An Education – Anal – – Free Sex Story

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All characters herein are assumed to be 18+ years of age and any similarities to persons living or dead is purely coincidental.


Winter semester at the University of Michigan is a cold and unforgiving one. Jackets zipped up to the eyeballs, students shimmy across the campus in silence, narrow trails forming spiderwebs in the snow. When the wind picks up the buildings funnel the blowing snow like a jet engine through the quad. On this type of day undergrads either stay in bed or double-time it to class; there is no socializing when the ice is pummelling your face.

And yet on this particularly bitter Tuesday, 20 degrees with gusting snow, this is precisely the scene Professor Jane Hoffman observed out of her office window. She was waiting for her standing 2 o’clock appointment to show, PSYCH 220 student Jerome LaGrange, and it was already 2:20pm. If it wasn’t for the 2 students she was watching brave a conversation in the exact middle of the quad, their silhouettes fading in and out of focus in the snow, she might have been more upset at being kept waiting.

As she watched the situation became more curious: the taller of the two characters was dressed only in basketball shorts, a hoodie and backpack, the shorter one in a full parka, and they were having a full-on dialogue in the middle of that February storm. Oblivious to the freezing maelstrom around them the taller one was shaking their head to whatever the shorter was saying, pointing to their watch and the building Prof. Hoffman was currently watching them from. After a few seconds of back-and-forth, the person in the shorts shrugged their shoulders and flipped their backpack around to the front, opening it and fishing something out.

From up on the 3rd floor looking down it was hard to tell what they pulled out of the bag, but it appeared to be a small package, perhaps wrapped in foil, the aluminum glinting weakly in the tiny slivers of light that poked through the clouds. The taller person held it out and it seemed that the shorter one was hesitating to take it. Reluctantly the smaller figure accepted the unknown goods, and after a second, brought it up to their face, perhaps to smell the contents.

Snow obfuscating the view momentarily it looked like the shorter one opened their parka and placed the stash in their back pocket slowly and carefully. A quick hug between the two and they went their separate ways, the taller character heading towards the building Jane was spying from.

‘Did I just watch a drug deal happen in front of my eyes?’ the professor thought before glancing at the clock on the wall, her curiosity now waning quickly.

It was 2:30pm, she’d waited long enough, so she started packing her bag up with tests that still needed marking. Grabbing her coat and heading for the door she almost had her hand on the knob when the door flew open, a bit of the winter wind blowing into her otherwise tiny, warm office.

“I’m so sorry, ma’am, I know I’m late. I’m still not used to these Michigan winters. It’s not an excuse, I’m sorry…” the visitor rambled, taking their backpack off and shivering from the cold.

Jerome LaGrange was a 6-foot-4 Junior from Louisiana, a full-ride scholarship holder, a starting wide-receiver for the Wolverines, and currently a 1.7 GPA student. The prof gave him a once-over and noticed he was also likely the most underdressed student on campus at that point. Skinny black legs poking out of a pair of snow-crusted shorts, she realized he was also the tall protagonist of the scene she had just observed out her window.

A bit more perturbed by that realization she shook her head and replied, “I’m sorry too, Jerome, our appointment was for 2pm and I’ve got enough work to take home as it is.”

“Please, prof, I need help to get through your class and pick up my average,” he pleaded, bringing his two massive, ungloved hands to his head in prayer, “otherwise coach is gonna cut me and I’m gonna lose my scholarship and my momma’s gonna kill me! I can’t let her down, ma’am, that woman gave everything to get me here.” His eyes now closed in genuine reverence.

It didn’t seem to do the trick as Professor Hoffman was still giving him the stink-eye.

“You say you need this so bad, but I see you out there taking your sweet time doing whatever that was,” she said, gesturing to the window overlooking the previous scene.

Eyes opening and confused, Jerome looked out the window to the see the quad howling with snow, now devoid of any person.

“Oh, yeah, sorry about that, prof. I just met up with a friend of mine on my way here, but you’re right, I should’ve just met up with them later,” he clarified.

“Seems to me there was a little more going on, I think,” Jane questioned further, “to be meeting out there in this weather!”

“Naw, it was just a girl I know that wanted to hang tonight,” he explained.

“Is that right? Because it looked like a transaction or something from up here,” the professor probed. “Are you caught up in something illegal, Mr. LaGrange?” Then a little more directly, “Are you selling drugs on campus? You’re going to throw your life away doing that!”

Jerome, now starting to clue into what the professor saw, waved it away saying, “Naw, naw, it’s nothing like that. I’d never do that and risk it all for a little cash.”

Still not buying it, Ms. Hoffman put her hands on her hips and doubled down, adding, “Ok then, what was in the package you gave that young lady then?” and with that she nodded and pointed to the snow-covered backpack now sitting by his feet.

Starting to bead sweat, Jerome nervously glanced at the bag and tried to brush it off.

“Oh, that’s just something she needed to have before we tag up tonight. It wasn’t drugs or anything.” He was not convincing enough.

“You need to tell me the truth, Mr. LaGrange, or I’m leaving this office and my help goes with it,” she explained, providing him an ultimatum. “Show me what’s in the bag or I’m out of here.”

Jerome paused for a moment, unsure of how to proceed. After about 15 seconds he sighed, slumped his shoulders down and unzipped the bag at his feet. He rummaged around inside and seemed to find what he was looking for.

“I can’t fail this class,” he looked up and said, pausing one last time, hoping he wouldn’t have to reveal his holdings.

“Then out with it, Jerome”

Looking away from his professor ashamedly he pulled out a small metal object from his bag and held it in front. It was smooth, stainless steel that started from a rounded tip, flared out to an inch diameter and then back down to a little stem, capped off with a circular base fitted with what seemed to be a gemstone.

It looked like a futuristic dreidel, Jane thought curiously, and plucked it from his hand.

“Well, what is it?” she asked, turning it around in her palm, eyeing it from different angles, “Some kind of fidget toy?” Jane brought it to her face, as she saw the person do outside, and gave it a sniff, smelling nothing but metal and apparently Jerome’s hand cream.

Now more confused than ashamed, Jerome explained, “It’s a buttplug, ma’am.”

“What do you mean ‘a buttplug’?” Jane queried while still turning it around until apparently the right angle allowed her to visualize its obvious use. “Oh, my word!” she exclaimed and dropped the object into Jerome’s hands.

Putting it quickly back in his bag, Jerome looked up and said, “Is that all you need to know?”

Professor Hoffman was reeling a bit, trying to wrap her head around why a star athlete would be walking around handing out Sex toys on campus. “No, this just brings up more questions, actually. What is someone going to do with one of those outside in a snowstorm?”

“I told you, that was a friend of mine that wanted to hang tonight. She asked me for one because she wants to hook up. I gave her one of my spares so she could get ready,” Jerome stated, matter-of-factly.

“So you’re telling me that you stopped in the middle of the worst storm in February to give a young lady an Anal device so she could what, take it home and use it on your date tonight?” Jane asked, trying to put the pieces of the scene together.

“Kinda. These girls know about me and that I only have two rules when it comes to hooking up: 1. I don’t fuck Pussy, sorry, um, have vaginal Sex; and 2. they gotta plug up beforehand,” Jerome expounded, his confidence coming back to him. He waited a second then finished, “That ‘young lady’ stopped me and begged me for one of those, so I gave her one and she put it in so she would be ready for tonight”

Jane’s eyes grew wide as she now realized that the shorter person wasn’t smelling the contents of a package of drugs before putting it in their pocket but was rather likely wetting a Sex toy in their mouth before inserting it anally, all out in the open during winter’s worst.

She was starting to think it would have been better if it was drugs, now that she’d incorrectly accused a future draft pick of trafficking, instead of forcing a student to reveal a private sexual matter to a tenured professor. Realizing she’d overstepped and not wanting to wade into any more potential student-teacher improprieties Jane started to back peddle and change the subject.

Flattening out her skirt superficially she stood up straight and said earnestly, “I’m sorry for accusing you of that, Jerome, it wasn’t right. Now let’s see if we can get you on the right side of the bell curve.”

With that she moved behind her desk and motioned for him to sit on the other side. Glad to be out of that awkward scenario, Jerome sat down and pulled out his class notes, ready to learn. They worked for an hour or so on the course material she’d been lecturing about for a month already and while it seemed to go well, Jerome grasping some concepts he hadn’t before, the awkward, unanswered questions about what had just happened lingered in the air throughout. Jerome could tell that she was now looking at him in a very different light and wasn’t sure what to make of it. When it came time to leave, he took the initiative and apologized again.

“I’m sorry again for being late, ma’am. I’ll be here on time next time,” Jerome promised, leaving the office, the swish of his now-dry basketball shorts getting fainter as he made his way down the hall.

Turning and leaning back on to the closed office door, Jane Hoffman exhaled raggedly, letting out the anxiety she trapped in her lungs, bending at the waist and putting her hands on her skirt. For the last hour she’d been fully distracted by the situation and couldn’t keep her mind from trying to work out all the questions Jerome’s revelations had brought to the surface.

Some of the questions were procedural, nagging ones: He just walks around all day with Sex toys in his bag, just in case? How many students are wearing these in class? How does he keep track of who’s got which toy? Why is he wearing shorts in the winter?

Some questions were purely sexual: How does it feel to have one inside, let alone have Anal Sex? Why do they have to ‘plug up’ before they ‘hook up’? Why doesn’t he have vaginal Sex and why are these girls doing all this for him? What size is his penis, anyway?

It was these latter questions that were giving her anxiety.

Jane Hoffman had grown up in a conservative Jewish household and was taught that the pursuit of knowledge was one of the most worthy labours. She excelled in school but kept to herself, eschewing boyfriends and a social life for academic advancement. Other than a couple of short-term relationships, and a few disappointing sexual encounters in college, Jane had put Sex, and all the entanglements it carried, to the side. Graduating from college and going straight into academia she buried herself in research and never looked back, having fast-tracked tenure at the U of M and being a respected, published researcher in her field by 40.

Now at 48 and doubled-over winded against her office door, it seemed her stoic asexual resolve was waning. Looking down she noticed a dark patch on her light grey skirt. Reaching down and feeling underneath, her fingers reached the wetness on the crotch of her pantyhose first, her panties having been soaked through. ‘Oh no,’ she thought, ‘I hope no one can see this.’

At that moment Jerome was already down the three floors and reaching the building’s exit, flipping his hood over his head and preparing to brave the cold outside.

“I see you, professor,” he whispered to himself and smiled.

That night the professor’s nagging questions kept her unfocussed while marking the papers she’d taken home to her one-bedroom condo. What normally took an hour dragged on for three and when it was finished she was tired, her mind seemingly running in two different directions for the better part of the evening. At 9:30pm she got ready for sleep, showering and running through her bedtime routine quickly before settling in her bed.

Tired as she was, she couldn’t sleep. Too many thoughts about too many buried subjects were swirling in her mind and closing her eyes seemed to make it worse. She thought about the metallic taste of that cold steel toy in that girl’s mouth and it made her salivate. She thought about the soft ‘plop’ sound only she would’ve heard in that snowstorm as it went in her and it made her butt cheeks clench together involuntarily. She thought about Jerome and hugging him close out on the cold quad and it made her nipples stand firm against her pajamas. She thought about his black penis under those loose shorts and little sparks of electricity shot across her lady parts below.

Squirming uncomfortably under the sheets she ran her hands down the top of her chest, around the sides and underneath her ample C-cup breasts, grazing a fingertip to each nipple and sending a current through her when they made contact. Rubbing her stomach, she could feel her tiny abs defining themselves with the repeated clenching and releasing her mid-section was experiencing. Dragging her hands down to her hips and assisting them with the now swirling motion they were making, she pushed and ground her behind into the bed with each orbit.

Moving her hands towards the unkempt bush of her pubic hair she sent her fingers in exploringly, each eventually finding moisture as they made their way over the top and down her vulva. Everything was sopping, so when she sent two fingers between her hairy lips, curling them up inwards, they slipped into her lightly used Vagina effortlessly. Her fingers now two knuckles deep inside and the heel of her palm resting against her clitoris she tugged gently upwards to generate that familiar relief she’d sought on so many lonely nights; but tonight, something was off.

The thoughts swirling around in her mind weren’t lining up with what her hands were doing below so she turned herself onto her side, bending her top leg up to her stomach, all the while still tugging faintly at herself. With her Free hand she slid it along her back, under her waistband and down the crack of her butt, fingers hovering over the wrinkles of her hole tentatively. Some of her juices had slid down into her crevasse already but she reached further and scooped some more from the front with her fingertips, each making sure to return some of those juices to the entrance of her back door.

The professor had never had anything in her butt before and was wincing even before her fingers contacted the pursed sphincter of her anus, but the thoughts in her head were pushing her forward. With each touch of her fingers her Anal muscles flexed and clenched and then relaxed around them. Once fully lubricated with the mess she was making up front, the tips of her first 2 fingers now dripping, each touch started to last longer and each tip started to go deeper. As the tugging rhythm of her hand up front started to line up to the clenching pattern her hips were making behind, she turned into her pillow and let out an audible squeak as one, then two full digits slipped past her sphincters and inside her butt.

Two fingers fully buried on either side she see-sawed her hips in that bed, pushing on her back hand faster and faster until the palms were spanking her cheeks, thoughts of Jerome’s black skin pressing up against her from behind.

The usual engorgement of her clitoris and quaking of her Vagina were now accompanied by a frenetic spasming of her Anal muscles and as she peaked in her Orgasm she let out a primal scream she’d never made before, loud enough that the neighbours remarked it over the evening news.

Her mind now at peace and her body now satiated, Professor Jane Hoffman fell immediately to sleep, frozen in that position. Around 1am the tips of her fingers slid out of her butthole unceremoniously.


The next morning Jane woke up refreshed and rejuvenated. The previous day’s storm had abated and the errant thoughts from yesterday no longer swirled around in her head. The skies were clear and as she made her way to campus she remarked to herself how juvenile and unprofessional yesterday had been, making a point to apologize to Jerome again and to redouble their efforts to ensure he brought his mark up past the NCAA minimum.

Her PSYCH 220 lecture hall was starting to fill up as she setup her laptop and organized herself for the morning lecture, yet only half of the 100 registered attendees had arrived despite the improved weather, and there was no sign of Jerome. Resigned to having to wait to speak to Jerome until their standing 2pm appointment she turned on the projector and was about to begin the lesson when the back doors flew open and six members of U of M’s football team rushed in, followed by some assorted other classmates. One of the tardy Wolverines, a 2nd string lineman she believed, spoke for the group.

“Sorry, teach. Coach had us in for an early morning workout.”

“Ok, ok, let’s get settled,” the professor replied, understanding of the hectic schedule college athletes are put upon.

A few of the seated students dapped the players as they passed by, but Jerome was getting the full hero’s welcome as he made his way to an open seat in the middle of the lecture hall. Some of the male students were standing up and bro hugging him with words of praise and a few women stood to give him a quick hug or peck on the cheek.

Watching this and losing a little patience the professor noticed one girl whisper something to him as she stood up and Jerome remarked it with raised eyebrows. When they hugged, he let a hand slip quickly to the back of her pants and gave her a little tap in seat of her jeans. The girl jumped slightly then sat back down in her chair, resting her head in her hands embarrassed.

The professors jaw dropped silently, not believing the stealthy interaction she just witnessed. Just as she was starting to think she imagined it, the same scenario started to unfold about four students later down the aisle. This time, however, when they hugged Jerome reached down and before he tapped the middle of her yoga pants, he looked up and locked eyes with the professor for a second. This girl didn’t jolt up, however, but simply sat back down with a devilish grin.

Professor Jane Hoffman felt as though she’d been struck by a baseball bat. She stood there in stunned silence well after everyone had taken their seats and were now waiting on her to begin.

“Oh, um, yeah, we left off last class talking about…” she trailed off, losing her train of thought. Looking to have her presentation help kickstart her memory she searched around for the file on her computer, having trouble locating it and getting increasingly more flustered. Finding it she reached over and turned off the already-illuminated projector, clicking it back on and muttering curses under her breath. Once the notes were up and she began reading, she started to regain some composure.

A little more than halfway through the period she had settled back into her normal rhythm and looked out on to a hall of the usual mix of faces; some alert and taking notes, some looking down at a phone, some drooping and popping up as they dozed off/woke up, and some fully asleep in their crossed arms. When she glanced at the two girls Jerome had ‘greeted uniquely’ though, she noticed a different expression plastered on their faces.

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