At one time in my life, tutoring was the worst part of my week.
During college, desperate to make money, I landed a job tutoring for an ultra-wealthy mom in the suburbs, who paid me a less-than-fair son to sit with her average-achieving 12 year-old son and watch him do his homework. Eventually, she referred me to her friend, Jenna, whose, son Elliott, I was hired to tutor.
When I first arrived at Elliot's house, I needed to take a moment just to marvel in its size—and the ornate antique architecture of its front. In the city, where the best you could do for housing tended to be two-story townhouses, this was a mansion. Maybe, I hoped, it would mean a little bit more pay—though, of course, it would also mean being appreciated for my labor, which certainly hadn't happened. Keeping this (perhaps fantastical) dream in my mind, I rapped my knuckles on the immense wooden door.
There was shuffling and the shout of voices, and the door swung open—and I was greeted by a dazzlingly beautiful woman with a dazzlingly warm smile and an even more dazzlingly lithe body.
"Hi!" she said. "I'm Jenna, Elliot's mom. You're Nick?"
"That's me!" I smiled and quickly adjusting my curly brown hair, so as to look less like a schlub. Jenna smiled. Given her son's age, she couldn't have been more than 40, but she certainly didn't look it; she had the body of a runner and an enticing pair of breasts--and, as she turned, I saw that it all culminated in her tight ass, which was cupped perfectly by her black leggings,
She quickly ushered me in and sat me at the long table of their immense dining room. It was the kind of room that was almost certainly filled with aristocrats and servants a hundred years ago, but I didn't pay as much attention to the architecture as I did to the sway of Jenna's tight ass as she turned to call for her son.
After some calamitous crashing above the ceiling and the thunderous stomp of feet down the stairs, Elliott appeared in the doorway, clearly unenthusiastic to be there but nonetheless being courteous.
"He spent some time out of school due to an illness," Jenna began. "So he'll need to do a lot of catch-up in English and Math. Other than that, if you could help him with whatever homework he has, that'd be great!"
She smiled sweetly and laid a hand on my shoulder, electric shocks traveling into my skin. I nodded quickly, and she left the room, allowing Eric and I the space to begin working.
Elliott was funny and earnest, certainly better than other kids I had tutored. But in the following weeks, it wasn't him that I looked forward to—it was Jenna. Every moment I wasn't helping her son with work (and even some when I was), I ogled Jenna's body, trying to commit the swell of her tits and the curve of her ass to my memory, to, ahem, review before bed.
One day, all my staring caught up with me. Midway through a tutoring session, Elliott mom came in to offer me a glass of water, and I happily accepted, my throat dry from reciting grammar lessons. As she turned to leave, my eyes locked on to her round backside, enclosed today in a pair of gray leggings. I looked up for half a second—and in that moment, I saw that she was looking at me, an eyebrow raised. For a moment, I froze, certain that I would be fired and thrown out of the house. But Jenna said nothing, smirking and continuing out of the room, leaving me to finish my lesson with Elliott, scrunched into a ball of fear.
As I was preparing to leave, I pulled on my coat, preparing to bear the harsh cold on the way to the subway station. As I marched toward the door, I felt a hand, warm enough to burn through my coat, on my shoulder. I turned, finding Jenna there, smiling. But where her other smiles had been beaming and warm, this one was rich and mischievous, like she knew something that I didn't.
"It's so cold to be walking, isn't it?" she said. "Here, let me drive you."
There was fear in my heart, but I accepted, not wanting to walk in the frigid temperatures even despite my nervousness of being called out.
Jenna loaded me into her large minivan and sped towards the station, chatting idly about the difficulty of Elliott's school and all the great work I was doing with him. Hoping to keep things peaceable, I agreed, saying that he was a twelve year-old, not a PhD student, and shouldn't be assigned the work of one. That knowing smile appeared on her face, and as she turned back to the road, my eyes were drawn to her shirt, which was cut low and offered a delectable picture of her cleavage. For as alluring as I found her breasts, I hadn't noticed that when I came in—had she changed?
As we arrived at the station, she clicked on her hazard lights and puled onto the side of the road, then turned to me and looked expectantly.
"You've done so much for Elliott, and I appreciate it so much," she said, her full lips curling into a smile. "You deserve so much more than what I pay you."
My throat went dry. "Oh, no worries. He's a great kid, and I'm really happy to help."
"Well, I know I really appreciate it--it's not the easiest thing to stay interested in seventh grade English homework. I hope that our house is...stimulating enough for you."
Oh God. Was this really happening? The tent in my pants didn't want to ask questions, but before I could contemplate it further, I looked at the time and saw that it was 7:30--I was supposed to meet a friend at 8:00, and would miss it if I didn't leave then. I stammered an excuse and tumbled out of the car, leaving Jenna with the same smile on her face.
"Until next time," she said.
In fact, next time was that very weekend. Jenna said that Elliott had a major English test (that I, somehow, wasn't aware of). I had spent the nights since my last session emptying cum into my hand at the thought of Jenna, and I was eager to see her again, if only to get another peek at that ass of hers.
When I arrived on Saturday afternoon and rapped on the front door, Jenna answered me again, with a smirk that made my heart flutter.
"So glad you're here, Nick," she said. "We've been looking forward to this all week."
I grinned. "I can't imagine Elliott was too excited about studying."
"Well, maybe it was just me that was excited."
I took a moment to look her over. Though my furtive nocturnal fantasies had imagined her in a variety of glamorous outfits, from a garter belt set to an ultra-short dress, she appeared now, in reality, in a deceptively simple outfit—a low cut tanktop that exposed the tops of her breasts, and a pair of leggings that seemed worn, almost to the point of translucence. It wasn't until she turned around to lead me in that I realized how special they were: the leggings, already snug around her lithe form, were so stretched and worn with age that one could almost see through them—and in this case, I could see the neon pink thong squeezed over her ass. Though I didn't know for sure, Jenna seemed far too deliberate for that to be an accident. My cock stirred to life at the sight of it, and I wanted so badly to reach out and squeeze, but before I could even think seriously about doing that, Jenna caught my eye and grinned.
"I have a lot for you to look over today."
In fact, Elliott didn't have terribly much for me to do (how convenient). We went over his reading and the essay that we had worked on the other day, while, all the while, I continued to shudder at the thought that Jenna was just in the next room.
At the end of my hour there, Elliott scrambled off to the basement to play video games, and I took a moment to collect myself, thinking of what I would say, what I could say, to Jenna. But before I could begin my shadowboxing routine, I turned around and found her standing there, biting her lip like a nubile schoolgirl.
"He was great today," I blurted out.
"Well, he's only as good as his tutor." She waited for a response, but I only blushed and laughed.
Her wolffish smile only seemed to intensify. She turned to her purse, which lay on the nearby chair, and made a cursory, almost performative, search of its contents.
"Oh, shoot," she said. "I don't have enough cash on me. Must've forgotten to go to the ATM."
"Oh, that's okay," I said. "Next time is totally fine."
She stepped close to me, her voice dropping to a pur. "Or, I could try to dig up another form of payment. Want to help me look?"
I nodded meekly, and she, with a smile, turned and began to walk up the massive ornate staircase of the house—though my attention was less on the carved wood than on the sway of her ass and the way her neon pink panties clung to her skin.
We reached a room at the far end of the hallway, one that seemed rather far from any prying eyes or ears. She swung it open, allowing us to enter her massive bedroom, then quickly closed it behind her—and, with a click, it sounded as though she locked it. But before I could make any remark to this, she began another cursory rummage through her drawers, seeming to only move aside an item or two before turning back to me and biting her lip.
"Shoot," she said, stepping toward me. "I can't find any money. Is there some...other way I can pay you?" Her hand brushed over my cock, which, by this time, had made an engorged arch underneath my jeans.
