A Late Night Encounter

The relationship between my brother-in-law Reuben and I started off innocently enough. He had married my older sister Allison about two years after they graduated college, having been together since sophomore year. I got married another two years after that to Glen. As is typically the case, we spent most holidays together with our family, usually going to my parents' house, since it was large enough to comfortably contain a dozen or so people.

Last Christmas, we all gathered together as a family to make up for missing out on it the year prior. A few days before Christmas, Glen was working on his laptop in the den when I entered to pick up a bunch of the toys my three kids had left strewn about. Normally, I'd make them do this, but I was worried that they'd be a hazard, especially to my parents. I was wearing a plain green tank top and a pair of jeans that fit snugly, so when I got down on my hands and knees to clean up everything, they really squeezed against my ass.

"That's a view I don't mind seeing," Glen stated. I could feel him ogling my backside, watching me intently as I was in this compromising position.

I'd been aware of his attraction to me for a while, because Allison once let it slip while drunk that he'd confessed this fact to her after my wedding. Reuben and spent our first night as husband and wife in this house, to avoid ballooning our wedding budget more than we already had. Allison and Glen were staying in the room down the hall and around the corner from us, but there was a shared wall between them that both beds happened to be against.

Apparently, they heard us having sex, and Glen got so turned on that he started fucking her while she was still asleep. She went to bed in just her nightie, so he was able to enter her from behind as she was lying on her side. When she finally did wake up, she felt him deep inside her pussy, his thighs grinding into her ass. In a daze from the abrupt manner which she awoke, combined with the intoxication of how passionately he was fucking her, she wasn't certain she'd heard him right when he grunted into her ear, "I'm gonna pump you full of my cum, Jessie."

The next morning, after she'd had time to replay what happened the previous night over again in her head, she was convinced he'd said my name. So she asked him about it, and he told her that he'd gotten caught up in the fantasy of him fucking me on my wedding night instead of Reuben. They talked about it for a bit, during which time he revealed that he fantasized about me a lot. She also told me that the best sex they ever had was when they would roleplay, with her pretending to be me.

I was a little weirded out by this initially, but as she seemed to be fine with it, I never brought it up again. However, it definitely made me look at Glen differently. By this point, the fire in my marriage to Reuben had long since fizzled out, and I was more than happy to indulge my brother-in-law when he made suggestive comments, flirting back and enjoying the attention.

"I'm sure you've seen plenty of women down on all fours in front of you," I said playfully.

"True," he replied, "but they didn't have grape jelly stains on their shirts. That's the secret to really grabbing a guy's eye."

I sighed and said, "I don't think I own any clothes that haven't been covered in some sort of mess."

"I'll bet. And some being more fun to get than others," Glen retorted.

Although our exchange ended there, later that night, I heard my sister and him going at it. We were in the same rooms as my wedding night, except the arrangements had been swapped, so they had the bigger one. I couldn't help but wonder if Allison was pretending to be me as her husband pounded into her, and the thought got me a bit aroused. I wanted to feel a cock inside me, so I reached over to rub Reuben's crotch. He'd put in some airpods in order to listen to music while he played a game on his phone, so he couldn't hear what was going on in the room beside us.

"Not now, babe," he said, brushing my hand away from him. Unfortunately, that had become an all-too-common refrain from him in the last few years. It bothered me that he seemed to have lost interest in having sex. I'd worked hard to shed the baby weight I'd gained after our third child was born, and if you'll excuse me for bragging a little, I think I'd gotten in incredible shape--maybe even better than I was when we first got married.

"You say 'not now,' but you're never in the mood later, either," I complained, but he didn't hear me.

Obviously, I wasn't going to get what I wanted from him, so I grabbed my bag of toiletries and took them into the bathroom. I'd stashed my well-worn dildo in it, which I intended to use as a substitute for my husband once more. I perched on the edge of the bathtub and got to work. I pictured the salacious events occurring in the other room at the moment, getting so turned on that it didn't take long before I came.

On my way out of the bathroom, I heard the other bedroom door open, and Glen appeared from around the corner. He was only wearing a pair of basketball shorts, leaving me free to admire the rest of his body. While Reuben had let himself go since our wedding day, Glen spent plenty of time in the gym, so his abs and pecs were very well defined. His arms weren't overly bulky, but his thighs and legs looked quite powerful.

"Fancy meeting you here," he said when he saw me.

Even though there was no conceivable way that he was aware of what I'd just done, I still turned red from embarrassment. "I just needed to use the bathroom," I lied, although trying to justify my being in there was unnecessary.

"I hope we haven't been keeping you up," Glen stated, an impish grin plastered on his face. "Sometimes I forget we aren't alone here."

"Nope. I haven't really heard anything," I lied again, causing him to frown in what I read as disappointment. "Anyway, I'm gonna head back to bed. See you in the morning."

I'm not sure why, but I avoided Glen the next day. I didn't stay in a room with him for too long, and I refused to meet his gaze. He made a few of his typical flirtatious comments, but to his confusion, he didn't even get a slight chuckle in return.

That evening, while Allison and I were alone washing dishes, she asked me, "Are you mad at Glen for some reason? He said you've been acting weird around him all day."

"No, I'm not mad at him," I answered. "I just felt a little awkward, cause he saw me coming out of the bathroom after I'd just masturbated."

Allison laughed at this and said, "Oh my word! Okay. I wouldn't worry about it, though. I don't think he knew that's what you were doing in there."

"Yeah, but I knew what I was doing in there," I noted emphatically. "It's the same reason I don't save any porn to my phone. Even if nobody ever sees those kinds of pictures on it, knowing they're present at all while showing someone my photos makes me feel weird."

"Gotcha. I thought maybe you were upset because you overheard us having sex.

I suddenly realized that excuse would've been a much simpler explanation, and cursed to myself that I didn't use it.

I woke up around 2:30 AM to use the bathroom, and after going back to bed, I laid there for over thirty minutes, unable to get to sleep again. I figured I'd go downstairs and watch some TV for a while. The house was dark and quiet, so I assumed everyone else was still asleep. However, after I walked through the kitchen and entered the den, I discovered someone was already in there. The light wasn't on, but the glow of a laptop illuminated Glen's face. He was staring lasciviously at the screen, and through the shadows, I thought I could see his hand moving down between his legs.

It took a minute for him to notice I was standing in the doorway watching him. When he finally did, he jumped in surprise, fiddling around with his pants before ripping his headphones off. "Shit, Jess! You scared the crap out of me!"

"What're you doing down here?" I asked, a note of titillation in my voice. I had a pretty good idea what the answer was, but I wanted to hear him try to explain it.

"Just watching YouTube," he replied. I could see the embarrassment etched on his features, and couldn't help but feel like it was fair play, considering how I'd felt when I saw him after I'd masturbated.

"It must've been quite the video, considering how into it you were getting." Entering the den, I strode across the room, sitting down on the couch next to Glen. From this vantage point, I could see the obvious bulge in his pants. Despite there being plenty of room, I made sure I sat so close that I was practically on top of him. "Show me what you were watching."

He had a browser tab onscreen opened to YouTube, but it was the recommended videos page, rather than any specific one. I could see the telltale grayed out background of an incognito window peeking out just behind it. Before he could stop me, I grabbed the mouse he was using and clicked on it, revealing a video on PornHub titled, 'Horny MILF gets double stuffed.' It was paused on a shot of a pretty young blonde with one guy's cock in her mouth, and the other in her pussy.

"This isn't what it looks like," he said defensively.

"Really? Cause it looks like you were watching porn and jerking off," I told him. Running my hand over his crotch, I felt it jolt at my touch. "You're even still hard."

I clicked play on the video and turned up the volume so we could just barely discern the audio through the discarded headphones. The girl was making so much noise as she got fucked that I wasn't surprised Glen hadn't heard the squeaky floorboards as I came downstairs and into the den. The scene he was watching got me going as well, and without thinking about it, my hand slipped down the front of his pajama pants. Reuben and I used to watch a lot of porn together, and he always liked it when I started jerking him off in the beginning, so the action was almost instinctive.

"Jessie...what're you-?" Glen began to say, but when my thumb brushed across the head of his engorged rod, swiping through the copious amount of pre-cum, he was interrupted by letting out a moan. I then ran the rest of my hand through it, using his pre-cum to lubricate his shaft when I began stroking it. "God, that feels so good," he murmured.

His own hands found their way up the bottom of my oversized nightshirt, pushing aside my panties so he could rub the outer lips of my pussy. I was already wet, and feeling his touch while watching the porn video only made me wetter. The moment he pushed a single finger past my threshold, sinking deep into the soft, hot flesh, I let out a moan of my own. He caught it with his mouth, pressing his lips against mine as he initiated a kiss.

While Glen worked his fingers in and out of me, and I pumped my hand along his shaft, we kissed passionately. Our tongues intertwined as they fought for dominance between our mouths. As he brought me closer to an orgasm, I broke off the kiss and buried my face into the side of his neck to muffle my moaning. My hips were thrusting against his hand faster and faster, until I was essentially fucking it. The overwhelming ecstasy took hold of my body, and I convulsed wildly as I came, sending a flood of juices out around his finger and dripping down my bare thighs.

Having climaxed, all my focus was now on getting Glen off. I halted for a moment to tug his pants down just enough for his cock to spring free. I absolutely devoured it with my eyes, a bit in shock when I saw just how massive it was. If I didn't envy Allison before, I certainly did now. It was no wonder she was screaming so loud when he fucked her.

I turned to look at the laptop screen, and he did the same. The girl was still on the bed, but the guy behind her was standing on the floor, holding her up on just her knees by her throat, while the other man stood on the mattress and fucked her mouth. As I wrapped my fingers around Glen's member again and resumed jerking him off, I whispered seductively into his ear, "If that was me, would you wanna take my mouth or my cunt?"

"Your mouth," he replied in a strained voice. He was fighting to maintain his composure while my hand was sliding up and down his length.

Without warning, I repositioned myself on the couch so that I could lean down and take him into my mouth. His cock shuddered as it passed through my lips, allowing me to run my tongue along its underside. I'd only been sucking him off for about thirty seconds before he changed positions as well, turning to face me with his back propped up against the sofa's armrest. Now he had enough leverage to grab the sides of my head and thrust his cock down my throat.

Once Glen took over, I barely had to do anything besides allow him to fuck my face. He pounded into it hard, and I was struggling to take his enormous girth. There were several times where I began to gag, but this only spurred him on more. Soon, he was like a feral beast, fucking my throat with an unrestrained zeal.

I was finally able to get a very brief opportunity to come up for air when he had to scoot back against the armrest, his body having slipped down along the sofa from the strength of his thrusts. As I was gasping, strands of saliva and pre-cum stretching between his throbbing spear and my lips, I told him between breaths, "Tell me how much you love fucking my mouth."

We resumed our activities, and he seemed to be going even harder now. "I love the way you suck cock," he uttered through a groan. "You're a dirty little cumslut, aren't you? I always knew you craved a big, fat, juicy cock like this in your mouth. I'm gonna fuck your throat until you're choking down my hot load like a real slut!"

Before I knew it, Glen's prediction came true. The only warning I got was his rod tensing up in my mouth, and then it was spewing hot cum in my mouth. I gulped it down as fast as I could, but there was just too much to contend with, and I coughed, causing the thick semen to spill out. He seemed to enjoy this, and he pulled my head off his cock, then ran two fingers around his balls, gathering as much of it up as he could. I was still panting when he pushed his cum-coated digits into my mouth, and I sucked them clean greedily, making sure to get every last drop.

"That was amazing," he said, letting out a contented sigh. "Now I'm spent. I should head up to bed."

"That took a lot out of me, too," I concurred. "Maybe I'll be able to fall back asleep."

"Don't clean yourself up, though," Glen urged. "When your husband kisses you tomorrow morning I want him to taste another man's cum on your lips."

"We'll see," I said noncommittally. "Have a good night."

He closed his laptop and stored it away in its case, then departed from the den. I laid down on the sofa, feeling the damp material on the cushions beneath me. I was still pretty horny, so I got myself off one last time before finally drifting off to sleep.