Double Penetration and More

"Cheers!"

Michael led the second toast of the night, clinking glasses with James and herself. Fine wine warmed her from the inside out, lightened her body like a feather. Not too much, the perfect amount of tipsy. It empowered her eyes to wander more than usual.

Kitchen light bounced off James' high cheekbones. Michael's long fingers wrapped around his wine glass. The meat being served was not the same meat she kept thinking about.

"The two of you make a gorgeous couple. The rest of the team had a bet going, of how long it would take."

Michael grinned, mischief simmering beneath it. "I won, by the way"

"Sheesh," James ran a hand over his reddening face. "How much?"

"Enough for this well aged vintage." He swirled the wine in his glass.

It's true, getting together with James took time. Will they, or won't they? It played out obviously enough for the rest of Team Michael to bet on it. Not so obvious however, was the reason it took so long.

A phone's ring interrupted the conversation. Michael glanced away from her, and stood from the table.

"Sorry, I should take that. Excuse me for a moment."

Once she was confident Michael was out of earshot, she hid part of her face behind a protective hand.

"Oh my God, that's embarrassing."

James radiated a warmth, a soft constant, that always sent her heart racing. This time was no different, not with how he took that protective hand in his own.

"Don't hide your pretty face from me."

"Ugh," she whined.

Her boyfriend turned to her, putting his free hand on her thigh and giving it a soft squeeze. The simple contact shot warmth straight up her leg, to the space between her thighs.

"Don't do that!"

Dark eyes flicker up and down her body.

"One glass of wine made you horny?"

"It's not only that. It just doesn't help, y'know? Being alone with both of you-" she trailed off.

James flashed a smile. "Mike does look really good tonight."

"Right?? He's so hot, it's not fair."

A sigh escaped her lips, at the same time she came to a realization.

"Were you scoping him out too?"

The break of eye contact and the way his smile widened gave him away. This was what held up the relationship in the first place, confusion over a shared attraction to someone who was neither of them.

Instead of squeezing her thigh again, James settled for stroking it with his thumb.

"I was wondering how many dates he takes back here, to his house. He definitely knows how to entertain guests."

"If he takes dates back home, then-" she bit her lip, "I've heard enough rumors. He definitely knows how to fuck."

The man's reputation precedes him in multiple senses, enough that she'd heard of his charm before meeting him. James laughed, a quiet snicker.

"Do you want us to take lessons?"

The idea brought heat to her face and she rolled her eyes, if only to avoid the gravitating eye contact.

"Maybe. Like that would ever happen."

"I'm flattered, truly."

Both practically jumped out of their skin, startled by Michael's sudden reappearance. He leaned against the kitchen door frame, arms crossed and head tilted. The smile on his face was catlike, equal parts charm and ego.

If she could magically disappear, she would. While she managed an embarrassed squeak, James found his words.

"How much did you hear?"

His pink tongue darted out, swiping over his lips.

"Enough."

She looked to the floor, silently panicking as Michael's shoes came into her view. He pulled out the chair next to hers.

"I've had my fair share of experiences, if that's what you're wondering."

He sat, and she was torn about what to do. Does she go for it, how does James feel? Was Mike even interested, or was he just reveling in the spotlight?

Thankfully, James spoke. "I thought so, since you're older y'know? More time for picking up babes."

"Babes, men, it doesn't really matter. Whoever peaks my interest."

He huffed a laugh. "And I'm not that much older than you. I could show you a thing or two."

Before she could digest the offer, he reached out and lifted her chin with one pointer finger. Michael wasn't going to let her hide from the conversation.

"Do you want that?"

One shared glance of excited disbelief with her boyfriend was all it took. She looked back at Michael, swallowed by an intoxicating magnetism that's distinctly him.

"We do."

He hummed.

"Good. Let's start with the basics. Can I kiss you?"

"Please."

Long fingers tucked a lock of hair behind her ear. Slowly, sweetly, Michael leaned forward to capture her lips. It wasn't needy or desperate, just a steady burn. He cupped one cheek, one kiss turning to two and then three.

"Damn," James whispered.

Despite the multitude of kisses she'd had in her life, none were quite like this. Sweet, tender, with a titillating promise of filth hidden in the way he lingered. No tongue, he didn't need it to reduce her to putty. When he pulled away he took her ability to speak, supporting her with the warmth of his smile.

This man definitely knows how to fuck.

"Is there anything you explicitly don't want, anything that makes you uncomfortable?" He addressed both.

"No bathroom stuff in the bedroom." James crossed his arms.

"And only do something up to three times or more than five."

Michael laughed after a short pause, borderline dorky enough that it startled her.

"Reasonable, alright. And you?"

"I'm not really sure. I just wanna feel good, y'know?"

"Oh, that's a given."

His hand left her face to trail down her neck.

"Let's go up to the bedroom."

Never in her wildest dreams had she expected this, and following him upstairs with her boyfriend in tow invoked weightlessness. Breathless, walking on air with her heartbeat thundering between her thighs.

The details of his bedroom flew under her radar, too fixated on the heated bodies closing in on her. James' hands squeezed her waist from behind, plush lips trailing along her neck. Another pair of hands skimmed along her front, teasing but not quite taking.

Michael hummed as he rested a fingertip at the neckline of her dress.

"You can't tell me you're a novice at this, James."

"I'll give myself a little more credit than that," his voice dropped lower, "but it never hurts to learn a thing or two."

Michael's fingertip dragged down the center-line of her body, leaving a zipper in its wake. He split her outfit in half, making it easy for James to peel the pieces away and drop them to the floor.

"So pretty," he mused, "get on the bed for me."

A statement, not a question. Her pussy throbbed.

"Okay."

His sheets were a crisp white, high thread count, buttery soft on her skin. From her throne in the center she watched James' cap tumble to the floor.

One of Michael's hands combed through the thick curls that hid beneath, the other curled around his belt. He pulled, much more forceful than he'd been with her, until their groins pushed together.

"Mike-" James hissed out.

"Listen. Show me how you touch her, how you make her feel good. I'll step in when I need to."

"Gonna grade my performance, professor?"

In a subtle motion, they grinded against each other.

"A little. Just a quiz, not a test. Go."

Reluctant to part, but eager to begin. James pulled his sweater over his head and wasted no time climbing onto the mattress.

"Please," she sighed, "I need someone to touch me before I start losing my mind."

The mattress dipped from Michael settling next to her, jacket gone but pants still on.

"We will. Be a good, patient girl for me. Can you do that?"

She bit her lip.

"I can try. Oh, fuck!"

James laid himself between her thighs, surprising her with his tongue swiping over her clit. True to Michael's request, he touched her in the way he always did.

Hands pulled her legs open, enthusiastically tasting her. Everything with James was intense, passionate. She knew his feelings for her by the way he consumed her.

Once the initial relaxation and rush faded, she looked up at Michael next to her. He was watching, somewhere between horny and amused. His pants were tented with the strain of his cock against them.

"Jay, watch."

He pulled away as instructed.

"Our bodies are more sensitive than we think."

He rested the fingertips of one hand above her navel, tracing up and down.

"Take your time."

Truly, he meant it. James watched Michael's hand skim along her curves, over her tits. He leaned down, silky hair tickling her chest as he lapped at a nipple. As natural as breathing she pushed into the contact, pouting a little when he insisted on being gentle.

The touch slipped beneath her belly button, over to one side. He gripped the thigh closest to him, pulling a soft moan from her. Licking, soft nibbling, and sucking at her nipple. It wasn't much, but it set her body on fire.

"Touch me."

"I am touching you."

Michael wore a grin on his face. He knew what she really wanted to ask for, and he wasn't letting her get away with being vague.

"I meant my pussy, please touch my pussy!"

"Place your palm on her pussy, and lay your fingers flat over it. Only that."

James listened, the expanse of his big hand somewhat cupping her sex. The contact was minor, but knowing it was close made her desperate. In an attempt for friction she tried to grind, but he moved his hand with hers instead.

The softness of her clenched down around nothing, like her body was trying to get satisfaction on its own. James sighed.

"Shit, babe. You're so turned on right now."

Michael kissed downwards, until he had to move. James made room, and Michael kissed her inner ankle, working closer to her center. Every move felt deliberate, and despite it being her leg it made her ache for him. On her inner thigh, he left behind a hickey before addressing James again.

"Stick out your tongue."

He let his tongue poke out.

"Before, you mostly used the tip to lick her clit. Change it up. Let me demonstrate."

Rather than going down on her, he used the end of James' tongue to get the point across. For him, it put the feeling into context. For her, it fulfilled no less than three of her masturbatory fantasies.

James' throaty groan made her clench again. Michael kissed, and gently sucked the tip of James' tongue. He stroked it with his own, using different movements for different effects.

Her boyfriend was already flushed, but she'd never seen him quite like this. Cheeks unevenly splotched, chest heaving from losing his breath. Michael pulled back.

"If your tongue gets tired, take a break. Touch her like this."

He lifted James' chin and swiped the pad of his thumb over the tip of his tongue. Back and forth, until James couldn't take it. Smooth and quick, he pulled Michael's thumb into his mouth, closed his soft lips around it and sucked.

Michael got closer, lured in. He glanced at James' eyes as if he'd woken up.

"Down boy, wait your turn."

It stunned both, letting Michael's thumb free. James' hand left her so the other could take over. His fingers gently parted her lower lips. He rubbed out her ache with the slip of his tongue over her clit.

"God, yes!"

Eyes rolling back, she dropped her head back into the pillows. Despite squeezing her eyes shut, she knew they were watching her from the sheer gravity she felt.

A fast learner, James traced shapes along her inner thigh and peppered kisses where he could reach. With her boyfriend and crush between her open legs she wondered if this could possibly be better.

Like he had with James' tongue, he switched it up when needed, each move taking her closer to the edge.

"Feels so amazing, Michael."

He used his fingers in tight circles around her bundle of nerves.

The slick, supple muscle of his tongue brushed against her again. The sob of her relief echoed off his bedroom walls. He lavished attention up, down, and around her clit; kissed it as he would her mouth. Somewhere in the dizzying upward spiral of pleasure she lost herself, lost sense of time, the only sense she had left was bliss.

"I'm so close, so close, Mike!"

His pace intensified, sending her over the edge. The unbearable tension between her thighs peaked, sending shivers up her spine. Both of them held her squirming body still, or as still as possible while Michael milked every last ounce of pleasure from her.

When she came down there was no need to push him away, he intrinsically knew when to ease up.

A wet sound reached her ears. Had they kissed? When she picked her blissed out head up they were already parted. Michael was in the process of pulling off his bottoms.

"Take your cock out, Jay."

James raised his brows.

"Yes sir. "

The phrase sounded like his usual brand of banter, but it earned a sharp look. Michael grinned, peeling away the last of his clothing. His cock sprung free, a delicious length with a slight curve; not as girthy as her boyfriend but just as mouth-watering. Both couldn't help but stare.

"I thought you said yes sir?"

"Fuck, I did. My bad."

He'd been struck still, but with the reminder James quickly pulled his bottoms off and threw them aside without looking.

Michael called her to get her attention. He grabbed a pillow and lifted her hips effortlessly, stuffing the pillow beneath. Plush lower lip caught between her teeth, her eyes gazed up at him from beneath long lashes. Her thighs opened wider for him. He moaned, soft and low in his throat before even touching her.

He settled between her legs, laying his bare length between her lips. Rocking his hips to grind against her, he looked to James resting by her side with his cock in hand.

"Now, pay attention. This is how you fuck your girl."

His length caught on her already soaked entrance, blunt cockhead nudging into her. Smooth and slow, he eased in until his nuts were against her ass. James watched her mouth drop open in a silent scream, at this point his dick might actually pop.

Michael fucked her in a way that shut her mind off completely. Not too hard, not too slow, angling his hips. The tip of his dick pushed and dragged against her sensitive front wall.

"There?" He asked.

"Yes, yes, right there!"

A strangled moan pushed its way up from her chest, eyes rolling back.

Michael gripped her hips and went harder, pounding at her sweet spot like a man on a mission. Her hands scrambled for anything to ground her, one landing on Michael's wrist and the other on James' shoulder. The pressure of her nails left behind scratches, not that either would dream of stopping her.

It didn't took long for his name to spill from her lips in a frantic chant. The wet slap of skin on skin and the warmth of two lovers intensified the feeling. She came again, this time with a wet gush that startled her. Michael hissed, half praise and half getting lost himself.

"Yes, that's it, so good for me."

Michael waited for her full body tremble to die down, and without cumming he slipped his dick out of her.

James couldn't hold back, stroking his cock with his fist.

"I can't take much more-"

Pretty eyes glanced at her.

"Don't hold back."

She murmured in a lazy, fucked out voice.

Maybe it was what they needed to hear, because just like that they sprung to action; firm muscled bodies colliding. James' hands wandered, fleeting and too excited to stay in one place very long. He'd waited forever to get his hands on Michael, now he wanted to feel everything.

Michael held James close by the back of the neck, while stroking his eager cock. Between fierce kisses of lips and teeth and tongue, he spoke.

"Don't cum yet."

Frustration boiled over, James broke with a whine.

"When am I supposed to? I did my homework. You're literally jerking me off right now. Shit-"

The hand not stroking James' dick slipped downward. Michael nudged a knuckle up beneath his balls. Heavy lashes fanned over the man's cheekbones with how his lids fell almost shut, mouth dropping open.

"Fuck kind of magic trick is that, teach?"

"Massaging your prostate from the outside. But you probably already do that with your fingers inside, don't you?"

"Uhh."

James went to deny it, and she watched intently. She hasn't learned much about how he pleases himself when he was alone. Michael playfully licked his chin.

"Liar."

"Not fair."

As hot as it was to watch them go at each other, being a spectator wasn't nearly as fun as participation. She crawled over to them and held Michael's stiff cock in her hand, leaning in to swirl her tongue around his tip.

The surprise earned a sigh. She bobbed her head on him, tasting herself on her tongue.

"Trying to get extra credit, baby?"

Looking up, she found herself as the object of their attention once again. She released his dick with a wet pop.

"I need to be a straight A student!"

"Mm, put your boyfriend's cock in your mouth and I'll give extra points."

James moaned the moment Michael let him go and she took him in. His cock was fatter, harder to get her mouth around. Still, she hollowed her cheeks around him.

"This-" kiss, "will be-" kiss, "the last test."

Hands newly freed, Michael let them explore the well muscled expanse of James' pecs.

"We'll both fuck your girl."

He glanced down at her.

"Our girl. Do it like I showed you and we'll see if you pass."

Her pulse jumped into her throat, constricting on James' cock.

"Mmf yes. What's my reward if I pass?"

"If you pass I'll bend you over my mattress, another time. Maybe later tonight."

"I'm ready."

James pulled away from both of them in a rush, so quick it made her laugh. Michael shook his head, pushing him onto his back.

"And you," Michael tucked a wayward lock of hair behind her ear, "get on top. Reverse cowgirl style."

He was turning out to be the filthiest gentleman she knew. He helped her into place, straddling James with her back to him. Her fucked-out pussy throbbed at the feeling of having his firm, warm body between her thighs.

He gently pushed her to lay back, James' arms automatically wrapping around her body from behind to touch and feel in the way he loves to.

James' cock slipped against her slick sex, desperate to fill her up. Michael guided his aching tip, grinning when James sunk himself in her centimeter by centimeter. His hips bucked in quick, short bursts, each pulling a moan from her. Michael swatted at his inner thigh.

"Still, just one more second."

He settled between her thighs again, the tip of him pushing against where James' already deep inside. It struck her that he didn't mean for both of her holes to be filled, instead he wanted to fill one to the brim. Stormy eyes settled on hers, giving her the space to tap out. Cold thrill washed over her skin.

"Please." She whispered.

"Such a good girl."

He pushed further, alongside James' cock. He read her body language with near clairvoyance, easing up when pain overtook pleasure, and pushing in when she was ready.

It escalated too quickly for her to realize once she was completely, blissfully, filled. Michael and James began moving, countering each other, one sliding in while the other slid out.

"Nngh, tight fucking fit babe." James grunted.

Body still adjusting, her pussy would force out one or the other. Michael persisted, guiding them both back inside each time.

Unlike other kinds of sex where she could roll her hips, ride, or counter James' movements, she was rendered helpless. Control was taken out of her hands completely, the only option was to be held in place and ravaged.

Overwhelmed, her pussy drooled on their cocks. The insane stretch knocked the breath out of her. Lips kissed against her neck and chest, hands roamed her body. They traded off between grabbing what they wanted and holding her in place.

"Mike-," James called out, "am I doing well?"

Her boyfriend could be a golden retriever, when he felt like it.