Anonymous encounter: He made me cum hands free

by Jeremy Miller

21 May 2022 11510 readers Score 9.3 (152 votes) PDF Mobi ePub Txt


He made me cum hands free

This week, my business travels took me to Minneapolis. My company has a couple of big clients there and I had a set of meetings I needed to attend. I’ve been to Minneapolis several times in the past and I’ve always had good luck hooking up over there. I don’t know why, but there seems to be lots of guys with big dicks in Minneapolis. I’m not sure if there’s something in the water, or if it’s the Scandinavian genes, or if it’s all these corn-fed Minnesota farm boys that made their way to the big city, but my average sized dick always seemed to be humbled when I compared it to the big fat cocks of the guys I’ve hooked up with in the Twin Cities. I was certainly looking forward to this trip, hoping my lucky streak up north would continue.

Sometimes, I’m still craving for dicks, but I don’t really have the sexual energy for anonymous anal sex or even for blow jobs for that matter. This week was one of those weeks. I was perfectly content with just meeting some guys and jack off together in my hotel room. I wasn’t interested in anything hard core. I had started to message several guys before flying to Minneapolis. People are so flaky nowadays that anonymous hook-ups require a lot of planning. Between the guys who cancel at the last minute, claiming that something came up, and the ones who plain ghost you, I always try to have several irons in the fire, banking on the odds that at least one of them is going to convert. And if all of them convert, I just deal with the sexual abundance. This week the hunt had been fruitful, and I had a different guy lined up every day of the week. While messaging them, I made it clear that I was only looking for a beat-up buddy and that jerking each other off was as far as I wanted to go.

On Monday evening, I hooked up with a blond guy who looked like he was in his late 20’s. The exact Scandinavian-type looks I expected to find in Minneapolis. The guy was a little bit shorter than me, 6’0” or 6’1”. But he had an incredible body, not beefy, but tight lean muscles, the exact swimmer body I so look forward to. He was into yoga, and it showed. He had rock hard abs. I knocked on them, like if I was knocking on a door, and they felt like solid wood. Fuck!

Both sides of his head were shaved, military style. But he had long hair in the middle, tied up in a bun on top of his head. He had a short blond beard. He was yummy! I never asked for his name. He never asked for mine. His torso was completely smooth, with just a light dusting of chest hair in-between his pecs. I couldn’t tell if he was gay, bi, or straight. But it didn’t really matter since we were just going to jack off together. We both got undressed and compared our respective packages. He had nice blond pubes, not quite as blond as the hair on his head or his beard, but still fairly light, kind of dirty blond. He was manscaped somewhat, but he still had abundant hair down there.

His cock was nice. It looked exactly like mine, but an inch longer, 6 ½ to 7 inches vs. 5 ½ to 6 inches for mine. We brought our cocks side by side. I grabbed both of them with my hand and started rubbing them against one another. His dick was clearly sticking an inch longer than mine, with his dickhead pressing against my pubes while my dickhead fell short of reaching his pubes. But aside from the length, our cocks were almost identical: same thickness, same mushroom head, both cut.

We started jacking off, both laying on our back, side-by-side on the bed cover. At times, we grabbed each other’s cock, but for the most part, we were each jacking our own cock. I was really turned on by his toned body. I came first and splashed all over my chest and my stomach. Since I was already covered in my own spunk, I asked him if he wanted to cum on my stomach too. He got up, straddled my thighs, with his cock facing me, and he shot his load. He didn’t shoot very far. His cum just dripped on my belly button, more than anything else. But I enjoyed watching the spasms of his body and his facial expression as he climaxed in front of me. It was hot!

He got up, put his clothes back on, and left. And that was the end of it. Nice experience though!

I had a second guy lined up for Tuesday evening. He was in his late 20’s or early 30’s. His body type was very similar to the blond guy from the day before. He was a bit shorter, maybe 5’10” or 5’11”, but equally toned. Same lean muscles, same rock-hard six-pack. But there was one big difference. The Tuesday guy was hairy. I mean really hairy.

He told me he was Italian American. His grandparents immigrated from Puglia in Southern Italy on his dad’s side and from Sicily on his mom’s side. I didn’t know there was a big Italian community in Minnesota, but that explained his dark complexion. He had what I would call a Mediterranean skin. He was one of those guys who had a tan year-round, even during the snowy Minnesota winters. He had dark hair and a similarly dark one-inch-long beard.

Before taking his shirt off, he told me: ‘So that you know, I’m hairy’.

I kind of suspected that based on his profile, but he must have dealt with shocked reactions in the past and was paving the way for what I was about to see. He removed his shirt, and no kidding, the guy was indeed crazy hairy. He had to be the hairiest guy I’ve ever been with. His chest and stomach were covered in thick dark hair, to the point that you could barely see the skin underneath. And he was probably doing a lot of grooming too, to keep things under control. His chest hair was an inch long or so, same length as his beard. So, he looked very well-kept and not unruly the way some hairy guys are. He also had hairs on his shoulders and his upper back, as well as a thick dark patch on his lower spine, just over the top of his ass crack. His six-pack was so defined that you could still outline it under his thick hair, with lines of dark hair even more pronounced in the crevasses between his abs.

I’ve traditionally not really been attracted by hairy guys. I’m not into bears, and especially not older bears who are in bad shape. But he was more of an otter, and I found the hair on his lean toned body surprisingly attractive. I rubbed my hands into his chest hair, kind like if I was giving a belly rub to a puppy. It was hot! The contrast between his dark-skinned hair-covered chest and my pale completely hairless one was quite striking. Since he seemed very self-conscious about his overabundant fur, I wanted to make sure he felt at ease. So, I told him I was digging the hair. And I actually was!

We started making out. I enjoyed the tickling of his mustache and beard on my lips. While we were kissing, I unbuckled his pants and they dropped to his ankles. He was wearing tight black briefs, which accentuated his slim waistline. The hair on his lower stomach was plunging all the way into his briefs, and it continued onto his equally hairy thighs. These tight briefs looked great on his tight hairy body.

Given how hairy he was, I expected him to be packing a huge schlong. And Italians have that reputation anyway. It turned out it wasn’t the case. I lowered his briefs, and they revealed a dick that was average size at best. Once he got hard, his dick was just like mine, if you made abstraction of the bushy hair all-around of course. His dick was neither long nor girthy. And his ball sack was equally average.

There is this belief out there that hairy guys are manlier and therefore have bigger dicks. I haven’t found that to necessarily be the case. The guy with the biggest cock I’ve ever seen was completely smooth, while this hairy beast in front of me had an average sized dick. To be perfectly honest, I have found zero correlation between body hair and dick size. I know I shouldn’t be bringing the word ‘correlation’ into a sex story, but I’m in data analytics. That’s just the way my brain functions, even during sex.

He got on the bed, standing up, raising his arms all the way up, with the palm of his hands flat against the popcorn ceiling. I got on my knees on the bed and started sucking his hairy cock. It tasted musky and the hair didn’t really bother me. His bush was nicely groomed. But despite all the trimming, it was still dark and thick, and I couldn’t see his skin underneath. I could only imagine what a tropical jungle his pubes would look like au natural. He must own some professional grade equipment to deforest this thing.

Sucking dick was already more than I thought I’d be doing with this guy, but the chemistry was good between us, even though we couldn’t have looked more different. I played with his balls. Curiously, his ball sack was probably the least hairy part of his body. His balls were not completely smooth, but they were only covered by a light dusting of fur. And ironically, I was the exact opposite. I am completely hairless on most of my body, but I have the hairiest pair of balls you’ve ever seen. My balls were way hairier than the balls of this Italian otter. How weird was that?

I eventually got up and we started jerking each other’s dick while kissing, both of us still standing on the bed. After a few minutes, he started moaning and I knew he was getting close. I was getting close as well. We ended up cumming at the exact same time, still standing up on the bed and facing each other. I shot several loads of white jizz all over his dark hairy six pack. His cum landed on my thighs, since I was taller than him, with his last few drops dripping on the bed cover. Trapped in his black hair, my jizz had never looked so white.

We made our way to the bathroom. It had a nice steam shower that was large enough to easily accommodate both of us. We made out while rinsing our cum away. My jizz caught in his stomach’s thick hair was a little bit harder to wash away than his jizz on my mostly hairless thighs.

He got dressed and left. ‘Well, that was something different!’ I thought to myself.

But the guy I was really excited about was the guy I had lined up for Wednesday evening. I was thrilled when I heard the knock on the door of my hotel room.

‘Hi, I’m Justin’ he said.

‘I’m Jeremy’ I replied.

The second Justin walked in; the room radiated with sexual energy. This was going to be good! He must have been 6’4” or 6’5”. I’m 6’2” and he was towering over me. I had to look up to him, which I rarely have to do. And he was built too. Exactly what you would expect from a Minnesota farm boy. Not that he had the bulging defined muscles that gym rats develop. He was just a naturally solid guy. He must have been on the football team of his high school. How could any football coach pass on a guy like that?

Justin was in his mid-30’s. He had a goatee, but it wasn’t thick. He didn’t look like a particularly hairy guy and could barely pull it off. I don’t think he could have grown a full beard. What a contrast with the Italian otter from the day before! But because his hair was dark as well, whatever little hair he had made his goatee look somewhat credible.

‘I came directly from work. Do you mind if I use your shower first?’ he asked. ‘I’m a cook. I just finished my shift.’

I could have figured that out myself as he was still wearing his cook uniform or whatever these things are called. He was wearing grey and black checkered pants and a white bib apron, not the kind of apron tied in the back that Julia Child put over her street clothing, but the white shirt made of thick fabric that looks like a built-in apron. Normally, I’m all for sucking a working man’s sweaty cock, but Justin smelt like grits more so than sweat. Yes, please, take a shower!

‘Of course. Go ahead!’ I replied, ‘Feel free to use one of the towels on the rack behind the door’.

I sat on the bed waiting for him to be done showering. After a couple of minutes, he came out of the bathroom. He was completely naked. He didn’t bother putting his clothes back on, just to take them off right away. His torso was smooth, and his pubes were completely shaved. Usually, I’m not a big fan of shaved pubes, but Justin had such a big built that he still looked manly, even with his shaved pubes. His forearms and thighs had some hair but not a lot. His armpits were the only part of his body that was meaningfully hairy. But of course, my eyes went straight to his dick. His dick was soft, and it was noticeably short. It couldn’t have been longer than 1 ½ inches, 2 max. But it was really thick. His girth fully flaccid was already bigger than mine when I’m rock hard. I got off the bed and walked toward him, him fully naked and me fully dressed. But he didn’t seem to mind.

‘So, what do you wanna do? He asked

‘Just like I said when we were messaging’ I replied ‘I’m happy with just jacking each other off. But I’m open to go further if you ask nicely’.

I was lying. Just seeing this hunky guy, naked in front of me, had caused my sexual hunger to go up 1,000%, and there was no way a mere hand job would suffice to satisfy my hunger. My dick was already hardening in my pants.

‘Is it OK if we kiss?’ I asked.

‘Sure’ he replied.

We got closer to each other and started kissing. And Boy, the guy could kiss! He was a naturally sexual guy, and I could tell just from his kissing and his embrace that he knew what he was doing. He smelt very citrussy, having just showered with the Crabtree & Evelyn body wash the hotel provided. As we were kissing, I started feeling his manhood growing and pressing against my leg.

I was still fully clothed. So, I removed my shirt, and our smooth naked torsos were now pressing against each other. I could feel the warmth of his body while the temperature in mine was quickly rising. He reached down to unbuckle my pants and lowered my zipper. Since he had been naked all along, I decided to drop my underwear right away. ‘So much for my sexy briefs!’ I thought to myself. But we were already way passed that point. While we were still kissing, I brought my right hand to his cock, which was now fully hard. Holly fuck! It was thick. But bizarrely, not particularly long. It was still longer than mine, probably 6 or 6 ½ inches vs. my own 5 ½ or 6 inches. But it’s the difference in girth between his dick and mine that was mind-blowing. In a dick-tionary, the picture of his dick could have been used to illustrate the definition of ‘short and fat’. It’s not that he was particularly short. 6 ½ inches is nothing to be ashamed of. But it was so thick in comparison that the proportions were off.

Justin went down on his knees and started sucking my 5 ½-incher. I felt bad that I would soon have the privilege of enjoying his amazing piece of meat while I had very little to offer in return. But Justin didn’t seem to mind. He was sucking my dick hungrily. He was just as good at sucking dick as he was at kissing. I put both my hands behind his head and pressed his nose against my pubes.

‘Come on, swallow it all the way’ I ordered ‘It’s not that big. You can do it!’

That would be pretty much the only ounce of dominance I would exert all night. The rest of the evening would turn into a progressive surrendering on my part, until I relinquished any control of the situation and allowed him to make me his bitch. Although he probably didn’t have much experience deep throating Justin took all my manhood in his mouth, with no pushback and no apparent struggle. Not that it was much of an accomplishment given what he was dealing with. He did it in a ‘Sure, whatever!’ kind of way.

It was then my turn to get down on my knees and take care of his cock. His cock had a lot of similarities with mine: big mushroom head, constant girth throughout. But it was so much thicker. It was like if someone had taken my dick and pumped some helium into it to make it double in size. I’m not sure if his cock was the thickest I’ve ever seen, but it was clearly up there. I couldn’t help but study the strange proportions of his tool. If his cock had been 8 or 9 inches long, it would have been the most beautiful cock I’ve ever seen, either in person or in porn. He also had a nice pair of balls. The size of his balls being proportional to his girth, not to his length. I took his thick cock in my mouth and started sucking it. I had to stretch my lips just to allow his mushroom head in.

‘If we’re both gonna suck each other, do you just want to 69?’ he asked.

‘Sure’ I said.

We jumped on the bed, laid on our side, and I shoved his big fat cock back into my mouth, while he started sucking my cock that was half the girth of his. Justin was an incredible lover, and he knew what he was doing. It’s not just that he was good at sucking my dick. He was good at playing with my balls. He was good at changing the rhythm, alternating from rough, dominant moves to soft, sensual moves. I couldn’t tell if it was pure instinct or experience; probably a mix of both. It didn’t look like he was very experienced with guys though. But whatever he had learned with girls, he had no problem applying it to man-on-man action.

I normally cherish the rivalry between me and another guy. I’m competitive in nature and competition is part of what fuels me, in sex and in real life. But there was no competing with Justin. I felt like he was in a completely different league. And it’s not just because my dick looked like a garden snake in comparison to his python. I’ve been with guys with big dicks before, longer than Justin. It wasn’t just that. Justin didn’t even have to try to be dominant. He just was. His size, his demeanor, his sexual energy, his experience. Everything about him radiated power. He just took away my will to fight. He had me bested in every possible way and surrendering to him felt like the only possible outcome. I could feel myself drifting into submission, something I had never experienced before. But at the same time, he was putting me at ease, and I wasn’t scared of submitting to this stud of a man. I was like a sailor being lured by the enchanting singing of the sirens, slowly gliding to my demise, but doing so in a carefree way. In the span of 30 minutes, the hunter had become the prey. A prey that was about to get devoured by his master.

If I was going to be dominated by this stud, it had to be all the way. I had to let his big fat cock invade the most intimate part of my body and experience the feeling of powerlessness he projected.

‘Have you ever fucked a dude before?’ I asked.

‘Never’ he replied.

‘Do you want to fuck me?’ I asked.

‘Why? Do you want me to?’ He responded.

‘Actually, I think I do’. I replied.

‘What about a girl? Have you ever done anal with a girl?’ I continued.

‘Nope’ he said, ‘It’s not for lack of wanting. But I’ve never found one who would let me’.

‘I don’t blame them’ I joked ‘With how much you’re packing, that’s not surprising’.

‘What about you? Have you ever been fucked before?’ he asked.

‘A couple of times’ I replied ‘But never by a monster like yours. That would be a first’.

‘So why do you want to try?’ he continued.

‘I don’t know’ I responded, ‘I’m always up for a challenge, I guess. But only if I feel comfortable. For whatever reason, you make me feel comfortable’.

‘Thanks’ he said.

We sat up on the bed and looked at each other for a moment.

‘By the way. There’s one more thing I have to tell you.’ he said.

‘What?’ I asked.

‘I have a girlfriend’ he responded, ‘But it’s just that I have some needs that she just can’t fulfill’.

I’m not sure why he had to tell me this before fucking me. What difference was it going to make? But it’s something I had noticed before. When a guy is cheating, regardless of whether his partner is a guy or a girl, he often feels the need to confide to rationalize why it’s OK to be doing what he’s doing. Kind like if my shoulders were going to take some of the guilt off his. The fact that I have, hanging between my legs, something he enjoys and that his girlfriend can’t provide was probably his justification for why being here with me tonight wasn’t really cheating. Whatever!

While we had been making out, sucking each other, rimming each other, sensing each other’s skin, my body had completely relaxed. Justin had put me entirely at ease, like if this had all been a long massage at the spa. My hole was looser than it has ever been, even though neither him nor I had done any fingering to it. Not that my hole was anywhere close to being as loose as required for when his monster cock would be rammed into it. But it was as loose as it would ever be.

I grabbed the bottle of lube, and I had no difficulty inserting three fingers. Normally I struggle to get past a second finger, no matter how much fingering I do before. It was as if my hole knew that it was going to get sodomized regardless and could either do it the easy way or the hard way. But since the outcome would be identical either way, any resistance would be futile and would only lead to unnecessary pain. I felt that if my hole surrendered without a fight, everything would be OK.

I grabbed a condom and gave it to Justin.

‘Sorry, dude, I don’t have any Magnum’ I told him, ‘It’s not like I normally need one’ pointing at my skinny dick. ‘Guys with a big schlong are normally happy to bring their own. I hope it fits you’.

‘Sorry’ he said ‘I don’t normally use condoms.

‘Sorry, man’ I replied, ‘It’s already a big deal for me to let you fuck me. We’re not doing this without a condom’.

He put the condom on his massive log. It was clearly not the right size rubber. His dick looked like a fat girl who insisted on wearing a daisy duke and a petite tank top. But he managed to roll it all the way down his shaft. These things are designed to stretch anyway. I made sure I poured ample volumes of lube on his pole.

I laid on the bed, my stomach lying on the bed cover, my legs spread apart, my dick lodged under my stomach, and my balls hanging beneath my exposed hole. I brought my hands to my butt cheeks, spreading them apart for him, and opening my frightened hole to allow his monster to tear it apart. I couldn’t believe that I had put myself in this position. Not the literal position of lying on my stomach, but the position to let a guy with such a massive cock explode my inexperienced hole. And I didn’t just agree to it. I’m actually the one who asked for it. The last time I had let a guy fuck me was Aaron. At the time, I had already hesitated because Aaron’s dick was a bit thicker than mine. But with Justin, it wasn’t just ‘a bit thicker’. He had one of the thickest rods I’ve ever seen, and he was about to stuff all of it in my shithole. But I couldn’t back out at this stage. And even though my mind was having second thoughts, the rest of my body was craving for the upcoming fuck fest.

Justin positioned his big frame above mine, as if he was going to be doing push-ups over my back. He placed the tip of his dick over my hole, and he rammed it all the way down, in just one plunge. Since it was his first-time ass fucking, boy or girl, he probably didn’t realize that assholes are not designed to admit a guy’s manhood the way pussies are. And even then, I’m sure there were some girls who asked him to take things slow with a sausage like his. Or maybe he was fully aware of it but just didn’t care. The suddenness of the invasion tore my hole apart. I had just assumed he knew how much he was packing and would have gone easier on my hole. My mouth reached for the pillow in front of me and I bit into it while screaming like if a real-size eggplant had been stuffed into my hole. My crying was muffled by the feathers in the pillow. Justin didn’t really give my ring any chance to adjust to his girth and remained completely oblivious to my screaming. He started drilling my violated hole right away, fucking me unapologetically, just like if the mismatch between the tightness of my hole and the thickness of his tool wasn’t apparent to him.

My mind was screaming ‘I knew it, I knew it, I knew it!’ while my body was apologizing to my mind for dismissing all the warning signs. But it was my body that ended up enduring the punishment it had been craving for. Whatever little self-esteem I still had in me, after allowing him to turn me into his bitch, stopped me from begging him to stop the assault. I was going to take it like a man and not turn into even more of a pussy than I had already become!

Justin kept pounding my man cunt, ignoring my screams, and showing no mercy. There would be indelible teeth marks in the pillow when the night was over. He was doing what he had learned to do: fuck a hole and fuck it hard. I was just lying there like a starfish, enduring a dude’s uttermost humiliation with zero resistance. He had full control over me and had made me his whore.

As the pounding continued, the pain of each thrust started to subside a little. Not that Justin was going any easier on me, but my ring muscle was finally getting used to the stretching. The size of his cock filled up every space inside my guts. His cock had no room to get passed by my G-spot without banging it along the way. My G-spot was taking a beating, but it was a lot better equipped to handle it than my ring muscle had been. And by now, even my ring muscle was starting to enjoy the relentless pendulum of Justin’s joystick. What had started in excruciating pain was progressively turning into pleasure.

Even though he had zero experience in anal sex, either with a guy or a girl, Justin was incredible at it. Just like I’m sure he was incredible at vaginal sex too. Some guys are just natural fuckers and can adapt to whichever situation they face. Sure, he had an unfair advantage with his massive endowment. But it wasn’t just his cock that provided me all this pleasuring. He understood how the human body reacted to all the possible stimulations. He was hitting all the right spots inside and outside my hole. He was gently biting my ears and kissing the back of my neck, sending shivers all over my body.

At one point, he let go of the push-up position and rested all his body weight on mine. He passed his muscular arms underneath my arm pit and started pulling my shoulders up and my neck down. I believe it’s a wrestling move called the Full Nelson. He must have been a wrestler in high school too. Boy, he would have been hot in his wresting singlet! With his big bulge stretching the fabric, on display to both his opponent and the onlookers. This new position restricted my movement even further, his strong hands pressing on my neck and pushing my face against the pillow. I was even more vulnerable than I already was before. This new position changed the angle of his penetration, allowing his cock to reach even deeper inside me, and explore new parts of my insides. As a guy whose dick length didn’t match his massive girth, he must have learned this technique, which allowed him to fuck deeper than a 6 ½-incher otherwise could have.

He adjusted his speed and motion from time to time, always keeping me on the alert as to where he would strike next. At one point, he started jackrabbiting me. I never knew someone’s hips could move that fast. I would have loved to be a fly on the ceiling, admiring the speed at which his ass was rocking. Both our bodies were vibrating under the fury of his back-and-forth movement, bed included. Every thrust was sending shock waves that reverberated through my entire body. I was convulsing like if his pole was 600 volts. My nipples were rubbing against the bed cover with every thrust of his big fat cock banging inside me. All I could do was grumble under the assault with a long ‘ah-ah-ah-ah-ah-ah-ah’, my voice vibrating in unison with his banging. If he continued like this much longer, his condom would start smelling like burnt rubber, as if a teenager had gone on a joyride on an empty parking lot. My cunt was having a joyride of some sort too. But he eventually throttled down to a more sensual motion. Fuck, he was good!

The other parts of my body that were taking a pounding were my hairy balls. Given Justin’s position right above me, his big balls were swinging back and forth, smacking mine with every thrust. Since my poor balls were laying on the bed cover, right underneath my battered hole, they had nowhere to seek shelter. They were fully exposed, taking a beating from the slapping of his big balls. But I was turned on by the sound of it, the sound of his big balls slapping against his thighs on the ascent and loudly smacking my balls on the descent. It was so fucking hot!

I normally like to make the other guy cum before me. Being the one cumming first is one of my pet peeves, so to speak. But Justin’s fucking was on a completely different level. Trying to resist the pleasuring of my hole by his monster cock was an exercise in futility. Justin’s tool was going to make me explode first. There was no question about it. The alternative had flown out the window the moment I resigned to submit to him. It never even crossed my mind that I’d be able to make him cum first. My cock had been leaking precum the whole time. So much had already been oozing out that it had started to form a gooey puddle in which my dickhead was soaking.

The brute force of his big fat cock relentlessly pounding my hole combined with the stimulation of my dick rubbing between my stomach and the gooey bed cover would turn out to be enough to drive me over the edge. My hands were grabbing his butt cheeks, kidding myself that I was somewhat softening the vigor of his assault. But in reality, my arms were just another avenue through which the convulsions were penetrating my whole body. I felt the pressure building inside me. My man juice was churning within my balls and, once they’d get passed the boiling temperature, my jizz would be propelled through my dick canal faster than the speed of light.

My cock finally erupted on the bed cover underneath my body. A first massive load, followed by a second and a third one. I was cumming hands-free for the first time (and the only time) in my life. It felt incredible, like nothing I had ever experienced before. It’s not like I was cumming solely from Justin’s cock pumping my load out of me. My cock had been rubbing against my stomach and the bed cover since his first assault on my hole and had received its fair share of stimulation, even with no hand involved.

But this orgasm felt completely different from what I had experienced when being fucked up the ass before. It was not my first-time bottoming. I had already felt the sensation of my ring being stretched and my G-spot being pounded. But it seems like before, the main focus was still on pleasuring my cock. The anal stimulation was secondary, sort of the cherry on the cake, no punt intended. The added pleasuring up the ass was just a booster to my cock, the same way twitching my nipples was. But this time, my cock had taken a back seat. The bulk of the attention had been on my back door and Justin’s massive cock beating it to submission. That’s probably why the mere rubbing against my stomach and bed cover had been enough to set my cock on fire.

I’m normally not a screamer, but this time, screaming I did. And not just once. Not just the ‘Aarrgghh’ that accompanies the initial orgasm. I screamed with every stab he inflicted into my hole, each stab pumping yet one more load out of my balls, until they were completely hollowed out. I may have made some dirty talk, but I don’t even remember. Since my jizz had nowhere to go, it started pooling between the tip of my dick and my belly button, drenching the bed cover, my stomach, and my pubes. I ejaculated so much spunk with my dozen or so loads that it formed a puddle that would be hard to clean out. The Oxi-Clean guy would probably have to think twice before promising his miracle product could clean that bed, like nothing ever happened.

But Justin did not stop hammering my hole after he had drained every ounce of spunk out of my balls. He kept using my cunt for his own pleasuring, ramming his log in and out until it was his turn to climax. Once he got close, he pulled out in one drive, retreating from my hole just as suddenly as he had invaded it. The abrupt exit produced a small pop, although not quite like the sound a cork being pulled out of a wine bottle. This caused me to gasp. My hole was filled with a sensation of emptiness that I had never experienced before. But I didn’t have time to reflect on this for very long. Although I had nothing left in me – no punt intended – Justin on the other hand was still full of spunk. And I was anxious to see where he’d be flooding me with his jizz.

He ripped the condom out of his cock in one go, which was no small achievement, given how tight the rubber was on his massive rod. He placed his cock in-between my thighs, pointing it downward toward my aching hole. His cock spit a first long load, which stung my hole with the force of a pressure washer. His second load wasn’t nearly as strong but even more massive, followed by several others. He was creaming my pie with his piping bag. Once he was done milking his dick, I started feeling his gooey liquid dripping from my hole down to my balls.

Justin looked at my drenched hole with the look of satisfaction after a job well done. I could tell something was crossing his mind.

‘Don’t you even think about putting it back in without a condom!’ I warned.

He got a bit disappointed when he heard me say that as that was exactly what he had in mind. But he obliged. He brought the tip of his dick to my ass crack and used my crack to wipe out the remaining spunk still dripping out of his piss slit. As if all the domination he had exerted over me tonight wasn’t enough and he needed to humiliate me one last time by wiping himself on my ass. He let out a loud breath and collapsed on the bed right next to me.

‘So, how was your first time fucking a dude?’ I asked.

‘It was great’ he replied, ‘your ass is a lot tighter than a pussy’.

‘Well, not anymore’ I said ‘I’m gonna need anal reconstruction after what you just did to my hole’.

‘Was it that bad?’ He asked.

‘No, it was incredible’ I replied. ‘I came hands-free’.

‘Oh yeah! I was gonna ask you about that. I thought the guy being fucked still had to jerk his dick’ he said.

‘Normally, he does’ I replied, ‘just consider you did an amazing job’.

‘Thanks’ he said, kind of blushing.

Justin was a real gentleman. You could tell his mom had raised him well, or at least had tried her best to. If it had been me who had been able to make a guy cum hands-free, especially a guy my age, I would have been bragging about it until the end of time.

We both laid on the bed, catching our breath and smiling at each other. I grabbed a couple of tissues to sponge out the puddle of cum I had discharged on the bed cover. I also wiped out of the cum he had discharged on my ass. He said he didn’t really need to take a shower right away and could do that when he got back home. He grabbed his clothing and got dressed.

He left and said ‘Thank you’. Truly a gentleman!

I responded ‘Thank you too’.

I locked the door behind him. I went to the bathroom and looked at myself in the mirror. ‘Fuck, what just happened?’ did I ask out loud. I took a shower and went straight to bed afterward.

The following day, I had a fourth guy lined up, but he ended up cancelling on me. For once, I was grateful the guy had flaked out. My beat up hole obviously needed some quiet time. I would probably be crying when taking a shit for the rest of the month. But it wasn’t just my hole that needed rest. It was my whole mind and body. I needed time to process what had just happened to me. A somewhat dominant top had just been handed the beating of his life. But I had also experienced the most unique orgasm I’ve ever felt. I now had to figure out how to reconcile these two conflicting feelings inside me. I still think I’m a top. I still like being dominant. But I really enjoyed getting fucked by Justin.

Luckily, I didn’t have to travel next week, and anonymous sex would take a back seat for a few days. Enough time to figure out what next sexual prowess I would want to experience the week after that.

by Jeremy Miller

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