Double Trouble

NOTE: Consider this another quickie! This has the potential to turn into a series, and I have a few more ideas for some sequels, but only if you all enjoy it. Let me know in the comments or via feedback if you like this story! Also, please let me know which lady you'd prefer... I'd love to hear what you think. Enjoy!

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With the loud ring of the bell reverberating through the halls, kids closed their lockers, chatting amongst themselves as they rushed to their classes. The school year had only just begun a few weeks ago, and many students were still in a summer state of mind. As the hallways cleared, two boys were in no rush to get to their fourth period.

"Get to class, boys." Susan chided as she passed them from behind, catching them both by surprise.

"Yes, Mrs. Cooper." They replied simultaneously as she strode ahead. As she opened the door to the front office, the young men couldn't help but ogle her bouncing rear end. She may have been older than their mothers, an English teacher with tenure, but her soft curves were mesmerizing, and both hormonal boys found themselves watching closely as she closed the door behind herself, before making their way to their respective classes.

Susan Cooper was a dedicated teacher, and had been at the same school for more than two decades. Her shoulder-length brown hair had streaks of gray running through it, but she had embraced her maturity. Her glasses had dark red rims, which matched the bra that could just barely be seen through her white blouse. Her jeans hugged her maternal hips. She wasn't thin, with a bit of chub around her waist, but that extra chub also went to her breasts, giving her an ample bosom that men couldn't help but notice.

With the door closed behind her, Susan stood alone in the empty front office, collecting herself. She unbuttoned the top button on her blouse, adjusting it to reveal a nice tease of sultry cleavage. It was her free period, and she had found a new way to fill her time: the new principal, Bob Kelly. He was in his forties, younger than her, but they'd taken to each other quickly, and in a matter of weeks had developed a routine. On certain days, during her free period away from horny teenagers going through puberty, Susan Cooper would go to the principal's office, and the two would have their way with each other. He knew her body well, and she loved teasing him, showing how experienced she was.

Typically, during work hours, Bob's secretary, Jenny, would have been stationed at her desk outside his office. However, Bob had taken to sending the young woman out to grab lunch when he met with Susan, so as to not arise any suspicion. With the desk empty, she walked up to his closed office door. Just for safe measure, she unbuttoned one more button, now showing off even more of her pale breasts, before sneakily opening the door as she always did. However, unlike always, Susan froze in the doorway with her jaw dropped.

Before her, Bob sat in the arm chair he kept in front of his desk, for guests to sit in during meetings. His pants were at his ankles, and Jenny was between his legs, with her boss' nine-inch cock in her mouth. Susan gasped, entering the room and shutting the door behind her, her face a mix of shock and anger.

"Bob, what the fuck!" She exclaimed. Jenny pulled back, letting Bob's cock drop from her mouth, a strand of drool hanging from her lip to his cockhead. Her blonde hair was tied back in a ponytail, and her she had on a cerulean cardigan over a thin tank top, as well as a matching blue skirt.

"Oh my god, Mrs. Cooper!" Jenny leaned back, keeping one hand on the shaft.

"Bob, what's going on?" Susan took one step forward.

"Oh goodness, Susan, um," Bob stumbled over his words, shifting uncomfortably in his seat. One hand reached up and ran through his dark hair as he sighed, realizing the jig was up. He might as well come clean. "Ladies, I'm sorry, but I've been, um, seeing both of you."

"What?" It was now Jenny's turn to be upset. Until now, she had just assumed that some old teacher had walked in on her blowing her boss. She didn't know that this teacher intended to do the same.

"I apologize, you're both just so incredible." Bob explained, trying his best not to hurt any feelings. In truth, he really did enjoy the company of both women equally. He was a principal in his late forties, he wasn't exactly being hounded after by many women. But suddenly two different women were showing interest in him, and he couldn't bring himself to turn either away. For weeks now, he'd been keeping the two women a secret from the other. Now, they were both furious.

"Principal Kelly, I can't believe this!" Jenny scolded him, her hand remaining on his still-hard cock. "You said I gave you the best blowjob you'd ever gotten; little did I know I was actively competing against someone else!"

"Wait," Susan paused, turning her attention to the young woman on her knees in front of her. "He said you were the best he'd ever had?"

"Oh, well—" Bob started, but Jenny cut him off.

"Yeah, he did. Why?" Jenny smirked confidently.

"Bob, you told me I was the best." Susan crossed her arms, which only made her cleavage even more prominent. As he ogled her soft breasts, Bob's cock twitched hard, which both women noticed.

"Oh my god, Principal Kelly!" Jenny exclaimed, upset, looking from Bob's cock, up to his face, following his eyeline to Susan's ample cleavage. "Well, which one of us is it? Who's better?" She demanded to know.

"Ladies, you can't expect me to pick between you. There's no fair way to judge—" He tried to speak again, but Jenny cut him off.

"Yes there is! Whichever one of us makes you cum first." The wild idea burst into her mind, and Jenny said it out loud before giving it a second thought. Susan's brow was knitted in thought, and Bob's mouth hung open as she continued. "We'll take turns. We get a minute per turn, and the first to make him cum wins." Jenny reached over to the desk, grabbing a small minute timer. Bob used it with students during conflict resolution; it ensured each student got their time to talk, and no one dominated the time. Now, it was being used for something very different.

"Um, I'm not so sure if that's the best idea, maybe—" Bob tried to speak again, but this time he was cut off by Susan.

"Fine." She nodded, dropping to her knees next to Jenny. "But I get to go first." Pushing her competition to the side, Susan slid between Bob's legs, taking a hold of his hard cock. It was firm and thick in her hand, still somewhat wet from Jenny's saliva. Her delicate fingers grasped his hefty shaft. Wasting no time, Susan parted her plush lips, taking in Bob's large cockhead. In the background, she could hear Jenny start the timer, and could hear it begin to tick away as she went to work.

Susan's lips were soft as she wrapped them around Bob's tip. One hand slowly stroked his shaft, and the mature woman felt a pearl of precum burst across her lips as she pulled back and planted kisses against the sensitive skin. Slowly, at a pace that made Bob ball up his fists and let out a soft groan, Mrs. Cooper took his cock back into her mouth. Working methodically, she sucked on the stiff member, running her tongue along it in her mouth. As she stroked him, he could feel the start of an orgasm forming.

DING!

The sound rang out through the quiet office, which had previously been filled with only the soft sound of Susan's mouth on Bob's cock.

"My turn!" Jenny said excitedly, pushing Susan to the side. Bob's cock slipped from Mrs. Cooper's warm mouth, and she pouted as she moved to the side. Jenny positioned herself back between Bob's knees, where she had been when Susan first walked in, and immediately dropped her head into his lap. As Susan started the timer again, Jenny began sucking on Bob's cock, much more ravenously than the previous woman.

Jenny was young, in her mid-twenties. Fresh out of college, she'd gotten this job as a secretary at the high school she used to attend as a teenager. Now, she swallowed her boss' cock down, pumping her mouth up and down quickly, spilling drool all over his cock as she went. She was thin and tan, having spent every spring break in a different southern beach town. Her small hands worked fast, stroking Bob's shaft with gusto. The fast pace was working on Bob, who could feel his balls churning as she spat on his cock, pumping her thin, pink lips back and forth, taking him further and further down with each push.

"Do you like this, Principal Kelly?" She asked in an over-the-top innocent voice that drove the man wild. Susan rolled her eyes.

DING!

Dejected, Jenny pulled back, allowing Susan to slide in again. As Jenny started the timer again, Susan took Bob back into her mouth, softly nursing on his rock hard cock. As she licked him up and down, slowly, with her velvety tongue, the principal couldn't help but let out a loud groan. The way this mature woman teased him drove him up the wall. Meanwhile, Jenny watched as Mrs. Cooper began to unbutton her blouse all the way, before tossing it onto the desk next to her.

"Hey, that's cheating!" Jenny cried out.

"Says who?" Susan pulled back from the principal's cock just long enough to retort.

Bob bit down on his knuckle as he got a good look at his employee's breasts, covered by a bra that matched her maroon glasses. Her breasts were large, barely held in by her silk bra, and they jiggled as she sucked on his cock. He'd seen them many times before, even tasted them in his mouth more than once. He'd never fucked them, no matter how badly he'd wanted to, because the ever-responsible Mrs. Cooper always said that whatever they did, she had to be composed enough to walk back to class afterwards; a sticky mess of her boss' cum on her chest may have made that difficult. Now, she leaned in close, pressing her bare body against his thighs. Bob felt her smooth skin, her soft tummy, and her plush tits brushing against him as she nursed on his cock. He also felt the orgasm building within him, stronger than ever before.

DING!

With a disappointed sigh, Susan shifted back, resetting the timer as Jenny centered herself before her boss.

"If you can do that," Jenny gestured to Susan's bra-covered bosom. "Then I can do this!" In a swift movement, the young woman dropped her cardigan, and peeled off her thin tank top, revealing herself to be wearing no bra at all. Bob groaned as he looked on at his secretary's bare breasts. They were smaller than Susan's, but they looked perkier.

Jenny leaned forward again, spitting directly onto his twitching cockhead, before guiding it into her hungry mouth. Without hesitation, she took him further and further down, inch by inch, deepthroating his thick cock until her nose pressed against his lap and his cockhead pressed against the back of her throat. For a moment, the room was silent, and Susan had to admit she was impressed with the young woman's talents. Bob could barely utter a breathless gasp as his cock throbbed in his secretary's wet throat. After a beat, Jenny gagged, pulling back, releasing the drool-covered cock from her mouth. Bob grunted in ecstasy in the chair, gripping the armrests with white knuckles as his secretary choked herself on his fat cock again and again, feeling it pulsate in her mouth, spilling precum down her throat.

"Oh my god, Jenny," Bob whimpered.

DING!

Susan pushed Jenny aside, and Bob's cock bobbed in the air momentarily after dropping from Jenny's mouth. She could tell that he was dangerously close, so the older woman stepped up her game. Taking his cock back into her mouth, she stroked with an increased rhythm, massaging his cockhead with her tongue. Her other hand reached up from her lap and found Bob's large balls, heavy with cum. He moaned when Susan began to softly massage them, rolling them in her thin fingers as she nursed on his cock.

"Oh, Susan, I'm so close," he murmured, his eyes closed tight. Determined to win, Susan released his cock from her mouth, instead dropping her mouth to his balls. They were so large she could only fit one in her mouth at a time, but as she stroked him with two hands, she kissed his balls with her soft lips, suckling on them, driving him ever closer.

DING!

The timer rang out, but Susan didn't budge. Instead, she continued sucking on Bob's balls, stroking the base of his cock.

"Hey, move!" Jenny said, annoyed. "It's my turn!"

"Not a chance!" Susan could barely speak with a mouthful of Bob's large balls.

"No fair! It's my turn!" Jenny refused to take no for an answer, instead pushing herself up next to Susan, the pair snug between Bob's legs. As the mature Susan nursed below, and stroked at the base of his cock, the young Jenny began sucking on his cockhead, jerking the top of his shaft.

"Wait, l-ladies!" Bob stammered. "I'm—I'm about to—" But it was too late. With a loud grunt and an involuntary thrust forward, Bob's cockhead pulled out of Jenny's mouth and his balls dropped from Susan's lips with a pop as he began to cum.

As the two women continued to stroke his shaft, one hand at the base, the other at the top, Bob launched rope after rope high into the air. Some shots streaked across Susan's face, and a few more splattered across Jenny's. He kept cumming, and a mess of white strands dangled between the two women's faces. Neither woman let up on their stroking, and the principal couldn't help but spill a mess of cum over their working hands as they stayed wrapped around his throbbing cock. Finally, he launched one final blast, which splattered across Susan's glasses.

"Oh, my heavens, Bob!" Mrs. Cooper gasped, sitting back, letting his cock go from her hand. "I've never seen you cum this much!" She removed her glasses, looking at the mess of cum showered across the lenses.

"Neither have I!" Jenny agreed, also releasing her boss' member. "Well, Principal Kelly..." She licked some of the mess from her lips. "Which one of us was better?"

Bob slumped back in his chair, entirely spent. He'd never cum so hard in his life. On their own, each woman was remarkable. But working together, they'd managed to drain him entirely. His cock, still hard, flopped against his stomach, and Bob panted as he looked at the two women kneeling between his legs, covered in his cum, expectantly waiting to hear from him. The lunch bell rang.