Disclaimer: *The following story includes frequent use of humiliation/degradation, fat shaming, emotional sadism, etc. If you’re undaunted, proceed. Otherwise, maybe sit this one out.*

Author’s Note

I think it might be time to share this story. It’s about the first woman I ever truly degraded — or rather, the long week I spent breaking her in.

Consider this a journal entry of sorts. I’m going to fictionalize certain aspects, while telling other aspects exactly how they occurred; this is my prerogative and will ultimately make for a better story.

I’ve decided to write down these experiences because, lately, I’ve found myself revisiting these memories a little too often; and also, because I think some of you might enjoy reading this depraved story. And if there’s some lonely, old hag out there reading these words — a woman like the one I’m writing about tonight — maybe it’ll give you hope that something like this could still happen to you. (Feel free to DM me if you’re out there reading this, don’t be shy. I’m always looking for a new plaything to educate.)

Oh— and if you’re only here to read the lurid parts, I suggest skipping forward to Part 2.

Hope you enjoy.

Author’s Second Note

Since there was a good amount of interest in the first iteration of this story, I’ve decided to expand upon what I already wrote, and try to make a more complete story out of this account. If this is your second time reading about my Summer with Paige, then you should know that I’ve at least tripled the length of the original. Hopefully, this updated version of the story satisfies any desire there was to know more.

PART ONE: *Summer, 2012*

1. A Lifelong Desperation

Forgive me, I don’t know any other way to tell this story, except but to ramble endlessly, following each trail of memory as it appears. But, I’ll try my best to not jump around too much.

I’m in my early thirties now, but I was nineteen at the time. She was forty-eight. Let’s call her Paige. A divorcée, who hadn’t been with a man in eight very long years.

She had only ever slept with her ex-husband, who evidently hadn’t shown much interest in her after they’d turned thirty. More than half of her marriage was spent sexless, Paige had told me.

Her naivety and inexperience continually shocked me. Paige had given a total of two blowjobs in the course of her romantic life, one of them being on her honeymoon. Even the most vanilla concepts were foreign to her.

Needless to say, being sexually repressed well into her late 40’s had made Paige increasingly desperate to make up for lost time. When we met, that pressure had finally started to make her crack. I could tell, this woman had lost control of herself somewhere along the way, possessed by her need to finally be used. I was just lucky to be the first man who had the opportunity to take advantage of her.

2. A Mutual Education

I’d already experimented with the world of degradation and humiliation prior to meeting Paige, but none of those encounters were anything like my experiences with her. They were superficial and performative in comparison. With Paige though, it didn’t feel like a mere “kink”; instead, it felt like an honest reflection of our true natures; something real, tangible.

At nineteen, it felt extremely liberating to be so blunt and callous toward an older woman, and equally intoxicating to see her submit so willingly to my cruelty. There was also the fact that Paige was nearly 30 years my senior. That age gap somehow made it easier to indulge in my worst instincts. I mean, it’s not like we had anything in common to make small talk about. This prevented any kind of niceties from developing between us. She was there for one purpose, and neither of us ever forgot that.

I spent the Summer after I graduated high-school using and abusing Paige every night, or every other night. If I didn’t have somewhere else to be, I was at my place, chain-smoking joints and using Paige as my living stress-reliever. (Sometimes simultaneously, which lead to me using her cunt as an ashtray on two separate occasions. I’ll never forget seeing the ash land on her labia, before immediately being dissolved by her wetness.)

I often told Paige that I was providing her with a type of “education”, teaching her how to make her neglected fuck holes serve a purpose for the first time in her life; but in reality, I was also receiving a kind of education that Summer. Before, my own dominance had felt like an abstract, faraway concept to me. At best, it was a character I could adopt. After Paige, I rarely flinched away from my dominating instincts, and instead embraced them without compromise. Suddenly, I could tell a woman to knell before me and she’d know that I meant it. My voice no longer betrayed that I was performing a role; now, I could simply embody it. Breaking in Paige had ultimately transformed myself as much as it did her, making me into the fairly seasoned Dom I am today.

3. A Four-Minute Walk of Shame

We met on FetLife. I had posted an ad seeking a sub with a taste for humiliation, then we quickly realized how close we lived from one another. Her apartment was just a little down the block from the house I was living in at the time, no more than maybe a four minute walk.

This enabled us to meet frequently, and usually with little to no notice. By the time the Summer was over and the leaves were starting to crinkle and change colour, Paige’s fuck holes looked noticeably different. Her asshole was visibly stretched. Her cunt no longer felt as tight as it once had. I’d throughly squeezed every last drop of sexual value out of her, I’m convinced of that.

Like I said, I was nineteen, which meant my sex drive was nearly bottomless. Some days, I would have fucked Paige five or six times. I don’t think I even masturbated that Summer. She was my human cum rag. And she was always there whenever I needed her — just four minutes away.

PART TWO: *The First Week*

4. Please Try Again

By the time that we’d decided to meet IRL, our conversation had already gone from being fairly vanilla humiliation/degradation fodder, to being something more twisted and perverse. It didn’t take long for us to realize the other was uniquely equipped to deal with the depths of our worst desires.

The first week, while I was still breaking Paige in, I decided to take my time with her. Although she had been willing to fuck on sight (literally the second she saw me), I thought it would be more interesting to make her earn the right to kneel between my feet. I could see how much she wanted me. How giddy and butterfly-drunk it made her just being alone in a room with a handsome nineteen year old. I wanted to draw out that anticipation for as long as I could.

I invited Paige over every single night that first week. She’d stay for around an hour, sometimes a little longer. Until the seventh day, I didn’t even fuck her. Her desperation was too addictive, I couldn’t ruin that. I couldn’t give her what she needed so easily and spoil that pathetic, needy glint in her eye. So, every night ended with rejection, and then, an invitation to Please Try Again the following night.

I didn’t even let her taste my cock between her lips for the first couple nights. Instead, I spent the hour or so that we shared each night bullying and degrading Paige, humiliating her in new, sadistic ways. That week was like one long job interview to become my fuck pig, where the only requirement was being desperate enough to keep coming back for more.

After I was done testing her limits for the night, I’d send her home, where she edged herself at my command. She had the strictest instructions not to orgasm until she saw me again. Not that I let her orgasm in my prescience either, but that was the carrot that I dangled in front of her all week.

During the day, she’d text me endlessly about how her worthless cunt was aching or whatever, and I’d reliably ignore her, until I got bored in the afternoon and eventually would tell Paige to walk over. Five, ten minutes later, there she’d be, standing in my doorway, looking like some lost child. Standing outside my door, her cunt already wet enough to smell the moment she stepped inside my house.

How does a man not take advantage of a woman so eager kind to be used and abused?

5. A Thorough Inspection

The first night she came over, I didn’t waste any time with small talk. I told Paige there was no point proceeding if her body wasn’t enough to even make me hard. People were more shy about sharing nudes back then, so I didn’t really have a good idea of what I was working with yet. I knew she was nervous that I wouldn’t find her attractive because she was pushing 50 and frankly, so was I.

I sat in the sofa chair, with a whiskey and coke on the table beside me, and a joint smouldering in the ashtray. I told her to stand between me and the large mirror on the other side of the living room, giving me a convenient 360 degree view.

I remember her asking me right then if I was “happy with what I saw”. Cat-fishing was still a fairly new term and Paige said she hoped I didn’t feel like she’d done that to me. She wasn’t what I expected from the limited pictures I’d seen (even with her clothes still on), but I wasn’t disappointed about that. I knew the middle-aged, divorced hag I’d invited over wasn’t going to be a bombshell, and I told her as much. I think that was the first time I said something truly cruel to her face. I remember thinking she might storm out, but she only nodded and whispered agreement. I even recall repeating that phrase — ”divorced hag” — and being surprised and a little delighted by her compliance. I think that’s the moment I knew I could do anything I wanted to her.

Next, I told Paige to undress for me. Slowly, so I could study her body inch by inch, deciding if I’d let her serve me. She was literally shaking from nerves. That was my favourite part. It had been a long time since anyone had seen her naked and she’d aged considerably since then. Not to mention, it was a nineteen year old watching her undress. Her nervousness was palpable. Something about it was intoxicating.

Once she’s taken off her bra, I asked Paige to lean forward for me, letting her tits hang freely, so I could see “how saggy they were”. I remember registering another look of hurt indignation on her face for a fleeting moment, but she didn’t hesitate to follow my command.

After, I instructed her to do jumping jacks for me. I remember that being the moment I started to get hard enough that she could have spotted the bulge in my jeans. Something about the pathetic way her deflated tits slapped against her chest each time she jumped… The way her fat ass quaked in the mirror behind her… The way her expression looked: embarrassed and ashamed, but unable to stop herself…

I was drunk before she’d even showed up (I drank a lot that Summer, like most nineteen year old’s do). Which I bring up only to explain, I didn’t intend to be as cruel to Paige as I had been that night. I never imagined myself mocking her tits for being old and wrinkly and past their expiration date. But seeing her accept the cruel remarks I’d made about her body, it made me only want to insult her more. It was like some drug I’d just discovered. There was something so satisfying about talking shit about her breasts, then watching her still shake them back and forth for me, so desperate for my approval.

I didn’t rush through this. I simply sat there, drinking and smoking, while I measured her potential as a plaything. I don’t remember seeing a single moment of hesitation on her face, despite looking throughly humiliated. She was still beyond nervous, but she never hesitated to follow a command.

At one point, I remember asking her to slap her tits around for me. They may have been saggy and deflated, but they were still pretty hefty. The enthusiasm and force Paige slapped her own tits with surprised and excited me. I could tell in that moment how fun she’d be to abuse. If she would do that to herself, imagine what she’d let me do to her.

When she was done, I made her bend over for me, so I could sample the tightness of her holes with my finger-tips. I remember thinking her cunt felt surprisingly tight, like a girl’s my age would. That’s when she told me about her divorce and about how limited her sex life had been. I asked her what it felt like, to be the age she was, bending over in a stranger’s house, letting a drunk teenager finger her worthless holes, all while she explained what a failure of a love life she’d had.

It was so deliriously pathetic, all of it. Pointing this out to Paige made her cunt throb around my finger. I didn’t know a “shamegasm” was a real thing yet, although I learnt otherwise later that Summer. If I’d have known better at the time, I would have identified exactly what I saw. The overwhelming shame of my words had triggered something, I think, resulting in Paige’s legs quivering visibly for a moment. Maybe what I’d said cut through the adrenaline and the surrealism of the moment, and reminded Paige that this was real, she was really doing this right now.

That night, I ended up stroking my cock while Paige knelt beneath me, her knees on the hardwood floor, until I came. Pretty sure I spat on her face shortly after I emptied my balls, while she was still recovering from the shock of receiving her first facial.

I didn’t let her touch my cock that night; she could look, but she couldn’t touch. We agreed, a woman like her had no business even being naked in the same room as me. If I was going to let her serve me, she had to prove she understood her place first.

After I came on her face, I told Paige to “stand up, get dressed, then go the fuck home and wipe my cum from your face. In that exact order.” One second, she was greedily licking my cum from around her mouth, wiping her cheeks with her fingers, savouring every drop. And the next, she was looking up at me, hurt, eyes round like saucers. But she stood up.

Before she left, I told her I’d let her come back tomorrow and prove herself to me. But in the meantime, she wasn’t allowed to orgasm without my permission.

6. My Summer Project

Paige knew I was seeing other women. Younger, far more attractive women. And she probably understood that this made it easier for me to deny her. I was never going to have blue balls. I think this turned her on. But honestly, once I’d broken Paige in and made her mine, I lost almost all interest in other women. Making her my ideal fuck pig become my Summer project. I didn’t have time or energy for much else.

7. Wet Eyes

This pattern of denial and rejection continued every night that week. The following encounter, I bent Paige over my knee and spanked her old, shapeless ass raw. That was the night I had laid out for her what our “ground rules” would be, in between rounds of spanking — and then when my right hand had started to sting, rounds of paddling.

After, I came on her face again, just like the previous night, then I told her to fuck off, just like the previous night. That had become our routine. Me standing there, stroking my cock, and her knelt beneath me, grovelling. Staring directly into Paige’s wet eyes while I verbally degraded her always made my cock harder. My words often visibly hurt her, but seeing my cock rock hard only made her more desperate to take the abuse.

Each time I did this, I remember the need and desperation in Paige’s eyes intensifying a little more than the night previous. I’ve never seen desire rendered so palpable. You’d think I was taunting someone dying of thirst with a glass of water.

8. An Exponential Cruelty

Even though I deliberately ignored her texts during the day — it was an endless barrage of increasingly desperate nudes — I couldn’t stop thinking about Paige between each encounter that week. I had twenty-four hours to imagine yet another novel way of inflicting my cruelty upon Paige. The mental game of always needing to conjure up a new means of degrading her became a part of the appeal. Having to constantly top myself.

Imagining these new scenarios always made my balls swollen and sore by the time we did meet. My loads were thick, ropy and always left me feeling utterly drained. After I came on her face (often in her eyes, too lol) and told Paige to walk home, I’d smoke a joint and immediately pass out cold. And I would have the best sleep. When I’d wake up, there’d always be a bunch of texts from Paige the night before, begging me to finally make her worthless fuck holes good for something.

As crazy as it might sound, although those nights of taunting and degrading Paige couldn’t even be called real sex, and definitely not good sex, it was still the most satisfying sex I’d ever had.

9. Trial by Tribulation

The third and fourth nights, I couldn’t tell you what order these took place in, but one of them consisted of me watching Paige fuck a suction-dildo stuck to my fridge, then scribbling on her body with a Sharpie; and the other consisted of me pissing on her in the shower, after making her give me a forty-minute massage (during which her bare tits made about as much contact with my back as her hands did).

The massage felt good. The idea had simply occurred to me as a generic form of servitude, but in practice, it turned out I liked massages, more than I’d expected to. I found myself drifting off for fleeting moments, before being brought back by the sensation of Paige’s nipples grazing my back.

The fifth night, we took it out of the house and went for a walk. Y’know those remote control anal plugs? I’m pretty sure this was when they first hit the market. I’m not positive, but they seemed like more of a novelty product back then. And for good reason, because it barely worked.

After making Paige stuff the little vibrating plug up her ass, the remote quickly stopped functioning. I remember being hidden behind some trees on a hiking trail people rarely used, with Paige’s pants and panties pulled down over her fat ass, and he desperately pulling the plug out, shoving it back in, trying to get it to work. In the end, I made the plug vibrate after all, but simply grabbing the end of it and doing it myself. I scolded Paige the whole time, blaming her fat ass for blocking the signal. By the time I was done, her cunt had started leaking all the way down her legs.

Before pulling her pants back up (I left her panties a wet, uncomfortable and tangled mess), I told Paige that one day, I was going to take her anal virginity. And it would probably hurt. A lot. I told her she probably wouldn’t know when to expect it, but she had to always be ready for it. I recall telling her that I’d fuck her virgin ass ”like someone practicing rape on a Fleshlight”.

10. Delayed Gratification

The seventh and final day of withholding my cock from Paige was the most rewarding. To this day, I don’t think I’ve had another sub satisfy me as deeply. It was the weekend and I was day drunk. I texted Paige sometime after having lunch with my friends and told her to meet at my place.

I was sat in that same sofa chair again. Paige was knelt on the carpet in front of me, naked and eager to be used again. I told her that today she could give me a tit job. I told her just because her tits weren’t much to look at, doesn’t mean they didn’t still have a decent purpose left. Sure, they weren’t firm anymore, men rarely ogled then, but their shapelessness was good for something. I told her it could make her massaging my cock between them feel better. Pretty sure I used the phrase “Playdoh tits”, and while I still don’t know what that means, I stand by it. MILFs tits just wrap around a cock better, they mould themselves around your shaft.

All the begging Paige did over text had started to bleed into our encounters. While she stroked my cock between her tits, she begged me to finally make up my mind. She told me she’d do anything if it meant she could walk home with my cum dripping down her legs instead of her face. She told me she would be moving in the fall, and that while she was still here, she wanted to be my dedicated slave. 24/7, whenever I wanted to use her worthless fuck holes. We’d talked about this concept when we first started texting, but now it seemed like a real prospect. My slave, on call 24/7. There was a raw passion and conviction to how she spoke that made me rock hard, and Paige noticed. I told her I was still deciding if I thought she was capable of satisfying me, but I’ve never been more sure of something in my life.

While giving me a titjob (I’d thought to buy baby oil at the 7-11 earlier that day), Paige asked me if she could lick the bead of precum from the tip of my cock. I said no. The pain on her face was exquisite. She just watched the bead of cum slowly spread across on her tits, as she continued to bounce her fat udders on my cock.

Next, she asked if she could gargle my balls. I said sure, why not. It didn’t take long before the precum was leaking down my shaft, all the way to my balls. I could feel her tongue chasing the stream of cum, licking it up from my balls as it collected at the base.

Then, as the stream of spit and precum started flowing past my balls, I felt her tongue begin to graze my asshole. This surprised me for two reasons. First, because I’d never been given a rimjob before and I’d never even thought to ask for one. And second, Paige told me that she hadn’t given more than two blowjobs in her whole life. Which is why I took so much perverse glee from denying her the chance to choke herself with my cock in the first place. I knew she felt like she had to make up for lost time. I was shocked that giving a rimjob was even something in her sexual vocabulary, let alone something she was willing to do unprompted.

I couldn’t tell you how long I sat there and just let her rub my balls on her face and lick my asshole. Felt like an eternity. This was the first time she’d smoked pot with me before her daily humiliation ritual and it really showed. There was an extra degree of shameless that I hadn’t seen from her before. The way she smothered her face with my balls, like she’d forgotten oxygen was a thing.

The moment I leaned back into the sofa chair, I heard Paige begin to beg me for the last time. I’d feel her tongue flicker against my asshole for a moment, then she’d stop for a second to whisper up to me, her lips brushing against my skin as she did, before I’d suddenly feel her tongue begin lapping away again. The pathetic quality of her grovelling increased the longer I simply leaned back and closed my eyes, silently enjoying the unfamiliar sensation.

Paige confessed that she knew, deep down, that she couldn’t satisfy me. That she was old, decades out of my league (if she was ever in it). She told me because of her lack of experience, she probably wasn’t going to be a very good fuck either. She said she was humiliated that she wasn’t the one in the position to be teaching me. That she was nearly 50 years old and begging a 19 year old to teach her about her own fantasies. All the while, in between each burst of brutal honesty and desperate self-depredation, Paige continued to service me.

Like I said, I can’t tell you how long all of this lasted for, but long enough that I had to fill my drink before it was over. Paige fetched the bottle for me. I made her crawl to the kitchen to get it. Watching her fat ass clap each time her knees hit the ground made my cock painfully hard.

She told me that if I was willing to still fuck her, I could do anything I needed to make it enjoyable for myself. She would be grateful, no matter what. After hesitating for the first time since we met, Paige told me that she hated the idea of anal, and that the plug I’d shoved into her ass that day on the hiking trail had made her feel tremendously uncomfortable, but… If I needed to, she’d want me to fuck her ass as hard as I had to. If it took that to make her worth fucking, then she understood. And she’d be grateful. “It would still feel like charity.”

If I hadn’t stopped her, I would have cum just from her tongue and hearing her pitiable ramblings about how worthless she was.

11. With Flying Colours

I didn’t last very long. I forced my cock in Paige’s ass hard enough to make her squeal and bite down into the couch, fucked her as hard as I could for about a minute, then shot my load while i was still deep inside her. I think she hated every single second of it. Actually, I know she did, that much was obvious from the tears, the screams, the way she kicked her legs involuntarily. But afterward, she still seemed to somehow have an afterglow. I guess she knew she’d passed all my tests.

12. A Domestic Need

I expected that to be all for the night, but when I came back from having to take a quick phone call in the bathroom, I saw Paige standing in front of my kitchen sink, idly washing a plate. Seeing her there, naked, cum still dribbling off her chin, washing my dishes, that unlocked something in me: a domestic need that I didn’t know I needed — and I desperately needed it.

That Summer, I was living alone. My parents were overseas. And seeing as I was nineteen, I didn’t clean up after myself very well — or at all, really. Looking back, Paige did enough cleaning around the house to have earned a real wage as my maid. She even cooked for me a couple times, always while wearing only her panties, with those fat udders hanging exposed.

If you’ve ever seen the television show It’s Always Sunny in Philadelphia, and you remember the episode about Frank’s bang maids, well, that’s unironically essentially what Paige made herself in that moment. Ever fuck a woman’s ass, tell her to cook you a steak, then eat it while she kneels under the table, worshipping your cock?

Afterword

That’s going to be all — for now, anyway. Who knows, maybe I’ll elaborate more on my experiences down the road, if there’s any interest. Likely, that would take the form of me updating this story again with additional chapters included, much like I did this time.

If you’ve read this far, drop a comment below and let me know which part of this story stuck with you the most. I’m always curious about that, which part of my stories resonate with people after they’ve read them. That detail or scenario that gets lodged in your head, remembered long after you forget where you encountered it.

And, as I said at the start, my DM’s are always open. Don’t be shy. The last time I posted this story, I received a couple interesting DM’s. One in particular had proved to be fruitful. I enjoy educating beta women and teaching them about their place. If I have any time to spare, I’ll happily make you my next project.

Take care for now.