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[This story was flagged on my Patreon account and is currently in Patreon Jail, so now it's here where it can live.] I’m a pretty heteroflexible guy in the sense that, unlike my friends, I can admit when another dude is attractive, and when dared to kiss another guy at parties, I didn’t feel the urge to pound my chest and act like I was going to vomit from the thought of it. Afterwards, I would shrug my shoulders and tell whatever guy I kissed that he was good, but his girlfriend was better, just to make it less gay. More than one ex-girlfriend had asked me if I was bisexual, and the honest answer was always no. In college, I made friends with a pretty diverse group of people across all of my classes. One person I made close friends with was a girl named Anya. A beautiful redhead with fair skin and fierce green eyes. She wasn’t in any of my classes, but we worked together at the coffee shop across the street from the law building. Anya is a sophomore, and her boyfriend, Shane, is a junior. He comes around every time she is on shift. He seems cool. He’s one of those rich kids, skinny, tall, perfectly trimmed and styled hair at all times, at least two pieces of jewelry every time he goes anywhere, and he’ll dress like he’s homeless even though his clothes cost him hundreds of dollars to look poor. I like him though, he’s not douchey like his friends when they come in with him. Through the fall and most of the spring semester, I got to know Anya pretty well. There were a few parties she invited me to where we would get drunk and shoot the shit. At one particular party, she told me she had a dream about a threesome with me and Shane and how hot it was. The details she gave me had me pretty turned on as well. Hell, I’ve rubbed out a few nuts thinking about her from time to time. However, none of my fantasies involved her boyfriend; to each their own. She shook her head, “It was just…so unlike me, but I guess because we work together and get along so well…well, anyway, I thought it was funny and you’d get a kick out of it.” I laughed, “I’ve never actually had a threesome, and I never pictured a threesome happening with your boyfriend.” I shrugged. I should’ve left it there, but I tend to ramble in awkward situations like this and added, “And I can’t imagine Shane would be down for a devil's three-way either.” Anya shook her head and grinned, “You’d be surprised.” “Wait, what?” I love a juicy piece of gossip. She knows she can’t just dangle something like that out there and not finish her thought. She looked around, “Shane actually put the idea in my head…about a threesome,” she sipped her drink. I was flabbergasted. “Wait, Shane told you he wanted to have a threesome with me and you?” She chuckled, “No…well…I’m sure he would, but he told me he’s done three-ways with girls and guys before and that he enjoyed it. I’m sure he would be down to share me with you if I set it up.” This information blew my mind. Does this mean she wants to have a threesome with me? How do I play this right? I would definitely fuck Anya, but would I be ok to share her with Shane at the same time? What if his dick is bigger than mine and she gets to compare our styles at the same time and decides I’m terrible in bed and tells every girl on campus and I never get to have sex again because of it? “It’s silly, forget I said anything,” she tried to wave it off. I realized my window to make this happen was closing quickly, and I needed to jump through it like Indiana Jones before it closed if I ever wanted to hook up with Anya. “I’d be down,” I blurted out. She nearly spit out her drink. “Really?” “Yeah, I mean, why not?” I tried to play it cool. “I'm not into guys like that, but I jerked it with some buddies back in high school…how different can it be?” She bobbed her head for a minute; you could see the wheels turning as she mulled it over. “I don’t know, it would be kind of hot to have two hot guys at the same time, but I wouldn’t want to ruin our friendship and make things weird at work.” “That’s fair, but at the same time…” I tried to steer her back towards pro-threesome, and as if on cue, Shane walked up and put his arm around her shoulders. He stood about a foot taller than Anya, a few inches taller than me. “What’s going on over here?” He asked, his eyes glassy from smoking with his boys upstairs. “We were just talking about having a threesome,” Anya offered boldly. I felt my blood rush to my cheeks. “Oh yeah? Zach, you never struck me as the threesome type,” he squinted at me. Probably trying to see if I was just trying to get into Anya’s pants. I shrugged it off, “I’ve never done it, but I’m an open guy.” Shane leaned in and whispered something into Anya’s ear that made her chuckle and made me a little uncomfortable. “Shane, we need you,” a guy yelled from the kitchen where they were playing flip-cup. Shane smiled, “I’m coming!” He winked at me and gave me a pat on the shoulder before darting off. Anya rolled her eyes and shook her head as if to say, “Never mind,” and we dropped the subject altogether. I eventually went back to my dorm alone and jerked off thinking of a threesome with Anya and Shane and what I might be willing to do in that situation and where I would draw the line…until I blew my load and then I wrote it all off as I wiped up my cum with a t-shirt. It didn’t get brought up again, and I just chalked it up to a drunken conversation. That is, until everyone returned from spring break, and I received a text from a number I didn’t recognize. “Yo, it’s Shane, is this Zack?” the text read. Me: Yeah, it’s Zach. Shane, as in Anya’s Shane? Shane: No, as in Anay’s ex-boyfriend Shane. She ditched me during spring break…it’s a long story, but it didn’t end well. That would explain why she wasn’t at work on my first shift back. Me: Oh, sorry to hear that. Shane: Nah, it’s whatever. So listen, straight to the point. I got a girl coming over tonight, she’s like an 11 outta 10, makes Anya look like Raggedy Ann, but this bitch has been playing me for two years. A real cock tease. She said she’ll let me hit it if I set it up as a threesome with another dude, so I thought maybe you’d be down. Or were you just trying to get with Anya? Geeze, that was a lot of information to take in. I wanted to tell him I was just trying to get with Anya, but at the same time, I haven’t been laid in weeks, and spring break back at my parents' place was like being in a convent. So my sexual frustration was at a 10. Me: What would that look like? Me: Would we trade off, or would we have to touch each other? There was a long pause with the three dots popping up and disappearing a few times before he hit send. Shane: I’m not sure. This girl is a bit of a freak, so I would expect you’d need to be comfortable with some fooling around between us if you want to partake. Is that something you’re down for? I swallowed hard, staring at my screen and really focusing on the words. Me: Define “fooling around”? I hit send with my heart pounding in my chest. Shane: Lol, I don’t know, man. I guess the real question is, what are you uncomfortable with? What are your limits? I don’t have any limits, except I’m not letting another dude in my ass…tried it, it’s not for me. If you’re one of those dudes who would freak out if she put my dick in your mouth…maybe this is too advanced for you. I was a little stung by the words “too advanced,” like I’m some sort of child. A part of me wanted to go through with it just to prove the rich asshole wrong. Another part of me felt like I was in way over my head. Could I suck a dick? I’ve had other guys French kiss me, and there was groping, but it was for an audience, which made it hot in its own way. There were also those few times I jerked off with friends back in high school, but that’s normal, right? Me: I see. Me: I guess my limits depend on how hot she is? Shane: lol, right on [attached three pics] Me: Oh shit, ok, I get it now! Shane: Right!? Me: I’ve never seen her at any of your parties, she’s fuckin hot though. Shane: Yeah, you wouldn’t. She graduated last year and lives off campus. Anya knew I had a thing for her and made it clear she was never allowed at our house parties. Me: Gotcha Shane: You in or out? I need to text her back. Me: Fuck…I’m in. Shane: Dope! She’ll be here around 10. Feel free to stop by around 9 if you'd like to smoke with me beforehand. It helps me with nerves for things like this. Shane: Oh, and it goes without saying, but anything that happens tonight dies with us, so do with that information what you will. Me: You don’t have to worry about that! I tried to get some reading done, but ended up rereading the same page over and over again until I gave up. I shit, shower, shaved, and brushed my teeth. I even did a little bit of manscaping with scissors to trim back my bush and make it look more manageable. Not that I’m particularly hairy, but a fresh haircut makes my six inches look a little bit bigger. Shit what if Shane is hung like a horse? I put on a pair of black CK Trunks with the white waistband, they make my package look bigger and my ass a little more plump. Nothing I can do about my skinny torso, though, it is what it is. I showed up at Shane’s at 9:15 feeling nervous as hell. “Bro, you made it. I was worried you’d chicken out,” he gave me a bro-hug. “Nah, I’m always up to try new things,” I tried to play it cool. He walked us back to his bedroom. He has three roommates, one is at his girlfriend's place, the other two are out doing their night shifts and will be back late, Shane said with a grin. Shane had a few prerolls ready to go. We started smoking right away, hotboxing his bedroom as we chatted about his epic spring break trip to Cancun. When we were finished with our first smoke, he went to get us some drinks from the kitchen. He slid his laptop over to me. “Put something on, it’s connected to the TV.” He already had Family Guy open, looks like he’s midway through a rewatch, so I just clicked play and let it roll. He came back a minute later with two open bottles of Gatorade, and the color of the contents was definitely off. “What’s this?” I asked. “A special mix for a special occasion,” he said and grinned. “Try it, you’ll like it,” he shrugged and took a sip of his bottle. I took a sip of mine; it had a weird flavor, but it mostly tasted like blue Gatorade. “It’s good, right?” He asked. I shrugged, “It’s alright. I don’t think you invented Glacier Freeze, though, so you only get partial credit for the funky extra flavor.” He laughed, then checked his texts, sending a few before looking over at me lounging on his bed. “Big Family Guy fan?” He asked, then handed me another preroll. “Some episodes are funny, some aren’t.” He lit his joint and chuckled, “Then why are we watching it?” I exhaled, “because it was already open on your laptop…and you said to put something on.” I couldn’t help but chuckle at the question; the weed was suddenly hitting me hard, and I liked it. He shook his head, “I thought you were going to put on some porn.” I felt like an idiot, of course, that’s what he meant. “Oh, well, that was not clear,” I chuckled. “Don’t let me stop you,” I slid the laptop closer to him with my foot. He got on the bed, sliding up until his back was against the wall. He pulled up a video, “Guess we should put on a threesome,” he grinned, and pushed play. The video featured two men and a woman in a bar, playing pool and making bets. One bet led to the next, which was mostly them taking clothes off. I felt myself getting turned on pretty quickly. I glanced at Shane and could see he was tenting in his shorts, making no effort to hide it as he gently rubbed his knob from the outside. It looked huge, and my curiosity was piqued. I felt my phone vibrate in my pocket and pulled it out; I clocked the time, it was already 10 o’clock, but the notification was the low battery alert. “Shit, do you have a charger?” He looked at my phone, “Yeah, I’ve got you.” He grabbed it and went over to his desk, his shorts tenting from his bulge. He plugged his charger into my phone, and it buzzed again as he set it down. When he turned to come back over to the bed, I tried to swing my eyes from his crotch to the TV, but the TV had all three people naked and kissing, three tongues twirling. It made me wonder if Shane was a good kisser. I couldn’t help but look over at him as he climbed back onto the bed. This time, the distance between us was less than two feet. He took a sip of his drink, and I followed suit. Feeling really buzzed, really loose, and really horny I asked, “Is she on her way?” He slid his hand under his shorts and groped himself, “Man, I hope so, I’m so fuckin horny…I could go blind.” I couldn’t help but laugh, but I was in the same boat. The room was getting warmer, or maybe I was getting warmer. Shane must have felt it too, because he reached behind his head and grabbed the collar of his shirt, pulling it off and tossing it on the floor. I did the same, but I don’t think I was as sexy about it. Wait, did I just call Shane sexy? I don’t think I’ve seen Shane shirtless before. While he is on the skinny side like me, he has more muscle definition. I can’t help but notice a bit of a four pack flexing everytime he squeezes his dick in his shorts. His pecs are small, but there is definitely definition where my chest is flat with two dime-sized nipples. Shane checked his phone again, then his eyes went back to the porn. The group on screen was really into it at this point. One of the guys was fucking the girl while the other guy had his head down between the guys ass cheeks eating him out. “You ever been rimmed?” Shane asked. Not looking at him, I admitted, “No. Have you?” He chuckled as he spoke, “Oh yeah, it’s fucking awesome.” He checked his phone again, sighing when he had no message. “Fucking Veronica,” he shook his head. “Is she on her way?” I asked, feeling impatient, strangling my dick in my shorts. He made a frustrated face, “Not sure, she told me she would let me know when she was on her way. She’s only ten minutes from here, but she had to work until 9.” I nodded, trying to do the math in my fuzzy brain. Shane sighed, hooking his thumbs in the waistband of his shorts and underwear, then looking at me, “You mind if I take these off, my dick is straining so hard it hurts.” “No, go ahead,” I told him, hooking my thumbs in mine to get ready to pull them off, but I wanted to see what he was working with first. He quickly slipped his off and let them hang on his ankles. His 7” dick popped out, thicker than mine with a head shaped like a helmet unlike my mushroom shaped head. I know mine is a little smaller, but not much, so I felt confident enough to join him. We’re going to have to see each other naked when she gets here anyway, might as well get comfortable with it now, right? Shane made no secret of checking out my body, letting his eyes linger on my dick as I slowly stroked myself. I tried to pretend like I didn’t notice, but it did turn me on to know he was checking me out. So much so that I felt myself getting a little closer to orgasm than I wanted to be before the real party kicked off. I let go of my dick and grabbed my Gatorade, taking a few gulps. Shane did the same. I got in a good look at his body when he leaned away from me to get his supplies off the dresser next to the foot of the bed. “Do you use lube?” He asked, squirting some on his dick and slicking himself up. “Usually I go dry, but…why not?” I took the tube from him and squirt some on my dick. It was probably a little too much, the excess dripping down my balls onto his mattress, but he didn’t seem to care, and he was definitely watching. We sat there slowly stroking ourselves, watching the three people on screen going at it. I don’t know when they changed positions, but now the guy who was getting his ass eaten was on his back, taking the other guy's cock while the woman rode his tongue. Shane checked his phone to see if he had any new messages. He looked over at me grinning, “I’m so horny,” he started stroking himself. “Dude, me too,” I huffed, loosening my grip so I don’t cum too quickly. “Would you be down for that?” Shane asked, nodding to the screen as he reached over for his weed. I looked back at the screen, it was a close up of the one guys dick sinking into the other guys asshole and I laughed, thinking he was joking. He blew out smoke and passed the joint to me. I could tell from the look on his face that he was serious. I took a hit, “Which?” I blew out the smoke and passed it back to him. “Either,” he shrugged and took a long hit. I chuckled, “I don’t know, I’ve never done anal.” “In any way,” I felt the need to add. He passed me back the joint, “Have you ever played with your hole?” I shrugged, feeling no hangups at this point, “I’ve…dabbled, I guess.” I passed it back to him. “Really? Like a finger or a dildo?” “A finger,” I scrunched up my face. “I do not own a dildo.” He chuckled, “Hey, this is a safe space, you can get dildos that are not shaped like a cock that are designed just for anal stimulation,” he smiled at me, passing the joint back to me. I took a deep hit. “Did you…” His phone buzzed before he could finish his thought. I hoped it was Veronica saying she was outside. I watched as Shane texted back quickly. Then his phone buzzed again, and he texted back again. I took another hit of the weed, slowly stroking my dick with my free hand, watching his dick bob as he used both hands to text. I grabbed my drink and shifted in the bed so I could use the pillows along the headboard. My feet were stretched out on the bed down by Shane, and I could feel the warmth on the mattress from where his body had just been lying a moment ago. Shane sighed, setting his phone on the dresser, then looked over at me as he took his dick back in hand and started stroking it again. “Was that Veronica?” I asked. “She’s running late,” he shrugged. His eyes went from mine down my body, between my legs. “How often do you finger your hole?” I felt my heart rate speed up as I put the lid back on the Gatorade. “Ummm…I don’t know, once in a while, when I’m really horny...and taking my time, I guess.” I bent my left knee up so my foot was by my ass and knee in the air, my right foot tucked in to meet my left like a dead butterfly. I noticed how often he was glancing at my hole, and it was turning me on in a weird way, especially since he was talking about it. He scoots back on the bed, filling the space where my feet were and leaning against the wall. His hips were close to my feet, and I could feel his body heat radiating to my toes. I let my left knee drift to lean against the wall so I could see his face again, his eyes were...locked on my balls? Maybe lower. “How do you do it when you do it?” He asked, his eyes making their way back to mine. I felt a rush of heat hitting my chest, and I passed the last of the joint back to him. His arm brushed hard against my raised knee as he reached for it. “Umm…I don’t know, I just use a little vaseline and…you know,” I turned my hand palm up and started wiggling my middle finger up the same way I would finger a womans clit. “You use your middle finger?” I chuckled, “Yeah? What finger do you use?” He smirked, “I use both my fingers,” he held up his index finger and middle finger. “I’ve done that too,” I blurted out unprovoked. He smiled, “Really? How many fingers have you had in your ass?” “At one time?” He chuckled, “Yeah?” I felt embarrassed but answered anyway, “Ok, one time, I was chatting with someone online, like really filthy chat, and she convinced me to try three fingers.” I couldn’t help but grin with pride and embarrassment. He didn’t mock me like I expected; he actually nodded along like he was impressed. “Three fingers, but you wouldn’t do that?” He pointed at the screen again. My eyes followed his finger and on screen the cut to the close up of the guy on his back getting fucked by the other dude. I shrugged, “I don’t know, it’s way different than fingers.” He chuckled, “not really, I mean, think about it,” he held up his hand, putting the tips of his index, middle, and ring fingers together, then brought it down to his hard dick and lined them up. “It’s basically the same,” he shrugged. “Not even close,” I held up my fingers in the same formation. He quickly sat up and shifted, getting between my legs, pulling my hand down to his dick and I accidentally touched it as he compared my fingers to his girth. “It really is about the same.” I chuckled, “No way dude, look at it,” I put the three tips of my fingers to the head of his cock and it gave me a rush as the velvety tip brushed my pads. “Well, sure, the head is bigger, but how far did you get those fingers in?” I looked at my fingers for a second, “I don’t know, I couldn’t see, but it felt like they were at least to here,” I used my thumb to indicate the section just below my knuckle on my forefinger. He grabbed my hand again and lined it up with his dick which was pumping out heat. “See, at that part I think your fingers are even thicker than my dick.” He smiled with pride about being right. “Maybe it wasn’t that far,” I tried to walk it back. He made a knowing face. “Did you like it?” “I don’t know, I was kinda caught up in the moment,” I admitted. He gave me that look again. “Did you cum?” “Of course.” “With the fingers in your ass?” I thought about it for a second. “I think so, yeah.” “Well, there you go, see, you could do that, and enjoy it.” He looked back at the screen, accidentally resting his hand on my right thigh. We both watched in silence, stroking ourselves slowly for a moment while the camera cut back and forth between the close up of the guy getting fucked and then to him eating the girl out while also stroking his massive dick. It didn’t go unnoticed by me that as he slowly stroked his dick, his fist accidentally bumped into my balls a few times. I’ve jerked off with buddies back in high school before, so I’m not uncomfortable with touching another guy, but I don’t really know Shane this well, and it feels different when he touches me. Good different, I guess, but all this talk about our potential threesome involving anal sex between us has my buzzed brain spinning. Shane let out a soft moan and squeezed my thigh, jerking my attention back to how close we both are, and Veronica hasn’t even shown up yet. Shane was fixated on the TV, and it gave me a chance to really take him in. As he jerked himself off I could see the muscles hidden under his skinny build, and the way he strokes his dick had me in a bit of a trance. My mind kept drifting between wanting to touch it and thinking about Anya touching it. I wonder if she let him rawdog her? Then if I touched his dick, it would be kinda like I touched her pussy….right? “Fuck man, I need to calm down or I’m going to shoot before she gets here,” Shane said, releasing his dick and contorting himself around to reach for a little brown bottle on his dresser. He shook it, uncapped it, then held one side of his nose closed as he inhaled slowly on the other side. Then he repeated it on the other nostril. The way he relaxed immediately and looked high as fuck made me curious. “What’s that?” “Poppers,” he held the bottle out for me to take. “It helps you relax, and when you’re on the edge, it helps you to keep control of your nut,” he chuckled. I took the bottle from him and followed his example. The fumes were intense and holy shit did I get a rush. My heart started racing, and I could suddenly feel every nerve ending in my body as my eyes rolled into the back of my head. “Oh shit,” I whispered. “Right?” He chuckled, putting both his hands on my thighs and rubbing up and down a few inches below my crotch. “Damn, that’s intense,” I felt my head spinning as I relaxed into the mattress. “It’s like a horny drug,” he chuckled. I do feel even more horny. I don’t think I was any less close from blowing my load, but man do I feel horny. Shane grabbed the bottle of lube on the mattress and dripped a good a mount on his dick, stroking himself to coat his meat. “Want more lube?” He held the bottle out. I took it and dripped some more on my dick, again a little more than I wanted to and it dribbled down my balls. I instinctively brought my free hand down and tried to catch the drip. Shane huffed, “Trying to finger yourself?” I chuckled, “No, I was trying to keep the lube off your mattress.” “Oh, here I thought you were going to put on a show.” The idea now planted in my head I did kinda want that anal stimulation. Would it be weird if I fingered myself in front of Shane? Would he even care? I felt his fist bump my balls again as he stroked himself. I’m not sure if he even realized he did it; he was so transfixed on the TV. I liked it, though. I kinda want him to do it some more. I slowly stretched my legs out over his bent knees, his hairy thighs brushing the back of my thighs as I did. He looked over at me as my legs landed. “Sorry, I was getting a cramp,” I lied, but it brought me close enough to the flight path of him stroking himself that his knuckles started bumping my balls with every other pass. “It’s cool, get comfortable,” he said, and then leaned back a little which spread his knees a little more under my thighs, holding himself up with his left hand as his right stroked his dick. Now every stroke of his dick was bumping my balls and it was sending my brain into a horny spiral. I started stroking my dick faster. “Oh shit, that probably feels so good,” Shane grinned at the TV, stroking his dick a little faster. I turned my head to look at the TV and saw the guy getting fucked shooting his load on his chest as the other guy pulled out and shot his load on that guys balls and the camera zoomed in on the juices dripping down to the guys asshole. “Damn,” I added, trying not to cum. “I would’nt pull out though,” Shane chuckled and I realized he was thinking it must have felt good to be fucking that guy as he shot his load instead of being the guy getting fucked. “Yeah, me neither,” I felt the need to add. Then I grabbed the little brown bottle and took another hit. “Fuck, that got me close too,” he said, reaching for the bottle after I inhaled a second time. I watched Shane close his eyes and take a hit, feeling the rush wash over my body, I don’t know why I did it, but as he was taking a hit on the other side I reached out and gave his dick a couple strokes which caused him to moan and he grinned at me through half lidded eyes and I stopped stroking him. Another scene started playing on the TV, featuring two different men and a different woman. This time, they were checking into a hotel, and one of them said, “I’m so glad we’re finally off the road.” She parked her roller bag and added, “I never want to get in the car again,” then stretched her back by bending over and touching her toes. “Do you need a massage?” The second guy asked, and then the music kicked in. “Do you need a massage?” Shane asked and squeezed my thighs, the head of his dick brushing against my balls and then sliding down to my lube drenched grundle before he pulled back. I chuckled, “I need Veronica to get here. I’m so horny.” “Yeah, fuck, me too,” he contorted himself to grab his phone without leaving his spot on the bed. He sent a quick text and set the phone down. Immediately his hand went back to stroking his cock. “You know what would be hot?” “What?” “Ah…no, never mind,” he shook his head and turned back to the TV. “Well, now I need to know,” I pressured. “It’s stupid, I don’t know why I said anything,” he kept looking at the TV. “Dude, come on, what would be hot?” He turned to look at me and grabbed the bottle of poppers, taking a hit as if that would change the subject. Then he handed me the bottle. I grabbed it, adding, “Bro, just tell me,” and inhaled deep. He closed his eyes, still holding his last hit in. Then I took a hit on the other side as he exhaled. “Fuuuck,” he said and squeezed my upper thighs really hard, and it made me moan and exhale my hit. I felt the rush washing over me. I closed my eyes and just enjoyed the sensation and mumbled, “Just tell me.” “Ugh, ok, but don’t judge me,” he prefaced. I shook my head, implying I won’t judge. “It would be kinda hot to see how you finger yourself as you jerk off…you know, while we wait on Veronica.” With the rush at its peak, I mumbled, “Mmm…yeah, it would.” “For real? You’ll do it?” He got all excited. Before I could think about it, I shrugged, “If you want…I mean, it feels good,” I chuckled. He grabbed the lube and handed it to me instantly, popping the lid as he did, which got a chuckle from both of us. My rush started to come down as I poured some lube into my left hand and circled my pucker with my fingers. The cool lube grounded me a little, and I started to think this might be a bridge too far. “Are you sure you want to watch?” He grinned, “Fuck yeah, it’ll be so hot to watch you pleasure yourself like that.” He stroked his dick a few strokes. “Wait,” he nearly shouted. Grabbing a pillow, he pushed my legs back and stuck the pillow under my lower back and upper ass cheeks. “This way I can really see it,” he grinned and grabbed the lube. “Want some more?” He uncapped it. I held out my hand and he squirt a dollop on my fingers, then squirt more on his dick and started stroking himself. I turned to watch the TV. I couldn’t watch him while doing this. I learned the hard way that I had to concentrate on relaxing my sphincter for this to feel good, and with him watching me, there was added pressure. Thankfully, my head was spinning from the poppers, weed, and whatever was mixed in with the Gatorade, so as soon as I took my lubed fingers and circled my hole, it instantly felt good and like I could just go for it. Out of caution, though, just using my middle finger, I pushed the tip into my slick pucker, and it went in pretty easily. The feeling of being gently stretched always felt good, but with his lube, it was even better. “Oh shit, that’s hot man,” Shane grabbed my legs and gently spread them a little wider to get a better view, then quickly returned to slowly stroking his dick which I could see was starting to form precum at the tip so I know he wasn’t just saying that, he was really enjoying what he was seeing. I decided to push it into the next knuckle, which was a little uncomfortable for a second, but as I wiggled it inside, it quickly started to feel good. “Keep jerking yourself too,” Shane encouraged, scooting closer to me in excitement. Now as he stroked his dick his fist was bumping into the back of my hand and I felt the precum from his tip a he accidentally rubbed the head on my hand too. My first thought was that’s gross, but as his fist gently bumped the back of my hand on the next stroke, it vibrated through my hand and into my hole, and that was a new feeling I instantly enjoyed. I didn’t tell him he was bumping my hand, since he didn’t seem to care, and after a few more strokes, I was so turned on I was ready to insert another finger. Still, I wasn’t sure if that was taking this too far or if he wanted to see me do it, so I just kept wiggling my middle finger as deep as I could get it while my right hand stroked my dick in time with his stroking. “This feels good,” I whispered in a breathy voice. His eyes latched onto mine. “Yeah?” “Oh yeah,” I confessed. He put his hands on my thighs, gently squeezing as his cock bobbed up and down and his precum smeared on the back of my hand. “Add another finger,” he suggested. I raised an eyebrow, “Yeah?” “Fuck yeah,” he insisted. “Want more lube?” He grabbed the bottle and uncapped it. “Umm, sure,” I pulled my finger out and let him dribble an excessive amount into the trench between my middle and index finger. Then he put a little more on his dick, giving himself a few strokes as I returned my fingers to my hole. This time, as I slowly inserted both fingers, he watched in awe as I slowly slid them in as deep as they would go. The stretching was intense, but I felt the need to impress him by doing it without stopping. Like, somehow I’m not a man if I can’t insert two fingers without wincing. “Damn Zach, that’s so hot, look how tight your ass fits around your fingers.” Shane's eyes were like saucers as he watched me finger myself with two fingers now. In his excitement he shifted his weight again an was humping his dick across the back of my hand for a few pumps of his hips before he settled back down and started stroking his dick directly against the back of my hand. The vibration with two fingers in my hole was an insane amount of pleasure. So much so, I found myself trying to pull my fingers deeper into my hole than I had ever done by myself. “Does it feel good?” I let out a very breathy, “Yeah.” “Shit, it’s so hot. Is that weird to say? Fuck, I don’t care man, it’s really hot, you look so hot doing it.” He put his left hand on my thigh, leaned over me really quickly, his dick dragging up my arm, precum streaking in my arm hair until his balls landed on my wrist as he grabbed the little brown bottle next to my shoulder. “Dude, you’re so fucking sexy like this,” he almost mumbled to himself as he opened the bottle and put it under my nose, plugging one side and then the other as I inhaled deep without taking my fingers out of my hole or off my cock. The rush crashing over me like a tidal wave. I felt my hole relax around my fingers, and I was able to push them even deeper in. “Mmmm,” I moaned as my eyelids closed and all of my other senses heightened. I felt my horniness increase from the pleasure of my fingers in my hole. My strokes on my cock were intensified, the heat coming from Shane being under my legs and his dick putting off an amazing amount of heat as it rest against the back of my hand was intense while I heard him take a hit of the poppers. “Fuck dude,” he breathed out before taking another hit and holding it. As he breathed it out he grabbed his dick and started stroking himself. I continued stroking myself and fingering myself as the poppers peaked and then subsided, bringing myself back to the edge and then holding off, letting Shane vibrate my fingers inside me with his jerking off between my legs. It was all so surreal, I almost forgot about Veronica until I heard Shane’s phone buzz. He didn’t seem to hear it because he just kept stroking himself while watching my fingers wiggling inside my tight pucker. “Is that Veronica?” I asked. “Huh? Oh, shit,” he grumbled and grabbed his phone. “She just got out of work, she needs to go to her place and shower before she comes over,” he read me the bullet points. He sent a quick text and then put the phone back down. “We can wait, this is already hotter than I thought it would be,” he said, grabbing my thigh with his left hand and his dick with his right, shifting his weight again and I swear he was so close his ball brushed against the back of my hand before he settled. “Should we…wait for her? I don’t want to accidentally cum,” I chuckled. “Fuck that, she’ll get here when she gets here, I’m having too much fun,” he grinned. “Unless you want to stop,” he added. I shook my head no. I was too close to blowing my load to think clearly. The sex fog in my brain had me feeling good all around. “Good,” he said. “Want some more?” He held up the bottle of poppers. I nodded yes. “Yeeeeah boooy,” he leaned over me again. Again his balls dangled over the hand in my ass, his dick sliding along my dick was so weird but oddly a turn on at the same time. He helped me take another hit before he settled back down to take a hit of his own. Capping the bottle he got up on his knees a little, grabbing my thighs he rocked his hips so his dick slid up along my cock and his balls gently banged into the back of my hand and he let out a heavy breath. He did this through the entire peak of my popper high and his until we both settled down and started stroking our dicks again. “Fuck dude, do you want to try for a third finger?” I grinned and nodded yes. I was feeling so good that a third finger could only enhance this situation. Shane grabbed the lube and put the tip just under my balls and squeezed. I felt the liquid hit my grundle and drip down, and I caught it with the fingers still in my hole. “Wait, wait, wait,” Shane said, capping the lube and grabbing the poppers. He stuck them back under my nose, and I took a hit. “Deeper this time and hold it,” he said, holding it under the other nostril. I did as I was told and took a really deep breath until I thought my lungs would pop. “That’s it,” he said, taking a quick hit for himself and settling back down. Then he hooked his hands under my knees and pushed them back toward my chest so he could watch. “Ok, now,” he said, finally exhaling. With the rush washing over me, I didn’t focus on him holding my knees up and just focused on the pleasure of all of this. Slowly sliding my middle and index finger out, I quickly adjusted my fingers and pushed back in slowly, adding my ring finger this time. “Oh shit,” I groaned as I quickly hit the first knuckle and it was already more stretching than just two fingers flexing inside. “That’s it, keep going,” he encouraged. “This is so hot.” I took a deep breath, keeping my eyes closed. I tried to focus on relaxing, and it actually worked. My fingers slid into the second knuckle, and now I knew I was more stretched out than I had ever been, so I had to stop pushing in. “Oh shit Zach, that’s so hot!” Shane's excitement was intoxicating. “Keep going, see if you can get them even deeper.” I slowly pushed even deeper, letting out a groan and clenching my hole around my fingers as I did. It didn’t hurt as much as it was uncomfortable and hard to do from this angle…but yeah, the new diameter was a bit intense. “Ungh, I can’t go any deeper,” I admitted. “Shit, dude, that’s still so hot. Does it feel good?” He let my legs go back down and started stroking himself with his right hand and rubbing higher up on my thigh with his left hand. I groaned, “It’s ok, I’m getting used to it.” He chuckled, “Dude, I’m so turned on by it. I know that sounds weird, but I don’t care, man. Something about it just looks so hot,” he grinned at me. “Can you pump in and out like before?” I tried to pump in and out, but the best I could do was wiggle my wrist, and my fingers gyrated in me a little. “Mmmph…I can’t.” He rubbed both of my thighs up and down, letting his dick rub the back of my hand as he slowly slid his hands up so his thumbs could massage my crotch. “Do you want me to try?” I opened my eyes to see his still locked on my hand or maybe his dick, it’s hard to tell. “What do you mean?” He looked up at me and smiled, “Can I try fingering you?” I swallowed hard, “I don’t know, that’s kinda…you know.” He chuckled, “Dude, it’s no big deal, I’ve let a guy do it to me before, it always feels better when someone else fingers you.” “Really?” “Yeah,” he scrunched up his face as if I asked the dumbest question in the world. “I guess, if you want to, it could be cool,” I said, slowly pulling my fingers from my hole. He didn’t hesitate and reached for the lube, coated the fingers on his left hand, then lifted my balls with his right hand so he could see what he was doing and slowly slid his fingers down my grundle into my crack and then found my pucker. “Oh…ahhhmmm,” I breathed out as he circled the ring and landed in the center. My pucker instinctively tightened before he could push one finger in, but he pushed just hard enough that his finger pushed in and kept going until he had it all the way on. “Ahhh…shit,” his finger was a bit more rigid and overall bigger than mine and it stung a lot more than when I used mine. “Oh shit, that feels so good, holy shit dude,” he comented as he did more of an in and out motion as opposed to the wiggling I did with my finger. “I can feel you gripping my finger dude, that’s so fucking hot,” he chuckled. “Ungh, shit, it’s so weird,” I groaned. “I’m going to put a second finger in,” he said, as he was already sliding the first finger out to add the second, and without pausing, pushed in two fingers. “Oh fuck, Shane…ahhh, that’s, ahhh,” I hissed but then he twisted his hand so it was palm up and did this Spiderman thing where he pressed his fingers hard into my anal wall and I had a rush of intense pleasure. “Oh, shit, that…that feels better,” I was squirming under his assault on what turns out to be my prostate. “That’s the spot?” He pressed even harder with each click of his fingers. “Ungh…yeah, oh man,” I grabbed my dick and started jerking off. The pleasure was so intense I couldn’t waste it. “You like it?” He asked in a breathy voice, stroking his dick with his other hand. I could only nod yes as I breathed heavily and stretched my legs over his thighs, my toes starting to curl from the pleasure. “Damn dude, you’re ass is so warm and tight, it’s like trying to eat my fingers. Do you want me to try a third?” He pulled his two fingers to just the tips as he asked the question, not waiting for the answer, he aligned his fingers and started pushing in. “Ahhhgh, that’s too much,” I groaned. “Let me add more lube,” he said, reaching for the lube without removing his fingers from my hole. “Shit, I don’t think lube will help,” I hissed. “Let’s see, I need more for my dick anyway,” he popped the cap, pulling his fingers out except the tip and added more lube, then slowly pushed them back in. Holding his fingers at two knuckles deep, not moving a muscle, it gave me a chance to breathe. He drizzled more lube on his dick and before he capped the lube he asked, “Do you need more on your dick?” I shook my head no and he capped it, smearing the lube all over his dick. “Damn dude, I’ve never had anything this tight on my fingers. Does it feel good?” I sighed, “It’s alright. Just hold it there.” He did as he slowly stroked his dick. After a minute, he slowly started pulsing his fingers, almost like he was trying to spread my hole instead of fingering it, but it was so gentle it actually felt really good, and I started jerking off to the new pleasure. “Jesus, I can feel your ass clamp down and then relax on my fingers, like it’s your heartbeat. Does it feel good?” I nodded, “It’s better.” I was slowly jerking myself because every few strokes I felt him hit my prostate and it would almost make me cum, and I definitely didn’t want to cum before Veronica got here. Oh shit, Veronica… “Did Veronica text?” “No.” He kept pulsing his fingers. “Are you…mmm….are you sure?” He dropped his dick and reached for his phone. “Nah, not yet.” Then I heard a notification chime. “I put the volume up so we’ll know for sure when she texts.” He put the phone back down and started stroking his dick again. “Shit, I think we should stop until she gets here,” I dropped my dick. “No way, dude, this is too much fun.” I felt his fingers go deeper in my hole, just a little bit but enough to feel it deep in my guts, “Ungh…fuck…I don’t want to cum before she gets here…ungh, and I’m getting close,” I warned. He handed me the little brown bottle, “Here, these will help.” I didn’t hesitate and took a hit. “Take another hit, a really big one this time, and hold it as long as you can.” I did as he instructed, and the rush was so intense I almost blacked out before exhaling. “Oh fuuuck,” I mumbled. “Better?” “Mmmm, yeah,” I groaned and spread my legs a little wider. “Yeah, that’s it, fucking feels good doesn’t it?” He managed to push his fingers a little deeper. “Ahhh….mmmm, yeah, fuck, so good,” I tossed my head from side to side on the mattress. I can’t believe how good this feels. Then he took it up a notch and was suddenly stroking my dick while fingering my ass. “Ohhh God….yeah, that, that…” was all I could mumble. He chuckled, “Damn Zach, you really like getting your ass played with, huh?” I rubbed my face and mumbled, “I didn’t…ungh, now I do.” He stroked me a little faster and harder, so he was pounding down on my crotch at the same time pushing up on my prostate. “Oh FUCK, Shane…I’m gonna cum if you keep doing that,” I squirmed under him, my legs wrapped around his back. He dropped my dick and slowly pulled his fingers out of my hole. “Damn dude, that was so hot, I can’t get over how tight you are. I’ll bet it would feel so good on my dick.” He started stroking his dick with his right hand again, his left hand lifting my balls and then letting his thumb drop down to my pucker in the gentlest touch. I was completely blown away by the stimulation he had just given me, and yeah, I heard what he said, but it hadn’t yet registered —what he said. As the intensity started to simmer down, my breathing coming back to normal, I could hear the porn again and glanced at the screen. Much like the previous video, the two guys were fucking, this time the first guy was laying like I am with the guy between his legs like Shane is between mine, just railing him, and the rigl is bobbing her head up and down on his cock and the dude looks like his mind is blown…not unlike mine right now. “That looks so hot, doesn’t it?” Shane asked. I reached for my dick which had finally settled down enough that I could start stroking it again without popping off. “Yeah,” I nodded without taking my eyes off the video. Shane chuckled, “Zach, would it be crazy…would you let me try putting my dick in you?” My head snapped back to Shane, trying to focus on his face, expecting him to be joking, “What?” He grinned, “Just the tip, you know, just to feel how tight you are.” My face scrunched up, “I don’t know, man, that’s pretty gay.” “It’s no more gay than what we already did.” He started rubbing his thumb over my lubed hole. “Mmm, yeah, but, it is, it’s not a finger, it’s your dick,” I tried to laugh it off. “Come on, man, I’ve never felt any hole so tight, let me just feel your ring around the head and then I’ll pull out.” “I don’t know man,” I felt that flush come back to my chest, a nervousness mixed with an extreme horniness. “What’s there to think about? I’m not going to tell anyone, and you liked my fingers so much you almost blew your load.” “Just the tip?” He reached for the lube. “Yeah, it won’t be weird, it’ll probably feel really good for both of us.” He squirt some lube on his fingers and rubbed it on my hole, then added more to his dick, quickly shifting a little closer so he had to push his cock down to reach my hole. His left hand on my thigh, his thumb rubbing between my leg and grundle I felt his cock slip down between my ass cheeks, slick as all hell it slid right over my hole and I let out a sigh. He lowered his dick even more, the tip centering on my pucker and he nudged the head in, using gentle rocking until he finally gave it a little extra pressure and my hole stopped resisting his girth and it popped in with a sting. “Ahhh, FUCK, no pull it out!” I growled. The pain shot into my guts like someone fired a gun into my ass. He rubbed my thigh, “Dude, I’m not even in yet, you gotta let me get the head in.” He reached over and grabbed the poppers to hand them to me. “Here, take a hit, it’ll help you relax.” I quickly uncapped the bottle and took a deep hit, then another. The rush was a million times better than the sting of his dick. “Take another hit, a big one on each side, and really hold it.” Shane started adding gentle pressure this time. Shifting his weight for more leverage as I took my hits and held it like he asked. The wave crashed over me and I felt myself start to relax and let his dick push into my hole. This time, without the sting, the head sank into my hole with a smooth warmth and added pressure to my prostate. We both let out an “mmmm” as we held it there. He was restraining from pushing deeper, and I was restraining from pushing him out. “Fuck that feels good. I can feel your hole clamp down on me. Can you feel me in you?” I nodded and groaned, “It’s weird.” “Good weird or bad weird?” “Just…weird,” I felt the poppers hit their peak and my hole relaxed a little more around his cock. “Oh fuck, I can feel your hole trying to suck me in like it did with my fingers.” He had both hands on my upper thighs now, his cock slowly inching it’s way a little deeper. “Holy shit Zach, it’s so warm, like a silk pillow wrapped tightly around my tip…I’m gonna push a little deeper, see if you can handle more of me.” “Ungh, wait,” I groaned, but didn’t really put up a fight as he sank two more inches into me. “Ahhh…fuck, ok, that’s enough,” I groaned when he got a little too deep and I felt a pang. He stopped pushing and grabbed the poppers, taking a deep hit. “Fuck dude, you’re so tight I almost nut when you clamped down just now,” he chuckled as he exhaled. “Dude, what? You better not cum in me,” I clamped down instinctively and he gripped my thighs tight with his hands. “Oooh, shit, dude, if you don’t want me to nut right now you need to relax,” he whispered as if the vibration of sound would set him off. “Shane, no, you need to pull out,” I insisted. “Can’t, you’re clamped so tight, if I move I’m gonna blow,” he whispered again. I grabbed the poppers from him and took a deep hit, then another. As the rush hit me, I took another deep hit and another for good measure, feeling my body completely relax to the point where my dick started going soft. Shane noticed and started stroking my dick for me as the poppers did their thing. “Shit….ok, I can feel you relaxing,” Shane said and slowly pushed deeper into me. “Ahhh, fuck, Shane, you’re pushing in, you need to pull out,” I groaned feeling him hit deep in my guts and the feeling was a new height of pleasure that almost made me blow my load. “Does it feel good?” “Mmm…yeah, but I don’t want you to cum in me…and I don’t want to cum before Veronica gets here,” I mumbled and clenched on his dick again. “Oh fuck, dude, that feels so good, you feel so good, I don’t want to pull out yet. Can’t we just do this until she gets here?” “I don’t know, ungh,” he rocked his hips a hair, “Are you….do you just want to hold it there?” He pulsed his dick inside me, “I can hold it, or I can give you a few pumps,” he rocked his hips out a tiny bit and then back in. “Ungh…fuck” I groaned. “It feels good, right?” “Mmmm, yeah but…” “So let me get a few pumps in, just until Veronica gets here,” he insisted. “Is she going to be here soon?” “She’ll be here any minute, I think,” he rocked his hips again, the pain gone and nothing but pleasure this time. “Fuck…ok, but…mmm, ok, we should use a condom though,” I moaned. “Why? You can’t get pregnant?” “Yeah, but…” “I’m not going to cum in you, I’m saving it for her,” he rocked his hips in a slightly bigger stroke. “Ungh, ok, just a few minutes until she gets here,” I caved, grabbing my dick. He leaned over me and started to slowly pump his hips in and out, his dick sliding in deeper and then back out until it almost popped out, then he’d pump all seven inches back into me and grind on my ass. “Your ass feels so good, I love how tight you are,” he mumbled between thrusts. I kept stroking my dick, but as I felt myself getting close I’d stop stroking, even though he kept pumping into me. After only a couple of minutes, it was feeling so good that stopping jerking wasn’t going to do it, so I grabbed the poppers and took a deep hit, then another. Shane smiled at me as my rush peaked and he thrust a little harder into me, his cock hitting even deeper inside me. His face looked like he was in pure bliss, and I was getting nervous. I offered him the poppers, and he nodded yes. Taking a good hit on both sides, but he kept slowly pushing in and grinding as he did. “Oh man, Zach, this is the best ass I’ve ever had, I don’t know how much longer I can hold out.” “Dude, you need to hold out. Veronica will be here soon,” I groaned, feeling him hitting deep with every pump. “I can nut twice, I need to nut,” he said, thrusting harder and faster, his hips slamming into my ass for a few strokes and then he slammed hard into me and I felt his dick throb, “Ungh,” he slammed into me again, and his cock slid with no friction, so smooth it felt so good and wet. “Mmmm.” he moaned quietly as he stopped moving inside me. “Fuck, did you just cum inside me?” I asked, feeling his dick still twitching inside me. “Oh yeah, fuck, Zach, you’re hole is so tight, I couldn’t hold it,” He chuckled, still holding himself over me he slowly sat up straight and put his hands on my thighs as he caught his breath. “Dude, I told you not to cum in me,” I was having mixed feelings, it felt so good, but I was also angry. “Sorry dude, it just happened, I couldn’t help it,” he slowly started to pull out, and my hole suddenly felt empty. “What about Veronica?” I asked. He grabbed his phone, “Oh shit, she text.” He started texting her back. I started stroking my dick, “Is she almost here?” “Damn dude, I had a lot of lube on my fingers, I think I turned the ringer on and then back off by accident.” “Ok, is she here?” He sent a text, “I think she got here but forgot which apartment I’m in and then left when I didn’t respond to her half dozen messages and two phone calls.” He looked over at me with a guilty look on his face. “Are you serious?” I felt my blood boiling. “Yeah dude, look,” he showed me her response to his most recent message, saying, “I left,” time-stamped 12:04 a.m. Now it’s 12:05 am. I couldn’t think straight, “Fuck, I can’t believe…..FUCK,” I felt dirty and used, as I rolled off the bed and yanked my clothes back on. “Sorry, man, it was an accident,” Shane was trying to calm me down, but I wouldn’t hear it. I just kept grumbling about how this is bull shit, gathered my things and stormed out. The next day, after classes, I had a shift at the coffee shop with Anya. “You look like shit,” she said. “I had a late night,” I said, grabbing a mug and pouring myself some coffee. “How was spring break?” She asked. “It was ok, I guess, how was yours?” “Ugh, it was ok, I ended up going home…” “Because you broke up with Shane?” I was about to launch into how ‘he’s an asshole’ but then she corrected me. “Well, yeah, but he called me up a few days ago and apologized, so we’re good now,” she then launched into a long story about something that happened to her at home. All I could think was how Shane lied to me about being broken up, fucked me, nut in me, and…what else was he lying about?