Justin's Journey

The last of my college experience went as expected. I studied hard and partied with friends during the semesters, and then used my breaks at home to hookup with guys. I found that I didn’t really care for topping, I almost strictly bottomed. Always with a new guy, always at his place. It felt like I was living two lives. One life would pause while I went to live the other.

I went a total of 5 years in school and graduated in the spring with two engineering degrees. I was very proud of myself but also very excited to move away from that tiny little town. I moved back to an apartment in a neighboring suburban area to my hometown. Only about 20 minutes away from the cities big downtown area. I started my big boy job and was ready to start living my big boy life.

Being back on the gay scene permanently was a bit intimidating. I was used to only having 1-3 month spurts of trying to find the best pickings from Grindr. But now, I had time to date around. I could get a new boyfriend or something. The options were endless. Desperate to curb my cravings, I knew I needed a hookup soon to start me off. My first week at work was mostly watching training videos anyway, so I would half pay attention to them while chatting with guys.

I worked in a very corporate area. Lots of DL men looking for quick things on the side. I really liked the idea of just being a man’s quick release and nothing more. I talked with several of them to get an idea of their interests. Most were only interested in a quick blowjob in their car on a lunch break, which I didn’t care for. I wanted more. I kept a very clean palette down there and I prepped every day before work on the off chance that I’d find something during or after work.

I finally found a couple guys that I liked. The first was a guy named Matt, who had a beautiful uncut cock. He was a couple inches shorter than me, which I didn’t love but I was still willing. He was a slightly pudgy Latino man with a little bit of a belly. His only downside was that he asked if I’d recently been tested. Which is a completely fair and valid question. But I just knew that he wouldn’t want to do bareback at that point. I almost exclusively did bareback because I just loved giving a man the pleasure of shooting his seed in me. It was the hottest thing in my opinion. Assuming he wouldn’t be interested in breeding, I kept him as a backup.

The second guy was Todd. He was much older than me, maybe mid 50’s. Age doesn’t play that big of a role in my attraction to someone, I’m more interested in physique. But I love the idea of a dominant older man. Todd was also super tall. At a whopping 6’4, he had a very average build, and looked great for his age. And he had a full head of salt and pepper hair. His best feature though was his thick cock. From pictures, it was hard to get a full idea of the length, but it looked just as thick as his wrist so I was on board. Todd made it very clear from the beginning what he wanted. His only real passion in life was breeding twinks. He sent me the first message, just a few dick pics and a “Hey”. I know people complain, but I always loved the unsolicited nudes that guys sent. Gives me an idea right off the bat of what I’d be working with. And I’d know if it was worth my time or not. So I replied to him.

“Hey how’s it going?”

“Good, you looking?”

“After work, yeah for sure”

“Good. You do bb?”

“Absolutely!”

I sent pics back and he sent me a pinned location. I told him what time I could swing by and he sent a thumbs up.

After work, I drove straight there. He had messaged me saying to let myself in so I knocked and entered.

“Todd?”

“Hey”

I walked further in. The place was decently well kept, but oddly decorated with lots of antiques. I ignored it once he stood up. He was wearing a ratty tshirt and some basketball shorts with no underwear. I could clearly see his dick print through the shorts. We walked towards each other and he immediately put one hand behind my head and tilted his head down to make out with me. He reached his other hand down to start squeezing my ass. I felt his body up and down but let my hand venture to his shorts. I gave his cock a squeeze through his shorts to get a feel for the girth. I couldn’t get my whole hand around it.

He wasted no time and pulled his shorts down. I got on my knees and I was able to get a full look at it. It was the thickest dick I had ever seen, but definitely not the longest. It was only 6” long or so. I did my best to suck it. I could feel its weight in my mouth. There was so much meat despite the average length. What I loved most is that it wasn’t rock hard. I love when a dick is so thick and has so much meat on it that it’s got a little squish to it.

“Mmmm fuck yeah”

He thrusted forward and back allowing my head to stay still and my mouth to take the hits. Within minutes my jaw was in pain. I pulled my head back to take a break. He took his shirt off and then started to pull mine off. Once that was done, I took the liberty of taking my pants off. Wearing a jockstrap underneath, he began to squeeze my ass cheeks and spread them apart. He’d move one finger at a time to my exposed hole to play with it. Then suddenly he went over to the couch and sat down.

No words were said but I dropped again to my knees in front of him. I leaned over his lap and dropped a wad of spit on his tip. I tried my best to spread it down his cock with my lips. I stopped to spit in my own hand so I could reach back and lube up my hole at the same time. And after a few minutes he pulled me up on top of him. Riding on the couch is a very comfortable position when done correctly. Unfortunately, I was having a hard time getting him in. His cock was the same girth from tip to base. My hole simply wasn’t stretched enough for this. I started to put more and more of my weight down to force it in, but I felt the stress on my hole and I didn’t want to break this poor man. I continued to add handfuls of spit but I still wasn’t successful.

“God it might be too big”

“I think we should go upstairs and try”

I didn’t know what he planned to do upstairs that we couldn’t do here, but I followed him. Upstairs was only a bedroom and bathroom. On the bed, there was a towel laid down and a giant half gallon bottle of lube. I now understood.

I got on the bed on my hands and knees. With Todd’s height, I didn’t have to lower any more at all, he was at the perfect level to penetrate my hole. He added a vigorous amount of lube to himself and a generous amount to my hole as well, even using his finger to push some inside me. Then he squeezed the base of his cock with one hand and pushed hard into me. I felt his tip pop in and I gasp. He paused, allowing me to adjust to the feeling. My hole started to ache and so I just relaxed my body as much as I could. But I leaned forward to slide off him.

“You good?”

“Yeah I just need a second”

“Ok cool”

A man of few words. I felt the throbbing dissipate and I mustered up the strength to lean back again. He puts his hands on my ass in excitement. This time his head goes in a little easier and as the shaft follows, I can feel him fill me up. Like a plug, he has stretched me to the limit and not even air could slip through there. I let out a little moan and he immediately starts a rhythm.

“Fuck yes, gonna let me breed that hole, huh? Fuck you bareback till I put a load in you and fill you up”

Suddenly he had a lot to say. This man really liked the concept of breeding. His girth had me in the twilight zone. Not a prostate in the world could take this thing without stimulation. I was breathing heavy and couldn’t help letting out little whimpers. He went on for quite some time. I arched my back and rested my forehead on my crossed arms on the bed while he continued to clap against me. I could have stayed there for hours. He continued with his monologue, which I began to really enjoy as he got more degrading.

“I’ll fuck you raw you slut. Take this big dick bareback and then take my load. I’m gonna cum inside you and make you my bitch. You’ll be daddy’s little cum dump”

I loved the degradation. Feeling like a cheap whore. I knew my place.

Eventually he pulled out and laid on the bed. He didn’t have to tell me to get on top to ride him, I couldn’t wait to get him back in me. He slid right back in with ease, I was sure I must had been ripped open by that point. I started on my knees but then got up on my heels so I could really get some height and power in my bounces. Going faster and faster, I felt the burning in my legs.

“Oh fuck, oh fuck yes, you want this load? You want me to cum inside you and fill you up?”

“Yes daddy, please give me your load”

He grabbed my hips with a gorilla grip and held me down with all his force. He buried his load in me. I slid forward and his cock flopped down onto his stomach.

“Do you need me to let you out?”

He obviously didn’t care about my own climax, he was done with me. I shook my head no and walked downstairs. I put my clothes on and then got in my car. I could feel my pants getting wet with the load leaking out of me. Not having cum yet, I was still horny as hell. I decided to send Matt a message.

Matt said he was so happy to finally get a reply from me. He had been looking at my pictures and had been hard almost all day. I told him I wanted him so bad and I couldn’t wait for him to fuck me. Then I laid the bad news on him. I told him I could be there in about 15 minutes but the caveat was that my hole had already been used. He took a few minutes to reply. I drove down the street so I was out of sight of Todd’s house. Then I pulled over and stared at my phone while I reached down and played with Todd’s load in my hole. Matt finally replied.

“Do you know the guy? Are you both clean? I think I’d rather use protection just to be safe”

Not what I’d prefer, but I was willing to take him in any way he wanted. I gave him reassurance to see if I could change his mind.

“He’s an old buddy. We are both clean. Please I want to feel your raw cock inside me so bad. It looks so perfect and I want to experience it bareback”

It was mostly a lie. I had been tested pretty recently and I was clean, but I had no idea who Todd was so I couldn’t be sure of anything.

“Ugh I’m so horny for you. Fine, I’ll make an exception just this time”

I clicked on his address and put the car in drive. When I got there, I walked up to the door and he opened it to greet me.

“Hey, I’m so glad you came”

“Good me too, I’ve been thinking about you all day”

I close the door behind me, face him, and drop to my knees. I didn’t want to waste any time. I start to undo his pants and I fished out his cock. It was exactly what I pictured. Darker colored, uncut, thick, and about 8 or 9 inches. Not as thick as Todd but that was probably for the best. I was so eager I basically swallowed it.

“Holy shit that feels so good babe”

As I sucked him, I began to undo my pants, pulled out my own erect dick, and started to jack off. After only a minute or two, I stood up and he pulls me in to make out with him. I dropped my pants while wrestling tongues.

“Where’s the bedroom?”

He leads me to a room just around the corner. I get on the bed in my position, looking back at him with puppy dog eyes. He gets up on the bed behind me and rubs his thumb along my hole.

“Fuck it’s already wet”

“See, it’s all ready for you”

He slapped his dick on my ass a few times and then lined up his lance. He thrusted into me and I immediately rolled my hips essentially riding him while in doggy position.

“Oh fuck, you feel so good”

I moaned and put on a show for him.

“Oh my god you’re so hot. I’ll be your daddy and fuck you whenever you want. You won’t need that other guy”

He finally took control and pushed me forward so I was laying on my stomach. He pressed both hands on my shoulders and put the weight of his upper body on me, shoving my face into a pillow. He slammed down on my ass repeatedly. Frantically trying to catch a breath, I turned my head to the side.

“Fuck yes, fuck yes, I’m gonna cum”

He let out a big grunt as he collapsed onto me. His body slicked with sweat and his heavy breathing in my ear. I felt his cock pulse and pump. I had now been used by two men today and I was so happy with the whore I was becoming.

After he got off me, I acted like I needed to go. I didn’t care much for his conversation so I walked out to the car and drove off. On my way home, I had 8 miles of highway to cover. I put the car in cruise control, propped up my leg to have my knee take over the steering. Then I pulled my pants down to my mid thigh. Jacking off with one hand and fingering myself with the other, I felt myself arriving at a climax soon. My hole was loose and the cum was dripping down onto my seat. I let out a loud “FUCK” as I shot my load up to my chin, splattering my shirt and finally getting the release I needed after all that pounding.

Months went by and both Matt and Todd became regulars. Especially Todd. I went to see him 3 to 4 times a week and my hole took him much easier the more time he spent in there. He was so much fun and felt so good. Anytime we did a position where we could make eye contact, I’d moan and bit my lip. If he started to get close I’d give him puppy dog eyes and beg him not to cum yet. He loved that. As for Matt, he made it very clear that he preferred me clean and fresh. He loved to breed me but hated the thought of other guys doing the same. I tried to keep him first in the lineup from then on if I planned on having marathon days. And I never mentioned other guys. Whereas Todd loved to hear about the other men that bred me. I was extremely happy and satisfied with my post college career so far.

I had developed a list of other regulars. Not long, but a few that I really enjoyed. One was a couple. Dakota and Stephen. Both gym rats that had huge arms and were surprisingly sweet and fun to hangout with. I never had a high opinion of gym goers as I just assumed most of them were douche bags. But these two were good. Stephen was taller than me and had more definition in his body. Abs, beefy legs, fine blonde hair, and these beautiful bright blue eyes that just made me melt. He was kind of a ditz but it just made me admire him more. I could do missionary with him forever because he had such a beautiful face and body and he felt so good. He’s just a hot airhead that meant no harm. Dakota was shorter. He was less defined than Stephen but he was always very well dressed. He was also the smarter and more talkative one. Dark brown hair and eyes the same color. Both of them were pretty kinky, which I loved. But their biggest difference was what they were packing. Stephen had a beautiful 8” pipe that curved slightly down, just the perfect bend for going right down a throat. Dakota on the other hand had a cute little 3.5 incher. His curved up and did not have any girth to it. Like polar opposites. Needless to say, I much preferred to bottom for Stephen, while Dakota rubbed and massaged my body.

One day, I got a text from Dakota telling me that he and Stephen were splitting. He was very upset and I tried to console him. I won’t go into all the details here in this story so the short version is, I helped Dakota get through a really hard time and we became very good friends. Six months later, he and I would start dating. The relationship wasn’t good. We fought a lot and I spent most of my time trying to schedule threesomes for us because I didn’t get much pleasure from Dakota’s little prick. Dakota had a very high sex drive so he was always wanting to play but was also happy with having a third. He would always say he found it hot if I degraded him about his dick while another guy fucked me. But I eventually grew tired of it and just ended things.

I knew that wasn’t the kind of relationship I wanted. I needed to find something more passionate and less argumentative. Having been checked out of the relationship for almost the entirety of it, I texted Todd that same day.

“Hey sorry I went MIA for a while, I had a situationship but it fizzled out. Hope you’ve been well. You still down to have some fun?”

“Hey, good to hear from you. Come over”

I immediately showered, prepped, and went to get the breeding of my dreams. I thought about Todd almost every day I didn’t see him. It was so good to be his little cum dump again. I ended up seeing him every day for the next week or so. I also texted Matt and a few others. I was ready to make up for lost time.

During all of this, I was still on the search for a better, more meaningful connection. I’d still go on dates and refrain from letting it lead anywhere physical too fast. But it was very hard for me. As unethical as it was, I found myself having cravings right after a date. One guy, Michael, for example. He was so sweet and seemed like a real genuine guy. We went on a few dates but it took 3 dates before he even kissed me. By then I was ready to go all the way with him. He had invited me over to his house, he made me dinner, and then we watched a movie. We cuddled on the couch and at one point he gently touched my chin to guide my head towards his. It was a very nice kiss. And he was so handsome, I wanted to go further and explore his body. Except I wanted him to initiate it. He never did.

As I left his house that night, he said to text him when I got home. It was about 25 minutes to get home. So instead I texted Matt, who only lived 10 minutes from there. I asked if he wanted me to swing by for a quick pump and dump. This had become typical for us because I didn’t care for Matt’s conversation. Matt responded with much excitement. I drove straight to Matt’s house, keep track of the time. We went straight to the bedroom and I got to work slurping down his dick and preparing it for my hole. Then I got up on the bed per our usual routine. Matt got behind me, lubed us both up, and then thrusted into me, slamming into my ass and jolting me forward a bit. He went on and on and seemed to be taking his time. I checked my watch a few times knowing I was supposed to be “arriving home” soon. When the time came, I just got out my phone during the act.

“I made it home! Had so much fun tonight. Thanks again for dinner”

“Glad to hear it! I had fun too! You’re adorable and I can’t wait to see you again”

I almost felt butterflies from it, but at the same time I felt guilty because I literally had another man balls deep in me as I lied to him. Something must be wrong with me. I collected Matt’s load and headed home.

In the next few weeks, Michael never made any further moves than a kiss, so I let him kind of phase out. I was starting to lose hope that I’d ever find exactly what I was looking for, so I continued my work as the local cum dump, assuming that would be my livelihood for the foreseeable future. But as they say, once you stop looking for something, it was a way of just coming to you.

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Next chapter:

Charlie comes back. The first dick that I ever sucked. Could this the relationship I was hoping for? Or will it also end with disappointment?