Mom and Doug were clearly not ready to let things go in their relationship, maybe they thought a vacation would make things work for them. But Mom was already pretty solidly with her coworker, exploring a side of her sexuality she never had before. And Doug was doing the same thing with me. As shameful as it is, and as rough as it got when it all came to light, at the time there was something about it that felt perfect. I was single, bored and horny. Doug was lonely and excited to learn about a new part of himself. Mom was getting what she needed. Why couldn’t we all just be honest about it?
But of course, that would’ve killed it. So we found ourselves in Doug’s Thunderbird, which was packed to the gills with luggage and beach shit, cruising the seven hours down to Ocean City, Maryland. I guess we were all in a good mood, the weather was nice and Mom and I have a deep love for the beach.
It was four hours in and the drive was starting to get pretty rote. I’d taken over driving duties and Doug was in the passenger seat while Mom dozed off in the back, a pillow against the hot window, the air conditioning keeping things cool. Doug was DJ’ing, some bad club music that I didn’t care for but it was good to drive to. He had on a pair of athletic shorts and clearly no underwear, which was pretty usual for him.
We were somewhere in Maryland and the road was long and flat. Mom had been dozing off for a good hour and now, when I looked back in the rearview, I could see that her eyes were closed. Doug turned around and looked at her, then looked at me. That look got my heart racing a bit. A few moments later, Doug said, real softly: “Hey.”
I looked over at him. He had a huge boner in his lap, an athletic-shorts silky covered rod that sat in his lap like a loaded weapon. He smirked at me. I shook my head. Doug glanced back at my Mom, shrugged and let his rod flex.
Despite myself I couldn’t stop looking at it and Doug knew. I shook my head again to show my disapproval but Doug just smirked. The next time I looked over he’d slipped his cock out of the bottom of his shorts. There it was: his big, shaved rod, hard, the head slick with juice.
Of course, I’d known we were probably going to have sex on this vacation. And I hadn’t been able to process how that was going to work. But the excitement I felt sent all that out the window. I was into this guy and he was into me.
I must have smiled a little bit at Doug because he reached over and took my right hand and brought it to his cock. I glanced nervously in the rearview but Mom was still seemingly out. I felt his thick, horny rod and stroked it. Fuck, I couldn’t deny that I was having some of the best sex of my life with him. My cock got completely hard in my shorts and Doug saw it and winked.
Just then Mom stirred and I took my hand away like I’d just touched a hot stove. Doug quickly slipped his cock back in his shorts and looked out the window like he’d just been watching the scenery go by.
Mom repositioned herself, now she was propped up against the seat full of bags next to her, her face positioned in the backseat between Doug and I almost as if she’d been observing us. Doug reached down and tweaked his boner a couple times as Mom’s breathing got slower. He looked back, then slipped the waistband of his shorts down so I could see his shaved pubic mound. His big cock flopped out, and the slap of it against the section of bare midriff where his shirt rode up was loud enough to make me fearful, but Mom just kept breathing.
Doug took my hand again, and despite myself I wrapped my hand around it. I squeezed and stroked and Doug laid back and closed his eyes for a moment. His hand went to my crotch and he grabbed my dick through my shorts. The more I stroked him the more juice seemed to flow out of the tip of his cock, lubricating his rod and making it easier to stroke him. I began to think I was going to make him cum, and we might have if my Mom hadn’t suddenly stirred and opened her eyes.
I tried to be casual about pulling my hand away and, similarly, Doug shifted away from me and tucked his cock back in his shorts in one motion. Mom blinked in the rearview, our eyes met. I thought she knew, in that moment. My heart was racing. But then she looked away and said, “How close are we?”
“Three more hours,” I said. Doug looked over at me and smirked. His cock was starting to deflate. I cursed myself for being so weak and playing so dangerously. But it was really just the start.
***
We stayed in a hotel suite that was really just one room, with Mom and Doug sharing the king-sized bed and me on a cot a few feet away. Why we’d ever thought this was a good idea was beyond me; Mom had booked the room, and probably we’d gotten it at the last minute with what little money Mom had socked away for vacation.
Once we got settled in we went down to the beach. Doug was clearly horned up, he was flirting with Mom and with me in his subtle way, and Mom was responding to him and when they said they had to go back to the room to grab some food and come back I knew they were going to fuck, cause they barely gave me a chance to go with them. So I laid there on the beach listening to the waves and trying not to think about them fucking though I absolutely knew that’s what they were doing. It wasn’t that I felt jealous…well, not completely, anyway. It was more the awkwardness of it throwing the situation into relief, where I’d just been flirting with this guy who was now fucking my mom, who was clearly having it both ways.
So I was surprised when they came back looking angry at each other and barely speaking. Doug flopped down on the chair next to where I was lying and Mom went straight to the ocean and dove in. Doug looked over at me and shook his head.
“Dude…we need some time alone. How are we gonna get it?” he said. I watched Mom swimming further out to sea. She loved to swim.
“I have no idea,” I said. In some ways I didn’t want to deal with it, the stress of sneaking around. But there was Doug, in his black trunks that rode up his tattooed thighs, his smooth and muscled body soaking up the sun, and I knew I was gonna take it as far as he would push it.
We got our chance the next day when Mom announced that we needed to go get groceries. It was easy enough for me to bow out of that, but Doug had a more difficult time; she wanted him to go with him but he made an excuse that he wasn’t feeling well. Mom shook her head at him and grabbed her keys and left. Any hopefulness they’d had around the vacation seemed to have vanished and it was looking to me like this would probably be the end of things for them, a last-ditch attempt that just hadn’t worked out.
Doug was flopped out on the couch and I was on the chair, watching TV. As soon as she left he got up and came over to me, straddling the chair and sitting on my lap. “Fuck I’m so fuckin horny,” he said to me as he settled onto my lap and got his face close to mine. “She hasn’t had sex with me in two weeks.” He moved his lips to mine and we started to make out. Then we were tearing each other’s clothes off, and it was like all the sexual tension we’d built up from the last time we’d done was pouring out, not to mention the horniness from laying on the beach in the sun and watching everyone walk around half-naked.
We got completely naked and we were both tan and warm from two days of sun, and our cocks were completely hard. Doug already had this incredible trunks-tan where his butt and hips were totally white around the brown frame of where the sun had hit him.
He was standing up and the air conditioning was blasting us and he watched me, breathing heavy as I got on my knees and took his cock in my mouth. He whimpered when it hit the back of my throat. I was sucking him roughly, hungrily, not being super careful with my teeth, even, but it was like he wanted it that way, it all felt so insane at that point how horny we were for each other.
I’d only started to lap at his balls when Doug flipped around and grabbed the back of my head to shove my face into his clean-tasting and shaved ass. I dug my tongue deep - my face was really buried in him. He was just whimpering and pressing his ass to my face and I couldn’t get my tongue deep enough. He braced himself against the wall and I slid a finger into him and reached around to stroke his hard cock as I fingered him.
When I stood up and embraced him from behind he reached around to position my cock against his hole, and after all that build-up, it just slid right inside him like we didn’t have time to mess around and it was way past due. It just felt right and we paused there for a moment, my cock pulsing in his tight hole, and Doug moaning and seemingly a little in pain but holding steady.
“You okay?” I said.
“Fuck yes I am, I’ve been wanting your cock in me for weeks,” Doug said.
“Goddamn,” I said, and started to pump him with it. To be honest we’d never discussed condoms, or PrEP - none of it had been mentioned, but that was where we were at I guess, just total abandon. Still, I had one eye on the digital clock on the bedstand, noting that maybe twenty minutes had gone by since my Mom left and we wouldn’t have a ton of time, nor any warning as to when she’d get back.
I felt his hole contract around my cock and I groaned. It had been so long since I’d fucked anybody and suddenly I felt self-conscious about how long I could last. Doug could tell, though.
“Are you close?” he said, and I felt his hole pulse around my rod.
“Yeah…maybe I shouldn’t move…”
“Just cum in me man,” he said and started to buck on my dick. He started jacking his own cock.
“Dude, you’re gonna make me…”
“Cum in me man, I want it. I want as many loads as I can get from you…fuck!” he said, and I felt him begin to cum, his hole tightening around my rod as he began to shoot. That did it for me: my cum seeming just spilled into him, like water looking for the path of least resistance. All I could do was hold on to his strong shoulders for dear life as his tight straight-boy ass milked every drop of cum out of my balls.
And that was that. We detached, caught our breath, and in ten minutes Mom was back and we were acting like nothing had happened. Which was weird, of course, but also strangely hot because we had this secret, still, connecting us. And I was watching Doug move around the kitchen in his basketball shorts, making us sandwiches to take to the beach, knowing my load was probably spilling out of him at that moment and him giving me winks whenever Mom wasn’t paying attention.
To be continued