Back to School

The start of the school year was always crazy. It really started weeks before the kids came back to school. In fact, Kelly designated the month of August as school prep. She tried not to think about it at all for the month of July, giving herself a mental vacation from work, but as soon as August began, she was in prep mode. There were fresh charts to be made, welcome letters to be written and printed, a seating chart organized, all kinds of personalized signs and nametags made for her class of 28 third graders, color-coordinated baskets and folders to be prepared. And all of that was on top of her summer job as an art specialist at an overnight camp. She wasn't even home to do all of these things, and yet somehow, she found time to craft cute book basket signs in the back room of the art shack in her off-hours.

By the time she walked through the doors of the school building on the day teachers were allowed to come in to set up their classrooms, she carried several large totes full of materials she had bought and made. It was Kelly's 6th year teaching, she wasn't exactly a newbie. She had a good idea of how she wanted her room to look, what had worked last year and what she wanted to change. There was a definite confidence in her step as she moved through her room, pulling the single desks into groups.

"How was your summer, sweetie?" Maryann walked into her room, heading right towards her with her arms open. Kelly stopped what she was doing, turning to hug the teacher who had just walked in.

"You know, not long enough, as always," she made a gesture with her hand. It was the same phrase they all repeated to each other upon return from summer vacation.

"As always, so true," Maryann agreed, leaning against one of the desks. "Did you do anything special?"

"I worked at camp most of the summer, like always. It's fun, I definitely enjoy it, but it's not exactly something special. I've been going to camp since I was ten." Kelly continued moving the desks into places as she talked.

"Awe, did you take a break at all? Go away anywhere, besides camp? You know, actually stop working for a few days?"

"Mmm, yeah. Caroline and I went to one of those all-inclusive resorts, right as school let out, back in June," Maryann smiled with interest. "It was geared towards singles with all kinds of activities and events. It's almost like camp for adults, come to think of it," she laughed to herself. "But yeah, that was a good time. Drinking, soaking in the pool, dancing, it was definitely a good time."

"And did you meet anyone there? Since it was for singles?" Maryann's expression was suggestive, her eyebrow wiggled.

"Well, you know," Kelly felt her face flush, "yes, but," she waved a hand. "It was just a little fling. Not anything more serious."

"Ooh, tell me, tell me! Let the old girl live vicariously through you!" Maryann looked giddy. Kelly laughed, picking up a chair off the stack and bringing it to the desk. Maryann stood up to help her.

"You are very far from old!" She shrugged her shoulders. "I'm not sure what to tell you. There was this guy, we kinda hit it off, he's a teacher too. We hung out the few days that we were there. We've texted a few times back and forth after that, but honestly, I was just too busy and wrapped up in the summer job and the school prep to really follow through on anything,"

"Just hung out? Is that like... sat next to each other in front of the pool or more like... rolled around in the sheets?" Kelly didn't want to look at Maryann as she continued to place chairs at their respective desks. This was embarrassing. Scenes from those three incredibly hot nights with Justin flashed through her head like a movie montage. Actions sped up and slowed as images of his hard, naked body flitted in front of her eyes.

"The latter, I suppose," Kelly replied quietly, feeling her face burning.

"God, I can only imagine. Hank and I got married basically right out of college. We've gone to some couples resorts back when we were newlyweds, before we had the kids, but I bet that's totally different. It must have been so much tasty eye candy, just hanging out by the pool too." Maryann was wiggling her eyebrows again when Kelly looked over at her. She had to chuckle.

"Yeah, I guess. It's actually rather intimidating. Because it's not just a ton of hot guys out there, it's also all these tall and thin, gorgeous women in thong bikinis with hair that just falls perfectly down their shoulders," Kelly did not consider herself one of them.

"Oh come on, sweetheart, you've got a hot little body," Kelly blushed again, this time at Maryann's compliment. She didn't consider herself unattractive, but the word mostly aptly used to describe her was cute, rather than hot or gorgeous. She had a decent set of breasts and an ass that allowed for something to grab onto, but she had plenty of insecurities too. The freckles that covered most of her face, chest, and arms were definitely big on that list, as was her frizzy hair which could never seem to decide whether it wanted to be curly or straight and was perpetually somewhere in between, in an out of control mop.

Her insecurities were part of the reason why she tried not to get too hung up on this Justin guy she met. She replied to his text messages, but tried her best to be cool and not get too attached to him. She didn't pick up the couple of times he tried to call her. She convinced herself that it was best not to get her hopes up with a guy like him. He was out of her league and the only reason things worked between them was that it was a temporary fling, just a hookup, where they didn't have to worry about the long term. Justin was handsome and confident, with these super strong arms and shoulders, the deep, sexy dimples that popped when he smiled, the crazy blue eyes that locked in her gaze. And the things they did together... these were not things that Kelly was used to doing with her boyfriends. His confidence transformed into something so sexy and commanding when it came to sex, that Kelly was compelled to join in his game and stretch her own comfort zone.

"What did you do over the summer?" Kelly asked Maryann, changing the topic. She felt a lot more at ease listening to the veteran teacher describe the family vacation to Maine that she took with her husband and their three nearly-grown children. Her youngest, a 14-year-old, had spent the majority of his summer at camp and the 18 and 20-year-olds had summer jobs, so she had the house mostly to herself throughout the day, she said.

Maryann didn't bring up any more questions about the man from the resort and Kelly didn't volunteer any information. She was grateful for her help with the chairs but glad to see her finally go so that she could focus on her classroom setup. There were curtains to hang up, book baskets to arrange, nameplates to attach to desks, and a dozen other things that she needed to do before the first official day for teacher in-service arrived.

The first compulsory days for the staff were always filled with meetings, planning, and professional development sessions with little time to get more done in the classroom. Kelly was there bright and early at 7 am to put up borders and titles on her bulletin boards before the faculty meeting at 8:15 am.

"Heya bestie!" Caroline stopped in her doorway holding a notebook and pen. "Ready to go?"

"God, is it time already?" Kelly groaned. She got her own notebook and pen, to take notes during the meeting, and joined her friend who immediately linked their arms together as they walked down the hall and towards the stairs.

She and Caroline had started at the school together, right out of college. They didn't know each other beforehand, but ended up navigating the perils of their first year of teaching together and became super close. They applied to and completed their Master's programs together, put together their tenure portfolios together, and have genuinely become each other's closest friends. The trip to the singles resort that they took that June wasn't their first vacation together, but it was definitely the most indulgent one they took. They were celebrating - their graduate degrees were complete, their tenure had been granted, and they had received their professional teaching certificates to replace the initial ones that they had begun with. That was a lot of work under their belts, in addition to everything that teaching full-time entailed.

They settled themselves in the auditorium, about halfway down to the stage. Kelly worked at a relatively large school; it spanned the grades from Pre-K through grade 8 and there were over a thousand students. So the staff was fairly large as well. People filed into the auditorium, picking up folders with the beginning of the year materials on the way in and sitting down with their friends or with their grade teams. There was a din of conversation as people gathered and when the principal, Mrs. Eringale, stepped up to the podium to get everyone's attention, it took a few moments for the auditorium to quiet down.

She welcomed everyone back, then talked a bit about her summer and her excitement for the upcoming school year. She moved on to congratulate a few of the staff members on their engagements, weddings, and newly born babies before she got around to welcome some of the new staff.

"We've had a bit of a last-minute shakeup in our administrative team, just in the last couple of weeks, that caused me some nail-biting anxiety as Mrs. Boldt, our middle school assistant principal, received an offer to take on the principal role at a school in Marine Park and she accepted it." Her announcement was followed by applause from the staff. "So we had a bit of a scramble to fill the role, finding just the right fit among available candidates, and I think we've been matched up pretty well," she smiled at someone sitting in the front row in front of her. "I'd like to introduce you to our new middle school assistant principal, Mr. Miller," she gestured with her hand towards the front row and the man stood up, turning around with a wave and a smile to the audience, deep dimples popping on both sides of his face, making Kelly's breath catch. "Mr. Miller is joining us after over a decade of teaching Social Studies at a junior high school on the Lower East Side in Manhattan. He coached a Debate Team there, as well as the Council for Unity, and comes very highly recommended by his former administration who were incredibly sad to see him go." Justin chuckled, placing one hand inside his suit pants pocket.

He looked so comfortable with himself, so casual and handsome and effortless and Kelly may have forgotten to breathe until Caroline's hand was grasping her forearm tightly and she was mouthing to her "Oh. My. God!" Kelly felt herself slink down further into her uncomfortable auditorium seat. He was here. He was standing right there in all his dimpled glory and she was going to have to see him and interact with him in one way or another this year. After all the dirty, filthy things she and Justin did for those three nights back in June.

****

He watched her from across the pool, sitting out on a lounge with her e-reader wearing a nearly sheer, loose, white tank top over her bikini. Her red hair was piled high up on her head and she seemed totally absorbed in what she was reading. So much so, she seemed to have no clue that he had been staring at her. He noticed her because she was different. She was very much unlike all the other women around them. She had this fresh, young, 'I'm not even trying' look. The woman next to her has been adjusting and readjusting the fabric of her bikini over her breasts, the one a few lounges over has been slowly and seductively applying sunscreen to her legs for the past twenty minutes, and the woman sitting right next to him had so much makeup on that he was quite curious what would happen if she went into the pool with it all.

He made a move when the woman on her left stood up, walking away.

"You must be reading something incredibly interesting because you seem entirely absorbed in it," he smiled at her, sitting down on the edge of the vacated lounge.

"Yeah," she smiled back, squinting at him against the sun.

"What are you reading?" Justin tipped his head to the side.

"The Hole, by Guy Burt," she told him. "It's a psychological thriller."

"Ah, I would have assumed something entirely different by its title alone," he admitted. She blushed furiously.

"No, no, I'm not reading erotica out by the pool."

"You only read that in private?" He winked at her, trying to be playful.

"Yep," she confirmed, her complexion still crimson. He had to chuckle at that. He loved the fact that she rolled with his accusation instead of getting offended and trying to fight it.

They talked about books, then about teaching, when it turned out that she was in the same profession, then about places to eat in New York City, when it turned out that they were both living and working there. She was in South Brooklyn and he was in Lower Manhattan, but they've found a few common places that they both enjoyed. It was easy talking to her. Kelly was funny and droll and it felt like they really hit it off right away. She looked entirely shocked though when he asked her to have dinner with him that night.

"Do you have other plans?" He furrowed his brow.

"No," she shook her head, biting her lip. "I mean... I'm here with a friend, Caroline, but I..." she seemed to stammer, blushing again. "I can have dinner with you, yeah, that's fine."

"I thought we had a bit of a connection, you know," he gestured with his hand between them, "I thought we could roll with it, explore it more." Her eyes scanned his face as if she was looking for him to confess that he was just kidding, that it was a joke. "I'm serious," he added.

"Yeah, ok," she nodded. She drew her lips in, pressing them together.

She seemed to spruce up a bit for dinner, some makeup, her hair blown out and falling over her shoulder in a smooth curtain, a pretty floral dress that showed off her figure. Of course, she was beautiful this way too, but he had an incredible urge to mess up her hair.

He took the date pretty seriously, more so than he would have with most other women there. To begin with, he liked her, he felt like he could talk to her, there was substance there. But in addition to that, she was also from the city so this could potentially evolve into something more than just a hookup at a resort. They were both teachers, there was geographic proximity, and Justin felt like at this point in his life he wouldn't mind something less transitional and more long-term. He was thirty-five, not exactly a kid who was interested in a revolving parade of random women anymore.

After dinner, drinks, and that evening's show which featured a comedian, he decided to make a move. He wanted more time with her.

"What would you say to getting a bottle of wine to go and heading up to my room?" Justin didn't beat around the bush. His fingers laced through Kelly's and he knew she was blushing again, even in the dim light of the lounge. She seemed to give his preposition a bit of thought before she nodded.

"Yeah, let's do that," she finally agreed.

Yes, he was there with some friends too, but they were smart enough to each have their own room for just this sort of eventuality. He poured wine into two glasses, handing one to Kelly, and made a toast to having a good time with her. She had gorgeous green eyes that smiled as she sipped her wine. There was some small talk about the wine and the view out of his floor-to-ceiling windows before he took the glass out of her hand, set it down on the dresser, and pulled her in for a kiss. It was intoxicating, deep, and luxurious. He wanted more. Their lips and tongues moved together as he walked Kelly backward towards the bed.

The backs of her legs hit the edge of the bed and she sat down involuntarily. He stopped for a moment, standing over her, wanting so many things to happen right then, but opted for unbuttoning his shirt while Kelly watched him.

"You know what would be super?" He leaned down to cup her face in his hands and kissed her again. She moaned against his lips. "If you took your dress off," he finished.

She pulled her feet out of her slip-on sandals and sat up on her knees on the bed. Then in one swift move, she pulled her dress up over her head, tossing it aside. She had on a lace, magenta bra that displayed her full breasts perfectly, forming an enticing cleavage in the center. She seemed to be waiting for him, still kneeling on the bed. He noted that to himself, the way that she responded to his request and the way she was sitting now in anticipation.

"That's gorgeous," he told her, scanning over her body, taking all of her in, then he worked on undoing his jeans and stepping out of them.

He leaned down to kiss her again, standing in front of the bed, and she reached her arms up to wrap around his neck, sitting up on her knees. He ran his fingers down her sides, over the naked skin between the bra and the panties. He traced the path a few times before reaching behind her and unclasping the bra. He pulled back, tossing the bra aside and checking out her breasts. His hands instinctively came up to cup them, feeling the weight of them, stroking his thumbs over her nipples. She looked down, watching his hands on her breasts. One of her hands came down slyly to rub his cock over his boxer briefs.

"Why don't you take it out for me," he watched her reaction at his suggestion. She didn't look up when she slipped her hand inside, pushing his underwear down in the front and releasing his cock. She stroked the length a few times before looking up at his face. Her eyes wide and innocent as if she were looking for the next direction from him. "I'm enjoying what you're doing, keep stroking my cock, sweetheart," he tested his theory. There was the briefest smile that slid over the corner of her mouth before she tucked it away. Oh hot damn! He felt his cock twitch in her hand at the thought. It appeared that Kelly might be up for some play.

Justin pushed his boxer briefs all the way off, stepping out of them. Her hand disconnected for a moment but was right back on him as soon as he stepped closer to her. He watched her for a moment from above, forming new ideas in his head as to where he was going to take it.

"I think I want you on all fours on the bed now," he told her. She looked up at his face, a flicker of uncertainty sliding over her expression. "Don't worry, I'm not gonna fuck you, yet." She seemed ok with that reply and moved into position. He came up onto the bed next to her, sitting up on his knees and reaching between her legs. "Spread them open wider," he instructed. Kelly complied. He rubbed her pussy over her panties, pressing his fingers against the fabric. They were already damp and he could feel them become distinctly wetter as his fingers worked her slit. "Look at that, you've wet right through your panties. We are gonna have to pull them down now," he worked them down over her hips, but left them at her thighs, without taking them off completely.

She seemed to push her ass back, her back moving into a downward arch. He returned his fingers to her wet folds, sliding them to her clit, circling around it, and then returning back through towards her pussy. He pressed two fingers inside and she moaned at that, throwing her head back. "Oh you like that, don't you sweetheart?" He played with her. His fingers found a rhythm, thrusting in and out, while Kelly seemed to push back towards them, meeting his thrusts with her own. "Mmm, see, I don't know why you gave me that look before. It definitely looks like you want to get fucked." She only whimpered in response. "Do you like to be told what to do, Kelly?" He wanted to confirm his suspicion before he took it any further, even though he'd be surprised at this point if she replied with a 'no.'