How about medium well

“Did you clean yourself back there yet?” Heather calls from her room as Bowen is in the bathroom

Bowen flushes deeply, his heart pounding in his chest. He looks at himself in the mirror, his reflection showing a mix of embarrassment and curiosity. "Yeah, I did," he calls back, trying to keep his voice steady. He finishes wiping himself and walks back into Heather's room.

He couldn’t believe he’s doing this, what would his teammates say? He should turn back now and maybe just pay for a nice dinner in exchange….but as Bowen opens the door he spies Heather sitting in her bra and pajama shorts…the ones that ride up her ass to the point you question if it's just underwear at that point

Immediately Bowen’s earlier thoughts of turning back are forgotten. He steps into the room, closing the door behind him with a soft click. "So... um..."

“Oh what happened to that brave machismo man from earlier” she chuckles “What happened to the slut that was latched to my vag like a kid to a popsicle.”

Bowen's face burns a little, with a sort of postal oral clarity at his earlier, as Heather put “horny fucking vacuum” escapades flashes his mind. The memory of his face coated in her sticky, wet juices makes him squirm.

"Shut up," he mutters, his voice lacking its earlier confidence. "That was... different."

“Then let’s see how much you like different,” Heather says as she pats the bed for Bowen to lie down “because I’ve also been wanting to try….different”

Blwen hesitates for a moment, knowing full well what she means by 'different'. His muscles tense as he slowly walks over to the bed before lying down stomach first on the covers. "What exactly..."

But before he can finish Heather pulls down his briefs causing him to yelp. She stares as the pale globes of flesh back at her. The same one she had secretly fondled just last week.

"Heather... you can't..." he trails off, his voice trembling slightly.

“And why not” Heather says as she lightly slaps one cheek “You get to play with my nether regions it’s only fair I do the same,” she says as he fingers dip down to spread his cheeks

Bowen's breath hitches as Heather's fingers spread his cheeks, a cold draft hitting his most intimate area. He clenches his muscles involuntarily, feeling a mix of embarrassment and unexpected arousal. "Heather... wait..." he tries to protest weakly, but his voice lacks conviction.

“Shhh, relaxes, Bow” Heather says as she lets go of his ass cheeks letting them spring back “I’ll take it slow”

Bowen takes a deep breath, trying to calm his racing heart. He lies down on the bed, his body tense but compliant. He watches Heather over his shoulder, a mix of apprehension and curiosity in his eyes. "Okay... just... go slow," he repeats, more to himself than to her.

“Mmmm” Heather replies as she squirts a bit of lube onto her fingers “Slow as molasses,” she says as she rubs her fingers to warm the lube up.

Grabbing one cheek she pulls it to the side and begins to dip her finger in, rubbing his perineum.

Bowen closes his eyes tightly as Heather spreads his cheek and begins to massage his perineum with the warm, lubricated fingers. The sensation is foreign and intense, sending shivers down his spine. He bites his lip, trying to suppress a sound. "Oh god..."

Strangely Heather doesn’t dip a finger right away. Instead, she spends the time to thoroughly coat every wrinkle of his rim in the lube. The odd attention to detail confuses Bowen.

And his confusion only grows as Heather takes her time, thoroughly coating his rim with lube instead of immediately pushing a finger inside. The sensation is strange, but not unpleasant. He wiggles a bit, his body unconsciously trying to chase the feeling. "What are you...?"

And then he feels his flesh start to heat up a bit…. growing sensitive.

"What the f--," Brent mutters., his body tensing slightly. He feels the area around his rim growing sensitive, almost tingly.

“Had to make sure your body would really like it” Heather whispers. “So I'm using the one aphrodisiac lube you experimented on me a couple months ago, remember?”

Bowen gasps softly, the heat and tingling intensifying at the mention of the aphrodisiac. He feels his heart rate quicken, his body responding to the foreign substance. "God... Heather...is this really the time to try stuff….like that?" he asks breathlessly.

“Well, I thought I’d return the favor” she coos……as she finally finally dips a finger inside.

Bowen tenses slightly as the finger enters him. As expected there was initially a twinge of discomfort, but soon he felt the heat take over as a new sensation coursed through his body.

"Holy shit," he hisses softly, his muscles relaxing. The aphrodisiac was making his body way too responsive.

“Mmmmm you like it babe” she teases as she swirls the finger around enjoying the way Bowen’s muscles unconsciously contracted around her touch.

"T-too much," Bowen breathes, his body squirming slightly. The smallest touch felt like electricity. He could feel his muscles tightening and releasing on their own, his hole fluttering around Heather's finger. "Heath-..." he tries to speak only for a twitch of muscle to cut off his breath.

“ Hmmm, you seem to be feeling it…Then. let’s. try. two fingers.” Heather punctuated each word as she thrust in a second.

Bowen’s eyes widen as Heather slides in a second finger, the sensation overwhelming. He lets out a low moan, his body arching slightly off the bed. The aphrodisiac had made him incredibly sensitive, and every movement of her fingers sent waves of pleasure through him. "Oh god... Heather…”

“Two fine? Well then let’s try three”.

Brent's breath hitches as the third finger enters him, stretching him open. The sensation is intense, bordering on pain, but the aphrodisiac turns that pain into manageable pleasure. His thighs twitch unconsciously allowing Heather easier access "Fuck... three fingers... Heather..."

“At ease baby,” Heather says as she grabs his shoulders to steady him… “you almost ready to try the real thing”

"Baby... wait..." Bowen moans softly, his body writhing slightly. The aphrodisiac was making him way too sensitive. He could barely handle three fingers, what would her dick er’ clit feel like? "You serious... baby? Three fingers barely fit..."

“Hehe well, unlike your massive hog,” Heather said as she swirled her fingers and proceeded to scissor his inside causing Bowen to let out another strange unwanted sound

“My clit is only like 3 inches anyways, I think”, she says as she flips her hair behind her shoulder to get it out of the way.

Bowen swallows hard, his focus locked onto Heather's movements. The thought of her 3-inch clit entering him sends a shudder down his spine. He's never bottomed before, and the idea of taking something that size, no matter how small, is both terrifying and strangely arousing. "Only... only 3 inches?"

“Mmmmm but who knows each time you munched on it, it grew a little” she chuckled

Silence descends on Bowen and his eyes widen as he processes Heather's words. Hiis mind racing with thoughts of her clit growing each time he sucked on it. The idea is both embarrassing and incredibly hot.

However Heather didn’t seem to notice as she was to focused on rubbing Bowen walls, coating every rim with lube,

“They're all prepped,” she says as she removes her lube-covered fingers.

He feels her removes her fingers, his hole strangely feeling empty and aching. "Heather... wait..."

“What is it baby boy,” she said even as her hips rise to angle her enlarged clit to his back entrance.

"Baby... are you... fuck is that thing even 3 inches anymore?!" Despite his words, he feels a new wave of lust wash over him, knowing he's the cause if said growth. His hole throbs at the sight of it. "...Is it going to fit?"

“Oh shut up you’ll be fine” Heather huffs getting annoyed at her over 6ft boyfriend's constant hesitancy “And yes I think it’s still 3 inches,” she says as she lightly slaps one ass cheek

Brent grunts in reply, not from the slap but the sensation of his hole clenching tightly at the unexpected sensation. He feels a mix of embarrassment and arousal at Heather's annoyance, knowing she's right about him overthinking. "Fuck, okay... I'm sorry, just... just give me a second."

“Like you did to me when I told you to stop outside earlier” she retorts

Heather's words hit Brent like a flyaway football. Fuck, she's right; he hadn’t exactly been the most patient of boyfriend back outside… or these past few days for the matter.

Bowen swallows hard, his jaw stiffening. “ Okay okay, you may have a point but just…just wait a bit ‘kay?"

“I'm waiting,” Heather says as her nails gently rake over his ass. She watches the pale skin pinken underneath her before returning back to normal.

"You know... you're not making this easier." He chuckles softly as her nails roam over his ass. His hole puckers and unpuckers, his body preparing subconsciously. "Heather?"

“Yes?”

Bowen looks back to Heather over his shoulder "Can you... can you just push the head in? Like, just the tip? So I can get used to the feeling?" he asks, biting his lower lip nervously."Please?"

Heather stares before chuckling “As you wish baby boy” she soothes as she grabs his hips and proceeds to angle her clit “I don’t really have a ‘tip’ like you guys but I get the drift” and slowly she starts to insert her member inside

And as the head of Heather's clit pushes in, Bowen lets out a soft gasp. The feeling is intense, unlike anything he's ever experienced. It's a mix of this weird intense pleasure, like taking an intense shit, only the content was coming in not out. Initially, all Bowen could feel was just pressure mixed with pain, like trying to push yourself into a painful stretch.

But just like an intense stretch eventually the pain gives way to more… satisfactory results.

Bowen finds himself pushing back slightly, wanting something more. "Fuck... that's..."

“You like that boy” Heather chuckles darkly “Well why don’t you set the speed,” she says as she squared her thighs and planted her feet on the covers. “Go ahead and push back....see how much you can take”

Bowen’s heart races as he listens to Heather's instructions. He takes a deep breath, then slowly, ever so slowly… he starts to push back. He feels her elongated clit sliding into him, stretching him out and penetrating virgin walls.

God, is this what women felt when men entered inside them? Is this..is this what Heather felt when he first took her virginity? And he was arguably much bigger so it probably explained the tears she shed that night.

He stops when he feels her hips press against his ass, her dickclit fully seated inside. "Holy fuck..."

It’s only 3 inches but it might as well have been a heifer with the way it spread Bowen’s virgin anal walls.

“Oh god you're… you’re gripping me so tight” Heather moans.

“a-and you” Bowen can feel his inside squeeze tightly at his words "Fuck... feel so big.”

“Oh Gawd” Heather nearly yowls as she nearly loses balance and orgasms right then and there “Re-relax your walls Bowen ” she huffs “It’s too tight”

Taking a deep breath, Bowen tries to relax his inner walls, but it's harder than prying a pickle jar open. He's never felt anything like this before, and his body is tensing up naturally at the foreign intrusion. Not to mention the thought of his insides making Heather lose control only served to..

“Eep too tight!” Heather yelps as she jerks out, the bed rustling a bit as she plopped down onto her butt

More strange sensations seemed to emanate from Bowens rear, he could feel the asshole puckering a bit at the sudden loss of fullness. An emptiness emanating from his backside.

Quickly Bowen turns around, his face flushed and his bottom feeling oddly sensitive. "What the fuck was that?" He asks, his voice shaking slightly.

He wants it back…the fullness of his body, well it didn't crave it exactly… but maybe just wanted to savor the feeling a bit more.

“I was- I was about t-to come” Heather stumbles out face flushing red. “Gosh is it always like this?”

He looks up at her, his eyes filled with a confused desire. "You mean... is it always feels so intense being inside someone? Well yeah of course”

“It felt like a vise grip” Heather breathes as she slowly rises back up to her knees and angles her clit again “an-and I felt like I was about to orgasm….no ejaculate at any minute” she finishes starting at Brent’s eyes intensely

His breath catches at the sight of her position and the feel of her member almost entering him again. He bites his lip, trying to maintain an ounce of his usual macho demeanor but failing miserably. "was I really that tight?" He asks his voice sounding meak even to his ears.

“Very” she breathed out. And slowly… she begins to insert her dickclit back in….this time much slower.

Bowen’s body tenses up once more as he feels the familiar burning stretch. He looks at the ceiling with wide, watery eyes, his lips parted in a silent 'O'. "Hea-Heather..."

“Mmmmmm” Heather says as she kisses the nape of his neck. Sucking a little. Her full length eventually sliding back in fully.

“Ready?” she whispers to his back

He whimpers softly against her neck kiss, feeling completely taken. He's never felt this exposed, this **** - and honestly, he's engrossed by it every minute. "Ready... Fuck..." His voice trails off into a moan as he adjusts to having her fully inside again. "God..."

Slowly Heather begins to move her dick in and out savoring the way Bowen’s inside contract around her ,eliciting sensation onto her with each twitch.

His back arches instinctively, pushing back against her slowly thrusting length. He lets out a low, guttural groan that he's never made during football practice or weightlifting, a sound that's entirely foreign yet incredibly satisfying. "Hea-Heather..." He pants,

“I wonder if *huff* If I could *huff* find that sweet spot men have” Heather spoke in between her slowly increasing thrusts

Bowen’s eyes roll back in his head as her hips begin to move faster, burying herself deeper with each thrust. He feels something strange building inside him, like a knot twisting tighter and tighter in his stomach. "No...please no..." He whimpers, his voice breaking. "Heather..."

But that only fuels her thrusts more as she increases in speed “Why…the fuck…not”

His body tenses up, his muscles clenching around her length as he tries to pull back, to arch his back more and more to get away from the strange, building pressure. He pants heavily, his voice strained. "Because…because..maybe it'll...it'll hurt more..."

“*haaaa* no, you're just afraid you’ll like it too much!” Heather accused as her thrusts increased to a punishing pace.

In return Bowens gritted mouth cries out loudly, his hands gripping the bed sheets tightly as he feels himself being pushed closer and closer to the edge. His body moves in sync with hers, his hips bucking back to meet each brutal thrust. "Fuck...FUCK...I...I'm gonna..."

And that when she hits it…..squarely… right on his prostrate.

And it like Bowen's entire body freezes as Heather hits that spot. His eyes snap open wide, his mouth forming a perfect 'O' as an intense, overwhelming pleasure shoots through him. He lets out a high-pitched, broken groan, his back arching impossibly as he comes undone.

At the same time, his walls clamp around Heather like a vise grip. The sensation almost painful if it wasn’t for the pleasure washing away everything.

Now it's Heather's turn for her eyes to roll back in pleasure as she proceeds to let out an inhumane and very unladylike sounds. Her hips thrusting erratically like a feral dog.

The sensation of Heather's relentless pounding, releases a waves of pleasure crashing through Bowen, intensifying his own orgasm. He gasps for breath, his body trembling with the aftershocks. "Oh... oh my god..."

As Heather's orgasms fill him he feels an overwhelming sense of completeness wash over Bowen. And it’s like the final puzzle piece he hadn’t known he’d been chasing, these packs few days finally slotted into place. Why he wanted this….needed this.

Heather proceeds to collapse on top of him. Her dickclit instantly softened and slipping out. A small trickle of lube dribble out of Bowen’s rear.

“Fuck that was….that was….” Bowen pants heavily, his body limp beneath Heather's weight. He feels the warm, sticky fluid dribbling out of him, proof of their intense encounter. He turns his head to look at Heather, his mind reeling. "Heather...was that..."

“Perfect” she finishes as she kisses him. And seeing the confirmation in her eyes he gives her a deep kiss.

A pleased silence descends upon the two as they both bask in there new-found and post coital pleasure.

______________________________________________________________________________________________________

Lol I couldn't leave you all hanging lol

Apologies for the long wait but I'm also writing other erotic stories on this site and this one has been a bit neglected lol.

If you enjoyed this story so far, consider supporting me on Patreon! There, you'll find tons of my stories, exclusive art, and behind-the-scenes content. Join me on this creative journey at Patreon!