Chapter 5

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—but 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 she 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 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 that spouted 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 down her throat.

*****

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, 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 there 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 have 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 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.