NOVEMBER 2015 | RICKIE:
When I saw that there was a new message waiting on Snapchat, I felt my dick twitch in my shorts. He always sent me something right around 3 o'clock, as he was getting ready for school. It was the next morning for him where he lived, in Sydney, and for the last week I'd been treated to quick videos he'd send me as he changed into his school uniform every day. He'd pose for me and show off his cute ass and his hard cock, usually wearing only his button-up shirt and tie. I'd started to get excited as the time for his messages approached, then I'd worry that he might not send something today, and then chastise myself for worrying so much.
I only knew him as Ozzieboy99 ("Oz" for short) and it's not like he was my boyfriend or anything like that. But I got butterflies in my stomach whenever we'd chat and trade pics and vids, and I often found myself wondering if he had similar feelings about me. I was realistic of course, it's not like there was any chance we'd ever meet in person. And he only knew me as SF00Brick, though I'd told him to call me "Brody," a version of my name I was trying out as an alias in chats right now. This was just us having fun and feeling the thrill of showing off to each other.
Dad had given me a long talk when I got my first smartphone a few years ago, and I'd still never sent any nude pics to anyone over text or email. But when Snapchat came around, it was a complete game changer when it came to sexting. Since everything was temporary, lots of people my age were doing it now. Of course, that reasoning wouldn't hold any water if my father ever found out about this. But before chatting with Oz, I'd only ever sent dick or ass pics without showing my face. I trusted Oz though — we'd been chatting for more than a month. And it was only in the last week that we'd been doing this every day.
Today's video was him shirtless in some really cute red briefs. They had blue accents on the seams and they made both his bulge and ass look amazing.
"I stole these from my friend's older brother," the accompanying message said. "And they're not the first ones I've taken 😈 Even my friend doesn't even know about it."
"That's hot 🔥," I replied, and I meant it. There was something so dirty and hot about swiping someone's underwear to wear them yourself. "Do u ever put them back?" I texted.
"I haven't yet, but I'm thinking about cumming in a pair and putting them back that way. Should I do it? 💦"
"Yessssss," I wrote back. "But send me pics of that first!"
We'd never traded videos of each other jerking off or cumming yet, but I was feeling like that might happen soon. Seeing him cum in this guy's briefs would be hot as hell.
"I gotta go now but we'll talk tomorrow," Oz wrote. "Send me a pic in your favourite pair of undies then. K?"
"K," I replied, getting hard at the thought of doing some poses for him. He signed off to finish getting ready for school, and I decided now was a good time to record a few videos. I was extra horny after that and I had the apartment all to myself for a few hours, until Dad got home from work.
I walked over to my underwear drawer and opened it, but wasn't very happy with my options. Lately I was wearing Calvin Klein boxers, which were cute but I really wanted something more snug to show off in the same way Oz did for me. All my briefs were at least a year old, a little faded and worn-looking. I found myself wishing I had some nicer sexy ones like Oz. "But those aren't even his," I remembered, which gave me a titillating idea.
Walking across the hall to my dad's bedroom, I stepped up to his dresser and slid the top drawer open. My father did all the laundry and I rarely had reason to get anything from his cache of clothing, since he was bigger and taller than me, so I couldn't remember the last time I'd seen his underwear drawer. It was just as organized as I'd expected: everything neatly folded and arranged according to style and color. What surprised me was the number of things I'd never seen Dad wear before.
I saw my father walking around in his underwear almost daily, and I was aware he favored skimpier briefs much of the time. I'd occasionally see him in boxer briefs, or maybe a jockstrap if he was heading to the gym. But a full third of the drawer was jocks in a variety of colors and fabrics. There were also briefs I'd never seen before, ones where the pouch seemed sewn differently – to really accentuate the bulge, I quickly understood. There were even a few that had thong backs, which I had definitely never seen him wear around the apartment.
Feeling a rush, I decided to grab two different things, to see what looked the hottest. Suddenly I couldn't wait to take some pics in these, and I reached in to find whatever was the smallest and most likely to fit me the way I hoped. My fingers bumped something hard which was underneath some jocks at the back of the drawer. Reaching in, I grabbed something cylindrical and pulled it out. At first I thought it was a flashlight and I wondered why Dad would keep it in a clothing drawer. But I gasped out loud when I looked at the wider end. There was some flesh-colored rubbery material stretched across it, with a very realistic replica of an asshole right in the middle.
Oh my god! This wasn't a flashlight, it was a FLESH-light. My father's sex toy, something he used to jerk off. And it was right here in my hand. I'd seen these in videos online before (and often in the ads that filled half the screen on those sites). But I'd never actually held one before. I just stood and stared at it for a moment, then I slowly raised my other hand and rubbed my fingertips across the smooth puckered opening. It felt like... an asshole. Or at least it felt like mine, which was the only one I'd ever touched. I started to poke a finger into the tight hole, but then I suddenly felt a little guilty. This was my Dad's private stuff, and I was already crossing a few lines by sneaking some of his underwear to take sexy pics for a guy from the internet. Maybe I should leave well enough alone.
After carefully replacing the fleshlight, I grabbed a jock and a pair of the bulge-enhancing briefs and then slid the drawer closed again.
About an hour later, I stood naked in the same spot, opening the drawer again to replace what I'd taken. Taking the pics had been way more fun than I'd expected. As soon as I put the briefs on, all I could think was "this is my dad's underwear" and for some reason it got my teen dick rock hard. Which of course was great for the pictures, especially since the briefs put everything nicely on display. By the time I put on the jock, I was leaking precum at the tip of my cock. Doing the sexy poses in Dad's stuff felt so naughty on multiple levels, just like the fact that I was going to share the pics with a boy halfway around the world.
Before I placed the jock back in Dad's drawer, I checked inside the pouch to see if I'd stained it with my fluids. That's when I noticed there were a number of spots on the black fabric that had the telltale glisten of dried precum. It was way more than I could have left! I just smiled and realized I didn't have to worry about Dad noticing any of my stains; they would just mix in with his own.
While placing the undies back in the drawer, I couldn't help myself but reach for the sex toy I knew was there. I was even more turned on than I'd been an hour ago; my cock was now hard and throbbing under the open drawer. The same thrill I'd felt when putting on Dad's briefs came back to me, and in that moment I knew my dick was shortly going to be sliding inside that fleshlight no matter what. It didn't matter that it was a totally inappropriate thing to do. Maybe, even, that's what made it such a huge turn-on.
I walked over to my father's bed and climbed on in a kneeling position. Placing the tip of my cock right at the opening of the rubber toy, I took a deep breath and started to push in. I wasn't sure what to expect, if it would feel so obviously fake, or cold, or abrasive. The pliant material was surprisingly soft and smooth, and as it stretched around my cock the tightness of it gripping my shaft was almost uncomfortable, but ultimately just right. There was pressure without it truly squeezing me. I'd used my precum to slick up my dick a little right before, and it also felt like the edges of the hole were coated with something. I realized my Dad probably used lube when he fucked this toy, and I briefly thought to rummage around to find it, or to go to my room and get my own. But I also knew that, turned on as I already was, I was going to cum pretty soon.
After pushing in as deep as I could go, I pulled the toy almost all the way off my cock again, moaning at the sensations I felt as the inside of the tight hole pushed up against the flare of my cockhead. I repeated the long stroke several times, finding the speed that maximized all the most pleasurable sensations. Before much longer, that feeling was building inside me and I knew it wouldn't be long. And suddenly, I had a dilemma on my hands. (Well, more like in my hands.) I desperately wanted to just keep going and blow my load inside this toy, like I would inside a real guy's ass. But is that what I was supposed to do? Is that what Dad did? Now I was picturing my father on this very bed fucking this same toy, and then filling it up with a thick load of his cum. And suddenly I was doing that too.
As I shot my load into the plastic tube, I fell onto the bed, knees still bent, and the motion pushed my pelvis higher and seemed to force the fleshlight further down onto me. It felt incredible sensing that pressure at the base of my cock as I finished cumming, and I stayed in that position for a minute or two just to catch my breath. Once I had recovered, I stood up and slowly pulled my dick out, mindful of the head being extra sensitive as it usually was after I shot a load.
I stood in Dad's room staring down into the hole of the toy, which had quickly returned to its former state of tightness. Unsure for a moment what I should do, I thankfully noticed that the end screwed off and I opened it up, peering inside curiously. I saw my cum pooled at the bottom, and then gradually noticed the dry flaky residue on the inner surface. There was more of it the further in I looked and the bottom (what I could see of it) was pretty crusty.
"Fuck!" I thought. That's Dad's cum. He doesn't clean this out, or at least not every time he uses it. I pondered that for a second. Was that gross? Maybe. But then again, this was his toy, presumably not used by anyone else. So did it matter? In any case, I was more fascinated by it than anything else. And I also realized that it meant I didn't necessarily need to clean it out. In fact, if I did, and Dad noticed it being mysteriously clean, he might deduce that I was responsible. So the best option was to leave my load in there to dry out alongside my father's cum. Smiling and feeling the naughtiest I had in a long time, I placed the toy back in the drawer carefully, just as I had with the underwear I'd taken, making sure things looked just as they had before.
NOVEMBER 2021 | DYLAN:
Going into the sex shop hadn't been part of our afternoon plans. My boyfriends and I had seen a classic movie at the Castro Theatre and we were walking around trying to decide where to go get a late lunch. This area, the most well-known gayborhood in the city (and perhaps the world), was bustling on what was a surprisingly warm fall day. There were plenty of tight jeans with packed bulges, sleeveless shirts showing off muscular arms, and eyes coyly darting around, checking out others who were doing the exact same thing.
As we walked by the storefront, Brody had commented that he needed some more lube and they sold his favorite brand in this shop. Being the other beneficiary of that purchase, I gladly agreed to the brief shopping trip, and Thorne had no objection to it either. Before long, we were all browsing the wide variety of things on display in the sex shop. We'd consumed some edibles before the movie and were feeling light-headed and a little silly. Thorne pointed to a huge dildo on the wall and asked if I thought I could take it, cracking a smile. Instead of answering, I teased back that we probably shouldn't go down that road, since I might give it a try and decide he was replaceable. We all laughed. Then Brody picked up a fleshlight that was on a display shelf nearby, unboxed so prospective buyers could see the details of what they might be shoving their cocks into.
"So is this what would replace me, then?" he asked, teasing the realistic-looking asshole with his finger while he looked at me.
"It might feel similar," I said, sounding like I was giving it serious thought, "but I don't think it's capable of begging me to breed it over and over, the way you did this morning." I noticed both my boyfriends flash me a knowing grin, and I had to smile as I thought back on the morning's events. After I'd finished granting Brody's desperate requests by filling him with my cum, we'd noticed that the bedroom door was wide open and we were visible (and certainly audible) to the rest of the apartment. Thorne had been sitting in the living room having coffee and reading something on his tablet, and there was no doubt he'd heard everything clearly.
"You know, I used to have one of those," Thorne commented in the shop, nodding at the toy that his son was still holding. "I had that thing for years. It came in handy now and then when I needed something more than just my hand." I smiled at Thorne's recollection, but Brody burst out laughing loudly for a couple of moments, which confused his father and me.
"What is it?" I asked my younger boyfriend.
"Well, um..." he began, "I was just remembering something." Brody looked one more time at us, trying to decide if he wanted to continue. Laughing and then pausing again, he finally kept going. "When I was like 15, I found your fleshlight, Dad. When I needed to... borrow some socks. I'd never seen one of these before that, and I... um..."
I was treated to a sight I rarely saw when Brody visibly blushed, his ears turning a dark pink as his smile got even bigger. Thorne and I both stood slack-jawed for a moment, genuinely surprised.
"You're kidding me," Thorne said in a deadpan tone. "You fucked my fleshlight? Jesus Christ, boy, I feel like I did whole laundry loads of your crusty socks back then, and still you couldn't keep your dick out of my stuff?" My older boyfriend smiled again, shaking his head and looking amused and resigned. "How many times? Do I even want to know?"
"Just once!" Brody said quickly, and immediately received questioning looks from both of us. "Okay," he admitted, looking sheepish and rolling his eyes, "maybe a few times..." As he placed the toy back on the shelf and turned away, I heard him mutter the words "... a month" quietly under his breath. I'm not sure if Thorne heard that or not, but we continued to walk toward the back of the shop, which was more of a clothing area.
I stopped to reach out and feel a leather harness with my fingers, and Thorne was suddenly right behind me, bumping his crotch into my ass. I wasn't totally surprised to feel his jeans-covered hard cock pushing against me as one of his hands went to my waist. I'd gotten hard imagining a teen Brody secretly using his father's sex toy, and apparently so had his father. And that made my cock get even harder.
"Well gosh, you guys, I don't feel very special now," I said in an exaggerated sad voice. "I always thought that I was the only sex toy you two had shared." They both cracked up at my joke.
"Maybe not the first," Brody said, cozying up to me and facing me, "but definitely the best." He leaned in for a kiss which ended up being a nice long one, and I felt his hardon pressing into me as well.
With Brody in front of me and Thorne behind me, I found myself in a spot that I always loved. There was nothing quite like being pressed in between them, and the three of us were feeling horny and adventurous. Something unspoken seemed to pass between us, and then Thorne made a show of grabbing a few things off the racks.
"Well let's go try this stuff on, boys," he said, affecting a tone that almost sounded resigned. As if we were somehow reluctant to all be heading into the fitting room, which was really just an alcove in the back of the store that had a curtain pulled across. The sales clerk was at the front of the store ringing someone out, and he seemed to be the only employee working. A few other guys were browsing in the small shop but no one was especially near to us or paying us any attention, so we quietly slipped behind the curtain.
The space wasn't that cramped, which I appreciated. As nice as it was being squeezed between my guys, it was good to have options in terms of position and angle. Deciding that I was going to take charge, I helped both Thorne and Brody undo their pants and then got us all facing the same direction, with me in the middle. But we all were also facing a large mirror, so each of us was able to look the other in the eye whenever we wanted. Seeing the eagerness in my boyfriends' faces as we got going, and watching the two of them trade looks with one another — that alone got me worked up enough to be leaking a ton of precum by the time I was sliding my cock into Brody's ass.
As soon as I got most of the way into his son, Thorne's cock pushed inside of me hard. It wasn't unusual for him to get a little rough but typically we worked up to that over the course of at least a few minutes. Today though, he was going full steam ahead. Maybe it was because he hadn't gotten to fuck me this morning, instead listening in on me fucking his only son.
Realizing quickly that this was going to be an intense fuck session, I leaned forward a bit and used my arms to brace myself against the mirrored wall. This pushed Brody forward a little as well and he was pressed up against the mirror. Not tightly, but close enough where he needed to turn his head sideways to make sure his face didn't get pushed hard into the glass unexpectedly. I got in close, licking the back ridge of his ear and kissing his neck, all while Thorne was doing similar things to me.
I stopped trying to set the pace of the fucking after a while, giving in to the rhythm Thorne had established and letting that dictate when I pushed into Brody. Rather than grinding back and forth between them, I was just passing the intensity of Thorne's fucks along to his son like a ripple effect. This made it feel like I was pounding Brody harder than I ever had before, harder than I even could on my own, all thanks to his own father. For my part, I was feeling less like a participant and more like a conduit, the middle car of the train that was used to get from one end to the other. I'd joked about being their shared sex toy earlier but now that's what it seemed like I was. This combination of pleasures and sensations was already overwhelming, and the added layers of feeling like their plaything – and doing this in the fitting room of a store – were ramping me up quickly. I knew I'd be flooding Brody's hole with my seed soon, for the second time today.
Thorne was basically slamming his hips into me now, hitting a spot deep inside me each time he thrusted forward. He was breathing heavy and I was gasping a little, with Brody whimpering softly as his cheek pressed into the smooth glass. Overall we weren't making that much noise, but I was feeling like things would get even more intense soon.
Brody loved to have his hair pulled while being fucked from behind, and I started to move one of my arms to grab a handful of the dark curls on his head. But because I wasn't using both my arms to brace myself against the pounding I was receiving, my shoulder pressed forward into Brody's back and we were about to be pushed into a painful position. So I moved my palm back onto the glass to support myself. I'd only managed to grab Brody's hair for half a second, but it was enough for Thorne to see in the mirror. The older man surprised my by reaching one arm forward and grabbing his son's hair, pulling his neck backward toward us even as the relentless fucking continued.
Brody gasped and then moaned, and in the mirror I could see that his eyes were closed. I wondered if he even knew that it wasn't me pulling his head back. He was lost in his own world, dealing with the double-strength pounding as best he could. It went on like that for a few minutes, long enough that a part of my brain started to wonder if there was a line forming for the fitting room. And then, that idea seemed to get me even more turned on as well.
"Fuck me hard, Daddy! Fuck me hard!" Brody cried out, in a voice that could definitely be heard by people in the shop. While he did sometimes call me "Daddy" while I fucked him, at the moment with Thorne setting the pace and strength of the pounding, it was difficult to imagine that Brody's comment was directed solely at me. Brody was begging his own father to fuck harder, the father who was also pulling his hair back, like I loved to do. Those thoughts combined with Brody's words are what sent me over the edge, and I began blowing what felt like an even bigger load than I had earlier in the day.
I could feel Thorne's cock throb inside me and I heard his breathing change, and I knew he was going to start unloading any moment. I desperately wanted Brody to cum too and after so long together I had a sense of when he was close. I felt Brody's ass clenching soon after, though it might have also been a response to hearing his dad cumming. Although Thorne tried keeping the noise down while he bred my hole, it was obvious to both me and his son that our daddy was cumming. Finally, Brody shot his own load all over the mirror in front of him, at the same time as his parent.
We kept fucking for a few more minutes and then once the pace was back to normal, we slowly disengaged. As Brody backed away from the mirror, I could see his load dripping down the glass. We all took deep breaths and made eye contact again in the mirror. This time we all had the same satisfied smiles on our faces. We quickly got our clothing back in order and then emerged from the fitting room. In another unspoken decision, Thorne and I quickly headed for the front door, nodding politely at the cashier as we passed. When we got outside, we had to wait a minute for Brody, who emerged with a bag. It contained the lube we'd originally come in for, I realized. But it also looked like it had something heavier in it, and when I took it from Brody I laughed again, amused to see a brand new fleshlight in there as well.