OCTOBER 1992 | MARK:

    I did NOT imagine myself going trick-or-treating on my last day as a 29-year-old. I'd been looking forward to some quiet time at home alone while my wife took the kids out for the evening (the advantage to being born the day after Halloween). But this year my son got in a fight with his sisters over some stupid plastic jack-o'-lantern, so we had to separate them. My wife would take the girls out treat-or-treating, and I would accompany Logan.

    But first, I had to calm down Logan, who was dressed as Batman. His mom was going out trick-or-treating dressed as a witch, and he wanted me in costume as well. Luckily, it was easy pulling the wool over a five-year-old's eyes: I put on a suit and said I was going as Alfred. 

    We lived in a large building, full of wealthy people who loved making a big deal out of stuff like Halloween. Halfway through, Logan had more candy than he could eat in a month. I just followed and smiled at the neighbors, some of which I recognized, while others felt like complete strangers.

    And then, a familiar face answered the door in 30F. Instantly, I had an ominous feeling. Where had I seen him before?! I wasn't really active in the residents' association. Had to be somewhere else. And then I realized: I'd sucked his cock a few days ago! Down on my knees at a local cruising area, and he'd shot his load down my throat.

    "Logan, hi!" a little boy around my son's age suddenly appeared from behind the man who'd fed me his cum the other day.

    "You boys know each other?" the man asked Logan and the boy I assumed was his son. The answer was a clear yes, and Logan was already going inside the apartment.

    "Logan, no! We have to go," I yelled out after him.

    "Just five minutes, Dad!" he begged. "So we can trade candy."

    He and the boy ran to the living room, and I walked inside the apartment slowly. The host and I made intense eye contact as he shut the door behind me. Next, he put his hand on my back and guided me in.

    "Watch after your brother and his friend for a few minutes," he told a teenage girl who was sitting on the couch, watching TV.

    "Whatever," she responded without looking at us.

    The man led me through the master bedroom and into the bathroom as our sons' excited squeals echoed from the other room. There was definitely a feminine touch to the decor I was seeing. This guy must be married, just like me. That made me relax more, knowing that he'd likely play it cool if we happened to see one another in the elevator. And as he closed and locked the bathroom door, I was already getting excited about what the next few minutes held in store. I'd stumbled into the world of cruising and discreet sex a few months ago and it had changed everything for me, letting me scratch an itch that I had been reluctant to acknowledge for most of my life.

    This was the first time I'd ever been presented with an opportunity when I wasn't deliberately seeking one out. My heart was racing with excitement. What was it like for this guy, I wondered. He'd wordlessly invited me into his home with his own kids right in the next room. Had he done this before? Was it exciting for him in the same way? As he slid down his pants and his impressive erection popped out, it was clear that he was excited about something.

    Now that I saw his cock, I remembered him better. He was uncut and I'd only sucked a few other men with foreskins; he was definitely the biggest one. I got down on my knees and reached out to start stroking him. I'd barely begun when he let out a soft moan, and precum was already leaking from the tip of his cock and pooling around the skin there. I really needed to taste that, and my craving took over fully.

    As I licked his cock up and down and began sucking it, he moaned louder than before. I was so turned on that I reached down and undid my own pants as I kept my mouth working his shaft. I wanted to cum and I knew our time was limited. Recently I'd discovered that cumming with a dick in my mouth was an incredible feeling and I was eager to make it happen here.

    After a few minutes, he gently pushed my head off and motioned for me to stand up. I figured he wanted a turn sucking me, which was fine but I was acutely aware of how much time had already passed. To my surprise, he grabbed my shoulders and turned me to face toward the wall. I looked over my shoulder and saw him removing two saliva-covered fingers from his mouth as he smiled at me. I knew what he was thinking even before I felt those fingers move in between my ass cheeks, heading for my hole.

    "Hey!" I whispered quickly. "Sorry, I don't do that." He made no move to stop and I felt the wet fingers pressing around the edge of my opening, moving in small circles. It certainly felt nice, and I usually enjoyed some light touching there when the moment was right. But I'd never taken a cock up my ass before, and this was hardly the right time or place.

    "Oh, is that so?" the other man said in response to my statement. His smile got a little more devilish as he slipped one of his fingers into me. I drew in a sharp breath as it happened, and then closed my eyes. This was wrong in so many ways. I don't get fucked, I just don't. I'm not like that. Logan is here. This guy lives in my building, I might see him around.

    But another part of my brain overruled all those objections. The part that had been waiting for someone to take me further. I knew I could get him to stop if I really wanted to. I knew I could leave now, and probably should leave given the circumstance. But I didn't. Instead, I pushed out and relaxed my ass muscles to let him in more.

    I heard the man laugh to himself and moan at the same time, as he realized I wasn't going to make him stop. He slid his finger out, and then there was suddenly a much greater feeling of fullness and I knew he'd put both of his wet fingers inside me now. I could feel them slowly moving in and out. It was a little uncomfortable but not painful, and the discomfort was quickly overtaken by a growing sensation of pleasure. And a feeling that this was what I'd really been looking for all along. It felt good, and more than that, it felt right. I felt the man's arm wrap around my chest and next thing he was pressed up against my back. His rock hard cock was pushed up against one side of my ass and his fingers were going deep now. It was an incredible feeling to have part of him inside me like that.

    When he fully removed his fingers, I knew what came next. I closed my eyes and let out a breath, trying to relax even more. I felt both his hands on my hips now, and he was grinding his cock between my cheeks. The head was sliding up and down across my wet hole. And then a moment later, he was inside me. It felt different than his fingers had. Softer, but also more firm somehow. Bigger. And very quickly, deeper. I now had a man's cock inside me, where no one else had ever been before. My brain felt like it was full of fireworks. I was vaguely aware that my own cock was rock hard, the cooler air hitting it contrasting with the heat of the body behind me and within me.

    He was going faster now, pulling me back into him at the same time as he pushed into me. I knew I was making noise, moaning and whimpering, but I didn't care. I knew he would cum in my ass, and wanted that badly, even as I also wanted to make this last. But we both knew we were pretty much out of time. The kids were getting louder and rowdier in the other room, hyped up on all that sugar. "Logan," I thought to myself as the man's cock thrusted back and forth inside my ass. "I hope he's okay."

    Suddenly, he stopped thrusting and I could feel his cock throbbing deep inside me. The sensation was like nothing I'd ever felt before. I knew he was leaving his load in my virgin ass, this man I barely knew, the father of my son's little friend. And just like that, I knew he was going to be the first of many men I would do this with. I was now a guy who got fucked. And there was no going back.

    He pulled out and we hastily got ourselves together. My hard cock was drenched in precum. I hadn't cum, but maybe I'd save it for later tonight. Maybe I'd get to fuck my wife later, after the kids are asleep, while thinking back to this moment. I did my best to tuck my boner inside my pants so it's not noticeable. When we returned to the main area of the apartment, the kids had barely registered our absence. I went through the motions of making Logan gather up his candy and get ready to leave. I was barely aware of what I was saying, already replaying the events of the last few minutes over and over in my head. I didn't make eye contact with the man who'd just fucked me, even as we told our sons to say goodbye to one another. The door shut behind us and I was standing in the hallway once again. Logan was already running down to the next door and getting ready to knock. I followed after him, walking slowly, acutely aware of my stretched hole and the load of cum inside me. I could think of nothing else the entire evening while we continued trick-or-treating.

 

OCTOBER 2012 | OWEN:

    Logan's 25th birthday party was the biggest party I'd been to since my own prom. I finally got to meet his wife, who was the one organizing the whole thing in their lavish apartment. She personally thanked me for getting her husband in such good shape over the past year.

    "You'll never know how much of a difference it's made," she said to me with a twinkle in her eyes, probably thinking she was being coy. Next to her, her husband winked at me. I think we all knew what she was referring to.

    Even with all of Logan's friends and coworkers there, he still spent a lot of time talking to me. Which was just as good, because I didn't know many people, and this wasn't my usual crowd. I'd forgotten how many straight people there are in New York City!

    "Final confirmation: the party's definitely on next weekend! 🎃👻" I got a text while talking to Logan and his dad.

    "What's that?" Logan asked me.

    "It's a text from my roommate," I replied. "He's throwing a Halloween party at ours next weekend. Hey, would you guys like to come?"

    The words were barely out my mouth, when Logan shouted "Yes!" Mark, as usual, needed a bit more convincing. 

    "I don't know," he said. "Remember, I'll be 50 the day after Halloween. I'm now twice your age," he said to his son.

    "Which is all the more reason to live," Logan insisted. "We'll be there, even for a little bit. I'll take care of this one," he patted his dad's chest and winked at me.

—

    The weekend before Halloween, I was in my room, checking myself out in the mirror right before the guests started to arrive. I was dressed as a "sexy cowboy"; since this was a party organized by Kyle, I was sure everyone invited would be a sexy version of something. I wore leather chaps that I'd borrowed from a friend (I was too poor to own any of my own) and a white jockstrap. I'd owned this jock for years, and it was so well-used that it was almost see-through in the front. I was shirtless, with a cowboy hat on my head and a sheriff's badge drawn on one of my pecs with yellow body paint. 

    I went to the kitchen and rolled my eyes at Kyle's costume: a sexy priest. He wore a black jockstrap with a rosary attached to it. He was also shirtless, with only a clerical collar around his neck and a large, gaudy cross hanging from it. A knock on the door and the first guests were here.

    I was right: almost everyone was wearing a slutty costume. Most of the people were friends of Kyle, gay guys in their 20s who screamed "bottom" without even opening their mouths. But there were also quite a few girls, and even a couple of wandering straight guys who'd been dragged here by their girlfriends. About an hour later, Logan and Mark finally arrived. 

    "Hey," I said to Logan, dressed in an official Batman costume, and his dad, who was just wearing a suit. "Who are you supposed to be?"

    "I'm Alfred," he said, nonplused. 

    "Yeah, neither of those is gonna fly. We're doing sexy costumes in this house. Follow me," I took the father and son to my room and made them take some of their clothes off. 

    "You know, the first Halloween I ever remember, I was dressed as Batman," Logan said as I took his shirt off. "But I've never been a sexy Batman."

    He looked much sexier without the top portion of his costume, his well-defined pecs dominating the image. The pants were black and flattered his ass and package well enough already. With the mask and cape back on, he was obviously still Batman. I took some of the body paint I'd bought, and drew a decent black bat symbol on his chest. As I applied the paint with my fingers, I saw Logan's nipples grow several times larger. When I was done, I gave them a playful pinch, twisting them and making Logan laugh and fight me off.

    "You've worked hard on that chest, buddy," I told him as I turned him toward the mirror to check out my work. "This is the time to show it off." I could tell just from his face that he liked what he saw, and I smiled as I noticed him flexing his pecs in the mirror. I turned to Mark, who was also watching Logan closely.

    "Now it's your turn, old man," I said, hoping he didn't take offense at the term. With the glasses and fake gray in his hair, he was definitely well into "silver fox" territory tonight.

    "Okay," Mark said hesitantly, "but I'm not sure how you can make a three-piece suit sexy." I just smiled. This was even easier than Logan's.

    A few minutes later, the three of us emerged from my bedroom and I heard quite a few whistles and shouts from the guests. Mark's suit was now just two pieces, the jacket still in my room hanging in the closet, along with his shirt. His upper body was only clad in the vest, with the tie still around his neck and tucked neatly behind the vest's buttons. His arms looked amazing, and I felt a swell of pride knowing I'd been a part of making them that way. As Mark went to grab a beer, I heard a couple of Kyle's friends toss a "Hey, Daddy" his way.

    A few hours and more than a few drinks later, I was getting horny looking at all the naked skin around me. I'd had a few mouths on my cock already, but we'd always been interrupted by something before the guy was able to finish me off. With the women and straight guys here, it wasn't really the kind of party where I'd just whip it out and get blown in front of everyone... though I was almost drunk enough to not care about such things.

    The bathroom was almost always occupied by someone using the facilities or fucking in it. And as soon as a couple (or small group) finished some private time in one of the bedrooms, it seemed like there were others waiting to swoop in right after and shut the door. Kyle had disappeared into his room an hour ago and while quite a few guys had entered and left since then, he hadn't been one of them. I pictured the rosary swinging from my roommate's jock as all those guys came and went and used him as a cum dumpster. I wondered how many loads he'd collected inside his ass by now. 

    My eyes kept finding Mark in the crowd, and as the night went on we fell into a silent flirtation that I was really enjoying. Logan was near Mark much of the time so the father usually kept it more low-profile in those moments, but a few times I was surprised at how daring he got. Once when I was talking to both the father and son, Logan turned around to refill his glass and I felt Mark grab my ass. His hand rushed back to his side when his son faced us again.

    This game wasn't new to me. I'd been to plenty of parties where I'd share glances and occasional gropes with a hot guy while his boyfriend (or sometimes girlfriend) was blissfully unaware. But a father getting me worked up behind his son's back was certainly a new twist.

    At one point, I noticed Mark sitting by himself while Logan was busy talking to a straight couple. I'd spoken to the guy earlier and I knew he couldn't shut up about the new Porsche he'd just bought. This oughta keep Logan occupied for a while, I realized.

    Quickly, I went up to Mark and signaled for him to follow me. We went to the bathroom door and found it locked, unsurprisingly. But just then my bedroom door opened and I saw a couple of my friends emerge, one buttoning up the very small pair of shorts he had on and the other wiping his mouth with his hand.

    I grabbed Mark's arm and we dashed into my room and closed the door. He was on me almost before I could turn around, hands on my chest and pushing his lips against mine. That surprised me, because while we'd hooked up quite a few times before, going back to when I was a teenager, we'd never kissed. But I was happy to oblige and we stood there just making out for a minute or two.

    When I felt his hands starting to pull my hard cock out of my jockstrap, I backed up and sat down on the bed. As Mark got on his knees and moved to finish releasing my boner, I laid back on the bed and got ready to enjoy the good work I knew he'd be doing. He devoured my cock with an intense eagerness and I let loose with all kinds of moans and curses, letting him know he was giving me what I'd needed all night.

    There were some noises in the hallway, probably someone leaving the bathroom, and suddenly I felt Mark pull off my cock.

    "Did you lock the door?" he asked.

    "This door doesn't lock," I replied with my eyes still closed.

    "Then what the fuck are we doing?! What if someone walks in?" he said, sounding close to panicking. I wanted to explain that the door being closed meant that the room was occupied and that everyone knew that, but I was way too drunk to articulate any of that. So I reached over and grabbed one of the sheets crumpled at the foot of the bed. After a quick fling outward, it settled down around Mark, completely covering him from head to toe.

    "There," I said, maybe sounding a little impatient. "Now keep going."

    He obediently returned to what he had been doing, and I knew I'd be blowing my load down his throat within the next few minutes.

    Suddenly, the dark room was flooded with light as the door opened up and someone's head popped in.

    "Owen, there you are!" a voice said. I didn't need to wait for my eyes to adjust to the light to know that it was Logan. I suppressed a laugh.

    "Have you seen my dad?" Logan continued, opening the door more and stepping fully into the room. "I wanted to tell him that– Oh!" He stopped short, taking in the scene for a moment before a drunken smile made its way onto his face.

    "Sorry, I didn't mean to... uh... interrupt," he stood there looking at me, holding his Batman mask in one hand. I noticed that Mark hadn't stopped what he was doing, even though there was no way he didn't know that his son was now standing a couple feet away from him. "That's so fucking hot that he's not stopping!" I thought to myself. I just looked back at Logan silently, and brought one hand down to the back of Mark's head. I could feel his hair through the thin fabric of the sheet.

    "Right," Logan said, cracking a smile and starting over. "Uh... That couple with the Porsche invited me for a few spins around the block. If you see my dad, will you let him know?"

    "Sure," was all I could muster in response, getting closer to cumming with every passing second.

    "I need my clothes first, so I'm just gonna..." Logan said, gesturing at the closet on the other side of the room. He stepped over his father's legs, and grabbed the rest of his clothes from the closet. As he stepped over Mark again and moved toward the door, he looked down at the man deep throating my cock, unaware it was his own father. I saw Logan's hand move to his crotch and adjust something. He licked his lips and looked back up at me.

    "Sorry to interrupt your fun," he said with a sexy smile, but he didn't sound sorry at all.

    "No worries, buddy," I said. "I'm always happy to... AAAH!" And just like that, I started unloading in Mark's mouth right there and then. I pushed his head further down onto my cock to make sure he got all of it. My eyes couldn't stay focused consistently, but staring into Logan's eyes while his dad was swallowing my cum was an image I knew would stay with me for a long time.

    I was still giving Mark the last few spurts when Logan, still smiling, turned and stepped out of the bedroom. He looked back and winked at me before walking away, closing the door behind him.