The First Night

Literotic asexstories – The First Night by HalfwayThere25,HalfwayThere25
This is a true story about our first foray into the swinging lifestyle. Names have been changed.

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“One. Two. Three!” Four hands downed four shots of tequila as the sun dipped behind the trees, their shadows finally blurring into the freshly mowed grass as the first fireflies made themselves known. The preceding afternoon had been uniquely uncomfortable. Temperatures in the high 90’s with high humidity pushing heat index values well beyond the century mark. On any other hot afternoon, my wife Cait and I would have hid ourselves away in the safety of an air conditioned living room, but with guests imminent, we embraced the suffering to prepare for the evening ahead. We’ve known Tom and Sasha for years – long enough to accept that busy lives get in the way of a perfectly organized home. Something about tonight felt different, though. There was an excitement in the conversation and an impatience for the next round of drinks. Even Tom, a notorious teetotaler, was already on his second margarita of the night.

Sitting next to me, her arms folded on the table in front of her, Cait smiled furtively with lively green eyes as Sasha excitedly talked about the goings on at her office. Cait’s strawberry blonde hair was pulled into a loose ponytail with a few strands of wayward hair hanging free. At 26, Cait was anything but a fitness fanatic, but her petite frame seemed to be everlasting. Barely five feet tall, our height difference is a frequent topic of conversation and lighthearted jokes. The freckles on Cait’s face, arms and chest seemed to multiply over the summer from weekends spent lounging by the pool. Although her tan might seem nearly non-existent to a casual observer, the stark contrast of bikini tan lines clearly revealed otherwise. After three years of marriage and being forced to work from home full-time due to a global pandemic, Cait took little issue with spending time au natural around the house. Tonight, though, she was dressed in a simple, muted yellow sundress with a pink and fuchsia floral print.

“Another one?” Sasha asked as she stood, balanced three empty glasses, and carefully stepped across the deck toward a small work table doubling as a bar for the evening. “Easy!” Tom’s voice cautioned humorously from his seat as Sasha nearly dropped all three in her haste, giggling as she somewhat clumsily grabbed at the glasses. I could feel myself relax from the initial effects of the tequila as I watched her work. A second generation Greek immigrant, Sasha’s olive skin was slightly flushed from the alcohol and oppressive, still lingering heat. Naturally wavy, dark and usually left long, Sasha opted for a surprisingly short pixie cut at the beginning of summer. The short hair framed her heart-shape face in a very flattering way, pulling attention toward her large brown eyes and full lips. As much as I tried to pull away, my eyes were drawn to the short cutoffs hugging her hips, a black concert t-shirt tucked into the waistband. Sasha always dressed to accentuate her curves, much to the delight of her husband and, admittedly, my own. I forced myself back into reality only to find Cait and Tom silent, their eyes locked to Sasha the same as mine had been. Tom eventually broke away and we shared a brief but knowing smile. We had been close friends since college and knew well enough what the other was thinking, even if we didn’t have the time, or situation, to say it aloud. Tom rarely drank, save for special occasions. The quintessential gym rat, Tom’s five-eleven frame was lean and muscular and even though I would never admit it, I was always just a bit jealous of his tenacity and work ethic.

A full margarita and shot glass loomed for each of us as we conversed, discussing everything from the weather to the minutiae of our lives since we last had the opportunity to waste a night together. One by one the drinks disappeared, lost in conversation and laughter as the lights surrounding the deck slowly illuminated, washing the four of us in a soft glow, surrounded by darkness. Tom’s short sleeve button-down was already undone, his bare chest drawing the attention of the girls as he leaned back in his chair. “Showoff.” I muttered sarcastically, narrowing my eyes at Tom, eliciting a giggle from Sasha. “I don’t know, I think he needs to show it off a little more,” Cait commented slyly, her eyebrows raised. Tom only shrugged and stroked his short beard a little in thought. “It’s hot?” he replied, seemingly unsure of how to interpret Cait’s remark. “I definitely don’t mind,” Sasha beamed, as she reached out and tugged at Tom’s shirt. “You spend so much time in the gym, you might as well show off all of the hard work you put in.” In the distance, a flash of lightning from a thunderstorm miles away flickered across the horizon, teasing relief. I finished the last of my drink and nudged Cait playfully. “Tom’s right, though. I’m sick of the heat. Why don’t we get in the pool?” I stood and flicked on the switch for the pool light, casting a diffuse beam through the placid water of our newly-installed swimming pool at the opposite side of the deck.

Sasha nearly jumped from her seat at the suggestion, finishing her drink as she darted across the deck. Standing at the edge of the water, she kicked her sandals aside and stared over her shoulder at the three of us. “Your pool is amazing!” she called back as we staggered to meet her, Cait shaking her head and laughing at her friend. “C’mon Sash, let’s go inside and get changed. Do you have a suit in your bag or do you n-need one?” Cait slurred, gently holding Sasha by the arm, steadying both of them against the effects of the tequila. Sasha shook her head and immediately began working at the button of her denim shorts, finally popping it free after a few moments. “Oh, okay then!” Cait giggled wildly, nearly doubling over with laughter. Tom and I stared at each other for a moment. “You’re a lucky man, Tom” I teased, trying my best to hide a smile as Sasha shoved her thumbs into the waist of her shorts and pushed them to the deck. The laughter became contagious. The two twenty-somethings could only hold onto each other as Sasha pulled her t-shirt over her head and tossed it aside, revealing a tiny black thong and matching bra. She turned her back to Cait as she caught her breath, the laughter subsiding. “Help?” she asked weakly, motioning toward the clasp in the center of her back. “I guess, I guess we’re doing this!” Cait exclaimed as she undid the clasp, the bra sliding over Sasha’s arms. I had witnessed Sasha in a bikini several times, but I was still taken aback by the size of her breasts as she worked her thong over her hips and stood on the edge of the deck, unashamed and smiling. Before Tom or I could react, she was already mid-cannonball.

Cait barely raised her arms in time to shield herself from the splash. Sasha took a breath as she emerged, the light illuminating her naked body as she tread water. “This feels SO good!” she called out to the group with a broad smile, wiping the water from her face. Cait shrugged, turning toward Tom and I. I could only nod in return as she lifted the hem of her sundress over her head, pulling it free from her petite frame, no underwear to speak of, only a tiny patch of short, light hair nestled between her hips. Cait stepped toward the edge of the pool as Sasha whistled and hollered her approval. A nearly silent “wow” escaped Tom’s lips as Cait slipped into the water, reacting to the shock with a sharp gasp. Cait sighed as her body acclimated itself to the water. “You guys coming? It really does feel good!” The words barely left her lips as Sasha jumped on Cait, her weight pressing my wife’s shoulders and head beneath the water with a playful laugh. Tom was already out of his shirt and struggling with his shorts as I flipped the switch controlling the lighting. Darkness enveloped the deck to the sound of giggles and splashing.

In spite of the humidity, the night air felt good against my bare skin as I tossed my shirt over a chair. The effect was even more pronounced as I slipped out of my shorts and boxers and walked naked toward the pool, passing Tom who was kicking his boxer-briefs out of the way. Even in the dark, I could make out the form of his cock, standing perpendicular to his body. I was taken aback by his size. We had seen each other naked a few times, though I had never imagined seeing him with a hard on, standing on my deck. I could feel the heat in my own body rising as I ran and lept over Cait and Sasha, immediately relieved to be submerged, even if the water was warmer than usual. I breached the surface and took a breath only to be immediately shoved back under by Cait. The length of her body slid along my own in the water as I shoved her away. I could feel my cock stiffen as Sasha joined in on the attack, grabbing my ankle and pulling me toward her. As I reached to grab her wrist in self-defense, Tom splashed into the darkened pool somewhere behind me.

I heard Cait yelp as I dove at Sasha, wrapping my arms around her, pulling her under. Unavoidably, my cock pressed against her thigh, sending electricity through my body. We surfaced simultaneously, both laughing, trying to catch our breaths. “Someone’s excited!” she announced as she dove toward me once again. I felt my feet against the bottom of the pool and moved backwards, dodging her slightly. She surfaced again, this time with her hand wrapped around my cock, pulling me forward with a wry smile. “That’s so unfair!” I mock protested as I pulled away, splashing water as a distraction. As I moved to attack again, Sasha’s eyes widened and she held up a hand to stop me. “Wait!” she whispered, wide-eyed. I stopped and pushed my wet hair back, staring at Sasha as we bobbed in the now-turbulent water. “What’s wrong?” She cocked her head to look past me.

“Are they?” she asked softly, straining her eyes in the darkness. I turned and stared, barely able to make out the figures of Cait and Tom, huddled together on the opposite side of the pool. I could see Tom’s head and shoulders in front of Cait and I could barely make out her face. Her mouth was open, eyes shut tightly. If I focused my attention, I could hear her panting softly. “Oh my God, they’re fucking!” Sasha whispered excitedly, trying to suppress a giggle as though she had just heard the latest office gossip. I felt my stomach in my chest as a combination of panic, jealousy and arousal washed over me. “Holy shit.” I replied. My mouth hung open as I watched Cait’s head start to fall backwards, obviously enjoying herself. “That’s so fucking hot.” Sasha sighed as she snaked a hand around my waist, pulling me against her, her free hand stroking my cock gently in the water. I couldn’t help myself and leaned into her, our lips meeting for the first time. We kissed passionately as our hands explored unseen, our tongues darting into each other’s mouths. After a few minutes, Sasha broke our embrace. “Come with me?” Sasha whispered as she silently crept forward in the water, toward the opposite end of the pool.

I followed behind, my nervousness increasing as we inched closer to the mating pair in front of us. My eyes were now fully adjusted to the darkness, and I could see Tom’s movements in the water as Sasha slipped in behind him, kissing him on the shoulders and neck. Cait was pressed against the wall of the pool, her hands clasping the edge. I could see her legs wrapped around Tom’s waist as he slid into her with long, purposeful thrusts. I watched for a moment, mouth still agape. The feeling of a tug on my arm diverted my attention long enough to find Sasha against the wall next to Cait. Our eyes met for a brief moment before she turned her back to me, her hands gripping the edge of the pool. I moved toward her, my hands instinctively reaching out for her ample hips, gripping them as I pulled myself toward her. I felt Sasha shudder as my cock slipped between her thighs, grazing her clit.

Sasha cooed softly as my cock slid into her. The feeling of her warm cunt and the cool water seemed to dull the anxiety from watching my wife being fucked only inches away. I wrapped my arm around Sasha’s midsection, pulling her upright nearly into a standing position, my hips slowly thrusting into her. Cait’s breathing had become irregular and ragged as she inched closer to climax. Her soft pants had become desperate whimpers, urgent little cries for Tom to continue fucking her. “Cait, are you okay baby?” I asked breathily, my attention still mostly focused on Sasha’s ass pressing against my hips. “Y-yeah. Oh fuck. Yeah.” she replied as well as she could, her own attention elsewhere. Sasha took notice and I watched as her hand dove into the water between them. Tom began to grunt from the new sensation, softly at first but with increasing intensity. “Here.” Sasha said, looking back at me. “Give me your hand.” Somewhat, apprehensively, I let Sasha lead my hand into the water between Tom and Cait.

I slowly slid my hand beneath them, working my way along Cait’s stomach and around her hips until my curiosity overtook me. Suddenly, almost unexpectedly, I felt Tom’s cock brush against my hand as it pushed into Cait. I let my fingers run along the underside of his shaft as he buried himself in my wife. At the same time, Sasha was slowly massaging her clit in tiny circles, pushing her to the brink. “I’m gonna fucking cum!” Cait announced as her body tensed. I felt her hips press against Tom, taking nearly all of him in as she came. Her mouth fell open as the orgasm rocked her body, occasionally gasping for breath while Tom supported her weight, still trying to buck against her orgasm. I wrapped my hand around the base of his shaft, stroking his cock into Cait. Finally, Tom grunted loudly as his cock pulsed in my hand, emptying his seed into my wife. “Oh God! Tom!” Sasha shouted as she reached back for him. I felt her tighten around me as she began to lose control, her legs and hips twitching wildly. “Sasha, I’m close.” I moaned, trying to control myself. “Shh. Just cum!” she pleaded as my hips began to buck involuntarily. I pulled Sasha into me as I came inside of her, moaning with each contraction. Tom and Cait watching, drenched in their own afterglow, smiled a bit as we caught our breaths.