Pegging - a sexual practice in which a woman penetrates a man's anus with a strap-on dildo - from Wikipedia.
Shannon McDaniel knew having a crush on her boss was wrong, but it felt so good. Mr. Carroll understood how it felt to be nineteen and full of needs. Did it matter if he was forty something? He listened without judging, never treated her like a kid, and understood "good girls" had naughty needs, too. After months of working together, she learned she could ask him anything and he would answer her openly, honestly, and with a candor other adults never used.
Her first questions were lightweight, barely offensive. "Do you think it's slutty when a girl goes without a bra?" He told her guys always noticed, but caught the other part of her question and called her on it. Giggling, she admitted it. "Yeah, I do feel slutty when I don't wear a bra and I sort of like it."
Later, she would ask more direct questions and enjoying how careful Mr. Carroll was with his answers. When she asked, "How often do guys really masturbate?" He qualified his answer by saying, "When I was nineteen..." and finished by admitting, "Almost every day."
She wasn't sure when she started flirted with him. She wasn't sure if he noticed, either. But her questions became more intimate, more suggestive, and sometimes, they weren't questions at all. Sometimes, she would tell him about her latest date, as if he was a confidant. "Ace is so pretty, but he has such a small dick," she reported about a recent boyfriend who didn't make the grade. Mr. C teased her, calling her a [i]size queen.[/i] She defended her reputation. "No, I don't like big ones, but his was really small."
She asked if he thought a man could be satisfied with a blow job only relationship. "Not forever," he said, looking as if he had a reason for saying that. When she pressed, he changed the subject. Another night, she asked if he ever went [i]commando[/i] and he admitted, "When I wear jeans." She said he should wear jeans more often and later wondered if he avoided jeans when he worked with her. For an older guy, he was well built and had a good fashion sense. Slim, with broad shoulders and a tight ass, she liked the idea that maybe, beneath his jeans, he was naked.
After a month of him wearing khakis to work, he finally showed up in jeans. Was he doing it on purpose? Did he remember her question and his answer? Thinking backwards, she realized he usually wore khakis to work. Had it taken a month for him to forget her question or a sign that he wasn't afraid to tease her? She couldn't stop thinking about his going commando answer. His jeans were tight, too. What if he got excited? Without the barrier of underwear, would it show?
Shannon wondered if she could get him excited. While Mr. C always treated her as an adult, was that how he saw her? At nineteen, Shannon didn't feel like a girl anymore, but Mr. Carroll was more than twice her age. Would that matter to him? Getting her answer was as simple as it was direct. "Do you still notice girls my age?" she asked.
"Notice how?" he asked with an amused grin. He knew what she meant, he always did. She shot him a sardonic look and he laughed. "I'm old, not blind. It's not about noticing hot nineteen year olds, it's believing they would ever want to notice me."
"I think you're hot," Shannon said. She meant it as a nicety, a bit of reassurance, but it felt like a confession. She felt her face heat up and she turned to adjust a clothing rack so he wouldn't see.
"Thank you," he said. "And for the record, I'm flattered, but I don't believe you."
As open as Mr. C was with her, he never crossed the professional barrier that separated them. He was her boss, something he took seriously. He could be friendly, but as he had explained it, they could never be friends. Not real friends. It wouldn't be right and that made the idea even more attractive to her. He felt like forbidden fruit to her. Could she get him to cross that line? Feeling her blush fading, she faced him. "You know when I say 'hot,' I mean in a sexy way, right?"
Mr. C nodded. Looking uncomfortable, he told her, "I think you're hot, too."
Shannon accepted his compliment and took it as a small victory. It was seven thirty at night and the store was dead. It was just the two of them and from the way traffic had been, it might stay that way for the rest of the night. Company policy required two people on staff at all times. Mr. C said it was for two reasons: safety and theft prevention. They worked the closing shift together once a week. With a week before Daylight Savings Time kicked in, the parking lot was dark and empty, giving the store an intimate, private feeling. "Do I ever get to you?" Shannon asked, pushing.
"I try not to think about it. You work for me, so there's a line there, you know?"
"Ever cross that line?" she asked. When he looked away, looking embarrassed, she knew he had. "I want details! Dirty, nasty, explicit details." Mr. Carroll laughed, tried to brush her off, but she insisted. "Come on, I tell you about my sex life all the time, can't you tell me just one story?" She cajoled him into it with a hurt pout. "Come on, don't you trust me?"
His story lacked nasty or explicit details, but he told the story of a woman who worked for him several years ago, Margo, who loved giving oral sex. Shannon pressed for details until he admitted it had happened in the store, that Margo had pushed herself on him, and it had gone on for several months before she decided to go back to school to finish her degree.
"Just blow jobs?" Shannon asked, unafraid to use adult language in front of him. That was a barrier she had crossed months ago.
"She had a live-in boyfriend and I had a live-in girlfriend, so it was awkward," he admitted with a nervous chuckle as he fiddled with a pen on the counter, nervously spinning it. Shannon kept stealing glances at the front of his pants, noticing a pleasant looking lump running down his leg. Was Margo who he meant when he said a relationship based on oral sex wouldn't last?
"Well, for the record, I'd rather peg you than blow you," she said, heading towards the backroom. She needed to pee.
"What's that mean?" he asked.
"Do a Google search for 'pegging,'" she told him. "You might like the idea." Inside the store's bathroom, Shannon shook her hands and jumped up and down a couple of times. Pegging was her secret fetish, a game she played with her boyfriends. Before they ever fucked her, she wanted to fuck them. Some let her, some didn't. The ones who did got to keep dating her. The ones who wouldn't found themselves blocked from her phone. She splashed a little water on her face, trying to cool herself down before she went back out front. What would Mr. C's reaction be to her favorite game? Standing at the backroom door, she took a deep breath before walking back out front.
"You really do this?" he asked, jabbing at his phone the moment he saw her. She noticed two things. First, he had been watching a video. Second, with his lack of underwear, she saw the lump in his pants had grown. Instead of extending down his leg, his bulge ran perpendicular to his zipper. His cock looked longer and fatter. She felt her nipples go stiff as she tingled down below and wondered how hard she could make him.
Pasting a smile on her face, she nodded. Moving next to him, she poked a few times at his phone, bringing up a favorite video of hers. The guy on his hands and knees was cute and she liked the way his cock throbbed. The woman wearing the strap-on was pretty and having fun. She held the phone for him to see. "It's hot as hell, isn't it?" Her eyes looked past the phone at the bulge in his jeans. Was it her imagination or was his cock getting bigger? "Ever take it up the ass, Mr. C?"
"Not from a woman," he mumbled, looking embarrassed. "Or a man," he quickly added, blushing. Stopping the video, he put his phone away. "Sort of gay, isn't it?"
Shannon laughed. "What's gay about having sex with a beautiful woman?"
"Getting it up the ass." He laughed, too, but it was a different kind of laugh for him. More of a nervous chuckle than his usual belly laugh. He started playing with the pen on the counter again, watching it spin.
Shannon watched him for a moment, thinking about his reaction. She caught herself staring at the lump inside his jeans. Linking his answers together left her with just one realization. The idea surprised and teased her. Could it be true? "You like it up the ass, don't you?"
"I never said that," he said, keeping his head down.
"You never said your ass was a virgin, either. You're more concerned about ass play being gay."
"Why do you say that?"'
"Dude," she said, addressing him informally for the first time. "Did you see that video? I like doing that. I won't date a guy who won't let me peg him and I've heard all the excuses." She dropped her voice into a lower registry, mocking the guys she had ultimately pegged. "It's an exit, not an entrance." And, "That's too gay." She laughed. "I've heard it all. But they all like it."
He gave her an amazed look. "You're a remarkable woman, Miss McDaniel," he said, shaking his head in disbelief. He squirmed, looking uncomfortable. Was she getting to him?
Shannon's heart was racing. Every fiber of her body felt alert, alive, and at attention. Her nipples were twin pebbles against the inside of her bra. Her pussy ached with need. Could it be that Mr. C had a secret fantasy? Softer, careful to sound casual and playful, she asked, "So do you use a toy back there or just fingers?"
"Shannon!" he said, acting shocked.
"Aw, come on Mr. C. It's just a question. I won't tell anyone."
He squirmed again as he went back to watching the pen spin on the counter. "I plead the fifth," he said, but she caught him watching her out of the corner of his eye as if measuring her reaction.
Shannon smiled. If he was trying to get to her, it was working. But what if he was telling the truth? What if he did like to put things up his ass? Was it possible that she could peg her boss? The idea tugged at her alert and alive libido. "You're a naughty man," she teased, drawing closer to him. With her hands on his shoulder, she leaned close and whispered in his ear, "I keep my toy in my car."
"Why would you do that?" he asked, surprised.
"Nosy roommate and, you know, just in case I meet someone fun." She noticed the bulge inside his jeans was longer and moving more upright. She felt giddy and lightheaded. "Are you a mushroom, Mr. C?"
"You know, a fungi?" she said, pronouncing the pun as "fun-guy." He laughed. She pulled away, pacing herself. "So really, tell me. What have you put up your backdoor?"
"You're not going to let it go, are you?" When she shook her head, he muttered, "This is so wrong."
"You know you want to tell me. It's fun sharing secrets." It was a force of will not staring at his crotch. "I know, I share all of mine with you. You can share this one with me."
"I already told you a secret."
"No, that was a story, this is a secret. Come on, give me a thrill."
Mr. C bit his lip, looking as if he was fighting a battle of wills against himself. A battle he lost. " I might own a toy, but what I do with it is none of your business," he said and then looked away as he face turned red.
"Do you have any idea how wet that makes me?" she confessed.
"Yeah, well..." he started, stopped to reconsidered, and finished with, "We should probably talk about other things." Shannon was sure he nearly admitted to being excited, too.
"I'd rather think about bending you over your desk."
He asked if she really pegged boys (his word) or was she just playing. Once she convinced him she really did, he asked, "Does it do anything for you?" He moved to the other side of the counter. Shannon caught the way he adjusted himself when he turned away.
It was fair question, one she had heard before, but she spun her answer. "Let me do it and find out."
She bit back saying, "Me too!" for the truthful answer. "Oh, it rubs against me just fine," she reported. "But the real thrill is seeing a man with his ass up in the air." She giggled. "That's sexy as hell."
"An act of trust for him, that's for sure," he said, avoiding her gaze by glancing at his watch. "Getting close to closing time. Think it's too soon for me to countdown the register?"
"Probably not," she said, frustrated that he changed the topic so easily. She glanced at the time, surprised to see how much time they had killed. In less than ten minutes, they would lock the front doors, turn off the lights, and head their separate ways. It bothered her the way it felt as if an opportunity was slipping away. It started as a game to see if she could get him hard and if it would show because of his clothing. She never considered how excited she would get. Her body buzzed with an aching need for release. Worse, she was sure he wanted to be pegged, but was it something she wanted to do to him? Men are often accused of thinking with their little head, but Shannon knew women could make the same mistake. She felt the unquenched desire to see how far she could take things. Would he let her touch him? And if he did, what then?
"Remember that story you told me earlier, about that Margo chick?" Busy counting pennies, he nodded. "Do you think anything would have happened if she hadn't thrown herself at you?"
He shook his head, pausing before continuing his count. "Probably not. A little known fact of sexual harassment laws, they only apply from the top down."
"What's that mean?" She waited until he finished his counting the nickels for her answer.
"I can harass you, but legally, it's impossible for you to harass me because I can always fire you for being inappropriate at work." He made a note of his count with the pen he spent so much time spinning and picked up a handful of dimes.
Shannon giggled. She couldn't believe Mr. C would fire her. He might reject her. He might tell her to stop, but fire her? It wouldn't happen. She could own his ass, literally. Feeling drunk with possibilities, she slipped behind him. "So, if I do this, you can't get in trouble?" She grabbed his ass, massaging it. Stuck in the middle of counting coins, he didn't react until he finished his count. When he did, he squirmed out of her grasp.
"Not me," he warned, jotting down his count. But his threat was a paper tiger. He didn't tell her to not to do it or to stop doing it. How much more could she do?
"I didn't even mess up your counting," she said, a giddy giggle escaping from her.
"Can't you find something else to do?"
Again, he didn't dismiss her. "This is more fun," she said, waiting until he started counting the quarters before she moved. She started with her hands on his hips, hesitating before doing anything more. He dropped the quarters back into the tray, either loosing count or giving up.
"I'm trying to count" he said, looking over his shoulder.
"I'm not stopping you," she giggled.
"You're not helping, either."
"Go for it, let's see how good you are at counting."
"Okay," she said, waiting for him start counting again. How far could she push this? When he resumed counting, she moved her hands around him, rubbing the bulge that had been teasing her so much. He dropped the quarters a second time and she giggled in his ear.
"Stop it," he said, but he didn't wiggle away. Nor did he try to brush away her hand, still rubbing the bulge in his pants.
"Go ahead, keep counting." His cock was a long, tube-shaped piece of needful stone inside the cotton of his jeans. If he started counting again, she knew she had him.
"Even if this is just a tease, you realize I have nothing to lose," he said, standing still.
"Then tell me you want it."
"Then tell me to stop again and I will." Shannon wasn't sure she would, but maybe.
Mr. C's picked up the quarters. Pressing her breasts against his back, she felt his warmth as she raked her hard nipples against him. A man doesn't get this hard unless he's in need and being in need was a sensation she understood. She wanted this man, this real man. She wanted his hard cock in her hand; his bare, hard cock. She wanted his ass. Would he push back against her toy? Would he moan and beg to be fucked deeper and harder? Or would he stop her before it went any farther.
She pressed her finger between the crack of his ass, following the seam of his tight jeans. From the way his cock jumped again, she knew her aim was true. Again he dropped the coins. "Shannon, please," he moaned.
"Keep counting, " she said, wiggling her finger against his asshole. When he returned to counting, she smiled. Where was his limit? Did he had given up on having one? She worked the button of his jeans, tugging them open, and heard him gasp before her hand reached inside the open fabric. The game changed when she wrapped her hand around his hard shaft. The flirting and teasing ended. Had she crossed a series of smaller lines or pressed across a wider, blurry line? She could stop, but couldn't think why she should. His hard prick felt so good inside her hand. His compliance fed her ego. If he didn't stop her, then he must want this, all of this. "Mr. C, you've been holding out on me. You're hung!"
Rhythmically, quarters dropped into the coin tray while his cock throbbed in her hand, pulsing with the rhythm of his excitement. As if ignoring her caress, he leaned over, made a note of his count, and picked up a large stack of one dollar bills. Did he think she would stop if he ignored her? His compliance was an invitation. Wetting a finger, she slipped her left hand inside the back of his pants, her wrist pushing his jeans farther down as she reached for her prize. Pressing her wet finger against his puckered asshole, she pushed her finger inside of him, and thrilled at the warm sensation of his butthole squeezing around her digit. "Tell me I can have this."
He gasped, holding a fistful of singles. "I can't." He tried to restart his count.
"Tell me to stop or I'll take what I want." She pushed her finger deeper in his ass while her other hand explored his front, touching his cock and his balls already pulled tight with need. She felt his hard cock throbbing against her wrist. When he didn't answer, she told him, "Take off your shoes."
"Do it," she said, jamming her finger deeper inside of him. Toe to heel, he worked his feet from his shoes. She brushed his jeans down his legs. Tapping the back of his knees, he lifted his feet free from the puddle of fabric around his ankles.
"The front door is unlocked," he said reminded her before picking up the count again.
"Count faster." She gave his bare ass a squeeze before she walking to the front of the store and turned the lock. Turning back, she walked slower, watching him counting. He glanced up at her, lips moving as he counted to himself. From the other side of the counter, nothing looked amiss. Should someone walk past the front of the store, they would see Mr. C counting a drawer and never guess he was naked from the waist down. She picked up his jeans and shoes, smiling at his designer socks. Mr. C had style, she liked that. With his clothes in her hand, she moved towards the backroom door.
"Where are you going?" he asked, concern in his voice for the first time.
"To get my toy," she said and pushed through the door. She stashed his jeans and shoes on a shelf near the backdoor. Outside, the early spring air was brisk in her lungs. She saw the exodus of workers from other stores already in their cars and heading home. On the floor behind the driver's seat sat a pink gym bag with a logo for a local gym. At the bottom of the bag was her strap-on, covered with a set of work-out clothes and a pair of sweats. Believing no one would dig around inside a gym bag, Shannon kept it with her to hide the toy from her snooping roommate. She snagged the bag, feeling the same rush she felt carrying it inside her boyfriend's apartment. She walked back inside the store in time to see her half naked manager darting into the backroom, his swollen cock leading the way.