Anonymous encounter: The Texas DILF

I’m a liar!

Although my driver’s license says I’m 42, my online profile says I’m only 36. Just a little white lie to make sure I still have a chance to get laid. That 4 is a killer when you’re hunting for young dick. But with my smooth swimmer’s build, I can still pull it off. And because my profile says I’m looking for younger, I get my fair share of guys in their 30’s and 20’s, even as young as college kids. Because enough young dicks are flocking my way, I usually don’t even bother responding when I get swiped by an older guy. It’s not that I don’t like older guys, when they’re still in shape. Brad Pitt is almost 60, and I’d gladly oblige if he ever spread his legs for me. Not that he ever would. But unfortunately, very few guys who are Brad Pitt’s age still have Brad Pitt’s body. Very few guys in their 30’s still do for that matter.

This week, I had to go to Dallas for work. And ahead of my trip, I switched my profile location to Dallas, the way I normally do before a business trip. Because I was fresh meat on the app, I got swiped by a few prospects, some hot, some not so hot. And surprisingly, one that caught my eye was a 41-year-old married guy. I normally would have overlooked a guy five years older than my fake profile, but there was something about this married man wanting to experiment, which caused a little stiffness in my underpants when looking up his profile. It’s not often you can land a real DILF, and this one looked like he was cherry.

When I think of the ‘I’d-Like-to-Fuck’ part of a DILF, I think of a guy in his early 30’s running shirtless in the park while pushing a stroller. Droplets of sweat running in between his shinny pecs. His shirt hanging on the side of his shorts. Bonus points if he has a light trimmed beard. There’s something that turns me on about a guy who is now a real man, with his head on his shoulders, but still has the stamina of a young buck, and the living proof that his dick and balls are fully functional. And I imagine them bouncing in his shorts while he’s running.

The DILF who swiped me looked like he had the D part better covered than the ILF part. Early 40’s instead of early 30’s. A stomach probably not as flat as it once was. But his pictures showed he still had it and wasn’t a complete stranger to the weight room. And given how amateurish his pictures looked, I knew there was no photoshop involved. But even though he was more D than ILF, he still looked fuckable enough for me.

Given he was new to the gay dating thing and very much on the down low, he had no face pic and no dick pic. But he had invested the time to write ample details about where he was in his life, having wanted to experiment for some time (like forever!), and being ready to make the jump. And I was happy to make him jump. Jump on my cock that is. The fact he was cherry and had exposed some vulnerability in his story made me want to meet him even more. We agreed on a time that worked for both our work schedules and, on Wednesday evening, he knocked on the door of my hotel room.

‘Hi, I’m Mark’ he said.

‘Jeremy’ I replied ‘Nice to meet you’

‘Nice meeting you too’

He was wearing khaki pants and a blue golf shirt, showing off his nice hairy forearms. Not gorilla fur, to the point you can’t see the skin underneath, but the right amount of hair you’d expect from a real man. His golf shirt had both buttons unbuttoned and I could see a little bit of chest hair in the narrow part of the V. He had short brown hair and piercing blue eyes. He was clean shaven, but because it was getting late, you could see his 5 o’clock shadow starting to grow off his manly face. At first glance, he looked like he was in sales. Not a sleezy used car salesman at a fly-by-night dealership, more like a large account executive or a regional director of some kind. Working hand-in-hand with large account executives myself, I can spot them from miles away. I bet he was selling industrial equipment, like electronic valves or robotics. And his job probably consisted of nurturing client relationships by taking them to dinner and the occasional round of golf. That would explain his outfit.

He reeked of suburbia and looked like your typical middle-aged dad. He might as well have had a white picket fence tattooed on his forehead. Add to that a Toro lawn tractor and a Webber grill. But that’s kind of what I had signed up for and was part of the appeal: taking a typical suburban dad and guiding him to the dark side.

He was on the shorter side. Probably 5’9” vs. my 6’2”. Nice summer tan. If I had to guess, he was probably a bit heavier than my 175 lbs. But he wasn’t fat or anything. He was just stocky, while I’m more on the lean side.

Part of me was curious to know his life story and what had prompted a 41-year-old married man, father of three, to put his profile out there and start hunting for dick. But I also suspected his story would involve some component of a failed marriage and I had zero interest in hearing about that. So, we kept the conversation casual: Weather, sports, Dallas. He was originally from Missouri but had moved to Dallas for work after getting married and now called Texas home, although if you weren’t born in Texas, you’ll never be a true Texan, ever. He mentioned having been on his high-school baseball team. And he was a catcher, of all positions. You just can’t make that shit up! But the positive point is that catchers usually have thick thighs and a muscular butt, which he still had. I’m sure he looked great in his baseball uniform back in his high school days. I would have been happy lending him a hand to adjust his cup.

Since I didn’t expect him to make the first move, I took the lead and I removed my T-shirt, exposing my completely smooth torso. He followed suit and removed his golf shirt, showing off his nice hairy chest. If there was such a thing as the ‘right’ amount of hair, he would be it. His chest hair formed a nice oval covering his pecs, a bit past his nipples on both sides. It stopped a couple of inches south of his Adam’s apple. With two buttons unbuttoned, you could see the upper part of it. But with only one button, you couldn’t really tell. He had a thin dark trail plunging from his chest hair to his belly button. And from the belly button down, a thick treasure trail, which was kind of lost in a patch of hair that covered all of what probably used to be a 6-pack in the frat house but had since become a little beer gut. But he wasn’t one of those middle-aged dads who had completely given up on his body. You could tell he was still trying to keep a flat stomach. And his arms and chest looked like he could still bench more than his own weight. His hair continued to the waist band of his boxer briefs, and I expected to find a bushy bush underneath. His nice hairy chest provided a stark contrast to my hairless torso.

To my big surprise, he also had a tattoo on his chest. Apparently, the now good suburban husband used to have a wild side in college. But back in the days, tattoos weren’t as mainstream as they have become with the newer generation. Back when he was in college, tattoos were still frowned upon by recruiters and he was thoughtful enough to get a tattoo on his chest, a location where he could easily hide it underneath his shirt. Unless he took his shirt off, nobody would ever know. So, he did experiment in college! But with ink, not with dick.

His tattoo was pretty cool and was done by someone who knew what they were doing. Instead of the picket fence tattooed on his forehead, he had a cardinal tattooed on his right side. The cardinal was perched on a baseball bat with the head of the cardinal close to his shoulder and the bat handle and tail of the bird in-between his pecs. He probably had the tattoo made when he was younger and didn’t have as much chest hair. The head of the cardinal was still clearly visible close to his right shoulder, but the tail of the bird was now somewhat lost in his chest hair.

I complimented him on his tattoo. He blushed a bit. And we started making out. Although he obviously knew how to kiss, I had to take the lead as he was more out of his element than I was. I grabbed his bubble butt with both hands and pressed his body against mine. I loved the tickling of his chest hair against my smooth torso and his 5 o’clock shadow grinding against my baby face.

I then unbuttoned my pants and they dropped to my ankles. I was wearing my sexy Andrew Christian briefs; the ones that make my dick look bigger than it really is. I always wonder whether that’s the smart thing to do or not, since the whole purpose of my anonymous encounters is to take my briefs off at some point, after which my dick looks the size it really is, with no fabric or engineered pouch to hide behind. But I just like feeling sexy before the banging. My dick was already blood engorged and was pressing against the fabric. I took his right hand and guided it to my shaft, which he started tracing through the fabric. While he was doing that, I went for his pants, and they also dropped to his ankles. His white boxer briefs were not nearly as sexy as my Andrew Christian briefs. Probably something his wife had thrown into the Costco cart, while shopping for cereal and pork chops. But I could tell his dick was starting to expand as well and I started playing with it. I also noticed he indeed had the nice thighs I expected from a former catcher: muscular and hairy.

I kneeled in front of him and started cupping his package in his boxer briefs, first with my fingers and then with my lips. I could see the outline of his dick, still pointing downwards but pressing against the fabric, begging to be set free. I could size up his balls behind his shaft. There was clearly a lot going on in there. I lowered his briefs and his cock sprung out, slapping against his stomach, and rebounding down, to stabilize in a more or less horizontal position. Because the guy was short and stocky, I expected his dick to match. It turns out it was the exact opposite. His dick was longer than mine: A solid 6 inches vs. my 6-inch wannabe. But it was skinnier, not by a lot, but still a bit skinnier.

‘I just don’t have the girth’ he said, in a somewhat apologetic way.

When saying these few words, his voice conveyed both guilt and sorrow, as if his skinny dick was a contributing factor to his fledging marriage. This short sentence was a tacit admission that he couldn’t be as good a husband as he wanted and that, had he packed a bigger shlong, he could have made his wife happier. In a weird way, his pencil dick was one of the reasons while he was standing naked in front of me, searching for the intimacy his wife no longer provided.

‘That’s OK. I don’t have the girth either’ I replied.

I never make comments about a guy’s package, unless it’s a monster cock, in which case I compliment the guy. I know how your dick is such an important part of what defines you as a guy. I don’t want to throw salt on a guy’s insecurities. And not having a 9-inch nail myself, I’m in no position to brag anyway.

But underneath his skinny dick hung a huge pair of balls. Clearly much bigger than mine and probably the size of golf balls. I bet these things could produce enough juice to flood a basement, when manhandled the right way. I would find out soon enough. How do guys even walk with balls like that? Especially when they also have big muscular thighs that fill up their pants. The size of his balls accentuated the skinniness of his dick and made him the epitome of long and skinny. And at the top of his shaft stood a big bulging dickhead, which size was a good match to his big balls but was somewhat disproportional vs. his skinny pole. It made his dick very mushroomy and kind of looked like Darth Vader’s helmet, but in red.

I know nothing about lady parts. I’ve never been anywhere close, nor do I plan on ever going there. But I would think his big dickhead could do some damage, providing enough friction to turn a lady into a street whore. I’m sure early on in their marriage, his oversized dickhead was able to extract some screaming out of his wife, even if the screaming became more and more elusive as gravity sunk into their marriage over the years.

I took his dick in my mouth and started sliding my lips up and down his shaft. I immediately got a whimper out of him. I bet his wife hadn’t sucked his dick for a while, if she ever did. I only worked the upper half of his pole, twirling my tongue around his big mushroom head. This was enough to extract some regular ‘Fuck yeah!’ out of him. At the base of his dick was a dark bushy bush. The manscaping craze had not yet reached the Dallas suburbs, from what I could tell. He smelled like a suburban dad, a mix of Old Spice deodorant and no name body wash that his wife bought for him at Costco.

After a couple of minutes of me sucking his dick on my knees, we took it to the bed. I laid him on his back, got on top of him, and resumed the kissing. I was still wearing my Andrew Christian briefs, which were getting soaking wet from both his precum and mine. Since nobody was really paying attention to my sexy underwear anyway, I took them off and my hard dick started grinding against his.

Unlike him, I had seriously manscaped, leaving just a little patch of hair around the base of my dick, kind like a thin mustache. When I was 12 years old, I went to the public swimming pool with a buddy who was a couple of years older. While we were changing in the locker room, I took a peek at his dick. I had not reached puberty yet, but my friend already had. He had just started to grow a thin line of pubes, surrounding the base of his shaft. I had never really seen pubes before, and it caught me by surprise. Although I had always wondered what his dick looked like and whether it’d be bigger than mine, I had never really given any thought as to whether he would have dick hair or not. But when I saw that skinny patch of black pubes, I thought that was the coolest thing ever. And for months to come, I anxiously waited for my body to eventually reach that stage and grow pubes too. That image really stuck in my head and, from time to time, I like to recreate that look, which makes my dick look like an early teenager who just reached puberty. It basically makes me look like a 40-year-old twink. The contrast between my manscaped bush and his dark jungle fit the contrast between his hairy stomach and my smooth one.

I straddled him, pressed our two cocks against each other and started jerking them in unison. After a few strokes, he said: ‘My turn!’. I let go of our cocks and his hand took over. He jerked his hand up and down our shafts, like if our two cocks were double penetrating his fist. His blue eyes lightened, and he had a big smile on his face, like a kid who just received a puppy for Christmas and asks: ‘Is this for real?’

When you have an average sized dick, you’re used to having the top of your index reach the knuckle of your thumb when you jerk off. But here, having his middle finger not able to reach the tip of his thumb, because our two skinny dicks joining forces had the combined girth of one massive tool, must have felt like magic to him. Jerking two dicks together is the closest you’re ever gonna get to knowing what it feels like to have a big dick. At one point, he even used both hands and was in Heaven.

He was really into it and was stroking our dicks vigorously. And since his was a bit longer than mine, his finger was rubbing against the upper edge of my dickhead with every stroke. The rubbing was a bit painful, but I didn’t want to say anything since he looked like he was enjoying himself so much and I didn’t want to be the party pooper. Besides, the slight discomfort distracted me from the stimulation. And the last thing I wanted was to cum right here right now when I had much grander plans for the evening.

He truly was a newbie to man-on-man sex. When he first showed up, I wasn’t sure what to expect and how things would progress. I figured that jerking each other off was as far as he’d be willing to go. But now, he was eating in the palm of my hand. If I played my cards right, he would be begging for my cock later. And I was ready to give him the full Jeremy experience.

‘Let’s slow down’ I said. I grabbed his hand and stopped the jerking. For a second, he had that sad puppy look on his face. But I didn’t let him ponder for too long. I grabbed his bent knees, spread his legs apart, exposing his hairy virgin DILF hole and went down on him. He probably had never been rimmed before. If his wife didn’t bother sucking his dick, there is no way she would have dug her nose and tongue into his hairy ass crack.

To be perfectly honest, I don’t enjoy burying my nose in a guy’s crack as much as I enjoy sucking his dick. But I just wanted to test his reaction. And after the initial surprise, I got some whimpering out of him, which let me know his cherry was fair game. So, I doubled down on eating his ass. I alternated licking the edge of his ring with digging my tongue as deep as I could, causing his whimpering to get louder.

‘Fuck, that feels awesome!’ he said. ‘Please never stop’.

I kept going at it for a while and eventually took my head out of his ass, looked him up in the eyes, and asked him: ‘Are you ready for the big jump?’

‘Yes, I want your dick in my hole’ he replied.

I grabbed a condom and a bottle of lube, which I had placed in the drawer of the nightstand and rolled the condom down my shaft. I put ample amounts of lube, both on my dick and in his hole, using my middle finger to loosen him up.

Virgin holes are supposed to be tight. But his was not. Although his hole had never been fucked by a real dick before, it felt like it had already been explored by something much bigger than my 6-incher.

‘Well, well, well!’ I thought to myself.

In addition to his lawnmower and his Webber grill, the DILF also had a dildo collection apparently. That is really the only explanation I could think of. And we are not talking about an entry-level butt plug. It had to be something much thicker, and possibly much darker than that. And some triple A batteries might have been involved as well. Which led me to wonder where a married man, father of three, could possibly hide a dildo collection. Did he hide them in his toolbox in the shed? Was there a secret chamber under the stairs? Did he hide them under the coach in his mancave? How could he be sure that his wife or teenage son would not stumble upon them?

It didn’t really matter at this point. His hole was loose enough that it would accommodate my average sized dick with no further prepping. I lined up my cock in front of his hole and slid into it like it was butter. I went balls deep in one thrust and he didn’t even cringe. He had definitely had a foreign object up his ass before. I took it as a sign that I could pound him hard, with no restraint. And pound him hard I did!

I fucked him in every position you can think of.

I started ass up, face down buried in the pillows, with me drilling him from behind, my thighs spread on each side of his muscular ass, and my log stuffed in his hole.

Then him on his back, ass hanging off the edge of the bed, with his ankles on my shoulders and me standing up, reaming my cock in his hungry hole. I was long-dicking him, or rather 6-inch-dicking him, using all the length that God gave me, pulling my cock fully out, and then ramming it back in as deep as I could. I rarely go for long-dicking because getting back in can be tricky and kind of kills the mood. But with a loose hole like his, the re-entry was easy. His grunt, every time I bottomed out, provided encouragement for me to go even harder on the following thrust. His dildos might have loosened his ring, but they didn’t desensitize his prostate. He was loving it and kept shouting lines he picked up from porn movies:

‘Oh yeah! Fuck that ass!’

‘Your dick feels so good in me!’

‘Keep fucking that hole!’…

… and other obscenities I don’t remember.

Then, we switched to him lying on his stomach, and me jamming my cock from behind, like if I was doing push-ups; alternating jack rabbit sessions, drilling his ass as fast as I could, followed by more sensual fucking, with me exploring his insides while gently biting his neck, which made him purr like a cat.

Then me lying on my back and him riding my cock cowboy style, with his pencil dick swinging from left to right like a windshield whipper and his big balls bouncing up and down between his legs.

There’s something to be said about older guys and how long they can last, because he was clearly overwhelmed by the whole experience, but still managed not to offload after a few strokes, like a teenager would have. I was also edging him to make him last longer. Whenever his increasing moaning indicated his stick of dynamite was ready to explode, I would pull out, let him cool down a bit, and start fucking him in another position.

I finished him off missionary style. These priests knew what they were talking about when they recommended that position, although it was likely for different reasons. I put a pillow under his ass, spread my thighs wide, underneath his butt cheeks, spread his legs around my waist, and shoved my hard dick back into his DILF hole. That angle gave my dickhead plain access to his G-spot, which I was hammering from underneath, while jerking his dick with my right hand. He first had his arms spread, with his hands under his neck, giving me a nice view of his hairy armpits. He eventually removed them to start playing with his nipples.

He was enjoying the railing and I was panting like a bulldog chasing a ball in the sun, sweat dripping along my face. I could see he was getting close. He started moaning faster. The same moaning I recognized from all the other positions earlier. But this time, instead of slowing down to let him cool off, I doubled down on the pounding and went full throttle. I decided he had been a good boy and should be allowed to unwrap his presents. He was mine and I was going to drive him over the edge.

‘I’m getting close. I’m about to cum’ he said.

‘Go ahead. Cum for me!’ I replied.

And cumming he did! He let out a cheering scream as if he had scored a walk-off homerun at the bottom of the 12th. And fireworks started shooting out of his cock. His golf size balls probably had several days’ worth of DILF juice that neither his wife nor his right hand had bothered milking. But more than a few days’ build-up, what was shooting out of his cock were 20 years of pent-up frustration. The thrill of feeling another guy’s hardon up his ass, providing the pleasuring he had always wanted, but had never experienced until now.

Volley after volley of DILF juice shot out of his long skinny dick and landed all over his body. The first glob landed on the cardinal and probably drowned the poor bird. I expected to see the bird shake his feathers like birds do when they’re bathing in a puddle. But instead, more volleys kept shooting out of his cock, adding to the jizz already pooling on his stomach. Most of the jizz landed on his chest, slowly percolating through his chest hair. One shot landed on his chin. Others landed on his hairy abs.

The scene was hot as fuck, and I knew I wasn’t gonna last much longer either. I just had to last a few more strokes, enough to keep hammering his G-spot while he was experiencing the orgasmic explosion of his life. Once he was done for good, I withdrew in one quick thrust, which made him gasp, and I tore the condom out of my dick.

As I started jerking my pole, he asked me: ‘Can I swallow your load?’

‘Of course, you can’ I replied.

He didn’t have to ask me twice. I brought my dick to his mouth, and he engulfed it like if he had been handed a water hose after 40 days in the desert.

‘Oh yeah! Suck that dick!’ I ordered.

‘Do you like a dick in your mouth?’ I asked.

‘Huummfff’ is all he could respond, while he kept working my rod hungrily.

Every guy more or less knows how to suck a dick. It’s just a matter of whether you really want to or not. And he really wanted to. He wanted my cock in his mouth. He had wanted it his whole life. All these instances, at the 4th of July party in his backyard, when he and his neighbors dropped their shirts off while drinking beer in the Texas summer heat. Watching his buddies’ sweaty chests shining in the sun but trying not to get caught staring. With the added insult of having to flip sausages on his Webber grill, when the sausages he really wanted, he couldn’t have.

Given how close I already was, before he even started blowing me, I knew I wasn’t gonna last very long.

‘I’m gonna shoot’ I warned.

That only made him go faster. I felt a rumble churning through my balls and my load travelling through my shaft, like a herd of buffaloes chased by a pack of wolves through a narrow passage.

‘Here she comes! I shouted.

I grabbed the back of his head, pressed his nose against my little patch of pubes, and moments later, my dick exploded in his mouth.

‘Fuck! Fuck! Fuck!’ I screamed.

I came so hard that I thought I would drill a hole in the back of his throat and see my load come out on the other side and splash against the wall, like a splatter of blood on a CSI episode. But he took it like a champ and swallowed it all. As my second volley blew out, he went back to working my rod and kept stimulating my dickhead, which was already so sensitive. It drove me insane. The more I kept cumming, the more he kept sucking, until my balls had no more juice left in them.

I have no clue how much I shot. My balls might only be half the size of his, but he drained them like a pro, and I probably filled his mouth with just as much jizz as he had shot on his stomach earlier. His milking probably turned my balls from grape to raisin inside my nut sack.

I collapsed on the side of the bed and we both stared at the ceiling. He had a big smile on his face. The same smile a teenager has after losing his virginity and turning into a man. Technically, it wasn’t his first time, but it kind of was at the same time.

After a few minutes, I broke the silence and asked him: ‘So, how was your first time with a dude?’

‘It was incredible’ he replied.

‘Better than a dildo?’ I asked

‘Better than a dildo’ he replied.

We both smiled. We understood each other. No need to expand.

He looked at his spunk-covered stomach and said: ‘I probably need to shower before getting back home’

We both made our way to the bathroom. Even though I wasn’t covered in jizz like he was, since my jizz ended up in his mouth, I still needed to rinse off the sweat from all the pounding. The bathroom didn’t have a separate shower, just a small bathtub with a curtain. It was kind of cramped with the two of us in there, which made the scene even more intimate. His dick had gone soft but mine was still at half-mast. The combination of our bodies rubbing against each other in the cramped space and the steamy hot water running down our bodies caused my dick to get back to life.

‘I still have a little bit left in me’ I said. ‘Do you mind if I jack off?’

‘I can help with that’ he responded.

I turned around to face the shower with him standing behind me. He grabbed my waist with his left hand to press my back against his hairy stomach and grabbed my hardon with his right hand. I squatted a little bit, so that my face would be at the same height as his. The hot water was running down my stomach and my legs while he was kissing my neck from behind and jerking my dick at the same time. I tilted my head back to be able to kiss him. I grabbed his muscular ass with my hands. And while his dick never got fully hard, I could still feel its tip tease my ass crack, while he was briskly jerking my dick, applying just the right amount of pressure. I felt so secure in his muscular arms that I wished this moment could last forever. But it didn’t. I was so relaxed that I came in less than a minute.

‘Oh yeah!’ I shouted, while my dick shot several volleys of white spunk into the hot water stream.

‘Fuck yeah!’ he concurred.

Although I didn’t shoot nearly as much as the first time, I had still underestimated my trusted pair of balls, which apparently still had a little bit of spunk left in them.

I turned around, grabbed his face with my hands and kissed him passionately while hot water was running down our faces.

Amazed by the fact I could still cum a second time, less than 20 minutes after my first load, he said: ‘Boy! I wish I was still in my 30’s.’

‘What a difference five years make’ he added.

‘Yeah, what a difference!’ I repeated, leaving it at that.

We both stepped out of the bathtub and got dressed. He thanked me again, grabbed his briefcase, and walked out.

I thought to myself that the expression ‘walk of shame’ had never been more appropriate: Getting back home to his wife and kids with a sore asshole and cum in his mouth. He would have a lot of reflecting to do on what that meant for his marriage, for his sex life, and for his life in general. But for me, he had been a great fuck.