It was when I felt the head of Greg’s cock settle against my ass that I started wondering whether asking him to fuck me had really been such a good idea after all.
This time, there was no more fabric between us. I could feel it : hot, slick, and damp.
Oh shit... hold on there, rugby boy.
“Ah... fuck. There are condoms in my bag, next to the bed.”
I’d almost forgotten the most important thing: protection.
Greg seemed to have a pretty active sex life, and on top of that, I’d taken two of my roommates’ cocks in the past few days. It was the perfect recipe for picking up something unpleasant.
Thinking about it, I’d really started piling up risky behaviors lately. Swallowing the cum of three guys I’d only known for a few weeks definitely hadn’t been my brightest idea.
But what can I say?
I was starting to genuinely enjoy it.
“Mmh...”
Greg grunted softly: not in frustration, but more like he’d suddenly remembered the importance of that little piece of latex that saved people from all kinds of problems.
I felt him climb off the bed for a moment and rummage through my bag.
I took the opportunity.
“And put some lube on it too, please.”
For a second I almost felt like I was coaching him, as if the roles had somehow reversed.
He didn’t seem to appreciate that.
“I know what I’m doing,” he muttered while digging through my things. “Don’t worry.”
“If I’m your first ass, you’ll need to be careful. Right?”
“Yeah.”
I heard him tearing open the condom wrapper. Julien had definitely been smart to buy the larger size. When I glanced back, I could see just how unusually thick Greg was.
Propping myself up on one elbow, I used some more lube to work myself open a little further, stretching slowly.
I didn’t want to repeat the mistakes I’d made with Adrien.
Especially not with this rugby beast.
Two fingers slid in easily enough. I was still pretty slick (I’d started preparing well before he arrived) but two fingers were nowhere near Greg’s size.
“Ah... fuck,” I heard behind me. “Goddamn...”
Greg sounded like he was losing patience with the transparent piece of latex he was trying to roll onto his hard shaft.
“Need a hand?”
“No!”
The answer came so quickly and sharply it was almost as if I’d insulted him.
A little touchy, was he?
As I continued working myself open, I turned around fully to watch him.
There was something almost adorable about how determined he was to get the condom onto the swollen head of his cock. His fingers kept fumbling. Beads of sweat glistened on his forehead and occasionally dripped down into the middle of the operation. His pecs were contracting so hard behind his tank.
He was so intensely focused.
“Fucking c...”
“Greg.”
“I’ll get it.”
Again, the interruption shut down any further discussion.
Fair enough.
A couple minutes passed. My fingers were beginning to dry out as I kept myself spread open for him. Finally, Greg managed to roll the condom farther down, though his erection seemed noticeably less enthusiastic than before.
“Fuckin’ rubber.”
Maybe he wasn’t used to wearing them?
Still, there was no way I was letting him skip it with me. This was gay sex after all. Plus that dude slept with women far too often for me to take that chance.
“Everything okay?”
“Yep. Get back on your stomach.”
His eyes remained fixed on his cock.
“And spread.”
Obediently, I followed instructions.
The moment felt oddly unsexual, like something from a medical procedure. He wasn’t into me or my body, he was into using my hole at that moment, which felt weird but also kinda exciting in a way.
Being used.
Man-handled.
We were all sex friends here now, in a sense.
He climbed back over me, positioning his thighs around mine before spitting directly onto my hole.
“Go slow, okay?” I reminded him.
That strange sensation of warm latex pressed against me returned.
“Tap if it hurts too much, alright?”
“Okay.”
That code reassured me.
“Going in that pussy.”
And he began to push.
The way we were talking… like commenting on non sexual stuff...
Miles away from anything sex had been with my exes.
Even Julien was more sensual, almost gentle.
Greg, on the other hand, didn’t seem particularly concerned with me.
At least, that was how it felt.
I was a hole.
Maybe not even a man in that moment.
Just an isolated female hole he wanted to use.
Maybe that was why Greg struggled to get further with women.
He pushed several times, but his cock lacked firmness, and that clearly frustrated him.
“Fuckin’ condom... come on...”
As if that were the only issue.
Then it occurred to me that he was still practically dressed. His boxer was barely lowered, he was still wearing his black gym top and his rugby socks.
Maybe that wasn’t helping.
“You know... maybe take off ur clothes? Probably be more comfortable.”
Especially since he was still dripping sweat all over me.
“Shut. Up.”
He grumbled.
“I’m trying to focus. Spread wider and keep your mouth shut, house slut.”
Maybe he needed to imagine something else.
Then...
SMACK
Another slap landed across my ass.
“Moan. Go on.”
What?
SMACK
“Help me. Moan for me.”
SMACK
“Mmh.”
“Higher!”
Jesus.
I hadn’t signed up to be humiliated like this.
The spanking, sure. He clearly enjoyed it, and I wasn’t exactly against it.
But being treated like a girl?
Then again, he was the one who’d talked about calling me Stephanie.
Maybe he needed that.
So, gathering my composure and trying not to focus on how awkward the situation felt, I let out a deliberately higher-pitched moan.
“Mmmmh... yeah.”
“Better.”
His deep voice answered immediately.
SMACK
“Mmm...”
“Come on, baby. Moan for me.”
“Mmmh... more.”
“Yeah?”
SMACK
His hands resumed their assault on my backside.
Those huge palms landed hard and fast. I could already tell my cheeks must have been turning red beneath the blows. And my moans were becoming more genuine.
The game and reality were starting to blur together.
At least the spanking helped him.
After a few solid smacks and a handful of embarrassingly feminine noises that surprised even me, I felt his thick cock harden dramatically and begin pressing much more insistently against me.
“Mmh!”
That one was completely real.
“Easy, Greg.”
“Your little pussy’s so tight, slut.”
A bit of lube landed on my hole.
“I’m gonna open you up properly.”
And then, just as I was about to tell him to ease up on the assault, I felt the head of Greg’s cock finally begin to push its way inside:
POP.
His dick had broken through my ass for real.
That was it.
All three of my roommates had officially fucked me now.
Or at least, they'd all penetrated me, I guessed it was pretty different.
And Greg was definitely not the easiest of the three.
The real challenge wasn't length: it was sheer thickness. His cock was just fat and dangerous. Right now the issue was how much my poor hole had to stretch around the head alone!
“Ouch... fuuuuck.”
I blew out a long breath, trying to ride out the initial pain.
“Stay right there. Come on. Good girl.”
It was nowhere near as bad as it had been with Adrien. Julien’s preparation had clearly paid off.
Still, I knew I was sensitive back there, so I shifted my hands and planted them against Greg’s hips, preventing him from pushing any deeper.
I could feel the power in his body.
The weight of his muscles pinning me into the mattress of my tiny bedroom. Like he used to pin other guys on the field.
This giant had turned me into a small, fragile body, ready to me smashed, face down.
I was his woman tonight.
And somehow...
There was something good about being treated that way.
“Keep it there. Fuck.” I almost screamed.
Greg followed instructions.
He stayed perfectly still, letting the swollen head of his cock stretch my entrance at its own pace.
Feeling him poised there on the threshold of my body was undeniably exciting.
“You okay?” he asked after a moment. “Should I pull out?”
The burning was starting to fade.
I was afraid it would come back, but curiosity got the better of me.
I wanted to know more.
So I gave in.
“No. Go ahead.”
And he pushed further.
Fuck, it was strange.
And painful.
I immediately pushed against his hips again, stabilizing him and preventing him from skewering me with that monster.
A few more centimeters was already plenty for one day.
“Okay... easy. Fuck me now.”
He didn't hesitate.
With one controlled motion, he pulled back until the head of his cock was almost slipping out of me, stretching my small entrance to the limit—
then drove back in.
Right up against my palms.
“Fuck,” he groaned. “So fucking tight.”
I controlled the depth. He handled everything else.
My bed started creaking. Greg let out a low grunt with every thrust. And before I realized it, my own moans had returned. The whole thing became an absurd little symphony.
And the bastard was already speeding up!
Each thrust became sharper.
Harder.
More aggressive.
He wanted more.
I could feel his frustration.
But those first few inches were already more than enough for me.
This was practice.
Practice for taking Adrien’s cock deeper someday.
Well...
if he still wanted me.
“Fuuuck. Such a good little hole, take it.”
My thoughts drifted.
Behind me, the rugby player kept pounding away with heavy, powerful thrusts, making both my bed and my voice squeak in protest.
And we were both lost.
Each trapped inside our own fantasy.
Because Greg clearly wasn't seeing me anymore.
He was imagining a woman.
Imagining my asshole was the best pussy he'd ever had.
“Fuck yeah! Give it to me.”
Meanwhile, I was imagining something else entirely.
I pictured Adrien's cock stretching me open again and again before sliding deeper.
In my fantasy, there was no latex.
No condom.
Just skin against skin.
Like lovers.
Heat gathered low in my stomach.
Then came that familiar sensation.
I was getting close.
Even though I wasn't touching myself.
Greg’s thrusts were enough.
The force behind them made my own cock, trapped between my stomach and the increasingly damp mattress, begin to leak and harden.
God.
This feels so good.
Being fucked like this.
Giving myself to a man.
How can this feel this good?
Above me, Greg’s rhythm was becoming increasingly erratic.
Chaotic.
Then the sounds started.
He was no longer grunting.
He was growling.
Like some animal in heat.
The raw, feral quality of it intensified everything.
He built momentum.
Started bellowing almost like a bull.
And suddenly I panicked.
He's going to come.
He's definitely going to come now!
This was the sounds he made right before covering someone in cum—or making them swallow it.
Thank God we'd used protection.
Otherwise he absolutely would have dumped his load inside me, no questions asked.
At least the condom was keeping me safe.
“Take it, you fucking bitch”
Greg didn't stop groaning or hammering into my stretched-out hole.
If anything, he doubled down while climaxing inside me. He seemed to lose his mind, driving harder and harder, trying to force his way deeper into me.
Fortunately, I still controlled how far that swollen cock could go. And I made damn sure it stayed where it felt good.
“Ghhhh!”
He kept moaning and whining right above my ears. And I felt something almost comforting. Almost reassuring: the feeling of making someone come. The feeling of making Adrien come. Because Adrien was still the one filling my thoughts. And imagining giving that much pleasure to him—just with my body… that opened some unexpected doors in my mind.
“Fuck, yes!”
That one was from me.
Imagining someone actually filling me up.
Like a woman being bred.
The thought was absurd.
Ridiculous.
And yet it was the final drop that sent my internal pressure overflowing. I was going to come without even jerking off. Again.
“Fuck... so good!”
Warm, sticky cum splattered across my stomach as Greg’s increasingly violent thrusts milked more and more pleasure out of me.
“Oh shit!”
Greg’s voice was still breathless from his efforts, but now surprise had joined it.
“Fucking slut! Squeezing my cock with that pussy!”
“Yeeees!”
At that point, there was no pretending to be straight anymore.
I wasn't even finished climaxing before a thousand filthy thoughts started racing through my head.
If this was what it felt like with a guy I didn't even love that much...
Then what would it feel like with someone I truly cared about?
I need to get fucked again.
Very soon.
For a few seconds, neither of us said anything.
Greg started to pull out slowly, the sensation was really weird, like I'd just emptied myself of something enormous, and suddenly I felt a resistance (probably the head of his cock being held at my entrance), Greg groaned and pulled harder while pushing my ass out.
Fuck, he just wrecked me.
And suddenly, SHLACK, his cock finally left my canal.
I caught my breath, my legs shaking.
“Shit.” He simply said, panting.
He seemed focused on something but I couldn’t see a damn thing since I still had my face almost pinned to the mattress, barely able to see the wall before me. However, I I could perfectly feel something big and strange inside me. Something not supposed to be there.
I reached out quickly and felt some rubber texture emerging from my stretched asshole:
“Ghh fuck. Is that…?”
“Let me help.” and my roommate went to grab the base of the rubber, before pulling hard on it. “Shit man. Stuck.”
I tried to push hard too, not sure what to do.
Damn, does that kind of thing usually happen?
And eventually, I felt my ass stretch again, only this time, it stretched around something wet and warm. Like a balloon filled to the brim.
“Fuck. Guess I needed that.”
I swallowed hard, not sure was to do next, my ass still very sensitive. The room felt strangely quiet after all the noise from earlier. Greg was now standing beside the bed, catching his breath. For once, he didn't look like the unstoppable rugby player who charged through life without thinking.
"Well..." he muttered.
I turned my head toward him, a bit anxious about what was coming next. I was able to notice (with some relief) that his now smaller and shiny cock seemed clean, as did the condom swollen with his juice that he had just removed from my bowels.
Good news.
At least, this time, I hadn't made a mess of everything.
Greg dropped the rubber on my bed, right between my feet and seemed to ponder on something:
"Wanna keep it?"
The words seemed to surprise him as much as they surprised me.
Wait what?
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