Part 3 of 8. Each part is self-contained and reading previous parts is not essential to the continuity of the story, but several recurring characters are only described in detail on their first appearance.
Part 1: Ashleigh's Ride Home. Ashleigh misses her ride home after cheerleading practice.
Part 2: Ashleigh's Game Day. Ashleigh and the other cheerleaders help their football team in any way they can.
Part 4: Ashleigh's Winter Ball. Ashleigh goes to her sorority semiformal.
Part 5: Ashleigh's Christmas Break. Ashleigh goes home for Christmas.
Part 6: Ashleigh's Spring Break. Ashleigh goes to Cancun for spring break.
Part 7: Ashleigh's Summer Internship. Ashleigh gets a pretigious summer internship.
Part 8: Ashleigh Plays I've Never. Ashleigh plays a game with her sorority sisters and recounts her sexual past.
*****
Chapter 1
Ashleigh Holton woke up at noon in Jason's bed with hazy memories of having wronged him the night before, so she sucked his morning wood off before she ate "breakfast" and headed to the library to start her research project which was due the next day. But first, she had to pick up her backpack, which she left at the athletic center after practice on Friday.
Getting into the athletic complex wasn't as hard as one might think for a school known to have rivals break in to vandalize the locker rooms. On more than one occasion, Ashleigh had gotten in just by letting the security guard touch her boobs. Armed with smugness and a fuck-me prep school outfit (black sweater vest, white blouse, pink plaid miniskirt and white stockings), Ashleigh waltzed into the complex's main entrance, hoping to recover the backpack she had left on Friday.
What Ashleigh didn't know is that the cheerleaders' shenanigans the previous day had sparked outrage from their main rivals, the Wildcats, the night before. They had broken in to the equipment room the night before and made off with the mascot's entire costume. In a humiliating blow to security, they were even on high alert and still managed to fuck it all up. Two guards had been fired on the spot and three others placed on administrative leave, which meant that the head of security, Sgt. Bill Harrison, was personally manning the booth when Ashleigh arrived.
Ashleigh knew some shit had gone down from the moment she set foot in the complex. Bill was at least 20 years older than any of the others, and he flat-out told her she'd have to come back on Monday. Ashleigh tried to tell him that she had a big research project due, but he really didn't care.
Eventually, Ashleigh resorted to flirting with the man, twirling her blonde hair and batting her eyelashes to try and make "an exception." Bill noted, with the revised security camera layout, there were no cameras available to point at the control desk. He pretended to be disinterested, at one point pulling out his phone to send a text to his buddy Darryl. As Ashleigh droned on about how appreciative she'd be, he imagined the possibility of her crammed under his desk with his dick sliding in and out of her mouth, and felt his cock stiffen for the first time in weeks ...
Sgt. Harrison cut Ashleigh off abruptly. "I imagine this isn't your first time doing this," he snapped. "So let's just cut to the chase. What are you offering?" Ashleigh was taken aback. She wasn't sure whether the guy was playing dumb or seriously dumb. She wasn't going to just offer to fuck the guy, but it's not like she wouldn't if it came down to it.
It's as if Sgt. Harrison could read Ashleigh's mind. One of the great things about experience was that he had pretty much heard it all before, and knew what people were going to say before they even did. Ashleigh wanted to play the dumb, coy tease but she had probably sucked more dicks than she could count. "Say it," he commanded. "Say what you're going to do."
Ashleigh's self-confidence and Kappa pride evaporated. Never since she'd first had her cherry busted by her first boyfriend had she been so nervous about sex. "I ... I'll suck you ... your dick, I mean ... I'll suck your dick," she stammered quietly. It echoed in the empty foyer.
"Fine. Come around and get under the desk. Someone else is coming." Ashleigh scurried around the counter and climbed into the foot space below the desk. She took off her sweater vest and padded her knees with it as Sgt. Harrison sat in his chair and slid forward, pushing his crotch towards her. He unzipped his pants and let his semi-rigid cock out.
As Ashleigh began taking him into her mouth, she heard the front door open and Sgt. Harrison greet some of the workmen coming in to try and patch together a new mascot. They walked right up to the desk and signed in, not noticing anything unusual as Ashleigh silently bobbed up and down on the dick. Once the workmen walked off, Ashleigh began sucking with her usual vigor, slurping down the salty pre-cum.
Unlike younger dicks, it took a long time for Sgt. Harrison's to become fully erect, but when it was, it was a sight to behold. In his younger days, Bill had never been at a loss for pussy. His veiny, throbbing cock bounced in the morning air as Ashleigh worked her magic with her moist pink lips and her carefully manicured fingers. Bill missed his first job as a nightclub bouncer and getting sucked off by girls almost every Friday and Saturday night. He knew that he'd blow his load eventually, but he couldn't wait to get a taste of Ashleigh's pussy. Maybe he should take the front desk more often.
Ashleigh let one hand drift down to her snatch, locating her clitoral hood and prodding her clit out from its hiding spot. Dicks just always tasted better when she was aroused, and within minutes, Ashleigh felt her pussy juice soaking into her panties.
"Get up," Harrison barked, pushing back from the desk. Ashleigh reluctantly stood up and looked around nervously. "Turn around," Sgt. Harrison sneered.
"No. No ... people might see," pleaded Ashleigh. Sgt. Harrison stood up from his chair, erection jutting out of his pants. He was twice her age, but he knew how to control people. Ashleigh put her hands up to push him away, but he grabbed her wrist and locked it. As Ashleigh struggled, she felt herself turned around bit by bit, until Sgt. Harrison had locked her arm behind her and bent her over the desk. He let go of her arm, keeping her in place with a hand on her back. Flipping up her skirt, he rubbed his dick gently down her ass crack against her silky, high-cut panties.
Pulling the crotch of her panties aside, he nestled his dick up against the entrance to her cunt. "Wow, you're already wet. That saves me some time." With a heave, he lifted her whole body off of the ground, and then basically dropped her wet pussy onto his slimy dick. Ashleigh gasped at the intrusion, as the desk as high and her entire weight was now split between the desk and his dick. Her toes barely touched the ground as Sgt. Harrison used her own weight to skewer her. Ashleigh gripped the far side of the desk for leverage as Bill plowed into her from behind.
A buzzing sound startled Ashleigh. It was the keycard activation on the outer set of doors! Someone else was coming in! Ashleigh tried to squirm free, but Bill held her firmly in place.
"Relax," Sgt. Harrison explained. "Just tell them to sign in."
It was Omar, a painter, who froze as he came around the corner and saw the security guard fucking the shit out of a pretty blonde coed bent over his desk. He wasn't sure whether he should call the police or just give them a moment, or whether he should pull his dick off and start jerking off. She was pretty hot.
"Tell him to come over and sign in," Sgt. Harrison explained again. "C-come over and sign in," Ashleigh muttered. Omar slowly walked over to the desk and nonchalantly signed the sign-in sheet, then scurried off to masturbate in the bathroom.
"Remind him to sign out when he leaves," Sgt. Harrison beamed. "Remember to sign out when you leave!" Ashleigh shouted after him.
Bill didn't miss a beat as the whole exchange went down. Aside from the face that Ashleigh was a damn fine piece of ass, he had been into the whole swingers scene back in the day and was plenty used to fucking with an audience. He just hammered away for a bit, and then fingered Ashleigh's asshole when he thought she was getting wet enough to appreciate it.
The buzzer sounded again as someone else entered the complex. Unlike Omar, Jerry the window repair guy wasn't even phased by the sight of Ashleigh getting plowed. He just sauntered up to the desk and commented, "Day-amn!" as he signed in. And instead of scurrying off, Jerry rubbed his dick through his jeans as he watched pretty young Ashleigh's face contorted in the bliss of deep dick fucking.
"Ask him if he wants to join us," directed Bill Harrison. Ashleigh paused, and Bill slapped her ass hard to jolt her back to reality. "Ask him if he wants to join us," he repeated. Eventually, Ashleigh looked up at Jerry and sighed. "Come over here, I'll suck you off," she offered.
The height of the desk was perfect, allowing Jerry to stand right beside it with his rigid cock squarely at Ashleigh's mouth level. Jerry sighed as she sucked him in, watching as his dick disappeared into this schoolgirl angel. He reached over and lifted up the back of Ashleigh's skirt to get a clear view of Bill's slick dick sawing in and out of her pussy. Her cunt lips hugged his cock with every thrust.
Soon afterwards, Bill's pace slowed down as he milked the last few thrusts he could muster, then pushed as far as he could inside of Ashleigh before blowing his wad. It wasn't much, but his seed was well-planted in the uppermost depths of her cunt. Ashleigh also let a small sigh of relief as the last few pumps of jizz oozed out of his pricktip inside of her.
