Damien - Allie and Drew's Wedding

I went through phases of being bi and even times I leaned towards gay during my freshman year of college. In my sophomore year, I met a girl and ended up getting her pregnant. We were very much in love and I did my best to stay the course, I have always been a committed guy, never cheated, never strayed in any way. Yes, I sometimes missed the sex with guys, but I told myself for the longest time that I was just a horny fucker, wanting to catch my nut any way I could get, and if I focused on my baby mama I would stay straight.

Now I’m 26, with a 6-year-old daughter, her mom left us and we are living with my parents who offered to help me in this single-dad phase of my life. 

My career is doing well, I was able to get in on the ground floor of a startup as a coding engineer, engineering the backend of their platform. It really took off about 18 months after I got in and now I’m not struggling for cash, I get paid well and I have stock options, not to mention hefty annual bonuses. I love what I do, it sucks up a lot of my time though, but since the pandemic, I’ve mostly been able to work from home and be with my daughter when she’s out of school.

The downside, my social life has been dead and buried since before Angelique left. I was too focused on work to maintain a social life, and certainly couldn’t keep her happy, which is why she said she left. It didn’t bother me for the most part, except late at night when I found myself on my phone at 2 am stroking myself raw until I nut and fell asleep. Tonight was no different until I got a message on Instagram from my high school best friend Jamal.

Jamal: yo, are you going to Allie and Drew’s wedding?

Normally, getting a DM at 2 am I would get excited, expecting it to be some girl telling me she wants to ride my dick. Jamal is not that girl, but my dick did twitch remembering how we would jerk off together back in high school. We were really tight back then. We started jerking off together once in a while back in 8th grade, but by the time we graduated, we were really into it. Always finding time and place to just frot and jerk each other off. It was always hot when he would cum on me “by accident,” but it was obvious to me that he did it on purpose. It awakened a need in me that I took to college and ended up having a few cruising experiences that I absolutely loved. I always played safe though, even with girls I wasn’t trying to get anyone knocked up. The one time I got drunk and let Ange ride my dick raw she got knocked up, it turns out I don’t have the control I thought I had.

Me: Of course, my hotel and flight are already booked.

Jamal: Awesome, you think I can split a room with you?

Me: If you want, you and Rachelle don’t want privacy?

Jamal: Damian, bruh, Rachelle broke up with me like two months ago, we’ve kept it on the DL because she doesn’t want it to be a topic at the wedding. We were gonna share a room, but now that she’s dating some fuckin white boy from her office I have no interest in pretending for her sake.

Me: damn bro, sorry to hear that. Of course, you can split the room with me, it’ll be like old times!

Jamal: thanks D! I looked into getting my own room but since it’s next week all the prices are double, I can afford it but fuck that shit.

Me: It’s really no big deal. My flight gets in at 1 pm, and check-in is at 2 pm so I should be at the hotel from the airport just in time.

Jamal: dope, my flight lands at 3 pm, I don’t want to hold you up, just leave me a key at the front desk?

Me: that works!

A week later I got to the hotel, and this is where things immediately set into motion how the weekend would go.

“Yes, Damian, I have you in a King with the wedding block?” the lady at the desk asked.

“That sounds right,” I scrolled through my messages on my phone, not really paying attention.

“Did you want to use the credit card on file or another card?”

“The one on file works,” I looked up and smiled.

She was cute, very pale, with dark brown hair pulled back in a ponytail, big eyes, and a bigger smile.

“Great, did you want one or two keys?”

“Oh yeah, two keys for sure, and can I leave one here to be picked up by my boy Jamal when he gets in around 3:30?”

Her face changed expressions, to an almost surprised look, “Umm, sure, that’s fine.” She clicked on the keyboard and then slid an envelope across to me, along with a gift bag that everyone was getting from the bride and groom. “You’re all set. The elevator is down and to the left,” she put on a fake smile.

I found the room, went in, and dropped off my stuff. Checking my watch to see what time it was, then sent a few texts to let my parents know I made it safely, let the groom and best man know I was here, and let Jamal know I was checked in and what room we were in. I decided to take a quick shower before Jamal got in. I sat on the bed to take off my shoes, and thought, “damn this is a big comfy bed,” and that’s when it hit me there was only one bed. I chuckled to myself and fired off a text to Jamal, “So…funny story, there’s only the one bed in the room because I booked the room before I knew you’d be staying in here. Don’t worry, it’s a king size though so we don’t have to cuddle.” 

I hopped in the shower and when I walked out of the bathroom, dick swinging I was met by Jamal sitting on the bed reading his phone.

“Oh shit,” I pulled the towel from around my neck to cover my junk. “I didn’t hear you get in.”

Jamal grinned at me, and I’m certain he was checking out my body as his eyes moved up to meet mine, “yeah, my flight landed early,” he bit his lower lip. “You don’t have to be shy around me man, we have too much history for you to suddenly be shy,” he chuckled at how I was trying to hide myself.

It’s been 8 years since we last saw each other naked, jerking off in his room on a hot summer night before we went away to different colleges. I’ve put on 20 pounds of muscle since then and developed from a boy to a man for sure. He looks like he put on at least 30 pounds of muscle since then, and lost all of his baby fat, like he’s been playing ball all day every day since high school. I dug into my bag and slipped on some white CK boxer briefs that popped on my chocolate skin.

“Drew said everyone is meeting at the hotel bar for a pre-wedding drink and shenanigans at 6,” Jamal said, still keeping his eyes fixed on me as I put on lotion before getting dressed.

“Ok, great, I’m gonna Facetime my daughter before heading out, it’s going to be too early for her bedtime there, but I’m not going to Facetime her when we get back from the bar,” I laughed, giving him a knowing look.

“Why don’t you do that, I’ll take a quick shower, get that nasty airplane air off me and we can go pregame at that place across the street,” Jamal adjusted his dick before standing up and walking into the bathroom.

I tried not to think anything of it. We keep in touch, but I see him less and less since high school, I think because of the pandemic I haven’t seen him in person since my daughter was born. So I’m not trying to pretend we’re close like we were and I’m not going to assume he would still do a fun frot session with me like we used to.

We went out to the bar across the street, it was kinda lame, but a couple of the guys from the old neighborhood were already there playing darts and having drinks, so it was fun to catch up. Then we all went over to the hotel bar when the bride and groom got there.

Back at the hotel, I was pretty tipsy and I smoked for the first time in years with Drew so I was feeling pretty good. I stripped down to my boxer briefs and got in the bed. I didn’t mean to do it, but I was lingering above the covers and doing a pose that was asking for you to look up my legs to my crotch. I watched as Jamal stripped down to his boxers, trying not to notice the front bump of his dick swinging inside. I had flashbacks to when we were teens and this was a normal routine for us, stripping down and getting into the same bed, then he would slip his boxers off and we’d jerk off together. I felt myself getting hard at the memory and slipped under the cover.

“You still sleep with the TV on?”

I snapped out of my memory, trailing my eyes slowly up his body which…damn, he must be hitting the gym often to look that good, “I uh…I usually do, but I don’t care if you need it off.”

“It’s cool, I’m used to it,” he flipped through the channels and I drank in the muscle lines of his back, which now has a tattoo on the shoulder that snakes into a tribal tattoo on his bicep. He settled on one of the HBO channels, it was about 20 minutes into “Bad Boys” and he tossed the remote at me, then climbed under the covers.

I don’t know why, maybe because I didn’t jerk off the last three days, but when he got under the covers I got a whiff of his familiar scent that I hadn’t smelled in years and I swear my dick went rock hard as a natural reaction to it. My heart started beating fast just thinking about the possibilities.

“I can’t believe Drew is getting married tomorrow,” he shook his head, adjusting his pillow to get comfortable.

“I can’t believe a woman agreed to marry him,” I joked.

He chuckled, “for real, no way he can please her with that little dick!”

“Yeah, do you remember when we were in school and we all jerked off together, Drew bust his nut almost instantly when you touched his dick?” I blurted out and instantly regretted bringing it up, not sure if that’s something he wanted to pretend didn’t happen.

“For real, I never seen a dude nut so fast before or after that,” he chuckled, rolling over to his side, facing away from me.

“Well, all that matters is they are happy, so he must satisfy her in some way,” I mumbled.

Jamal didn’t say anything and a couple of seconds later he started snoring quietly.

I was so horny, I thought about jerking off real quick, but I was afraid he’d wake up and think I was a freak or something. So I did my best to distract my brain and fall asleep.

I woke up at about 4 in the morning to Jamal cuddling me from behind, I could feel his length between my cheeks, the thin material of his boxers, and mine the only thing that kept his hot hard poker from touching my hole. His big arms were wrapped around me, hugging my shirtless torso tightly to his shirtless chest, his warm steady breath on my neck, I was instantly as hard as he was. Unfortunately, he was sleeping. I didn’t want to wake him, this just felt right and I drifted back to sleep.

When I woke up to my 10 am alarm, Jamal was already in the shower. I called my parents to check in on my girl, and everything was good. They told me to stop worrying, reminding me they raised me just fine and that I needed to enjoy the weekend away.

The wedding was fun. Everyone drank a lot, people were routinely sneaking outside to smoke. I probably overdid it with drinks and weed, but whatever, I was having fun. I was starting to think Jamal and Rachelle were going to hookup tonight, they seemed to be getting along well, or at least that was what I thought. As soon as the bride and groom called it a night though, Jamal was done.

He came up to me, hooking his arm on my shoulder, “Bruh, I’m done.” He said with a smile. “I’m heading back to the room.”

“Ok, you ok?”

“Yeah, just sick of seeing her face and I’m not trying to be the reason she cheats on her new guy like she did to me,” his smile faded. “I’m gonna smoke with Carter and then head back, you coming?”

I grinned, “fuck yeah.”

I probably should’ve said no, I could feel my lack of tolerance as I floated across the floor, trailing behind Jamal as we went out for a smoke.

I couldn’t even tell you what we talked about because it was a blur.

Jamal was laughing at me back in the hotel room because I fell over trying to get my pants off. But I recovered with grace and did a strip tease as I did. Stripping down to a pair of black CK trunks that showed off my ass and thighs, hugging my package in all the right ways.

“Damn D, you never had that ass when we were in school,” he joked as he slowly undressed to his boxers.

I gave my ass a dramatic smack, “I do flag football with my brothers on the weekend, keeps me from becoming an overweight coder like my coworkers,” I joked, then flopped face down onto the bed, spreading out wide to take up the entire bed. It felt good to feel the soft bed under me, stretching out my muscles after dancing all night, I let out a soft moan and gently humped the mattress.

I felt Jamal get on the bed with me, suddenly laying on top of me, covering my body with his bigger, more muscular body, then he dramatically faked humping my ass, doing porn star moans as he did, ending it with a fake orgasm sound, slamming his crotch into my ass as if he just nut and rolled off me onto his back. He spanked my ass, “Hope it was good for you.”

I chuckled, turning my head to him, “Man, I didn’t even catch my nut.”

He laughed, “damn, I’m such a disappointment.”

I spread my arms and legs out again, making sure they brushed up against his, “you didn’t used to be, what happened?”

He chuckled again, “bruh,” he reached into his boxers, gently grabbing himself, “we used to have so much fun back in the day.”

I rolled onto my back, with one knee up, “Jamal,” I snickered, “I think I got more of your nut on me back in those days than I did my own.” My hand started stroking my already hardening cock from the outside of my trunks. I didn’t even try to hide it.

He chuckled, “Shiiit, I admit it, I liked to nut on you, something about it just…” he trailed off, his dick clearly hard in his boxers, “fuck man, I need to jerk off before bed, or I’m not gonna sleep tonight.”

“Me too,” I almost giggled, quickly yanking my trunks all the way off so I was naked and my dick was harder than it had been in years, snapping back to my skin as the waistband released it.

“Oh shit, ok, we’re doing this?” Jamal grinned, following suit, his boxers slipping down quickly, his big dick was already starting to leak precum. He started slowly stroking his dick, watching over at me to see what I was going to do. I let him lead, slowly stroking myself, needing release, feeling more horny than ever.

He shift around, sitting between my legs facing me like we used to do back in the day. We just scanned each other's bodies with our eyes, taking in the subtle changes since the last time we did this, fuck he looked good and smelled good, and I lay back down flat trying to not cum too fast. He spread his legs out, grabbing my legs and pulling me closer to him, putting my legs over his tree trunk thighs so my balls were bouncing with his balls as he started to stroke us together.

“Mmm,” I moaned, reaching up to grab the pillow at the head of the bed and slide it back under my head so I could watch him stroke me. I locked eyes with him again, biting my lower lip and rotating my hips to get more pleasure out of his stroking. His dick was slightly bigger than my 7.5”, a little thicker too. The heat radiating from his cock to mine as he stroked us was intense, a feeling I forgot about, and man it was turning me on. I moaned again, which made him smile, a joy I hadn’t seen in him in years.

He quickly hopped off the bed and ran into the bathroom, coming back with his toiletry kit, he wedges his legs between mine spreading my ass wide and I feel something hard pressing against it, sending a tingly sensation up my body as I gently stroked myself.

“What’s that?” I looked over at his kit.

“I got some stuff, just in case,” he grinned at me, digging into the bag with his free hand and pulling out some stuff.

I lift up the lube, holding it high above our dicks I let it drizzle onto us as he stroked it into our dicks and it coated his hand, not skipping a beat with his stroking.

I held up a condom and gave him a questioning look.

He grinned, “I didn’t know what this weekend would be like, didn’t want an oops baby,” he chuckled.

I held up a little brown bottle, “what’s this?”

“Poppers,” he said, grabbing the lube and drizzling more on our dicks, with more purpose than I had.

“What’s that?”

“It’s like the whippets we did back in the day, but way better, really loosens you up and helps you have a better orgasm,” he smiled, grabbing it from me, shaking it, and opening it quickly, inhaling on one side, then the other. “Mmmm, fuck,” he capped it and handed it to me, returning his hand to our dicks, leaning back on his other hand. I watched his abs flex as he stroked us.

I tried to mimic his actions, taking a hit off the poppers, holy shit that rush was intense. “Oh shit,” I moaned, feeling this awesome wave wash over my body as his stroking sent pleasure through my entire body. I fell back onto the pillow and let the spinning room and the feeling of his body just give me a pleasure I hadn’t felt…ever.

“You like it?”

“MmmHmm,” I rocked my hips up into his hand instinctively.

He shifted his weight, running his hand up my abs and back down, adding that much more pleasure, settling on my crotch, his big hand gripped my inner thigh, his thumb brushing my balls.

“Mmm, fuck Jamal,” I tossed my head over from one side to the other.

He dropped our dicks and started to massage my thighs, his hands gripped me tightly and it felt good, his thumbs pressing into that space between my balls and legs as he did and holy fuck it was like a pressure point I had never enjoyed release from.

“Oh shit,” I mumbled, rocking my hips to get more pleasure.

I felt his big dick drop below my balls as he continued to massage me, my hips rocking with his hands accidentally worked his cock between my ass cheeks and that hard heat slid across my hole as I gyrated under his hands. He released my one leg and started stroking my dick again, just a gentle stroke to keep me hard as if I could go soft in this situation. He rocked his hips a little and I felt his dick slide between my cheeks over my hole.

“Mmm,” I moaned, stroking my dick.

He grabbed the bottle of poppers and took a hit, then passed it to me. I felt him adding lube to his dick and then he started sliding it up and down my crack as I took a hit of the poppers. Then he gently pushed the tip on my hole, which resisted but the poppers let hip pop the head in and I groaned.

“Oh fuck, shit, fuck,” I clamped a hand on the part of his thigh I could reach. I took a deep breath, then another, “Are we really doing this?”

“I think we need to,” he said, pushing his cock slightly deeper into my hole.

I took another hit of the poppers, then another, trying to relax my ass for his big cock.

He waited for the poppers to rush over me and then pushed some more, and a little more until most of his dick was deep inside my bowels.

“Fuck D, your ass is so hot,” he massaged my legs and started stroking my dick again.

I tossed my head back on the pillow, I want to bottom for him, but fuck his dick is huge and I haven’t been fucked since college. “Shit Jamal, just take it easy on me,” I groaned under the expanding pressure of his dick spreading my ass open.

“Oh my god, D, you feel so good, I really want to do this,” He rocked his hips, trying to restrain himself from treating my ass like a vagina.

I took another hit of poppers, gyrating my hips on my best friend's dick, and fuck did it feel good. I hooked my ankles behind his hips, pulling him into me, letting him know I was ready. He leaned over me and curled his hips up into me, bottoming out, “Mmm, fuck that’s good,” he tossed his head back and groaned.

His dick was thickening already, I felt the pressure on my prostate, an amazing pressure I hadn’t felt in so long and I knew it was going to make me cum.

Jamal started thrusting into me, pulling and pushing most of his 9 inches into me. Pounding my prostate as he stretched and filled my chute with cock. I know from experience that he precums a lot and I can feel it lubricating my hole with every thrust, “fuck this feels good,” I moaned, pounding my dick harder and flexing my ass on his cock.

“So good,” Jamal moaned with me, “don’t cum yet, I want to cum with you,” he picked up the pace, recognizing the signs of my building orgasm.

“Fuck,” I pulled my hand away from my throbbing dick. I grabbed the poppers and took another deep hit, then another, enjoying the sensation of Jamal taking my ass.

I looked into his eyes and felt a special moment between us that made me feel so good, like all my problems didn’t exist and in this moment we were all that mattered. He leaned in and kissed me, I wrapped my arms around him. We had never kissed before, he was so passionate and hungry, still humping my ass while sticking his tongue down my throat and moaning, holding me so tight his abs were massaging my cock and I was definitely going to blow.

I couldn’t stop it so I leaned into it. With every thrust of his hips, I lift mine to meet it, getting more dick with every pump. I just kept moaning into his mouth, rocking my cock up his abs like a washboard massager that was warm and vibrating every time he pumped into me. I couldn’t handle it, breaking our kiss, “Ungh, I’m cumming,” I moaned, my ass clamping down on his cock as I shot a load of cum onto his abs. He kept thrusting into me, pushing through my clamping ring and I shot even more cum onto his abs as he lay flat on me and rabbit fucked me, fast and furiously.

“Fuck D, I’m about to nut, oh fuck I’m gonna bust,” he moaned in my ear, hugging me tightly as he fucked me harder and faster until his dick exploded inside me. Unleashing molten hot cum deep inside with a loud groan, “Oh fuck, ungh, take that nut bro, mmm,” he slammed his hips into me again, and I felt his dick throb inside me some more the massive amount of extra liquid inside me was so warm and silky as his dick slid out and back in to let the last of his nut dribble into me. “Holy fuck,” he collapsed onto me, kissing my clavicle and hugging his orgasm into me.

I tried to catch my breath with his full weight on top of me, “fuck…did we just do that?” I was speechless.

Jamal blew out a deep breath of air, “Bro,” he half chuckled half gasped for air, “We just did that…and it was fucking hot.”

He continued to lay on me, his dick still inside me. I just gently rubbed my hands up and down his back. I don’t want to let go of this moment, I just want to drink it in and live in this moment. Slowly but surely, his cock deflated inside me and slipped out of my hole, he rolled off of me onto his back, grabbed his boxers, and wiped the cum off his abs and then mine, tossing them onto the floor. He didn’t say anything, just slid up next to me, put his arms around me, and cuddled me until I fell asleep.

The next morning I woke up, and he was already in the shower. I felt his dried cum in my ass crack, my head was pounding.

Jamal came out of the shower and got dressed, grinning at me the entire time.

I rubbed my temples, “what the fuck are you smiling about?”

He chuckled, “I tapped that ass last night,” he said, zipping his pants.

“Geeze bro, act like you’ve fucked before,” I felt a rush of blood hitting my cheeks, thinking how proud he was that he got to fuck me.

“We are expected at breakfast with the newlyweds in the restaurant downstairs, after breakfast I want to fuck you again,” he pulled on his shirt.

“Is that how it works now?”

“That’s how it works now,” he smiled at me, then scooped his boxers off the floor from last night and chucked them at my face.

“Ugh, gross,” I batted them away.

“Bruh, you still have my cum in your ass, all the dried nut on those is yours,” he grinned. “Hurry up and shower, you smell like sex and booze.”

I took my shower, letting it all sink in.