Learning the Family Business Ch. 05

"It's a special day as we celebrate Tamara's tenth year with the firm!" the invite read. Mike scanned through the email as he strolled to his car that Saturday morning. He had read through the cryptically worded message dozens of times over the past couple weeks but couldn't completely understand what the line "...bring an open mind and a full sack..." was hinting at.

"You'll have a special job for me," his step-mother had explained earlier in the week. "Just show up with that can-do attitude and everything will fall into place, you'll see," was all she would cryptically explain, though.

Almost two months had passed since the night of the auction and things had really opened up for Mike since then. He had assisted Hillary, his parents, and Stacy in closing several deals over the summer. He and Hillary didn't really have to sneak around the house anymore, now that their parents knew they were fooling around, but they still did just to keep up the excitement. To top it all off, the family now had a clothing optional policy at their indoor pool, so Mike occasionally got to see his step-mom's solid gold tits just by getting downstairs in time for a morning swim.

Mike had no idea what was going on for this anniversary party, though. It was hard to believe it was fifteen years since his own mother passed away and another eight since Tamara married his father. He had to run errands that morning to make sure all of his clients were in good shape before he returned to school for the fall semester. By the time he returned home, several luxury cars were parked to the side of their curved driveway and a limo was dropping off a couple in what looked like expensive beach cover-ups at their front door. That could only mean something was going down in the family pool. Mike hurried through the empty kitchen, sensing the excitement in the air. Caterers were scurrying through the kitchen in black tuxedos and small black masks.

Upstairs, things were calm other than the occasional laughs coming from Stacy's room. She and Hillary were certainly up to something in there but Mike had no idea what was going on. He showered and quickly changed into a t-shirt and a tight pair of swim trunks.

When Mike reached the pool area, the music was bumping and the party was already swinging. In a deck chair on the other side of the pool, Maria from the reception desk was sitting naked in the lap of Ted, the firm's accounting department director. Her round tan tits were falling into his hairy toned chest. Up against the edge of his side of the pool, Mike watched Dana, one of the senior partners, teasing the hard cocks of two men whose backs were to Mike. Her tea drop breasts sagged just a little but he enjoyed watching at the naked middle aged woman enjoy her work.

Mike dropped his towel to a deck chair and continued to explore the space. He turned a corner and entered the theater room just off the pool area. Inside the room sat several of the firm's real agents on the leather theater benches with their cocks in their hands, jerking themselves off while they watched something projected on the screen in front of them. Mike walked down the aisle between the men and their tall hard dicks and turned back to look at the screen.

In front of him was a video playing of his father and step-mother fucking. They looked to be several years younger in this video. Tamara was leaner and her breasts weren't as full and his father was several pounds lighter, as well, with fuller hair. Someone else was filming his father's meaty cock pumping in-and-out of Tamara's tight opening. Her breasts bounced as he thrust into her on a bed that Mike recognized from an earlier arrangement of their bedroom decor . Mike could hear the mens' hands slapping against their bare skin while they wanked to these images of his naked step-mom getting pounded by his dad.

When Mike returned to the pool area, a few cat calls shot up as Stacy and Hillary entered the pool deck. Stacy was wearing the same high waisted throwback cheetah print bikini she wore to the beach when they had teamed up with the Diazes. The gold top held back her round dark brown cleavage. Hillary wore a blue and white striped one piece that fit tightly to her boney hips and hand a plunging neckline that covered her pert breasts with only thin strips of fabric. They held hands as they crossed the pool deck to Mike.

"Nobody told you, yet? We're the warm-up," Hillary flirtily informed him before pushing him down into a deck chair.

She turned to Stacy, reached around to softy take a handful of hair, and then kissed Stacy passionately on the lips. Naked couples all around the pool froze to watch the two young agents' sapphic display. Ted, the firm's effeminate design expert who'd been known to flirt innocently with Mike on more than one occasion, stood up from a nearby chair and untied Stacy's bikini top. She pulled away from Hillary for a moment to allow him to pull it away from her delicious breasts and Hillary replaced the top's support with her own hands.

The pair went back to exchanging long delicate kisses and Hillary fondled Stacy's nipples. Hillary turned around and grinded her ass into Stacy's crotch in rhythm to the bass of the pounding music. When Hillary stood up, Stacy pulled open the tie at the back of her neck, letting the fabric covering her breasts fall to her waist. Hillary's fair skinned breasts jiggled as she sook her ass. Slowly, Stacy pulled on the material around Hillary's waist. It unfolded down past her hips and then Stacy slid the fabric all the way to the floor letting everyone with Mike's view a look at the top of her friend's bare pussy lips.

"OK, you've all waited long enough, let's go," Stacy announced. Mike could hear the pool loungers and players exiting the pool and leaving their chairs. Hillary took Mike's hand as they passed and headed toward the theater with him in tow.

When Mike and HIllary reached the theater, the men inside had rearranged the furniture. The leather benches were now up against three walls of the room. Against the wall under the screen was an inclined cushy leather inclined bench with fixed stirrups on either side of the bottom.

Hillary worked the room, saying hello to several of the older men sitting on the benches and flirting with the clients and their wives who were filing in with drinks in one hand and their husband's cocks in the other.

"OK, who wants to help my mom celebrate ten years with the firm?" She asked, circling the middle of the room. A cheer rang up. "Awesome. If you want to kick this off, then I'm going to need see some big hard dicks!" With that, Hillary pulled Mike's trunks to his ankles, eliciting another round of cheers. She winked at Mike from her knees and then slipped her mouth over the tip of his penis, sucking at the top while she played with his balls with the tips of her fingers..

All around Mike, clients and employees from the firm were watching Hillary play with his erection. Some of the men who were jerking off to the video of his parents fucking were jerking off while they watched Hillary pleasure Mike. In other parts of the room, couples were playing with each other while they watched. He noticed Ted from IT had pulled off Stacy's cheetah print bottoms. She was bent over a bench and he was licking her between her thick brown ass cheeks. Feeling this many eyes on them at once gave Mike a thrill.

Moments later, as his step-sister sucked his testicles for the crowd's amusement, another cheer erupted. His father entered the room in a white fluffy robe. He sat on the edge of the bench at the front of the room with the front of the robe hanging open, surveying the action. Maria emerged from the crowd - her tan round ass and breasts bounced delicately on her thin frame as she made her way to the front of the room. She squatted in front of Mike's father, and nimbly went to work licking his plump ball sack while he jerked his own shaft. Mike enjoyed watching her thick ass splayed out near the floor while Hillary sucked his dick.

After a few minutes serving as eye candy for the crowd, Hillary stood and led Mike toward the front of the room. He watched her athletic ass cheeks bounce while she half-skipped across the floor. Hillary leaned down and pulled Maria's ass up until she stood parallel to the ground while she licked Mike's father's hard shaft. Maria turned backward to see who was tonguing her slit and smiled when she saw Hillary's face between her legs. Hillary whispered something to Maria, who nodded enthusiastically.

With one hand pulling apart Maria's ass cheeks, Hillary guided Mike's erection between her thighs and into her wet slit. Voices in the crowd cheered the threesome on as Mike and his father spit-roasted the spicy receptionist. Mike took his strokes slow and steady, not wanting to finish too early.

He only got to spend a couple minutes thrusting his manhood inside Maria's slick opening before he was gently pulled away from behind. The front of the room was cleared, save for his father sitting on the bench slowly throttling his erection.

"Ladies and gentlemen, Mrs. Tamara Emerson!" Stacy enthusiastically introduced the guest of honor over a microphone.

Mike's step-mother entered the room to applause and cat-calls. She wore a fishnet body stocking that Mike could see straight through to her thick matronly breasts and silver dollar areolas. The stocking was crotchless, allowing the room to get a good view of the dark tuft of pubic hair between her legs. The now completely nude Stacy held Tamara's hand above her head so she could spin around on her tip toes for the crowd.

The two thick bottomed women made a short lap around the semi-circle that formed at the front of the room and then Stacy spun off into the crowd when Tamara approached her husband, who was still leaning on the inclined bench. Tamara leaned into Mike's father, placing her big tits right up in his face and then slid down the front of his abdomen until she was crouched in front of him like Maria had earlier. Lacking any partner available to him at the moment, Mike reached his hand to his own stiff prick and began steadily stroking while he watched his curvy step-mom fellate his father's impressive penis.

Tamara didn't overstay her welcome at the base of her husband's cock as she soon stepped up and pulled him from his perch. She tossed his robe to the corner of the room, exposing his beefy muscles to the crowd. Her now-nude partner helped her get a seat up on the inclined bench and settle her bare feet on stirrups at the base of the bench.

Mike's father spread Tamara's legs and knelt before her. He pulled apart her thick lower lips and used his tongue to lubricate her opening. To Mike's right, a line was forming to wait for an opportunity to get in on the action while the spectators around him simply crept forward in their semi-circle. As he got closer, Mike could see Tamara's thick tits begin to bob and rotate as his father began to thrust his cock inside her.

Two men worked their way to the front as Tamara beckoned. Mike recognized them as two of his father's oldest friends. From the left side, Billy Jensen was now receiving a handjob from Tamara while Mason Fairchild stood to her right and was halfway inserted into her mouth.

Watching his step-mother get filled up by two cocks while she jerked another one made Mike's cock feel like it was going to explode so he let it flop in front of him and drifted toward the side of the room where the line was forming to get into the action up front. Mike took at seat on a bench that was about fifteen guys back and looked across the room to see the Princetons from the first deal he'd helped close. Chelsea was riding Royce in a reverse cowgirl position while a third man slipped his erection between her lips. Even amidst the orgy going on around him, her her long lean naked body was a sight for sore eyes.

Re-focusing his attention up the line, Mike noticed there was some movement as the line was shuffling forward. He could see the front of the room again and a new man had taken up position between his step-mother's thighs while another was pressing the head of his cock into her mouth. In the corner behind the action, his father and his buddies were slowly pleasuring themselves while they watched the action.

He was just beginning to wonder how long it would take before he reached the front of the line when the line broke up a bit as Stacy, Hillary, and Maria sorted the men into groups. Maria pushed Mike back into the wall alongside the man in front of him. She aggressively dove down onto Mike's erection while she stroked the man next to him. After a few moments on Mike's dick, Maria moved her mouth to the next man in line while she continued to wrench her fingers around Mike's erection. Up ahead in line, Mike watched Hillary performing a similar service to a couple of older men while Stacy tasked herself with preparing the men about to go penetrate his step-mother.

The line shifted forward again and the men who stepped up helped Tamara spin around. The new man up dribbled a small amount of lube from a tube onto Tamara's anus and then slipped his finger between her cheeks before sliding the tip of his cock into her ass. She turned back to watch him and her face lit up as he started to thrust into her backdoor. Soon, she was preoccupied with sucking another dick, though.

When Mike finally reached the front of the line, Stacy was sending the prior line leader off to fuck Tamara with a slap on the ass. She turned to see Mike staring down at her.

"Ah, hell no," she laughed and ran back into the line to get Hillary. "They can take care of themselves for a minute," she said and then dropped to her knees, pulling Hillary with her.

Mike looked down at Stacy's thick dark lips as the swallowed his shaft and then at Hillary's rosy red lips as they attempted to devour his balls from the side. Watching this fantasy come true in front of him was almost too much to handle. Thankfully, Stacy slipped her mouth off the tip of his cock with a pop as the suction broke and moved to capture his slipper cock between her big brown tits. The stimulation from her soft breasts was enough to keep him hard but not nearly as intense as the suction between her lips.

The big moment finally arrived and Stacy held Mike's hand and led him up to his step-mother's padded bench. Someone earlier had pulled her body stocking down under her tits and they were now hanging down over the seam for the neckline. Her chin glistened with cum below her lower lips and a stream of white semen decorated her bouncy rack.

"There's my big hard boy," Tamara whispered in his ear as he slipped his cock into her slippery opening. It was warm and sticky from the cum that men had deposited inside her. As he fucked her vagina, semen leaked out onto the shaft of his cock and created a frothy lather.

"Hold on... hold on!" Mike heard a familiar voice from his left. It was Hillary, leading his father by his hard dick back to the front of the room. She leaned into whisper something to her mother. Mike watched Hillary's tight tits fall forward as she spoke to the older woman. Tamara smiled and nodded and then pulled herself up off MIke's cum-lubricated penis. She leaned to the side to let Mike's father lay on his back on the bench and then he helped her mount his pelvis using the stirrups on the bench for leverage.

Hillary helped Mike's father slip his thick erection into Tamara's opening once more. Then, she leaned forward and took hold of Mike's shaft.

"Remember this?" she asked, referencing the fantasy she'd once laid out for MIke in a late night rendezvous. She pulled him forward and guided the tip of his cock overtop of his father's shaft and inside his step-mother's eagerly awaiting pussy.

Mike shifted forward and could feel the tight strain of Tamara's opening on top of his shaft while his father's thick hard-on began to glide in-and-out of the opening below him. Tamara leaned into him, letting her big tits press up against his muscular chest. She grabbed him by the back of his head and pulled his mouth to hers, giving him a passionate and sticky kiss. Mike's mouth lowered so he could suck on each of her rock hard nipples while he felt the squeeze of his parents genitals around his cock.

"Oh, god, Mike, you're just as big and hard as your dad," Tamara whispered to him as her breasts shook below him. "Fuck me so hard. I'm going to cum on both your cocks." Mike increased his pace and his father and his shafts were pumping other men's cum in and out of her opening. Finally, Tamara wailed, "Oh fuck me!" And a small amount of semen and Tamara's own liquids streamed over Mike's cock.

That must have been all his father could take. He pulled his dick out from inside Tamara, breaking the seal with Mike's shaft, and began pumping his shaft with his hand. Hillary must have recognized her opportunity to strike because, before Mike could blink, she had seized both of their cocks between her hands. She was now pumping Mike and his father's shafts as one. Mike felt a wave of ecstasy take him and watched the two tips erupt as one and pump streams of hot semen up and onto Tamara's vaginal lips and soft belly.

Hillary hungrily took Mike between her lips and sucked the last of his fluids into her mouth before doing the same from the tip of his father's cock. She smiled up at Mike and a small stream of their gift escaped the corner of her mouth.

The crowd went wild after watching their family escapades. They were amongst a lot of kink-loving friends and it appeared the display was enjoyed by all of them. Stacy rushed over to plant another kiss on Hillary's mouth, eager to share the milky fluids escaping her lips.

After the two young women finished a deep breast-to-breast kiss, they helped Tamara off the bench and Mike and his father supported her under each arm as they led her to a nearby bathroom. Mike's father turned on the water while Mike helped her strip off her body stocking turned cum rag. He helped her up into the shower stall and then followed her in. Tamara handed Mike a clean washcloth hanging from the bar on the wall and he dutifully wiped her breasts clean from the sticky cum that had permeated her bodystocking.

When Mike's wet rag reached the folds between her legs, she pressed his hand into her thick folds and slowly rocked it up and down. Mike looked at the lustful gleam in her dark eyes, dropped the rag, and slipped his fingers inside her folds instead.Tamara placed a hand under her hanging breasts for support while Mike ramped up his clitoral massage. He turned his gaze back over his shoulder and found his father was pumping his hand at a renewed erection while he watched his son play with his wife's pussy.

After a few minutes of listening to his step-mother's moans and groans echo off the shower's ceiling, Mike watched her breath suddenly grow rapid. Her giant breasts rose and fell with her orgasmic breathing and she slumped into him after he finished her off. Behind him, Mike heard his father grunt as he finished himself and then they swapped places.

Mike exited the shower, looking back to see his parents kissing passionately under the streaming water. When he closed the bathroom door behind him, he could hear a ruckus from the theater as the reverie was just ramping up. Mike turned back toward the pool, though, and headed up to his bathroom where he showered and then collapsed into his bed. He quickly fell asleep having completed more than he would have ever imagined entering the summer.