Shaun - $20 is $20, Sex is Sex

I grew up poor, one of 7 kids in a mixed-race family outside of Boston. After I graduated from high school, I couldn’t afford college and took a job waiting tables at a TGI Friday’s. It wasn’t good money, but because I’m a good-looking guy, I make good tips. Is it enough to survive in this city? No, it really isn’t. I really struggled when the pandemic hit. I got put to work in the kitchen, making poverty wages, but it was better than being unemployed.

I had to supplement my income, and the internet provided clever ways to do that. I’m not gay, but I found that gay men would pay me money to send them my socks or underwear if I sent them with a photo of me wearing them. It was the best side hustle I could do in pandemic times. I found that I could purchase a pack of boxers for around $20 for a three-pack and sell each pair for $20 or more. It was awesome. I ran this hustle for quite a while. Eventually, I found that I could buy a six-pack of white Hanes briefs for less than the boxers and sell them for more than the boxers. 

The comments these guys would send me about my body and the things they wanted to do to me or have me do to them took my confidence to another level. Most importantly, it supplemented my income and saved a little money. I ignored all the creepy emails from guys telling me the things they wanted to do with my body. If they weren’t buying, I had no interest in their fantasies. I even started doing some at-home workouts to really make my muscles pop for the photos, and could use those photos of me working out as online bait to get more guys to buy the underwear.

One particular repeat client was always tipping me extra and giving extra instructions to fulfil his fantasies. It started reasonably innocent. He would ask for a particular brand, color, style, whatever, always tipping a little bit more with each request. Then he took it a step further, asking me to jerk off and use the underwear to clean up with. I didn’t care, I was jerking off for free into the toilet, might as well cum on the underwear for him if it meant he’d send me more money. He would always ask me things like, “Would you ever be with a man?” I would always respond with a vague answer, I’m not trying to lose him as a client because I’m straight, that’s just foolish.

As time passed and things started to settle back to normal, I kept up my side hustle and got more comfortable with the arrangement, especially with this guy. I found myself making videos for him, sending the video of me jerking off and cumming in the underwear and then would mail it to him. His requests would always push me a little further and pay me a little more each time.

Carl: Your latest delivery arrived….mmmm.

Me: I’m glad you are satisfied. 😉

Carl: I loved watching you finger yourself in the video too, fuck what I would give to be your fingers.

Me: lol, I didn’t think I would like it, but wow, you were right! I don’t think I’ve ever cum that much, those Calvin’s are coated.

Carl: Mmm, smells and tastes just like you.

At first, our conversations made my skin crawl, but after a dozen pairs of underwear that he had way overpaid for, I didn’t mind fueling his fantasy, especially since it kept him coming back for more.

A few weeks later, I found myself in a bit of a bind. My dad had thrown his back out at work and was out of work for a couple of weeks. My siblings and I all pooled as much cash as we could to keep my parents from falling behind while he recovered, but since I was the only one of my siblings not in debt up to my ears with kids to feed, I was getting the brunt of the bills.

After work, I found myself on my laptop, putting together a spreadsheet of what bills could be set aside and for how long, but it wasn’t going well. I needed a chunk of cash and fast.

Carl: Hey, cutie, you’re online pretty late.

Me: yeah, I just got home from my shift, just finished my shower, and was looking for some porn to jerk off to. [I lied]

Carl: Mmm, fuck that sounds hot, I’ll send you $20 right now if you snap a pic for me.

I hadn’t just showered, but it was easy enough to fake. I stripped off my clothes real quick, got my dick hard and wrapped a towel around my waist, giving myself a mist with the plant misting water. I took a pic of me lying in bed, my bulge hiding behind the towel, and sent it to him.

Carl: aww, damn, so sexy. Those cum gutters of yours should be illegal.

He sent me the $20.

Carl: Now, what will it cost to get you naked?

Me: You know what it costs 🙂

No sooner did I hit send, I heard my cash app chime, another payment from Carl. This guy was great. I pulled the towel off, gave my dick a few tugs to get a drop of precum to form at the tip, just the way he likes it, and took another photo for him. I took another in anticipation of his next request, this one with me laying on my back, legs spread and knees up, stroking my dick, a particular image he once described in one of his fantasies about me, something about how he’d love to find me in a hotel room in that position and then get between my legs and fuck me like a straight twink needs to be fucked.

Carl: Mmmm, you’re such a tease.

Me: You can’t afford for me to not be a tease 😜

Carl: How much would it cost for me to send you a dildo and you send me back a video of you using it on yourself until you cum?

I rolled my eyes at this one, but with my open spreadsheet in the background showing how in debt my parents are and how I’ve already depleted my savings, I thought I might take advantage of this opportunity.

Me: $1000 lol

Carl: I’m going to send you a dildo to your return shipping address, when you get it, I’ll send you $2000.

Me: Why $2000?

Carl: I want you to livestream the video to me.

Me: I don’t know about that.

Carl: Just you and me in a Zoom. Don’t worry, I’ll keep my camera off, I know the idea of another guy watching you will make your big dick go limp.

I gave this some thought. I had fingered my ass recently for him, but I hadn’t ever thought about using anything bigger than two fingers. I’ll admit the two fingers really did feel good…and I might have added that bit of pleasure to my regular jerk-off sessions when I need to dump a load on a jock strap or some boxers for my other clients and I’m not in the mood.

Me: Overnight it so I don’t chicken out.

Carl: It’s already in the box.

The next day I worked my shift and got home pretty late. There was a package leaning against my door when I got home. I took it inside the apartment and opened it. Yup, it was a dildo. The packaging was weird, though; it wasn’t sealed. I pulled it out, it smelled new and looked new. I washed it off in the sink, noticing how detailed it is. I was expecting something shaped like a rocket maybe, but this was very clearly a hard penis. I dropped my jeans, and sat in my task chair, letting the dildo rest next to the bump of my own dick in my white Lacoste boxer briefs and then sent Carl a message.

Me: Damn, you couldn’t get me a smaller dildo? I was hoping for a small vibrator, like 4 inches. This must be twice that.

I showered, checking to see if Carl responded when I was done. He hadn’t. Sometime around 1:00 am, I heard my Cash App chime on my phone. I looked, it was Carl, sending me $2000. My heart started racing. Holy shit, this guy is for real, and must be loaded. I refreshed my messages.

Carl: It’s 8.5 inches, it’s a clone of my dick.

Me: What do you mean?

Carl: I used a kit to make a dildo clone of my dick, so that you could use it on yourself.

My first reaction was to be grossed out, I was holding a silicone version of Carl’s hard dick in my hand. I was also impressed. I just assumed Carl was white, and from what I’ve seen in the gym locker rooms…white boys don’t pack that kind of heat.

I quickly went to my bedroom, where I keep my lube, so I don’t rub my skin off shooting loads for all the deliveries I’ve been making. Oh, and that one finger session for Carl. I also grabbed my pipe, quickly packed it, and took a few hits before checking my messages again.

Carl sent me the Zoom room information along with some specific details of how and where to place my camera so that he could enjoy the video.

I took another hit off my pipe and then did two back-to-back shots of Hennessy before settling in my bed to start the stream with Carl.

I wanted to put on some music so it wasn’t so awkward, but he insisted he would rather hear the natural sounds I make, demanding no fake “porn-style” moaning from me.

The stream started, and as promised, I had the dildo sitting on the nightstand next to me, lube next to it, and was only wearing a pair of white CK briefs that I would send him tomorrow morning. I started by rubbing myself from the outside of the underwear, getting myself hard, letting my 7.5 cut, thick inches snake up the side of the briefs and letting the fabric strain to contain me as I flexed my most important muscle.

At first, I was a little nervous and uncomfortable, knowing that behind that black square on Zoom was Carl, most likely stroking himself. But the more I thought about it, the more it kind of turned me on. Not that it was a man, probably in his forties or fifties, but that someone was getting off by watching me play with myself. 

I took my time, teasing myself through the underwear. I would grope myself, shaking the covered package for the camera. Eventually, I felt the need to free myself. I let my dick dramatically spring free, smacking my abs, the sound echoed through the room and I realized why Carl didn’t want any unnatural sounds in the room because the microphone wouldn’t pick up subtle noises like that. I let out an soft moan from the pleasure of my dick being free.

I tucked the waistband under my balls and slowly started to stroke myself. I tried to remember all the things Carl had written me about what he would like to see from me over the last year of him sending me money for pics and cum coated underwear. Things he imagined in his fantasies. I spread my legs and the waistband tightened under my balls as I stroked myself.

I made sure to drag this out for him; I wanted to make sure he was a satisfied customer because I can’t imagine anyone else paying me $2,000 to jerk off. And if I know Carl, if he’ll pay for it once, he’ll pay for it twice.

After a few minutes of gentle stroking, and flexing, edging myself close enough to orgasm that I could start playing with my hole, I slipped off the briefs and set them next to my hip so the camera could still see them. I stroked myself completely nude for a few minutes, faster and with more enthusiasm, edging myself again to the brink of blowing my load and then quickly taking my hand off my cock so I didn’t accidentally push myself too far.

As requested, I put an extra pillow under my head to look right down the camera lens. Then squirt some lube on my dick and used the excess to rub my hole. Spreading my legs wide for the camera and some added pleasure for me, I started to push the lube into my sphincter. The sensation wasn’t foreign, but it always took a few seconds for me to adjust to it and for it to go from “uncomfortable” to “pleasure,” but once it became pleasurable, I would quickly get off. This time, with two fingers stretching my hole and giving me pleasure as my other hand stroked me closer and closer to popping off, I had to remind myself that I had more to do. This isn’t for my pleasure, this is a job that I have to do.

I pulled my fingers from my hole, quickly grabbed the dildo. In this light, knowing where I was about to shove it, it looked huge. Especially since the two fingers I just had in my ass felt big and they barely fit around this fucking thing. I lubed it up, stroking it for the camera, knowing it was essentially me stroking Carl, and even though he didn’t request this, I gave it to him for free. Spreading my legs as wide as I naturally could, I dropped the dildo below my balls and started using the tip in my crevice. It felt blunt, considerably bigger than my fingers, and I started getting nervous that I wouldn’t be able to do this and Carl would want his money back.

Stroking my dick with my right hand, I found my pucker with the tip of Carls dildo and used the tip to massage my hole until it felt good. This took a few minutes, but knowing I had complete control of this situation, I decided it was time to push it in. My hole instinctively clenched as I tried to push it in, but once the head popped in, I rested. Sighing a loud breath of air as I adjusted my tight ring to the girth of Carl’s clone, I took another deep breath and pushed it in another inch.

“Ahhh, ungh,” I groaned. This was so much more than a couple of fingers. I had to stop after about two inches. I bent my left knee so I could use the heel of my foot to hold the dick from popping back out as I took a few deep breaths and stroked my dick. After several good strokes, getting my dick back to full strength I was feeling that discomfort turning to pleasure and noticed that a subtle rocking of my hips made it poke my prostate and that felt really good. I couldn’t help but let out a soft moan of pleasure and knew it was time to push it further.

A few more strokes bringing me closer to the edge, I let my left hand drop to my balls for a little tug and then grabbed the base of Carl’s dildo and slowly sank it a few more inches into me, not stopping until the head hit a point inside me that was too dry to open up easily. I left it sit there, at least five inches deep inside me as I adjusted and stroked myself some more.

Using the heel of my foot to hold the Carl…I mean the dildo inside me, I was able to use my free hand to play with my balls as I furiously stroked my dick until the full feeling inside me turned back to pleasure. I slowly slid it all the way out, added more lube, and slipped it back in a little too eagerly, the instant sting shot up into my body in a way I never expected, and I groaned like a bitch. “Fuck,” I whispered, holding it still. I thought since it was already in me that I could at least push it to that point before it would be uncomfortable, but fuck me that felt aweful.

Breathing heavily, I slowly pulled it back out a few inches, then pushed it in a few inches, repeating the action until it didn’t sting and almost felt good. I started stroking my dick again, which had mostly deflated from that intense sting, but with a few strokes it quickly came back to life. I continued sliding the dildo in and out slowly as I stroked, timing it out in a way that felt really good on repeat…really good.

“Mmm,” I groaned, fisting my cock and gently rocking my hips as I pushed the dildo in and pulled it out. “Fuck, that feels good,” I mumbled for Carl to hear because it did feel good, he was right.

After a few minutes of pumping Carl’s clone in and out of me, I was able to get it almost to the base. I knew he wanted to see it all the way to the base, so I continued to stroke myself furiously, getting myself close to popping and using that pleasure to push the dildo a little deeper and a little deeper. I quickly found myself having to push the dildo with more force as I got closer to orgasm, but instead of being painful, it was all pleasure. I was writhing on the mattress as I pushed it and pumped myself at a rate of five strokes for every pump of the dildo, and I could feel the biggest orgasm building inside me.

My balls started to tighten and I started to breath heavier and louder, “Fuck, I’m close,” I warned the camera. Rocking my hips, stretching my legs wider as I pumped the dildio in even deeper, fisting my cock I flet my hole start to clamp down and I shoved the dildo all the way in to the base. “Ungh,” I groaned, feeling a pang of pain and pleasure as I pumped myself for a few more strokes, “I’m cumming,” I groaned breathily. The first intense shot of hot cum flew out hitting my chest, the next landing just below it in the divot where my abs met my pecs, the next few landing in the ridges of my six pack until the last of it pooled onto my fist. “Fuck,” I collapsed onto my mattress as my ass pushed the dildo out completely and I lay there panting.

I gave myself a minute to enjoy that incredible orgasm before remembering Carl was watching me. I felt immediately disgusted with myself for taking things this far, so I grabbed the white briefs next to my hip and used them to mop up the cum off my torso, my fist, and my dick. Then I turned off my camera and exited Zoom. He got what he paid for; I didn’t want to stick around and chat.

*********

I used the cash Carl sent to help my parents make their mortgage payment. It wasn’t enough, though. They had been living with two payments past due for most of the year because of the pandemic, and the late fees were killing them since they basically lived paycheck to paycheck. I got into a fight with several of my older siblings for not letting me know they were this far behind, and that didn’t help the situation. 

Once my dad was feeling well enough to go back to work, I knew he wouldn’t take any more money from us, but I also knew they would never be able to get out from under these back payments. I asked my mom exactly how much they needed to get caught up and stop paying late fees, assuring her I already had the money and that it wouldn’t be charity that they could pay me back at their leisure, but it would keep them from wasting money on late fees. She said she didn’t know exactly but said it was two mortgage payments and a few other bills, at least six grand. I told her I would come up with the money and that she was never to tell Dad.

“Where are you going to get the money? You’re not doing anything illegal, are you?” The look on her aging face made me uncomfortable.

“No, of course not. Look, I’ve been saving and investing for a while because I want to buy a condo in the city,” I lied. With the market what it is, I’m not buying any time soon, so I’d be happy to loan you guys that money,” I continued, knowing I lied to her face, but also knowing they’d never pay me back, so it was a fair lie for a lie.

She looked at me with that “I know you’re lying” look, but sipped her ginseng tea and sighed relief. “Well, if you can help, I know it would be a huge relief,” she said, and then, after a long pause, changed the subject so neither of us would have to continue lying about the situation.

When I got back to my apartment, I checked the orders for underwear, and it was barely enough to buy a fancy dinner, not enough to cover any mortgage payments. I logged in to my Instagram where I had my ongoing DMs with Carl. I started and deleted a few messages to him, eventually landing on:

Hey, did you get that last package?

As an ice breaker since the last time we interacted was the Zoom call last weekend where his cloned dick was in my ass.

Insta didn’t indicate he was online, so I went about my day, showering and getting ready for my job as a waiter, where everyone would be stingy on the tips and treat me like a slave. 

When I got home, I took another shower to wash away TGI Friday’s smell and then checked my messages.

Carl: I did cutie ♥️

Carl: I cant’ help but notice that was the most cum you’ve shot for me. A coincidence, I’m sure 😉

That was two hours ago.

UndiesGuy: Well, I did save up a few days knowing I would be doing that for you.

After a minute, I saw that the message had been read, but there was no response.

UndiesGuy: And if I’m being honest, it felt much better than I expected.

Carl read that and responded.

Carl: I could tell, and I really enjoyed watching 💦

This made me both laugh and cringe.

UndiesGuy: Hopefully you can enjoy that video for at least a few more screenings.

I was hoping to get him to tell me he wanted another video already, or at the very least send me a few more pic requests so I could cash in on him being a perv.

Carl: Oh, I’ve already watched it several times. Wishing it was really me that pushed deep into you, making your toes curl and pushing you over the edge like that.

I decided to feed his fantasy.

UndiesGuy: I’m not gonna lie, it took me a few days to recover from that orgasm. I can only imagine how good the real thing feels.

Carl started typing, then deleted the message a few times. I was antsy, hoping that whenever he finally hit send, it would be a request that would get me at least another two grand out of this guy. It took him another two minutes to finally hit send.

Carl: Unfortunately, I live on the West Coast and have no reason to be anywhere near your area.

That was it. There was no request for more, and there was no hint that he would request more in the future now that it had gone this far. I felt almost rejected, like I was losing him as a client altogether and at the worst possible time.

UndiesGuy: Yeah, I get that. I guess I’ll never know what the real thing feels like. I get to keep the clone, though, right?

Carl typed and deleted a few times again. This time, the anticipation was killing me.

Carl: Well, I can get you the real thing tonight if you want.

My heart skipped a beat. What did that even mean? More importantly, how far was I willing to go?

UndiesGuy: For the right price, I could make myself available tonight.

I sent and then grabbed my bottle of Hennessy and took a swig straight from the bottle. My heart was pounding, waiting for any response. He didn’t say anything, not even typing and deleting. Fuck.

I took a few more swigs of my Henny, and waited anxiously. He’ll probably ask me to go too far and not pay me enough; I must have sounded desperate. He’s going to tell me to fuck off. He probably is thinking I’m not actually straight and that he’s wasted his money on me all this time.

Carl: I have a friend in Boston, about a 45-minute drive from your address. I’d pay handsomely to see you two together, to watch you let him pop your cherry.

My brain melted. It took me a few readings of this message to let it sink in. How far was I willing to go?

UndiesGuy: Define “handsomely?” What exactly are you asking for?

I took another swig, went to my bedroom to get the pipe, and packed it with some good stuff. I can’t believe I’m even contemplating this. Would this make me gay? It’s not gay to do it for money, right? I took a long drag off the pipe. What is my price? I need to set a goal before he responds, so I know exactly what I’m worth. I did the math in my head for how much my parents need to get caught up, how much I could recoup of my losses from bailing them out with my savings, and then rounded up. Knowing how low I could go, I added another grand onto that in my head as a starting point.

Carl: If you’re serious. I would want you to stream it live for me again. Starting the Zoom before he gets to your place so I don’t miss anything. You answer the door in a pair of tighty whities (whatever you have in stock). You let him pop your cherry, you send me the underwear coated with the jizz, no big deal.

No big deal! I chuckled to myself, taking another hit off my pipe and then jumping up and down a few times to release some energy and work the Henny into my system more quickly. I started typing before I lost my nerve.

UndiesGuy: Ok, but we both wear masks, I’m not trying to catch anything. And for that same reason, he has to wear a condom. I’m not catching his nut, I draw the line at that.

Carl typed and deleted. Typed and deleted. Then, finally, hit send.

Carl: With masks on, it won’t be as sexy, but I get it. Condoms are fine with me, just make sure he blows in you, in the condom, and then tie a knot in it and send it with the undies. I want your cum and his.

I gave it some thought. Heart pounding. Fuck. Fuck. Fuck.

UndiesGuy: How do you know this guy? He’s not a murderer, right?

Carl: I know him the same way I know you. A young guy jerking his way through college. I’ve never met him in person, but I’ve paid him handsomely for his cum covered undies too.

This made me feel a little better. If Carl was paying this guy for the same things he paid me, he would be at least as attractive as me and around my age. I looked at the clock. It was 9:00 p.m. If he was 45 minutes away from me, he wouldn’t be here until 10:00.

UndiesGuy: What are you willing to pay for this video?

Carl: How does $5,000 sound?

Damn, I was thinking closer to $10k. It is my anal virginity after all.

UndiesGuy: $5k sounds low. I was thinking closer to $10k, after all, I can only loose my anal virginity once.

Carl did the typing and deleting thing a few times.

Carl: Tell you what. If you want, I can farm out this Zoom to some friends. I’ll collect $2k per person and personally pay you $5k. Anything over $10k will be yours and Trevor’s to split.

This sounded like a good deal, and it wasn’t the weed talking.

UndiesGuy: How many people do you think you can get?

Carl: I am already chatting with a couple of guys, at least four and myself.

UndiesGuy: Only you keep the record though, right?

Carl: Correct. That, plus your dirty briefs and his cum filled condom will get you paid. I’ll send you the $5k tonight, and when I receive the package, I’ll send the balance. Are you in?

I did the math quickly. How could I say no? We’re talking about twenty minutes of sex with another guy for enough money that I won’t have to do this anymore.

UndiesGuy: Deal.

Carl: Fantastic! I already told Trevor you were in; he should be there in thirty minutes. I’ll send you the Zoom link in a few minutes, and I expect it to be active in twenty minutes so we can watch everything from the second Trevor arrives. I’ll send the first $5k when Trevor walks in. You get the rest when I get my package.

My heart was pounding. This was all going too fast, and I needed to be on camera in twenty minutes? I looked around at my messy apartment.

UndiesGuy: Deal. Let me go freshen up and I’ll be online in 20.

I did the flight of the bumblebee cleaning of my apartment, especially in the bedroom. Then I did another shot of Hennessy and realized I needed a quick shower. I did my best to make sure my ass was clean and the rest of my body, then toweled off so quickly I know I missed some spots. Dug through the box of new underwear in my closet, I didn’t have any CK hip briefs, which I know are Carl’s favorite, so I put on a pair of white Dsquared2 briefs, which someone else requested a few months ago that came in a two-pack. They fit me pretty nicely, low rise so my “cum gutters” really popped and the fabric had enough give my package fit nicely.

I did one last hit off my pipe to calm my nerves and washed it down with another shot before putting my mask on. I put my phone on the stand I purchased with the ring light attached and set it up in my living room. Then I opened the link and started the stream. There were ten people on Zoom already, including Carl. I did the math in my head as quickly as I can and the number sent blood rushing to my dick. That many guys are paying loads of money to watch me have sex? Before my head could spiral, I reframed the shot to make sure it was wide enough to catch the door.

Then my buzzer went off. Fuck, he’s here. I buzzed him in and waited, trying to look casual standing by the door for this stranger to come fuck me. Wearing only a pair of tighty whities, which I only started wearing this year for these photos. No one had seen me in person in briefs since the 7th grade. I was feeling so uncomfortable.

There was a gentle knock on the door. Even though I was expecting it, I flinched and quickly opened the door. The guy standing on the other side was easily six feet tall, white, with straight silky brown hair that flopped down into his eyes and over his ears. He was wearing a light black denim jacket with black washed jeans to match. A white T-shirt clung to his developed pecs. His Blue eyes sparkled against his blue paper mask as he smiled with his eyes.

“Hey,” he said.

“Hey,” I stared, nervously shaking.

“Can I come in?” He whispered.

“Oh, shit, yeah,” I shook my head, “please.”

He walked in and started taking off his jacket and his backpack. “I’m Trevor,” he said, unzipping his bag and digging around inside.

“I’m, umm,” I tried to think of a fake name but accidentally blurted out my real name, “Shaun.” I awkwardly folded my arms, feeling very naked in this moment. He looked me up and down, focusing on my bulge, which was feeling very shy right now.

“Don’t worry, Shaun, this is going to be fun. Just relax,” he pulled a collapsible stand from his backpack and put his phone in the hook. Then grabbed what I thought was a Bluetooth speaker, “This way to the bedroom?” He nodded to the open door where you could see my bed. I nodded quickly, feeling the shots of Henny finally kicking in and my nerves settling even though my heart was still racing so fast I thought it might blow out. “Grab your rig,” he said as he turned into the bedroom and walked ahead of me.

I looked down at my crotch, then looked around, realizing he meant my streaming phone on the stand.

I set it in the same spot Carl had me put it last time, turning the light on.

Tevor raised an eyebrow as he looked at me standing awkwardly beside the bed. “Get comfortable and relax,” he said.

I slowly crawled on the bed, unsure of how to do this. Wishing I had at least seen gay porn to have a better understanding of what I had gotten myself into. Trevor set the little box on my dresser by the door, then flicked it on, and a blast of light came out.

“Sorry,” he said, spinning it up towards the white ceiling, the room getting incredibly bright, but a soft brightness. Then he folded out his stand and set his phone on the nightstand, spinning it into a wide screen and opening the same Zoom I had on my phone. Trevor looked at me as he set it up and saw the confusion in my eyes. “This was part of the deal I made with Carl,” he shrugged, “This way they can see multiple angles all at once.”

I nodded.

He checked the angle one more time, then pushed the mute button. Turning toward me, he pulled his shirt up and over his head, exposing his toned body. Holy shit he’s ripped. I thought I was in good shape, but he clearly works out. Next, he went for the button on his jeans, wasting no time stripping down to the white Calvin Klein hip briefs Carl loves. His dick was already getting hard and didn’t look small. I got nervous again. I hadn’t asked Carl if Trevor was hung. 

Trevor climbed onto the mattress between my legs, pulling my legs over his thighs that had seen a lot of squats. He ran his hands up and down my legs, “You ok?”

I nodded, “a little nervous, but yeah.”

He chuckled, “Don’t worry, I’ll take care of you. This isn’t my first hookup.” He continued to give me a rub down, his warm hands tingling my body. It was such a strange feeling to have another guy touching me so sensually, but I’ll admit his strong hands were giving me a vibe I could enjoy. Especially when he would move over my bulge, not groping me, just acting like it was on the way to wherever his hands were already traveling. It didn’t stop me from starting to get aroused.

When he groped my upper thighs and kneaded into them, I let out a soft moan. I had never had a professional massage, and this felt really good. His right hand shifted its attention to my crotch, groping my now hard dick through the thin material of the white briefs. “Mmm,” I inhaled deep, my mask sucking to my face and my legs spreading wider as his thumb massaged my grundle. 

“You like that?” He asked, his masculine voice breaking me out of the fantasy I had going in my head with my eyes closed.

“Yeah,” I tried to relax. I didn’t know how or where to touch him, but he seemed to know what he was doing, so I just let him do his thing. All I had to do was what Carl told me to do, nothing more, nothing less, and I still get paid. “Mmm,” I moaned again, the surprise of his thumb sneaking under the elastic leg band went right under my balls and then dropped down fast until it hit my tight hole.

He chuckled, “Nice and tight, huh?”

I nodded.

“This is your first time?” He asked, his other hand moving up my other thigh, that thumb also snaking under the leg band and brushing gently against the bottom of my ball sack.

“Mmhmmm,” I inhaled sharply.

He let his fingers grip the waistband of my underwear, his thumbs circling up to meet his fingers underneath and pulled the briefs down to reveal my hard cock. I insitinctively lift my ass so he could pull them all the way off. He manhandled my legs so he could get them off completely, placing them on the bed next to us, clearly not his first time. His next move was to pull his dick out, pushing the waistband below his balls, his dick was easily as big as mine, probably the same size as Carl’s dildo. It was pale white on the smooth shaft and the head a rosy pink that came to a squid-like point. He shift his weight so he was tighter between my legs, stroking his dick with his right hand and mine with his left.

I couldn’t help but squirm under the intense sensation of his hand on my dick. “Oh fuck,” I moaned, rubbing my head.

“Damn your body is sexy, man,” he said just as he dropped his dick, gripped my upper thigh and let his thumb drift down to my hole again.

“Mmm, fuck,” was the only thing running through my brain and out of my mouth. I had never been touched like this before. Sex with women never involved me being the submissive one, and certainly never involved anal play. My dick was leaking precum already. He noticed too and he wiped it off with his finger, bright it down to his dick and mixed it with the precum dripping from his tip. Then pushed his dick down below my balls and let it find my hole. “Mmm,” the softness of his skin on my tight hole felt better than his thumb, the added pressure from how rigid his cock is felt really good. I popped up on my elbows, looking at him, then the condom and lube on the nightstand. “You’re going to put on a condom, right?”

He chuckled, “We’re not there yet, but don’t worry, I will.” He added a little more pressure from his dick to my hole, just like with Carl’s clone, the added pressure popped Trevor’s dick into my outer ring. This time, I had no control over it, and the sting shot into me like a lightning bolt.

“Ahh, fuck,” I grunted. Both my hands went to his thighs, touching him for the first time; his hairy thighs felt like granite under me, and I pushed on them to keep him from moving deeper into me.

“Relax, just breath,” he massaged my thighs, then up my abs and down to my cock and balls again. My dick loosing life quickly, but he grabbed it with his right hand and started massaging my thigh and balls with his other hand.

“Mmm, fuck,” I breathed deep breaths, trying to will my ass to loosen up, knowing how good the dildo felt I know this has to be better at some point.

“That’s it, I can feel you opening up already,” he grabbed the lube and pulled his dick from my hole, quickly slicking himself up, then slid a well lubed finger into my ass. The finger slipped in effortlessly compared to his cock head. He then added a generous amount of lube to his two fingers and slipped them in. This stung a little, but as he twisted gently and coated my hole with the lubricant, I could feel the whisper of the pleasure I got last week from the Carl’s dildo.

Trevor lube up his cock again and again put the tip at my hole, pushing gently until the head popped back in. This time with just a discomfort and a grunt from me, “Umm…the condom?”

He leaned over me and whispered in my ear, “I will, I just gotta open you up a bit first, or I won’t stay hard with the condom on, you get it.”

My head was spinning, and I nodded, remembering we are not lovers. This is a business deal, and we both had jobs to do. Right now, my job was to let him get in me; the quicker, the better, and then it would be over. 

I took a deep breath with him hovering over me, my eyes locked on his, and I nodded for him to go ahead. He held himself up off me on his elbows, then spread his legs wider which spread my legs wider, his knees dug into the mattress and he rocked his hips, his cock sank a few more inches into me and I let out a groan and a hiss as he let out a moan of pleasure.

“Fuck,” we both said, but with very differentt inflections.

I took a deep breath. Still gripping tightly to his muscular thighs, I clenched my teeth and managed to ask, “Is that all of it?”

He shook his head, and a puff of air made his mask pop up a little, “almost,” he rocked his hips very gently, the same two inches pulling out and pushing in. Then he did it again, and again, then on the third thrust he sank the rest of his cock into me.

“Ahhh….shiii, f—k” I choked out sounds of the words flying through my head as his dick stretched me out. I can’t believe this hurts so much. I can’t believe anyone would ever do this for pleasure.

“That’s it Shaun, now I’m all the way in you,” he leaned down, hooking his hands under my shoulders to grip on thigh and rock his cock inside me to help loosen me up.

“Oh fuck,” I nodded, loosening my grip on his thighs as the intensity of his filling me up started to slowly become less painful and more of just a fullness I had never felt before.

He rocked his hips and then pulled half of his dick out, then pushed all the way back in, flexing his cock when he did. “Oh yeah, that’s so tight,” he groaned. His eyes twinkled as he lay on top of me, clearly smiling under his mask.

My legs were spread wide around him; I could feel muscles stretching that had never been stretched, inside and out. “Fuck,” I groaned, then reached over and grabbed a condom off the nightstand, “here,” I said. Not wanting this to go any further without one.

He nodded, slowly sitting back up, pulling his dick most of the way out, then pushing in an inch, “Mmm, yeah, you’re ready,” he said, pulling out all the way. He pulled his mask off to use his teeth to rip the condom open. He had model good looks, was very symmetrical and very angular, had a strong chin, and had perfect blemish-free skin. Then the mask went back on and he rolled the condom on his big dick. He quickly added lube, stroking himself a few times to coat the condom, and then aimed it back for my hole.

Without warning this time, he pushed in hard, breaching the outer ring easily but not without a groan from me, then continued sinking inches into me until he had to adjust himself to push the rest of his length into me.

“Ungh, fuck Trevor, go slow,” I said, feeling him bottom out.

He nodded. Leaning over me, he scooped his arms under my shoulders, got a good grip, and started curling himself up into me, each stroke feeling better than the last.

I rubbed my hands all over his flat, broad back, feeling the difference of a man fucking me than a woman riding me. The intensity of this guy using my hole for his pleasure was wild. I couldn’t help but enjoy it after a few minutes, completely forgetting about the cameras on us. His thrusting started shaking the bed, a gentle tick of the frame hitting the concrete wall with every thrust into me. The sound came with an internal spark of pleasure when he hit my prostate, and we both moaned in unison. He held me tighter, as I flailed under him, the moans coming from me were natural, but sounds I had never heard myself make before.

I felt the elastic strap of his mask snap, and it came flying off, so he threw it off the bed and whispered in my ear, “I’m not stopping to get another one,” and thrust deep into me. I nodded in understanding, and then moaned when he took the opportunity to kiss my neck.

“Ungh, fuck that feels good,” I moaned, spreading my legs wider and rocking my hips up to feel my now hard dick get tickled by his abs every time he humped me.

“So good,” he moaned. “I’m not going to last long, you better start stroking yourself,” he said. Then kissed my neck again before sitting up high enough that I could get my hand between us and start stroking my dick, two strokes for every one of his inside me. “Oh yeah Shaun, you’re so sexy,” he mumbled, smiling a sexy smile at me, biting his lower lip as he took pleasure from my ass.

I pulled my mask off, it was coated in sweat and starting to waterboard me every time I took a breath. “Fuck, don’t stop,” I said, clenching my ass down on his invading cock. I could feel my balls starting to tighten up and stroked my dick faster, and faster.

“I’m close,” he said and started pounding my ass hard.

“Me too,” I moaned, my legs stretched out as far as the could, my toes curling as I took all the pleasure I could from his fucking. “Oh fuck, I’m gonna cum,” I said loud enough for the camera to hear me.

“Me too,” he said, locking eyes with me.

His next thrust pushed me over the edge, my orgasm started deep inside me where his cock was pounding my guts, I felt my body shake as the first, earth shattering shot of cum flew out and hit my neck. He thrust a few more times, each thrust forcing another shot out of me, and he grunted.

“I’m cumming.” He thrust hard into me; I felt him twitching inside me as his head flew back and his muscles all tightened.

My balls stopped throbbing, but the pleasure and warmth I felt inside of me as Trevor blew his load was overwhelming. I couldn't help but moan with him. For a brief moment, it was like I could feel him shooting off inside me. Then we both relaxed. He leaned over me, smiling as he caught his breath.

“You ok?” He whispered.

I nodded, out of breath. He took a deep breath and sat up straight, looked over at the camera with a grin as he slowly pulled out of me. I quickly grabbed my underwear and started sopping up the massive load of cum I shot before it got runny and dripped onto my bed.

“Oh shit,” he said.

I glanced up at him to see him staring at his dick.

“What?” I sat up on one elbow, still wiping cum off my dick.

“The condom broke,” he looked up at me, pulling his semihard dick up high enoug for me to see his glistening head and shaft with a torn condom bunched up at the base of his cock. He looked at the camera, then looked at me. Then he grabbed the bottle of lube, “dude this is a silicone based lube,” he chuckled, pulling the destroyed condom off his dick.

I shrugged in confusion.

“You can’t use this with condoms, it will break more often than not,” he said, like this is common knowledge.

“Wait, did you cum in me?” I asked, my eyes getting wide.

He couldn’t help but grin, “Yeah, dude, I didn’t realize…I mean, now I do, but at the time I just thought you were tight, and it felt good.”

“So…now what?” I started to feel panicked and sick to my stomach. A dude just nut inside me, that’s nasty.

He leaned over me and whispered in my ear, “now we need to fuck again.”

“Huh?” I started to push him off of me, but he leaned in harder.

“I have to send Carl a cum filled condom or we don’t get paid,” he said, then sat up slowly. Reaching for another condom on the nightstand.

My head was spinning, I watched as he put a new condom on, using spit to lube it up this time, he stroked himself until he was hard and ready to push back into me. “Wait, what about, what about the lube already inside me?”

“I don’t know, but with my cum in side you, hopefully it won’t break this one too,” he lined his cock up with my hole. “Don’t worry, I’ll be quick with this one,” and with that he slowly started pushing into my well fucked hole. The pleasure from the previous fuck had subsided and this felt a lot more like starting all over again. He didn’t wait for me to get comfortable though, as soon as he was inside me he lay flat on top of me, gripping my shoulders he pulled himself deep into me, the squishy sound of him fucking my hole was different this time, he slid easily inside me with all the added lube. He grunted and panted on top of me, thrusting deep, shorter thrusts, with urgency.

After a couple of minutes, it started to feel good again. I wrapped my legs around his narrow waist and ran my hands through his hair as he kissed my neck and repeatedly bottomed out inside me. He seemed to be digging deeper than before, really focusing on his pleasure this time. “Ungh, fuck, Trevor, are you close?” I asked with a hopefulness in my voice.

“Mmmhmm, fuck, so close, Shaun. Your tight ass feels so good,” he thrust faster. Hooking my left leg over his right shoulder he started digging even deeper, pounding into my ass. “Fuck your ass feels good,” he put his forehead on mine and did something that never crossed my mind, he kissed me. Then smiled at me, the lust in his eyes had my ass opening up even more and I raised my lips to kiss him back. He moaned in my mouth, dipping his tongue in to wrestle with mine. “Fuck I’m close,” he said, thrusting a few more times, then kissed me and I felt him shove hard into me, his cock twitching inside of me for the second time in ten minutes. This time I held on tight to him, feeling all of his muscles contracting as he unloaded his second nut in me. “Ungh…fuck,” he collapsed on me, breathing heavily.

I panted in sync with him. “Fuck man, I was not prepared for that,” I chuckled.

He laughed, “Me neither, that was awesome.” He slowly sat up, looking down at his dick still burried inside me, he gripped the rubberband and slowly pulled out of me, taking his cum with the intact condom with him. Looking up at me, he smiled, “There we go,” he said, slowly removing the condom and tying a knot on the end, and holding it up for the cameras. “Thanks for watching.”

He stumbled over to his phone and hung up. Then went over to mine and did the same.

I lay there, sweaty and relaxed, as I watched this naked white boy walking around in my room. “You ok?” He asked.

I took a deep breath, “Yeah, just…taking it all in.”

He chuckled, “Was it really your first time?” He asked, pulling a wet wipe from his backpack and wiping his dick off.

“With a man, yeah,” I admitted.

He grinned, “Cool.” Then he pulled on a fresh pair of black boxer briefs with no label on the waistband, tucking his dick away. “How was it?”

I started to think, sitting up, feeling my stretched muscles like putty inside me. “I don’t know, kinda weird, kinda fun,” I shrugged.

“Yeah, my first time with a guy was...not what I expected. I’m not gay, but sex is sex, you know?” He started packing up his tripod.

I chuckled, “Yeah, I guess.” I used a towel to wipe myself clean.

“I wish I had known sex with another guy didn’t make me gay when I was younger,” he chuckled. “I would’ve had a lot more sex in high school.”

I laughed at the thought. Even though I had his cum inside me, I still felt straight, and he’s right, it was fun, it did feel good, and I don’t feel any more gay than I did before he came over. I slipped on a pair of loose-fitting boxers. Getting a box of ziplock bags and putting my Dsquared2 cum soaked briefs into one of them.

“Can you add mine and that condom to your shipment to Carl?” He asked as he pulled his t-shirt on.

“Oh, sure, yeah. Shit, I didn’t even look to see how many guys were on that call, did you?” I asked.

He shook his head, pulling on his jeans, “Nah, but Carl is really good about that kind of stuff. As long as we hold up our end of the deal, he’ll always pay, and usually pays extra if he sees us going the distance, ya know.”

I stuffed his underwear into the bag. Then picked up the used condom with pinched fingers. I had never touched a condom that had been used by another guy before. I held it up and took note of how much cum he released into it compared to condoms I had filled in the past. Then I put it in the ziplock bag. “What do you mean?”

“I mean, he asks for something…and then gets a little extra. It makes him feel special, like it’s not a weird transactional deal, almost like we are doing this for us, and he’s paying for something else."

“But he did pay for this,” I pulled on a shirt.

He chuckled, “yeah, but…like, when the condom broke, he would’ve still payed us if I didn’t give him the extra nut, and to be honest I could’ve just pretended I came in the condom and sent him one later with a load in it and he wouldn’t know the difference, but,” he circularly guetured with his hands to show things moving forward, “I was honest in that moment and he loves that shit, he loves how real it is.”

“Like how you really nut inside me?” I joked.

He grinned, “yeah, that felt good, I don’t normally get to feel that with things like this because guys like Carl want to see the cum shot or get sent the cum filled condoms. That was a perk for me,” he chuckled.

He was fully dressed, and I walked him to the door. “Well…thanks, I guess,” I said awkwardly.

He grinned, hugged me tight, my bare torso against his denim coat, and whispered in my ear, “Thanks for letting me be your first. It may not feel like a big deal right now, but it will later. Take care of yourself. " He kissed me on the cheek and released me, then he was out the door.

I took a long, hot shower, going over every detail of tonight. Thinking about everything Trevor said, it not being lost on me that he could’ve jerked off that second time but chose to fuck eme instead, and wondering how early he knew the condom broke. I made sure to soap up my ass the best I could, as if that would wash his cum out of me. When I got into bed, I could still smell Trevor and the sex we had a little while ago. My head was spinning from it all, but I fell into a peaceful sleep, wondering how much I would get when that package arrives at Carl’s in a few days.

Part II:
https://www.patreon.com/posts/shaun-20-is-20-125419751?utm_medium=clipboard_copy&utm_source=copyLink&utm_campaign=postshare_creator&utm_content=join_link