Painal: My First Experience

I'm a little tipsy and sleepy right now, but I'm feeling nostalgic, so I'll tell y'all about my first anal experience. I'll save the worst for another day.

I had already been watching humiliating and rough porn and fucking my pussy and ass with household objects for ages.

I'd discovered it pretty early on in my sexual awakening, but lived in a pretty religious and repressed household. So by the time I was taking college classes, I was obsessed with using my freedom and living out as many of my fantasies as possible. Particularly consensual non-con anal scenes. Especially humiliating and painful ones. So don't read through this if those themes make you uncomfortable.

I'm actually surprised I had the gall when I hadn't ever managed more than a couple fingers or a thick marker in either hole. At least, that was the case before I lost my vaginal virginity about five or six months before this in a one night stand.

However, that's another story. This is when I lost my anal virginity.

------

I had recently become brave enough to find a regular fuck buddy. It was a pretty new dynamic. A few months in, but we were meeting up to go at it daily or multiple times a day. Spending every spare moment naked. Our sexual compatibility got off to some awkward starts, but we soon got the hang of it. It got to the point we could read each other's silent signals very well.

A lucky accident. I picked him because he was funny, zero commitment, and I had felt how huge his cock was when he took me out. 

I found myself having fantasies about how much taking his cock would hurt, but it was an intimidating cock. Eight inches is a cliche claim, but he genuinely had an eight inch cock. It's why I picked him. I only measured it later, of course, but I had been drooling over it ever since I first saw his bulge and felt him through his jeans while making out.

When we finally fucked and I realized how hard I came when it felt like he was pummeling my cervix, I knew he had to be the one to take my anal virginity.

I went into it with the goal of making my first anal experience rough.

I knew it was dumb, but the fantasy was too big in my head to resist by then.

I was only going to have a first anal experience once, so I was going to go hard.

I was at least smart enough to fuck him in more vanilla dynamics until I was pretty sure he wouldn't murder me.

So we'd been fucking like rabbits for a while and had been playing rougher the last few weeks. It was long enough that I had learned it could take him an hour or more to cum sometimes.

Which both terrified and thrilled me. I knew his death grip meant I'd be a mess by the end of it.

I should mention that I also had a roommate. I'd asked her to move in because he last situation wasn't great... but mainly because we were all young and had been drunk enough times together to know we all had some similar kinks. So we'd all be chill walking in on each other screwing in the living room. It wasn't unusual for her to watch us, and occasionally get a little handsy with one or both of us. She was also sometimes into giving and receiving nipple play.

That was her line though.

She just liked to use us to warm herself up for her other partners and we used her to warm up each other. Which was a little disappointing at first, but soon became a comfortable and fun dynamic.

------



Anyway, my roommate was cleaning and moving about the place a lot that day. I was in my room with the guy I was fucking, and he was having trouble finishing. It was summer (with no air conditioning) and we'd been at it for an hour already.

We were sweaty and sticky and both having trouble cumming, but I was so worked up that I didn't want to stop.


He had been fucking me doggy style, so when he pulled out and said "Not happening. It's too fucking hot!"

I made a split second decision and decided to go for it. I didn't want to give myself time to think and chicken out.

I arched my back to give him a good view. I tried to be mischievous when I looked back over my shoulder at him and said "You know, we do have another option that might work better."

My heart was pounding, pretty sure I couldn't pull it off. I was always a nerdy tomboy. The rule follower. I wondered if he could see how much I was trying not to shake at the rush of adrenaline. Wondered if he would laugh at my attempt to be sexy. 

He froze so suddenly it was like he had just noticed a deer he was trying not to scare off.

He couldn't quite process what I was offering him, even though I was putting on a show rocking my hips and spreading wide, giving him a good view of the hole in question. 

When he finally processed what I'd said, his look changed. He didn't seem sure he could trust the offer was real, but he couldn't help smirking at the possibility. I saw a gleam in his eye that I had seen a few times before. Predatory alertness. Calculation. Mischief. The little experience I had with it that look always made me feel weak and excited.

"Oh, do we now?" he said, starting to knead my ass and rock me back and forth a little.

He'd been getting soft before he pulled out, but now his cock was recovering in record speed. It was only moments before he pressed it between my cheeks so I could feel how hard his shaft was. He kept me like that a little longer, slapping my ass on occasion. Rocking my ass cheeks around his cock and teasing me.

He then surprised me by trying to shove it in dry, rocking and putting so much pressure on my ring that I could feel how bad it was gonna be when he managed to get in. We were both too hot and sticky for it to work though. I was disappointed and relieved simultaneously.

But since it was so hot we'd long ago used up most of our extra moisture. A blowjob wasn't working. My once wet pussy was also sticky from heat and friction.


I had a moment of pure frustration as he struggled to get his cock in my ass, worried he'd give up in the heat. My heart just sank. I had so much riding on this experience. This was not the fantasy I wanted. I thought I might cry if I had worked myself up to this moment and didn't get to do it.

He wasn't giving up though. He heard my roommate in the hallway and changed his strategy.

He shoved my face hard into the bed with my ass up. 

He called her name and then asked "Do you have any lube? She is begging to get ass fucked and she wasn't prepared. Like she should have been." He said this last with a hard slap on my ass and such a condescending emphasis. 

I couldn't see her, but I heard it when my roommate laughed and said she had some.

My cunt certainly found some extra fucking moisture at that. His tone and the humiliation had me melting.

He noticed and finger fucked me so he could show her how wet I suddenly was. When she came back with the lube, they discussed it for a couple minutes like I wasn't even in the room.

He drew out their conversation while he finger fucked my pussy and I got increasingly frustrated. Finally my roommate slapped my ass, and said she had things she needed to do and to have fun.

She had given him a sample packet she had on hand and she left the room, but I noticed left my door wide open when she did. I know she kept peeking in on us between chores, she suddenly had a lot of reasons to walk up and down that hallway.

It wasn't much lube for a first time. He put some of it on the head of his penis and shoved one finger up my asshole with barely a pea sized amount on it. 

He wiggled his finger around to watch me writhe a bit. Testing if I would really let him stick something in there. I think he only used half the tiny packet.

It hurt so much and filled me with so much dread, but he didn't know how inexperienced I was. I was determined to keep it that way. 

Suddenly he pulled me up from behind, cupping my breasts for his leverage. He pulled me up straight until I was fully upright on my knees. Still behind me, he ordered me to scoot forward, put my tits against the headboard and hang on.

I didn't realize until he shoved his cock against my asshole in that position, that it would use my body weight against me if I tried to struggle.

He wanted to fuck upwards into my ass so that I would practically be impaled on him. If I struggled, I'd just have a few inches of wiggle room pressed up against the headboard and he could just grab my hips and slam me back down. Which did come in handy for him when I couldn't take the intensity.

He started so slow, it was torture all on its own. Giving me plenty of time to feel how thick he was, and just how impossible it felt to take. Only halfway in and I was suddenly very sure and very afraid of how much it would hurt.

The worst part of it was that I knew I could physically take it, even as my brain screamed at me that I couldn't.

I'd watched enough porn to know he was going to be able to getevery inch in and I was about to get exactly what I had dreamed about. The fear made my nipples so hard it hurt to press them against the cool wood.


He eased me down on his cock, slow and steady. Enjoying how I was going through spasms and how my gasp had turned into a strangled moan of pain. He didn't stop pushing until he was halfway in.

"You good?" He asked and I barely mumbled out a "yes", trying to breathe and not panic as I clenched hard around him. Just a few inches and I could barely focus on anything but the pain.

I chickened out.

I didn't ask him to go hard.

I was so ashamed of myself... but I couldn't quite given in either.

I didn't ask him to stop.

I didn't ask him to go slow.

I surrendered control and hoped I wouldn't regret it. Which is how I got the fuck I was looking for.

He barely let me get out the word "yes" before he slammed upward and pulled my hips down so hard that only hanging onto the headboard kept me from flopping in half at the hips like a doll and slamming my head against the wall.

The rest of his eight inches were ripping into me. So distinct a feeling. So intense I felt like I could feel every point of contact.

In an instant it went from a slow torture that made me want to cry quietly, to something that made me scream. The burning and ripping feeling in my defiled ass stretching to accommodate a hard upward fuck that seemed designed to drag my guts out of me when he pulled back.

Despite the heat and our long session, he fucked me hard like that for a good 10 minutes. It's a blur lost to total sensation. I was too overwhelmed to cum, but riding on the edge as he brutalized me.

I discovered his sadistic side was a much deeper well than he had shown me before.

Sometimes he would pull almost all the way out, and fuck my sore little ring a bit, never quite pulling back enough to give me room to squirm off his cock. He made it hurt so much I wanted to beg him to just slam it back in. Instead just whimpered and whined pitifully, which only encouraged him.

When I would convulse or seem to try and struggle, he'd grab me with one arm across my shoulders or grab my neck and hips and make me arch back against him. He'd pull my my neck and head back until it would be cradled almost lovingly against his shoulder and I was looking up at him.

He'd look into my eyes and start making hard deep thrusts or shorter but more brutally angled thrusts that felt like they'd raise me off of my knees a little, if he wasn't holding me down. Only letting me press back against the headboard when he felt me go limp.

The pleasure when he looked into my eyes and he let me see how much he enjoyed hurting me is when I realized this was not a random position. He knew exactly what this was doing to me. He had me arched and pummeled in a way that rubbed his cock hard against the thin wall separating my ass and pussy and my vision almost whited out when he bottomed out sometimes. 

I felt like I wasn't going to make it. My mind focused down to just sensation and how hot it was when he looked at me like his favorite prey. He was finding all my deepest pleasurable spots, and a pain and pleasure I'd never experienced. We had been fucking long enough that he could tell I was going to a whole new level of sub space.

I thought so many times I was going to tap out, but I was stubborn. Even if it left me broken on the bed, I didn't want him to know it was my first time. I didn't want him to take pity on me.

Occasionally he'd just yell out to my roommate about how wet I was, and tell her how pathetically I was crying. Sometimes she'd answer, but I could barely register the comments. They're vague background memories. I remember her tone sounding pretty amused, which just sent me deeper into the humiliation. My first anal experience was painal, and he was putting on a show.

I didn't want to humiliate myself with failure. Maybe in front of one of them, I could have tapped out, but not both. I white knuckled it and tried to just take it. I couldn't stand the embarrassment of not being able to follow through on my favorite fantasy.

A few times he slowed it down a little, but I could tell it was only to extend the torture and see what other angles or speeds could make me jump and moan. It was only ever a minute or two before he was back to pounding my brains out of my ass.

He held back when I came on his cock, muffling my screams with a rough kiss. I must have driven him over the edge, cumming and clenching around him.

He drove himself in even harder and faster, forcing me into my second orgasm as he neared his first.

The overstimulation sent me right into my third orgasm, so fast it hurt to cum as he just jack hammered my ass. I was still in the middle of it when I felt his hot cum flooding me. Making my orgasm all the sweeter.

I think we barely made it 25 minutes total. It all happened so fast, but also seemed like an eternity. As turned on as we both were, he was trying to hold back and make it last.



By the time he was done with me, I was bleeding from the ass and exhausted, but he made me get up and take a shower with him.

There he fingered his cum out of my ass and shot water up me that was hot and cold.

He practically had to hold up most of my weight by keeping me pinned with his body against the wall as he tortured me.

He did it until I begged him to make me cum or stop. He stopped, intentionally leaving me sleepy and turned on and finally let me go pass out.

He whispered in my ear, "If you want to keep my cum next time, you should be ready for me."

I was so sore and horny from it that I lay in bed masturbating to the ache he left me with for two days. My roommate even helped me shower the next day, because I was still a little shaky and out of it.

I found out I cum just as much from painal as I thought I would. It wasn't a failure, it had been exactly what I needed. I had never felt so full or cum so hard as I did with his cock in my ass.

I stayed in that dynamic way longer than I should have because I loved his rough treatment so much.

I rambled on quite a bit. I know it sounds a little far fetched, but I was basically orchestrating everything I could in my life to make it most likely I'd live out a bunch of my fantasies. Luckily, I live in a major city with a huge kink crowd. So I was able to do just that.

What can I say? Trying to repress my sexuality just turned desire into need.