“I can’t.” Cassie almost sobbed the words.
“You can. It’s what you said you wanted.”
Cassie twisted against their restraining hands. Trying to get away, or get closer? Even she wasn’t sure. “No, just let me come, please.”
It was her own fault. Cuddled between them on the bed, relaxing against a mound of pillows and sipping cold bottled water, they talked about sexual aspirations (what Sean called their sexual bucket lists).
She confessed one of her deepest desires.
Mike choked on a sip of water. She didn’t have to check Sean’s reaction. His dick thwacked against her thigh, startling an uncharacteristic giggle from Cassie.
A long look passed between the two men. Sean tipped her chin. “Challenge accepted.” Then he made a comical face. “As soon as you teach us how.”
She took a moment to gather her thoughts, and unconsciously slipped into lecture mode.
“The muscles and nerves in the anus, in the rectum, are stimulated until orgasm is achieved. Clitoral or vaginal stimulation can help. I’ve gotten close before, but then I’ll have a regular orgasm and the moment is lost. The mental component is as critical as the physical -.”
She broke off, realizing at last how clinical she sounded. Instead of glazed eyes and vacant expressions however, two cocks now twitched in interest.
Phenomenal sexual chemistry and a willingness to learn. It almost hurt to know they only had a few hours left together.
No matter. She would enjoy what time they had.
“Let’s skip the rest of the PowerPoint. Empirical research works better.” She rolled onto her front and tucked her knees underneath, giving a come-hither look over her shoulder. “I’m game if you are.”
Two hours later, sweat-damp hair stuck to her forehead. The pit of her stomach ached from unfulfilled arousal. They had stimulated her, filled her, played with her. Brought her to the edge over and over, following her instructions exactly. Ignoring her cries, her pleas for relief.
The room’s cool air had tangible weight against her swollen clit and nipples. And her ass, oh, fuck, don’t even go there. Sitting on the plane would be…interesting.
But she was close, so close.
She lay on her back, bottom elevated by a pillow, legs widespread, feet planted. Normally she’d have felt like a specimen under a microscope, distinctly unsexy, but not with Mike’s reaction. He knelt next to her shoulder, eyes dreamily intent on the thick shaft shuttling in and out of her relaxed ass. An occasional throaty moan and steadily leaking dick showed how the sight affected him.
Sean pressed a gentle kiss against a sore nipple. She whimpered “no,” raw nerve endings vacillating between pleasure and pain.
“Shh,” he murmured. Tongue tip barely wetting her flesh, his breath alternately heated and cooled. The complex sensory input tightened her rectum around his thick shaft.
“That’s it, milk me,” Sean leaned up on his knees and settled a warm palm on her sex, pressing into her mound, thumb gliding over swollen lips. “Such a creamy cunt. You ready to come for me?”
The words, the way he filled her and kept filling her, made everything clench and swell. Even her lips felt swollen when she mumbled “Yes, please let me come.”
“Let’s try another position.”
“No, I need to come. Please. Forget the anal orgasm.”
She realized she was crying when Mike wiped away a tear, tender and concerned.
“Sean, maybe -.”
“No. She’s sucking at my dick. It’s gonna happen. Just need a little something more.” He withdrew slowly, gently, and lifted her to slide a second pillow under her hips. Then he turned her on her side. “Lean forward, more, that’s it. Good girl.”
The position put her pillow in easy reach and she clutched at it, turning her heated cheek into its cool softness.
Sean noticed, of course. “Bite the pillow if you need to.”
She moaned and considered doing exactly that when he popped open a cap. She waited to feel slickness coating her anus.
Long seconds passed, and nothing happened. Finally, Sean breathed “Christ, that’s so fucking hot. Mike, look.”
More silence. Cassie stirred, turned her head to see what they were doing. Sean stilled her.
“It’s the most erotic thing I’ve ever seen, baby. Your ass, it’s -.” He cupped her cheeks and spread them apart. Cool air touched swollen, sensitive flesh. Fingertips slowly circled the relaxed pucker. “Swollen and pulsing, baby, like it needs to be spread open and filled.”
Cassie shivered and bit the pillow, heat puddling in her belly at the evocative word picture.
As often as he’d been insider her ass tonight, it should have been easy. But at the first firm pressure, she protested. “Oh, slow, slow, please.”
“Hush, Cassie girl, I know what you need.” The words were soft, the tone tender, but he didn’t let up. Nature allowed his flesh to compress and hers to expand, and the thick head popped inside. A flood of lust immediately urged her hips backward.
He held her still. “Uh uh. Slow and steady and deep.”
She lost track of everything but the friction and sense of fullness. Mike got her attention, though, delicately tugging at her soft, damp pubic hair. Teasing and tickling, feeding into the deep, welling pleasure in her ass.
When Mike wedged a hand between her thighs to get more room, she tipped forward, the mound of pillows an ungainly fulcrum. He steadied her even as he pressed two fingers inside, then three, twisting and turning, touching every surface.
“Such a sweet cunt. You’re going to come all over Sean’s cock, aren’t you?” His thumb pressed upward, avoiding direct clitoral contact, massaging the bundle of nerves from just below.
Sean sped up, changed to half strokes, grinding the thick head against Mike’s knuckles. The almost brutal fucking tripped Cassie’s libido into overdrive. She screamed into the pillow, sphincter fluttering wildly, lost.
“More, more,” she begged, “More, in my ass.”
The sliding, aching stretch stimulated every nerve at the taut entrance. The thickness, the friction in her channel, in both her channels, grew into something of unmanageable proportions. She breathed deep, afraid it would slip away again, as it had before.
Sean held the pace, held it while murmuring encouragement in her ear, held it while thrusting more solidly still against the front of her passage.
“So good, Cassie,” he crooned, “You’re doing so good.”
It rolled up from her depths. A wave of such intensity it might have scared her, if she hadn’t been so exhausted.
“Yes, oh God, yes, right there. Right ther -,” her voice fractured on the rush of a powerful climax, centered inside her rectum but seeming to expand beyond her body.
Darkness sparkled at the edges of her vision. The wave receded.
Slowly, she became aware again. The men stroked her hips, her arms, held her close.
“You’ll be sore tomorrow,” Sean said.
She hissed when the warm washcloth touched her swollen sex.
“Yeah. And the day after, an’ the day af’er,” she slurred.
Mike pressed a kiss against her forehead. “We’ll let ourselves out.” Low voices. Covers settling over. Luscious warmth. Nothing more.
Cassie stumbled out of bed when her alarm blared, staggered and groaned at the pull of sore muscles even as memories triggered a smile.
“Shower. Coffee.” She mumbled the morning mantra, heading into the bathroom.
A note had been propped against the coffee maker.
We’re an hour’s flight away. Call us.
Let’s cross more things off our bucket lists.
Your students are lucky to have such a good teacher.
A lot of information is posted online about male anal orgasms. Not so much about female anal orgasm, but you may be interested in this down-to-earth, interesting article in Cosmo (of all places).
Good Teacher 4 © 2016 by Devi Ansevi
This story was written for Wicked Wednesday #207: Aspire. Click the rainbow circle for more delicious wickedness.
Feature image courtesy of Stuart Miles at FreeDigitalPhotos.net.