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Dressing Up with Dylan - Chapter 2

"We let Scott film us again, and this time he's no amateur"

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“How’d it go?” Dylan asked, taking off his helmet. I’d just gotten home, myself, but I’d balled up the doctor coat in my backpack as soon as work was done because why ride home on a motorcycle wearing a costume?

“It went great,” I acknowledged. “I would’ve been the only teacher there not dressed for Halloween if it weren’t for you, and they already think I’m a stick in the mud.”

“No they don’t,” he assured me, but I knew I already had a reputation for being strict. “They love you.”

“Some do,” I admitted, because I knew that was true of some of my kids. Several of the girls had crushes on me, probably just because I was young (even though I’d told the kids that first day that I was gay) and I played basketball in the mornings, lots of times, with the boys who got dropped off at school early. I was good at it, so they kind of revered me and I let them even though my considerable height advantage made it overly easy to impress them.

“I love you, too,” he grinned, reaching for the wok to start dinner. I gave him nice kisses then, probably ten of them, but we split up when we both started taking deep breaths.

“If I fucked you every time I wanted to, we’d never get anything done,” I said, giving his butt a playful smack before I went to the refrigerator to get the vegetables.

“We’d go hungry tonight, for sure,” Dylan nodded, getting started on the chicken. He was a good cook, but we rarely messed around with whole chickens. We were busy, after all, and often too hungry to cut meat off bones or whatever, but he’d gotten a good deal on this thing, so he did that and made the sauce while I chopped up mushrooms and peppers.

“Just throw the beans in,” he said. “I’m famished.”

I did, but during dinner I wished I’d taken the time to break the dry ends off, because twice those stems were caught in my teeth. “We should’ve done it right,” I admitted, grinding my fingernail between my molars to get at the mini-green-bean-tree lodged there.

“I know it,” Dyl nodded at me. “We could ask Scotty to help us out.”

“What?” I asked, thoroughly confused, but Dyl was confused, too.

“Don’t you think?” he asked, looking at me all open and waiting for my response. “Don’t you think we can try it again, but do it really right?”

“I’m talking about the beans,” I said. “I’m saying I wished I’d taken the time to trim the beans. What are you talking about?” I knew, though, and my suspicions were confirmed when Dylan’s face reddened.

“Nothing,” he nodded. “I…nothing.”

“You want to make another movie?” I asked, trying not to sound judgmental. I wanted to have another movie of us, yes, but the actual making of the film hadn’t been nearly as sexy as I’d hoped and I hadn’t enjoyed the process as much as just fucking.

“In your doctor stuff maybe?” he asked. This was a powerful turn-on for him; no doubt about it.

“Did you have some hot pediatrician growing up?” I asked. “Were you always hoping your doctor would molest you?” That made him laugh but his face blushed even more deeply.

“I don’t have an explanation for it,” he admitted. “But I’d love to have a film of what we did the other day.

“It’s not as fun to film it, though,” I reminded him. We’d had to worry more about how we looked than how it felt, and we’d had to stop all the time to reposition or re-do some move or re-say lines. Plus sleazy Scott was right there, of course, lurking around and trying to horn in all the time.

“Just this,” he promised. “Please?” He was irresistible to me so I finally nodded my approval, and he leaned in to kiss me, obviously pleased.

“He’ll be over Saturday at ten,” he admitted.

***

I was still incredulous when the door rang on Saturday. “I can’t believe we’re letting this son of a bitch back into our house,” I shook my head, opening the door. Scott was there, looking as smarmy as ever, but he had no camera equipment with him.

“Can I get a coffee?” he asked, like I was a waiter, and that pissed me off even though the last time Scott saw me, I literally was a waiter. When I came back with his joe, he was already sitting on the couch with Dylan, going over the storyboards.

The boards were every bit as crudely drawn as last time, with stick figures bending one another over t-shaped tables and banging each other on stairs made of zig-zag lines. I listened for a bit before interrupting him, “We don’t have a doctor’s table, dipshit,” I pointed out, and he looked up at me, like always, with that superior sneer of his.

“We’re on set for this one,” he said, returning his attention to his explanation.

Dylan grinned at me. “Scott does this all the time now,” he explained. “He’s become a professional.”

“So we’re actually porn stars?” I said it before I could stop myself, and Scott smiled when he saw my mouth hanging open like that. He reached up to close it, pushing my chin with his finger.

“How about we keep this shut until there’s a cock in it, sweety,” he quipped, and even I had to admit it; I was ready to listen.

***

“We can’t have porn out there,” I tried to reason with Dylan. “I’m a public school teacher. You’re a lawyer.”

“So?” Dyl asked, opening the clear plastic face on his helmet, and I couldn’t believe he could make himself this dense. “We’re openly gay. This is part of our culture.”

“That is hella bullshit and you know it,” I laughed, but I was serious about my concerns. “It could ruin us,” I reminded him, emphatically. “It could be the end of either one of us,” I yelled, because the light had turned green and Dyl had snapped his helmet closed and taken off. At the next red light, though, he leaned back on his bike and took his helmet all the way off. His expression was stone serious.

“That what makes it so exciting,” he said. “This is a big risk. Take it with me.”

We arrived at the motel Scott had directed us to and parked our bikes across the street because three big vans were taking up all the spaces in front of room 146. “What if someone sees it?” I asked, but Dylan looked at me calmly.

“If someone’s watching gay anal porn, aren’t they in on this with us?”

***

Scott was one of Dyl’s fraternity brothers and he’d stayed with us, briefly, when I was still in undergrad. He’d come home from the Rome campus with nowhere to stay and had spent a week with us, commenting through the wall whenever we had sex and begging, relentlessly, to be included. He’d filmed us doing it, which was kind of fun, and we’d ended up fucking him just for the hell of it, really, even though neither of us really liked the guy all that much. It’d been almost a year since I’d last seen him and in that time a lot had changed.

Scott wasn’t even sure he was gay before, but that was obviously different because he was wearing all that weird leather shit only queers would step outside in, and he also had a boy with him and whenever he’d issue the kid instructions he’d lay his hand, aggressively, on the kid’s ass. “This is my intern, Craig,” he announced, because that was the other change; Scott truly had become a professional and an entire crew of men was already at the hotel when we walked in. The room was cordoned off with white sheets that were weighted at the bottom, hung to look like walls, I presumed, and there was a doctor’s table in the middle of the room, along with a set of stairs leading up to a fake door to nowhere, that had words written backward on the frosted glass. It took me a second to figure it out, but it said, “surgical supplies” on the door, so that explained the story board figures Scotty’d drawn on some stairs, I guess. He planned for some of the scenes to take place in a supply closet, and I didn’t even ask why there’s be stairs right inside a closet door or why a doctor and a patient might ever even find themselves in a supply closet – even a normal one with no staircase. Scott wasn’t too smart, if you were to ask me, but he knew a lot more about making movies than I did – I had to give that to the guy.

None of it was really the way Dylan had wanted it. He’d asked Scott to film us doing what we’d done that day when I was wearing the doctor gear, but Scott changed it all, significantly, and deleted all the dialogue. All of it.

“You’re allowed to say sex shit,” Scott had explained, “You know, like, ‘yeah’ or ‘fuck me’ or whatever, but we’re not including all that corny stuff about how you’re gonna examine him with your dick.” He also changed us around, saying since my penis was bigger it should be the one showing all the time, so I was the patient, this time, and Dylan was the doctor. I wasn’t surprised, either, when Scott informed us he’d play the part of the male nurse who catches us and joins in, but I have to admit it’d shocked me some to hear Scott was planning a double entry scene, with both Dylan and me fucking him at once. I had a bad feeling about that, kind of assuming Scott would say I was too big, at the last second, just so he could get with Dylan, alone. Scott schemed like that.

Dylan had a bad feeling about Scott’s assistant, apparently. “How old are you, Craig?” Dylan asked, and I had been wondering the same thing.

“Old enough,” Craig sounded irritated. He probably got asked that a lot, but he put down all his equipment, suddenly, and took down his pants. This took a couple of seconds because he was wearing a belt and jeans, but when he dropped them he had nothing on underneath and his penis was large – maybe even bigger than mine. “This mature enough for you?” Craig hissed, pointing it a Dylan. It was somewhat erect – probably sitting at about a half-salute, and the boy gripped it a little, giving it a couple of fast rubs to coax it up a little, apparently to impress Dylan even more.

“He’s nineteen,” Scott knelt on the floor right in front of the guy and took that big dick into his mouth. “He’s completely legal; don’t let that baby face fool you.” Craig didn’t look nineteen, and even that big hard-on didn’t convince Dylan, who eyed the guy suspiciously.

“We can’t risk it if that’s not true,” he warned, but Scott quit the cocksucking to assure his friend.

“Show him your ID,” he ordered Craig, who bent down to get his wallet out of the jeans around his ankles. While he dug around down there, Scott moved behind him and quick whipped out his dick – not even undoing his pants – to move it in Craig’s crack. Craig obviously liked that and stayed bent over while he handed his license to Dyl, who examined it carefully, even holding it up to the light in the little hall outside the bathroom.

“Nearly twenty,” he nodded at me, and I was glad the boy was okay because it was turning me on like crazy watching him twerk Scott. That would’ve made me feel terrible, of course, if he was just a minor.

“He’s my drug dealer, too,” Scott explained, spanking Craig’s butt kind of hard. Craig turned around and put his hand on Scott’s shoulder to pull his head down, so Scott was sucking him again, moving his hands all over the kids pert little ass. I glanced over at Dyl because what the hell were we supposed to be doing during all of this? The crew members were all sitting around just like we were, but only one had his dick out and was stroking and watching Scott and Craig. The other guys looked kind of bored, weird as that sounds, and Dylan didn’t know the answer either and kind of shrugged at me before his eyes, too, returned to the sexy show right in front of us.

Eventually Scott stood up and took his own pants down, too, and I noticed his entire crotch was bald; he’d shaved, maybe, or waxed how girls do. “Let’s get started,” he sounded completely professional, which struck me funny since he was now walking around with no pants on. “Are you guys clear on what happens here?”

We were. It wasn’t how we wanted to do it, though, and I again tried to quietly talk Dylan out of our participation, but he looked at me sincerely and whispered, “If you don’t do this, they won’t want me alone. You know that, right?” That probably wasn’t true; Dylan was gorgeous.

“So what?” I asked. “Why can’t we both just ditch this?” I got it then, though. Dylan didn’t want to leave. This was one of his fantasies, maybe, too, to be involved in a real porno like this, even if it meant we didn’t get to be in charge.

“Okay,” I grinned, because I’d do anything for Dylan, honestly, even fuck stupid Scotty. Which was my first duty of the day.

Scott walked in and took my blood pressure, scowling at the dial on the prop and glancing at where a clock might be if it were an actual medical office.

“Lay back,” he instructed me, but there was no clever dialogue like Dyl and I had when we tried this on our own. I was on the real doctor’s office table and there was real paper on it, even. The BP machine was real, as was the little hammer he smacked me with, pretending to find my reflexes. He pushed my gown up, then, but stopped cold because I was totally soft. I didn’t mean to be, but all those oily camera men moving around and dumb Scott touching me all over just didn’t do it for me. Scott shot Craig a look, and there the kid was, his head under my gown and his mouth all over my cock and balls, so wet it left a big spot on the paper beneath me several minutes later, when he finally backed off.

Scott stood watching, looking stern, and he said nothing when Craig ducked away, but motioned to the cameramen with some hand signal, then he tried it again, lifting my gown and moving his hands on my erection. He was turned toward me like he was about to take my dick in his mouth and I was thinking oh please don’t because I hate the way this guy does head, but he said, “Enter doctor,” and Dylan walked in. One of the camera guys moved to catch him as he swaggered up to me, smiling, and looked right at my hard cock in Scott’s hand.

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“Thank you, nurse,” he said, and Scott moved away to sit on the armchair, which was covered with a white sheet. He let his butt hang off the end so his intern could kneel in front of him and eat him, and he sat watching his monitor and us, both, slowly stroking his erection and nodding, apparently in approval. One cameraman shot him and the kid, but four more were focused on us, swarming around us, chatting quietly to each other about who’d lean in where. Dylan was blowing me beautifully – all saliva and softness – but it didn’t feel like very long before Scott returned from his armchair. He pushed Dyl away rudely, in a way a nurse would never shove a doctor, and he climbed up on me, all unceremonious, and pushed down onto my dick until I was in him almost completely.

“Why is the medical assistant on me?” I asked. It’s not that Scott’s ass didn’t feel good, it’s just that I don’t like Scott all that much and I’d always rather fuck Dylan. Always.

“We’re warming up for the big show,” Scott explained, sounding all patient like I’d forgotten what the “script” called for me to do. I knew I was supposed to fuck Scott and then Dyl and I were gonna double-team him, but I’d never really understood why. “You don’t need to know your motivation, Ms. Streep,” Scott snapped, slamming down onto my cock too hard and bending it, uncomfortably. Two cameramen were leaning on me, one on my chest and one on my knees, and they were catching the close up, I guess, of my dick going into Scott’s butt. He was facing away from me, but I could tell he was making faces about me because of Craig’s reactions and I swear I was about to say screw it and quit, but then Scott leaned way back and called over to Dyl.

My dick was still in him, but there was no way for me to move with him leaning back against me like that, but apparently the bottom guy in a threesome of this nature doesn’t have to do much except stay in. Dylan, apparently, was gonna do the real fucking, and he approached without looking at me, staring only at my dick in Scott’s ass, and when he pushed in I couldn’t believe he could get in there. It seemed like Scott’s anus would rip or something, or that his rectum would split apart, but it didn’t and Scott sounded like he was actually loving every second of it. If I’m honest, I gotta admit I was loving every second of it, too.

Dyl was gentle at first and the cameramen re-positioned him slightly so they could have good views, but when they let him really get started, I was thoroughly… I mean, just completely amazed by the sensation. There was a monitor by my face, and it was for Scott but I could look at it, too, and it was outrageously sexy to watch Dylan’s dick stroking mine like that, inside an ass.

I was so contorted and uncomfortable I can’t believe I’d even think about coming, but I felt Dyl’s cock throb and I looked around Scott at him. He was watching our cocks and his mouth was open, and he glanced up at me with something like surprise on his face, too, and whispered, “I’m comin’,” just as it happened. His eyes closed and he threw his head back in the sexiest of moves, and he put his back into the ramming, then, really meaning it as he forced his throbbing cock deep into that chute. I felt his ejaculation against my shaft– a series of powerful flexes followed immediately by gushes of warm fluid in there and on me, and it was absolutely electric, what it did to me. “Aaaah!” I yelled, and I was slamming, too, as best I could, grinding up into Scotty and exploding too, so our cum mixed again, how we like it. His on mine, mine on his.

“Oh my God!” Scott yelled, shocking me out of my revelry. I’d forgotten all about Scott, even though we were fucking him - it’s like I didn’t even remember he was in the room. “I’m coming!” he shouted, like we were far away. We tried to thrust into him, but Dyl’s dick was already so soft if flopped right out of there the moment he moved it. Mine was still hard-ish, so I pumped into the guy as best I could, trying to get deep and give him some pleasure. He was jerking his dick, then, and moaning like crazy, and I felt his orgasm as his ass muscles contracted and pulsed. It felt good, but I was mostly just swimming my dick around in my lover’s cum, enjoying the after-buzz and not thinking about Scott much at all.

We untangled ourselves, all three of us feeling stiff, and I lay back on the doctor’s table, trying to relax. Dylan stood next to it and leaned over, letting his weight rest on me and we just hung out like that, chest to chest, for a long while.

“Can we fuck you, now?” Scott asked, and both of us turned to see who he was talking to. I’d been almost asleep, honestly, and I think Dylan had, too.

“What?” Dyl asked, and Scott repeated the question, obviously meaning Dylan. He wanted to fuck Dylan. This didn’t surprise me at all.

“Want some coke?” Scott offered, accepting a big bump from little Craig, but Dyl declined, thank God. He did blow sometimes, and it wasn’t ever a good experience for him and he and I both tended to sincerely regret it when Dyl got high. “You guys wanna shower?” he asked, then, indicating the shabby stall in the room’s tiny lavatory.

“I do,” Dylan admitted, and I did too, if we were gonna do more, so Dyl left me to go bathe and when he leaned down to kiss me, smelling of clean hair and wet skin, I realized I’d passed out there on our prop.

“Is that all spruced up?” Scotty asked, and he was eating Dylan, which I thought was rude. It was totally unceremonious and he didn’t ask any permission or anything, just shoved his face between Dylan’s fine butt cheeks.

“Knock it off, man,” Dyl scolded, moving away from that scratchy tongue of Scotty’s. “You need some technique, bro.”

“So can we double you?” Scott asked again. “I mean, if I let you guys finish and everything?” he indicated me with a small hand gesture.

I thought sure Dylan’d balk at that idea, and I was fully ready to support him, but he shrugged, instead, and said, “Sure, what the hell?”

“So now we’re making a movie of you being fucked in your ass by two guys at once?” I couldn’t believe this was okay with him. “What if the partners see it, Dyl?” Surely he’d lose his job over this. I might, too.

Dyl smiled up at me, graciously accepting the towel Craig offered him and wiping out his crack where Scotty’d just been. “Go big or go home, I guess,” he grinned, and I had to admit I was thinking exactly that, too.

***

After my shower, we did more of the same foreplay stuff except this time it was on the stairs, getting ready for our second big double of the day. Craig was involved again, but mostly just with Scotty, since I was more than happy to rim Dylan. I spent the time ignoring Scott and focusing entirely on preparing Dyl, who was about to have two cocks in his rectum, but Craig tapped me on the shoulder to talk to me – apparently he’d been trying to get my attention but I couldn’t hear him with my head up Dylan’s muscled ass.

“Try this on him,” Craig suggested, handing me a sex toy. I’m not well-versed in that kind of shit at all, but I know a dildo when I see one, obviously. Dyl and I don’t use stuff like that, but Craig nodded at me, knowingly, and explained, “It’ll stretch him out nicely so there won’t be as much pain.”

That was important, obviously, so I lubed up the item, which was a purple plastic phallus, and slipped it into Dylan’s ass while I continued everything else I’d been doing. Dyl moaned loudly, loving it in a way I hadn’t expected, and his arousal turned me on, in turn. I moved it in him while I gripped his cock, and he reached down to pet my dick, too, which I appreciated a lot, believe me. “Don’t fuck him yet,” Scott was standing over me, eyeing us critically. “He needs to be begging.”

“What about me?” I asked, because I was getting ready to beg, myself, but Scott held up his finger like I should wait for it. Dylan grasped the balls of the dildo, taking it from me and grinding it hard into himself, pushing his dick into my hand with some measure of desperation.

“Fuck me,” Dylan panted, and Scott nodded at me, grinning because he’d told me so. Dylan mounted me and leaned way forward so our chests were together. I wasn’t as deep as I wanted to be, but a good portion of my dick stayed inside. Scott stood behind him and entered him, too, pushing hard to get his bone into what was already a snug fitting ass. I thought Dyl would hurt, but he moaned instead, like it was pleasurable. I tried to move but Scott stopped me. “You stay still,” he instructed, and then he went to town on my boyfriend’s ass. Scott drove his dick in hard with fast thrusts, and the whole thing surprised me. It shocked me that it felt good to have Scott’s cock stroking in there with me, and I was absolutely astounded by how turned on Dylan was.

“I’m gonna come,” he whispered right into my ear, and I could feel his hard cock already pulsing between us. He groaned as he ejaculated in that tight space, gripping the stairs behind my shoulders. He barely moved his hips because he didn’t want either of the dicks to fall out, but when his ass throbbed it made Scott ejaculate, too.

“Oh God!” Scott yelled, and he was slamming into Dyl (and against me, remember) so hard it was actually sexy even though it was Scott. He creamed, then, throwing his cock all the way into Dyl’s ass, and the thrilled thumping of his spewing dick made me catch my breath. It was so hot, actually, I’m not sure how I didn’t come, myself, but I didn’t, in spite of Dylan grunting right in my ear and in spite of Scott’s warm jiz coating my hard-on while our erections shared Dyl’s ass.

Scott pulled out and I pushed in, sitting up on the stair to hold Dylan alone for a moment, but Scott knelt by me and yanked at me, pulling Dylan off me and thrusting my cum-soaked dick into his mouth. That would’ve been hot if Scott were good at head, but the truth was that guy was so lousy at oral I didn’t really want him on me, and I shot Dylan a look and he was there at my aid, immediately. He pushed at Scott like he was jealous (although I doubt he was) and ate my cock hungrily while Scott wandered off to do something else. He was soon back, though, with Craig by his side, and the kid was holding a slender dildo, very different from the one we’d used on Dylan. “Sit down,” he instructed me, and Dylan followed me, never taking his mouth off me while Craig positioned me for the camera, and it was pretty sexy how that boy smiled at me the whole time gently pushed that little thing right into my ass.

It was about the size of Dylan’s index finger, but it was harder, obviously, and Craig demonstrated some detail of it to Dyl before he backed off completely along with Scott, who was wiping himself off with a towel his little guy handed him. Dylan stopped throating for a moment, moving his wet hand on my shaft and grinning at me while he twirled the hard fake finger around in my rectum.

“Ready to come?” he asked, and I nodded at him because I could feel it getting close again, especially with him moving that little plastic penis in me. He moved it up and down, kind of bumping it inside me and making me crazy, seriously, but then he turned the vibrator on and I was absolutely blown away.

Oh,” I managed to say, and I heard the crew laughing and Scott saying, “That’s gonna make him nut.” Probably, I thought, because it felt unbelievably good. Dylan held his mouth over the head of my dick but he was staring up at me with smile in his eyes, and my cock was rock hard in his hand. I moved my hips a little, feeling helpless. I wanted to help him jerk me but I was frozen, somehow, like the pleasure I was experiencing paralyzed me, and I just stared at him, probably with ridiculously wide eyes, while my orgasm stung through me, gloriously. Pre-cum blooped out of my jiz-slit and Dylan licked it off with his tongue but he took his mouth off, then, smiling at me while he waited for what he knew was on its way. The rest of the load arrived in dramatic blasts, spraying all over everything. Dylan got a faceful, for sure, and some splashed onto my own cheek, too, and my chest, because my dick was going wild, thrashing in Dylan’s fist and pointing first this way, then that, sneezing out multiple bursts of white semen everywhere it looked, while I shrieked with giddy ecstasy and my stomach muscles cramped with the intensity of it all.

“Oh. My. GOD!” I finally was able to yell, but even then I wasn’t done. My cock was still flexing in Dylan’s hand, still oozing cum, and Dyl laughed because every time he moved that little vibrator my muscles spasmed in response, joyfully releasing still more semen with every jolt. I laughed too, and when he pulled it out he switched it off then stuck the machine in his mouth to clean it off, which was sweet of him, I thought, and cool to watch. He stuck his finger in me while he did that, and he moved it like he’d moved the dildo and put his lips around my softening prick, coaxing like three more throbs out of me before I laid my hand on his arm. He took my signal and pulled his hand out of me, and he let my spent dick drop gently out of his warm mouth, too, laying it, exhausted, on my stomach.

“It’s okay you didn’t get to talk, then, right?” I heard Scott say, and that made both Dylan and me laugh again, even harder.

“Thanks for this,” Dyl whispered, leaning forward to kiss me back by my ear. I kissed him back by his ear, too, and he leaned into me, warmly embracing me.

“Anything for you,” I smiled. Scott barked orders while the crew worked on breaking down the set, and Dyl and I crawled into the bed to rest, just briefly.

“Probably bedbugs in this thing,” he muttered, almost asleep already, and I told him to shut up but I know I mumbled it, my words slurred by sweet fatigue.

When we woke up, Scott and all his people were gone and there was no sign a movie had been made in the room, no evidence any sex had occurred. But our aching bodies knew.

“Let’s get home,” Dylan sighed, and I was thinking exactly that, too. Home sounded wonderful, and I followed Dyl’s lead, pulling on our clothes, which someone, (probably Craig) had folded neatly on the room’s only chair. We were still groggy as we stepped out into the parking lot, and we let the night air wake our faces for a couple of moments before we started our bikes. “I love my life,” I said, and even though I had my helmet on and Dyl had his on, too, I saw him hear me and he nodded in agreement, a quick upward jerk of his head, which was his way of saying my statement was every bit as true for him.

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Written by KeeganMitchellFinn
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