A DILFy firefighter gets a second chance at bottoming

(This story is a sequel to ‘A college golf player learns to cum handsfree’. I didn’t want to make it Chapter 3 because this story has nothing to do with the title. I wrote it a stand-alone story, so that you didn’t have to have read the previous two chapters to enjoy this one. But if you want to learn more about the characters and the background, you might want to start with Chapter 1).

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After the 2-day fuckfest with Tyler, a closeted college student, during which I made him cum seven times while he pumped four loads out of me, I needed to burn some steam at the hotel gym. Guys are supposed to be tired after sex. When cumming, the male body releases prolactin and other hormones that make you sleepy, probably an evolutionary trait from our days as cavemen. Once he had dumped his seeds in his female, the male had fulfilled his duty and could go to sleep with the satisfaction of a job well-done. But for me, it’s the exact opposite. Sex gives me a big energy surge that I need to burn down at the gym. And the adrenaline rush from breeding Tyler’s tight little cunt and milking his balls dry produced so much energy that a workout at a tiny hotel gym would never be enough. Still, I had one of the best workouts I’ve had in a while: more reps, heavier weights, and muscles eager to be pushed beyond their point of exhaustion. My biceps were bulging after my workout, and I’d be drawing some attention when heading to the hot tub to relax my muscles after my workout.

I made my way to the swimming pool area. There were already several college students in the hot tub. A college golf tournament this coming weekend had brought 80 or so student athletes to the hotel where I was staying. The guys in the hot tub were from a different school from Tyler’s as I didn’t recognize any of his buddies. And in the hot tub was also my neighbor with whom I had that awkward encounter when he asked me about the noises coming out of my room when I was banging Tyler against our common wall. There were only five guys in the hot tub, leaving plenty of room for me to join in.

I was wearing loose basketball shorts and a tight muscle top that was showing off my bulging physique. My swollen biceps were stretching the sleeves and my hard nipples were pocking through the fabric, sticking out of my big chest. I could sense my mystery neighbor was watching me more insistently than you normally do when a guy enters the room. He was checking me out, plain and simple. But to be fair, every other guy was checking me out too. None of these college golf players had anywhere close to my muscle mass. They all looked like they were twinky freshmen whose balls had just dropped a handful of years prior.

I took my muscle top off, revealing my hairy chest and then dropped the shorts, revealing my fitted swim trunks. The outline of my cock was evident through the fabric and my balls underneath created a sizeable bulge. I was the alpha male among a group of teenagers who would be ecstatic to even be called betas. I first headed toward the shower in the corner of the pool area to rinse off all the sweat from my workout. I swear the water was steaming off my body as soon as it touched my skin as my muscles were still boiling hot from my workout. I rubbed my hands in my hair, exposing my hairy armpits. The hair on my chest, my legs, and my forearms was even more noticeable once I was soaking wet. And my swim trunks were even more revealing, the shape of my cock clearly exposed, and my dickhead making an imprint in the fabric. I made my way to the hot tub and all eyes were on me. All these freshmen fully aware that their evolutionary stage was nowhere as advanced as mine, and most of them would never get there anyway. I entered the hot tub, but not before adjusting my package in my swim trunks for everybody to see.

‘Sorry guys. I just want to feel comfortable in the hot tub’ I told the group.

The looks on the faces of the young bucks in the tub were priceless. It went from ‘Wow, that’s a big dick!’ to ‘I can’t believe he just did that’ to ‘Good thing my trunks don’t show off my dick because I can’t rival with that’. But none of the looks were indifferent, I can tell you that!

I just sat in the empty spot in-between two twinks. My mystery neighbor was sitting two guys down from me. So, I wasn’t fully facing him, but I still had a decent view. He was fucking hot! He could have been a model. Not a badass model for a hip hop fashion brand, but more a dad-next-door model in a Walmart commercial, the type where a suburban family is happily passing a tube of ketchup at the dinner table, having the time of their life. I can tell a DILF when I see one and he was a dilfy DILF.

He didn’t have the body of an athlete or a gym rat, but certainly led a healthy lifestyle full of outdoor activities that kept him in shape. He was probably 6’0” from what I could tell when we rode in the elevator together earlier, and likely 175 lbs. Those were great proportions for a guy in his mid-30’s, an age when most guys have already given up on their body and picked the comfort of pizza and fries over the effort required to keep a flat stomach. But not this DILF!

He had a 3 or 4-day stubble that looked phenomenal on him. His hair was dark brown, but his stubble was turning salt and pepper on his chin and his temples. He wasn’t super hairy. His stubble was probably less dense than mine, with his skin apparent underneath. But, unlike any of the twinks in the hot tub, he could still grow a beard, even if the hair along his jaw line was thicker than the more sparce hair growing on the upper part of his cheeks. His pecs were not nearly as developed as mine, but he was not flat-chested like the twinks around us. He didn’t have a lot of chest hair, just a line of dark hair running at the very bottom of his chest, kind of nestled in the crevice below his pecs, starting from his nipples on each side, merging in the middle of his pecs, and growing upward towards his neck, where his hair would become more and more sparse, and eventually evaporate three or four inches below his Adam’s apple.

He had several tattoos on his arms, most of them written words that were most likely the names of his wife and kids. But he also had a firefighter helmet on his left chest, right over his heart. Was he a firefighter then? But if he was a firefighter, how was he related to the students competing in the golf tournament? Since he was too old to be a student, but too young to be a parent, and he didn’t have that coach look, I just assumed he was working for one of the universities’ athletic departments. Some unspecified position, pushing paperwork in a cubicle, and he was taking advantage of the golf tournament to get out of the office. Who the fuck was he?

He reached outside the hot tub to grab the backpack he had left along the wall and pulled out a couple of beer cans. That gave me a great view of his ass. Although he was wearing swim shorts, his wet shorts snuck up into his ass crack and accentuated his shapes. That was the firm ass of a man who plays sports, not the fat ass of a guy who watches sports on TV.

He looked at me and asked: ‘Can I entertain you with a beer?’

‘Of course’ I replied.

I’m not a big Budweiser fan. I’m too much of a snob to buy a working man’s brand. But who was I to turn down the offer from a guy with such a firm ass, an ass that would later get split in half by my big cock if I played my cards right? We had a connection now.

‘Thanks’ I said as I grabbed the can from him and opened it with a big ‘pshittt’.

‘I’d like a beer too, Mr. Simon’ one of the students said.

‘When you turn 21, Chris’ he replied.

‘Oh, come on, Mr. Simon!’ the kid argued.

‘Yeah! Come on, Dad!’ another kid said.

Wait?!?!? What?!?!? Dad?!?!? Did he just say Dad?!?!?

‘Don’t even start, Benny, I’m already in enough trouble with your mom’. Mr. Simon said.

‘Yeah! She’s got your balls locked in a jar!’ one of the other kids said, drawing laughter from the group.

‘Still better than having no balls at all, Timmy’ Mr. Simon replied, drawing more laughter from the group.

As the ball busting stopped, I regrouped a little. My mystery neighbor was Mr. Simon. And Mr. Simon, who looked like he was in his mid-30’s was the dad of little Benny here, who was a college freshman, even though he looked like he was 16. And all the other kids were Benny’s buddies, most likely freshmen as well. Either Mr. Simon was in his 40’s and looked a lot younger than his age, or he impregnated Benny’s mom when he was 15.

I started studying little Benny, who had called Mr. Simon ‘Dad’ earlier. Now that I knew the connection between the two, there was no question that Benny came out of Mr. Simon’s balls: same gorgeous face, same dark brown hair, same pointy nose, same light blue eyes. If I were into twinks, Benny would have won first prize. Tall and skinny, but with arms that were starting to bulk up. But he was way too twinky for me, just a little patch of hair in his underarms, to the point you could almost count them individually, not a hair on his face, and not even a treasure trail growing out of his swim shorts. I went right back to Mr. Simon who was giving me a nice view of his armpits while drinking his Budweiser.

At some point, Mr. Simon stood up to go to the bathroom. That gave me a nice peek at his treasure trail, which was just a thin line of hair growing from his swim shorts to his belly button. But because his hair was dark and wet, his treasure trail looked bushier than it really was. A few seconds after Mr. Simon had left, I told the group I had to go to the bathroom as well. As I stood up, my wet swim trunks were glued to my package, leaving nothing to the imagination, and my wet chest hair made me look even hairier than I already am. All the boys were staring at me, or at least at parts of me.

‘That’s why I’m allowed to drink beer and you’re not’ I told the group with a deviant smile, ‘And so that you know, I know exactly how much beer is left in my can. I expect to find it the way I left it when I come back’.

When I got to the bathroom, Mr. Simon was already at one of the urinals taking a leak. I went to the other urinal next to his and wiped my cock and balls out of my swim trunks. Similar to when I stood next to Tyler yesterday, the divider was low enough that both Mr. Simon and I could see each other’s dick over the divider.

I knew Mr. Simon wanted to see my cock just as much as I wanted to see his. But I wanted to let him be the one making the first move and getting caught. So, I just stared at the wall in front of me. I was standing in front of the urinal on the right. I held my dick with my right hand, so that Mr. Simon could have an unobstructed view of my dick. With my swim trunks lowered below my balls, my big cock sticking out, making a loud noise while letting out a big stream of piss, and my hairy pubes on full display, Mr. Simon wouldn’t have to turn his head very much to get a full view of my alpha package.

I sensed that he did.

‘Do you like what you see, Mr. Simon?’ I asked, while still staring at the wall in front of me.

‘Wh…  wha… what?’ Mr. Simon replied, not knowing what to say.

‘You don’t have to answer, Mr. Simon’ I double-downed. ‘That was a rhetorical question’.

As I said that, I turned my head to look at Mr. Simon. He had turned his head back and was now staring at the wall in front of him, pretending that’s what he had been doing all along. I took a quick glance at his dick, partially concealed by his fingers, but still visible. His dick was average in size, kind of what I would have expected given his frame. But it looked appetizing, nice dickhead, cut, a little more reddish than his shaft, but not quite purple either.

Since I didn’t really have to go to the bathroom, I just came here to stand next to him at the urinal, we both finished at the same time and shook our dicks, me shaking mine more than was necessary. And we both made our way to the sink to wash our hands.

‘You can call me Jeff’ he said.

‘No, I think I’ll call you Mr. Simon’ I replied, ‘but you can call me Brandon’.

As much as sex with Tyler had been amazing, from a hunter point of view, he had been an easy catch: A little virgin who couldn’t wait to be seeded by my big cock. The moment I pinned him against the wall, he gave himself to me with zero resistance. I now wanted a more challenging chase, going after a bigger prey, one that wouldn’t surrender without a fight, and Mr. Simon was a lot more interesting prize to go after. I was still trying to figure him out and develop my angle of attack.

We got back to the hot tub and started chatting a little. It turns out Mr. Simon was 38. He married his high school sweetheart right after graduation, became a fireman at 18 and his wife became pregnant with Benjamin within a few months. They also had a daughter two years later. Benny who was about to turn 19 had just started community college. Being soon-to-be empty nesters had put a strain on their relationship and Mr. Simon and his wife were not divorced yet but recently separated. He took an apartment a couple of months ago and was adjusting to his new single life, using every opportunity he had to spend time with his son.

Mr. Simon turned out to be an easy prey, even easier than Tyler. Guys who just went through a messy breakup see their certainties go up in flame and are often questioning a lot of things about who they are. And they’re sex deprived, big time! When I stood up to go back to my room, Mr. Simon decided to follow suit. While riding the elevator together, we smiled at each other. I don’t even remember who started it, but it was obvious he wanted my dick. Men with marital problems get horny really easily, not getting the frequency of release their dick craves for. And they also need to feel desired. Mr. Simon was like a ripe fruit at the grocery store, begging to be picked up.

‘You room or mine?’ I simply asked.

‘Yours’ he responded.

I like men in uniform: soldiers, firefighters, policemen. It’s not so much that I have a fetish. Don’t get me wrong, uniforms are sexy as fuck and the body underneath is usually top quartile. But more importantly, men in uniform can follow orders. Once you’ve established a hierarchy they can understand, little-by-little, you can make them do things you didn’t think they would, and they didn’t think they could. They know the meaning of physical effort. They can withstand pain. They are used to pushing themselves beyond their limits and not backing down when faced with a new challenge.

We got into my room, and I closed the door behind us.

‘Let’s get you more comfortable, Mr. Simon’ I said.

I grabbed his T-shirt, lifted it above his head, and tossed it on the desk.

‘Nice chest, Mr. Simon’ I said, while rubbing my fingers in the trail of hair underneath his pecs.

‘Thanks’ he said. ‘I try hard to stay fit’.

I bet his wife had not complemented him on his chest for quite some time. I then yanked his shorts down, revealing his Fruit-Of-The-Loom tidy whities.

‘Does your wife buy your underwear for you, Mr. Simon?’ I joked.

‘You should buy yourself something sexier.’ I added while grabbing the semi-hard member between his legs. ‘These don’t feature your goods in a very appealing way. Let’s just take them off’.

And I yanked his undies down, revealing his DILFy package.

His cock was neither big nor small. It was just normal. Perfectly adequate to impregnate his high school sweetheart right after graduation and make her moan a little while doing so. A dick size that was appropriate to make him a good husband, but without turning his wife into a begging whore. His balls were also adequate, certainly large enough to store the juice that produced Benny and his little sister. And I liked that they were hanging low. They were covered in a little bit of dark fuzz. His pubes were not trimmed, and he had just the right amount. Enough to surround the base of his shaft with masculinity, but not so much as to make it overwhelming. And the nice treasure trail I had noticed in the hot tub earlier spurted out of the top of his pubes, running all the way up to his belly button, only interrupted in the area around where the waistband of his briefs rubbed them out.

‘That’s a nice package you’ve got there, Mr. Simon’ I said, in a somewhat demeaning way. ‘Your wife must have been very happy with that’.

He didn’t have a comeback to my insult joke.

There’s a fine balance to strike when you go after straight guys. You have to complement them from time to time to boost their ego and help them cross the forbidden line. But you also have to humiliate them a little and keep reminding them that I might be gay, but I’m still the alpha. You have to tease them with your goods, but also make it clear they need to behave if they want their reward.

‘Do you want to see a real man’s cock, Mr. Simon?’ I added.

And without waiting for an answer, I unbuttoned my pants and let them drop to my ankles.

‘That’s the kind of underwear you should buy for yourself, Mr. Simon’ I said, pointing at my nice Calvin Klein boxer briefs that really cupped my dick and balls.

I grabbed his right wrist, and guided his hand toward my shaft, making his fingers trace it through the fabric. I wasn’t fully hard yet, but my cock had started to stiffen a bit.

‘You like that, Mr. Simon?’ I asked.

‘Yes’ he replied.

‘Good, because you’re going to feel much more of it down the road’ I said.

I grabbed the back of his neck and went on to kiss him. He kissed me back; his right fingers still playing with my shaft. I also grabbed his free willy, and it stiffened under the grip of my fingers.

I let go of his neck. He was now kissing me willingly and didn’t need any more guidance. I used my free hand to lower my boxer briefs and free up my cock, which was now getting to full mast. And I grabbed both of our shafts, rubbing them against one another, mine above his. My dickhead was pocking at his pubes, while his dickhead was trying to reach my balls underneath my shaft, unsuccessfully, since his dick was a solid inch shorter than mine.

‘You do it, Mr. Simon’ I said, as I grabbed his wrist and guided his hand toward our shafts.

Once he had both our cocks in his hand, he couldn’t help but realize how much bigger my cock was compared to his. Not that his was abnormally small. It’s just that mine was much bigger: longer, thicker, more veiny, just more masculine, period! While Mr. Simon was feeling my cock, his cock was throbbing on its own, desperately trying to grow as big as mine. But it just couldn’t.

After jerking our cocks that way for a minute or so, he made them both point skyward. Our two pairs of balls were now touching each other, the fuzz on his ball sack tickling mine. The base of our cocks was growing from the same spot, but my dickhead stood out a solid inch above his. But more so than the length, it was the girth of my cock that was staggeringly bigger than his. My arrowhead-shaped dickhead was a bit smaller than his mushroom head. But the lower down his fist travelled, the more my girth would diverge from his, to the point that the circumference of my shaft in the middle was probably twice his. I could tell he was excited by the thickness of my cock, but envious and intimidated at the same time.

I moved closer to him. My 6’3” towering over his 6’0”, and I looked down to him while he looked up at me.

‘Mr. Simon’ I said to him, ‘I’m taller than you. I’m bigger than you. I’m hairier than you. And I have a bigger dick than you. We can both agree it’s fair that I’m the one giving orders and you’re the one following them. Right?’

He didn’t say anything, just giving me a little nod that wasn’t even one.

‘I didn’t hear you, Mr. Simon’ I said.

‘Yes’, he mumbled.

‘Yes who?’ I asked.

‘Yes, Sir’ he replied.

‘That’s better’ I said. ‘Besides, it sounds like your wife has turned you into a submissive husband. So, it’ll be no different with me’.

‘Well, that’s not completely true’ he objected.

‘Shut up!’ I said. ‘Your wife has turned you into a pussy. She’s manipulated you over the years to chop your balls off. I’m going to awaken the man in you. Your cock is going to get the attention it deserves. And I’m going to drain out of your nuts more milk than the day Benny was conceived. I’m going to turn you back into the men you should never have stopped being’.

And I went back to kissing him forcefully, grabbing his hardon with my fist and squeezing it, making his dickhead turn purple with all the blood trapped in, and no longer flowing freely. And then I released my grip.

‘It’s not your first time with a guy, is it? Mr. Simon’ I asked.

‘No, it’s not’ he replied.

‘The tone in your voice is telling me your first time was not enjoyable’ I said.

‘No, it wasn’t’ he admitted.

‘What happened?’ I asked.

‘When I first became a firefighter, I went through a hazing ritual that got a little bit out of hand’ he said.

I didn’t think it was appropriate to ask him to expand. The tone in his voice and his demeanor was saying it all.

‘And it sounds like it left a sour taste in his mouth’ I said. No punt intended.

He nodded.

‘That’s OK. This time is going to be different. You’ll never forget your second time, Mr. Simon’ I added ‘I’m gonna make you cum more juice than you thought your balls could hold. It’s gonna blow your mind’.

Now that we were both naked in my bedroom and the future chain of events was becoming real to him, Mr. Simon started to look very nervous.

‘You look tense, Mr. Simon’ I said. ‘I want you to relax. I’m gonna give you a massage’.

I made him lay on his stomach on the bed, his hole exposed to the elements. I made sure his cock was pointing forward, so that it was already in position for when he would get rock-hard under the sensuality of my massage.

‘I think I have some massage oil in my toiletry bag’ I said.

I quickly went to the bathroom and came back with a bottle of scented oil, which I poured on his shoulders. I also brought a towel that I laid on his mid-section, covering his ass, the way real masseuses do. I wanted him to relax and not worry about me making a pass at his ass unexpectedly. Not just yet. And since I was straddling him with my rock-hard cock out upfront, I didn’t want my cock pocking at his lower back and distracting him from the massage.

‘Close your eyes and relax, Mr. Simon’ I whispered in his ear.

I started with his neck and shoulder area. He had nice shoulders, not hyper-muscular like a body builder, but firm under the touch, the shoulders of a working man. Mr. Simon was enjoying my hands rubbing his body and was moaning a little every time I found a knot. Although he had been trying to play it cool in front of Benny and his buddies, Mr. Simon was under a lot of pressure, having just split with his wife, been forced to get his own place, and not spending as much time with his kids. And certainly, the lack of sex was a big source of tension build-up.

I eventually moved down to his back. The towel was covering his ass, just letting the very top of his ass crack stick out. I rubbed my strong hands up and down his lower back, all the way down to the top of his ass crack, teasing him, going down a little further with each movement, but never crossing the line, keeping the massage professional, if it wasn’t for my rock-hard cock waving above his lower back. I was leaking precum like crazy and had to wipe my dickhead from time to time, bringing my translucent juice to my own mouth, as I didn’t want my juice leaking on Mr. Simon, and making him feel uncomfortable.

I then turned around, facing his feet, my ass sitting on his, and I started massaging his thighs. They were firm and muscular, not a lot of body fat. The scented oil accentuated his dark hair, making it stick and forming dark patches that screamed masculinity.

I got up and stood by the end of the bed to massage his calves and feet. His calves also had a fair amount of dark hair. They were not overly developed, but I could clearly feel the two main muscles under my fingers, they were hard to the touch, and you could tell Mr. Simon was a runner. I then massaged his feet, handling them firmly to make sure I wasn’t tickling him. They had a little bit of hair on the upper part. And I was playing with his toes. I bent his knees to lift his feet up and started licking his big toe. It kind of surprised Mr. Simon, but he enjoyed my tongue swirling around his big toe while my fingers were playing with his smaller toes. He was moaning a little from this more sensual touch.

I then asked Mr. Simon to turn around and lie on his back, holding the towel to give him privacy, and looking away as he was positioning himself. It was kind of pointless since I had already held his hard dick in my fist earlier. But I wanted the massage to be sensual, not sexual, making him relax to make him more pliable down the road. Once he was lying on his back, I repositioned the towel to cover his mid-section. His dick was harder than steel and formed a visible mound in the middle of the towel, which was jumping up and down as his dick was throbbing underneath. Mr. Simon looked at me kind of embarrassed by his uncontrollable member.

‘Don’t worry about it, Mr. Simon. I want you to relax’ I said ‘Close your eyes’.

I straddled him again, my hard cock laying on top of his hard cock, with just the towel in-between. I could feel his cock throbbing underneath mine, lifting my meat with every pulse, making it look like my cock was throbbing on its own. His cock was clearly hungry, having no problem lifting the weight of my big schlong.

I started massaging his pecs. They were also firm, not overly developed, but just zero body fat. I loved the feel of his firm muscles under my touch. I also loved the feel of his chest hair, mostly under my thumbs, since his hair was concentrated on the lower part of his chest, right at the crack between his pecs and his abs. I was playing with his pecs the same way a straight guy would be playing with boobs, enjoying every second of it. Mr. Simon was also savoring my firm rubbing. Both our cocks were now throbbing, mine beating up his on the way down. My flow of precum had doubled in volume and I had to collect the droplets at my piss slit at frequent intervals, before they would start dripping in his belly button, above the edge of the towel.

I eventually removed the towel, and our dicks were now touching each other, each throbbing on its own. I grabbed both our shafts and started rubbing them against each other. Mr. Simon brought his right hand to our dicks and pushed my hand away. And he started rubbing our dicks, in a much more vigorous way than I had been. We were both turned on by the sensation, me fueled by the power trip of my dick being so much bigger than his, and the feeling of superiority alphas get over average-sized men; him turned on by the feeling of my big fat cock between his fingers, playing with a much bigger toy than the one he’s used to playing with. His cock was also leaking precum, our two fluids joining forces to soak his pubes and treasure trail.

‘Turn around and get back on your stomach, Mr. Simon’ I ordered.

He obliged and I now had a full view of his muscular ass. I moved back a little, my ass now sitting on his calves, giving me the chance to massage his thighs and his ass. His ass was not as hairy as mine, but it was sprinkled with hairs all over, kind of a low-density meadow, each individual hair having found its own spot on his ass, away from its neighbors. But his dark hair turned denser inside his crack and even more so lower down, closer to his hole, which was almost invisible, protected by a dense forest. What a gorgeous ass that was, I couldn’t wait to rub it, open it up for my weapon, and eventually split it in half.

His butt cheeks were firm and muscular. They felt amazing under my touch, fighting back any attempt by my fingers to spread them apart. I loved sliding my fingers up and down his hairy crack, and I could feel the electricity radiating through his entire body as I travelled ever closer to his forbidden spot, teasing it but never touching it yet. I could feel his whole body tense up, the closer I got to the spot, and relaxing as my fingers moved back up his crevice.

I moved back along his legs, my ass now sitting on his ankles. I lowered my head, spread his butt cheeks apart with my hands, and the first part of my body to ever touch his hole was the tip of my tongue. Mr. Simon jumped at the sensation of my pointy tongue lightly brushing the most private part of his body.

‘Oh, my God!’ he cried.

‘You like that, Mr. Simon?’ I asked.

‘Fuck yeah!’ he replied.

And my tongue went back to teasing his opening, fighting its way through the dense hair, which got darker the wetter my spit made it. Mr. Simon was shivering. At 38 years of age, it was the first time someone had been feasting on his back entrance, and he couldn’t believe how amazing this forbidden sensation felt. I ate his ass alive, burying my nose in his hairy crack, sniffing the mix of sweat and manliness, and drilling my tongue as deep as I could. Each drilling was followed by a retreat, letting his hole close up again, my tongue circling around his rosebud before the next wave of attack.

His balls were laying on the bed cover, in-between his legs, and the stubble on my chin was grinding against his silky balls like sandpaper, setting them on fire. To soothe them, I would forget his hole for a minute and lick his fuzzy balls.

‘Oh yeah!’ Mr. Simon kept yelling, in between other sounds that alternated between grunting, moaning, and plain whimpering.

And I would go back at attacking his hole.

‘Oh yeah, go deeper’ he pleaded. ‘Go deeper in my hole’.

‘There’s only so far my tongue can reach Mr. Simon’ I said.

‘Then stick it in’ he ordered.

‘Stick what? Mr. Simon’ I asked.

‘Your cock’ he answered. ‘Stick your big cock in my hole. I want to feel your cock inside me’ he pleaded.

‘Is that what you really want, Mr. Simon?’ I asked. ‘You know I’m thick!’

‘Yeah. Fuck me! Fuck me!’ he yelled. ‘I don’t care how big you are’.

I brought my cock closer to his entrance, first rubbing my pointy dickhead up and down his hairy crack, teasing him a bit longer.

‘I have a condom in the left pocket of my shorts’ he said, regaining his senses in-between his lustful absences.

I stood up and grabbed the condom in his pants.

‘That’s not going to work, Mr. Simon. Too small for me’ I said. ‘But I have a box of Magnums in the bathroom’ I added.

His condom would have been perfectly fine on my cock, maybe a little bit tight on the girthiest part in the middle of my shaft. But I wanted to maintain my dominance over him, reminding him he had turned into a begging whore, willing to be fucked with a baseball bat if that were the only thing available to satisfy the carnal urges of his hungry hole.

I quickly went to the bathroom and came back with the shiny golden pouch in my hand, a deviant smile on my face, and my big fat cock flapping between my thighs, ready to be imprisoned. I tore the pouch apart with my teeth and meticulously rolled the rubber down my enlarged shaft.

‘That’s a nice fit!’ I declared, while admiring my crowbar, about to force open Mr. Simon’s safe.

‘You may want something to bite on, Mr. Simon’ I said, as I brought a pillow to his mouth.

Mr. Simon was still lying on his stomach, his legs slightly spread, exposing his tender rosebud about to be destroyed. I placed my hands in the crack of his ass, spreading his butt cheeks apart, revealing his hairy hole. His hole was still gasping from my tongue having opened it up. From time to time, you could see the red lips, just beyond his ring, begging to be stretched even further. I placed my two index fingers at his entrance, spreading his hole like a rubber band, and I placed the tip of my dick. I pushed in. And my dickhead disappeared in his tunnel, like a scout exploring a cave with a headlight on his helmet, paving the way for the rest of the speleologists to enter the cave.

My meat slowly pushed its way inside his bowels, slowly disappearing in his depths, inch after inch, dilating his ring like a woman giving birth. The condom was being stretched on my rod, not able to progress inside his hole at the same pace as my meat. I could sense the top of the condom stretching on my dickhead, the little cum pouch on top of my piss slit being the only part of the condom not being stretched to its maximum.

‘I just past the halfway point, Mr. Simon’ I whispered in his ear, as the girthiest part of my cock was tearing his hole apart ‘three more inches to go’.

Mr.Simon was biting the pillow, his screams muffled by the feathers. Long ‘hhhuuummmfff-aaarrrggghhh-hhhuuunnnhhh’ as my hips shoved my meat inside him, forcing his mancunt to accept my girth.

When I fuck a guy who’s not used to bottoming, it always reminds me of these YouTube videos when a truck driver is trying to make his way under a low overpass that has a sign that clearly says ‘13’5” maximum’ but takes his chances anyway, only to see the trailer of his truck getting stuck under the overpass. But anatomy is different from engineering and doesn’t abide by the same constraints. Even though Mr. Simon’s sign would probably have said ‘6 inches max’, if he had one tattooed next to the entrance of his tunnel, there is no mancunt that a little bit of goodwill and the right amount of lubrication can’t make penetrable. And even lack of goodwill can always be overcome with a little bit more force. So, I just pushed through, and Mr. Simon just took it.

Mr. Simon knew there was still a lot more of me to be stuffed inside his hole. But after several minutes of a methodical intrusion on my side, and agonizing stretching on his side, my pubes were pressing against his butt cheeks. I had given Mr. Simon every inch I had.

‘You took it all, Mr. Simon’ I whispered in his ear. ‘All seven of my inches’.

I just stayed there for a minute. Giving his aching cunt the opportunity to adjust to its new dimensions. Mr. Simon still grunting in the pillow, while my tongue was licking the side of his neck, right below his ear, and my fingers were fondling his nipples underneath his chest.

‘I’m gonna start fucking you, Mr. Simon’ I whispered, drawing a sense of panic from him, as his hole was already burning from the overstretching, and not yet ready to endure any more battering.

‘I know I’m thick, Mr. Simon, and it’s all you can think of, right now’ I said, ‘But that’s what you asked for. And in the end, it’s gonna feel much better than your first time. I promise’.

And I started pulling my meat out, pulling out the inner skin of his cunt at the same time. And I pushed back in, reopening his ring, and exploring the depths of his colon. Mr. Simon was still making noises, his screams muffled by the pillow, but the pitch of his voice had gone up a notch, now sounding more like whimpering. His whimpering conveyed a mix of pain, fear, and hopelessness, at what his tight hole had already endured, and at how much more was to come.

But as I started expanding the range of my cunting, his ring continued to dilate, to the point it was holding on better, if that’s the right word, and was no longer drifting in and out as much, under the attacks of my thick cock in and out of his hole. Mr. Simon was no longer biting the pillow underneath him, although he was still panting heavily, his skin shining with thousands of microdroplets of sweat.

‘Let’s switch position, Mr Simon’ I said. ‘You’re gonna love what I have in store for you’.

I pulled my cock out, allowing his battered hole to retract to its normal position, which caused him to gasp. I laid on my back, my big cock pointing upward like a column in the middle of a city square. And I made Mr. Simon face my feet, my hand holding his waist and guiding his lower back above my pole. And Mr. Simon lowered his body, impaling himself back on my rod. The second entry felt a lot easier than the initial one, but his ring was still tight and my girthy cock rubbed against the walls of his chute until his butt cheeks were laying on my pubes.

‘Lay over me, Mr. Simon’ I ordered ‘Don’t be afraid to put all your weight on me. I can handle it’.

He titled his upper body backward, his smooth back now resting on my hairy chest. His left ear now at mouth level, allowing me to gently bite his earlobe. And he extended his legs on each side of mine. He was now laying on top of me, his legs and arms falling on each side of my body, like a starfish, his hard dick proudly pointing up and throbbing above his pubes. I felt his body fully relaxed, laying inert above me, ready to endure the pounding it knew was coming. Meanwhile, I loved the pressure of his 175 lbs on my torso. Mr. Simon wasn’t so heavy as to make it uncomfortable.

I started sliding my hard cock up and down his stretched hole and started fucking him again. Since my legs were extended in front of me, almost touching each other, my balls didn’t have much room to hang low and were kind of resting on my inner thighs, close to the base of my cock. Meanwhile, Mr. Simon had his legs spread eagle and his low hanging balls were swinging like mariachis in rhythm with my thick cock pounding his hole. His balls were slapping against mine, which was both hot as fuck to watch and listen to, but also provided a nice sensation, just a gentle tap to remind me my balls were still there and progressively heating up toward their boiling point.

‘You like that, Mr. Simon?’ I asked, ‘you like my cock up your ass?’

‘Yeah’ he responded, ‘Fuck me!’

And I started fucking him harder, never fully exiting his hole, but instead pulling back to just below my dickhead, and pushing back in, as deep as I could reach. His ring was no longer providing any resistance and was enduring the pounding completely defenseless. As I accelerated the pounding, Mr. Simon became more vocal, sometimes yelling intelligible words, like ‘Yeah! Fuck me!’, other times just making sounds like ‘Ah’, ‘Oh’, ‘Huh’, conveying his defenselessness, but his pleasure at the same time. His cock was rock-hard, waving from left to right under the hammering, but only a small range, given how rigid it was. It was now leaking a continuous flow of precum on his treasure trail, which dripped on the side of his stomach and onto my hips.

I knew Mr. Simon’s balls were getting close to their boiling point and his geyser was about to erupt. I grabbed his hardon with my right hand, while my left hand started fondling his left nipple. And I started sucking on his earlobe with my lips. His legs, which had been hanging on the side of mine, tensed up and started floating in front of us. I felt his dick swell in my fist, and Mr. Simon yelled a loud ‘Aaarrrggghhh!’ as he reached the point of orgasmic ecstasy. And thick white cream started gushing out of his piss slit.

Mr. Simon wasn’t a shooter and his manjuice never made it past his belly button. But he made up for the short distance of his release with ample volume. His balls sure could produce juice and his dick spurted out ropes and ropes of man milk which were covering his pubes and his lower stomach. He produced enough juice to impregnate his wife with quadruplets.

Fuck! The scene was hot and almost brought me to the edge. But I didn’t want to cum in the condom. The condom had been stretched so tight that only the little cum pouch stood in front of my dickhead, and there was no way that little pouch could accommodate the flooding my balls were about to release. I stopped moving, to allow my cock to cool down, and I started kissing Mr. Simon’s neck, making him moan with pleasure, while he was recovering from his climax. His members were relaxed again, and his arms and legs were hanging on the side of my body. I don’t think I could even feel his hole around my hard cock anymore, as his ring muscle had been distended so much.

I eventually pulled out of his hole and removed the condom from my still hard cock.

‘Get down on your knees, Mr. Simon’ I ordered. ‘You might be done, but I’m not’.

He obliged and kneeled on the bed. His DILFy juice was so thick and creamy that it barely dripped and just stayed trapped in his pubes and treasure trail. It was incredibly white, especially in contrast to his dark pubes. He must have been sniffing titanium dioxide to produce such pure white manjuice.

I stood up on the bed, my left hand flat on the popcorn ceiling above the bed while my right hand started jerking off my overexcited cock, which had not yet been allowed its release.

‘You’re already covered in cum, Mr. Simon’ I pointed out. ‘We might as well fill in the empty spots before you shower’.

Seeing Mr. Simon on his knees in front of me, waiting for his facial was somewhat of a power trip, which got me really turned on. I knew his soiling would be coming soon. I felt shivers all over my body as my alpha juice was reaching its boiling point inside my swollen balls. And then I felt this incredible sensation of my juice travelling through my piping at the speed of light, building pressure before its well-deserved escape. I yelled a loud: ‘Fuck! I’m gonna blow!’ And a huge glob of my alpha juice crashed in Mr. Simon’s stubble, right below his chin. I angled my cock differently in-between each volley to baptize Mr. Simon in all the right places. My second rope landed right at his hairline and started dripping down his forehead. The third one landed between his left eye and his left ear, dripping along his temples. And more ropes landed all over his face, on his lower lip, and on his mustache right under his nose. The last few ones landing on his chest.

Mr. Simon was covered in white jizz from his hair down to his pubes. That was a scene out of a porn film. One might have thought that ten different guys had relieved themselves on Mr. Simon to cover his face and body with so much spunk. I grabbed him by the armpits, made him stand up and gave him a long passionate kiss, feeding him the jizz that was dripping out of his mustache, keeping a little bit for myself. And I gave him a big hug, so that some of the spunk transferred to my hairy chest and pubes as well. We were both hot messes, like a canvas where Jackson Pollock went crazy with his paint dripping technique.

‘So, Jeff, did you enjoy your second time? I asked, calling him ‘Jeff’ rather than ‘Mr. Simon’ for the very first time. Now that we were done with the performance, and we were recovering from the intensity of the fucking.

‘I did’ he replied. ‘It was intense’.

I brought a couple of fingers to his battered hole, entering with no resistance, barely feeling the walls.

‘It will eventually tighten back up. You’ll be back to normal in no time’ I joked.

I hope I was right, and his ring hadn’t been permanently enlarged. And I assaulted his mouth with my tongue while grabbing the sides of his head.

We showered together, using probably half of the bodywash bottle to wash away all the jizz entangled in our hairy pubes, chest hair, and beards. I rubbed soap on his chest while he rubbed some on mine. And I rubbed soap on his pubes, while holding his cock with my other hand, bringing him back to a full hardon while doing so. I grabbed a towel and sponged him out, admiring his DILFy body at the same time. And we both got dressed.

‘You should get back to your team before people start wondering where you were, Mr. Simon’ I said.

He smiled and left the room.

It was 9pm. I hadn’t had dinner yet and I was fucking starving. It was too late to go to Applebee’s or Cracker Barrel. I ended up picking up a meal at McDonald’s. I had burnt enough calories to earn it.

I was still horny as fuck, despite having fucked both Tyler and Jeff in the span of three hours. I ended up rubbing one off before going to bed, not quite sure if I should be thinking about Tyler or Jeff while stroking my meat. I closed my eyes and ended up thinking about Tyler more so than Jeff. And my last little soldiers made their final exit down the drain of the bathroom sink.

I will be sleeping well tonight!