Summer School Session

This is my entry into the

Literotica Summer Lovin' Story Contest 2024

. I always like to reinforce that like my author name says, all of the stories I tell here have a basis in truth and are based on actual events from my life. That being said, I do like to add some twists & embellishments to keep them interesting for the readers.

Please remember, authors & our stories thrive on ratings. We get better with feedback, so PLEASE leave your comments on our stories. I also love when people guess in the comments what parts are "Truth" and what I added for "Twists."

Everyone in the story is 18 years of age or older.

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My wife Sherri and I had been together for nearly a decade and half with one daughter, Jackie, who was in the summer between 6

th

and 7

th

grade. Sherri was the assistant principal at our daughter's small private school in an upscale area outside of the Twin Cities and had been working there for a few years. I had left the large corporation I had worked for and had branched out as a private consultant to give me more flexible time with my family.

When we were first together, Sherri was a tall, thin blonde with small perky tits, tight ass, and long lean legs. There was an old store, "bebe", that Sherri could have been the perfect model for at the time. Age and motherhood do change things and over the years, she had filled out in a good way. Her breasts were now larger and fuller and were just as sensitive before which gave me more to grab, lick and touch. Sherri's long blonde hair was gone, she now had a close-cropped platinum cut that was in style. Her ass was larger, too, but her workout schedule had it toned and looking full and sitting high on her frame.

Similarly, I was in decent 'middle-aged' shape. A bit heavier around the middle with some grey creeping into the hair at my temples. Fortunately, a consistent schedule at the gym and moderate runs kept me on track.

Like many couples, our sex life started off red hot in the early years of our relationship. We had all sorts of adventures: from panty-less car rides, to sex in front of my high-rise windows, to an occasional threesome with a female friend. But ALSO like many couples, that excitement waned over time. Family, jobs, stress, age, and routine cooled down our sex life for several years. We tried all the tricks - from 'writing down our fantasies' to 'scheduling date nights' with few positive results. The fact of the matter was that when you have a toddler or pre-teen constantly in the house, plus limited free time, plus roles in the local community, plus full-time jobs, opportunities for sexual adventures decrease.

Fortunately, by the time our daughter reached this age, we found ourselves starting to get some of our time and adventures back. Jackie's sleepovers with friends were more common and an opportunity for us to reconnect. We were more comfortable leaving her with family and friends for a weekend away which provided more opportunities for private fun and frolicking. Sherri had reintroduced lingerie and heels to her bedroom wardrobe, we shopped together online for a nice collection of lubes and toys we hid in a bedside drawer. We started watching adult movies together and Sherri even made passing remarks about 'when we used to invite a friend' to the bedroom.

It was a hot and humid July morning when I was sitting in my office working on an endless spreadsheet for a client. Jackie was spending the day swimming at a friend's house and needed to be picked up after dinner. I was staring out the window, half-wishing I could leave and sneak off for a round of golf but knowing that the day's humidity was out of control, and it would be miserable outside. We had already been getting warnings that late summer storms could roll through the area.

Sherri was also at work that day. While the school was closed and deserted for most of the summer, she would still have to go in for a few days at a time here and there for administrative tasks. I always felt bad for her because the school was an older building with virtually no air conditioning. Her office, which she shared with the principal and some admins, had a small window unit, but with the rest of the school closed and stagnant, the heat could get stifling.

Just as I resigned myself to sheet 17, tab 2d, my phone pinged with a text message.

Sherri: >> How's it going?

Jason:>> Good. You.

S: >> Fine. Sorting through tuition stuff.

>> You have lunch plans?

J: >> Nope. Want to grab something?

S:>> Y. Swing by here at noon?

J:>> Sounds good.

A few hours later, my phone's reminder went off and I went down to my car to drive over to the school. As soon as I opened the door to the outside world, the thick air hit me. The sun was blazing and heating the pavement in the parking lot reflecting it back on me as I crossed to my car. Opening the car door, a blast of heat me, somehow hotter than the air outside. I started the car, opened the windows, and cranked the AC hoping for some quick relief for the drive over.

I walked up to the door and pressed the buzzer. Even standing waiting for the door to open, I could feel the sweat starting to bead up on my neck and back. The door buzzed loudly, and I heard the lock click to let me in.

If the outdoor heat was bad, the inside of the school was even worse. The air was stagnant and heavy and since the building had been mostly closed for over a month there was a musty, almost suffocating smell to it. As I climbed the stairs to Sherri's office, I could see dust drifting through the rays of sunlight streaming through the windows.

I reached the door to Sherri's office, looking forward to the cool air that awaited me when I saw a note taped to the outside.

"Working upstairs. Come to room 401."

I cursed out loud, knowing that the 4

th

grade rooms were up yet another flight of stairs that I would have to climb in the miserable environment. After trudging up the stairs and walking down the hallway, I was admittedly more winded than I should have been with the sticky, stale air feeling like it was physically weighing me down.

There was also an oddly creepy vibe to the school. Normally, a school is full of activity and noise yet without the children, it was eerily quiet. The lights were off and there was only reflected sunlight from classroom windows illuminating the hallways. The building seemed to creak and groan in the summer heat as I finally reached the classroom at the end of the hallway.

The door was open, and I started to complain as I walked through.

"Could you have picked a room further away...Oh, I'm sorry....uh."

I stopped short because where I was expecting my wife in the room, there was someone else sitting at the teacher's desk. Her back was to me, but I could see she had long, black hair that was styled down to her shoulder blades. She was overdressed for the summer day with a black pinstripe jacket and matching skirt. I could see she had stocking-covered legs tucked under the desk with a pair of shiny black patent heels.

The woman swiveled in her chair to face me, and it took me a moment to realize I was staring at my wife. Her platinum hair was covered by the long, black wig with bangs covering her forehead. She had a pair of black glasses perched on her nose and ruby red lips with smoky eye makeup. Under her jacket, she wore a white blouse that was unbuttoned and plunging low on her chest. Although not hugely endowed, her breasts had grown since our daughter was born and she was wearing a pushup bra to make them larger and fuller. Her skirt was shorter than it first appeared, ending well above her knees and her knees were demurely pinched together as she turned.

"Mr. Drake. I'm Ms. Summers. Thank you for coming in today. Please take a seat." she said gesturing to a smaller child-sized chair by the desk.

I tentatively followed her instructions and balanced in the red plastic chair while she continued, "As you know, your son, Benjamin has been struggling this year. I called this meeting to discuss his options moving forward."

Sherri was now facing me, with her stocking-clad legs crossed as she brought a pen to her ruby-red lips.

"I, um, I'm not sure what to say." I said still trying to catch up to what was happening. It had been a long time since we had done any role playing and even then, it was more, 'Sherri wears a sexy costume, and we have sex' sort of thing. The fact that we were in an empty school with letters, numbers, and kids' posters on a wall while my wife was the embodiment of a sexy schoolteacher? It wasn't just the stuffy heat that my head spinning.

"Well, you have a couple of options. We can hold him back by a year or..." she paused while she uncrossed and recrossed her legs, like Sharon Stone in Basic Instinct. Also like the movie, she showed that her stockings ended at her thighs, and she was uncovered under her skirt. I saw a flash of her bare pussy before it quickly disappeared. "Or...we can work out a separate arrangement."

"What do you suggest?" I asked as I felt my cock instantly swell inside my summer shorts.

"Well, Benjamin is a great kid, but he tends not to listen to my instructions. So, I wonder if that's coming from someone else ... like you." Sherri lifted her hips off her seat and pulled her short skirt up higher. As she pulled it, she revealed the lacy tops of her stockings and an expanse of her toned and summer-tanned thighs. She was able to slither it up over her hips, revealing her bare, trimmed pussy.

She often varied the style of her pubic hair, at times keeping it fully shaved, other times letting her bush grow in. Because it was summer, she had it mostly shaved with a small, tightly trimmed landing strip (probably to accommodate her summer swimsuits.) While most of her body was covered in a light bronze summer tan, there was a pale 'v' of skin that started at her hips, went across her pelvis and down to her crotch.

I have always been attracted to a woman's tan lines, so it was a dual fantasy laid out in front of me. A sexy schoolteacher in stockings, showing me her exposed pussy with obvious tan lines caused my dick to swell even more. As she settled back into the seat, she shifted forward so her ass was at the edge of the chair and she spread her legs as wide as the chair would allow.

"So, Mr. Drake. Let's test YOUR ability to follow directions. I need you to get over here, and lick my pussy until I cum. Is that clear?" To accentuate her instructions, she used her thumb and middle finger to spread her lips and flicked her clit with her index finger.

As I stood up, my shirt stuck to my back having sweated up against the hard plastic. I dropped to my knees in front of Sherri and for the first time, I felt the cool, industrial tile floor on my bare legs. I looped my arms under her thighs and gripped her quads. Her skin was wet and slippery with sweat, remnants of her tight skirt against it.

I licked up her inner thigh, following her tan lines, purposely avoiding her wet slit. I could taste the salty sweat on her as I moved my tongue up and over her pussy and back down the other leg. Her scent was musky, another indication of her arousal and the temperature. Heat was emanating from her womanhood, and I felt it as my face passed by. A low moan escaped her as she groaned, "I don't recall telling you tease me, Mr. Drake. Are you going to follow directions or not?"

She gripped the back of my head with her hands and pulled me into her. My tongue found her dripping opening and I licked up and down the length. Her fingers gripped my scalp as I pushed my tongue into her, licking up her flowing nectar. I took long, slow licks up her outer lip flicked over her clit, and moved back down the other side. I continued that pattern, causing her get wetter under my motions. Her labia seemed to swell and moisten with each passing stroke of my tongue while her clit grew and poked out from Its fleshy hood.

She crossed her legs behind my neck and the points of her heels started to subtly dig into my back, trying to pull me in closer. I changed my focus to using the tip of my tongue on her swollen button. Alternating between rapidly flicking and circling it, I heard a low hiss escape her gritted teeth.

"That's it, baby. Lick my pussy. Lick my clit. I'm getting close." Sherri's raised voice echoed off the walls of the empty classroom. Her legs felt heavy on my shoulders, her muscles tightening and her breaths coming faster and deeper. Using a tried-and-true technique, I pursed my lips, surrounded her clit, and formed a vacuum by sucking gently. Then, inspired by the decorations around me in the clammy classroom, I started to trace the letters of the alphabet on her clit.

"Fuck. Fuck. Fuck." She repeated as she rolled her hips against my face. I was breathing heavily through my nose as I continued through the alphabet. I had just hit the letter "m" when she went over the edge.

I felt her entire body shudder and her legs locked into my back. Her hips were thrusting into my face as her fluids flowed into my mouth, her hands gripped my head, forcing me to continue to feast on her pussy. Sherri moaned and gyrated as she pushed her pussy into my face for a second orgasm in a matter of seconds.

"Yes! Yes! Fucking hell....yes.....I'm coming again!

With her legs locked around my neck and her hands pulling my head in, I felt like I would suffocate in her pussy. Fortunately, just as she rode out the wave of her climax, she pushed my head away. My head and face were covered in sweat from the heat of the room combined with having her legs keeping me trapped. I shifted slightly and felt long sweaty strips on my back where she had been resting her legs. When I finally looked up at my wife, her face was beet red, and sweat was pouring down her forehead. Her chest was dotted with beads of sweat and her white shirt was visibly damp against her skin.

"So, Miss Summers, did I pass?" I asked.

"Mmmmm...not a bad start. But that was just a pop quiz. There's still a test for you to pass."

Sherri slithered out of the chair and rolled it off to the side. She didn't bother to pull her skirt down, allowing me to stare at her exposed pussy and ass as she turned and sat on the teacher's desk. She kicked off her heels and slid her ass back, which allowed her to put her heels on the desk and spread her knees wide. Her pussy spread open before me, and I could see her lips were swollen and wet.

I lifted myself off the floor, quickly unbuckled my belt, and dropped my shorts and boxers to the floor. I stepped out of them and approached her with my rigid cock leading the way. Just as I was about to slide into her, a stocking foot pressed against my chest.

"Stop" she said. "Patience is a virtue, you know."

I watched as she leaned back on the desk and shifted slightly. Her stocking-covered feet wrapped around my cock and started rubbing up and down the length. Her feet were moist and sweaty as they stroked my cock. Ms. Summers jerked me off with her feet while simultaneously untucking and unbuttoning her shirt. I watched as she unclasped her push up bra in the front and let her tits fall free.

For the second time, I was treated to a view of the contrast of her tanned skin. While her chest was flushed and sweaty from the heat, it was also a darker bronze than her legs. That made the pale tringles on her tits stand out even more. Her pink nipples sat stiff on her breasts and they jiggled slightly as she moved her feet around my cock.

Somehow, her glasses were still on her face, and she stared through them at me, never losing eye contact. With one hand, she started playing with one of her nipples, while the other moved toward her spread pussy. I tried to focus on the sensations of the damp nylons stroking my cock, but I was distracted when she plunged two of her fingers deep into her vagina.

"It's ..ungh...been a while, Mr. Drake. Let me make sure my pussy is ready to take that cock."

Her index and middle finger were buried in her cunt, and she was squeezing her breast. Her feet were no longer moving on my cock as she focused on her own body. Just as she seemed about to orgasm again, she pulled out her fingers with a low groan. Her feet fell away and back onto the desk as she tried to prop herself up on her elbows. Her tits fell down a bit and I saw her nipples were perky and swollen.

I stepped forward and gripped my dick to line up with her opening. Because of our positions, I watched as my cock split her lips and slid inside her. I pushed slowly, savoring the view of my shaft slowly sliding into her, as her lips parted to grant me entry. I finally stopped when flesh met flesh and my groin was pressed against her spread legs.

I pulled back slowly, allowing her juices to fully coat my dick before I repeated the action, a bit faster this time.

"Yes, that's it, I love the way you feel sliding in and out of me. Keep doing that."

Knowing that I was required to follow the teacher's directions, I kept up the pace, resisting every urge to slam harder into her. We continued like this for what seemed like forever. The sensations were amazing, but because I was still slowly thrusting, it allowed me to focus on not coming too quickly. I had my eyes glued to the way her pussy lips would slightly roll open and closed around my shaft as I pushed and pulled back forth.

After a few minutes, Sherri's elbows and arms seemed to give out and she slipped back onto the desk. Because the desk wasn't very wide, her head slipped over the far end, putting her in an awkward position. Seeing this, I grabbed her hips and pulled her toward me while I tried to step back. My timing was slightly off, and the result was I slammed my cock into her with more force than I intended. For a split second, I thought I had hurt her, but my worries were quickly calmed.

"OH SHIT! YES! THAT'S IT! FUCK ME HARD!"

With my hands on her hips, she wrapped her legs around my waist as I picked up the pace and began to fuck her hard and fast. I felt her ass and thighs ripple with every thrust as the sound of our skin slapping against each other filled the classroom.

Because of the increased action, I suddenly had to make a stronger effort to keep from coming. I tore my eyes away from her pussy and saw that her glasses had fallen to the ground. Her face was covered in sweat and the wig looked to be both slipping off and sticking to her forehead at the same time. I watched her tits bounce with every thrust as her red lips parted, gasping and groaning.

The sheer eroticism was all a stark contrast to the area around us. As my wonton wife was spread open like a slut on the desktop, cartoon images and childish posters surrounded us. Multi-colored cubbies were at the far end of the room and the tiny desks in neat lines covered the patchwork rug on the floor. The empty room was filled with the sound of skin slapping against skin and the scent of her arousal filled the air.

Her pussy was clenching around my cock as I felt myself nearing completion. At the same time, I could feel Sherri approaching her second orgasm of the afternoon. Suddenly, a deafening buzzer shattered the silence. The entire building seemed to shake as the harsh noise echoed through the empty halls. I physically pulled away and slipped out of her as I scrambled to pull up my shorts convinced; we had set off some sort of "impurity alarm" in the innocent schoolroom.

"What the fuck?!?!?" I yelled. Sherri was sitting up, her legs spread, her tits hanging down through her open blouse. She chuckled slightly as the buzzer stopped and the echoes died down.

"Sorry. That's the end of period buzzer. It goes off every 90 minutes even during summer."