Gangbang With the Boss's Daughter - Cover

Gangbang With the Boss's Daughter

by Peter Duncan

Copyright© 2023 by Peter Duncan

Erotica Sex Story: Ashley McClain whose father owned McClain Construction had been having sex with the key men of his firm since she had been in high school. After the Senior Prom, she arranged to have a gang bang with the five men she had been enjoying sex with.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/ft   Fiction   Gang Bang   Anal Sex   Analingus   Double Penetration   Oral Sex   .

One night at Ricky’s Skip said to Darren and the rest of the guys, “Darren and I were in bed with Ash today and she said she thought a gangbang might be fun.”

Both Sam and Nick who had been in gangbangs before picked up on it, and Darren and Skip were interested. Greg was turned off. While originally feeling too close to Jim to fool around with his daughter he realized that even if Jim found out about it, he would refuse to believe it. The man he had so much respect for when he hired him turned out to be completely clueless about his daughter’s exploits with men ... as well as his wife’s. Nick is fucking his wife for Christ’s sake. His main concern about participating in a gangbang, whether with Ashley McCain or any other woman, was his fear of growing soft in the presence of the other men and, losing his hard-on because of performance anxiety. He once turned down the opportunity of “doing” Ashley in one of the Hyatt bedrooms with another one of the guys, confiding to her that he didn’t think he would be comfortable having sex with her with another man present. But the tenacious Ashley decided to test his fear by pulling it off when she was riding in Greg’s truck with him and Skip. She was in the middle. Kissing Skip when she went down on him.

“For CHRIST’S SAKE Ash,” Greg bellowed, “someone’s liable to SEE us.” At the same time, the sight of Ashley bobbing on Skip’s cock gave him an immediate hard-on.

Knowing that Greg was turned on by what she was doing to Skip, Ash sat up, kissed Greg’s cheek then tongued his ear. Fumbling his cock out of his jeans she went down on him under the steering wheel, her head thumping against it as she bobbed on him. From the way it was pulsing against her lips, she knew he wouldn’t last long. When he shot in her mouth she swallowed then moved back to Skip’s and got him off as well. As she licked her lips she said, “There, wouldn’t you both like to fuck me?” At lunchtime, they checked into a no-tell motel where they had a threesome. Greg didn’t have any trouble keeping his erection up.

When she set up the same kind of ride with Nick DiAngeli and Sam Glickman neither man flinched when, sitting between them in the truck, Ash took out their dicks and got them both off with a dual hand-job. Having been in the business for a long time, these men shared “company projects” before. But, when the boss’s stunning daughter vacuumed their semen from their cum-covered cocks and licked her fingers dry, it was an even greater treat for both of them.

They were on their way to a medical center where they were remodeling a group of doctor’s offices. When Ashley told them how exciting it was to be in the stirrups being examined by the doctor, they knew they were in for a great afternoon. They took turns fucking their young coworker with her feet in the stirrups. At the same time, she sucked the one, not in the saddle. Nick wanted to do her in the ass in a DP. But she told him it wasn’t going to happen. “I’m sorry Nick but I think my young ass is just too tight for that.”

One evening at Rick’s it was Darren who finally said, “Ash said she’s toying with having group sex with us. Can you believe it?”

Greg laughed when Skip said to the young Darren, “I think you’re too much of a pussy to get involved in a gangbang, Darren.”

“What do you mean by that,” he retorted. “Have YOU ever done it?”

With a wide grin, Skip looked around at his other three co-workers and said, “We have in fact. How can we ever forget Margo Vincinsky?” Margo was a female building inspector who worked for the county. She was a nymphomaniac who gave lenient inspections to contractors who took care of her needs. “But then,” he mused, “she isn’t a young chick like Ashley McClain.”

“Yeah,” Sam Glickman replied, “and she wasn’t the boss’s daughter either.”

By any stretch of the imagination, Ashley was no Margo Vincinsky. With Margo, it was a sickness. She needed to fuck like most people need to eat. With Margo, there was no such thing as sexual satisfaction. She just needed it incessantly. Even multiple partners didn’t do the trick. Had it not been for her father being the head building inspector for the county, Margo’s sexploits would have gotten her fired. But it was her father who started it all when his daughter was in her teens. She became famous within the building department, as well as local government in general. There were no male construction workers in the county that had not been inside Margo’s pussy, often in the company of other men.

Ashley had developed her stable though, one made up of older, quite satisfying men ... men who could only teach her more about sexual pleasure. Her goal was to be so knowledgeable and sophisticated in the way of sex that she would be able to control any man. Though she loved her dad dearly, she did not want to end up with a man as naïve as Jim McClain seemed to be. It started as a game to her. But because her father couldn’t recognize what was going on with her it became an affront to her sensibilities.

Everybody in the local building industry, now including Ashley, knew about Margo. She couldn’t escape knowing. Every time Margo did an inspection, Ashley could sense the pheromones generated by the men’s lustful thoughts. Being a natural snoop, she overheard three of her male friends talking about being with Margot and six other guys. She was too young to understand that Margo could not achieve satisfaction. But from that day on, being ravished by her five men, and only those five, was a growing obsession. It would take careful planning, but she knew she was going to pull it off.


The young Ashley McClain was extremely attractive and much sought after by boys in school. But she never dated. When she took an art class with Hartley Frasier, they became friends. He was not pushy like the other boys. Though they didn’t officially date they spent time together after school. Hartley confessed to her that he was gay but had not yet come out of the closet. He liked being with girls, but he didn’t want to be involved with them sexually. It was perfect for Ashley, totally non-threatening.

As they became better friends Hartley began confiding in Ashley about his fantasies, one of which was to have sex with more than one boy at a time. Ash confided that she would like to do it with multiple sex partners in the same way but would never consider doing it with boys even close in age to high schoolers. She told him about her “men” and her desire to have group sex with them. “But I don’t know how I could get away for a night to do it.”

It was Hartley who came up with the idea. “Why don’t you let me take you to the prom?” Prom night always ended up in an all-night party, either at someone’s home or a motel where the participants shared in the cost. Hartley was a handsome young man but was virtually unknown at the school, except for another gay boy and Ashley. She had a greater awareness of gender issues. Hartley was only one who knew of Ash’s sexual exploits and, in a way; he was living vicariously through her.


It was with Sam Glickman, the oldest of the married guys that Ash set up the prom night affair. By his greater group-sex experience, which included Nick DiAngeli in some of them, it was Sam who sold the deal to Greg, Skip, and Darren.

Nick was in at the mere suggestion. The other three had to be sold on the concept. Each of those had the fear of being found out by Ash’s father and losing their jobs. Nick and Sam knew that Jim McClain was too much of a goody-goody to accept the concept. In fact, over the years, Nick and Ashley’s mother had carried on an affair. But that’s another story dealing with Jim McClain’s namby-pamby sexual attitudes.

The plan was for Hartley to pick up Ashley in a limo that would be paid for by Ashley’s father. She would be dressed in her prom gown and take a bag of clothes for the all-night party that she told her parents was being sponsored by a classmate’s family. The “McClain Construction five” would rent the motel room. Ashley would go to the prom and leave at 9:30 with Hartley. He would drop her off at the motel, then pick her up in the morning in his father’s car and take her home.

At the dance, Ashley McClain’s contemporaries, her friends, and a couple of those who were not were jealous of her being squired by one of the most handsome and yet most mysterious boys in the class. Most thought Hartley was stuck up. Some knew he was reticent and shy. A couple suspected he might be gay but were not convinced of it. Regardless, the stunning couple was the object of conversation among the many prom attendees. When, at 9:33, Hartley escorted Ashley out of the Hall everyone wondered why they were leaving early, and where they were going.


Since Sam Glickman had prior experience in setting up “group gropes” he was elected to secure the room and stock it with beer and snacks. For those who surf porn, you would know as a typical room: two queen-sized beds with green Aztec patterned spreads, two wall-mounted adjustable polished lights with ecru shades on either side of each bed, a nightstand with a lamp, a phone, and an alarm clock. On the long wall were two southwestern paintings. There was a dark green easy chair by the door and a table in front of the window with two mahogany chairs. A mid-sized, flat-screen television was mounted on the wall across from the beds. This room had been upsized with a larger sitting area between the bed and the outside wall.

At 9:41 Skip and Darren knocked on the door. Greg and Nick came about five minutes later. At 9:49 a white limo pulled into the parking lot. The limo driver got out and walked around to let Hartley and Ashley out. He watched as Hartley, holding Ashley’s arm, escorted the stunning girl, in her prom dress, to the base of the stairs and walked up with her. He watched them stop in front of the door and knock. The door opened. The girl kissed the boy on the cheek and then whispered something in his ear. He watched the boy whisper into hers. He had no way of knowing that Ashley said, “I wish you could come in and watch.”

Or that Hartley said, “I wish I could too. I would just love to suck all those cocks both before and after they were in your pussy.” With a rueful chuckle, he added, “Those guys would probably just beat the shit out of me though.”

When Hartley came back to the limo the driver asked, “Weren’t you invited to the party?”

Hartley merely said, “Wrong kind of party.”

When Ashley came into the room she looked like a princess. Each of the guys was dressed either in Levi’s or chinos. Each had a bottle of beer in his hand. They were talking in hushed tones, laughing nervously. It became eerily quiet as they stared at the boss’s beautiful daughter, in her elegant prom dress. To a man, it seemed like a strange, yet enchanting way to begin such a raucous evening. Their gangbangs had always been with a hooker, or someone’s frustrated wife, none of whom were as cute or stunning as the young Ashley McClain.

As witty and self-assured as ever Ashley cocked her head and asked, “Did I crash the wrong party?”

Starting with Sam, who had secured the room, she gave him a sensuous, open-mouthed kiss. As she reached and fondled his emergent package she said, “Thank you Sam for making this possible.” She giggled. “I see that my presence is affecting you already.” Working her way through the remaining four she kissed each with a gaping mouth, tonging with them sumptuously and giving each of their stiffening members a grasp. When she got to Darren, the youngest, kissed him even longer.

Because of his age and naiveté, the other men always put Darren at the end of the line. Ashley’s most sensitive area with these men was her age. She knew Darren, didn’t have the same advantages and had to pay his dues. She also knew she had control of five of these men, if for no other reason than her connection with her father. But she wasn’t going to encourage them to make Darren take “sloppy lasts.” Kissing him longer and more passionately than she had the others, she not only fondled his cock, but also unzipped him and stroked his exposed member. He was the one she had tutored to make a better lover and the one with whom she had enjoyed so much more sex during her time at McClain Construction. Letting the other men know how much she favored Darren she emphasized her sensuous kiss and stroked his rock-hard penis in plain view of all of them. Then as if she were greeting the Prince of Wales she curtseyed then dropped gracefully to her knees. She knew Darren wouldn’t last long; he had always been the one the other men made fun of. By giving Darren such preferred attention, she hoped the other men would take her deference to include him equally.

Darren’s cock was shorter and thinner than the others. Because of this, he had been her first deep throat. Looking up at him with affected, doe-like eyes Ashley bobbed on his cock, coating it with her saliva. Then, with each thrust forward she took him deeper inside, gagging until his glans almost touched her vocal cords. Within a couple of minutes of throat-fucking him, the young man spewed three bursts of splooge down her prom-girl throat. His knees trembled so visibly that he almost collapsed. As she pushed a white trickle from the corner of her mouth she looked around at the men in her stable and smiled.

To a man, they all had their dicks out and were stroking, each wondering who would be next. She had a plan though. For the last summer, each of them had mentioned deep-throating. Because of Darren’s diminutive size, he had been the only one with whom she had done it. She fully expected that once the others had seen her doing it to Darren, they all would want it. Logic told her that her throat should be stretched on a gradual basis. Since he was the next smallest, Skip would be next.

She knew that her gagging brought out sadistic pleasure in Darren and understood that the other men were awaiting their turn to enjoy the experience. During the second time (with Skip) she was able to control her gag reflex. Taking Skip’s bulky head down her throat, she emphasized the gagging, bringing forth gasps and comments of excitement from the other three men. Having gotten used to Darren she was now feeling extra nasty and looked forward to mainlining their loads.


That first day on the job had been an eye-opener for the fourteen-year-old Ashley. As she lay in bed that night, she thought about having sucked both Greg’s and Skip’s cocks and asked herself the question, “Am I a slut, or do I just love the idea of sex that much?” She was surprised at how much she loved the feel of those pulsing, masculine power symbols in her mouth: how her tongue explored the contours, the muscles, the veins, and the smooth, taught heads. Having heard from her friends about the unpleasant taste of semen she anticipated the “nasty” surge that would soon be coming and wondered if she would like the taste. The sweet seep (precum) from their slits that she tasted while she was sucking them surprised and delighted her. When Greg had ejaculated that day, she didn’t consider it unpleasant at all, just unexpected. The second time that day was more notable; Skip came in much greater volume. As far as taste goes, Greg’s was garlicky. Skips was just a little musky. I can easily get used to both of them, she thought.

Something else struck her about the two different men that day: While she was going after Greg’s cock, he half-heartedly tried to talk her out of it. After he finished spurting his essence though, she felt his resentment and then his immediate rejection. Expecting the same from Skip later in the day, she was surprised how, after he came in her mouth, he caressed her like she was a kitten, talked with her in endearing terms, and let her know that sex was something he would like to do with her repeatedly.

Ashley had explored her own body for as many years as she could remember. It always felt good. And the day her clitoris first swelled and sent shockwaves throughout her body she knew she was hooked. It was not until the girls at school started talking about “giving head” that an unfulfilled desire to know what a tumescent penis would feel like began. There were rumors about the head cheerleader, Maggie Matheson, sucking off the entire football team in the locker room. That was about the same time she thought she had become addicted to popsicles. It had as much to do with her fantasizing about the feeling of a phallus, the same size as a Popsicle. For a while, Ashley was obsessed with cream-filled Slim-Jim donuts. But having already had two real men’s cocks in her mouth, the cream she experienced was not fattening, but a healthful protein load.

She had thought about dating boys in her class. But after listening to the way some of them talked about their girlfriends she decided that, if she was going to get involved sexually, she was going to do her best to protect her reputation among her peers. As far as she was concerned what she did sexually was her business. Instead, she started thinking about the men who worked for her father. They had come to her home every year for the annual company party. Their obeisance to her dad made her wonder if she could experience the same kind of regard from them. But how am I going to make it happen? Each of her sexual fantasies started with this kind of challenge. The challenge was answered that day she first went down on Greg Sandler’s cock.

In the motel room five men, most now with limp dicks gaped at her in silence. To bring them back to the awareness of her importance to the party she asked, “Well, isn’t ANYBODY even going to offer me a beer?”

“Sorry,” said Sam Glickman, quickly fishing a beer out of the cooler and opening it. He wiped it off, handed it to her, and said, “Ya know Ash, we’re all accustomed to a girl in jeans and a t-shirt ... maybe a skirt or shorts, not a god damned beauty queen.”

She held her beer out and said, “Well thanks for the compliment, Sam. But it makes me wonder what you are going to do to make this princess feel like a well-served woman.” The comment brought a round of nervous laughter. Exercising control over the situation Ashley went on, “Everyone is a bit nervous. This princess though has just been to a ball and is looking for a ball of a different kind. Is anyone interested?”

Smiling, she touched beers with Sam, patted his soft crotch, and batted her eyes. “You’re the leader here Sam and you’re not even offering your princess something she can get a handle on.” Incredibly self-assured she realized that Sam, along with all the men was uncomfortable. “Here Sam,” she said. “Hold my beer.”

Surprised at the ease at which the mature-acting, elegantly dressed teenager took control of the party, Sam took the bottle from Ashley’s hand. “Maybe this will help, she said.” Dropping to her knees she toyed with his mostly limp member, slapping it into a pendulum swing with her index finger. After it had winced and started rising, she took it in her hand and kneaded it. Looking up she smiled and stroked it as it filled to an erection, then took him in her mouth.

As the gown-clad teenager sucked him, Sam, with a perpetual smile, looked around at his buddies. He winced when Ash’s well-practiced tongue licked the groove under his glans, his flexing knees dipping and raising him as she worked his sensitized sex in her mouth. It only took a minute of Ashley’s expert tonguing to touch to flip all the switches and he said, “Careful honey, you’re cocking old Sam’s gun.”

Moving her mouth off his swollen phallus she looked up and said, “Why should I be careful Sam? We have been through this enough before. Besides, we had all night (she winked) and smiled around the room. “From my experience, I know you can find more ammunition for your next hunting expedition.” Jacking him to greater hardness she took him back in her mouth, her head bobbing with greater purpose. Sam was embarrassed that Ashley made him come so quickly. Even though he had sex with her since her first summer at McClain Construction, he still could not keep from misjudging her. Nonetheless, he was glad that the decisive girl was finally getting the party going in the right direction.

Her gown rustled as she stood up. With her little finger, she wiped a trickle of cum from the corner of her mouth then wiped her chin with the hollow of her hand. After sucking her finger clean, she said, “Is anybody going to help me out of this dress?” To a man, they had all been mesmerized at the sight of the beautiful, gown-clad high school girl sucking off their friends. Like bees in a hive, they gathered around her. Greg undid the back of her dress, helped her get her arms out of the top, and let it fall in a drape around her hips. Darren and Skip lifted the hem. As Ashley raised her arms, they both lifted and peeled the long dress over them. They had all seen Ashley naked enough times before, mostly after having taken off her jeans and t-shirt. Now, as she stood before them in her sexy red panties and bra, her dove grey thigh-highs, and her red, peau de soie pumps, she could easily have been a model at a Victoria’s Secret Fashion show. While each had been impressed with her youthful beauty, what they saw now was way out of context with what they were accustomed to. Each of them realized how lucky they were that this party had been put together tonight. Except for Darren Dole and Sam Glickman, who had just been desensitized each of the others longed to be on her smooth young body with their cocks inside her familiar, tight cunt.

“Don’t take too long getting ready, fellas,” she cajoled. In a muddle of unbuckling and unzipping, pulling shoes off and stripping socks ... peeling off shirts, and stepping out of pants Ashley scanned the naked men, all now with pulsing erections. She chuckled that these were the only men she had ever seen naked. If Daddy only knew. Deep down she wished her father could be here leading his men into action. But with all this nakedness and all these hard-ons in a motel room, all she could do was shake her head and say, “WOW!”

Feeling devilish she walked to each man, shook his dick, and said, “Nice to meet you this way,” or “I’m Ashley,” or “I’ll be at your service, will you help?” or, “I hope you feel this good inside me, big boy ... maybe you would like to join a couple of your friends.” She could feel by the tenseness of each man’s body how much they wanted to accommodate their lust. Going back to Sam Glickman and fondling his still flaccid penis she said. “Don’t worry Sam there’ll be plenty for you; after you get back up to speed.”

Finally having enough of her teasing Greg started by taking her in his arms and kissing her. He had been her most reluctant sex partner since she came to work for the company. Skip Furman went immediately behind her and unhooked her bra. He coaxed Greg back a little so he could peel the straps from her shoulders and let the red-colored lingerie fall to the floor. As he pressed his naked body against her bare back, he cupped her breasts in his hands. His cock slid between her legs, grazing the bottom of Greg’s that was up against Ashley’s pussy. “Mm, nice start,” she cooed.

Greg chuckled, “Never thought I would be touching another guy’s cock when I had a girl in my arms.”

“CHRIST,” Skip said, “This is weird as hell but it’s so fucking hot.”

Darren laughed nervously. He and Ashley had been the most consistent sex partners. But though it had been something he was accustomed to for these last three years; he was self-conscious in the midst of men he had never seen this way.

Nick and Sam were comfortable being naked in the presence of their peers. They had experienced group sex enough before. But Darren had two other issues: He had the smallest penis in the group. Then, in his youth, he had several sexual experiences with an uncle and father which caused him to question his sexuality. Fearful of getting caught ogling the other men’s hard dicks, while envying the other men’s more generous endowment, he self-consciously stroked his more diminutive cock. But the specter of Ashley in the sandwich between his two naked co-workers not only excited him from a hetero-sexual aspect it also brought forth memories of his experiences with his dad and Uncle Dan. This caused him to wonder what his co-worker’s cocks would feel like in his mouth and ass. The feeling grew so intense that he was on the verge of ejaculating.

Ash pushed on Greg’s abdomen, separating his cock from between her legs. She looked down at the promontory of his erection, looked into his eyes, and smiled. “Very appetizing.” Taking his cock in her hand she tilted it upward and sucked his helmet between her lips. Greg winced, flexing his legs up and down as her tongue tantalized the groove on the bottom of his glans.

Pulling back, Skip hooked his thumbs in the waistband of Ashley’s red lace panties and peeled them over her hips and then down her legs. She stepped out and then dropped to her knees.

With their cocks in their hands the other three naked men looked on as Greg laced his fingers in Ash’s blonde hair, guiding her head over his cock. His cock glistened as he fucked her mouth with the increased coating of the teen’s saliva.

Dropping to his knees Skip caressed Ash’s tight, smooth bottom, gripping her cheeks, and opening them, exposing her light chocolate rosebud. As he licked the puckered moue with the tip of his tongue Ash voiced a high-pitched impassioned moan though muted by Greg’s mouth-filling manhood it was still loud and unmistakable.

For Ashley, this was the perfect start. She always loved sucking cock. But sucking one cock, while having her asshole licked was a new experience for her. The additional novelty of having three naked men with their cocks in their hands, waiting for their turn, sent fingers of pleasure throughout her entire body. She realized that her cunt was flooded with her essence, and she was close to orgasm. Wanting to come in her mouth and complete this initial phase, she knew how controlled he was and needed more work.

Skip wanted to eat Ash’s sweet, young pussy but his position was all wrong. Sitting up he propped himself on his hands and scooted feet first under her ass and pussy. Now completely on his back, he pushed up on her bottom with his hands. Clearing enough space for his head, he eased her back down until the lips of her pussy nestled in his mouth. Working his tongue in Ashley’s juicy vulva, he found her distended clitoris and fluttered it wildly. As pleasure morphed into throbbing surges the young girl’s muted squeals increased. Pressing down on Skip’s mouth she wiggled her ass while cradling Greg’s balls in her left hand, bobbing more eagerly on his cock. Reaching down she grabbed Skip’s cock and began stroking it.

Though Ashley was only seventeen and in the throes of orgasmic sex, she was still the one person in the room most in control of her faculties. At home, in the classroom, at work, or on the soccer field she had always been positive and self-assured. She knew she had a way with men and had an edge in dealing with them, even when they were significantly older. But even though she was comfortable with these five men, ranging in age from the low twenties to the low fifties, she knew that male animals could get out of hand in a way that could be harmful to her. The cards were stacked in her favor though as she thought If I should lose the edge with my wiles, I could always keep these male animals in check by holding Daddy over their heads. She was extremely comfortable in this bawdy, sexual romp. In her mind, this was going to be the only time she would involve herself in this kind of debauching. As far as the men were concerned there was no order to what they were doing.

Both Nick and Sam had been involved in gangbangs before. But in those circumstances, they were just part of the herd. With Ashley, they were following her direction. On the floor with Ash, Greg and Skip were idling at the moment. Darren, now out of the mix, felt prickly about the whole thing. He didn’t know what to do.

Ashley recognized the need to maintain order. Compelled to give direction she took her mouth from Greg’s cock and said, “I’ll straddle your cock Skip.” To Nick, she directed, “I want yours in my mouth. Sam and Greg, get on your knees ... I’ll jerk you off.”

These five men who had been enjoying the sexual pleasures of the teenage girl for the last two years had originally thought she was just a horny girl. But it wasn’t ‘til now that they understood they were just willing stallions in this clever girl’s stable. But the calculating teenager was more seductive than controlling, exerting just enough power to keep things from getting out of hand. Each man began to see that Ashley had always been leading the parade.

Accepting this fact, they were relieved that she was taking the responsibility off their shoulders. Greg, as foreman, was a bit miffed at losing the edge. But since they were doing something risky relating to their jobs, he felt sure that Ashley would accept no more abuse than she was willing to take. If Jim ever finds out, we’ll be lucky if all we have to do is look for another job.

Easing her ass up to position her pussy just above Skip’s cock she encouraged Nick to lay down on her left side and Sam on her right, wrapping her fingers around each one’s erections. As she took Greg’s cock back into her mouth, she let gravity do its thing and slid her pussy totally down Skip’s bulk. Four cocks, she thought, this is FUCKING HEAVEN.

 
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