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This story begins like many others: I was horny.
It was a Friday and work was going particularly slow, so I was on my phone hunting for some after-work booty. All my regular boys were tied up, and not in a good way, so I was stuck searching for someone new.
I didn’t have to look long before a cute cub, I’m calling him SlutCub for now, was hitting me up on Scruff. Short haired, fuzzy, and submissive, he was in town for work and staying at a hotel near my office. We talked for a bit, discussing specifics and kinks, and set up a meeting time after work. Once I was done at the office I drove right over.
I walked in and made my way to the elevator. I always wonder if the hotel employees can tell why I’m there when I just walk past them and make for the elevators. Wouldn’t stop me even if they did, of course. As I walked the halls I passed gaggles of teenagers, presumably here for some sort of school conference; no idea what’s going on in the rooms next to theirs.
The door was open and as I let myself in I was greeted with the site of a boy ass up on the bed, naked from the waist down. I shut the door behind me and kicked off my shoes as I approached him. I grabbed his ass with one of my hands and gave it a firm smack. I stood there, squeezing and kneading his cheeks for a few moments, before dropping to my knees in front of it.
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The holidays were over, but Daddy D and I still found ourselves unable to meet up regularly at either of our homes. A combination of roommates and busy schedules forced us to make do with what we could, leading to a lot of dirty pics and texts being sent back and forth. I became particularly fond of expanding my jockstrap collection and showing it off for him. All the while we checked for any openings in our schedules for us to get together.
Eventually, we lucked out and found a good night for the two of us to meet up. Both of our places were still unavailable though.It looked like we were going to have another fun night in a park together. Daddy sent me the address of a place nearby, and I hopped in my car that night to meet him.As I pulled into the parking lot, I could see it was a pretty innocuous looking park. It had all your usual trappings: some pavilions, a baseball field, playground. Then, further back, was a forest with a number of trails people could go on for walks. Not exactly like the trails from some of my camping adventures, but I’m sure they’ve seen their fair share of action.
I sat in my car for a few minutes until I saw Daddy park his own. I walked over and hopped in the passenger seat. We weren’t going anywhere, I just wanted to make out a little. Once we were done, we stepped out and made our way over towards the park proper.
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Christmastime was here, and I was looking forward to unwrapping a daddy shaped present. It had been a couple of weeks since our fun in the park, and I was very eager to see Daddy D again. Finally, we had managed to find a good time for the both of us. His place would be empty, and I would be able to spend the night.
And spending the night was important because the plans we had made would require a small amount of recovery time afterward. Daddy D had gotten his hands on some MDMA, also known as molly or ecstasy, and we were going to take some and spend all night fucking our brains out. I had done molly a handful of times before, though always in a more casual setting - never sexual. After hearing some of the things people had told me about having sex while rolling I was pretty excited to try it myself. MDMA is probably the “hardest” drug I’d ever be willing to do, and even then very sparingly and under certain circumstances. This just happened to be one of those circumstances.
I packed an overnight bag and headed over to his place. After I parked, Daddy lead me inside and straight into his bedroom. I set my bag down and got comfortable, taking off my shirt. Daddy came over and began to kiss me, taking off his own shirt before sitting on the bed.
“You ready for a fun night, cubby?” He asked as he reached over to his nightstand.
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I smiled as I entered Leo’s apartment for the second time. It was only a couple of days after our last meeting, though, unfortunately, his husband would be unable to join us once again. Lucky for him though, I had plans to make up for that.
After a hug and a butt grab I took a seat and tossed a pillow onto the floor, between my legs. “Kneel,” I ordered, pointing.
“Yes, daddy!” Leo chirped in response, quickly dropping to his knees.
I stroked his head as we chatted and caught up. Soon I begin removing my clothing, again handing them over to him to fold and put away, until I was down to only a jockstrap. Once Leo was back on his knees, I pulled him by the back of the head towards my crotch, his mouth automatically opening to take in as much of my jock-clad cock as he could.
I lazily ran my fingers through his hair as he mouthed at my cock, admiring the level of effort Leo was putting into even this simple task. What a good boy.
“I really wish Stu would have been able to make it,” I mused, referring to Leo’s absent husband. “Gonna have to do something to entice him, I think.”
Leo looked up at me with questioning eyes but said nothing, not wanting his prize to leave his mouth for even a moment.
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It was a couple of days after my evening with Daddy D. Since then we had been texting almost constantly, lots of pictures and dirty talk, the usual stuff. However, we were unable to meet up again as both of our places continued to be unavailable.
We weren’t going to let a silly thing like that stop us though.
We decided we would meet downtown. There are a few places there we could have some privacy, at least to walk around and talk. Nothing inappropriate of course, just innocently spending time together…
A nice, if not chilly, evening, I arrived downtown and parked before looking around for Daddy’s car. Once I spotted it I hopped in – we wanted some privacy after all, I just needed a place to keep my car for a few hours. We drove away from the skyscrapers and into a neighborhood. Daddy found a good secluded spot and parked, and we both got out to walk around a small lake nearby.
We strolled around the lake together. It was the early evening, the sun had just gone down and the streetlights were just turning on. As we walked, Daddy pulled a blunt from his pocket and lit it, and we passed it back and forth as we told each other stories from our pasts. He told me about what it was like in high school for him, while he was still in the closet. He was an athlete, which meant having to fuck a lot of girls. Hearing about that only made him hotter. Something about that “straight” guy mystique.
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Apparently this one posted to Nifty, but not here! Enjoy an extra story this week if you haven’t already read.
It was late one night when I first met a new pup, Leo. I was at a family event and chatting on Growlr, waiting for an acceptable moment to leave. You know, normal gay culture. A cute Latino cub, he and his husband lived nearby. Neither of them had much experience with kink, but were very interested in trying. Now, normally I’m a little hesitant to get involved with someone “new” to kink. Obviously, it’s important that the two of you can trust each other, and I’ve also had a few bad experiences with people who overestimated their interest. They don’t understand that when I say I’m going to tie them to my bed and fuck them stupid… they’re actually going to be tied down and fucked stupid.
But something about this pup was calling to me. So, once I can leave, I grab a Lyft and head to his place instead of going back to mine. I reach their apartment in the early evening, and Leo and I make our introductions after he let me in. His husband was working that night, so it was just be the two of us this time. Still, two new pups to play with.
Leo had rolled a few blunts for us, so I spark one up while as chatted. I don’t partake in a lot of substances, and you should always make sure you are in the right mindset and able to give proper consent when you are about to engage in some kinky play, but we wouldn’t be getting into anything too heavy, and weed just makes me really cuddly and handsy. Leo didn’t seem like he’d complain about that. As we smoked, we asked about each other’s personal lives, work, and kink. We had spoken earlier about some of what we were into, but I was still trying to read what it was Leo was looking for. I don’t think he even knew himself.
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I’d love to tell you I’ve got a boy in every town, just eager and waiting for me, but for the most part I keep my list of personal submissives relatively short. I like to ensure that the boys on I’m spending my time with are worth it. I have one particular boy from Texas, the son to my daddy, who frequently flies in to my location to visit his family. Unfortunately, that means we don’t get a lot of time together, as his family demands most of his time. We try to see each other when we can, but it’s difficult.
Tex is a few years older than myself, with tan Latin skin and thick, coarse hair covering his body. Most of our sexual interactions have been quickies in one of our cars or my apartment, often on a lunch break. And don’t get me wrong, I love public sex (as you have hopefully been able to surmise from some of my previous stories), but it’s hard to show a boy how you own his ass when you can’t get IN his ass.
So we came up with a plan: He would fly in for a few days, just to spend with me. I would meet him at our hotel room after work on Friday, and we’d spend the weekend together. Then, he would then tell his family he was flying in a few days AFTER that. By the time out mini-vacation is over, his family will think that he just landed – so he still gets to see his family while he’s in town, and we get some alone time without any interruptions. I was horned up most of the day just imagining the things we would get up to this weekend. All the things I would have him do…all the ways I would use him. It made getting up from my desk very difficult. I was already packed and ready to go.
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One fall, and I was spending the weekend at a local gay campground. If you’ve never been to a gay campground, I highly recommend it! Especially the ones that are clothing optional. Which, if you know me, you’ll know that this was one of those places. In addition to all your standard camping accommodations, they also had a pool and a few bars on the grounds. There’s also the forest trails and an afterhours “club” which are basically just covers for people to hook up.
I had just gotten out of the pool to refresh my drink and use the bathroom. As I got back in to rejoin my friends, someone callS out to me. Well, I kinda assume they mean me, since it was just a “hey.” Turning to look I see a cute, caramel-skinned cub smiling at me. I smile back and decide my friends could wait for me just a little longer. I sidle over to his side of the pool where he and one of his friends were hanging out.
We make introductions and I can tell that the cub, Jay, is a little tipsy. Not drunk by any means, but his smile has a hint of that goofiness you see in someone who’s feeling a little buzzed. He tells me he thinks I’m very cute, and I tell him he’s cute right back. He’s a little bigger than me, with tan skin all over. Short brown hair and a nice scruffy face, and that face is just adorable. His friend isn’t half bad either.
I can feel the alcohol doing its job as we flirt back and forth. There’s a little touching and some minor groping, but we keep it PG for now. As PG as you can while being naked and half erect in a pool, I guess. Eventually though, I needed to get back to my friends. Before I left, Jay, his friend, and I made plans to get together in just a little while. They tell me the location of their campsite, and we decide that I’ll meet them there later. Then, we will walk down to the trails together and…see what happens. I swim back over to my friends, cute bears in their own right, but with my mind still mostly occupied with Jay and the things I wanted to do to him.
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As a gay man, I can tell you that it is a fairly common occurrence to receive an invitation to a friend’s pool party. I mean hell, this is my second pool party story in a row. It is also fairly common that the pool party is going to be clothing optional. And it’s certainly not uncommon for people at these clothing optional pool parties to pair off and find a room to have some fun. Like the room with the sling set up in it. It’s good stuff.
On this particular Saturday, the party I was at was beginning to wind down. Starting in the early afternoon, and guests began slowly leaving the pool and hot tub as the evening drew to a close. The hosts were friends of mine, and I would be crashing there for the night – something I usually do if I know I’ll be drinking late into the evening. By 10 p.m., the only people left are me, the two hosts, and another friend of theirs. I specify “of theirs” because for whatever reason this individual did not seem to particularly like me.
I’ve written about one of the hosts before, Daddy M, who I tag teamed the sexy Bartender with. At this point in time, he was living with his then-partner Kev, and I would frequent their place to enjoy their pool, hot tub, and sex with the both of them. We had been chatting up a boy earlier, and made plans to have him come over once the party was done. The aforementioned sling was set up in the bedroom, and we were looking forward to getting him strapped in.
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When you were in school, did you ever start crushing on one of your teachers? Getting hard imagining your teacher disciplining you, contemplating the smell of your gym coach’s jockstrap, calling a certain professor “Daddy” in your head. Logistically, you know nothing will ever come of it, but you still fantasize about it. Mostly harmless.
Well, I did it. I fucked my teacher.
This story starts many years ago, when I was still in college. The degree program I was enrolled in was fairly new, and a lot kinks were being worked out as it went along. Along with that, we also had a pretty decent amount of young, or young-ish, professors. Since it was a tech-related program, everyone was pretty nerdy as well.
The subject my professor actually taught isn’t important, but you can be damn sure it was my favorite class. From that very first day, he made an impression on me. Scruffy facial hair, good sense of humor, and many shared interests - he was teaching in my major after all. Instant crush. Then I found out he was gay, and I nearly went all anime nosebleed everywhere. Found out in the middle of class too, so I really had to make sure I kept my shit together. After that, I probably spent the next two or so years hopelessly crushing on Teach. I think knowing he was gay gave me some sort of subconscious false hope that I actually had a shot. But I mean come on, I don’t think someone’s going to want to actually risk their job over some kid who can’t even legally drink yet.
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