Late Night Company

ThatBoi21©

It's late at night, and I'm at my friend's house trying to sleep.

Emphasis on the word trying, as my friend, Todd, is snoring too loud for me to actually sleep. I normally try to fall asleep before him, but this time I messed up. I knew I should've focused on sleeping instead of looking at my phone for an hour.

I close my eyes and try to force myself to sleep, but just like I expected, it doesn't work.

"Maybe I'll go upstairs and watch some TV or something." I think to myself, sighing.

I roll off of the blanket I laid out on the floor and stand up. The only light filling the room is the moonlight spilling in through the window. I glance in the window and look at myself. I observe my toned chest, abs, and shoulders, admiring the body I work hard to maintain.

"Probably should put a shirt on." I think to myself, slipping on my T-shirt.

It'd be kind of awkward if Mr. or Mrs. Winslow caught me just watching TV upstairs, shirtless. Of course, I don't think I would actually mind Mrs. Winslow catching me. I mean, I've fantasized about her since the day that I met her.

I'd love to grab a fistful of her long brown hair, yanking it back as I slam my dick in and out of her, watching her thick ass jiggle with each thrust. I'd also love to see those huge tits of hers bounce up and down as she rides my cock, her hands on my chest for support.

"Fuck, I better stop thinking about that before I get hard." I think to myself.

I begin to walk upstairs, and as I get near the top, I can hear the TV on. A little weird, as I don't know who else would be awake at this time. I keep walking, and make my way to the living room. I peek inside, and see Mrs. Winslow sitting on the couch, wearing nothing but a pair of short shorts and a tank top. No bra either, as I can see her nipples poking through.

Before I can start fantasizing about her, she looks over and sees me.

"Oh, hey Tony!" she says, smiling at me.

"Hi, Mrs. Winslow. What are you doing up so late?" I ask, smiling back at her.

"I could ask you the same thing!" she says, laughing a little.

I walk over and sit next to her on the couch. I glance at the TV and see that it's some infomercial playing.

"Well, Todd sort of woke me up with his snoring." I tell her.

"God, it's like all the men in this family snore! Jeremy woke me up about an hour ago, so I just decided to watch some TV and sleep out here on the couch." she explains.

"Yeah, Todd was getting pretty loud, so I wanted to watch some TV up here too." I say, scratching the back of my head.

"It gets annoying, doesn't it? Imagine being married to someone who snores! I always have to go to bed before him if I want to get a good nights rest." she tells me, seeming a little annoyed.

"Why didn't you go to bed before him this time?" I ask her.

She's a little caught off guard by this question, for some reason.

"I was uh... doing stuff." she says.

I sneak a glance at her chest and see that... her nipples got a little hard? I'm probably just seeing things.

"Uh-huh... so, what are ya watching?" I ask, turning to the TV.

"Oh, it's just some stupid infomercial. I just like to watch these things when I'm bored." she tells me.

We watch infomercials for a good 30 minutes, talking and laughing all the while. Then, an infomercial about some magic workout equipment that claims it'll get you ripped in a month comes on.

"Hey look, another product you don't need!" she jokes.

Did she just give me a compliment? I think I'll go ahead and clarify.

"Oh really? And what do you mean by that?" I ask, smirking at her.

She rolls her eyes and smiles at this.

"Don't act like you don't know. You're ripped!" she says, giggling.

I laugh at this, leaning back and flexing a little bit.

"I'm glad you've noticed." I joke.

"It's kinda hard not to, what, with how much you come over to swim." she tells me.

"Oh, so you've been sneaking some peeks at me?" I tease.

"Don't act like you're not flattered!" she says, jokingly hitting me on the arm. "Besides, I've caught you checking me out plenty of times." she tells me.

"Like when?" I ask, liking where this conversation is going.

"Well, there was that time that I came out and swam with you guys in that one piece I have. Remember, the black one?" she asks.

"Oh yeah, I remember." I say, thinking back to how hot she looked.

"And there's all those times I've bent over to pick something up, and I see you staring at my ass out of the corner of my eye." she says, smiling.

"Hey, you've got a nice ass." I tell her, smiling confidently.

"I don't think that's a very appropriate thing to say to your friend's mother." she says, trying her hardest to seem serious.

"I don't think you mind much." I reply.

She smiles and turns back to the TV. I'm for sure not letting this conversation end with that.

"So when have you looked at me?" I ask her.

"Well, I... I don't wanna say." she says, laughing awkwardly.

"Come on, I've admitted to looking at you all those times. It's only fair if you do the same." I tell her.

I sneak a glance at her tits again, and notice that her nipples are getting hard. This time, I'm sure of it.

"Well... God, this feels so wrong to say but... sometimes when you get out of the pool, your trunks stick to you. And I can see your uh... your-" she says, fidgeting a little bit.

"My cock?" I say, finishing her sentence.

"Yup. Your uh... your cock." she says, nodding.

I'm grinning ear to ear right now. I thought I could push this even further, but she turned to face the TV again. But, after about 10 minutes, she speaks up again.

"The reason why I didn't fall asleep before Jeremy is because I was uh... I was touching myself." she tells me.

I smile again, and I can feel my cock getting hard.

"What to?" I ask.

"...You." she says.

Without another word, I grab her wrist and set it on my cock, letting her feel it get hard.

"Tony!" she exclaims.

Despite saying this, she doesn't move her hand.

"What? Since you were touching yourself while thinking about it, why don't you go ahead and touch it?" I ask, smiling.

"But what about Todd? And my husband?" she says, seeming hesitant.

"I doubt you were thinking about them while you were masturbating to the thought of me." I tell her. "Besides, I won't tell." I say.

She looks around a little, as if someone's gonna just walk in without making any noise. After that, she grips my cock through my pants gently and begins to rub it. I lean back and let her keep stroking it, letting it grow to full size.

"You like it?" I tease.

"It's really big..." she says, staring at my huge bulge.

"Bigger than your husband?" I ask, smiling wide.

She simply nods in response, still rubbing my cock. Feeling her hands gently rub it feels nice, but I think I know how to make it feel even better.

"Wanna see it?" I ask, smirking.

She pauses for a little bit, not moving at all. She gulps, and then nods her head again.

With that, I unbutton my pants and pull them down, giving her an even better view of the outline of my cock, now almost ripping my boxers from how hard it's gotten. She reaches for my bulge again, but I yank down my boxers, letting my fully hard cock spring free.

I was watching her face the entire time as I pulled it out, and suffice to say, her reaction was definitely a confidence booster. Her eyes were wide open, and her mouth hung open in surprise when she saw just how big I am.

I laugh at her response, as she's still staring at it in shock.

"Holy..." she mutters, admiring my cock.

"Big, isn't it?" I tease.

She just nods in response while her mouth still hangs open. She doesn't take her eyes off of it for a second, and it's as if she's trying to burn the sight of my cock into her mind with how much she's staring.

"Go ahead, touch it." I tell her, running a hand through her hair.

She gently wraps her dainty fingers around my thick cock, and holds it while staring at it. Slowly, she begins to stroke up and down, and I watch as my friend's hot mom, who all of my friends want to fuck, strokes my cock while staring at it in awe.

With long, slow strokes, she runs her hand along every inch of my cock. I see her bite her lip as she jerks me off, and she speeds up her hand.

"Like what you see?" I ask.

"It's really big..." she says, stroking even faster.

She licks her lips while looking at it, and to my surprise, she moves her head towards my cock on her own. She wraps her lips around the head of my dick, and slowly slides down, trying to take in as much as she possibly can.

"Fuck..." I moan out as she slides more of my shaft into her mouth.

I hear her moan on my cock in response, and she begins to move her head up and down, going as far as she can. She can fit most of my cock in her mouth, but I'm too big for her to take it all. Guess she wasn't getting much practice with her husband.

She gags every now and then, but that doesn't stop her at all. Hearing her struggle like that but keep going makes it even sexier somehow.

Her mouth feels amazing, as she runs her tongue along my cock as she sucks, and to my surprise, she's better than a lot of the girls at school. Being my friend's hot mom, however, easily makes this one of the best blowjobs I've ever gotten.

With one of her free hands, she grabs onto what she can't fit into her mouth and holds it to keep my cock steady while she bobs her head up and down. The sounds of her slurping and sucking on my cock fill the room, luckily not loud enough to wake anyone up, so I can keep enjoying this without fear of the two of us getting caught.

She's been sucking for a while, and hasn't come up for air for once. I wonder how the hell she's doing it? I doubt breathing through her nose would be comfortable with how much is in her mouth and how much she's moving.

Just then, she comes up for air, taking in a deep breath. Speak of the devil.

"God! There's so much!" she says, laughing.

"I could tell you were having some trouble fitting it in your mouth. I'm guessing you don't get to practice on a big one since you're with your husband, huh?" I tease.

"Well, he's about... half your size, so not really." she jokes.

Well, hearing that certainly is a confidence booster.

"A lot thicker too?" I tease.

She nods in response, and begins to jerk me off again. This time, it feels better as it's now lubed up from her spit.

"This feels so wrong..." she says, laughing awkwardly.

"Really? Feels pretty good to me." I joke.

"Not like that! You know what I meant." she says, laughing.

"Well, this can just be our little secret. Besides, I can tell that you're enjoying it." I tell her.

"And how can you tell?" she says, smirking and raising an eyebrow.

"Because if you weren't into this, you would've left the moment I placed your hand on my bulge." I tell her.

"Well... you got me there." she says, laughing again.

She turns her attention to jacking me off again, her dainty fingers moving up and down my shaft. She's stroking it faster than before, and it feels amazing. Just when I think it can't get any better, she wraps her mouth around the tip of my cock and just licks and sucks on it while jerking me off still.

"Holy shit, Mrs. Winslow!" I moan out, unable to control my voice.

I hear her giggle on my cock, and she removes her mouth off of it.

"Call me Caroline." she tells me, licking the tip of my cock.

"Fuck, Caroline..." I moan as she keeps stroking me off.

She's been stroking and sucking my cock this entire time, so I decide I need to return the favor.

"Caroline, sit on my face." I tell her, laying back onto the couch.

I watch as she stands up and pulls her shorts and panties off. She slowly straddles my face, and I grab onto her hips to keep her still.

I work my tongue inside of her wet pussy, enjoying the fact that both the smell and taste are nice. Once inside, I move my tongue around inside her pussy, listening to her reactions to see what she likes. She moans, but I decide it's not enough.

I lift her up a little bit, thank god she's light, and begin to use my tongue to tease her clit instead. As I expected, this gets a better response from her. Her moans are louder than before, which is exactly what I wanted.

I keep licking and sucking her clit while all she can do is grip onto the couch and moan. She tries to cover up her mouth to hide them, but I don't want her doing that at all. I tease the spot that makes her moan the loudest, and she removes her hand to grab onto one of the pillows, her moans escaping now.

"Don't hide it. I want to hear you." I moan, before going back to pleasing her.

"Shit, Tony..." I hear her moan as I keep teasing her.

I push her down against my tongue, feeling her shake with pleasure as I keep pleasuring her with my tongue.

"Oh my god!" she loudly moans.

I was planning on doing some more, but it seems Caroline had different plans, as she got off of my face.

"Just lay right there. Fuck, I can't wait anymore..." she says, as prepares herself to mount my cock.

Slowly, she inserts my cock into her tight, wet cunt, and slides down to the base of my cock. She puts her hands on my chest to hold herself up.

"You're so big!" she moans.

I reach to grab onto her hips to make it easier for her, but she has something else in mind.

"No, keep your hands to your side. Just let me do all the work for now." she says, beginning to slide up and down my cock. Her pussy is gripping onto my cock tightly, and I can feel my cock stretching her out.

"You feel so gooooood..." she says, riding me even faster.

I still can't believe that this is happening. My friend's hot mom is riding my cock while both Todd and her husband are asleep. Not only that, but she's admitted that my cock is the biggest she's ever seen.

All of my friends have talked about how hot she is and how they've wanted to bang her. How they wanted to see her big tits bounce as they fuck her, while she moans their names. But while they can only think and imagine it, I get to see and hear it. I get to know how her pussy feels, what her moans sounds like, and how she's great at giving head.

I do feel a little guilty for fucking Todd's mom though. I guess as long as he never finds out, then it's like it never happened though. What he doesn't know won't hurt him.

I turn my attention back to the hot MILF riding my cock, and she's sped up even more now. She's panting and moaning like crazy, and she looks at me and smiles when she catches me watching her.

"I'm sorry it just... fuck, it just goes so deep!" she tells me.

I don't know why she's apologizing. Maybe she thought the face she was making was weird or something?

"Don't be sorry. It's sexy as hell when you let loose like that." I say, watching as she keeps bouncing up and down on my cock.

She smiles at this, and moans loudly as she slams down on my dick again. The room is filled with the sounds of our moans and our bodies slapping together. If Todd or Mr. Winslow woke up, they would instantly know what's going on. But that just makes it even hotter to me. Knowing that we could get caught at anytime, that Mr. Winslow could walk in at any moment and see his trophy wife riding his son's friend, makes it so much more exciting.

Caroline then falls forward, my cock still inside of her.

"Sorry... I'm just... I'm just a little tired." she pants.

"I'll take over, then." I say.

I grab onto her ass and begin to thrust up into her, feeling her tits rub up and down my chest as I fuck her. I can hear her moans right in my ear, which makes me pound her even harder.

"Tony, you feel so fucking good!" she moans into my ear.

I grab onto her ass tighter and spread her cheeks as I slam up into her over and over. As I keep fucking her, she grabs my face with both of her hands and kisses me hungrily. She shoves her tongue into my mouth, to which I happily reciprocate.

Damn, fucking AND making out with his mom. Todd would kill me if he found out.

I grab onto her even tighter, and start fucking her as hard as I can. I can hear and feel her moaning into my mouth, unable to control herself now. As our tongues clash together, I can feel her pussy gripping onto my cock tightly, as if it never wants me to pull out.

Her tongue is moving around more erratically, and her moans have become more wild and louder. I keep going at the same speed and roughness, as I can tell that she's getting close to cumming.

Just as I thought, I can feel her tightening and loosening around my cock, and she's practically screaming in pleasure now. She would've woken up the whole house had it not been for the fact that her screams were muffled by our kissing.

I don't slow down at all until her screams die off and I feel her relax on top of me. Once she does, I slow down to a halt, and let her take a breather.

"That was... amazing..." she pants, cuddling up on top of my chest.

"I hope you can take some more, because I'm still hard." I tell her, smirking.

"I could take it all fucking day..." she says, kissing me again. "How do you wanna finish it off?" she asks.

I think about it for a while, before finally coming to a conclusion.

"I wanna fuck you from behind while you're bent over this couch." I whisper in her ear.

"Mmmmm... and where do you wanna cum?" she asks. "You can cum inside if you want. You don't have to worry about me getting knocked up." she whispers in my ear.

Fuck, I love older women.

"I'm gonna fucking fill you up." I whisper back.

"Why don't you go ahead and get started?" she says.

With that, she slides off of my cock and bends over the armrest of the couch, waiting patiently for me to slide my dick inside of her again. I get up off the couch and make my way behind her. I run my hands along her thick ass, enjoying the sight of her being bent over.

She then reaches behind and spreads her cheeks for me, obviously not wanting to wait any longer. Not wanting to disappoint, I grab my cock with one hand and guide it into her wet cunt. I rub my head up and down her pussy, teasing her.

"Please..." I hear her beg.

I chuckle, and then slide it inside of her slowly, savoring her warm cunt gripping onto my cock.

"Fuuuuuck, Tony, you feel so good..." she moans.

I spank her across the ass once, making sure it was hard to cause a loud noise.

"I can tell." I say, pumping my cock in and out of her.

"I think you'll have to start sleeping over a LOT more!" she says, giggling.

"Wanting you sons friend to sleep over more just so you can fuck him? Aren't you a bad mother." I tease.

"Oh, you fucking know it." she moans.

I watch her ass jiggle with each thrust, all while she's practically ripping a pillow in half with how hard she's holding onto it. Just from that single spank from before, I can see a red hand print on her ass.

I spank her again, this time on the other cheek. It leaves another hand print, just like I wanted.

"Like watching my ass jiggle?" she says, looking over her shoulder.

"Fuck yeah." I say, spanking her again.

"Mmmmm, better make those spanks a little more quiet. I don't want to wake anyone up." she teases.

"I don't think you want that." I tell her.

"And why's that?" she asks, smiling.

"Because I can feel you tightening up around my cock each time I spank you." I say, spanking her again for emphasis.

She moans out after I slap her ass, and I keep thrusting in and out of her. I feel a little bad for Mr. Winslow, as she probably won't be able to feel his dick inside of her at all after I'm done with her. I guess I'll just have to take over to make sure she enjoys sex from now on. I'm sure we can hide it from Todd and Mr. Winslow.

I tighten my grip on her hips and slam her back against me, earning a loud moan from her.

"Holy fuck!" she moans loudly.

"Like that?" I tease.

I begin to pump my cock in and out of her as hard as I can now, the sounds of our skin slapping together filling the room. With each thrust, I feel her tighten around my cock. The room smells of sweat and sex, which turns me on even more, knowing that Caroline and I caused all of this.

I spank her again and again, making the red hand print disappear as her entire ass became red. With each spank, her moans get louder and she pushes against me more, wanting my cock to go as deep as possible.

I grab a fistful of her hair and pull back, making her tighten up even more. Not only that, but her moans increase in intensity too. Who would've guessed that sweet Mrs. Winslow was actually a horny slut who loves to be dominated? I'll make sure to keep that a secret though. I wouldn't want her reputation as a perfect housewife to get ruined.

I slam into her again and again, and I can feel myself getting close to cumming. My thrusts get more erratic, and I begin to moan louder. Caroline can obviously tell too.

"Cum for me, baby..." she moans out.

I start thrusting faster, and the room is filled with the sounds of our moans and skin slapping together.

"Fuck, Tony!" she moans out.

With one final thrust, I shoot my load inside of her, filling her up completely. I shoot rope after rope inside of her, making her moan. I collapse on top of her when I finish cumming, panting.

"That was so fucking good, baby..." she moans.

"I hope no one heard us." I say, smiling.

"With how loud I was getting, I'd be surprised if they're all still asleep!" she says.

I laugh, and slide out of her. I'm more sensitive now, so I shake with pleasure a little bit as I pull out. I watch and see some cum start to spill out of her. She reaches around and feels some of it.

"Fuck, you really did fill me up!" she says.

"Told you I would." I tell her, smirking.

She shakily stands up, and laughs when some more drips out of her.

"You can go on back downstairs now. I'll make sure I clean everything up." she tells me.

"You sure?" I ask.

"Oh yeah, don't worry about it." she says.

I turn and begin to make my way to the door to downstairs, but she speaks up again.

"Oh, Tony? Make sure you get some rest. I think I'll want some more tomorrow morning." she says with a wink.

Jesus, this woman is amazing.