Pillory Slut

 

Pillory Slut

My Son had been asking after “the lifestyle” for years. His Father and I had always been very 

open and honest with him when it came to sex. That is probably why when he was halfway 

through high school, he’d asked enough questions about kinky sex and kinky lifestyles that he put 

two and two together, and finally worked up the courage to ask his Dad and I how we always 

managed to have answers immediately available no matter how kinky the question.

So, we told him. Mommy and Daddy were swingers, and fans of roleplay, bondage, and every 

other thing he’d ever asked after. We knew, because we knew. After that, the questions came a 

lot faster, and got a lot kinkier. But while his Dad ran into some trouble explaining certain 

subjects, I tended to have a lot of fun with it.

I liked answering his questions in ways that made him squirm. I’ll admit it. For example, when he 

first asked me if girls really enjoyed being made airtight, I gave him this taken aback look, put my 

hand to my chest and said something like, “Sweetheart… the only way I could possibly know the 

answer to that would be if I’d done it myself. So, to be clear, are you asking your own Mother if 

she’s had a cock in her pussy and in her ass at the same time, and be so greedy for more, that I 

asked another guy to come over and fill up my mouth with a THIRD cock?”

Watching him squirm, and turn red, and try to decide if he would be in trouble for answering 

honestly was always equal parts fun, and a little hot. But, if he worked up the courage, I always 

made sure to answer him in a way that felt like a reward. It usually involved a confession of 

something that I had personally done, and a little moan to go with it.

Of course, being honest with him about sex, kink, how they worked, how they should work, and 

what he should and definitely should not do; was all well and good. But it wasn’t like I was going 

to lay a finger on him, or let anyone else do so, until he was at least 18. That said, two years can 

go by SO fast…

Next thing I knew, my baby boy was graduating high school, having his 18th birthday, and 

begging to come along on his first little weekend getaway. Now, his Dad wasn’t comfortable with 

it at first. But I explained to his Father that we’d raised someone who could figure out how to go 

whether we invited him along or not, so, better to exercise what little control we had. But, he was 

still not comfortable with it, so, I agreed to take our Son on a solo trip for his first time during one 

of the weekends his Father would be out of state on business, and let him know how it went.

A few weeks later, my Son and I were checking into a hotel that one of my favorite kink clubs had 

booked for the whole weekend. The whole hotel was rented out and ours to play with. We had to 

play nice around conference rooms that had public facing windows; but aside from that, the 

whole building was one giant, kinky playground.

Meeting rooms filled with stockades, cages, crosses, and rope set-ups of every kind had their 

doors wide open and barely dressed (or not dressed) people of every walk of life mingled, 

played, kissed, sucked, and fucked all over the hotel. In fairness, the public areas were mostly 

used for play, and not just raw sex, but nothing was off limits.

So, I gave my Son the tour, showed him all the different devices, and explained what they were 

for. Mind you, at least one of every kind was already in use right before his eyes, so the 

explanation was a touch redundant. But for the most part, it was fun! I got to bring this fresh, new 

man into the community and show him around like a trophy, an 18-year-old no less! I’ll admit, 

Son or not, I was feeling pretty good with a guy that young hanging on my arm and my words as I 

showed him around. Until we got to the first device that wasn’t in use.

There was a stockade (also called a pillory, or stocks), but it wasn’t in use. My Son of course had 

a ton of questions, and I explained with no small amount of joy or amusement how the device 

was used for a person to be locked in place, head still and facing forward, hands bound and 

helpless, and legs spread out and set behind them so that the person in the pillory was on 

display and ready “for use”.

Then my Son said something that gave me lovely little tingle. He was a little shy about it, but he 

asked, and that took courage. Three little words, but I was SO proud. He said, “can I see?”, and 

we both knew there was only way to show him. In reply, I didn’t say a word, I simply gave him a 

sinful little smile of approval. Then I applied some fresh lipstick, set my purse aside, and let most 

of my clothes join my purse in the corner. I needed his help here and there, but when all was said 

and done, I was bent over at the waste, bound up, and staring him in the crotch.

I was still wearing my knee-high “fuck me” boots, but not much else. From my very vulnerable 

new position, I cast my eyes up at my Son and asked him if he was enjoying the view. He said 

yes… which was good, since a no would have been a pretty stupid lie. I was, after all, having to 

make an effort not to be staring at his erection. So, my Son clearly enjoying himself, I went ahead 

and re-explained all the things that could be done to a person in my position with the help of the 

pillory/stockade.

It was right around that a stranger interrupted us. Not necessarily rudely, after all, you never knew 

if you could join in someone else’s play if you didn’t ask; but with my Son right there, it definitely 

felt a little off. A male I didn’t personally know, but who I’d seen around enough to know that they 

liked to play rough (which I liked), heard us talking and came up to us. When he saw me trying to 

look at him, the little punk stepped behind me, just so I couldn’t! I’d have given him the dirty look 

he deserved... if I wasn’t bound up like the village's “free use” whore. As it was, all I could do was 

stand there with my legs spread and do my best to look my Son in the eye. Thankfully, my Son 

saw me struggling a bit and took a step back so that he not only got the full view of me, (I may 

have wiggled my ass a little when I realized this; don’t judge) but also allowed me to look him in 

the face instead of just staring at the bulge in his pants. Not that I’d been complaining…

The man behind me had obviously heard us talking, because he started by asking my Son, very 

politely, I will say, if it was his first time here. Then, when my Son admitted that it was, he started 

to genuinely give him a rundown of the rules of play, same as I had been about to do. But, unlike 

I’d been planning, he ended his run down by asking for sex. “

So,” he told my Son. “Even though you have her on display like this, no one can actually touch 

her without your permission, since you two are obviously playing together. Many won’t even ask. 

But since I see how you have her, and I know you are new... I thought that maybe asking if you 

want to see her get fucked, might actually be the polite thing to do.”

I could hear his smug smirk without seeing it. And, I had to be honest, all this talk about me being 

for free use, and being put on display, and how slutty I looked, definitely had me wet and 

squirming. But I was all too happy to explain to him why his little play for my body wasn’t going to 

Work.

“Nice try buddy,” I said, giving my Son a warm smile. “But there is just one little problem. This 

isn’t just his first time. This is his first time, and his MOM is the one who brought him.” I tried to 

look over my shoulder at him again, but, yup, still shackled in a pillory, so, that didn’t happen. “So 

he’s not about to say yes to you, or anyone else, unless he wants to see his own Mother get 

fucked.” I gave a little laugh then, and took a sec to shoot my Kid a wink.

There was a brief pause, and I heard the guy behind me unzip. Like, he did that really deliberate 

unzip, where you pull down on the jeans, because you WANT to be heard. I almost legitimately 

gasped in shock. He wouldn’t dare touch me without my play partners permission! But, there 

was a pause, another pause, and some movement, and I knew what he was going for when I 

heard from behind and to the side as he ignored me, and addressed my Son again.

“Well hell. That sounds even hotter to me! How about you big man? Wanna see what kind of 

face your Mom makes when I put this in her?” I couldn’t hear it really, but I swear I could hear him 

waggle it. I was ready to shake my head, and give my Son a “do you believe this guy?!” look, 

but… When I looked back at him, it was just in time to see him give the man behind me the 

smallest of nods.

But… that was permission. That would totally count as permission! I started to warn my Son 

about what he had accidentally done. “Wait. Sweetie. If you give a nod that means that-”. But 

then mid-sentence, the cock that my Son and the stranger had just been discussing, pushed into 

me from behind!

My words quickly twisted into a moan of pleasure that I didn’t mean to give, as the strangers dick, 

rather easily, slipped into my soaking wet pussy. I couldn’t help it! I was bound up like a whore 

while a stranger debated with my Son over the price of my use! I mean, obviously I didn’t want to 

traumatize my kid, but at the same time, it was kind of fucking hot the way everyone was talking 

about me.

I tried again, “Sweetie, when you nod it-”, but right at that moment, the man behind me smacked 

my ass cheeks and pushed back into me again. He was drawing it out, all the way to the tip, nice 

and slow, and then waiting for me. But shortly after I tried talking again, he would shove his cock 

right back into me, and make me scream in pleasure all over again. It seriously didn’t help that I 

knew my Son was watching. I mean, I know it should have been just what I needed to shock me 

out of it, but instead it was seriously fucking turning me on. I don’t know why! It was just that, the 

idea that this man was forcing me to reveal what a cock-hungry slut I was in front of my own Son 

was just… hot! I was SO warm. I was practically panting with the heat of it. I felt like I’d just 

discovered a hot new fantasy, and the moment I had, someone started fucking me while acting it 

out. Because that was exactly what was happening!!!

I started to try to explain the situation to my Son again, but this time, instead of shoving it back in, 

the stranger behind me grabbed my hips like he was going to double down; but instead, he 

began to slowly inch it back into me, and spread me open nice and slow. And just, FUCK! I was 

already so turned on, and clenching so tight, that it felt INCREDIBLE. I actually said, out loud, to 

my own Son, “Sweetie, when you nod, it… oh fuck. Oh fuck fuck fuck! He’s pushing it back in 

honey! Oh fuck! He’s got his cock inside your Mother’s pussy, and he’s spreading me open so 

fucking good!”

And once again, if I could have slapped my hand over my own mouth in shock, I would have! 

What was I thinking! What was I saying! But as I gritted my teeth in between moans, I heard a 

voice in front of me say, “Does it feel good? Do you like it?”

And… Oh! My! God!!! Was my Son fucking into this!?!

I was practically holding my breath with anticipation now. I opened my eyes, and, very slowly, 

lifted my head to REALLY look at my Son for the first time since this whole thing started. The 

very first thing I noticed, was that he was even harder than before! He was hard as a rock. He 

had moved a little closer to me again, and the outline of his hard-on just, SO CLOSE. He was 

displaying a very impressive bulge, that may have made my mouth water a bit. But as I strained 

my neck to look up at his face, I saw that his face was as red as mine, and I was beginning to 

think it wasn’t because I was traumatizing him; but rather because I was turning him on.

I swallowed hard at the implication that I wasn’t the only one suddenly in the middle of a very real, 

very intense incest fantasy. Then, testing the idea. I maintained eye contact with my Son while 

also giving my mystery man a teasing clench. He responded like I knew he would and gave my 

pussy a hard slam to “teach me a lesson”. When he did, I let my face show how much I loved it. I 

didn’t try to suppress my moan, instead I gave into it completely. Then, with an appropriately 

slutty tone of voice, I told my Son right to his face, “Oh fuck yes! I love the feeling of-”, and I 

almost said, ‘that big cock fucking me’, but as I realized how depraved and public this whole 

thing felt, I took a chance, and corrected myself in the moment to, “...big cocks inside of me.”

And as I made my carefully worded slutty confession, my Son’s face told me everything I needed 

to know. He looked like my words alone were going to make him cum. He was getting to see his 

Mother’s “O” face, and it wasn’t just, not embarrassing, it was turning him on; big time! And 

dammit… that just turned me on even more!

“How about you slugger?” I asked, using a nickname I’d used for my Son since long before he 

was in high school. “Do you like watching me moan? Hmm? Are you enjoying watching me get 

used like this in front of a room full of people? Are you glad you told some random, big-dicked 

stranger, that he could shove his cock inside your Mommy?”

My Son groaned in pleasure, and so did the guy behind me. The stranger in question was no 

longer able to just tease me, he was quickly adopting a steady pace. And the more I talked, the 

more all three of us moaned, and his pace increased. In fact, as I teased my Son about what 

he’d arranged to happen to his Mother, we were drawing a bit of a crowd.

My Son was rubbing the outline of his cock through his clothes, and I could tell by his face, and 

his breathing, and his moans, that he would absolutely cum that way if I let him. So I told him that 

I wanted to hear him admit it. And when he looked at me confused, I clarified, loudly. “I want you 

to take your cock out, and stroke it in your Mother’s face. And I want to hear you to say it. I want 

you to admit that you wanted this. Tell me! Tell me your jerking off to Mommy being used like a 

whore in front of you!”

He stopped rubbing his pants, and grabbed his dick tightly as he hissed in through his teeth. I 

think I almost made him cum. But after a minute, he nodded… which wasn’t good enough. I was 

really getting pounded now, and it was hard to talk through the moans, squeals, and screams; 

but I managed to insist that he actually say it one last time. And god help me, I came HARD 

when he took his cock out, pointed it right at me, and said, “I love watching you be a whore 

Mom!”

My cumming set off the guy who was fucking me, who pulled out and began to shoot his load all 

over my ass. I had a moment where I thought I was about to get a face full of hot cum from my 

18-year-old Son, and just the thought of it made me quiver and set off a second orgasm 

immediately after the first. But, that hot splash of cum to the face never came; and after my head 

cleared enough for me to think properly, I saw why. My Son was right in front of me, his dick 

throbbing in his hands. But his eyes were closed, and I could tell by his face that he was trying 

desperately not to cum.

I got it. I mean, he didn’t want it to end, and unlike his Mom, he couldn’t just keep cumming, and 

going again. So, I was nice, and I gave him a minute to calm down, before I greeted his opening 

eyes with a satisfied smile, and I assured him that I was having fun. “How about you slugger?” I 

asked, glancing at his cock, and making a point of licking my lips. “You having fun?”

He nodded, and something about the way he did it was just too cute. He was lost in, apparently, 

a really big fantasy; but his Mom was watching him do it. So, if your Mom IS your fantasy… is 

that still stressful? I wasn’t sure, but I couldn’t just stand there bound up. So I figured it was time 

to see how far his fantasy went. After all, we HAD drawn a bit of a crowd with our “mom/son 

play”.

Now, not many boys my Son’s age were at the event. They tended to be too immature to get

 invited. But I knew of two who were only a few years older than him that were regulars. So I took 

a chance, and called them both by name to see if they were around. And, wouldn’t you know it, 

they both came running.

I had them introduce themselves to my Son, and I explained to him that these two were regulars, 

but they were also still in college. “My Son is about to go to college, and, he and I just learned that 

he likes seeing his Mom at her sluttiest. So, I was wondering if you boys could tell us what we 

might expect when I visit him next year… What do you two think? Would a couple of college 

boys like yourselves be interested in just… REALLY Going to Town on someone’s Mom while 

they watched?”

All three boys gulped, but the two college boys were already nodding and touching themselves 

through their clothes as they took a few steps back to drink in the sight of me and my current 

predicament. Both of them actually said “Yes Mam”, and, after having a wicked thought, I asked 

them to call me, Misses, and my last initial… since that was what all of my Son’s friends called 

me. I then told them that my Son was fully in charge of the scene, so it was up to him what he 

wanted to see.

“How about it slugger?” I asked. “Would you like a little preview of what it might look like if 

Mommy visited you at your dorm next year, and you asked her to play fuck toy to two of your new 

college friends?”

He groaned in pleasure, and started stroking himself again. But his tone was practically begging 

when he finally managed a yes, and directed his, “two new friends”, to go ahead and get started. 

As they excitedly got into position, I advised my Son that his view was about to be blocked, and 

let him know he might want to move to the side of me.

Then, just as I felt the head of the first cock begin to bump at, and search my entrance; and the 

second one sprung up in front of me, I made one last request while I still could. “Boys… before 

we get started, I need you to know that this is actually my Son’s first time here. So, would two be 

dears, and, first of all, take a second to thank him for, basically whoring me out to you. And 

second of all, please remember to take the time to let him know what you are doing to me, and 

how it feels while you are doing it. Please? For me?”

My Son had to sit down, he was so overwhelmed when the two college boys took turns thanking 

him. The first one quoted me almost verbatim, saying, “Thanks for whoring your Mom out to us. 

This is going to be awesome!”. The second one put his own little flourish on it when he said, 

“Yeah man. I think it’s really cool that you have such a sexy Mom, and you're gonna let your frat 

brother’s double-team her when she visits you at college.”

I may have thought they were a little awkward at setting up the scene, but they surprised me with 

how verbal they were once they got going. The one behind me immediately told my Son how hot 

and tight my pussy felt, and explained to him in some detail when he was pushing into me, and 

when he was about to, “really give it” to me. At one point, he invited my Son to come stand by 

him so he could watch him spreading my cunt open with cock. Which, made me cum almost 

immediately, even if my Son did manage to hold off a bit longer.

The one in front of me did just as good. He fucked my mouth, and explained how good it felt. He 

explained when he was going to push all the way into my throat, and he asked my Son if he 

wanted to him to make it so he could see his Mom’s cheek stuffed and bulging with the head of a 

cock. He also did me the courtesy of complimenting my cock-sucking skills multiple times, and 

even told my Son that his Mother was giving him the best blowjob of his life, and implied that I 

could only be so good at it if I’d had LOTS of experience. Which, I of course used as an 

opportunity to give my kid a very suggestive wink.

They honestly did a great job fucking me from both ends, and I only wished I’d been on the floor 

so I could have shown them how much better it was when my hands were free to touch them 

back. But, just when I thought it couldn’t get any better, the kid in front of me not only said that he 

was going to cum, but he actually turned to my Son and asked him if he wanted him to make me 

swallow his load, or if he’d rather see his Mother’s face covered in cum.

Once again, it was so fucking hot that I clenched up and started to cum myself. That set the boy 

behind me off, and, following his friend's example, he asked if he should pull out, or cum inside 

me! I didn’t even know if he was wearing a condom! I was doing my best to glance at my Son, 

and find out what he was going to say. He was quickly running out of time to answer, and I wasn’t 

exactly going to get any input while I was locked in a stockade and getting my face fucked.

The tension was building insanely fast, and everyone was fucking, and stroking, and moaning, 

and building to the next orgasm. Then, FINALLY, my Son stood up and practically ran over to me 

with his cock in hand, blurting out, “Cum on her face! I want to see her face covered in cum!” 

The boy in front of me roared, and pulled out of my mouth, frantically jerking his cock as fast and 

hard as he could. I had time to moan out that I wanted my Son to join him. He hesitated for a 

split-second, but I my tone was a begging scream as I repeated that I wanted him to “cum on 

Mommy’s face!” and that seemed to do the trick. Next thing I knew, I had two handsome young 

men jerking off onto my face, as I heard a building cry behind me, and I knew it was basically too 

late to really make a decision. So I gave the one fucking me my slutty blessing, and told him to 

blow his fucking load inside of me!

We were all screaming, and moaning, and cumming. When it was all done, I must have looked 

quite the site. My Son was looking at me with total awe as my face, tits, and hair, dripped with the 

combined loads of two young studs with exceedingly full balls. Behind me, my other, most recent 

lover, collapsed onto his butt and sat on the floor behind me as his cum dripped out of my pussy 

and ran down my thigh.

My whole body was shaking with equal parts fatigue and pleasure. I was loving every second of 

it, but I also needed to be let out of the literal ancient torture device that I’d started in. So, as not 

awkwardly as I could, I asked my Son to get me out of the stockade, so I could rest after all the 

guys he’d had fuck me.

We ended up, just the two of us, back at our room so I could shower. Because, I was an 

absolute mess. Mind you, I could tell by the glancing my Son kept casting my way as we walked 

back to the room that he very much approved of the mess that he and that other boy had made 

of his Mother. But, as much as I enjoyed those looks, I still also needed a shower.

When I was done, I took us out to lunch, and I did my best to make the rest of the day as normal 

as possible. I figured we’d had enough excitement for our first day. Later that night, my Son 

started freaking out and asking if he’d messed up, and if I was mad at him or anything, and I was 

careful to assure him that I had enjoyed everything, and that he had done nothing wrong. Of 

course, the cute wore off a little (just a little though), when not 5 minutes later he asked me, oh 

so nonchalantly, if I’d been serious about letting him see me getting taken again if I visited him at 

college.

At that point, it was late, and the lights were out. But frankly, he was dying to know if I was 

serious, or he was calling my bluff; and honestly, I was a little curious about the reverse. So, I got 

out of bed, grabbed his cell phone from his charging station, and tossed it to him. “Call them”, I 

said. At first, he “Mom?”’d me, and acted confused. But I doubled down as I clarified. “There is no 

way that your friends are asleep at 11pm on a weekend. So, pick a handful, and call them. We 

aren’t that far from home, and they are all driving by now. So ask them if any of them would like 

to drive here, meet you at our hotel room, and go a few rounds with your Mom while you watch.”

He was stunned. And I wasn’t sure if we’d found his limits. After all, it was one thing to do 

something kinky, and play out a fantasy. It was a whole other thing to be able to play video games 

with your friends, and know for a fact that they really had fucked your Mom, and blown their loads 

on her face and tits. But, of all the surprising things he could have said, the next words out of his 

mouth, truly, genuinely, made me smile.

“A handful?” He asked. “So like… more than just two?”

The little scamp! I wanted to chastise him, but what he said was hot, and I couldn’t stop grinning

 from ear to ear at the audacity. So, feeling like I was calling his bluff a bit, I retorted, “I never said 

my limit was two. Just remember, more friends means more consequences the next time you 

want to hang out with your friends, or invite them over for a sleepover. So, knowing that, how 

many do you want to call?”

You would not have thought that you could fit 10 horny teenagers, plus me, plus my Son, into one 

little hotel room. But it turns out, you can. Oh, they were shy enough… at first. Still calling me 

Misses (my last initial), and being all polite and coy. But I’d heard what my Son had offered them 

over the phone, and I knew how fast they’d driven to get there. So, I wasn’t at all surprised when I 

took out the bottle of baby oil, pulled my shirt up over my head, and began oiling up my tits when 

all pretense of “we would never” went out the window.

That night, my Son didn’t just play out a fantasy, or get to pretend at a fetish. No, his actual, literal 

fantasy happened right in front of him, and later on, right on top of him.  He got to order around 

his real Mother as I played the whore for his friends, and they stuffed me full of hot young cocks 

from every angle.

In our room, we weren’t in the “convention area” anymore, so I let him take pictures and a few 

video’s as his Mom slurped, sucked, titfucked, jerked off, and fucked every last one of his little 

high school buddies. I changed outfits a few times. After all, I’d brought plenty of naughty outfits, 

and this was a great opportunity to fulfill some fantasies and show them off.

If anything, the only problem was that they were being too sweet. So a few hours in, when they 

were recharging, I had one of them go get his wallet and fish me out a 5 dollar bill. Then I had the 

rest of them grab some loose cash from their wallets as well.

The first one wasn’t the only one who seemed confused by it, so I took the money from him, and 

gently explained that, they were doing great, but they were missing the point a bit. Their friend 

didn’t invite them to a hotel room to be polite to his very sexy, and very generous Mom. At that, I 

let the silence hang in the air for a second as I started tucking fistfuls of loose money into my 

purse, and I finished explaining. “Your friend invited you here, to FUCK, his WHORE Mother.” I 

grabbed the cock of the boy nearest to me and added, “To shove your cock into my WHORE 

mouth, and let him know that his Mom was worth every penny, because I’m sucking your cocks 

SO good! Now…” I said, leading my Son to the bed, laying him out beneath me, and squishing 

his cock under my oiled-up tits as I pressed my chest down into him, and raised my ass up into 

the air. “... if you boys are done resting. I need you to show my Son here, and I mean REALLY 

show him, just how much of a whore his Mommy his! So, if you think you can tell your, let’s be 

honest, BEST friend, after tonight, how tight his Mother’s asshole feels, and how hard you and 

NINE of his other buddies are fucking her… Then I think you just might be ready for round two.”

They uh… they got it then. My Son came twice more underneath me as his friends pinned me 

against him, and pounded me like the dirty little slut that I was. Then he came a third time later 

on, when I saw he was hard again, and finally got to sit on him. But, as tender moments go, him 

getting to feel his own Mother’s pussy for the first time was a pretty brief one. Since, per my 

instructions, her friends weren’t about it let anything that happened to me that night be pure. No 

sooner was his cock in my pussy then four boys stood up on the bed and pointed their cocks at 

my face. So I rode my Son, while he looked up and watched his Mom greedily suck and stroke 

four of friends in a little mini-blowbang.

He watched them gangbang his Mommy, and, just like me, he loved it.

Oh, and, in case you were wondering... It turns out I WAS serious about what the possibilities 

were when I visited him at college next year. And frankly, I can’t wait.