I think it’s time to share this story. It’s about the first woman I ever truly degraded — or rather, the week I spent breaking her in. Consider it a journal entry of sorts.

I’m in my early 30’s now, but I was 19 at the time. She was 48. Let’s call her Paige. A divorcée, who hadn’t been with a man in eight very long years. And even when she had been “sexually active”, she wasn’t really. She’d only ever slept with her ex-husband, who evidently didn’t have much interest in her after they’d turned 30. More than half of her marriage was spent sexless, she told me. Paige hadn’t even sucked off another man before. Needless to say, being sexually repressed well into her late 40’s had made her increasingly desperate over the years. When we met, that pressure had finally started to make her crack.

I’m deciding to write my experiences down because lately, I’ve found myself revisiting these memories often, and also, because I think some of you might enjoy reading about my summer with Paige. And if there’s some lonely, old hag out there reading these words — a woman like the one I’m writing about — maybe it’ll give you hope that something like this could still happen to you.

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 her though, it didn’t feel like a “kink”, it instead felt like an honest reflection of our true natures.

At 19, it felt extremely liberating to be so blunt and callous toward an older woman, and intoxicating to see her submit so willingly to my cruelty. There was also the fact that she was nearly 30 years older than I was. The age gap somehow made it easier to indulge my worst instincts. It’s not like we had anything in common to make small talk about. This prevented any kind of niceties. She was there for one purpose, and I never forgot that. Neither did she.

I spent the summer after I graduated highschool using and abusing her every other night. If I didn’t have somewhere to be, I was at my place, chain-smoking joints and using Paige as my living stress-reliever. By the time the summer was over and the leaves were starting to change colour, her holes looked noticeably different. Her asshole was visibly stretched. Her cunt no longer felt as tight as it had. I’d throughly squeezed every last drop of sexual value out of her.

Like I said, I was 19, which means my sex drive was nearly endless. 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 when I needed her.

We met on FetLife after I 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 a couple minute walk. This ended up being a blessing.

By the time we’d decided to meet, 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 breaking Paige in, I decided to take my time with her. Although she had been willing to fuck on sight, 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 drunk it made her just being alone with a handsome 19 year old. I wanted to draw that out as long as I could.

I invited her over every night that first week. She’d stay for around an hour, maybe longer. Until the seventh day, I didn’t fuck her. I didn’t even let her taste my cock between her lips. Instead, I spent the hour we shared each night bullying and degrading Paige, humiliating her in some new, sadistic way. Like one long job interview to be my fuck pig, where the only requirement was being desperate enough to keep coming back.

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. Not that I let her orgasm in my prescience either, but that was the carrot I dangled in front of her for that week. All day, she’d text me about how her needy cunt was aching and I’d ignore her, until I got bored in the afternoon and told her to come over.

The first night she came over, I didn’t waste any time with small talk. I told her there was no point proceeding if her body wasn’t enough to even make me hard. 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.

Then I told her 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 since then. Not to mention, it was a 19 year old watching her. Her nervousness was palpable. Something about it was addicting.

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

She did jumping jacks for me afterward. 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 up. The way her fat ass quaked in the mirror.

I was drunk before she’d even showed up, so I didn’t intend to be as cruel as I had been initially. I don’t think I imagined myself mocking her tits for being old and wrinkly and past their prime. But seeing her accept the cruel remarks I made about her body, it made me only want to insult her more. It was like some drug I’d never tried before. 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 my slave. I don’t remember seeing a single moment of hesitation on her face. She was very 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 she slapped her own tits with surprised and excited me. I could tell in that moment that she’d be fun to abuse.

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 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. Pointing this out to her made her cunt throb around my finger.

That night, I ended up stroking my cock while Paige knelt beneath me, until I came on her face. I didn’t let her touch my cock. 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.

Paige knew I was seeing other women. Younger, far more attractive women. And she probably understood 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 interest in other women. Making her my ideal fuck pig become my Summer project. I didn’t have time for much else.

After I emptied my balls on her face, I told her to “stand up, get dressed, 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 herself without my permission.

And this pattern continued every night that week. The following encounter, I bent her over my knee and spanked her old, shapeless ass raw. That was the night I explained to her what our “ground rules” would be.

I expected that to be all I’d do to her that night, but when I came back from having to take a quick phone call in the bathroom, I saw Paige washing a plate in my kitchen sink. Seeing her standing there, naked, cum still dribbling off her chin, washing my dishes, that unlocked something in me.

That summer, I was living alone. My parents were overseas. And seeing as I was 19, 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.

The second night ended the same as the first had. I made her watch me jack off onto her face before kicking her out the door. 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.

Even though I deliberately ignored her texts during the day — it was an endless barrage of desperate nudes — I couldn’t stop thinking about meeting Paige again after each encounter. This always made my balls swollen and sore by the time we did meet. My loads were thick, ropy and always left me feeling drained. After I came on her face (and often in her eyes lol) and told Paige to walk home, I’d smoke a joint and immediately pass out. 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.

The last 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 had her meet me 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 over text that she hadn’t given many blowjobs before in her life. She said she could count the times “on both hands”. Which is why I took so much perverse glee from denying her the chance to choke herself with my cock. 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.

She told me she knew 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, 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 me want to

She told me 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, she told me she hated the idea of anal, and that the plug she wore home had made her feel tremendously uncomfortable, but… If I needed to, she’d let me fuck her virgin ass as hard as I had to. If it took that to make her worth fucking, she understood. And she’d be grateful.

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That’s all I’ll share for now. I hope you enjoyed. And I hope you can excuse any spelling or grammar mistakes above. If there’s any demand, I’ll post more soon.