What to Wear to Your First Threesome

"You look like you should be hosting an insurance seminar."

A young-ish wife was chiding her man on the clothes he'd chosen for their special occasion. He was waiting impatiently with her in a hotel room booked for just one night.

"Do you want to roleplay?" she teased. "Here - I'll be the super-hot, super-horny woman who won't let you touch her, and you can be the schlub who jerks it in his hotel room."

Ouch, wifey. She felt a pang of regret as soon as the words rolled off her tongue. Had she gone too far?

No.

It was just fair. Red polo shirt, khaki pants. The look he was going for had fallen short of champion golfer making a Sunday charge and landed on a red flag to her bull. Not helping his cause any: he was sitting in the obligatory task chair that hotels provide for their more business-y guests, making him look a little too much like a worker bee in a cubicle or lonely guy in town for a symposium.

Still, what if she had hurt his feelings, scared him off? Fat chance. Long odds. No amount of withering shade could dim the giddy anticipation he was feeling. As far as he knew, what was about to go down in that room was worth almost any price of admission, and he actually liked this feisty side of her. It was kind of the whole point of this little affair. What could possibly cause him to wave the white flag of surrender?

Only one way to find out, but to keep turning the page.

"Sorry," he began in retort, "no one gave me a copy of 'What to Wear to Your 1st Threesome.'"

Cringe.

"It's my fault," she graciously offered, "I should have picked out your clothes, like I usually do. #wifefail."

Note to hubs: that's how you turn a self-own into a sick burn. Bow to your queen.

Her fit on the other hand was unassailable: little black dress hugging every curve, fuck-me platform heels in black patent leather. Underneath? I won't get into it right now, but trust me: equally on point. You'll see.

While they waited for their special guest to arrive, she was doing her darndest to be the cool chick in this scenario. Her well appointed backside was propped against the desk affixed to the wall, one elegant foot draped over the other in a casual pose that belied the turmoil making a mess of her. She was almost pulling it off, but she had a couple of tells. One calf would shift against the other when her hips squirmed restlessly from time to time; and the single finger inserted just between her strawberry lips was trembling slightly. She removed it to look at her watch.

"If they flake for much longer, I just might have to fuck you right out of those awful clothes."

Game over, 40 love, but hold that thought. There's a knock at the door.

--------

Was this little rendezvous his idea? Was it hers? When a couple's been together as long as they have, it could only be theirs. They shared everything.

It started with a moment of perfect honesty. Ask anyone: Honesty is the cornerstone of any healthy relationship.

"What's your deepest fantasy?"

Okay, but don't answer that, wife. Absolutely don't, for example, admit that you secretly hunger for something more, if that's your jam, pillow princess cum slut or size queen. It doesn't matter how many times he asks. He had asked a lot. For months, if not years, it was like a ritual or a game that played out in the runup to their affectionate sex. He would ask her between seductive, tender kisses on the nape of her neck or in pauses between deep kisses on her lips.

"I don't have any," she demurred without fail and without pause, "I want whatever you want."

She knew the rules. Be sweet. Be accommodating. Make everyone comfortable. Be a good host. Safeguard the sanctity of this bond, like your survival depends on it. That's the wife's job.

They'd met young. Highschool sweethearts, if you can believe it. Now that they were good and married - really really married, not newly married, not just a couple of crazy kids - he felt uniquely obligated to help her unlock the really filthy stuff he was pretty sure she kept bottled up. They needed to make up for lost time, head off the FOMO of fumbling around as clumsy virgins who hadn't a clue what they were all about. No judgment - we'll figure this out together. No need to be shy, no need to hold back. He only wanted whatever she wanted (well, thought he did). So supportive, so open-minded, so obsessed.

He seemed to let it drop, eventually. I mean, you can only ask the same question and get the same answer back so many hundreds of times before you get the hint, amirite? But he was undeterred. He had merely paused to change tacks, a patient tiger crouched in tall grass.

On some future night under a new moon, they coupled on the couch until his tender kisses had coaxed her out of all but a pale blue bra and matching panties (his purchase). Oh, that sight. He could stare at her, just like this, for hours; but sooner or later, he would reluctantly decide it was time to move things along, whereupon he would lead his little lingerie model from living room to bedroom. He completed her undressing beneath a wash of silver light that shone through blinds half-closed. Stripes of light slanted across the outward curve of her breasts, her hard nipple, her stomach, and the strip of hair stippling the gentle rise of her mound, his dreamy wonderland that he would wander with his fingertips from neck to waist over and over. He nestled his lips next to her ear. He kept tantalizing her skin, occasionally circling between her legs, but never dipping fully between her lips, never parting the little patch of hair to visit anything more upon her clit than the most maddening tease. He came impossibly close to touching her at the spot where her soft flesh curved inward, but all he gave her was a vanishing caress of the utterly wet edge of her innermost lips, as he breathed into her ear: "Do you want me to touch your pussy?"

She bit her lip and nodded.

"Is it throbbing?"

She nodded again. It was aching, desperate to be touched. He continued to tease until the ache grew impossibly intense, her hips lifting up off the bed to try to catch his finger and unleash the immense pressure she felt from the tip of her clit to to its furthest reaches inside her. His fingers danced away, just out of reach. The feeling inside her continued to grow. So devious. So cruel.

He moved from her side to between her legs, his hands still running over her skin. He was now naked, too, having shed his clothes in a flash, and his hard cock was poised and ready just outside her. She opened her eyes and locked her gaze on his.

"Please" she whispered.

"Please what?"

"Please touch it. It hurts."

"I'll only touch it if you tell me."

"Tell you what?"

"Tell me what it wants."

"It wants your dick." She looked down at it, at the engorged head, the hard shaft. All of it. Now. Please.

"But if it could have anything at all, what would it want most?"

She bit her lip. He was close to getting his way. He could feel it.

"Tell me. Tell me anything."

She was beginning to doubt that she would hold him at bay. The ache was beyond unbearable now, every delicate movement of his fingers over her skin and every sight of his cock another stab of exquisite torture. Her body, her mind - it was all getting ready for a more and more appealing trade: capitulation for copulation.

Consequences be damned, "It wants a dick," she blurted out, "it wants a massive dick filling it up, over and over again."

In one fluid motion, he plunged his cock between her lips swollen and slick, but still so tight that the sudden intrusion of his dick provoked a gasp. Her eyes shot open and her head rolled back in ecstatic shock that fanned out into relief. At last, give it what it needs. He fucked her until she came.

After, she rested in his arms, quiet with worry that led her to seek to reassure.

"You know I meant your dick, right?"

He chuckled. "Didn't sound like it."

She tried to pass it off. "It was just dirty talk," she said, "Literally the first thing that popped into my head. I was playing off of whatever I thought might get you to touch it." Then she added an extra phrase that sounded like it strained even her own incredulity: "I was afraid it wouldn't work."

Side eye.

"It must have popped in there for a reason. Look, don't feel bad. I asked. You answered. What you want is what you want. It doesn't threaten me. You can want more dick, as long as you still want my dick."

He'd seen himself in the mirror. No one was going to use phrases like "Greek statue" or "Adonis" around his bod. A little soft in the middle. Broad shoulders, strong arms, but no veins visibly popping anywhere. And his dick. His dick was fine, perfectly serviceable. Hard worker, eager to please, but he knew the stats. Verdict: it was not brag-to-your-girlfriends material.

He stroked her hair. "I could even be okay making it a reality."

She said nothing in response; he let it go; and the magnanimous offer lingered in limbo in her thoughts indefinitely. Outside of that moment, the fantasy was indistinct, intriguing in a vague sort of way. It goes without saying that she didn't believe his seemingly enlightened encouragement. How much jealousy and rage had she witnessed in her lifetime? Don't tell me men are the rational ones. From observation, the concept of sharing dims for the male of the species at the end of kindergarten; it is on its deathbed by the time the allure of pussy makes him lose his mind around the seventh grade. She waited weeks and months for hints of anger and fear (or worse: budding obsession) to emerge. When none were forthcoming, her curiosity popped its head out of its hiding place cautiously, during a warm font of afterglow. Safe a time as any, while the oxytocin still runs high but the testosterone and prolactin are low.

"Did you really mean it when you said you'd be okay making it a reality?"

"What a reality?"

"My fantasy."

"Oh, that. Yeah, I meant it."

So casual. Just "that." He can't be serious. Oh, yes, he can.

"Aren't you afraid I might like it more?"

"I can live my whole life in selfish fear of the worst that could happen, or I could wonder, 'What's the best?'"

"And in this case that would be...?"

"I get to see you enjoy yourself in a way I wouldn't get to otherwise. It might be amazing."

"What if it's not and we regret it afterwards? It'll be too late to take it back."

"It's always too late to take anything back. If we thought like that, we'd panic at every decision we make, even the seemingly safe ones. We'd freak out, even when nothing changes. The status quo is not the absence of a decision, but an infinite series of decisions to keep doing the same thing. We never know the alternate path, unless we take it. It's how we deal with the way we feel about it after that matters. Celebrate every experience. Regret is a waste of time."

"Won't you get jealous?"

"Maybe, but why? What do I get out of depriving you or even him? If I've already been fed, do I get fuller by slapping someone else's plate away?"

She was a plate of food, she thought, but okay, point taken. He did have a couple of conditions. The first was uncontroversial: it had to be someone they were both okay with. The second was a struggle.

"We do it together. It will be a shared experience. This fabled other dick would be an extension of me, not a substitute or replacement."

"You mean I would have to be with you both at the same time?"

He nodded.

"I don't know about that," she said, hesitantly. "That's a lot of pressure. I'm not sure I want to have to take care of two men at the same time."

She pictured it like this: one insistent dick in her face demanding a blowjob, while she was trying to concentrate on the dick that might actually make her cum - the one buried in her twat. Not her idea of fun. There was a real fear factor, too. Two aroused men in the same place at the same time...let me count the ways that can go wrong.

"No, no" he said, "We would take care of you, as a team, one taking up exactly where the other leaves off. We would get off on getting you off. It's the only way this works."

Hmm. It would require some thought, she thought, but her subconscious hopped right on board. What id doesn't like being the center of attention? The occasional abstract sexual dream she had of her man doing things to her became populated with a larger, faceless, equally attentive second, whose presence and intuitive, empathetic, and ample skill provoked a vivid intensity that shook her awake to an insistent warmth between her legs, which she would have to smother with her palm to get it to leave her alone so she could get back to sleep.

She would rub it away, imperceptibly and quietly, so as not to wake him. With the ebb of the secret orgasm came a wash of guilt. There's a word, she thought, for a woman who enjoys even one dick or a few too many or too much, much less a woman who allows herself to entertain two in concert at the same time, who lets herself imagine herself being entitled to whatever sensations two dicks could deliver that one could not ("Slut," she thought, "It would make me a slut."). The illicit rush of programmed taboo only intensified the power of the idea. She'd repeat the word to herself each time the dream left her shook from slumber. "Slut," she'd silently mouth, as her fingers rubbed her off, "I'm a dirty slut." She came that much harder with the unvoiced word on the tip of her tongue.

In her waking moments, her thoughts incrementally evolved.

"Not for me. I'm not that girl."

"You'd need just the right guy to pull it off. Not pushy at al. Someone I'm 100% comfortable around. Zero pressure."

"Hard to find, though. Not a stranger, but not someone we know..."

"Where would we even start?"

And there it was: the very practical question of someone who's decided that the vicious cycle of fascination compelled her to try.

"Okay."

"Let's not put any pressure on it," her man counseled, when she announced her agreement to his terms, "I don't want to become those people: you know, constantly trolling, all about one thing. Let's just meet people, see if someone clicks. If they never do, this little fantasy will remain just that. We'll have fun with it. If nothing else, it'll be informative. Call it a social experiment, if that's all it is. "

He would handle the recruitment; she would approve all online profiles. He would do the first round of screening to guard against creeps and weirdos; she would have final say on whether any meet-up would take place.

And so began what came to feel like a fruitless series of drinks, coffees, the occasional lunch. Some of the men were nice enough, but every one of them was obsessed, every one of them was all too eager to brag about their prowess and the size of their package. It was bland and tedious and off-putting. Her mind was left firmly closed, to say nothing of her legs; and it was beginning to leave her oddly depressed by the wasteland this little jag had led them into.

"We should stop," she said in a deeply resigned tone one day over dinner.

He was unsurprised and unfazed. "Okay," he replied, simple as that. The boundaries remained where they had always been, and that was fine...until.

They were driving in the middle of nowhere, one of those long winding ribbons of asphalt through wilderness punctuated at irregular intervals by a trailhead. Next to one was a parked car with raised hood, white ribbon flying from a corner to indicate a traveler in need. As they approached, a figure waved to them. Her man slowed the car and pulled over as the figure resolved itself into a man.

"I thought we were the only ones who came out this way. Let me check it out." Yes, brave man. Go explore.

She waited patiently in the car, watching the silent movie of their conversation.

"Hey, thanks for stopping."

"What seems to be the problem?"

"Well," he said, with a sheepish, aw-shucks grin, "I miscalculated. I don't have enough gas to get to the nearest station this way [he pointed back the way they came] or that [he pointed in the direction they were going], and I'm just hoping someone is willing to take me one way or the other, so I can buy some fuel and find my way back here. Hopefully."

"OK, give me a second to talk it over with my co-pilot."

They were more than willing to give him a lift. As he procured and filled the biggest gas can he could buy, they told him they'd take him back, too.

"Gosh, you don't have to do that. If you got places you need to be, keep going. I'll find another ride."

"We're not in a rush."

"Well, at least let me buy you lunch or something. I really do appreciate this."

The three of them sat and talked over beers. The man was spending the summer moving from place to place, camping, doing this and that.

"Life a drifter?"

"Nah, I wouldn't say that. I'm just taking a break. I'll settle down in the fall, go back to my boring 9-to-5."

At some point, the beer kicked in, and she felt the need to excuse herself. "I am going to use the ladies," she announced and got up. As she left the table, other man's eyes flitted for a second - just a fraction of a second - to that ass. Someone took note.

"Did you just check out my wife?"

"What?!" the other man asked, startled, "No! No, no, I wasn't. I mean, I didn't."

"Look, relax. It's okay."

"I'm sorry. I didn't mean any disrespect."

Wave of the hand, pursed lips, shrug of the shoulders. "None taken. I might be more offended if you hadn't. I have eyes."

The other man shifted in his chair and looked around. "Are you for real? This isn't like a scam or a hidden camera show or something?"

"No, nothing like that. I'm just a realist. I'd look, too."

"How long you been together?"

Her man held up a collection of fingers.

"Wow, and you aren't possessive. Good for you."

"You reach a point where you're comfortable, you know...and anyway, I can't afford to be jealous. She catches looks. I mean, you saw. Those jeans. I wonder sometimes if she just doesn't know how she looks in them or if she wears them to torture me."

"Either way, you're a very lucky man."

"Thank you yes. Apple bottom, so tight. God. And that shirt. She's gotta know I can see her bra right through it, right? When she bends over, I can't help but look down it. I'm like a school kid with her. It's almost embarrassing."

"I'd be in the same boat, if I were in your shoes."

This guy gets it. "Kind of nice to be able to say it to someone." Pause, and then a thought. "I hope you won't find this weird, but she and I have been talking about something lately, and I'm wondering if you would be interested in..."

"Hey, you two!"

What do you know? She was back to a suddenly quiet table full of slightly strained glances.

"What were you two boys talking about?" she inquired in a solicitous tone.

"Uh," her man stammered. Pull up! Pull up! Other man to the rescue (quick on his feet): "We were just discussing the career reality I'm putting off going back to for as long as I can afford."

"What is it you do?"

"I'm an actuary."

"Oh," she said and crinkled her nose, "I don't blame you for not rushing back."

They fell back into conversation. The question her man had been about to pose went unasked. As they talked, she contemplated the handsome stranger. Her mind wandered to a place wherein she was comparing him to the endless stream of men she'd shut the door on. "Why couldn't we have met someone like this on the apps?" she wondered. Funny. Self-effacing. Respectful. Zero creep factor at all. Has some ambition, but enjoys life. The perfect temperamental complement to her man. From certain angles, he even rather resembled him (except in one crucial dimension, she hoped), which might make it easier. He had a kind smile, strong jaw, light hair, and he was in shape - trim from a summer spent outdoors, broad shoulders...and then it struck - an unguarded twinge she hadn't let herself feel since meeting her man - the butterflies of a schoolgirl crush that her adult self recognized as the passing of instantaneous judgment. Under the right set of circumstances, she would let this man fuck her. Should she pull her man aside to share her epiphany? She deemed the odds of awkwardness too high ("Sweetheart, I've experienced a breakthrough. Ask him, 'Hey, I know we just met, but would you be interested in...'").