Busty Naïve Punishment

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"I...I do have this," the girl says in a soft, embarrassed tone. She then walks off to the side, where her bed is located. She kneels down and pulls out a shoebox from underneath her bed. I smile a brief smirk at this as it's so like an innocent girl to keep something there.

She opens the box and digs in it for a moment, then lifts something out of it. After returning the box to under her bed, she returns to center screen with what she grabbed in her hand. She holds it out so it dangles on one finger, and I nearly cum in my pants.

It's handcuffs. Silver, shiny handcuffs. And real ones too, not the type with the latch that you can get yourself out of them. These are like cop cuffs, where only a key will open them.

"I...I had the same thought, which is why I ordered these," the girl confesses with her head down, ashamed. Only I catch that she's not ashamed for having those cuffs, but at not using them. That she knew it was the correct thing to do, and now that she didn't do it, she knows she did wrong.

This actually surprises me. This girl thought of cuffing herself? Of actually making herself helpless? That's interesting. Then again, if she has the key, she wouldn't really be all that helpless.

"See, you knew what you needed to do," I scold, wanting her to feel stupid. It has a clear effect as she lowers her head even more while her face flushes again. She even lowers the handcuffs as if her body is going submissive.

"For now, just remove the panties and sit back down. Only this time spread your legs as you sit, and put your hands behind her your head," I tell her, sounding upset, making her feel like she's wasting my time.

Whomever she is, nods as if to say she understands. She then puts the cuffs on whatever is holding the webcam. After, she faces the camera and grabs the waistband of her panties. Without any delay, she yanks them down. The moment she does, her shaved pussy becomes exposed.

If I could only whip my cock out to start stroking I would. The sight in front of me is beyond sexy as she struggles to step out of her panties, causing those fat titties to move all about. She looks so sweet and innocent as she nearly falls over that I can barely help myself. She's so nervous, especially as a stranger is seeing that sweet, innocent lil pussy.

Looking very much like she's being punished, the girl sits back in the chair now that she's completely naked. She only pauses for a moment before she spreads her legs to either side of the chair. After doing this, she seems to think about it, to which she spreads her legs even more, so they are nice and wide.

Right after, she sits up straight in the chair and looks at the camera. Then she puts both of her hands behind her head, where I can tell she interlocks her fingers. Now in position, she even lifts her head up some, as if proud that she's finally doing what she should have at the beginning.

Her putting her hands behind her head does exactly what I wanted it to do, which is make her arch her back. She doesn't arch it much, but it's enough. Now those huge tits of her stick out more, almost like she's presenting them to me to take.

Again, it takes all that I have not to whip my pants down and start going to town. I've never seen anyone look sweeter and more delicate than what she does now. I bet if I sold this image, I could sell it for a million dollars. Never before has anything like this happened, nor will it ever happen again. She's just so naïve, pathetic and wanting what is happening.

That's when I notice something that seems to change the dynamic. A part of me was feeling a tiny bit bad at how easy I was able to manipulate her. That I was taking advantage of some dumb, innocent girl. But now I see what I see on her, I don't feel bad at all.

The bitch is wet. Really wet. I can see how wet her pussy is now that she's removed her panties. She is clearly aroused, rather she wants to admit it or not. That means she is enjoying this. That she truly is getting off on the punishment and exposure.

Knowing she's enjoying this makes it even better, even if I need to keep pretending that she hates it. I know if I point out she likes it, she will probably disconnect because it would kill the fantasy. But she's about to find out that she connected with the wrong guy. If she really is local, which I know she has to be, then I'm going to find out where she lives. I won't end this night without putting my dick between those tits.

"Now the very first thing should have done, is to think up a name to call yourself during this punishment. But this name needs to relate to your crime. You need to pick, but it should be degrading and point out the obvious. So it should be something like...Ms. Tits. Or JugsMcBigTitties, or Senora Big Knockers," I explain, giving her examples of names she could use while trying to make her feel stupid that she didn't know to do this already.

The girl gulps after I tell her this. Before she took off her panties, I would have said she reacts like this because of the extreme humiliation, but no. That's not the case. She's liked what I said. She's dealing with a sudden wave of arousal. That much is clear. This girl is liking the thought of being called something crude and degrading.

"F-Fat Jugs. My name will be Fat Jugs. It's...it's what they call me at school," the girl reveals to which I nod my head. When she says this, she arches her back a bit more so her large breasts stick out further. I'm not even sure she knows she does this.

"Alright, Fat Jugs," I say, making her hear her new name. When I say this, I have to fight to keep my smile hidden as I need to play the stern father figure. But still, a part of me wants to laugh if they really do call her such a stupid name. People had more creativity back when I was in college.

"Let's get the obvious out of the way, Fat Jugs. What size are your jugs?" I ask. My goal now is now that she is prepared, I'll ask a bunch of questions to make her feel more vulnerable. The questions will get more and more personal. Once I think she's been broken down enough, I'll ask the real question, such as her address. But I have to break her down first, otherwise she'll know what I'm trying to do.

"GGG. I have a GGG cup," the girl reveals. It's here that I notice that she is embarrassed by how large her bust is, but another part of her is proud of it. She likes having such large breasts, if only for this to happen. It's a strange expression to see on someone's face.

"Now that I think about it Fat Jugs, if we are doing this correctly, whenever you talk, you really should make those monster jugs move," I tell her, just thinking this idea up.

It's the perfect way to help break her down, but is also something I think she would enjoy. Well, I really should say something we both would enjoy. It's focusing on her chest as well as feeling humiliating, which I'm sure is what she's after. I bet she jumps on doing it.

"I have a GGG cup, sir," Fat Jugs repeats, only this time she shakes her shoulders some, causing her large breasts to jiggle. They jiggle just a bit at first, but then move much harder as she does, damn near making me moan.

"Do you feel like a whore right now?" I ask, but only because I can't think of anything else to ask. Those tits in motion sure do hypnotize me. They make it so I can't think of anything but looking at them.

"Yes," Fat Jugs answers, shaking her breasts again. It would seem she really liked my suggestion of shaking her tits when she answers as it appears she's waiting excitedly for my next question. That she's happy she found herself an old man to fulfill this fantasy.

"You should. You certainly look like one," I tell her sternly, wanting her to feel a sting by my words. From the looks of it, she did. Her face twitches and then frowns for a moment once she hears it. Yet, I can tell she is getting more and more aroused. Even through it is via a webcam, I can tell her nipples are extremely hard.

"Go ahead and tell me what you are doing, and why," I say, starting to get worried as I'm running out of minor questions to ask. If I go too fast or want too much, she'll get scared and run off, I know it.

Fat Jugs takes a deep breath as if preparing herself to do such a horrible thing. This is almost comical as I watch her large chest heave upward and then down as she exhales. Then, she rolls her shoulders again, causing those huge milkers to start jiggling and bouncing all over. Only this time, she does it much harder as she is clearly getting into it.

"I...Fat Jugs, am sitting here naked, in front of you on webcam, my legs spread so you can see my womanhood, and shaking my boobs, because I am being punished. Punished for having such huge boobs which signals I'm a whore," she says while shaking her breasts hard the entire time.

If I was a good man, or even a descent one, I might be concerned what damage I might be doing to her. That I'm going to leave some mental or emotional damage inside of her. That forever she'll look at her tits and feel conflicted emotions. But I don't care. In fact, I'm going to do much worse and I really don't care. If she's so stupid to get caught up in this, it's her fault.

"Yes you are, Fat Jugs. And we both know how you deserve it too," I say in response, saying the last part to hit her hard. I need her to be slightly off guard because of what I'm about to ask next.

"Now tell me, where are you naked at? Is it a house with other people, such as your parents or siblings?" I ask, taking a chance to get some real information out of her. I notice that she doesn't stop shaking her breasts when I speak. She keeps on doing it, almost like she enjoys the feeling, or forgot about it.

"I, I mean, Fat Jugs, lives with my parents and my older sister. They are out of town tonight to go to a concert at my sister's college, so I'm home alone," Fat Jugs explains.

When she says this, I'm not sure if she's just being very honest because she feels she needs to be, or if it is an invitation. In the end, I guess it really doesn't matter. I'm still planning on finding wherever she is and taking what I want from her.

"Too bad. If anyone else was home, I may have suggested you go to them like this, so they can see the real you," I tell her, knowing I really wouldn't do anything of the sort. But it's just the sort of lie she would believe as it feels overly embarrassing.

The girl's face reddens again, showing how humiliating she finds doing that would be. Once again she looks down, overwhelmed by the embarrassing thought, no doubt from what her father might think of her. Yet, I know a part of her likes feeling the humiliation of it, for I swear there's a brief smile.

"Where does Fat Jugs live, in which part of our city?" I ask, trying to make it sound casual as I try to get more info. I probably fail at it, but the way I ask is so I can make fun of whatever part it is. Rather it be too poor, or high crime, or just a lot of whores in the area. It's also my way of trying to narrow down where she is.

"I...I mean Fat Jugs, lives in the Thunder Acres subdivision, on Rainy Day street. In the only yellow, two-story house on the entire street," Fat Jugs tells me, stunning me.

She didn't just drop clues but told me everything but the damn address. I'm so taken back by all this information I don't know what to say. So I just sort of look at her with a stern look as my mind starts to whirl with this new information.

"I see. I wonder if you are the biggest whore in that subdivision thanks to those tits," I reply, trying to play it cool now that I know where she lives.

And I do know where she lives. I know that subdivision. Oh goodness me, I know that subdivision and I'm pretty sure I know that street. It's the subdivision next to mine. Well, not right next to mine, but like two over. But I know exactly where it is, and how to get to that street!

Excitement floods over me, nearly making me break character. Instead of the stern and intense dom, I feel like a virgin about to start celebrating because I'm about to have sex for the first time. But I fight to regain my internal composure, as it'll make all that I worked for disappear. I'm sort of on the edge of a knife here, where it could go either way.

Trying to make my face appear stone-like, I can't help but think about if she could really live that close to me. Could this be real? Or is this some weird sort of trap? It doesn't feel like it, but it can't be real, right? She can't be real. No one that naïve, pathetic and with such huge tits could be real.

I thought she would live clear across town, to which I would only be able to dream about finding her. Or maybe make some vague threat about finding her one day. But this is real. Really real. I mean, I bet I could be at her house in like 5 to 7 minutes. It's that close.

The thought that she's loving all this comes back full force now. Maybe she just told me all that, not because she's stupid and caught up in the moment, but because she wants me to find her. She wants me to go over there and slap those titties about as well as show her pussy a real man's cock.

"Well Fat Jugs, you have taken up a lot of my time tonight, and I'm a busy man. So how about I prepare you for how you need to spend the rest of your night?" I pose to her, snapping out of my thoughts.

When I say this, her face drops. There is serious disappointment on her, like I just said her puppy had died. It's rather surprising and I almost laugh. It just confirms how much she is loving what I'm doing and saying.

"Y-Yes sir," she finally replies with a bit of sadness, shaking her breasts very briefly when she talks. Again I have to suppress my smile at this as she has no clue what I'm planning. That I may be grabbing those tits in my hands in just a few minutes.

"First, I've grown to despise that voice of yours. Pick up your panties and stuff them in your mouth, so no one has to hear you for the rest of the night," I order sternly. This time I sound very stern, making it seem like she will be in serious trouble if she doesn't do as she's told. I make it sound cold too, as if her voice is annoying instead of the feminine masterpiece it really sounds like.

Fat Jugs looks conflicted at this and stares at the screen as she ponders what to do. She then leans over and picks up her panties from off the floor. While holding, I can tell she's wondering what it's going to feel like, as I doubt she's ever put her panties in her mouth before. But the look see gives makes it seem like she may not do it.

"I'm waiting," I chime in, annoyed. Much like me earlier, this seems to snap her out of her thoughts. Holding my smile in, I watch as she balls up her panties while making a sour face. Once they are nice and balled up, she puts them against her mouth.

My cock throbs against my pants as she opens her mouth to slide her panties inside. Fat Jugs gags for a moment after doing this, clearly not used to them being in her mouth. She even has to put her hand up to her mouth to keep them in as she gags again. After a few moments, she seems to get the hang of having the fabric in her mouth because she puts her hands back behind her head again, while spreading her legs.

"Now, use those cuffs of yours to cuff your hands behind your back," I order next, wondering if she is really going to do it. Previously I was just playing about with having her get them out. But now there's a real chance that I can go to her, I want her helpless. I want her fucking arms neutralized so I can throw her about it I wanted to.

My guess is that yes, she will cuff herself, but you never can tell. Putting her own panties in her mouth may have made this all too real, to which she might end our night together. But her horniness might be strong enough to make her keep going. That she will do as I say in hopes of me staying here with her.

Fat Jugs has another sour looking expression as she leans over to grab the cuffs off the table or desk in front of her. Looking pathetic and in trouble, she keeps leaning forward as she puts both hands behind her back.

I can see her fooling with the cuffs as her dangling tits swing about, but she seems to be having trouble. My fears of this are eliminated as I hear the clicking sounds as both of the cuffs are snapped into place. She then moves her arms as if trying to bring them around, but can't.

To prove that I'm the one in control, she stands up and turns around, showing me her bare ass. But she then pulls her wrists in different directions, showing they are stuck as the cuffs are clearly on. She really did just cuff herself, with the key, I'm assuming, on the table in front of her.

"Good, Fat Jugs, good. Now, every five minutes, stand in front of an open window so the world can see your whore body. Stand there until you feel it's right to stop. Go. Now," I order her, knowing she can no longer speak, nor gesture with her hands. She can only look at the webcam with a rather helpless and pathetic look.

Fat Jugs looks at me in her computer screen, then looks around. She gives a look as if she's the one that can't believe this is happening. That she let things get this far.

Turning behind her, she sees the window that's in her room. It's a window with pretty white sheer curtains that hang all the way down, but are pulled to the sides. Better yet, it appears that the blinds are all the way up, making it easy to look into the room from the outside. She looks at the window and then back at me.

With her head lowered, she stands up and turns to face the window, exposing her backside to me. I then watch her walk towards that back window. And like the submissive idiot she is, she moves between the curtains and stands there, no doubt showing her naked front to whomever might be out. There's no effort to hide behind anything or to blue what they may see. No. She just shows her naked body off to the world.

"You best shake those tits while you stand there," I call out, wondering if she hears me from such a distance. I'm not sure if she really starts to do this, thanks to the curtain being behind her, but the curtains do start to rustle over and over as if she is.

With her attention diverted, I stand up and move to my living room. There I grab only my keys and not my wallet or my cell. This way if something bad goes down, I can't be tracked or leave anything behind. Such as if the cops trace the GPS on my cell, it shows I stayed home the entire night.

On purpose I leave my connection to her open and don't hit "EXIT". Nor do I tell her that I'm leaving. I'm going to leave her as she is, hoping that she stays in that window.

When she sees that I'm not there, I don't know what she's going to do. My hope is she'll think I went to get a drink or maybe to the bathroom. That I'll be back. I hope. I did tell her I was busy, but since I didn't log out, I hope she thinks I'll be coming back.

Once I am out of my house I get in my car fast. I then back up and drive down my street, going faster than what is legal, not that I care. Each second that passes, I worry that my chance with the big boobed brainless girl is over. So I drive as fast as I can without drawing too much attention to myself.

In only 4 minutes, I'm entering her neighborhood. I hadn't noticed how much time had passed since we got started, so it's pretty late now. That means no one is out on the road, which makes for no traffic. Which means I can get on the main drive of her subdivision insanely fasts.

With a smile that probably looks demented, I drive under the cover of night, hoping my car looks like any other you might see in this neighborhood. On purpose, I don't slow down as I look at the street signs because that'll make me stand out as it's clear I'm looking for somewhere instead of belonging here. That means I almost pass up her street.