Caught At School

We finalized the pizza topping order and they left. The building was so quiet that I heard the outside door close behind them. Even the maintenance crew must have been taking it easy tonight. It was December, so it was already getting dark outside. I blasted through the stack of tests ahead of schedule and only had two left when I heard the click-clack of footsteps in the hallway and another knock on my door.

"Mr. Stator?"

"Susan, I said I'd be done-" I stopped there, because I looked up and it wasn't Susan. It was Barbara Whitlock.

She stood at the doorway, perhaps a little confused.

"Oh, I...sorry. I thought you were someone else."

"Did I come at a bad time?" Barbara Whitlock asked. She wore black yoga pants with some kind of design that revealed strands of her legs, and a skin tight maroon top, hair tied back into a ponytail, which made her look younger than before. Her winter coat was open and I could see that her nipples were hard. They weren't huge tits, but a good size. Maybe C-cups. Even though she wore workout clothes, her makeup was done up. Including the bright lipstick.

"No!" I said, perhaps a little too enthusiastically. "Not at all. I mean... I was just grading some tests."

"I thought maybe I could talk to you."

"Sure, of course." I shuffled some papers around just to look official. "What about?"

"I thought maybe we could work something out."

"Come in, sit down," I said, even though there wasn't really anywhere to sit other than the students' desks.

Barbara kicked the door stop and let my door close with a hissand a clunk.

I stood, came around the front of my desk, and half-sat on the edge. Barbara came up close. Close enough for me to smell her sweet perfume and see the slightest wrinkles near her dimples.

"What's going on?"

"It's Bradley. We're just not able to get him focused."

"These things take time. Patience. Consistency." I was feeling a little flushed.

"May I?" she asked and removed her coat. She leaned over and placed it on my desk.

I tried to keep my eyes up, but I couldn't help it. I admired her body for a few seconds. I wanted to see what those C-cups felt like through the stretchy fabric of her shirt. She had nice legs. Short, but nice and curvy.

I thought she'd move a step back, but she stayed close. When I was able to refocus, I said, "Bradley just needs a little discipline. I think. And maybe a little less time in sports and more time studying. Does he read books at home?"

Barbara shook her head, her ponytail swung back and forth playfully. "Never."

"It's important. Even reading fun stuff is beneficial for-"

"You know, I think I would've done better in school if I had a teacher like you," she said and leaned close to my ear and whispered. "A tall, handsome man like you."

"I... uh..." Suddenly the room felt very hot to me. This was no fantasy daydream. This woman was coming on to me, hard. "Thank you." She stayed close to me for a second and I slipped a look down her shirt. It was athletic clothing, but I could see the bit of cleavage she had displayed for me.

Barbara placed a hand on my thigh. I almost flinched, not really expecting it. I knew I should move away. I knew Alonzo from the cleaning crew could come in here at any moment. But I didn't move a muscle.

"Look, you were asking about private tutoring before. And I don't have a lot of spare time, but I could help out a little. And I could definitely recommend someone. There are a lot of very qualified tutors in this district. In some cases, drastic changes can be achieved."

Barbara smiled, removed her hand from my leg, and blinked those brown eyes.

I moved so that I was sitting on my desk, hands perched next to me.

She swiveled and stood in front of me, between my legs. With the height of my desk, we were now eye to eye. She moved closer. Then closer, until her face was only inches away and I could feel her breath when she spoke. "I had something else in mind." She put both hands on my thighs and rubbed them while she stared into my eyes.

Khaki pants are notoriously horrible at hiding erections. And I was quickly growing one. Barbara moved her hand over it and gave my bulge the gentlest stroke of her palm.

"Oh?"

"Yeah, I was thinking..." She used both hands then. I could feel my face flush and my dick harden. "You could just..." Barbara squeezed my shaft. "Fix it."

"What?" I'm not an idiot. I don't know why, but that was not what I was expecting. Somehow, I thought this milf just wanted to fuck me. Not bribe me.

"I can tell you're interested," she said, and traced my shaft with her fingers all the way down, then cupped my balls through the fabric. Barbara put her lips right next to my ear. "I'll give you the suck of a lifetime until you blow your load."

I quivered a little at the thought of those red lips sliding up and down my cock.

Barbara pulled back and winked again. "I'll even swallow it."

"I..."

She continued, "All you have to do is change a few numbers in your little grade book."

I shoved off of my desk, but I didn't want to stand there with a boner tenting my khakis, so I sat down. "I think you should leave."

Barbara looked surprised.

Hell, I was surprised. "It's tempting," I said. "Believe me, it's tempting. But I can't. I just can't do it."

She followed me to the chair and stood above me while I sat. "What do you want, then?" Barbara crossed her arms and tapped a polished fingernail on her cheek, pretending to mull it over. "You want to fuck me? You want to bend me over this desk and get sweaty?"

"I want Bradley to do his work," I said, weakly. "He can do it, you know."

Barbara ran her hands along her body up to her breasts and squeezed them together. She pinched her nipples and smiled. "I'll let you cum on these if you want."

This did nothing to abate my boner.

My classroom door opened. "Hey Alex, can you..."

I craned my neck around Barbara.

It was Olivia. Fuck. She had stopped mid-sentence and stood there holding a stack of papers. Her mouth dropped open.

From her angle at the door, it could've looked like anything. Mrs. Whitlock bent over me at my desk. It might've looked like we were kissing, or about to. Whatever it looked like, it didn't look good.

Olivia's face hardened. I couldn't tell if she was upset or disappointed. She turned and quickly withdrew without words.

"Oh, shit," I said.

Mrs. Whitlock picked up her coat and put it on. "Relax, we weren't doing anything. Yet."

"You don't understand. This is my first year here. If she tells Principal Hughes about this it won't look good for me to be... you know, getting intimate with a student's parent."

Barbara rolled her eyes. "Think about my offer, honey. We could have some fun." She looked down and licked her lips, then walked out.

I panicked, trying to think of a good story to tell Olivia. A misunderstanding, maybe. Or play it off like I didn't know what was going on: Why did you leave my room so fast? But in the end, I figured I would lay it out, just tell her the truth and see if she believed me.

Once I got my tent situation under control, I went to Olivia's room, but the door was locked and the lights were out. Her car was gone from the parking lot as well.

I had an idea and retrieved Olivia's address from the staff directory. On the way to her place, I stopped at a convenience store and bought a six-pack of beer. A peace offering, one that would give me a little time to explain.

Olivia lived in a vintage brick apartment building in a nice part of downtown Rockford. I should've known. It matched her style: nerdy goth with a side of artsy punk.

It was cold outside. I sat out in front of her building for a few minutes wondering if this was a good idea or not. I don't know if I'd like it if someone from work just showed up at my place. Maybe a phone call would do it, and be less awkward. I pulled up her cell number and called it. I was a little nervous while it rang.

"Hey, you've reached Olivia LaCortino. Leave a message, or just text me like everybody else."

I hung up without leaving a message. What I had to say was too long to put into text. I had to speak with her. I shut off my car and went to the front door, six-pack in tow. In the vestibule, a row of mailboxes and their corresponding buzzers lined one wall. I pressed the buzzer marked "LaCortino" and waited. No answer. Maybe she wasn't home.

An older woman was coming out just as I was about to give up and go home. "You tryin' to get in, hon?"

"Yes, Olivia LaCortino in 304?"

"Oh, those buzzers hardly ever work," she said. "Go on ahead," and held the door for me.

Lucky break. I went up the stairs and knocked on Olivia's door. There was no peephole, but I could see light underneath the door. I waited a minute and knocked again.

Olivia answered the door. "Oh, god," she said and went to close it.

"Wait!" I said. "I just want to talk to you for a minute."

She held the door open, but only a sliver. "You're disgusting. Go away."

"I know what you're thinking, but I wasn't going to do anything with Mrs. Whitlock. She was trying to bribe me to change Bradley's grades."

"Bribe you with her pussy?"

"Sort of, yes! I just told her that I wouldn't do it when you walked in."

A neighbor across the hall opened his door. He was a tall, big guy in an undershirt. "Everything okay here, Liv?" The man asked her, but stared at me, imposing.

Olivia waited a second longer than I would've liked. Finally, she said, "Yeah, it's fine. I got this."

The man said to me, "Keep it down, will ya?" and slammed his door.

"Can we talk about this inside?"

"No. Go home."

"I brought beer." I held up the six-pack.

"There's nothing for us to talk about."

"Please, here me out. Please?"

"You have shitty taste," she said, but grabbed the sixer out of my hands. "What were you thinking?" But she wasn't asking about the beer. Olivia sighed. "Come on in. But take off your shoes and leave them in the hall."

I did.

Olivia's apartment was nicer than I expected. Fancy-looking lamps and plush area rugs gave the space a cozy feeling. It looked much more adult than the empty pizza boxes and overflowing dirty clothes basket that adorned my place. She must've just gotten out of the shower because her short black hair was wet and the air had that damp soapy floral smell. She wore a black t-shirt that was way too big for her and baggy jeans.

"Sit down," Olivia said, but there wasn't much kindness in her voice. She disappeared into the kitchen. I heard the pop of two beer bottles being uncapped. Olivia returned holding the two bottles and two pint glasses. She set mine down in front of me, sat on the opposite side of the couch, and poured her own.

Olivia still wore her funky glasses, but the excessive eye makeup was gone. She looked much younger now. I saw a little spray of freckles on her pale white skin. She was almost cute in an awkward kind of way.

"Let me explain," I said.

"You can try, Alex, but I know what I saw."

Over the next hour, I told Olivia what had happened with the included backstory of the parent-teacher conference. She never said that she believed me, but she seemed to have softened to the idea that I might be telling the truth.

We worked our way through the six-pack. A cheap lager. I had four and Olivia drank two. Then she opened a bottle of red wine. "Here, drink something civilized for once in your life," she said as she poured me a glass. After four beers I had a slight buzz going, I'd have to take a ride share home anyway, so I indulged.

We talked some more about our lives, careers, music. She was smart and funny. Maybe it was because there was no attraction or sexual tension, I found her very easy to talk to and hoped she felt the same. Olivia put some Chicago blues from the 60s on a vintage turntable. "You gotta hear this." After another half hour she was slurring her words a bit.

"All this booze on an empty stomach," I said. "I should probably get going."

"Oh my god, I'm starving and I didn't even realize it. I don't normally hang out with, you know, work people."

"How come?"

She shrugged, suddenly self-conscious. "I guess. I'm fine... no, I'm great in work situations, and if I get too friendly with everybody... I don't know. Maybe I won't do as good of a job, or something. I don't know. It sounds silly." The record player reached the end of a side. Olivia quickly popped up to change the album and the subject. She put on some funk. Maceo Parker she said. Cool stuff I hadn't heard before. She turned the volume up.

I stood, maybe a little wobbly myself. "It doesn't seem silly at all. I get it. But it does help to have friends." And we were indeed becoming friends.

Olivia seemed a little uncomfortable having this heart-to-heart. "I'm super hungry. I'm going to order a pizza. You want pizza?"

I was hungry too. And I had no other plans... "Oh shit, I totally forgot that I blew off Rodney and Susan for trivia night."

Olivia laughed. "You're in no condition for trivia."

And it was already too late. After Mrs. Whitlock trying to seduce me, then getting caught and worrying about my reputation, meeting with my own friends had escaped me. I felt bad, but I would just tell Susan that I had more work than I thought and went home to work. I quickly texted them. I hoped Rodney would understand.

Olivia plopped back down on the couch. "I'm ordering a pizza. You're welcome to hang. But if you stay..." she drained what was left in her glass, "you gotta open another bottle of wine."

My night was open and I was already buzzing a little harder from the wine. I went to the kitchen and found a bottle of Pinot Noir among a few others on a wooden rack near the refrigerator. I didn't know anything about wine other than they came in different colors. I don't know if Pinot Noir pairs well with pizza or not, but I opened it anyway.

I heard Olivia call in the delivery order. "Oooh, we're having dinner soon," she said from the living room. "We need mood lighting."

I liked Olivia. Even more so now. I hate to say this, but she was like hanging out with a classy dude. When I went back in, she had turned one of the lamps off and lit a few candles. The whole room had a comfy warm glow. I was hoping the pizza was going to work some magic, otherwise I was going to end up sleeping on her couch.

Olivia held up her empty glass and pointed to it. "Waiter, I'll have another." She laughed again.

I filled her glass, then mine, and sat back down.

"So, be honest with me," Olivia said, taking a sip. "Were you going to fuck Mrs. Whitlock?"

"She wants me to call her Barbara," I said and laughed. Olivia eagerly awaited my answer. "No, I don't think so."

"You don't think so?"

"I mean, she's hot, for sure. Good body, pretty face. But she was trying to bribe me. It's one of my turn offs."

"Bribery is your turn off? Dude, I saw you. Your face was all flushed. You had a fucking huge hard-on." She laughed again. Olivia set down her wine glass on the coffee table and stood up, nearly toppling over in the process. She crawled over and knelt in front of me. "You're telling me that if she whipped it out and started sucking you off, you wouldn't let her?"

I squirmed. Was this a test? Was she fucking with me? I wouldn't put it past Olivia.

She took off her eyeglasses, put the temple end in her mouth, and swirled her tongue around it.

"I..." Maybe it was the wine, maybe the music, or the mood lighting, but I could feel the blood rush down to my crotch. My mouth must've dropped open. "No... I..."

"If Mrs. Whitlock, Barbara, got down in front of you just like this," Olivia pulled at my legs to center herself, then took off her t-shirt. She had a white tank top underneath, but no bra. She didn't really have much in the breast department, but I could see the outline of her nipples. She set her glasses down on the table, took a gulp of wine, then refocused on me. "And pulled out that thick cock, you wouldn't let her have a go?"

I drank some more wine, trying to settle myself, but my mind was swimming, and my erection was growing. Even though I didn't have any intention of fucking Olivia, having a woman so close and flirty was having an effect. I didn't know what she was doing or if she, or I, might regret it. "Aren't you a lesbian?" The question just shot out of my mouth.

Olivia reeled back and cackled. "Why, because I have short hair? Don't be such a doofus."

"You just seem like, I don't know..."

"Why? Would that turn you on, too?"

"I'm telling you, I wasn't going to fuck her," I said.

Olivia ignored me. Her eyes were mischievous. She was toying with me. "I'll bet you'd love that. So there's Barbara, slobbering all over your big stiffy and who walks but lil' ol' me. You'd just love it if I joined in, right? Got right down there next to her. Maybe she could lick your shaft while I suck on your balls. Are they big? Do you think I could fit both of them in my mouth?"

"I don't know what you're-"

"Look at you! You can't even control yourself." She put both hands down on my hips and eyed me. I was totally pitching another massive boner tent. Olivia feigned playfully at its size, then leaned back and pinched her nipples lightly through her shirt until they hardened. "You're powerless. Helplessly turned on, even by this short-haired, cunt-licking lesbian." She smiled, took a deep breath, and drained the rest of her glass.

"Well, I didn't do anything, you know," I said, trying not to focus on the way her tattoos gave way to pale white skin and her small breasts.

The record finished. Olivia raised an index finger, telling me to wait. She got up and went to the turntable console and put on indie rock from some band I'd never heard. My erection hadn't gone down. There was no sense in hiding it. I moved into the corner of the couch and crossed my legs to sort of reposition it.

Olivia had her back to me. She moved to the music, a little drunk, but feeling the rhythm. She spoke to me, but still faced the other way. "You know what? You're right. You didn't do anything. But you were sure as hell thinking about it."

"I mean, of course, I was thinking about it. That kind of shit doesn't happen to me everyday."

Olivia let her baggy jeans drop to the floor. Holy shit. What she lacked in cup size, she made up for in her behind. Her butt was tight and had that perfect curve. A little bigger than I expected from only seeing her in those baggy clothes. A thin black thong accentuated her flawless round bottom. Now, she was right, I felt powerless.

She turned her head without looking at me. "You're damn right you thought about it. And what are you thinking about now?"

I went to take a drink, but my glass was empty. My breath was short, but the wine made me feel uninhibited. Olivia had literally exposed herself. It was time I took a chance. "I'm thinking that you have one of the greatest asses I've ever seen. Certainly the best I've seen in real life. I want to squeeze it. I want you to grind it on me."

"Naughty, naughty" Olivia said, and came back over to the couch. She stood in front of me. "No self control. No discipline." I let her move my leg back over so my tent was back on display. She purred, "Take it out."

There was still some hesitation on my part. I'd been down this road before with a coworker. "Look, I've had an awesome time here tonight. Really." I started to get up.

Olivia pushed me back down. "Maybe I'm a lesbian. Maybe I'm not. Maybe I'm just a woman who knows what she likes and fucks who she wants. Now, take it out. I want to see what Barbara Whitlock was trying to get a piece of."

She was small, but forceful, and it was sexy. My hard-on was undeniably straining against my pants, but to pull out my penis crossed a hard line. Olivia had crossed a line of her own by stripping in front of me. I vacillated back and forth between what I knew I should do and what I wanted. She acted so radically different than how she was at work. I had no idea what to expect.