Conditions

 Conditions

My Mom was 10 different kinds of gorgeous. She had long legs, a great ass, long dark hair, a killer smile, and a pair of tits that made people walk into walls when they couldn’t look away. So naturally, by the time my buddies and I were all 18, every last one of them was obsessed with her. 

I mean, she was the literal MILF next door. And honestly? I was right there with them. Oh, I tried to deny it at first. I was mad at myself. Then ashamed. I got Mom Son porn, and then got pissed at myself and deleted it all. But by the time I was 18, I’d just learned to accept it. Hell, it turned out that a parent fantasy was literally the single most common fantasy. So I really had nothing to be ashamed of. 

That said, it was weird, at first, when I couldn't’ stop getting boners around my Mom. I tried to hide them. But, if I was being honest with myself, there was no way that Mom hadn’t noticed. 

Now, I say, “at first,” because a couple weeks after my 18th birthday my Parents sat me down for a talk. 

The talk, involved them letting me know that they were a couple of kinky sex freaks, and that they’d just keeping it out of my line of sight my whole life. But, now that I was old enough, they didn’t want me to find out the wrong way. Like, if one of my buddies walked in on them at a sex party and told me how they’d joined in. 

I was assured that this was just an example, and, to their knowledge, hadn’t actually happened yet. But still… It was a hell of a visual! 

Later on, for some stupid reason, I confessed all of this to my friends. Naturally, they thought it was hot as hell. In fact, several of them spoke, at length, about how they needed to find out how to get into sex parties so that the example my parents gave could happen for real. 

I acted like they were just being assholes. But I wasn’t serious, and they could tell. I may never know if I told them all of that HOPING that they would describe their fantasies about my Mom, or just not realizing that they would. I thought it was the second one, but my reaction to picturing what they said as they came up with fantasies on the spot made me doubt my own intentions. 

After that, they got downright flirty with my Mom. What had been forbidden fruit, leading only to stolen glances and bullshit locker room talk was now much more out in the open. 

They complimented her, showed off in front of her, and flirted with her anyway that they could think of. And in response? Mom flirted right back!

She started dressing sexier around the house, and even more so when my buddies were over. They would shoot an almost sexual comment her way, and she would double down and make it very sexual before shooting me a wink and walking away to get back to whatever she’d been doing. This went on for about two months. And I swear, every time it started again it was like they were picking up where they left off. The sexual tension just kept building and building!

Then, one day Mom was walking through the living room wearing a little, white, one piece outfit. I’m not good with the names of clothes. But it was like a cross between a dress and… I don’t know. A sock? 

The top of it fit her like a corset. Hugging her gorgeous curves and ending immediately after her areola ended. Just barely enough coverage to not be porn. The bottom of it stretched down to her upper-thigh. Like, it barely covered anything, and it was squeezing her frame in a way that made all of us jealous of a piece of clothing. 

My work-friend, Chris, actually asked my Mom if she was wearing panties. At his question, Mom gave a shocked expression. With mock-surprise on her face, she said, “Christopher! Honestly. What a scandalous thing to ask your friends Mother.” Then, with a knowing grin, she lifted one foot and put it on the arm of the couch. And as she reached down to grab a hoodie and add it to the laundry basket, everyone got a very clear view of the most enticing pussy that we’d ever seen! Mom never broke eye contact with us. But once she’d tossed the hoodie into her laundry basket, she shot us a wink, put her foot back down, and continued going about her business. 

She was just about to leave the room when, probably emboldened by her response to Chris’s question, my best friend John stopped her in her tracks with a bold as hell statement. 

“I’d give anything to see those tits!” He practically yelled it. The comment was definitely directed at my Mom. Like, he wasn’t saying it as she left, he was saying it TO her. At that, Mom stopped, put her laundry basket down, and turned back towards us with a grin. She put a hand on her hip and looked us over. Then Mom said, “Well Johnny, in this dress, that is something that you earn. Not even my Husband gets to see my tits in this dress unless he can step up.” 

It was my buddy Scott who asked out loud how we could earn it. And for once, his response seemed to catch Mom off guard. Her ever-flirty grin faltered a bit, and she got real thoughtful. Which was odd, because it had seemed like the normal response to this set up. But she looked like she’d set that trap without realizing it, and now wasn’t sure how to proceed. 

After a minute of quietly thinking about it, Mom seemed to reach some kind of decision, and with a bit of a shrug, she turned her attention back to us. “I honestly wasn’t expecting to escalate things this way, but… You boys are all over 18. You are all good kids, and you are certainly all attractive enough.” That last comment got more than a couple of beaming smiles. 

“Yeah. Okay.” Mom said, seeming a little bit like she was trying to talk herself into something. Then she leveled her gaze at us and answered Scott’s question. “In this dress, you don’t deserve to see my tits unless you can knock them loose.” That raised a whole host of other questions. And it was Mike who actually raised his hand to ask the first one. But at the gesture, Mom laughed, and physically pushed his hand back down. “I think we’re past that Michael.”, she said with a grin. Then, without him needing to ask what the conditions were for “knocking them loose”, Mom beckoned us to follow her by curling her finger our way as she began to walk out of the living room and down the hallway. She led us to my Parents bedroom. There, she sat up on the bed, leaned way back onto her elbows, and proper her feet up on the bed. After a dramatic pause, she spread her legs out to the side, giving us all that killer view of her pussy once more. And, with a smile she asked, “Well? Anyone have a condom?” 

There was a mad fumble as everyone checked their wallets and their pockets. John, my best friend since forever, was the only one to come up with one. When he showed it to Mom, she invited him over to her. As he was standing between her legs, my other friend, Mike, apparently remembered that I kept a big box of them beside my bed since keeping them in your wallet was generally a bad idea. He was there and back in less than 60 seconds. Which, for just a second, had me a little ticked off. Like, he was going to fuck my Mom with MY condoms? My anger passed though when I realized that I actually thought that was kind of hot, and the sound of both John and my Mom moaning turned everyone’s head back to the bed. 

He was just bumping and prodding at her entrance. But when he actually got it in, everyone knew. Her loud moan, and his expression of pleasure so intense it was almost pain were practically a billboard announcing it. And if that wasn’t enough, Mom turned her head to the side (We were all at the foot of the bed still) and looked right at me. “Oh my god! I can’t believe your best friend has his cock in me!” 

A good thrust or two later, and with a lusty moan, Mom added, “And he’s REALLY spreading your Mother’s pussy too!” For a good two more minutes, everything was slow, but deeply intense. Loud moans and cries of pleasure resulted from every movement. John was clearly overwhelmed by what he was feeling, and Mom seemed super turned on by everything that was happening. But after those first few minutes, Mom held her hand up to John and gently chided him, “Uh uh,” she said, with in tandem with a little head shake. You aren’t ever going to see my tits if you keep up that pace. And that is what this is supposed to be all about. You can’t drag this out. Instead, you have to try to knock them out. Understand?” 

John nodded with a, “Yes Misses Smith.” And Mom got audible groans of pleasure from the friends who were watching when she answered back with, “Good boy.” The sounds drew Mom’s attention our way again, and she gave a quick up and down of all of us stuck watching before saying, “You boys should really take those pants off before you-”

But her words were cut off by a scream of pleasure as John took her words to heart and slammed his cock into her as hard as he could. Her massive tits rocked, but the little dress held on. So he slammed in again, and again. Mom’s scream of pleasure filled the room and raised the temperature another 100 degrees or so. The longer he went at it, the faster he went at it. He was fucking her faster and faster, and Mom was clearly loving it. Muttering “yes yes yes,” and giving him words of encouragement like, “Just like that!” 

It didn’t take too long at that pace for John to say he was going to cum soon. When he did, Mom lifted her head to say something to him. Then she paused, set her elbows down, and turned her face towards us instead. “Did you hear that boys?” She said as her moans, and the hard, pounding beat of the sex interrupted her every other word. “Little Johnny is about to cum inside Steven’s Mom!” 

That was it for John, and he started screaming out an orgasm through clenched teeth as he gripped my Mother’s hips and pounded her as hard as he could. When he was done, both Mom and my Best Friend were panting for breath. After a minute or two of them just trying to breath, John pulled out and dropped a very full condom into the wastebasket beside my Parent’s bed. 

Mom just laid back and breathed for another full minute. Then she got up on her elbows again, and looked pointedly from us, to her dress. Which, by some miracle of science, was still sitting where it was supposed to. Mom grinned sexily, and, glancing our way she asked, “Anyone else wanna try?” 

Everyone said yes, raised their hand, or both. But it was Mike who pulled a condom out of the box he was still holding. When he set it down, everyone grabbed for 1 or two for themselves. But Mike was already marked by my Mom’s gaze as the clear winner. He took position just like John had before him, and Mom quirked an eyebrow to ask him where he got the box of condoms. When answered that he’d gotten them from my room, Mom’s surprise was clear as she looked over at me. 

“Your supplying your friends with condom’s so they can fuck me?” Then she gave a little groan of pleasure as Mike started working his way into her. “Oh my god.” Mom said. “That’s so fucking filthy! I love it!” 

Mom then looked back to Mike. “How does that pussy feel Michael?” But when he started to answer, she cut him off. “Not to me sweetie. Tell Steven. My Son clearly want’s see all his buddies fuck his Mom. So it’s only right if we include him.” 

Mike, for his part. Only hesitated for a second. And, honestly, it is hard to fault him. A beautiful goddess of a woman was giving him the opportunity of a lifetime, and it wasn’t exactly a big ask. So, after a small pause, he turned to me and told me, “Oh my god dude. Your Mom’s pussy is SO fucking tight.” Then a few thrusts later, “It’s seriously the tightest pussy I’ve ever felt. It feels so good!” 

He got a few more thrusts in before Mom locked eyes with him and told him, “That’s enough foreplay now. You are here for a reason remember? Knock those titties free sweetie.” At Mom’s words, Mike started to really pound her. Like, it wasn’t as fast as John had been going, but it legitimately seemed to be at least twice as hard. 

Mom was screaming with pleasure before he was even on the third thrust. She cried out, “Slam it! Fucking slam it!” It didn’t last that long, but the whole thing was extremely intense. Every thrust got a moan or a scream out of both of them as Mike gave it to my Mom as hard as he could. When he said he was going to cum, Mom was lost, mid orgasm. And just dragged out the word “YES!”, as his pounding thrusts continuously interrupted her. When he finished, his hips went into a blur as he started going at it as fast as he could. A total change of pace from everything leading up to that moment. When he started cumming, he was the one screaming, as Mom had just finished her own orgasm. So she lifted her head, and in a very Motherly tone, she encouraged him. “That’s it. That’s it baby. Give me that cum. Give Mrs. Smith all of that cum. Good boy honey. Yes.” She talked him through his orgasm, and though the dialogue was tame as hell, there was still something weirdly hot about it. 

When he was truly finished, he collapsed on her. And Mom stroked his hair, and told him how great he’d done. That went on for several minutes. But as desperate as Chris and Scott were to take their turn, they didn’t dare interrupt the moment. 

When Mike finally got up, he added his condom to the trash with a noisy plop. And then Mom popped up on her elbows again. Because again, her dress, evil and powerful, was still hiding her tits. If only just barely. Mom looked at us, a wicked gleam in her eyes as she smiled in anticipation. Then we all saw her get an idea. And from the curl of her lips, a wicked idea at that. 

“Now, I’m sure you both want to be next, and you both want to feel my pussy. But surely at least one of you has fantasized about my mouth…” 

They both were quick to agree. But Mom cut in to propose something different. “Well,” she said. “Since my Son is much more into this than I thought he would be. What do you two say to giving him a show?” 

There were gulps as both of my friends nodded in agreement. This drew a smile from the very lovely lips that my Mother was apparently offering. 

She didn’t say anything else. She didn’t tell them her idea, or explain in any way. She simply arched her back, opened her mouth, and waited. There was a few seconds of quick and quiet conversation between Chris and Scott. Then Chris went over to my Mother’s spread and waiting legs, while Scott got up onto the bed with Mom and moved in towards her mouth. Mom took Scott’s dick in her hand. Then she looked my way and asked, “Ready to watch Mommy act like a whore?” I gulped and nodded, and if anything, my own dick somehow got harder. The reaction made Mom smile, and the smile itself would have been enough to make almost any man hard at the sight of it. It was so full of sinful promises. 

Then Mom looked up at Scott and said, “I don’t think we’ll need this now.” And she began to roll the condom off of him. When his cock was bare again, Mom glanced my way, and kept eye-contact as she arched her body, parted her lips, and with a moan, took Scott’s cock into her mouth. 

The guys had a hard time finding a rhythm at first. And eventually, Mom had Scott get off the bed, and Chris get onto it, so that she could hang her head back over the other side and, in her words, open up her throat for Scott’s cock.

What happened after that was the hottest thing that I’d ever seen. It wasn’t just the sight of it. Though, that was incredible. My Mother’s body squirming and arching with pleasure. Her big tits shaking. The sight of her lovely lips moving up and down on a dick, and her throat bulging during all the times that she took him deep and held him there. 

All of that was amazing. But the sounds were equally incredible. There was no eye contact, or quippy teasing this time. It was just moaning, slurping, gasping, and crying out in pleasure. It was my MOM’s voice. The most familiar voice in the world! As she groaned, and whimpered, and made the most obscene blowjob noises. 

They lasted longer this time. Probably in part because Mom wasn’t able to verbally demand that they fuck her harder. But eventually, Chris told all of us that he was going to cum soon. When he did, Mom gave Scott a little touch on his stomach that had him stepping back. And as he pulled out of her throat, and she gasped for air, she was also working her fingers on the top of her dress. Apparently there were clasps hidden in the soft white folds. The moment she freed him, the dress gave way, and her big, beautiful tits finally popped free. 

Once they were out, we all groaned in response, and Mom did her best to scoot her dress down a bit. Chris gave another warning that he was close, and Mom pushed her big tits together and told him to, “Fuck these instead.” His expression was one of shock and disbelief. But Mom just nodded, smiled, and told him, “Quickly!” 

He didn’t waste any time. He pulled out, ripped his condom off, and made his way up to my Mother’s very large breasts. But he wasn’t in them for more than a few quick seconds, when he cried out “Oh shit!”, and we all knew that he was cumming. Mom moved her tits to help stroke him off in time with his thrusts, as he came in between her tits, out onto her chests, and he even got  the bottom of her chin with a blast. 

Before Chris was fully finished, Scott said that he was going to cum too. And, yeah. It was a hell of a sight. Especially after countless years of all of fantasizing about what Chris was currently doing. Mom gave the head of Chris’s dick a long lick that turned her head up towards Scott. At which point she looked him in the eyes and said, “Cum all over my face baby. I want your cum, all over my face!” 

For the next minute or two, both men screamed, and came all over my Mother. And with each splash of hot cum, my Mom would moan and beg for more! 

When they were finally done, Chris got down off the bed, and he and Scott both went off to the bathroom to clean up. As my Mom sat up on the bed and turned to face the rest of us standing in the doorway, she looked like she’d just come fresh from a porno shoot. There was cum all over my Mother’s beautiful face, and it was on her tits, and running down her chest as well. Mom let us take in the sight of her, and as we did, Mike and John were already stroking fresh hard-ons. I, on the other hand, didn’t dare touch my dick for fear that it would go off. Instead I just stared at that incredibly hot sight and tried to burn it into my memory for later. 

Cum covered, Mom shot me one last, sexy wink. Then she announced that she needed to shower and change. We all watched her walk away, as her body was still gorgeous, and her dress had been reduced to a belt at this point. 

After she was gone, everyone got cleaned up. I had the thought that I needed to find an excuse to kick everyone out of the house because if I didn’t cum soon I was going to lose my fucking mind. When we got to the living room, John, who’d known me so long he was practically a Brother, fired up one of my gaming consoles and just started playing a fighting game. 

It normalized things. Pretty soon Scott picked up the other controller and challenged him. Then Mike called winner. And we barely even noticed the twenty minutes that passed before Mom came back into the room. He hair was still wet, but she was letting it hang and make her t-shirt damp instead of putting it up in a towel like she normally did. Her massive tits were on display in the men’s plain white tee that she was wearing, and the only other thing she was wearing was a tiny black skirt. 

She smiled when she saw us all gaming and giving each other crap like nothing had changed. Then she focused her gaze on me. She walked over to me, and with a word had Mike move over so she could get on the couch. But when she did, she did so by straddling me. I managed a confused “Mom!?”, but she ignored it as she pulled my pants and boxers down so she could free my cock. Once she had, she took my face in her hands, turned it to the side, and began to devour my neck. 

Her tongue and her lips felt electric and exciting. In no time I was moaning and rock hard. And right about the time that I was worrying about her feeling my hard-on, she reached down, grabbed it, and guided it into her pussy. 

When I finally sank in, right down to the hilt, it was the most incredible, full, fulfilled, and amazing feeling of my life. It was singular, and incredible. And Mom apparently felt the same since after a loud cry of pleasure, we both just sat there, panted, moaned, and held one another for what seemed like a good five minutes. 

Mom went to speak then, but as she moved, we both cried out, and soon she was gripping my head, and moaning and panting again. 

A few minutes more of that, and Mom had it under control. She looked at me and started to say, “Your Father…” But she stopped her sentence there. And after a moment, she turned her head so that she could address the other guys there as well. “My Husband just texted to let me know that he won’t be home tonight. His work thing ran over, and he is just going to grab a hotel. So…”

She began. “I was thinking that, if you boys wanted to stay the night, we could spend it together. Honestly, I’m really liking this. And I want more. So, if any of you want to stay. Then I figured I could make us all a big dinner. We could cuddle up and watch a movie together. And then, well…” And at that, she turned her eyes back towards mine. “Then I was thinking we could all play a game of, let’s gangbang Steven’s Mommy.” 

At her words, I bucked my hips up. Hard! Mom cried out, but her moan turned into a smile soon after. She was grinning at me. Clearly pleased with how I’d responded. She kissed me then. 

After another few moments of unbelievable pleasure, and still, just from being inside of her, I finally realized that I wasn’t wearing a condom. I was almost panicked when I told her, but she just shushed me and ran her fingers through my hair as she gently explained, “Family doesn’t need to. It’s okay.” 

At her words, John cut in with, “I mean. I’m kind of like family.” Mom laughed, but soon every other friend, even Chris, who’d I’d met at work and known for like a year and a half had also chimed in that, they too, were practically family. 

But Mom never took her eyes off of me. She just sat in my lap, and with intimate eye contact, gently rolled her hips and drew an intense moan from both of us. Then, after a second, she said, “That’s up to you Son.” I was so lost in the euphoria of what I was experiencing, I honestly had no idea what she was talking about. I think I said something like, “What?” In a half-daze. 

But Mom, in this wicked little whisper asked, “Are they just like family?” I bucked again when I realized what she meant. But, I’m pretty sure Mom knew my answer before I did. Because she began to roll her hips again. Slowly. Sensuously. But from that moment forward, she never stopped again. Her pace and intensity only grew as the moment got increasingly intense. 

“I didn’t plan on any of this,” Mom said. Moaning softly. “But I like it baby. Mommy likes it a lot! So just how hardcore do you want this new relationship with Mommy to be?” She asked. “Do we limit it to two at a time?”

“Three?” 

“Five?” 

Then she leaned into my ear and whispered, “Do you need to get our your phone and call up some more of your little buddies so you can watch me getting fucked by 10 of them?” 

I cried out at her filthy words. But I knew she meant them. Every last word. And she clearly wasn’t the only one who was liking this. 

Mom assured me, “Condoms are perfectly reasonable, sweetie.” But I could hear the grin as she continued with, “But if you really want to see me acting like a whore…” 

Then Mom tossed all that long gorgeous hair of hers back over one shoulder and finished her thought with, “Then maybe we get rid of them. How’s that sound, huh? Watching your Friends jamming their cocks into your Mother raw. Seeing them drag them along Mommy’s face before shoving them into my mouth. Does that sound good baby?”

And, as good as that dialogue. No… As those promises, were. What made me lose it, was when she pressed her tits into me, and, in an unfiltered moment, she  whimpered into my ear, “Oh god baby! Your cock feels so good in Mommy!” 

At that, I lost it. Mom felt it coming and began me to ride me hard. 

Soon, we were both screaming and cumming, and losing our minds as we held onto to one another and had absolutely incredible orgasms!

When it was done, we were panting, hugging one another, and in a state of bliss. I don’t know how long we sat like that before one of the guys just said, “Damn…”

At his comment, Mom and I both laughed. It was not unlike being giddy. 

Later on, Mom got dressed again. This time for real. Her outfit was still sexy, but if someone knocked on the door, she could have answered it without getting the cops called on her. Then, true to her word, we did dinner, then a movie, and then my Mom. 

It was the best fucking night of my life. And according to Mom, it was only the beginning.

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