Under Cover of Night

Chapter One

Jill groaned loudly as Evan finally slid into her heated pussy. He had been kissing her for so long she felt like he would never take the next step and give her that cock. She liked Evan, but he was terrible at picking up hints, even if that hint was literally her screaming, "fuck me!" Evan was an okay, but oblivious guy. Muscular in a meathead kind of way. In other words, he looked good on Jill's arm when they were in public. He was dumb as a box of rocks and had a cock that barely counted as manhood. Her ex, Charles, had been six inches which was the perfect size according to Jill. Evan however, was just past four inches and near-pencil thin. He was gifted with a killer body, but had very little else to show for it. Still, at this moment his cock was better than nothing.

Even after all the nudging, implications, and outright coaching Jill had given him over their six month relationship, Evan just pounded into her like a beast. He grunted loudly while looking out into the middle distance. He never looked at her while they fucked and Jill often had to grab his mop of curly hair to pull his gaze down to her body. Today was no different, within seconds, he came.

He insisted on spraying it over her body like she was a pornstar. He would always pull out and grunt, "open wide, baby." However, his sparse cum never made it higher than her bellybutton as she laid on her back. Evan collapsed on the bed next to her and within seconds she could hear him softly snoring. Jill rolled over and ran her hands over her soft slit. She moaned at her expert touch.

She rubbed her clit furiously for several moments and was ecstatic when the needed wave of pleasure nearly crippled her as her muscles tensed throughout her body. She finally exhaled and drew the sheets in around her. She lay there in the haze of delight, just as Evan farted in his sleep. Jill groaned and eventually joined him in slumber.

Chapter Two

Jill awoke and stretched while seated at the edge of the bed. Evan had left early in the morning. He went to the gym every day around five o'clock. She was relieved to have him out of her apartment this morning. He was unemployed and would often stay at her place during the day to play Call of Duty because her internet was faster than his. Evan lived with two other guys and they both were streamers. They each had less than a hundred followers and never left their bedrooms. Evan had been moonlighting as a fitness influencer on Instagram and, to Jill's surprise, had grown a decent following, mostly guys obsessed with the gym life.

Jill stripped off her clothes and headed to the bathroom. Jill was thirty-two, a year younger than Evan and found happiness in her life as a veterinary technician. She had always loved animals and she was positively gleeful when she realized she could help them on a daily basis. She padded into the bathroom and looked herself over in the mirror. She still had dried cum on her body and mindlessly picked at the spots while she brushed her teeth.

Jill was about five foot five, had shoulder length wavy brown hair and blue sparkling eyes. Her father was Mexican and her mom was from Norway, which made many of Jill's features stand out. She had c-cup breasts peaked with small brown nipples. Her waist was narrow, mostly due to the barre and pilates sessions she thoroughly enjoyed. Her ass was round and full, which complimented her rounded hips. The defining feature of Jill's body was a long scar that ran from just below her belly button to above her sternum, due to a surgery needed when she was in high school. It had taken over a decade, but Jill had eventually learned to love it. Deep down, she knew that was the reason Evan didn't look at her as they fucked.

Jill showered and made her way to the living room. She had to spend the day tidying up, because tonight was game night! Jill loved game night. It was a chance to get all her friends together and play board games, drink like fish, and eat junk food. Tonight was her turn to host and she was looking forward to seeing her bffs. She made her way around her apartment, dusting and vacuuming. She had to spend extra time by the couch due to the mess Evan made while he played video games.

As afternoon approached, Jill began setting out the snack foods and mixing the batch cocktails. Once she was satisfied with the offerings, she retreated to her room to get dressed. She chose a baggy pair of jeans that hugged her hips and a hoodie that was short enough to expose a bit of her midriff, yet still obscuring her scar. She chose her lucky red lace thong and matching bralette. She always seemed to win the majority of games with this combination. They were slightly itchy, but she was a sucker for superstition. By the time she had the apartment ready, it was time for her guests to arrive.

Chapter Three

Karla and her husband Chuck were the first to arrive. Karla was a paralegal and Chuck worked as a mechanic. Karla had known Jill since college and they were always very close. Karla was super cute with a bubbly personality and it was at constant odds with Chuck who was very soft spoken and always difficult to hear. Karla was eight months pregnant with their first baby and both her and Chuck were already feeling the strain of parenthood.

Next to walk in was Stacy and her girlfriend Mona. They had been together forever and Jill thought they were the cutest couple. They were both blonde and pale and looked like twins. They were super fun to hang out with, but it was a bit annoying how they finished each other's sentences. Stacy met Mona at a Jennifer Lawrence look alike contest at a bar when they were in college and they were inseparable from that moment on.

Behind them came Art and Colin. Art was a longtime friend of Jill's and was always fun to be around. Art was gay and sadly had just been dumped by his boyfriend. Colin was married to Art's sister Janet who was out of town due to her job as a fashion designer, so Art convinced him to tag along. Both were tipsy when they walked in and brought a half-finished box of wine.

Last was Paula and her coworker Anders. Jill was Paula's maid of honor at her wedding and Paula never brought her husband Allen to game night. He was a grumpy sort who didn't like social interactions so Paula always brought someone different with her. Paula was a friendly, yet quiet librarian with thick rimmed glasses, long black hair, and a thin body which she always concealed in large sweaters and wide-legged palazzo pants. She was a year older than Jill, yet looked like she was well into her forties. Jill thought it was the stress of dealing with her husband.

Paula introduced Jill to Anders and they shook hands. Anders shyly complimented Jill on her apartment layout and Jill smiled at his thoughtfulness. Anders was about forty and was not much taller than her, maybe five-seven. He was on the heavier side and sported a brown beard that covered his double chin. He wore clear plastic glasses and rarely made eye contact with Jill. Jill thought he was cute in a lost puppy dog sort of way.

Jill showed her guests where to find the snacks, cocktails, wine, and beer. Soon, they were all sitting around the large coffee table in Jill's living room, chatting and drinking. The first game they played was a logic game that required everyone to figure out a murder. It was similar to Clue, but there was no board and pieces. Players had to take notes and ask questions to eliminate suspects. Jill was glad her boyfriend Evan was busy tonight as he hated any game that required thinking. Even Connect Four was over his head. Art won this game and gleefully rubbed it in everyone's face.

Mona brought a board game that focused on strategically obtaining wine regions and dominating international wine sales. It was a super interesting take on Risk that, with a little nudge from Karla, turned into a drinking game. After a few hours, the entire group was laughing and having a great time. Even Chuck was letting loose. Jill glanced over at Anders and he was sitting close to Paula in a way that felt like he was using her as a social safety blanket.

After they had their fill of acquiring wineries, Karla introduced the next game. She took a long moment to stand, her large pregnant belly forcing her to teeter a bit. Chuck helped her stabilize herself and she gleefully spoke, almost like a circus ring-leader.

"Hear ye! Hear ye!" Karla laughed as she got everyone's attention. "For our next game we will be playing 'Under Cover of Night!'"

There was a murmur among the group. "What's that?" Stacy yelled, her voice laden with curiosity..

"I'm glad you asked, my sexy friend," Karla was clearly enjoying her role as gamemaster. "'Under Cover of Night' is a localized scavenger hunt where teams must explore this building and neighborhood to retrieve ten items of increasing difficulty. It is currently nine o'clock in the evening and you have two hours to find your items. The team with the most items wins this!" Karla reached into her bra and produced a piece of paper. "This is a gift certificate for two massages at Solace Spa! This goes to the winning team!"

There was a lot of murmuring and giggling among the group as Karla sat back down, very pleased with her theatrics. Jill poured another glass of wine for herself in the kitchen and when she returned to the group, Karla had put strips of paper with each person's name on it into a bowl. Jill was a bit dismayed as Karla had dumped the chips out of the bowl and onto the table.

"Since I am pregnant, I will be going into Jill's bed, where I will lay down and look at half naked men on Instagram while you all run around the city. Please pull a name out of the bowl and see who your partner is!"

Mona went first and pulled out Paula's name. A move that delighted Paula. Her and Mona shared a quick squeeze of each other's hands. Next was Chuck and he pulled Colin's name. Both men nodded silently to each other. Next, Stacy pulled out Art's name and they playfully kissed each other on the cheeks. Jill reached in and pulled her own name, but she knew Anders would be her partner. Anders looked up at Jill and gave a sheepish smile.

Karla fanned out four slips of paper with the ten items typed on them. At the top of each slip, in bold font was the arching words 'Under Cover of Night.' Each pair looked over the slips and Jill laughed out loud when she read the items:

One Tube of Cherry Lip Balm/Gloss

One Handheld Pocket Mirror

One Box of Matches

Three Feathers

One Bottle of Scented Body Lotion

One Pair of Sunglasses or Blindfold/Sleep Mask

Four Pieces of Fruit-Flavored Gum/Mints

One Condom

Two Tampons

Two Pair of Red Underwear

Everyone in the group guffawed at the ridiculous list of items. There were mumblings around the groups as each began to assemble a gameplan. Soon, each pair grabbed their jackets and headed out the door. Jill and Chuck helped Karla to bed and quickly it was just Anders and Jill alone in the living room.

Chapter Four

Jill spoke first, "where should we start?"

Anders thought for a moment and then asked, "this is your place right... do you have any of this stuff here?"

"You are brilliant!" Jill excitedly exclaimed.

Anders blushed and gave her a timid grin. Jill immediately jumped into action. She ran into her kitchen and slid open the lowest drawer, what she called her junk drawer. In it she found the matches, an old pair of cheap sunglasses, and a small half-used Chapstick. She returned to Anders who was still standing in the living room, looking over the list. Jill giggled as she set the items on the coffee table.

She flopped on the couch to catch her breath. She looked over at Anders who now sat in the chair there rather stiffly. "How long have you known Paula?" Jill asked.

Anders answered quietly, "about a year. I work as a library technician at the main branch downtown. Paula has been filling in there over the last month. She says you two are good friends?"

Jill laughed, "oh yeah, Paula and I go way back. I was her maid of honor and she probably will be mine someday."

Anders smiled, "oh nice, do you live with your Fiancé?"

Jill laughed out loud. "No! God no! I mean, I have a boyfriend, but I don't think he's husband material."

Jill looked over at Anders. He was cute and she liked his kind eyes. His well-styled straight brown hair fell into his face, with a slight curl and Jill found herself curious about this quiet librarian. They made eye contact for a brief moment and Anders nervously broke the silence. "What's next?"

Jill took a swig of wine and bound over to the bathroom.

In her cramped bathroom she found the tampons, the mirror, and the lotion. She went to the living room and placed the three new items in the growing collection. She found her purse and dug through it. "Damn, no gum!"

Anders then spoke up, quietly, "I think I have gum in my jacket."

He went to the front door and found a pack of cherry gum in his inner coat pocket. He placed it on the table, there were exactly four pieces in the plastic bubbled container. "What's left?" he asked, a fresh smile creeping over his face. Jill noticed how his eyes glittered and felt a twinge of attraction to the stout man.

Jill thoughtfully looked over the list. "Feathers, condom, and underwear," she said matter-of-factly. Jill sat on the couch and Anders sat in the chair opposite her, lost in thought. Anders said, "we may have to go out to find the feathers, perhaps there's a bar down there with a drag show or something."

Jill gleefully laughed, "Sorry, I don't think we'll find one around here. On this block alone there are three sports bars, not exactly that type of atmosphere. I think we'd have more luck finding a bachelorette party."

Just then Jill popped up. "I know where there are feathers!" She pointed herself toward her bedroom and tiptoed to the door.

She quietly pushed open the door and saw Karla on the bed. She was napping, laying on her back. Her phone shone bright and was playing a hardcore porn video when Jill walked in. The video was quiet, but Jill could tell the female performer was screaming at the deep pounding she was receiving. There was a faint scent of sex in the air and Jill had the suspicious feeling that Karla had been masturbating. Karla snored softly as Jill approached the closet. Jill laughed to herself as she looked over at her pregnant friend before sliding the closet door open.

She got on her hands and knees and dug around at the bottom of the dark closet. After a while she found what she was looking for. Quietly, she stood and snuck out of the room carrying a pink shoebox.

Back in the living room, Anders sat quietly looking over the list and the items on the table. Jill sat on the couch and slid the lid off of the box. Inside were a few pink items. A pair of pink-fur lined handcuffs, a bopper headband with two small penises on springs, and a long pink feather boa. Jill grinned and looked at Anders, who had a confused look on his face.

"These were some accessories we had at Paula's bachelorette party. You know, just a bunch of dick-shaped things," Jill laughed as she recalled the night before Paula's wedding when she and Jill shared a drunken kiss at a dive bar. Jill plucked three feathers from the boa and placed them with the other objects.

"Fuck, I don't have any condoms here," Jill spoke disappointedly. "Wait, maybe I have one in my nightstand. Evan hates wearing them and honestly, I don't care because I've been on the pill for ages and it's just so much better." Jill tended to babble when she had a few glasses of wine and she found the company of Anders to be very relaxing and unassuming.

"Fuck, we might have to go out after all," Jill admitted as she flopped back onto the couch.

Anders sheepishly reached into his pocket and pulled out his wallet. He dug into the small leather rectangle and pulled out a shiny gold square. He laid the condom on the table and put his wallet back in his pocket. Jill laughed out loud and that seemed to relax Anders.

"Wow, that's everything but the underwear!" Jill said excitedly.

Chapter Five

Jill had just used the bathroom and poured Anders another glass of bourbon. The group had been gone for about thirty minutes and Jill and Anders still had an hour and a half before the game was over.

Anders sipped his drink, leaning back in the chair. Jill looked over his body. He was chubby and soft with thick thighs that strained against the khaki material of his slacks. He wore a blue button up shirt that was untucked and his modest belly rolled over his waistband. He had small mounds for a chest, but Jill was attracted to him in an intriguied sort of way. His beard was neatly trimmed and he looked immensely intelligent and caring. Sure, he wasn't jacked like Evan, but Anders seemed sweet. Paula always had the ability to find good people and see people for who they really are. Jill often felt she was superficial when it came to men, perhaps there was a correlation between that and her recent romantic luck. Jill shook the thoughts away as she noticed something.

"Red!" Jill shouted, nearly spilling her wine.

Anders was taken aback, nearly tipping his drink into his lap.

"You're wearing red underwear!" Jill lowered her voice remembering the slumbering pregnant woman in the bedroom. "I can see it peeking out of your pants."

Anders instantly turned red, his blushing cheeks framing his beard. He looked down and slowly pulled the waistband of his boxers up out of his pants, showing the bright red color of the thin material. Anders laughed out loud. It was the first time Jill had heard him make any noise above a polite whisper. Jill found his deep, resonant voice intoxicating.

"Quick, go to the bathroom and take them off!" Jill insisted. As Anders stood up, a thought struck her like lightning. Without thinking of Anders' presence, she pulled up her hoodie a few inches and grabbed her red thong and exposed the lace to Anders. His eyes went wide as Jill showed the stranger her tiny red panties. "Dude! We are so going to win this! Go take those off and I'll do the same."

Anders, still dazedly looking at the round, exposed hip of Jill, almost stumbled over the coffee table on the way to the bathroom. Jill heard the door click behind him followed by her phone buzzing. It was the group chat:

Paula: How's the search going?

Art: Not good, we only have like two things

Paula: We have one! At least we got the sunglasses early.

Chuck: We just sat down for a beer, taking a break. We got the gum and the tampons.

Art: Shit, we got the tampon and the lip gloss! We're going to be out all night!

Jill subtly texted, relishing in her subterfuge: We only have the mirror and the Chapstick. I think we might Uber downtown.

Paula: I bet Karla is loving that we are struggling.

Jill: She was asleep when we locked up. Hopefully she'll hear you knocking when you're done if I'm not here.

Jill put her phone down, positively gleeful at how her friends were faring with the task. She had all ten items and could relax for the rest of the night. Just then, she remembered the task at hand. In one movement, she pulled down her baggy jeans and thong, bent fully over at the waist.

Just then, she heard the bathroom door creak and Jill looked between her spread legs. She saw Anders standing in the hallway, holding a pair of red boxers, staring at Jill's tan ass and cunt. He was upside down from her view, but she found a certain thrill in holding his attention. For several moments neither of them moved. Then, slowly, Jill took one foot out of her pants and then the other. She scooped up the red lace panties and slid the jeans back over her hips. She immediately felt the wetness touch the dry denim, realizing that the garment in her hand was also slick with her own juices.

Anders fumbled with his speech, unable to catch any real words in his mouth. Jill approached him and took his hand. The bewildered man followed her to the couch where they sat side by side. Jill tossed her red lace panties onto the pile of collected items. She slowly and deliberately reached for Anders' boxers. She pulled them from his hand and set them on the table as well. To Jill's surprise there was a deep pooling of precum in the red boxers. There was so much that the stain must have been about three inches across. Jill immediately felt her heart pick up its pace.

Chapter Six

Anders seemed to notice the stain in his boxers and shifted his weight. As he did, Jill's eyes traveled up his thigh to his crotch. To her surprise, she saw a dark spot forming on the light khaki material. She bit her lip and pushed her hair back behind her ear. This was as close as she'd been to Anders all night. She inhaled deeply and smelled his combination of sophisticated cologne and subtle musk. She felt a heat in her core. She looked at the clock on the wall. Over an hour before the game's deadline.

"A... Anders," Jill began to speak, bewildered by the stuttering of her usually solid voice. "We have about an hour, do you mind if I ask you something?"

Anders turned to look her in the eyes, "of course."

Jill's mouth opened to ask Anders a question, but one glance at the stain and the slight bulge below it, fractured her mind. Instead she leaned forward and her lips crashed into his in a sloppy kiss. Jill ran her hands through his hair as his beard tantalizingly tickled her chin.

Anders responded slowly, slightly pulling back as Jill kissed him. Soon however, his hands rose to her cheeks and his tongue playfully entered her mouth. Jill moaned loudly. In this brief kiss, she felt more passion than in the last six months with Evan. She interlocked the fingers of her hands behind Anders' neck and drew him even closer. She revelled in his large, soft hands caressing her face and neck.

Without losing their lips' embrace, Jill threw a leg over Anders and straddled him on the couch. Instantly, she felt the rigid bulge in his khakis. It felt amazing against the slick heat of her denim covered pussy. She bucked her hips as she involuntarily guided herself up and down his cock. She hadn't dry humped anyone in over a decade, but this act felt intimate and made her pulse pound in every sensitive part of her body.

Anders hands moved to her sides and he softly guided her forward and backward on his lap. Jill enjoyed his subtle guidance and drove her tongue deeper into his mouth. Anders pulled free of her lips and began lavishing kisses on her neck. Her core lit up immediately as his lips sloppily kissed the soft skin under her chin. She arched her back and let more of her tan skin become exposed for his surprisingly talented lips.

Jill, feeling heated, pulled her hoodie over her head. Her mounded breasts hung free in the thin material of the bralette. Her hard, erect nipples threatened to cut the lace as she felt Anders' large hands fall on the taut skin of her flanks. Jill threw her head back, her tits pointing up and her ribs peaking out under her skin.

Anders stopped his caressing and Jill looked down. He was staring at her scar and looked up at her with inquisitive eyes. Jill swallowed hard, ready to open her mouth as an explanation. Instead, Anders raised his knees and pushed Jill's petite body up. To Jill's shock, Anders began kissing her scar from the sternum down. Of course he was open-mouth kissing and licking her stomach and chest, but his lips on her scar pushed her to the brink of orgasm.

Jill rotated her hips downward and her covered clit collided with Anders' cock in his pants. Instantly, she saw stars and her first orgasm smashed into her like an explosion. She leaned forward and unhooked the bralette. Her tits fell free and Anders took the right one almost fully into his mouth. He cupped the left one and gently played with the rigid nipple. Jill's breath was just small, quick inhales as she felt Anders worship her perky tits. Once again, she pushed her hips into Anders' lap desperate for friction on her swelling cunt.

Jill's hands fumbled with Anders' shirt buttons and finally she peeled open his shirt, exposing his rounded chest and belly. Jill pushed off the bralette and dropped down to her knees in front of Anders. She began by kissing his neck under his beard. The smell was intoxicating. She moved to his soft chest and lapped at his hairless nipples and chest. His skin was soft and supple, yet extremely masculine. After several long minutes she travelled down to his belly and kissed the soft flesh. She raised her hands to caress his thick love handles and guided her hands up to his beard. To her surprise he began licking and sucking on her fingers, a feeling that nearly bucked a second orgasm through her delicate system.

Jill could not wait any longer. She deftly unbuckled his belt and yanked down his khakis. Jill was in no way prepared for what she saw. Under Anders' stomach was a pristinely shaved, absolutely perfect cock, at least to Jill's eyes. Anders was probably about six inches long and circumcised. He had a pale, straight shaft with a thick, prominent vein running its length. He was thick, thicker than he had any right to be. She wrapped her hand around his base and was surprised by the soft skin covering the rigid steel-like flesh underneath. Her fingertip connected around his circumference and Jill excitedly stroked his cock.

She marveled as the soft skin slid over the rigidity and felt a deep need to get closer. As she stroked, she dropped her mouth to his large hanging balls. She sucked one into her mouth and groaned as the orb filled her mouth completely. She pumped her fist up and down his modest shaft. Anders slid a bit down the couch and this allowed Jill to get further under his cock. She released the testicle with a pop and devoured the second one. Anders' shaved skin glided on her tongue and he tasted of salt and precum. Jill spent many long minutes lost in the musky depths of Anders' heavy balls.

She let the thick testicle drop from her mouth and she brought herself up to her knees. She looked into Anders' eyes, the sweet man sat silently, his cock jutted from his hips and leaked from the tip. Jill leaned forward, opened her mouth as wide as she could and let the thick shaft disappear into her mouth. She gagged slightly as the tip hit the back of her mouth, a feeling she barely remembered. She closed her lips around his thickness and began sucking sloppily. With one hand she caressed Anders' stomach and chest and with the other she pumped the remaining, exposed length.

Anders groaned, a noise that was deep and seemed to crawl up from Anders' core. Spurred on by this, Jill dipped forward and felt the tip push into her throat. She heaved forward in a loud gag, splashing saliva onto the base of his shaft. Jill became aware of her reddening face and teary eyes, but she lost herself on Anders' perfectly formed cock. She messily bobbed and gagged on his length. She felt thick strands of spit slide out her mouth onto his shaved balls. Anders began moaning loudly, which quickly turned to grunts. As Jill orally worshipped his cock, she felt a soft but strong hand grip her hair, pulling her off his dick.

Jill met Anders' gaze. Her face was red, her lips swollen from her vigorous labor, and she had long strings of drool dripping from her chin. She stayed there, locking eyes with Anders as her mouth left open, gasping for air. Jill thought to herself what a sight she must be, for the last dozen minutes or so she was absolutely lost in the oral undertaking that she didn't even know she had craved.

Without saying a word, Anders leaned forward and kissed Jill deeply. Her eyes rolled back as his tongue danced with hers. There was something about the deeply intimate action of deepthroating Anders combined with the tender kiss he just bestowed on her that made her head swim. Jill closed her eyes and suddenly felt weightless.

Anders had scooped her up and exchanged places with her on the couch. Before she knew it he was on his knees in front of her and tugging off her jeans. As soon as the material cleared her ankles, Jill instinctively spread her tan thighs. Her pussy was shaved clean and had a paleness to it due to her tanlines. Her pink slit glistened as her lips were open and swollen.

Anders brought his face close to her pussy, resting his cheek on her left thigh. He brought up the fingers of his left hand and slid his thick, chubby finger between her folds. Jill moaned at the touch and shifted her weight, trying desperately to feel his fingertips enter her. However, Anders continued to tease her slit and for several long moments gazed at the softness of her cunt and caressed it lovingly. Just as she felt like she was going to lose it, Anders' tongue broadly lapped at her clit.

Her vision went white. All of the buildup, the aching, and the touches of Anders culminated in the best oral experience of Jill's life. Anders took his time with her soft, soaked pussy. He spent long minutes circling her clit with his tongue as he traced the swollen lips of her cunt. He would alternate between long licks and sharp swirling licks. She came hard the first time he sucked her clit between his lips. She bucked her hips upward but Anders' placed a big hand on her stomach and kept her still as he continued his oral barrage.

Once he finally slid a finger into her pussy, she was already limp. She had come twice already and was raggedly breathing, looking down at the adorable Anders between her legs. She swirled her hips and met his fingering in rhythm. He had impeccable technique, curling his fingers and delivering her another intense orgasm. By this time she had lost count of them. She also realized neither of them had spoken a word, they just instinctively knew what each other wanted in each long, passionate moment.

As if on cue, Anders rose up and leveled his spit-glistened cock to Jill's entrance. Anders leaned forward and kissed Jill deeply on the lips. He pulled back and rested his forehead on hers. For almost a minute they looked closely into each other's eyes and Jill inhaled and nodded. With her consent, Anders pushed forward.

All of the air was pushed from Jill's lungs as she felt the full length of Anders' slide into her. God, he fit her perfectly, she thought. He let the thickness fill her completely for a moment, then began moving his hips. He was slow and deep with his gyrations, and that pushed Jill to the edge of another orgasm. Anders leaned back. Jill looked over his thick body and saw a paradigm of reserved masculinity. His fingers found her swollen clit and with two pumps and a swirl of his hand, she came... hard.

Her back arched off the couch and she felt herself shiver and shake wildly. Anders calmed her by cupping his hand behind her neck and he sped up his pumping. Soon, he was drilling into Jill and she felt the full power of his body weight drive into her. She moaned loudly, and that eventually turned to screams. At this point she was holding on for dear life as Anders pounded into her cunt.

Jill sat forward after a few minutes of deep, fast thrusting and pushed Anders away. She motioned for him to sit on the couch and he complied. He sat down and his cock protruded obscenely from under his belly, slick with her juices. She faced him and lowered herself down, her eyes turning white as they rolled back, her eyelids fluttering. She made it her mission in this position to ride Anders to completion.

She did just that. Her tight leg muscles, sculpted at the gym, allowed her to quickly rise and fall on his full length. With each drop she felt him tease her cervix. She gripped him tightly and bounced wildly. Anders' hands found her rounded ass and she reveled in his touch. She looked down to see her tits swaying and she cupped them together, pinching her stiff nipples. For several long minutes, Jill rode Anders' perfect cock. As she was approaching another heavy orgasm, she felt Anders dig his fingernails into her hips.

She relinquished control and Anders guided her body up one full length and dropped her back down. As he did so, his hips drove up and met her with a loud wet slapping sounding. Jill then felt the unmistakable feeling of hot cum filling her. Her eyes bulged as rope after rope of hot seed filled her. Waves of creamy fluid filled her and she came one last time as she felt the final twitch of Anders dick as he emptied everything he had into her.

She collapsed forward. Her lips collided violently with his. They sloppily kissed, their hands wildly roving over each other in a desperate plea to find some stability in the moment. Both of their breathing was rapid and shallow. Jill did not want to, but eventually she stood up off of Anders' now flaccid cock and instinctively scooped the fluid from her pussy. She licked at the moisture on her fingers and sat on the coffee table opposite of Anders.

She looked him over. His chest and belly were bright red and his beautiful cock leaked onto the rug. He equally looked her over, taking in her tight, muscular body and long scar. A few minutes went by and Jill looked at the clock. It was ten minutes to eleven!

"Oh my God! They'll be here soon!" Jill exclaimed.

Anders looked at the clock and quickly began dressing. Jill did the same as they tried to make themselves presentable. As Jill pulled her hoodie over her head and Anders buttoned his shirt, they kissed again, a deep and moan-filled kiss that punctuated the passionate encounter they had just shared. "You are amazing," Anders said in a deep raspy voice.

Jill smiled back and nibbled at Anders' lower lip. "Amazing doesn't cover what you are."

With that, Jill ran to the bathroom to collect herself and Anders tidied the living room. He even lit a candle with the matches to try and cover up the obvious odor of sweat and musk.

Chapter Seven

One by one, each group entered the apartment. Jill sat on the couch and Anders sat on a chair on the other side of the coffee table. Chuck went into the bedroom and retrieved his slumbering wife so she could judge her game. Karla took her seat on the couch and smiled.

"Ok, my loyal subjects, what have you brought me?" She said, still enjoying her power.

Mona and Paula laid out their findings. "We got the sunglasses, mints, lip gloss, and tampons!" Mona was very excited by their haul, yet Paula looked on disappointedly.

Chuck and Colin laughed as they set their pack of gum on the table. "We had the tampons, but we lost them on the way over." They clearly had a few beers at the bar and the game definitely took a back seat. Karla laughed at this, happy her husband had fun with someone other than herself.

Stacy and Art were next. Art extravagantly drew each item from his shoulder bag. "Behold! Lip gloss, a mirror, matches, lotion, sunglasses, gum, a condom, tampons and drumroll please!" Stacy pounded the table..."Three feathers!" Art exclaimed.

Karla clucked with joy. "Everything but the red undies! That is going to be hard to beat!"

Jill leaned forward and pulled the shoebox from under the table. She looked over at Anders and winked. One by one she put nine items on the table. With each one, the group murmured and giggled. She paused for a moment, building tension. Then, she reached into the box and produced the two pairs of his and her red underwear.

Immediately the room burst into cheers. They all laughed and clapped their hands at the sight. Art looked a bit downtrodden but still smiled at the success of Jill and Anders' team. Karla handed Jill the certificate for the spa massage and congratulated them.

"Good work you two! It looks like a little bit of luck was with you both tonight," Karla spoke loudly, punctuated by a yawn. "I think it's time to go, Chuck."

Chuck helped her up and everyone donned their jackets and one by one, left. Art and Colin left first, taking their wine box with them. Then, Mona and Stacy walked out, making sure to grab the spare tampons on the table. Paula walked out first and Anders followed her, looking back at Jill and smiling. Jill felt her heart race as they made eye contact. Soon he slipped out of the apartment, following Paula.

Last to leave was Chuck and Karla. Chuck opened the door for his wife and Karla leaned in to hug Jill. As she did so, Karla whispered into Jill's ear, "don't let that one get away. He fucked you like you deserve to be fucked." She pulled back and winked, knowingly. Her eyes darted to the bedroom door and Karla winked again. Chuck drunkenly waived at Jill with his phone pulled up to the Uber app. Jill closed the door behind them and went to the living room.

She flopped onto the couch, her pussy still sore and wet from her spontaneous encounter with Anders. She leaned forward and grabbed Anders' boxers that lay on the table. She absent-mindedly stretched the material as she stared down at them. She remembered what took place on this very couch, finding a thrill knowing that Karla had seen some if not all of it from the crack in the bedroom door. Suddenly, her phone buzzed.

It was a text from Paula. It said: I'll invite Anders to the next game night. Until then, here is his number. USE IT!

Jill quickly saved his number in her phone, noticing her heart pounding in her chest. Her phone vibrated again and she looked at the message, it was from Evan.

"U up?"

She scoffed and turned off her screen. She locked the front door and killed the lights in the apartment, then headed to her bedroom. She stripped off her clothes and collapsed on the bed. In the dark she could feel the phantom waves of Anders' movements. She drifted to sleep with a smile on her face.