls now and then boy? That makes it feel even better so do that too." I told him now. He did as I said but was a little overzealous and really sucked them hard "Easy easy easy boy! A man's nuts are extremely sensitive so you have to be careful and gentle with them." I encouraged him. He learned quickly as he became more gentle and switched over every once in awhile from cock to balls well.

"Alrighty boy, time for the next lesson. Get on your hands and knees and stick your ass out." I told him, he knew what was coming. I slowly started eating him out which judging by the noises I heard he thoroughly enjoyed. Not long after I had him switch with me, and he was actually a really good ass eater I was shocked. I had him stop. "It's time for you to get fucked now. Get on your back." I told him sensing that he was starting to get nervous again. I reached for a condom and put it on, followed by lube which I also put on his hole.

"You've done really well so far boy. Now this is going to hurt a bit at least at first. But I want you to try it anyway. But don't worry you can tell me to stop and go back at any time." I reassured him as he nodded. I planted my lips on his and slowly pressed my head into him. I felt that ever familiar pop when it was fully inside and he froze up. I stopped and kissed him more and reached down to stroke his cock to ease his mind. It worked as he started breathing regularly again and moaning more. "That was the hard part boy. I'm going to push in more now and slowly work the rest of my cock into you." I told him. I did just that, slowly but surely my hips met his ass and I was fully inside of him.

He was extremely tight. I stayed still for a little while so he got used to it before I started slowly moving back and forth just slightly. I maybe moved an inch of my cock in and out each thrust, I figured he was tight enough for just that to get me off eventually, and it was his first time so I didn't need to fully go in and out and hurt the boy. I didn't stop my slow milking of his cock and before I knew it he was climaxing. He tensed up and shot a huge load on his body, and as his ass tightened I couldn't hold off and came as well. I collapsed over him and he was wrapping his arms and clenching onto my back as my hairy chest rested on his smooth cum coated body.

"Sorry, I wish I could've cum somewhere else for you for your first time but you just felt so good I couldn't hold off." I said to him as I pulled out and ditched the used condom. He said it was ok and I wiped him off. This is usually when I have my boys leave because I don't do overnights, but I think he didn't know what to do with himself or what was normal since it was his first time so he was just staying in bed lingering. I didn't want to seem like a douche by kicking him out after I got what I wanted especially since it could make his first time seem negative. I also think I felt like I had to do some good after how I roughly I fucked the boy when I was drunk in New York, and I think how gentle I was with this virgin and being nice to him now was me redeeming myself. So I let him spend the night and I guess it wasn't the worst thing, the sexy daddy side of me kind of enjoyed having a boy snuggled up to me through the night admiring and playing with my hairy chest and nipples.
 
Much more romantic and gentle for the boys first try. Nick better be careful though, he may get used to that comfort of having a warm body next to him through the night. I'm sure he has a new friend for his future trips to Seattle. Thanks, BL.

Craiger
 
BL,
I finally had a chance to savour your musings.

The comfort of home and his early days was great, as was the mentoring, make it special of last night.

The dark of NYC was a bit severe - intriguing, but severe.
But what do you expect from the impossible dreamer?!
 
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