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Shaun - $20 is $20, Sex is Sex: Part II
🕑 Added 2025-03-29 03:09:02 +0000 UTCPart II
The following day, I woke up feeling hungover, sick to my stomach as the flashes of last night washed over me. I had sore in muscles I didn’t know I existed and as I wobbled to the bathroom to throw up, I now understood the joke about “you’ll be walking funny” to describe what it feels like to get fucked. I felt particularly gross when taking my morning shit and realized the wetness was probably Trevor’s cum from when the condom broke and he shot his first load inside me. I held my head in my palms, rubbing my face. Ugh…I can’t believe I let another guy fuck me, and he accidentally shot his load in me, I cringed.
I took a hot shower, stretching my muscles and trying to scrub off my shame. Then, I dressed in very baggy clothes, hoping not to be seen when entering the world. Of course, I didn’t have a proper shipping box to pack last night's goods in, so I put the two ziplock bags in my backpack and headed to the post office.
It felt like everyone I made eye contact with was looking at me, knowing, judging me for what I did last night. I was even more embarrassed as the more masculine men looked at me knowing I was the bitch last night, I wasn’t even the guy doing the fucking.
At the post office I grabbed one of those “if it fits, it ships” boxes, and tried to discretely pull the two ziplock bags from my backpack and put them in the box, dropping the second bag on the floor because they both had too much air in them and wouldn’t fit in the box without being deflated. I rolled my eyes, unzipped the bag still in my hand, the one with my cum-coated white briefs, quickly pressed the air out, which smelled like my cum and it was still wet and cold, very gross. Shoving it in the box, I bent over to pick up the second bag, which I realized you could clearly see the CK logo on the white briefs and the wet, used condom sticking to the plastic material of the ziplock. I scooped it up, unzipped it, and let the air out. It had a different scent, a scent that was clearly Trevor wafting off the underwear, the other distinct smell was his cum mixed with latex and had I eaten breakfast I would’ve hurled at the thought.
Forty-eight hours later, my cash app chimed. Never in my life had I seen that much money all at once. I tried to calculate how many people must have watched that Zoom for it to add up, but it didn’t work out easily. I didn’t think to get Trevor’s number, so I couldn’t even text him to make sure I was paid fairly, or at least what he was paid. Then again, I don’t know what deal he and Carl had for payment, so I guess it could be offensive if one of us were paid considerably more than the other. However, I had no complaints since it was much more than I asked for.
I used the money to catch up on my parents' bills and even get them ahead on a mortgage payment. Then, I put the rest in my savings account for the next emergency or maybe a vacation.
The requests for underwear with my load on them kept coming in, and I kept fulfilling them, adding a little more to my piggy bank with each load. I was making money hand over fist while still working as a waiter. I started feeling more comfortable with everything that happened with each day I put between me and that night.
I hadn’t heard from Carl in any way other than the payment I received. Not even an “atta boy,” for getting my cherry popped. I get it though, once you’ve seen all you wanted to see…the fantasy can die off, and it’s sure not worth the kind of money he was throwing at me if it’s the same stuff he can get from any free porn streaming site or OnlyFans.
Almost a month after the night with Trevor, I had settled back into my regular routine. I had a few underwear orders to fill and my tank was running on empty. The same porn videos I usually watch to bust a quick nut had become dull and I found myself looking at threesomes that were male-female-male for a little while, then quickly went to male-male-female and that anal play really helped me cum for a few days.
Two months had passed, and fall was right around the corner. I was doing a deep cleaning of my apartment when I found the clonded dildo of Carl’s dick in the back of a drawer. I forgot I even had it, but just holding it in my hand, giving it a squeeze, the feel of it was sending blood to my dick. It was barely noon, and I had a night shift tonight, so I figured I could rub one out, fulfill an order, then do it again when I get home tonight, and that would catch me up on my fulfillments for this week.
I set the dildo on the nightstand, pulled out a pair of white Hanes briefs from the six-pack, laid the undies out on the bed, sat on my knees, and jerked off as quickly as possible, unloading a decent-sized load for the lucky guy to get this delivery. I dressed, put the soiled briefs into a ziplock bag, and tossed them in a box to be shipped on my way to work.
Work sucked, more so than usual. I was looking forward to a little stress relief when I got home. I pulled out my laptop, putting on some male-male-female porn, set a fresh pair of FTL white briefs on the bed and got into my usual position, sitting on my knees and stroking myself.
The porn was helping. I tried to focus on the guy in the middle, knowing what it feels like to fuck a woman and being fucked by a man, not at the same time, but both feeling really good.
I was getting close to blowing my load when I heard the woman say, “Oh baby, it’s been so long,” to the guy fucking her and it dawned on me I hadn’t had sex with anyone since Trevor, and it had been more than six months since I hooked up with a woman. This side hustle was keeping my sex drive in check.
I kept getting myself close to cumming, but then didn’t shoot. I groped my balls, rubbed my abs and pecs, then back to my balls as I stroked, but would only get on the edge.
When the woman in the video pulled off the guys dick and watched him get fucked by the other guy, I noticed how much he leaned into it and started to really enjoy getting fucked by that guy. I stroked a little faster, remembering only the good parts of having Trevor fuck me. I noticed Carl’s dildo on my nightstand and didn’t give it a second thought. I grabbed it and quickly lubed it up, then my ass and slowly pushed it in. I shifted my feet so I could hold the dildo in place and gently rock my hips up and down on it as I stroked my dick. It quickly brought me back to the edge, and this time I held off on purpose, just enjoying masturbating for the first time in weeks.
I could only edge myself for so long and then got to a point of no return. I quickly laid the underwear on my abs as my balls tightened, my ass clamped down on the dildo, my thighs quaked, I aimed my dick at the underwear, lifting the fabric in a halfpipe to catch the first few volleys of cum, and then let the rest of my ogasmic release pool out over my fist and into the fabric as my body shuddered in orgasmic bliss. The dildo pressing on my prostate made the orgasm so much bigger, by the time I stopped spasming leaking cum my balls were drained to a point I hadn’t felt in a long time.
I took a deep breath and huffed a sigh of actual relief, remembering how relaxing a real orgasm is, not just a forced jerk. Fuck, am I ruining sex for myself? Should I stop this side business before a real orgasm is unachievable?
I tossed the underwear in a bag and put it in a shipping box. Washed TGI Fridays and the lube off in the shower and called it a night.
Over the next couple of weeks, I used the dildo to get myself off and fulfill more orders. It started getting old, though. I decided to set a goal for myself, rounding up to the next nearest thousand dollars, and then I would shut down my side hustle, at least for a while. When I reached that goal, I had a small stockpile of underwear still in the package and took a few more orders, putting it out there that I wouldn’t be doing this once supplies were gone, and these last six were going to the highest offers. The interaction I got from this was incredible. Each pair goes for a few hundred dollars each, of course, with additional promises of a video included, which meant I had to do the jerking off part while wearing the underwear. It was harder to perform since I had gotten so used to having the dildo to help me get off, but I managed to complete those orders and went dark on the Insta handle I used to build it up.
By fall, I had a new coworker who handled the bartending at Friday’s. She is a fiery Puerto Rican woman two years older than me. We hit it off pretty well and started dating. I thought it was going well, but she took a job putting her degree to work in the fall of 2023, and by January 2024, she broke up with me. She said I wasn’t “ambitious enough for her,” and “definitely not serious enough for her to keep investing in our relationship” since I had been working at Friday’s for more than four years now.
That hurt, but I took it on the chin.
Then came the announcements that TGI Friday’s would do massive layoffs and close several US locations, including mine. This hit me hard. I hadn’t given much thought to an exit strategy from this job and didn’t think I would need to. I enjoyed the people I worked with, and the work wasn’t too hard. Sure, customers were awful people, but it paid the bills.
Nobody was hiring, so I took advantage of my free time by hitting the gym and jogging again. My posts of my exercise routines and thirst-trap updates received a lot of attention from friends and family, even some strangers, which was flattering.
My unemployment benefits expired by the summer, and I started hemorrhaging my savings. It was beginning to look bleak. I cringed, but I reactivated my UndiesGuy Instagram handle as a stop-gap until I could find more work or at least make moves into a career I wanted to be a part of.
I put on a pair of red CK hip briefs and went for my usual jog. When I got to a part of the park that is usually packed on weekends and noticed it was empty, I decided this was as good a spot as any and quickly stripped down to take some pics. Just as quickly, I dressed and continued my jog.
When I was home, showered, and scrolling through the pics, I cropped one that was particularly glistening with sweat. My gains were popping, and my package was really popping. I posted it with the caption, “Should I wash these undies or…”
I settled in and watched some Netflix.
Before bed, I checked to see if UndiesGuy had any updates. To my surprise, I had a bunch of likes and some DMs already. One particular caught my attention:
“Not sure if you remember me, but we did a live stream a few years ago for a man named Carl and made a boatload of money. I see you’re back online and was wondering if you’d be up to colab again? - Trevor”
Of course, I remember Trevor.
I started and deleted a few responses. Eventually, with my heart pounding, I settled on:
“Hey, Trevor, Of course I remember you! That was my first and only experience having sex with another man lol. What kind of colab did you have in mind?”
Trevor: One of the guys who watched our stream found me here about six months later, and he started offering me way more money than Carl to do things for him. Not as much as we made that night, but for solo stuff and a couple of one-on-ones with other content creators, the money is pretty good. He had asked if you and I would be into a repeat, but I told him I didn’t have your contact info, and he dropped it. By the time I found you on here, it seemed like you had been offline for a while. If you’re interested, though, I could reach out to him and see what he’s willing to spend money on, check back with you and see if you’re down?
Fuck. That was good money, really good money, and with things going the way they’re going, I could really use the money. I don’t really want to get too deep into this, though; I hadn’t even wanted to restart the underwear stuff.
Me: Well, I can’t say for sure, but let me know and I’ll consider it. I’m not trying to make this a lifestyle, just some extra cash to supplement my income at the moment.
Trevor: I get it, times are tough. This has become my sole income for a while now, so I’m definitely trying to collect a big paycheck, and if you’re down, I’m down. I’ll let you know in a day or two what’s up.
Almost a week went by before I heard from him again.
Trevor: My guy would love to set up a collab but he said he’s seen us fuck already and has that video. What he wants is to spice it up a bit. There’s an Instagay couple he thinks he can set us up with, that he knows can be big money for a select audience if we’re up for it, but he said you have to be 100% before he starts making deals and talking money.
It made my stomach turn to know this guy has a recorded copy of our last stream together. Carl insisted that was for his private collection. I don’t even have a copy of that video.
Me: Who is the couple? Do you think this will be more or less money than the last video?
A few hours later, he responded.
Trevor: He didn’t say who the couple is. I guess they make a boatload of money as influencers who claim to be monogamous, so he doesn’t want to hurt their brand by shopping around their names. I get that. But, because it will be a risk for them, it probably means more money for everyone involved. If you want, I can tell him that it needs to be at least matching what we were paid last time, but with the same runoff.
Me: Ok, if it’s the same or better, I’ll do it. I can definitely use that extra cash.
Trevor: Me too lol. I’ll let you know.
Two days later, he hit me up again.
Trevor: Ok, if you’re in, these guys are in. From what I understand, my guy told them I’m a top and you’re a bottom, and they have the same dynamic. For us to get paid, we start the two of us, then we try them out, everyone cums and we all get paid. No sending out care packages after.
I really didn’t want to have to get fucked by two guys, but if the money was worth it, I could be a bottom for an hour.
Me: Ok. I guess…count me in, let me know the details.
A few days later, Trevor let me know the details. These guys live in LA, so we would need to fly to meet them, and we would do it at their new house.
I had little money left, but I bought myself a ticket. Trevor told me he would spring for a hotel room for us, but I’d have to eat the cost of my flight.
When I arrived in LA, he met me at the airport, drove us to the Beverly Wilshire, and let me relax as he filled me in.
“So, here’s the thing, I didn’t know this until I got in yesterday, but this isn’t going to be live-streamed, or recorded at all.” He said.
“Ok, great, but…”
“So, there’s going to be an audience. Apparently, these Instagays are really strict about their image and reputation, so they set up their fully finished basement lounge space with all kinds of cameras, monitors, and seating areas. I guess it’s big enough for a large group, and we will basically perform in front of a live audience. Like Broadway, but with more nudity.” Trevor relaxed after dropping this information bomb.
“Oh,” the thoughts raced through my head. “I guess…whatever. I’ve never had anyone watch, at least not in person, it could be kinda hot.” I shrugged, my head spinning at the idea of it and how that would even work.
“Phew, I’m glad you’re okay with it. At first, I was apprehensive, but as I realized it meant nothing that happens tonight lives on beyond tonight, I felt a bit of relief.” He flipped open his iPad and swiped through some stuff. Turning the tablet to me, he played a YouTube video, “These are the guys; you might know them if you follow their kind of stuff.”
I chuckled, “I don’t think I follow any gay influencers, at least none that are known for being gay,” then watched the video. The taller guy is fit, handsome, with big, pretty eyes, and I want to say he has a British accent. The shorter guy is good-looking and a bit effeminate, but they seem like nice guys. “I can’t say I’ve ever heard of them.”
“No worries, they don’t know us either,” he chuckled. “So…you’re still in?”
I shrugged, “I’ve come this far.”
He took me to the spa where we got well-groomed, then taught me how to “clean out properly,” we talked over some of the boxes that needed to get checked for us all to get paid. One important thing was that we were to ignore anyone outside the four of us, no matter what, no breaking of the fourth wall. I didn’t understand why he stressed that so much, but I figured that would be easy enough. The other big one was to make sure we all cum, he seemed concerned that I would get stage freight and wouldn’t be able to cum. I laughed that off and let him know I’d been saving up for a couple of days to make sure I could cum.
“Umm, this is probably a dumb question, but we’re going to use condoms, right?”
He shrugged, “I can definitely wear a condom, but you should make sure that’s not a deal breaker for them when we get there.”
When we arrived, there was an awkward meeting between the four of us. They had us arrive well before the guests arrived so they could give us a tour and we could all get comfortable with each other. They offered us wine, specifically white wine, because they both had just done teeth whitening and didn’t want the red to stain. We discussed what the shorter guy called “the show flow.” He went into detail about who would do what, and when, making sure everyone was on board with his plan, and we killed a bottle and a half of wine.
When the guy who set the entire thing up arrived, Trevor introduced us all. The influencers asked a lot of good questions that I would never have thought to ask. Clearly, they were good at business. I just followed along quietly.
The guy agreed he’d man the door and escort everyone into place so we could stay upstairs in the bedroom until it was time to start. Let the guests get liquored up and get comfortable. No one asked what “get comfortable” meant, so I didn’t ask either. I wasn’t sure I even wanted to know. It felt way bigger than the intimate session Trevor and I had last time, and I started feeling a little anxious; thankfully, that was around the time the wine kicked in.
Watching them all swap stories made me feel a little more comfortable. Knowing that I was going to have to let the taller guy fuck me and between the three of us they had way more experience with man-on-man sex than I had set me more at ease because I could just go with the “show flow.”
“What about you, Shaun? You’ve been awfully quiet,” the tall guy said, smiling at me.
“Oh, umm, actually, this will only be the second time I’ve had sex with another guy,” I blushed.
“What, no way?” His grin grew as he shared glances with his husband.
The shorter guy squinted at me and sipped his wine. “You’re telling me you’re in your twenties,” his empty hand gestured up and down, pointing at me, "Look as hot as you do, and you’ve only been with one guy before tonight?”
I met Trevor's eyes, and we both cracked up. “Well, actually, Trevor is the only guy I’ve been with.”
“He’s straight by the way,” Trevor added.
“No shit, mate, what are you even doing here?” The taller one asked, and his smile looked a little more worried.
I shrugged, sipping my wine, “Money?”
They both laughed, the shorter adding, “Yeah, aren’t we all, babe? But we only get paid if we see this through. Are you,” he gave me a judgmental look, “able to perform, being straight and all?”
Trevor chimed in, “Oh don’t worry, he’s very able to and one of the best fucks I’ve had.” He gave the taller guy a wink.
The influencers gave each other a skeptical look but stopped their line of questioning.
“Umm, speaking of which, I already talked with Trevor about it, and I was wondering, what exactly the condom situation is?” I sounded like an idiot for phrasing it like that.
They looked at each other and snickered. The shorter one cocked his head to the side, gesturing between the two of them, “Well, we’re married so…we don’t use condoms. God, I can’t even remember the last time we used one,” he chuckled.
I felt myself turning red. Addressing the taller guy specifically, “Would you be cool with wearing a condom?”
He looked at his husband; they shared some sort of secret conversation with their eyes. “Umm, well, I’m on PrEP and have a recent set of test results if that’s a concern.”
“You guys are both on PrEP, right?” The shorter one asked.
“I am,” Trevor chimed in.
“I…am not entirely sure what it is. I mean, I’ve heard of it, but…” I shook my head, “I’m not using it.”
“Oh, honey, you should really be on PrEP,” the shorter guy said with a tone I didn’t particularly enjoy.
They looked at each other, having a silent conversation, then the taller one glanced over at me, “I guess I can try it, with a condom. It’s been a while, but…”
“It’ll be fine, he’ll be a good boy,” the shorter guy cut him off. “I assume you brought condoms, right?”
I chuckled, “Yeah, I didn’t know your sizes, so I got some regular and some Magnums.” I pulled them out of my bag, which also had a change of clothes.
The taller guy grabbed the regular-sized condoms, and I felt a knot in my stomach unwind. “Spermicidal lubricant,” he chuckled, “you really don’t want to get pregnant, huh?” His husband chuckled with him.
I shrugged, “Oh, you know what, I’m so used to grabbing those for…I didn’t really think about it.”
We stayed in their bedroom as people started to arrive. At some point, the guy came upstairs and let us know everyone had arrived and that we were good to start at any point.
My heart raced as the shorter guy smiled and thanked him, letting him know we’d be down in a few minutes, tossing the box of condoms at him, telling him to put them on the end table with the lube. “Cheers, guys. Let's have some fun,” he said, and we all clinked glasses and finished the wine. Then he stripped off his shirt, and his husband followed suit. Trevor looked at me with a smile and started stripping too. I hadn’t seen the memo that we were stripping first, but I joined.
The taller guy wore a pair of black trunks with a thin white waistband that accented how fit he is. The shorter guy was skinny but definitely didn’t work out like his husband, but he was still looking good in a pair of black and gold Gucci briefs. Trevor was a little more buff than when I saw him naked, wearing the white CK hip briefs, and I wore a pair of black CK trunks. Everyone silently checked each other out briefly before the taller guy said, “Let’s go, fellas,” and led the underwear parade downstairs.
Thankfully, we had the tour earlier because the downstairs space was now darker, with mood lighting, specifically in the area with the lounges where we would perform. They had been arranged to form a slanted ‘L’ shape, almost a ‘V’, one jutting further into the audience than the other. I noticed quickly all the shadows of men standing around with drinks, ranging in age from early 20s to maybe 65. The room was warmer and had a unique scent I couldn’t quite pin down.
I followed closely behind Trevor as he trailed behind the other two. They wasted no time, the shorter guy taking charge, wrapping his arms around his husband's neck, pulling him in for a kiss. They seemed to have a routine and were on the chase closer to the wall, leaving the opposite one that seemed to point towards the center of the room for Trevor and me to use. Trevor quickly noticed I had no idea what to do and was getting a bit of stage fright. His left hand trailed down my right bicep until his fingers intertwined with mine and he pulled me closer to him so my package was lined up with his already hard barely hidden dick. I took a deep breath, looking up into his eyes as he smiled and mouthed “re-lax.” He leaned in and kissed me.
I closed my eyes and tried not to focus on the fact that I was kissing a man or that there were easily twenty men watching us right now. I just kept my eyes shut and felt Trevor's bare torso. The peaks and valleys of his muscles, the tufts of hair forming a trail down the center of his torso, the heat that came off his body. His pecs had squared off a bit. I was kind of jealous because the work I’d been putting in showed excellent results, but he looked chisled out of marble. Granted, his pale skin tone helped with that look, whereas my mocha skin color made it easier for the shadows to appear and made my muscles pop even where they were barely defined.
He pushed me gently down to sit on the chaise, running his fingers through my short hair, massaging my head with his right hand and my package with his left hand. I tried to focus on him, his face helping me to know what to do next as he smiled down at me. His left hand ran up his chest and slowly down his abs, slipping in the waistband of his briefs to grip his dick. He quickly pulled the waistband down below his balls, exposing his massive tool, which, gun to my head, I’d swear it was bigger than the last time I saw it.
I looked into his eyes and he grinned, glancing at the other two guys. I followed his gaze and saw the taller guy pulling his husbands head up and down his shaft as the shorter guy did his best to suck the dick without choking. My eyes went wide and quickly darted back to Trevor’s. He couldn’t possibly, he didn’t expect me to suck his dick…did he? I thought it was just going to be a repeat of last time where I just lay there and got fucked.
He smiled at me, rolling us so he was on his back and I was half on him. He placed his hand on the back of my head and gently pulled me in. I reached up and put my hand around his hard tool, the memory of his cock flooding back to me and how much different it feels in my hand than my own. Feeling him react to my touch gave me a rush of control, and the soft moan that escaped his lips as I started stroking him gave me a new rush. The gargling sounds coming from the other side of the couches were intimidating. I really hope everyone is focused on them and not us right now. I gave him a few strokes, seeing precum form at the tip, I had to psych myself up to do this. I had already made out with him; technically, I’ve taken a full load from him the last time we did this. The thought is making my stomach turn, but the moans coming from the taller guy on the other couch from getting his dick sucked started to turn me on. It also brought out my competitiveness. I took another deep breath, closed my eyes, and quickly dove in, taking Trevor as far into my mouth as I could and almost gagged immediately.
Trevor pulled his hands off my head to let me up so I could breathe and try again. “That feels so good,” he mumbled, twisting his fingers through my hair. I was drooling impressively, and my cocksucking instincts kicked in with the encouragement of his words. The more I got into it, the less he pushed, and I realized I had complete control over his pleasure. He only let me suck him for a few more minutes, just as I was finding my stride before pulling me up to kiss me. I was even more turned on by him dancing his tongue with mine, knowing he was tasting his precum with me, and his moans were heating me up.
He pulled me onto him, palming my ass cheeks in a way that instantly got a moan from me. He pulled me into him, grinding me against his naked cock and we both let out a soft moan. I kissed his neck, that strong jawline, then his Adam's apple, which was a new sensation for me, but still hot. He tasted masculine, smelled masculine, felt like pure man and the way his hands pulled at my back and my ass it made me drift off into a horny mental state I hadn’t felt since the last time we were together. He slipped his hands into my trunks, palming my ass cheeks, then maneuvered his wrists so my ass was slowly exposed and I heard the gentle sounds of an audience collectively grunting and groaning at the reveal. The sounds pulled me out of my state of bliss and reminded me I was being watched. I decided not to let it bother me and arched my ass so it was on full display.
Trevor pulled spit from his mouth and brought his fingers right between my exposed crack, using the saliva to lube my hole, gently rubbing it over my hole.
“Ungh, oh Babe,” an effeminate moan came from the other couch. Pulling my attention to see the last two inches of the taller guys dick dissapear into his husbands hole. He only held there for a brief moment before he quickly ramped right up to what I would call pounding the shorter guy's hole. It both scared me and turned me on.
“Oh yeah, you love my dick, don’t you?” The taller guy asked, slamming his hips into the shorter guys ass then spreading his legs into a wide V and leaned in to kiss him, mumbling something I couldn’t hear before he started hunching his hips up into his husband.
Trevor pushed a finger into my tight hole, “Oh shit,” I groaned, forgetting how different it was when I didn’t control the entry. He used his free hand to pull me down to him to kiss. I lay flat on him, feeling his stiff cock grinding into my package. The throbing coming from his dick, knowing he was horny for me did trun me on. He quickly added a second finger, and I hissed, placing my forehead on his and biting my upper lip.
“Just relax,” he whispered, then licked my upper lip.
I tried to relax, but the second finger was being met with an even tighter sphincter than the first had. Trevor could tell, and gently pulled it out, rolling me onto my back, he quickly pulled my trunks off, tossing them behind him, no doubt hitting one of the guys watching because there was some quiet murmuring and a chuckle or two after. Trevor quickly pushed my legs up, and for a second I thought he was just going to fuck me, but instead, he spit on my hole, then I felt his tongue lap at it. I sucked in air, “Oooh, fuck,” I felt my hole instantly accepting his tongue. I felt him smile from my reaction as he pushed my legs further back toward my chest. I helped by holding my legs at the knee so he could use his hands to massage my thighs and ass as his tongue worked it’s magic.
I heard more moaning coming from the chaise next to us and turned my head to watch them. They had built up a good rhythm, and the taller guy now had his husband in doggy style. The shorter guy had his back arched and his face looked euphoric with every down thrust his ass took. How he was able to take that kind of fucking and jerk himself off at the same time I’ll never know. I will say it was hot as hell to watch, and even though I wasn’t allowed to acknowledge the audience, I let my eyes slowly drift across the room back to the action happening between my legs. I noticed in the shadows that a few of the men had paired off and were touching each other while watching the show, and that turned me on even more. Some of the silhouettes even looked like they were stroking themselves.
“Ahhgh,” I winced when Trevor pushed two fingers inside my wet hole instead of his tongue.
“Sorry,” he whispered and then took my dick in his mouth as he used the fingers to stretch my hole gently. I tried to focus on the pleasure of his wet mouth to help me relax. He gave me a few more minutes of stretching before he pulled out. “Roll over,” he whispered, reaching for the lube on the end table. Then he poured a stripe along my ass, using his dick to smear it up and down my crack, even letting his helmet tease my hole which got a moan out of me.
“Condom,” I whispered to him, over my shoulder as I folded my arms and put my head into the cave it created.
“Of course,” he said, leaning over and grabbing one of the condoms. I listened to him stroking his lubed up cock before he tore open the wrapper and made a dramatic show of putting the conom on. I heard some groans when the condom went on, but fuck them.
Trevor squirt more lube on his sheethed cock and then started feeling around for my hole. I braced for him to push in, the head found my hole, and he added pressure, then a little more, and with an incredibly sharp pain, the head popped in. “Ahhh…shit,” I groaned. He shifted his weight on me as my hand flew back to instinctively stop his hips from pushing in. I felt his taught abs, clenching as he sank an inch into me. “Fuuuuck,” I whimpered.
He leaned over me, enough of his dick in my ass he didn’t have to hold it with his hand and both hands went to the sides of my shoulders. His head dipped to mine and he whispered, “You gotta relax, man. You can’t back out now, none of us get paid if you don’t take our dicks.”
His words rang in my head; he was right. Fuck. It hurt like hell, but I needed to clench my teeth and take it like a man. I nodded to let him know that I understood.
“I’m going to be gentle, but we gotta get this show on the road before they cum,” he said, gently sinking more of his cock into my ass.
I groaned and bit my arm to keep from crying out. I just took deep breath after deep breath until I heard him grunt and felt his pubes brushing against my ass.
“Fuck you’re tight… just relax,” he said louder for everyone to hear.
Knowing he was all the way in made it easier for me to relax. I don’t know if it was the setting or what, but his cock felt bigger than last time, and I was struggling to open up at all. If anything my ass just wanted to clamp down and kick him out.
He rocked his hips, only a few inches, and bottomed back out. “Oh yeah, so tight,” he moaned.
I grunted with each thrust, knowing he was trying to be gentle. Once he was able to pull most of his dick out and thrust in without killing me I reached back and grabbed his ass to pull him into me, letting me know I was ready. He kissed my neck and whispered in my ear, “That’s it baby, just enjoy my dick,” and he did those small circles with his hips that stirred my insides in the most pleasurable way and I moaned for him. He rocked his hips a little harder, the smacking sound now meeting the intensity of the guys on the other couch. Each time his hips smacked into my ass cheeks it sent a shot of electric pelasure into my guts and I felt myself starting to enjoy it.
I couldn’t help but moan in pleasure and curled my legs up so my feet could rub his ass and it made my toes curl when he bottomed out inside me. “Oh fuck, yeah,” I moaned in a labored breath.
He pushed himself up so he could get even more range of movement in his hips, snaking his body into me with each thrust. His cock was rock hard and my ass was now strectched to fit his size and shape perfectly. It felt so good I almost forgot that we weren’t two guys fucking for our own pleasure.
He pulled out, “roll over,” he whispered, grabbing my legs and flipping me onto my back. He wasted no time in reinserting himself, his cock sliding over my prostate and the head burying itself deep in my guts.
“Mmm fugh,” I moaned and started stroking my dick. This felt even better than the first time, the pain had completely disappeared, and each thrust brought me closer to orgasm. I was in heaven.
“Fuck, I’m close,” he warned, picking up the pace.
“Mate, you want to switch?” I heard from the sofa next to us.
Trevor continued hunging up into me, his abs flexing and contracting, his hips slamming into me as I stroked my dick. “I’m gonna cum,” he warned as his eyes rolled into the back of his head and I felt his cock expand inside me and he filled the condom on a hard thrust with a moan and a stiff grunt. “Fuck,” he gasped, then pulled out, pulling his condom with him and slipping it off. He tied a knot in it and tossed it over his shoulder, an audible gasp coming from someone in the audience. Trevor looked over at the taller guy, “Don’t worry, I am already ready to go again,” he stroked his cum-slicked cock. All of our eyes on his impressive refractory period as he stroked himself gently back to an almost full erection.
I was feeling empty, still gently stroking my dick as I watched them high-five and Trevor lined his bare cock up with the shorter guy still in doggy style. He spit on his dick then slipped it in with a loud, dramatic groan. The taller guy got between my legs and started lining his dick up with my hole. He started to press in bare and I quickly pushed on his abs and clenched my hole, “Uhh, condom,” I whispered.
There was a look of confusion on his face, his eyes wide before he processed what I said. “Oh,” he chuckled, “Mate, sorry,” and he leaned over to the end table to grab a condom.
I watched Trevor start working on his second orgasm, with the shorter guy jerking his dick and making faces that I hoped I wasn’t making while getting fucked by Trevor. Then I watched the taller guy struggle to get the condom to roll down his dick, which was about 7” and uncut, but thicker than Trevor’s dick. He chuckled at how many attempts it took him to get it to roll down, his dick going slightly soft in the process, but he got it. Then he lubed it up and stroked his dick back to full strenght.
He grinned at me, with his hair all messy from fucking and his skin glistening, his sexy smile and big eyes made me look like he had a goofy Instagram filter on, but the rest of his body looked like he was photoshopped from a men’s magazine for health and fitness. He put my legs up on his shoulders and fumbled around to hook his tip on my hole and started to push in.
“Ahhh, shit,” I groaned, feeling my hole stretch to accommodate his thickness and his smile grew wide knowing he was the thickest dick I’d ever had.
“Oh, mate, you’re arse is amazing,” he groaned as he bottomed out. His husband seemed to get off on hearing him say that about me and he moaned even louder as Trevor fucked him.
I tried to breath and relax around this thicker cock. Each new thrust made me clamp down even more, though. His dick had a bit of a curve upward that made him rub on my prostate in more of a battering way than a gentle brush like Trevor or even Carl’s dildo. “Fuck,” I bit my lower lip and tried to stroke my dick back to life.
He thrust in a rhythm that varied from slow to fast and back to slow for a few minutes before he spread my legs and dropped his heavy torso down on me and kissed me. Humping into me in shallow thrusts it wasn’t stretching me out nearly as much as it had at first, or maybe I was loose now. I wrapped my arms around him feeling the muscles of his back and spread my legs out wide so he could fuck me and get his nut.
Kissing him was different than kissing Trevor, his lips were thinner, his mouth smaller, his tongue more narrow, it was still hot, and his stubble was just as scratchy. He seemed to be trying hard to fuck through my ass. Each thrust into me, his hips slammed as hard as they could, as if he could get deeper than his hips would allow. I wasn’t sure if he was close to blowing his load or not because his erratic rhythm left me in the dark, and I was feeling like a human fleshlight. The fucking still felt good, but we were clearly focused on his orgasm.
“I’m getting close,” Trevor told the shorter guy, loud enough for the room to hear.
“Ohh, yeah, cum inside me,” he replied.
Both the taller guy and I twisted our heads to watch as Trever gave a few more hard thrusts and then pumped his load into the shorter guy with a dramatic groan that almost sounded like a roar.
“Oh Gawd, I’m gonna cum,” the shorter guy moaned, quickly pulling off Trevor’s dick and flipping onto his back. Pounding his dick so hard and fast I couldn’t even see his fist anymore. He arched his hips off the couch and he cum shot out onto his chest in massive spurts, one spurt with each thrust into the air until his ass fell back down and he stroked out the last few drops and panted.
The taller guy leaned into my ear and whispered, “Can I take the condom off?”
I shook my head and whispered, “No.”
“Mate, I’m never going to be able to cum like this. I’m barely keeping wood,” he rocked his hips into me.
It did feel a bit like the dildo, only softer. “Just keep trying,” I suggested, not knowing what to do.
He chuckled and pushed himself up, putting only one of my legs on his shoulder and bending the knee of the other so he could get at my ass from a better angle. I felt myself stretching in a way I don’t think my hips were designed to move, but he was able to thrust easier into me, and I was still able to jerk myself closer to orgasm. In fact, I was quickly able to get myself close. “Oh that feels good,” I said, feeling my ass start to clamp down on his dick.
“Yeah?” He smiled, thrusting harder into me.
“Oh yeah, don’t stop,” I encouraged him, rocking my hips to meet his thrusts, pounding my dick. “Oh yeah, I’m gonna cum,” I moaned and breathed heavily.
“Fuck yes,” he groaned, slamming his hips into my ass.
I felt my balls getting slapped by his hips, and it was all I needed to be pushed over the edge. My ass tightened even more and he held his hips in me, as my balls throbbed and my cum shot out onto the floor and dribbled onto the sofa. “Oh fuck,” I shook in pleasure, feeling that intensity of cumming while having something in my ass. “Shit,” I huffed. Looking over at Trevor and the shorter guy, making out and cuddling.
The taller guy rolled me flat on my back and pulled his dick out. He leaned over me and kissed me as he stroked himself to get hard again, the sound of the condom flexing loosely over his cock was the only sound in the room. He groaned as he kissed me then said dipped into my ear, “I can’t, I’m sorry, I can’t like this,” and I felt his fist as he pulled the condom off and put it on the couch next to me as he stroked his bare dick back to life. He continued kissing me and I felt his cock growing in lenght and thickness between my legs as he fisted himself, the head now teasing my hole.
I moaned when he adjusted his position to be further between my legs, his head now firmly pressing on my hole as he jerked himself off, “Fuck,” he thrust and the head popped in, his foreskin pulling back to let the precum soaked tip pop in easily to my fucked hole. I couldn’t help but moan, the slickness soothing my aching, puffy outer ring. He didn’t break our kiss and continued to push another inch into me, then another until I felt his entire length inside me.
I groaned under him, I could feel him growing ever stiffer inside me, but it seemed to slide easier than ever. He pulled out and thrust his full length into me with a satisfied hum.
No longer horny my ass wanted to reject him, but it was so silky smooth I couldn’t help but moan.
“Fuck, that’s quite nice,” he moaned as he grind his hips into my ass.
My eyes shot open, fully understanding now that he was fucking me raw. “Wait,” I whispered, pushing on his abs, but he continued to rock his hips into me.
“Don’t make me stop, I’m not long off now,” he was fucking me with the same enthusiasm he fucked his husband earlier. He kissed me and thrust harder, “Mate, it feels so good like this, don’t make me pull out.” His eyes locked on mine as his rhythm started to pick up, and he bit my lip. “Oh shit,” he thrust faster, “oh shit, yeah,” he hunched up into me. “Oh shit, I’m…ungh,” he hunched up into me and I felt his dick throb inside me, pumping molten hot cum into my guts as his abs contracted and his arms flexed to hold him balls deep inside me. “Oh, Christ, that’s…” he bit his lip and moaned, gently rocking himself into me again, with no resistance, his cum coating my anal walls as he slid deep into me. He gave me a few gently, long strokes to really enjoy having my raw ass wrapped around his leaking cock and then pulled himself free.
He got off the couch, went straight over to his husband, and kissed him. Trevor met my gaze and gave me an understanding smile as I lay there recovering from all of it.
I wasn’t sure what to do. I tried not to look out at the audience, hearing fapping and grunting, subtle moans all around us in the dark. I waited for the other guys to make a move and sat up on my elbows to get a better view of them. Trevor gave the taller guy a bro-hug and a gentle smack on his ass and came over to me, putting one cheek on the sofa so his hip was against mine and he leaned in to ask, “you good?”
I nodded and gave him a half-hearted smile. “Good.”
He grinned and gave me his hand to help me sit up. Then we followed the other guys back up the stairs, trying not to look at the audience.
We hustled up to the second floor, completely nude, covered in cum and lube, the smell of sex wafting off the three of them as they led the way up the stairs back to the main bedroom.
“Fuck that was quite the show,” the shorter guy said.
“I can’t believe we pulled that off, I was so nervous,” the taller guy said. “It took everything in me to keep focus, I didn’t think I’d be able to cum.” He giggled.
“Do you guys want to shower?” the shorter guy asked.
Trevor looked at me. “Honestly, I kinda just want to go back to the hotel and maybe soak and pass out. That was…a lot for me,” I told them.
“Yeah, we can shower at the hotel. I’m spent,” Trevor said, looking at them.
I used a paper towel to wipe the cum off me before pullling out my spare underwear, a pair of flannel boxers and getting dressed as quickly as possible. Trevor called us an Uber and we said our thanks as we left. I dozed off in the Uber ride back, Trever waking me up as we pulled in.
I felt sore and stiff walking as we took the elevator to our room. I dropped my bag on my bed, bending over to stretch all of my stiff muscles.
“Are you ok?” Trevor asked with genuine concern.
I took a deep breath, touching my toes, “Yeah, just need to stretch.”
He stood behind me, rubbing my back under my shirt, massaging my lower back where my hips connect. “I was surprised you let him fuck you raw,” he said in a nonjugemental voice.
I straightened up, letting him continue to massage my back while I pulled off my T-shirt. “I wasn’t really thinking,” I told him. “Mmm,” I couldn’t help but moan as his kneading got deeper into my muscles. “You don’t think I should be worried, do you? I mean, he said he had all negative test results, right?”
Trevor chuckled, bringing his hands back up to my shoulders and gently pushing me to lie face down on the bed to continue his massage, “Nah, I’m sure you’re fine.” He said with an air of certainty, straddling my legs to knead deeper into my lower back, his thumbs slipping below the waistband of my boxers, and I accidentally moaned again. “So, you’ve only let me and him fuck you?”
I chuckled, “Yeah?”
He ran his hands up my back, I felt his free-balling bulge in his sweatpants flopping onto my ass as he put his weight on me and let out a breath of air that had a hint of pleasure in it. “So you’ve been fucked twice now, and both times let the guy cum inside you?” He rocked his hips and I definitely felt his cock stiffening between my cheeks.
I chuckled, “Yeah, I guess so.”
He sat back up, his hands tracing the lines of my back until his fingers hooked into my boxers, gently pulling them down enough to expose my ass. “Mmm, did you like it?”
I sat up on my elbows, craining my neck to see his face, his eyes focused on my ass, “huh?”
His eyes treaveled up my body to meet my gaze, “Did you like feeling cum shoot into your guts?” He flashed me a wicked grin. His hands massaging my ass cheeks now, the one muscle that got worked hard tonight.
“Mmm, I…yeah…I guess I did,” I let my hands slide out in front of me and stretched like a cat.
“I was jealous, seeing him get to breed you when I didn’t,” he confessed, sliding a finger gently over my hole as he pulled my pants and boxers further down my thighs.
“If it makes you feel better, I liked it more when you did it,” I heard myself say before I could filter myself.
“Mmm,” he moaned and I felt his dick slide between my ass cheeks.
I quickly pushed back up on my elbows, turned my head again to see he had pulled down the front of his sweats, and his hefty cock and balls were dragging across my ass.
“Do you want some more?” He asked, letting the tip of his dick circle my hole.
“Mmm,” I moaned and sighed simultaneously. “I don’t think I can,” I resigned.
“I’ll be gentle,” he stuck his fingers in his mouth and pulled out a wad of saliva and smeared it on his cock, then let the silky cock head tease my hole. The helmet easily breached my hole.
“Ungh…I don’t know,” I felt my blood start to rush to my cheeks and my cock at the same time.
“I just want see if I can feel his cum inside you,” He popped the head of his cock into my hole.
“Ahh…fuck,” I felt a twinge of pain, but was so turned on by everything he was saying, it quickly turned to pleasure. “I don’t know…”
“Fuuuck,” he pushed half his cock into me. “You’re so slick from cum already,” he stopped halfway.
“Ungh…fuck,” I clenched, taking a sharp breath as he passed my over stimulated prostate.
“Tell me you want it,” he held his dick there.
“Ungh, fuck, I…I don’t know man,” I felt my heart pounding, my ass throbbing around his girth.
He sank another inch into me, “Mmm, Shaun, your ass is sucking me in,” he said adding the rest of his inches one by one until his pubic bone was pressed firmly into my ass and he let out a moan.
“Oh fuck,” I felt a sharp bolt of pleasure shoot into my body.
“You want it?” He asked again.
“Just…mmm, just be gentle,” I let my head fall flat onto the mattress.
He rocked his hips into me again, “Fuckin-A, man, I can feel his cum in you, it’s so juicy,” he rocked his hips. “Do you like that?”
“Mmhmm,” I nodded in embarrassment at how good it felt as he started fucking me again.
“Fuck that feels so good,” he thrust faster, not pounding, but rocking in the smoothest thrusts into me. His cock sliding over my prostate the way I love and can’t get enough off. I arched my hips up and stuck my hand under me to grope my dick, squeezing it so hard I’m surprised the head didn’t pop off. “Fuck,” he slammed his hips into me and then pulled out completely. He grabbed my hips and rolled me onto my back again. He spit on his dick and lift my legs, knees hooked on his elbows as he fed his cock back into my hole. “Mmmm, yeah.”
“Oh fuck,” I hissed, feeling his head ping my prostate before pounding into my guts. I started stroking myself fast and hard, focusing only on me and my orgasm. I rocked my hips to meet his thrusts. The silky smooth head sliding effortlessly inside me, massaging my anal walls like his big hands did my back and my ass. I clamped my ass in tune with his thrusts, maximizing my pleasure and it made him moan. I opened my eyes to see this adonis between my legs, pumping his big dick into me as I stroked my cock. “Fuck me,” I told him.
“Mmm, yeah, you love my dick,” he responded with a hard thrust and then went back to deep full strokes, making sure to be gentle but firm. “You want me to add my load?”
I stroked my dick faster, swallowing hard as I clenched and unclenched my ass cheeks with his thrusts, “huh?”
“I’m about to blow, you want me to replace his cum with mine?” He panted as he struggled to hold his orgasm off.
“I…uh…” I stroked faster, feeling his cock swelling and pressing harder against my prostate, more pleasure shooting into my balls.
“Fuck, I’m gonna cum in you.” His tone was sure, and he ground his hips into me.
I bit my lower lip, spreading my legs wider and rocking my ass on his cock, so close to shooting my load I nodded ‘yes,’ and pounded my cock harder.
He thrust harder, “oh fuck, yes,” he hunched a few more times.
I felt my balls start to tighten and his next few thrusts slapped my balls hard enough and pegged my guts in the best possible way, “Ungh, fuck,” I groaned and felt my body quake as my orgasm started deep inside with his thrusting and shot out off my balls, spurt after spurt with each of his hard thrusts as I groaned and shook with all of my muscles tightening and relaxing, completely draining my balls.
“Oh fuck, I’m cumming,” he said in a barely audible gasp of air as his hips slammed one final time into me. I felt his dick pulse inside me for the second time tonight, followed by a small pull out and another hard thrust, this time the pulse included a wet, warm feeling. He groaned and his abs flexed as he twitched inside me, whispering an inaudible “fu–ck,” and collapsed on top of me as his arms buckled from the intensity of his orgasm. He sucked in air and breathed out a heavy sigh of relieve. “Holy, shit,” he chuckled, on top of me, his words reverberating inside me. My cum gluing us together as we caught our breath.
We lay there in post-orgasmic bliss for several minutes before he pulled his spent dick out of me, I felt the cum leaking out with him. “Fuck, that was intense,” he grinned.
I tried to focus on him, but the light on the wall just behind his head made it challenging. I was still breathing heavily, holding my hand up to block the light so I could see him smiling. He slowly got off the bed and went to the bathroom, where I heard the sink running. A minute later he came back with a damp wash cloth and did his best to clean the cum off of my torso, dick and even my ass. The warmth and wetness of the washcloth on my destroyed hole felt so good that I moaned, and it made him chuckle. He tossed the washcloth into the bathroom and stared at me.
“What?” He asked.
I shook my head and let out a deep breath. “This was crazy.”
“Crazy, good?” His eyes closed in on mine.
I chuckled, “Yeah, definitely good, but…”
“Don’t overthink it,” he chuckled. “Take a hot shower and sleep on it. You have a long flight home to think about it, just…enjoy it tonight,” he smiled.
I nodded. That was good advice. I reached out my hand, and he helped me up off the bed.
I brushed my teeth and took a long, hot shower. You would not believe how nice the showers are in the Beverly Wilshire.
Comments
Burn After Reading
That part did it for me too.
Arovec
This one was amazing, the last scene especially!
Brendan Gavin
More please
