I'm not even going to ask because I think it's obvious AF as to what the title is implying.
Sterling
"Join us," Kelsi reiterates.
"Uh...Jackson...?" I stammer, sliding my gaze over towards him. I am not one to fluster easily, unabashedly stripping down to my underwear in drinking games or freely making out with girls at parties, but this invitation leaves me speechless.
It's not everyday that one gets invited to participate in the sexual escapades of their love interest and his crush.
Again, he shrugs. "It's really up to you-"
"Okay," I find myself agreeing. "Then I accept."
Fuck it. It's the summer and it's Jackson. I repeat, JACKSON. I can only guess if I will have this opportunity again and even though it requires me to share him, something is always better than nothing.
With a nervous laugh, I plop down onto the daybed, unsure of how to proceed. Do I kiss him? Do I wait for him to make a move?
Kelsi is the one that provides that answer, instantly reaching out to fondle both my breasts with her palms. She nods approvingly.
"Oh," I murmur, caught off guard. "I guess we are just jumping right into it then. My gaze drops to her thumbs as they begin stroking my nipples.
I pull back briefly to yank my shirt over my head, exposing my bralette. Her sights travel to my half-bare chest and she leans in to plant a kiss atop the skin of my décolletage. Her mouth is hot on my flesh as she works her way up towards my throat.
"You are so beautiful," she whispers.
Her lips find my own and my response is to dig my fingers into her wild curls and pull her in closer. As her tongue parts my mouth, Jackson clears his throat.
He wants in on the action but it's hard to forget that he's there. He's always in the back of my mind as I eagerly await him to express any interest in me. The sound is the only encouragement I need to immediately include him.
Without breaking away from Kelsi, my hand grapples across the bed until I make contact with his thigh. It's firm and I begin massaging his leg, mustering up the courage to seek what I am really after.
With shaky fingers, I keep going until I have located his arousal. I gently cup him before stroking his shaft through the fabric of his pants. The moan that falls from his lips is even more seductive than the ones that I have envisioned in my fantasies.
I shift my face away from Kelsi to glance over at him as I continue to rub my touch up and down his erection. Our eyes lock and an electric heat simmers between us. His expression is dark with lust, silently commanding me to come closer.
I am obedient.
I am aware of Kelsi's fingertips trailing down my spine as she works to unclasp my bralette but it is Jackson's movements that I am solely focused on. His hands brush over my breasts and down to my crotch. He is gentle, unsure if groping his sister's best friend is forbidden.
However, even if it is taboo, I don't care. I am Sterling Holloway and I am reckless.
Pressing my palms to either side of his face, I shift to straddle his lap, feeling his fullness against my most intimate regions. The barrier of our clothing acts as a tease. But even though I have fantasized about this exact moment for years, I am in no rush to shed my panties and feel him inside of me. I want to savor every sensation while it lasts.
With a low growl, he closes the gap in between our lips, working his on mine in a feverish manner. My toes tingle with the high of getting to freely run my hands down his chest, taking in the hardness of his muscles.
A sudden impatience grabs hold of me as I quickly work to undo the buttons of his dress shirt. His top falls off his shoulders with ease. I marvel at the taut contours of his torso and can not resist dragging my tongue all the way from his pecs down to his navel.
He shivers and Kelsi is suddenly in my ear, whispering huskily, "Hey, what about me?"
I am reluctant to let Jackson go but I know that I will return. With a nudge of my palm, I push her back against the daybed. Somewhere in the midst of making out with Jackson, she has taken off all her clothes except for her panties.
She writhes as she anticipates my next move and I press my lips to her belly, her porcelain skin silky. I plant light smooches in a path from her abdomen to her inner thigh. From my peripherals, I spot Jackson slipping off his pants and boxers.
I am tempted to gawk but tell myself that I will have the opportunity to shower his stiffness with attention later. As I begin sucking on the fabric of Kelsi's satin underwear, Jackson starts to pleasure himself.
I push aside her panties, my tongue connecting with her slit and I raise my gaze towards Jackson's. If he wants a show, I am more than willing to give it to him. He swallows repeatedly, his breathing growing heavy. It turns me on to see him so immensely affected by my actions.
"Oh, Kelsi," I moan for good measure and he sucks in sharply through his teeth, his eyes widening.
Whimpers sound from her as I continue to go down on her. It's my first time pleasuring a female in this manner and I note that she tastes sweet. Jackson catches my eye and the desire in his heated gaze is enough to have me lunge towards him, leaving her completely forgotten.
The kisses that he greets me with are purely uninhibited and his lips greedily mark my face, neck, and chest. He flings my bralette aside as he brings my nipple to his mouth and sucks. Ecstasy encompasses my nerve endings.
His touch on me is magnetic and no matter how he tries to fight it, the pull is too strong to resist. Now, I am the one being pressed against the pillows as he hovers above me, his hands all over every inch of my skin.
He reaches down to tug off my panties and instantly, we are both in the nude. With urgency, he palms my wet sex and closes his eyes, getting lost in the slick sensation of my inside.
He lowers himself onto me and clings to my form for a moment, allowing me the satisfaction of feeling his erection in between my legs. But he does not enter me just yet. Instead, he teases me with a slow gyration, the aching intensity to have him completely building in my groin.
As the rush of yearning grows too strong for me to fight any longer, Jackson rocks back on his heels to slip a condom on. That is when Kelsi moves in from behind him, wrapping her arms around his shoulders before cupping his chin to lure him to her for a searing kiss. He entertains her for the briefest of moments but quickly returns to me.
There is no hesitation as he plunges himself inside my moist opening and I gasp at his solid fullness. I am not a virgin but the feeling is unlike anything I've felt before. I grip onto the bed as he begins to thrust.
His heart is pounding rapidly when he presses his body to mine, the perspiration on our skin mingling. But he doesn't stay with me for long, slipping himself out just as quickly as he entered. The only part of him that lingers as he moves away, are his lips.
While we kiss, I lay there with my legs spread, an open invitation for Kelsi to do as she wishes. She readily accepts, stroking my folds with her hand before fingering me. She soon replaces her touch with her mouth, swirling her tongue around my nerve endings.
In between her oral action and Jackson making out with me, I am about to come undone with sheer unadulterated bliss. But the two don't spoil me for long. Eventually, they make their way to each other and it is I who is now the spectator.
I expect to feel a pang of jealousy upon watching them fuck but instead, I am hypnotized by the rhythmic movements of their bodies and Jackson's arousal moving in and out of her. The sight makes me wet and I guide my touch between my legs to begin playing with myself.
I am lost gratification when Jackson returns. With a press of his lips to Kelsi's forehead, he removes himself from her and glances over at me, his eyebrows shooting up in a come hither gesture.
I push him onto his back, straddling his hips so that I can ride him. As I rock my hips, Kelsi approaches me from behind and kneads my breasts while she sucks on my neck. Jackson's hands slide up her legs to cup and squeeze her butt.
We are all on the cusp of orgasm, prompting Kelsi to move to sit on Jackson's face as he continues to penetrate me. His mouth works over her sex and while she and I are face-to-face, she leans in to capture my lips for a steamy kiss. My body buzzes over how unbelievably hot the whole scene is.
Never in my wildest dreams would I have ever envisioned myself engaging in a threesome with my best friend's brother and his crush.
I am the first to lose control, crying out as my body tremors in a dizzying crescendo. I can feel Jackson's excitement pulsating inside of me and know that he has followed suit. Then as Kelsi wraps up our shared experience, I collapse onto my back with panting breaths.
Jackson's skin is slick with sweat and he gazes up at the night sky, a dazed and dreamy expression on his face. Kelsi falls into a resting position beside me, trailing her fingertips over the outline of my hips. She is the first to speak.
"That was incredible," she awes. Jackson murmurs his agreement.
"Sterling, you were amazing," she continues. "If you ever want to hook-up again, just the two of us, let me know. I would definitely be game."
Jackson lifts his brows but he doesn't comment on her statement. Finally, with a sigh of contentment, she lifts herself up and begins getting dressed.
"Unfortunately, I have to go," she announces. She quickly puts her clothing back on before leaning in to give me a peck on the lips. "Call me," she mouths.
She turns to jog back up the gravel path and disappears into the darkened meadow, leaving Jackson and I alone.
He exhales but doesn't immediately acknowledge me. "I can not believe that just happened," he says at last, dragging his hands down his face.
"How did I go from being this dull man that eats his vegetables and spends ninety-percent of his waking day playing violin to someone that eats a girl out while another is riding his dick? This so isn't me."
I shrug, a bit shocked myself that he and I just had sex. "Perhaps, you're going from one extreme to the next but isn't it obvious that you aren't happy with the you that you've always known?"
He glances over at me and my arms prick with goosebumps as I recall how he looks when he's in the midst of passion. "Sterling, I have to admit that this past week is the first time that I've been able to experience an ounce of fun in my life and I think I owe that all to you."
I beam, my insides glowing like the light of a firefly. "Naturally," I agree, giggling. "It's hard to be in my vicinity and not get sucked into having a great time."
He smiles at me sheepishly. "I also believe that I owe you an apology. Truth be told, I always found you annoying as hell."
Ouch. Well, give the rejection to me straight, I guess.
He shakes his head. "But now, I'm realizing that you only got on my nerves because of how uptight I was. You've encouraged me to loosen up these past couple of days and I feel more...free. So, thank you."
I give him a pat on the chest. "It's the post-coital high talking."
He grins in response. "Yea, that feels pretty fucking fantastic too."
Abruptly, he drags his hands down his face, a deep rumble of laughter causing him to shake. "I'm so dumb though," he continues.
I lift a brow.
"It's glaringly obvious that Kelsi is into you. She barely acknowledged my presence while we were all having sex but she couldn't keep her hands off you." He chuckles even harder. "She actually requested a repeat with just the two of you, right in front of me. I guess that squashes that crush for me."
I nod. "I have to confess that I'm definitely interested in making it a twosome as well."
Jackson smiles as he thumps my arm. "You have my blessing. She's clearly only hot for you."
For the first time, I don't hesitate to tell him what is on my mind. "Then it's a shame for her that the twosome I'm referring to is me and you."
Question of the day: How do you think Jackson will respond?