Dillon - Haloween - Alessandro

I’m one of the guys who always knew he was straight—never questioned my sexuality—never cared about other people’s sexuality. I was also pretty progressive on the subject compared to other guys my age, and for the early 2000s in Kansas. I was one of those guys who told his friends to stop using the phrase “that’s gay” to describe something that wasn’t cool. I also played a fair amount of ‘gay chicken’ over the last couple of years with my friends, and never got turned on, so I feel like that would’ve been it if there was a switch to flip, right? I can’t take all the credit; my parents are pretty progressive. My mom is a lawyer for the ACLU, so there was always talk in our house about how “words matter.” 

I graduated in 2002 and began school at UCLA in the fall. It was your typical freshman experience. I rushed a fraternity and was accepted. In my sophomore year, in 2003, I was able to convince one of my fraternity buddies, Alessandro, from my pledge class to be my roommate, allowing us to enjoy Greek life while still living in a somewhat clean dorm room.

Alessandro was great. We had become close friends while rushing last year. We had a lot in common, and he was one of the few pledges that seemed to have half a brain, so we got along well. He is a third-generation Hispanic American and the first in his family to attend college. So, he understands the pressure and balance of needing to be on top of his studies, while also living life while he is here. He’s not just smart; he’s also good-looking. He’s 5’10”, naturally tan, perfect teeth, thick dark hair, he’s got one of those sleeper builds where you’d look at him fully dressed and think he’s just another skinny guy, like me, but then he takes off his shirt and bam…cut city. He also has great style, which has been an asset to me because we can wear a lot of each other's clothes, and his are way cooler than mine. I think it’s his charisma at the end of the day that is his biggest asset to both of us; it makes it easy for him to pull so many sorority chicks, and he’s an even better wingman.

I’m not too shabby myself. I’m 5’7”, pretty lean at 130 lbs since I did four years of tennis in high school, and it forced me to be lean, flexible, and with excellent reflexes. I have very fine, light sandy brown hair, almost blonde, hazel-gold eyes, and an Irish-German heritage that makes me pigmentally challenged. My smile is as straight as Aley’s, but I don’t show it as easily as he does, out of habit, as I'm still cautious about smiling big after having had braces—the irony. I do alright with the ladies, but I’m not as charismatic as Alessandro is; he’s way more suave, but his personality is intoxicating and pulls me out there with him. I’m more of the plucky comic relief and get the pull the girls that didn’t make it onto his dick that night. Aley says I have “Ugly Duckling Syndrome,” constantly telling me I ‘need to recognize how attractive I am’…But I think he’s just gaslighting me, usually to convince me to do something I don’t want to do. It also works more often than not, so I don’t know if that makes me a sucker or if he has a charm factor of +10.

I never questioned Alessandro’s sexuality any more than I questioned my own. There was a brief moment when we had the conversation about rooming together this year, when he said he’d only do it if we implemented an “Opendoor Policy” so we didn’t have to hide our masturbation habits. I thought it was a weird thing, but when he explained, his current roommate insisted on it, and it made their lives ‘so much better,’ I figured if it got weird, I could just leave the room. Instead, it made us better friends pretty quickly. I also learned that he had a slightly bigger dick than mine. I’m 5.5” circumcised, so he’s easily 6.5” uncircumcised and a decent amount thicker than I am. I’m what you would call a “grower, not a shower,” and in the first week, I realized he was mostly the opposite. The first time we jerked it in front of each other was after the first party back from the summer break at the frat house, and we were drunk, horny, and he said he had to get off before bed. I was pretty wasted, but curious to see how this would work. I wasn’t grossed out by the idea of seeing him jerk off, or even being in the room while he’s doing it. I guess it was just my shyness holding me back from partaking at first. But as soon as he stripped down, tucking his Carolina Blue CK trunks under his balls, I couldn’t take my eyes off the sight. It was…fascinating. 

I felt almost like Jane Goodall, watching the subject pleasure himself. He could tell I was into it and suggested I join him in several different ways. Most of them didn’t work on me, but the one that did work was when he called me out for having a small penis and being afraid to show it. What was I to do? I had to prove I wasn’t a tiny dicked dude. I whipped my shorts and briefs down to my ankles in a dramatic show. My dick was already hard, and I let it dangle out there for him to take in. I’m not shy about my dick, or my body, and I tend to be a showoff when I’ve had a few drinks in me, but in this case, the one-on-one sexual-adjacent situation, I’ll admit I was feeling a little shy. It did break the ice, though, and we almost silently watched each other stroke ourselves off from our separate beds. The excitement of it all was a bit overwhelming, and I shot first, which seemed to trigger him, and I missed him shooting his load because I was coating myself, and my eyes were closed. 

That night definitely tore down some boundaries that I didn’t know I had, and opened the door for some fun conversations over the next few weeks about porn, pleasure zones, things we’ve tried with partners, and things we’ve tried alone. For the most part, we had a lot in common when it came to ‘fetishes,’ using that term loosely because we are both pretty vanilla, and we have about the same amount of experience. The big difference is that he’s had many more partners, and I’ve had more repeat partners than he has. He’s also tried butt stuff, and I’ve never indulged, though the way he describes it does sound hot, even if a little gay to have it done to you instead of to her. We started sharing porn links on the regular, would rub one out, and go to sleep if we were both in the room getting ready for bed at the same time, and it became a twice-a-week thing once our schedules normaled off. 

“Dillon,” Aley looked up from his laptop, grabbing my attention. “I just read the e-mail about the Halloween party at the house. Have you read it?”

“Nope,” I said, not looking up from my laptop.

“Sounds like it’s going to be wild. Have you figured out your costume yet?” Alessandro asked.

I looked up from my laptop, “I was probably going to do Marty McFly or something easy.”

He rolled his eyes dramatically, “Dude, no. You have to dress up. You know putting a vest over your all-denim, midwestern, everyday clothing is going to get you razzed by the guys pretty hard. You remember what happened last year when David tried to put on a pair of red swim trunks and said he was David Hasselhoff?”

I chuckled, “Yeah, they made him strip to his underwear and wear the Sash-of-Shame all night.”

He nodded his head, “Do you want to wear the Sash-of-Shame in your tighty whities in front of all those hot bitches all night?”

The dig at my underwear of choice would’ve annoyed me, but he knows I have been wearing briefs for years because it was part of my uniform to play tennis back in high school. Yes, I could’ve done like the other guys, and wear boxers when not playing, but honestly…I was more comfortable wearing briefs, and I like the way I look in them. Besides, I know he is a fashion guy and switches it up based on what he’s wearing to whatever he is dragging me to, so he has a broader array of underwear than I do. I know it’s all in jest, and I sigh at the comment dramatically. Still, he has a point. I don’t want to be wearing the Sash-of-Shame, even if I look good in my briefs, and by the way, have had no complaints my entire sexually active life from the women who I’ve hooked up with. I closed my laptop. “Why do I feel like you’re setting me up for something?”

His lips curled in one corner, forming a crooked smile that I’ve learned is a tell he has. “Well, I was thinking, since you love that farmer look, and denim so much, and to keep it simple, cheap, but fun, AND to make sure neither of us ends up with the Sash-of-Shame for not ‘going the distance’,” he spun his laptop toward me. “How about we go as Paris and Nicole from The Simple Life?”

I cocked my head to the side and chuckled, “You know I hate that show.”

He laughed, “Come on, it’ll be so easy, and inexpensive. Plus, we’ll get to pop into girls' conversations and pretend to be ditsy women, they will laugh and appreciate our genderbender costumes…then ride our dicks all night.” He humped the air pretending to fuck someone.

I was starting to see his vision, “I mean…I do have the legs for a mini-dress,” I joked.

“Bro, I’ve seen you naked, you don’t even need to shave those hairless legs. Besides, how long has it been since you last got laid?” He asked.

“Ugh…the first party back at the beginning of the semester,” I groaned.

He chuckled, “Bro, you jerked it with me that night, remember?”

I blushed, “Oh yeah. Shit, I guess the week before coming back to school then.”

“Too long, that’s the answer, way too long.” He pulled up another picture on his laptop. “Look, we can go to the second-hand store off campus, get the entire costume for like twenty bucks, then all we need is a couple of blonde wigs, which we can get cheap from the costume store.”

I chuckled, “And…dressing as blonde women will get us laid?”

“It won’t hurt our chances. Plus, you have the booty for a mini skirt,” he joked.

I rolled my eyes, then rolled onto my side, and gave myself a spank. “It is pretty toned.” I laughed.

He jumped on me and started play-wrestling. “That’s my boy! Let’s go shopping after class tomorrow,” he said.

I laughed as he started humping into me and squeezing me tight. “Alright, alright, you win!” I shouted, and he got off me. “Oooh, shit, I have a study session tomorrow,” I shrugged.

He squinted his eyes in distrust, “Is there a potential to get laid?”

I felt myself blush, “There is a small chance.”

He grinned, “Alright, alright, I’ll support it, but I can’t go Thursday, and Friday night, we’re expected to help decorate at the house,” he crossed his arms.

“Damn, can you go without me? Pick me up something slutty? We both know you’re going to pick out my outfit anyway.”

“Damn, Paris, you’re already trying to treat me like Christina,” he joked.

I laughed, then did my best Paris Hilton voice, “Thanks, girl, you’re literally the best.”

When I got back from my study session, Aley was already back in the dorm doing his homework at the desk. “Yo, yo,” I called out.

He pulled off his headphones. “Bro, you’re back early.”

I grinned, “Were you about to watch porn without me?”

He chuckled, “No, I popped one off when I got back an hour ago. The tissues are still wet if you want proof,” He pointed toward the trash can, which had wadded up tissues on top. I couldn’t help but chuckle, seeing the wet tissues in the can.. He shrugged his shoulders, “I was hoping you’d be out all night piping that nerdy girl in your study group and wouldn’t have it in you to jerk off tonight.”

“Oh, yeah, she didn’t even show up. It was me, the fat girl, and two dudes who definitely need a shower.” I shrugged, putting my backpack down by my bed. I noticed a plastic bag on my bed. “What’s this?”

“Oh, I got the perfect options to try on. They both fit me well enough, so you try them on and whichever you don’t wear, I’ll wear,” he said, smiling like a kid on Christmas morning.

I opened the bag, pulling out a pair of overalls, a white t-shirt, a red bra, and a denim skirt. I couldn’t help but laugh, immediately pulling off my shirt and trying on the bra, “Oh my God, how do you put it on? I’ve only ever taken them off,” I laughed.

He jumped up from his chair, helping me hook it in the back. Then I dropped my jeans, laughing at the look in the mirror of my skinny body in a bright red bra and white Abercrombie & Fitch briefs. I tried to pull the overalls on, but they fit pretty awkwardly on me, though I could see the costume coming together. Then I tried on the denim skirt, and I looked decent in the skirt.

Aley did a cat-call whistle, then did his best construction worker impression: “Shake it, baby!”

I laughed and tried my best to walk like a girl, strutting down the five feet of space in our room before you hit the door, did a spin, and walked back. Both of us laughing at this point. “I think the skirt will work,” I said, reaching for the shirt.

“Oh, it’s working,” he said, and I couldn’t help but notice he adjusted himself in his shorts. I’m sure it was nothing, just odd timing.

We went to the party on Saturday. I wore the denim skirt, white noodle strap top with a red bra underneath, Aley suggested I wear a pair of his white bikini briefs instead of my usual underwear. He was right, they looked better under the skirt. Aley had one of the girls going to the party tonight help us with our wigs and makeup before we left to help finish setting up.

On the walk over to the house, Alessandro joked about how I didn’t even need to shave my legs because the hair was so light you couldn’t see it. He ended up wearing the denim overalls, even though they didn’t fit him any better than they fit me. He let the straps out as far as he could, but they still kept riding up into his crotch, and he kept pulling at them, making me laugh each time. He did a white bra only underneath, along with the wig, both popping against his skin tone, and I’ll admit he looked kind of pretty. 

With the cheesy accents and overusing the word “hot” all night, people really got a kick out of our costumes. We even came close to winning the competition. We still lost, but it was fun.

I really had fun being Paris, though it didn’t get me the attention from women that Alessandro had promised we’d get. I got a shocking amount of ass grabbing from the guys throughout the night, though. At first, it was funny, then it was annoying. At some point, probably too many drinks in, it started becoming funny again, and I was playing into it. 

Tank, one of the brothers who lives in the house, is more wasted than I am and actually mistook me for a sorority chick from behind. When he snuck up from behind, wearing only his Tarzan costume, he wrapped his muscled arms around my thin waist and pressed his bulge into my ass. I thought he was just joking around, so I played into it, rubbing my ass back against it until he whispered into my ear, “That feels good. Why don’t we go up to my room and have some fun?”

I didn’t know what to say, and I could feel his bulge growing against my denim skirt-covered ass. If I were sober, I would’ve probably been grossed out, or at the very least laughed it off, but I froze. Having had my ass grabbed all night, this was different, almost sensual. As his hand traveled down my hip and up my skirt, I felt a tingle that really confused me and started sending blood down to my crotch. He pulled me tighter, his obviously thickening dick strapped down by the jock under his loincloth was wedged between my ass cheeks, a feeling I’ve never felt before as pressure was put on my hole through several levels of fabric, and it felt…good. When his hand made its way between my thighs and traveled further up, it cupped my balls instead of a girl's pussy. He realized his mistake and shoved me away from him. We made eye contact, and he flushed red. “Bro, I got you,” he said, trying to cover up for the fact that he just legit felt me up thinking I was a girl. Both of us knew he was getting turned on, rubbing his bulge against my ass.

I laughed, “Yeah, I wasn’t sure what you were doing,” I let him off the hook and continued walking away. There was a lingering, tingling feeling that wouldn’t go away, though. Something about the way his strong hands caressed my legs, it’s not something women do to men, and his hands were so…I don’t know, on a mission…to feel me up. It made me feel sexy in a way I hadn’t felt before. I know I’m an attractive guy, and women come on to me, but this was…like a superpower I just discovered I had. Being able to turn on guys is kinda…fun? Hot? Definitely exciting in a weird way. I tried to shake it off and enjoy the rest of the party. For the most part, I was successful. With enough alcohol and weed, you can accomplish anything.

Alessandro’s plan to infiltrate the women’s circles backfired spectacularly, and we went back to the dorm drunk as hell. The walk back was about twenty minutes and filled with drunk karaoke and some skipping once we took the heels off.

Back in the dorm, Alessandro immediately strips off the overalls and bra, leaving himself in a pair of grey sport briefs, and I couldn’t help but notice his bulge was half chubbed. He saw me notice him and gave himself a squeeze as he sat on his bed.

“Do we have any more of that vodka and orange juice?” He asked, leaning back on his elbows, his pecs popping as he held himself up.

I went over to the mini fridge and bent over to get the carton of OJ that we had mixed vodka into last weekend. As soon as I bent over, Alessandro whistled like a construction worker again. I laughed, knowing my ass was on display. I can’t figure out how women manage to wear these things and not have their underwear out all day. I straightened up, doing my best porn voice and sticking my chest out, I said, “Do you want this in a glass, or do you want me to…put it in your mouth?”

He chuckled, then pointed, “That cup only had water in it, pour some in there.”

I poured some into the cup, then a little more, and a little more. Then I took a big swig from the cup as I did my best sexy walk over toward him. “Open up, big boy,” I said, holding the cup over his head. He tilted his head back, and I slowly poured some into his mouth until it was full enough that he had to swallow. He gulped it down and laughed. I took another sip and noticed he again grabbed his crotch; this time, his hand lingered on his bulge. 

I know I’ve seen him jerk off several times before, I’ve seen him naked more times than I can remember, but something about this chubbing of his dick felt personal. Like…it was for me. I had to say something. “Looks like you’re a little happy to see me,” I took a swig from the cup and passed it to him.

He huffed, cupping his package, “I can’t help it. I keep seeing Paris and,” he shook his half-hard package, “you know I have a fetish for blondes,” he shrugged.

I felt a little deflated by that, almost like I was rejected somehow because he was into Paris, and it wasn’t for me. I spun away from him, flipping my blonde wig.

He chuckled, “You joke, but from behind, you look like the real deal.”

I spun back around, walking toward him. I leaned over, putting a hand on his shoulder for support as I grabbed the cup from him with my other hand. “And from the front?” He chuckled, grabbing his crotch again, giving it a gentle squeeze that didn’t go unnoticed by me. I had to call him out on it, “Oh…is that for me, or for Paris?” I stood back up to sip the drink, suddenly activating a new round of ‘gay chicken’ but at a collegic level.

He sat forward, one hand still on his bulge, the other running up my thigh, gently cupping my ass when it got to the top of my leg. “There’s no way to know,” he jokes. In the rules of ‘gay chickn’ this would usually prompt me to either double-down or back out. Then his hand cups my ass cheek, his long fingers grazing my asshole through the fabric of my…uh…his underwear, and it sends tingles into my body. 

I’ve never been touched there. I wash thoroughly, but it’s quick and not sexual. This touching…this was igniting a fire inside me, and I was very much letting my body run toward this new pleasure. 

I tried to keep up with the game as I ran my hand down his arm, causing him to squeeze my cheek tighter, then my hand ran over his shoulder, up his neck, cupping his cheek. “Well…do you need to take care of it?” I used that specific phrase becasue he’s used it in the past to suggest we jerk off together several times over the last few weeks.

He looked up at me, that corner of his mouth pulling a grin on his face, his glassy eyes smiling even bigger, “I really do.” He let his hand slide down the back of my thigh and back up to my ass cheek for another squeeze, “I would really love a lap dance,” he took it to another level.

I don’t know why, but I was fighting an erection of my own. I sipped the drink, handed it to him, and broke away from his hand. I felt like we were mostly joking around, guys being guys, and since I know we are going to jerk off tonight, I figured I’d just keep pushing the joke a little further, to see who wins. I turned on the radio on my desk, and the song “Baby One More Time,” by Britney Spears, was half over. I turned it up; the music video burned into my memory. I spun toward him, doing my best Britney dance, and was probably murdering it, but I felt like I was pulling it off.

I closed the distance between us, turning around and bending over quickly to flash my brief-covered ass in his face, earning me a chuckle from him. Then popped back up, swinging my hips to the beat. He played along, both of his hands sliding up my legs and under my skirt, cupping my ass. I heard him chuckle and say, “fuck yeah,” which only egged me on. I spun back toward him, grabbing him by the head I pulled him into my skirt, his face mashing into my crotch, both of us laughing. Then I shoved him backward onto the bed, and he fell flat for a second before pushing himself back up on his elbows. Every muscle in his torso flexed as he put his legs together, then pushed his feet between my legs and extended his. Hooking his legs behind my knees, he pulled me forward, and I straddled his thighs. He pulled me further up onto his crotch. I could feel his bulge between my cheeks, the thin fabric of our underwear the only thing preventing the skin of his dick from touching the skin of my ass.

He held my hips tight and I lifted my arms above my head, swinging my hair back and forth, opposite of my hips as I grind on him, doing what I imagine a lap dance consists of. Having never had one before, it was a best guess, but he let out a quiet, “Oh yeah,” and gripped my hips tighter, encouraging me to continue. I thought it was hilarious but also horny at the same time, so I continued, realizing he was getting hard under me. I felt a rush of excitement, my heart suddenly beating faster than the music. Britney shouted, “Hit me baby one more time,” and the song ended, rolling right into Christina Aguilera’s “Genie in a Bottle.” Another music video burned into my memory.

I should’ve ended the act right there, but his hands clamped on my hips, he started grinding his crotch up into my ass, it felt…surprisingly good, I could tell he didn’t want me to stop, so I started a slower, more purposeful grinding on his almost fully erect dick underneath me, the beat of the song setting my rhythm. I kept running my hands over my body as “Genie in a Bottle” as I could. I felt an incredible rush when I felt his dick flex as I ground down on him. He felt something, too, and a grunt of air came out of him as he pulled my hips down tighter on him. The radio DJ shouted something at us, and suddenly I was grinding on Alessandro to the beat of “Get Low,” by Lil Jon, and Aley was grinding right back into me.

Aley released my hips and let his hands travel down my thighs, gripping my quads, letting his thumbs dig between the muscle as he traveled back up and under my skirt this time. It felt amazing, and I grind even harder on him. There was no denying he was hard now, and if his hands continued traveling up, he’d soon realize I’m just as hard. I circled my hips on him, both of us chanting, “To the WINDOOOW!” Then got right back to our hips gyrating in tune to the beat, neither of us following up with the mention of balls, probably not wanting to remind the other that we were grinding on male anatomy.

The radio transitioned into “Peaches & Cream,” and I felt his dick throb under me with a not-so-subtle groan as I instinctively clamped my ass cheeks around the sausage. His hands slid further up my skirt, his thumbs started massaging my thigh and balls, the pad of his thumb barely grazing the wall of my sack just under the elastic of the skimpy underwear. It felt so good, I let out a soft moan and rocked my hips the opposite way from the direction we had been grinding on each other. This set off a chain reaction of his cock grinding hard in the opposite direction, flopping against my ass cheek when I slid back onto him, and he moaned as his hands squeezed on my thighs, and it made me moan.

That seemed to flip a switch inside him, and things escalated quickly. He thrust his hips up, almost bucking me off, hooking his thumbs into his own briefs and shoving them halfway down his thighs, one less layer of fabric between us as I landed right back down on his dick. Feeling my head spinning, when “Hot in Here” by Nelly dropped on the radio, my hands went above my head, and my grinding became more exaggerated. Aley’s hands went back up my skirt, his fingers hooking into the waistband of my bikini briefs. He pulled them down hard as far as they would go down my thighs, stretching them about midway down, my cock sprang free and tented the denim skirt. My bare ass landed right on his hot cock. He thrust and poked right at my balls, sitting on his pubes. “Oh fuck,” I moaned. The feeling was incredible.

I started gyrating on his dick, the feeling of that warm rod resting long way across my hole was a soft intensity that I wasn’t prepared for, and neither was he. Both of us grunted, trying to hide our pleasure, but neither of us slowed our grinding. His hands slid up my bare thighs, and I thought they would stop before touching my groin, but his thumbs wrapped under my balls, sending lightning bolts of pleasure into my body as his dick slid across my hole again. The familiar beat of Alice Deejay’s “Better Off Alone” started playing on the radio. I leaned back slowly, holding myself up by my hands as I continued circling my hips on his dick. His thumbs were massaging the space between my balls and asshole, and I was leaking precum into the denim skirt. Each thrust of his dick dribbled what had to be his precum across my asshole, and it was all so much, but I wasn’t going to stop if he didn’t stop.

The song transitioned smoothly into “Waiting for Tonight” by Jennifer Lopez, a song I know he loves, and he grind harder into me. “Ungh,” I heard myself moan, still looking up at the blury ceiling I felt one of his hands leave my crotch only to return a second later. It was wet with saliva, slipping between us I raised up a little to let him do what I think he’s doing, biting my upper lip I felt a wet finger slide right over my tight brown pucker. “Oh…mmmm,” I grind down on him. His other hand reached for my dick and started stroking me. The two pleasure points converged somewhere inside me, and the rush of blood flowing through my body was so intense I felt my body quake with pleasure, my legs tightened around his body, and I felt my hole open just enough for him to slide one of his fingers into me. “Oh fuck,” my head lurched forward and then dropped back as I started riding his finger deeper into me.

He seemed to know exactly what to do with my body—stroking my dick and twisting his finger to perfectly hit my prostate as my hips were gently rocking on his fist. Having never touched myself there for pleasure before, the feeling was incredible. I know I should’ve stopped at declared him the winner, but fuck it felt good. I was having an out of body experience and the only thing keeping me from floating away completely was his finger inside me.

The radio switched over to “Jumpin’ Jumpin’” by Destiny’s Child, and he pulled his finger out of me as we both switched up our grinding to get more of his dick sliding over my hole. He spit on his hand and smeared it on his dick, then spit again and slid two fingers into my hole. I trembled on top of him, his two fingers were pressing inside me and seemed to be firing off mini orgasms with every twist. I felt the precum drool from my cock onto the inside of the skirt. “Oh Jesus,” I moaned. I hadn’t even touched my dick yet, but I could feel myself desperate to blow my load.

I rocked on his fingers, feeling my hole pulsing around his knuckles as he dug deeper into me and stroked my dick painfully slow. When the radio switched over to “South Side” by Moby, I was already in a trance, but he pulled out his fingers and added more spit to his dick, this time rubbing his slick cock head right over my hole. I don’t know what came over me, but I leaned back further, lifting my ass to let him do it. The slick soft tip felt way better than his rigid fingers on my sensitive skin. His free hand came back with even more saliva and smeared it right on my pucker. Feeling outrageously good, he got bold and pressed the head of his cock on my hole. I rolled my head as my hips rolled on his dick, just to tease him a little, but then he rocked his hips up and forced the tight pucker of my hole to open and let him into me.

“Oh fuck,” I groaned. It was an intense mix of pain and pleasure. I felt my heart start pounding out of my chest, the sting of his…of Alessandro’s cock popped into my ass and an something inside me felt like it had been ripped open at the exact same time the slickness of his wet tip swas putting pressure on my prostate, it felt so good my body was fighting the pain and pulsing around his tip to get more of that pleasure.

Neither of us said anything, but the grunts from every little movement could be heard as the music died out. A very manly DJ voice said, “We’re going to toss it way back with this one.” A synth rhythm started playing to the beat of my heart, a woman started singing, “I'm in the dark, I'd like to read his mind…But I'm frightened of the things I might find…Oh, there must be something he's thinking of…To tear him away, eh-aye,” and I felt my hole relax enough to let another inch of his dick inside me. Aley let out a grunt of pleasure, and I felt his dick twitch inside me. Both of his hands were rubbing up and down my thighs now, begging me to relent and let him in. My head was spinning, the urge to get off physically was fighting the desire to get off sexually, and when his right hand made its way up to my cock to stroke me back to life, the rush of pleasure won the battle, and I moaned. 

“Hush hush, keep it down now,” the lady on the radio sang. “Voices carry…”

Aley rocked his hips up and forced two more inches into me. The friction of his cock on my anal walls was intense, but the other pleasures…”Oh God,” I moaned, the pleasure of being stretched by a slick cock, I leaned back onto my elbows, and my legs butterflyed out as my ass sank further down his sock until I felt the bristle of his pubes on my hole. “Oh shit,” he whispered, stroking my now hard dick a little faster. I tried not to open my eyes, the music thumping in my ears, I did the same movement with my ass muscles that I would when fucking a woman to fuck my dick up into Aley’s hand. I don’t know what felt better, his hand on my dick or the pressure inside me from his dick. As if he was reading my mind, he gave me a gentle thrust, the rush of pleasure bursting into my body like a tidal wave answered my question. “Ungh…fuck,” I wimpered, my brain disconnected from my body, I didn’t know how to move anymore, I just rocked with him. Ignoring the burning in my arm muscles trying to hold me up because the pleasure in my ass and on my dick was so good it was worth it.

The radio switched over to “Hangin by a Moment” by Lifehouse, and I know Aley hates this song; suddenly, reality came back into my body. The realization that Aley has his dick buried in my ass, fuck, that I’m riding his cock, hit me, and I clenched. “This is so wrong,” I whispered.

“But so good,” he fired back. He was right, and a big part of me was glad to hear him say that as his hands ran up my thighs, up my skirt, and back to my dick, “just relax,” he said in a tone that let me know he wanted this, that I hadn’t taken advantage of him.

I leaned forward, completely impaling myself on his cock, it was deep in my guts, and it was weird. Even weirder when I looked down to see my naked friend looking up at me, his hands under my skirt, pumping my dick, and the denim popping up and down from it. He smiled, his eyes glazed over. “We should stop,” I whispered.

“No, don’t stop,” he pumped his legs, his dick getting an inch into me and then back out a few times. His eyes rolling back into his head.

“Ungh…should we get a condom?” I asked.

“No, just relax,” he mumbled, pumping faster into me as he stroked my dick.

The thrusting was getting more intense. I found myself rocking my hips with his, his cock getting deeper inside me; each slow pump was a little easier than the last. I rocked my hips in a slightly wider birth, but planted my ass hard on his crotch, maximizing my pleasure. I felt a tremble in my body. “Oh fuck,” I mumbled, rocking faster. I took control of my dick; his hands went right to my hips. “Oh fuck,” I panted, feeling something igniting inside me, an intense pleasure that I couldn’t get enough of. I put my free hand on his flexing pecs, squeezing my ass around his cock, my hole gripping him as he pulled back and pushed back in. “Oh shit,” I trembled.

“Feel good?” he whispered, changing the way his thrusting was hitting me, digging deep with each pump.

“So good,” I squeezed his pec, feeling my balls rubbing on his pubes as his sex muscles tightened and relaxed under me. I felt his dick swelling inside me, the added pressure pushed me over the edge. “Oh…ungh,” My balls instantly tightened, and my ass clamped hard around his base. He kept thrusting into me, and my orgasm exploded from his cock pushing into me. I pumped my hot cum into the denim skirt, rocking my hips on his cock. The intensity of my orgasm was overwhelming, and I moaned like a bitch, “Ungh…”

He held my hips tight, thrusting ten quick, deep thrusts, and then his entire torso tightened, his shoulders and head lifting off the bed as I felt his cock pulsing inside me, a wet warmth washing over the raw, burning flesh deep inside me. “Oh…shit,” he trembled, his face contorting like he was having a stroke as his hands gripped my hips tighter as I rode out my orgasm on his cock and finally relaxed sliding down his shaft as I stopped pumping cum. He kept thrusting up into me, the intensity was too much, but I could tell he was about to cum and I didn’t know what to do, I didn’t want him to cum inside me but then the throbbing inside me started as he pumped a few more times. The last few pumps were slick and he slid effortlessly inside me. I was spent. His torso relaxed and let him rest flat on the mattress with a heavy breath.

My heart was pounding in my chest. The room was spinning as my body tried to normalize, my breathing slowing. I felt so relaxed, but also keenly aware that the warmth under me was Alessandro, and the warmth inside me had to be his semen. I breathed out a few more heavy breaths before I leaned forward enough to let his dick fall out of me. Leaving me with an emptiness I never felt before. He groaned as I lifted off of him and rolled onto my back. I could feel my cum on the skirt, smearing all over my crotch. “Fuck,” I huffed out of breath.

Aley chuckled, pat my thigh, and drunkenly said, “Thanks, man,” as he pulled up his briefs, tucking away his cummy cock. “I need a shower,” he said, standing up a little wobbly.

“Me too,” I said, lifting my ass, I pulled up the white briefs, my cum smearing all over them. I got up, my legs felt like I had just done a hundred flights of stairs, barely holding me up as I learned how to walk again. I pulled the shirt off and then asked, “Can you undo my bra?” He chuckled, shaking his head, and with one hand unclasped it for me, popping it open. I undid the skirt and let it fall to the floor, my dick still chubbed in the briefs. I grabbed my towel and shower gear, slipped on my flip flops, and started heading for the door. “You coming?”

He grinned, “I already did,” and he grabbed his towel.

I shook my head at his joke, and we walked down the hall to the showers.

We showered in relative silence. I kept glancing over at him, trying to process what we just did—questioning my sexuality for the first time. Trying not to be grossed out by the fact that Alessandro’s cum was deep in my guts, but every time I passed the bar of soap over my hole, my hole would twitch instinctively, and I knew this wouldn’t be the last time this happened. Especially since I kept catching Aley glancing over at me when my ass was to him.

As I started drifting off to sleep, I wondered what it would feel like to fuck Aley. Would I have to wait until next Halloween to try it? I blinked my eyes and woke up to the sound of Alessandro vomiting in the trash can. “Ngh…you ok?” I asked, rubbing my eyes, feeling the room still spinning. The darkness letting me know it was still super early.

He puked again, “Yeah, I think I partied too hard,” he chuckled.

I reached between my legs, I realized I was naked and even though the room was still spinning I realized what we had done and felt a little sick myself.

Sometime around noon when we finally got up for the day. I asked, “You ok?”

“Yeah, fuck, I had way too much,” he groaned, holding his head as he stared at his eggs at the breakfast table in the cafeteria.

“I mean, are we cool?” I asked, feeling uneasy about what we did last night.

He didn’t look up and just mumbled, “yeah, why, did I say something stupid last night?” Then he chuckled, “I think I blacked out. I don’t even remember getting home,” he rubbed his face.

I felt my stomach flip. “Oh, me too,” I lied and stuffed my face with waffles. Trying to settle my stomach. I don’t know which was worse, the alcohol turning my stomach into poison, or knowing Alessandro’s cum was probably still in my guts. Squirting the creamer into my coffee definitely made my asshole clench.