The Unexpected Hookup Chapter 4 (Patreon)

All characters engaged in sexual activity are 18 or older.

The following night, we hear a knock on the door. Jack opens it to find Jessica standing there in another skimpy outfit. This time she’s wearing a short plaid shirt tied in the middle, right under her boobs, and a pair of denim short shorts. “Hey guys!” she says, seductively twirling her blonde hair. 

Jack’s face lights up and then quickly turns into a frown when he sees my face. I don’t mean to, but I’m pretty sure I’m giving her the dirtiest look I can manage. 

Since it’s the weekend, we had spent the entire day hanging out together like normal, playing video games, getting food, and when we were alone, making out and jerking each other off. 

As far as perfect days go, this one was as perfect as it gets. Just me and Jack doing things that boyfriends would do. Except that we’re not boyfriends. He’s still straight. This thing between us is just for fun. ‘Brojobs,’ he called it. It’s purely a physical thing we’re doing. At least for him it is. 

All day long, the walls I’d put up over the past couple of years were torn down like they were made of paper. It took less than twenty-four hours to undo four years of work and discipline. 

So I really shouldn’t be upset that he’s happy to see Jessica. He’s still straight. He still wants pussy. Good for him, I guess. I wish it were that easy for me. I don’t think I can ever go back to women now. Not after I’ve had a taste of my best friend. 

I get up from my bed, try to push past them, and mutter, “I’ll give you two some space.”

But a hand grabs my wrist. My heart skips a beat, but when I see it’s Jessica holding me back and not Jack, my heart feels like it’s cracking. “Wait,” she says, “I wanted to talk to both of you.” 

The confusion must be clear on my face because she laughs and Jack guides me back into the room, his hand on the small of my back. 

“So I wanted to say that I feel terrible about last night. But I want to make it up to you both tonight.” She pauses and ties her hair back into a bun. “Unfortunately, Rachel couldn’t make it, but I would be willing to let both of you fuck me… if you’re willing to do something for me first.” 

My jaw drops open at her words, and Jack looks vaguely uncomfortable. He clears his throat. “Uh, what do you want us to do?”

Jessica gets that seductive look on her face again. “I want the two of you to fuck each other first, then you both can take turns fucking me.” 

Now Jack’s jaw is hanging open. 

“I’m sorry, what? You want us to fuck each other? Do you have some type of kink where you get off on seeing guys with each other?” I spit out. 

We can’t do this. I mean, I want to. God knows I want Jack’s dick in my ass, but I can’t imagine that he would want to. It’s one thing to kiss and suck each other off, but actual sex takes it to a whole other level. 

“Okay, we’ll do it,” Jack says.  

My head snaps to look at him. “Jack—”

“It’s okay, Ez. I don’t mind.” He smiles, his eyes silently trying to reassure me. I nod. This isn’t how I wanted this to go at all, but part of me feels good knowing that Jack’s dick will be inside me before it’s inside her. It’s the small things in life. 

He steps up to me, his strong hands cupping either side of my face, our eyes locking. We haven’t talked about what this is. What it means for either of us, but the way he’s looking at me right now is not nothing. “Do you trust me?” he whispers. 

I nod again because apparently I’ve lost the ability to speak. He doesn’t hesitate after that. His mouth smashes into mine, our lips melding into one before his tongue seeks entrance into my mouth. I let it, and even though we’ve kissed dozens of times today, it still feels like I’m floating on Cloud Nine. 

He tugs at the hem of my shirt and pulls it over my head, the cool air causing my nipples to pebble. We quickly shed the rest of our clothes, while Jessica makes herself comfortable on my bed. 

Jack has me lie on my back and peppers kisses down my body, stopping to suck on my nipples, gently biting at them before soothing away the sting with his tongue. He keeps going, his tongue tracing the divots of my abs until he reaches my dick. 

His eyes flick to where Jessica’s watching with rapt attention before settling back on mine. He looks nervous, so I give him a small smile that seems to reassure him. His tongue laps at the bead of precum collecting at the tip, causing me to groan and thread my hands into his hair. 

The wet warmth of his mouth engulfs my cock, tongue swirling around the head and then works his way down until the blunt head hits the back of his throat and makes him gag. He pulls off with a pop, eyes blown dark with want.  

I didn’t think he’d do that in front of Jessica, but he did. He surprises me again by pushing my hips until my hole is exposed to him. No one has ever seen me like this. 

Jack licks his lips, breath ghosting over the sensitive skin. There’s no way…

His mouth is on my most private area, licking it like an ice cream cone. “Fuuuck, Jack!” I groan loudly. He doesn’t answer, but he looks up while his tongue pierces the ring of muscle, and the sight of him eating me out like that almost makes me come on the spot. 

Jack keeps at it, licking and sucking on the skin for a while until my hole is a quivering mess. He grabs some lube from his nightstand and clicks open the cap. Cold drips onto my clenching entrance, causing me to gasp. 

“Sorry,” he mutters, giving me a sheepish smile. He works me open, one finger sinking in easily after all the work he just did with his mouth. 

I can’t believe Jack just ate me out. I’m not sure what’s going on with him, but even in my most depraved fantasies of him, I never imagined that he’d do this with me. 

Jack slides in a second finger, stretching me open with care and concern, his eyes never leaving my face. He curls the up and hits my prostate almost immediately, as if he knew exactly where it would be. Precum pours out of me, pooling on my abs as he massages that spot. 

“Jack, I’m going to come if you keep doing that,” I tell him through gritted teeth, trying my hardest to last. I can’t come yet. Not until his dick is buried inside me. 

He pulls his fingers out and my hole clenches, missing the feel of him. “Are you sure you’re ready? I can—” 

“I’m ready, Jack. Please fuck me.” 

He nods and slicks his cock generously before applying even more lube to my hole and crease, making everything slippery. The blunt head presses against my entrance and then slides in with surprising ease. I’d heard that it hurts the first time you take a dick. It’s the only reason why I hadn’t done more than finger myself until now. 

It’s like his dick is made for me, the way it’s sliding in, nice and easy until he bottoms out, hips pressed flush against my ass. Then my hole clamps down on his dick like it’s greedy for more. 

“Fuck, Ezra, you have the tightest hole,” he says, tightening his hold on my hips. 

I hear a moan and look over to see Jessica completely naked and fingering herself. Seeing a hot girl naked on my bed should do something to me, but annoyance flares through me instead. The gall of her to think that she can fuck my man. 

Jack strokes my dick in rhythm with his thrusting hips, slow and steady in a way that says he wants this to last just as much as I want it to. He teases the head of my cock each time he bottoms out and uses the copious amount of precum leaking from me to make a smooth glide. 

My body is completely in tune with his. Each breath he takes, the way his abs ripple when he slides out, the feel of his dick inside me. There’s no way I’m ever going to have sex with a woman after this. 

Jack speeds up, his hips pistoning into me, the slap, slap, slap of our bodies colliding and the squelch of his hand on my dick fill the room along with our pants. Each thrust of his dick brushes over my prostate, and I lose the battle. I come with an intensity I’ve never felt before, my dick exploding all over my abs and chest, one rope of cum even hitting my chin. 

Somehow my hole clenches even more on Jack’s dick and he starts blabbing, “Oh, God, that feels so good, Ez. You came on my dick like a good boy.” He buries himself to the hilt one last time and shudders. I can feel him pulsing inside me, filling me up with his seed, breeding me, claiming my ass as his property. 

When he’s finally done, he slips out and a trickle of his cum leaks out and drips down my ass until it lands on the sheets beneath me. Jack collapses beside me, both of us breathing hard like we just got out of practice. 

“Fuck, that was so hot. I’m like totally ready to go right now.” Jessica is standing over us, still naked. “Which one of you wants to fuck me first?”

Jack looks at me and then back at Jessica. He must see the truth in my eyes, because he says the most unexpected thing to her, “Nah, I think we’re gonna pass. Turns out we both like dick a lot more than we realized.” 

Jessica’s mouth drops open, but her face quickly goes from shocked to pissed off. “Whatever, it’s your loss.” She quickly gets dressed and storms out of our room, finally leaving the two of us alone. 

I turn back to Jack. “Did you really mean that? About liking dick more than you realized.” 

Jack grins. “I don’t know if I like dick in general, or just your dick. But honestly, I’m okay with not knowing. All I know is that your dick is more than enough for me.” 

He leans in and kisses me softly. I don’t know what this means for our future, but I’m going to hold on to him for as long as I can. 

The End.