05 | three’s company (M)
“Are you sure you wanna do this? There’s no pressure, we can go back to chilling if you want.”
Jackson’s voice was gentle, and his hand gripping my chin was even gentler as I stared up at him from the bed. I had already made up my mind, though.
“It’s okay, I want to keep going.”
Both Jack and I turned our heads in the direction of the sound of a third voice. My best friend Caleb. He sat in an armchair by the window across from the bed.
It was getting late in the day and the sun was setting beautifully. Subtle rays of orange light peaked through the blinds, casting warm shadows on Caleb’s pale skin. He looked amazing in so many ways... ways that would have never crossed my mind before this day.
His chest was on display and he was very well erect if the obscene bulge in his shorts was anything to go by. I couldn’t believe I was seeing him like this. I couldn’t believe I was about to engage in a threesome with two of my closest friends.
But as much as I tried to feel guilty about it all, I couldn’t. My excitement overpowered any doubts I had. Besides, I was doing this with people I trusted. If anything went wrong I felt we would easily recover from it.
To think this all stemmed from an innocent game of Never Have I Ever.
The bed dipped slightly as Jack finally joined me on it.
“I won’t do anything until you tell me to,” he said.
We were next to naked. No stopping now.
“I’m ready. Give me your worst, or uh- best. I don’t know. Give me something.”
I wanted to punch myself in the mouth for always talking so much, but seemingly unbothered by my rambling, Jack dismissively shook his head with a laugh.
“You’re quite adorable, you know that?”
Without saying another word, he gently pushed me onto my back. He straddled me and searched my eyes for any signs of apprehension. When he found none, he lowered his head and shortly after our lips met in a fervent kiss.
He hiked up my right leg, pressing himself roughly against my core. I felt all of him and if this was what he’d be giving me — well, I don’t think I’d be able to wait very long to have it.
My hands were in his sable curls, tugging eagerly. I might have tugged a tad too hard because he sharply rocked his hips against me. I whimpered, loving the feeling. However, I couldn’t help but feel like Caleb was being neglected.
“Wait, what about you?” I pulled away from Jack, looking over at my best friend.
The worry I felt quickly vanished. Desire took its place, swirling in my stomach when I discovered he was palming himself over his shorts. He let out the softest of grunts, his hooded eyes firmly fixed on the sight before him. It was almost as if he were in a trance.
“Focus on Jack.”
But I couldn’t. I couldn’t peel my eyes away from Caleb. The way he touched himself- I could watch all day, but there were other plans for me. It wasn’t long before I was receiving a little help with doing what I was told earlier, a familiar hand on my face.
“Look at me.”
Jack’s baritone voice was firm and I felt my lust seep out and further saturate my panties at his command. I stared into his melted chocolate brown eyes that never left me. His right hand slipped from my chin when he was sure that I wouldn’t turn away, and started a trail from my calf, inching upward slowly.
When his fingers slipped underneath the band of the delicate fabric of my panties, he began massaging my sensitive bud with his thumb. The fairly even breaths leaving my mouth became shallow and moaned. I couldn’t stop myself from rocking against his hand.
“You’re a needy girl, huh?”
In response, I unhooked my bra and then raised my hips off the bed. Jack stripped me bare, tossing my garments aside. If possible, his dark brown eyes seemed to have darkened even more, laying his eyes on my slick pulsing center.
I started to speak, but was abruptly cut off when he pressed his soft lips in a kiss right on my bundle of nerves. My breath was caught in my throat. I’ve never had a guy go down on me before. He gently took one of my hands, put it atop his head and whispered:
“Pull if it feels good.”
That sentence alone was almost enough to put me over the edge.
He tasted me with slow kittenish flicks of his tongue that had me bucking my hips up into his mouth. As his speed gradually grew faster my body seemed to spiral less and less out of my control. I was a quivering mess when he latched onto my clit and began sucking with ferocity. My cries of pleasure filled the otherwise quiet room.
“Jackson... oh, Jackson! Ah!"
I was so close and he got me there so quickly. My fingers weaved through his locks, pulling, making him move even faster. Faster than I could handle. It wasn’t long before I came, his tongue still swirling, lapping and teasing. He never stopped but instead slowed his pace, allowing me to ride out every second of my high.
“God, I love hearing you like this,” Caleb commented. His voice was low and gravelly.
Chest heaving, I turned my head to see him enclose his hand around his sizable cock and grip it tightly. His shorts were now pushed down over his hips. He shuddered and dropped his head, causing his shoulder-length honey blonde hair to curtain his face.
“Eyes on me,” Jack reiterated. “Tell me what you want.”
What did I want? I wanted a couple of things. One, Jack inside of me. Two, Caleb’s cock inside my mouth. I felt my body overheating with lust and something needed to happen. Fast.
“I want both of you... Jack fuck me, please.”
Like Caleb, Jack was already shirtless and when he pulled down his boxers with his jeans, I involuntarily clenched. He wasn’t too big but his girth scared me. I watched as he stroked himself a few times before settling in between my legs.
The bed dipped again as Caleb knelt beside me, his cock red and throbbing right next to my face. It only took a tilt of my head to take him into my mouth. In the same instant, Jack pushed himself inside of me. It felt like he was gonna rip me apart. He filled me to the hilt, waiting a few seconds before pulling out and plunging back in.
“Shiiit,” he groaned.
I moaned loudly as Jack fucked into me like a man untamed, the vibrations from the back of my throat making Caleb twitch. He gently gathered my hair into his fist as he thrust rhythmically in and out of my mouth. His feel was soft like silk and his taste was sweeter than any candy I’ve ever tasted. I opened up wider to take even more of him.
“Shay... fuck. I’ve always loved your mouth. So pouty and smart. I love it even more right now.”
Caleb’s pace was steady, but he hit the back of my throat making me gag. I pulled away, gasping for air. He brushed a few wild, sweaty strands of hair from my face as he looked down at me.
“You have no idea how good you look taking Jack’s dick. You like that?”
With a frantic nod of my head, I responded. My second climax was well on its way and I knew it would hit with force.
"Yes! Oh god, please.”
One of Jack’s hands firmly gripped my waist as the other squeezed my left breast. His hips never wavered. A million tiny bursts of white light exploded behind my eyelids as I came with a scream, my fists balling up the sheets, legs shaking and back arching off the bed.
Caleb’s lips trailed feathery kisses along my jaw and then brushed against my ear as he whispered his praise to me.
“You did so well... you think you can come one more time for me?”
I gave him a tired, but eager smile. “For you.”
Jack pulled out of me and left the bed, taking Caleb’s original place in the chair. He watched us as he used his hands to get himself all the way there.
My best friend hovered over me, staring for what seemed like hours. Before I could ask what was wrong, he sunk himself deep inside of me and swallowed my moans with a kiss... a kiss that very much contrasted from Jack’s. He was slow, attentive and tender.
The rock of his hips was also slow, yet deliberate, and those gorgeous hazel eyes bored into mine. I felt the entire atmosphere change. Apparently I wasn’t the only one.
“Uh, I think I’m just gonna take care of myself in the bathroom,” Jack said.
Neither me nor Caleb responded. We were lost in each other. He placed my hands above my head and then interlocked our fingers, squeezing. This time around I was lifting my head from the mattress to meet his plump lips.
“Caleb...nngghhh,” Our mouths separated as I groaned against his shoulder.
“You feel so good. So soft... so warm. I don’t want this to ever end.”
But just like that, it did. I clenched especially tight around him, causing his hips to stutter as he spilled his hot cum into me.
Caleb unlaced his hands from mine and secured them around my waist, holding me close. Our breaths mingled, coming out in shallow pants as we stared back at one another.
“Are you okay? This wasn’t too much for you was it?” he asked sincerely.
I nodded. “No, it was fun... I’m okay, more tired than anything. Got any Gatorade laying around?”
He chuckled lightly, resting his head against one of the fluffy pillows on the bed. He looked so beautiful; a completely blissed out, sexy mess he was. I don’t know what came over me but I couldn’t stop myself from leaning forward.
What surprised me is that when my lips met his again, he kissed me back even harder. It all felt so much more intimate than the sex we just had. The feeling made my heart knock violently against my rib cage.
He was still very much inside me as his hands left my waist to tenderly caress my cheeks. I kept them there, not wanting to lose the warmth of his fingertips on my skin.
I know I said we’d be able to recover if anything went wrong, but developing a sort of emotional ache for my best friend isn’t what I expected to happen. Maybe it was just the heat of the moment, but I never wanted to leave his arms.