Bill wanted to fuck my ass.

I wish there was more lead in, but it was Bill’s birthday, I asked him what he wanted, and he said he wanted to fuck my ass, so I said okay.

I’d never wanted to before. You see, Bill has a horse cock. It’s seriously fucking big. He’d expressed interest before, but I’d always shot him down. In fact, Bill had regularly lamented that he’d always wanted to try anal, but every woman he’d ever asked was too intimidated by his size. Still, it was his birthday, and I had promised him whatever he wanted. I’d hoped he’d want a PS5, maybe a nice dinner out, even a blowjob, but no. He wanted to fuck my ass.

That’s how I ended up on a Friday morning, as part of my morning routine, working a lubed up buttplug into my asshole before taking a shower. Not a small one, either. I was going to be ready, even if it meant spending my entire work day trying not to look too stiff, easier said than done with a big hunk of stainless steel inside me. If anyone noticed, they didn’t say anything. I certainly noticed, though. Every time I moved, I was aware that my ass was stretched about something that felt like it was filling it to capacity. I was also aware that Bill was bigger than he buttplug, and that he was not going to be so kind as to just sit inside motionless like the buttplug was.

Still, I couldn’t say that I wasn’t enjoying myself. Every move triggered something in me, that extremely primal pleasure, the kind that you can only understand if you’ve been fucked in the ass. Most men don’t realize just how different it is. Vaginal sex is incredible with no extras needed. It’s a flood of wonderful feelings that I can float away on. Anal, on the other hand, feels like it’s wrong, but in a good way. It’s as much psychological as it is physical. It’s like masturbating somewhere that you definitely shouldn’t be masturbating, it feels like something that really shouldn’t be happening, but it’s too much fun not to. It’s somewhere between being right in all the wrong ways and wrong in all the right ways.

I’d love to say that, by the time Bill showed up, I was used to the sensation. It’s not really a sensation you get used to, though. That’s part of the fun of it. As I got ready for Bill, changing from my work clothes to some slutty red lacy lingerie, red to contrast with my pale skin and compliment my auburn hair, I was still incredibly aware of what was inside me. When I got the text from Bill, saying he was only minutes away, I took it out and was overcome with an odd mixture of relief and disappointment. I was simultaneously glad to be done with it and sad to see it go. I grabbed my bottle of lube, then went and sat in the living room, dolled up and waiting for Bill.

He walked in right when he was supposed to, looking like a kid at Christmas. Honestly, in that moment, eyeing the bulge in his pants, I was beginning to have second thoughts. He was already hard, and I always forgot just how thick he was. Still he was at least enough of a gentleman to respect my wishes if I tapped out, so I opted to go through with it.

We didn’t make small talk. We didn’t talk at all. He eyed me up and down, closed the distance, placed a hand behind my head and kissed me deeply, grinding his khaki-clad cock against my bare stomach. I kissed him back, matching his ferocity. It was his birthday, after all, and I was ready to take things at whatever pace he wanted. I don’t often get nervous when it comes to sex. I love a challenge, and he was certainly going to be a challenge, but that didn’t mean that I wasn’t imagining how stretched that buttplug had made me feel, knowing that Bill was going to go deeper and harder than the plug had.

I pulled back from the kiss to catch my breath, and Bill quietly asked if I was ready. I nodded. He began to undo his pants and turned me around, forcing me to my knees, and then my elbows on the floor in my living room. I heard his pants hit the floor and get kicked to the side, then felt his hand on my asscheek, trembling as he slowly caressed it. I looked back to find him staring reverently at my body, my curves, like a virgin nervous about his first time. Softly, I wished him a happy birthday, then reached back and pulled my thong aside so he could see my waiting asshole. He took the bottle of lube and squirted some into his hand, working his shaft. I turned back around, waiting for the pressure.

It came, not as his massive cock pushing its way inside me, but his lube coated fingers preparing me, as he wasn’t aware of just how much prep work I’d already done. He pushed them in all the way until I could feel his knuckles pressing against me, wiggled the fingers around, then pulled them back out, rotated them 90 degrees, and pushed them back in, then repeated. As he did, I was reminded of why I love anal so much. Sure, it’s not something I want regularly, but the sensation of something thick working its way in and out of my asshole was lulling me into a dreamy state as he introduced a third finger, again and again and again.

Then again, it’s something different when a cock is introduced. Any woman, and certain men, will tell you that there’s a distinct difference between any number of fingers and a dick. It’s hard to describe, but it’s impossible to ignore. I don’t know how long I’d laid there, my cheek on the carpet, lazily accepting his fingers in my ass, but it was like a jolt of electricity to my system when he pressed the head of his cock against my hole. With that first push, that incredible feeling of pressure, my eyes shot open, and I let out a hard gasp. His fingers had prepped me, but nothing was like the feeling of that swollen head invading my ass. There was burning mingled with pleasure, there were alarm bells blaring in my brain as I was not only being stretched to my limits, but something was going in decidedly the wrong direction, tears seemed to instantly be pouring down my cheeks as I gritted my teeth and put the full force of my will toward making myself relax.

And then, with all that effort and patience, it was done. The head popped in. All of that for just the head.

I made a decidedly undignified sound as I felt it push in. Bill gasped, having been holding his breath in anticipation. I told him, maybe even begged him, to give me a moment to adjust. Both my body and my brain were processing a lot of sensations all at once. it was, and remains, the largest item that has ever been up my ass. I took several shuddering, calming breaths. I wiped my tears away, though every movement reminded me of the cock just waiting to push further inside me. He asked me if I was okay, and I assured him that the tears were from effort, not discomfort, and I gave him permission to slowly continue.

He hissed as he made progress. It’s bizarre, no matter how slow a man goes, a dick sliding into my pussy is just a wash of pleasure. In my ass, I was absolutely, acutely, intimately aware of every bump, every vein as it pushed its way inside me. He pushed in an inch, out half an inch, in another inch, out a half an inch, reaching the depth of my buttplug, then his fingers, then beyond. It felt like I’d taken feet upon feet of it when he finally couldn’t go any further. As patient as he was, Bill had gone as far as my body would let him, with inches to spare. I told him, my voice trembling far more than I’d intended, that I was sorry, but he shushed me.I propped myself up onto my elbows again, creating the odd sensation of moving with seven inches of thick, hard cock inside me. I winced and moaned. Bill offered to stop, but I shook my head. Trying to offer up a cocky smile that I’m sure was more weary than I wanted it to be, I asked him if he was going to fuck me or not.

Bill is a good man, compassionate, and sympathetic, but he knows how to take an invitation. He pulled back several inches, drawing an entirely undignified gasp from me as my body suddenly coped with an unbearable emptiness, then he slid back, not a brutal slam but a reasonably gentle push, not that my body got the memo. For the sound I made, somewhere between a scream and a squeak, you’d think he was brutally pounding me. He didn’t hesitate before pulling back again and pushing forward with similar force, then again, and again, getting bolder each time. A little further back, a little harder. I fell back off my elbows, my cheek rubbing against the carpet. I pushed back at him a bit, but my body seemed perfectly happy to be a receptacle for his actions. The best I could manage was to reach an arm between my legs, rubbing my clit to add to the pleasure, but even that was short lived before my arm fell limply to the floor. I felt useless and used.

Sometimes, it’s nice to feel useless and used.

My mind was in a daze, so I didn’t notice his breathing picking up, getting more labored, the subtle inconsistencies in his thrusting that all suggested that he was reaching his limit. I was, however, incredibly aware when he got there, pulling his entire cock out of me in one quick move, drawing a shriek from me loud enough that the neighbors probably heard, as I went from incredibly full to achingly empty in less than a second. Without his cock holding me up, I sank to the floor, gasping as I felt the hot impact of his jizz on my back again and again and again as he cried out. I tried to mutter out something sexy, but I quickly fell asleep.

I woke up several hours later, still on the floor, the feeling of dried cum on my back and sides. As I moved, my body told me to take it easy. I was sore, and I was empty, and I was spent. Bill was propped against a chair, still wearing his shirt and socks, his limp cock, still thoroughly impressive, hanging there. I tried to stand, but my legs were jelly, so I settled for moving into a sitting position against my couch, wincing slightly as I shifted weight onto my stretched ass, though it only hurt for a moment. That would last for the better part of a week, a quick shot of discomfort any time I adjusted. It was worth it, though. I watched Bill sleeping, a silly, stupid smile on his face. I was glad to give him what he wanted for his birthday.

Hopefully, though, he’ll be happy with a nice dinner. Maybe a blowjob.