Accidental Upskirt
by Ashley
Copyright© 2026 by Ashley
Erotica Sex Story: Jimmy and his math teacher collide on the stairs one day. As he's picking up the papers that she drops, he accidentally catches a glimpse up her skirt. While he's still reeling over what he sees up there, she rushes off, leaving him to spend the rest of the day panicking over how to play it when he sees her in class. In the end, he decides to deny everything, but Miss Coombe doesn't seem to want to let it go that easily.
Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa Consensual Heterosexual Fiction Anal Sex First Masturbation Oral Sex Petting Sex Toys Teacher/Student .
So, my name is Jimmy, and if pushed, I’d have to admit that I was a pretty average seventeen-year-old virgin. Average looks, average height, average weight, average intelligence. I was even possibly only averagely horny; I beat off a lot, but I suspect that most other guys my age did too. I’d had a few girlfriends, but I suspected that I was too nice, or they were too nice, or most probably a bit of both, so although we had fun, we never actually ... did it.
That all changed due to a moment of clumsiness on my part.
I was late getting to class after I’d had to go to the bathroom. Coming up the stairs, I met Miss Coombe on her way down. We did that sort of dance where you both go the same way, half smile at each other, and then do it again. On the third attempt, we collided, knocking some of the papers out of her arms. Apologizing profusely, I knelt down to pick them up. As I did, she lifted her foot, which had ended up on top of one of them, and moved it to the side. This had the effect of spreading her legs a few feet apart, and I became aware that I could see a little way up her knee-length, pleated skirt.
That was the point at which time seemed to slow to a crawl. Leaning forward just slightly and turning my head, I found that I could see straight up her skirt. The first thing that I noticed was that what I’d assumed were tights were, in fact, stockings. Above those were a pair of creamy-colored thighs, and between those was ... nothing! Not literally nothing, but no panties and no pubic hair! I had a perfect view of her perfect pussy! I’d never seen one IRL, and the soft mounds separated by rosy-pink lips took my breath away. But, astonishingly, there was something that dragged my eyes away from even that: between her beautifully rounded butt cheeks was a jewel. I’m not getting all poetic about her butthole; there was a red, heart-shaped, sparkling jewel nestling in her crevice. Miss Coombe, my prim math teacher, was going commando, was bald as a baby girl, and had a butt plug in her ass!!
It could only have taken a few heartbeats for me to take that all in, at which point Miss Coombe squealed, pushed her skirt between her legs with one hand, snatched the papers from me with the other, and hurried away. I knelt there, speechless and fully erect for maybe twenty seconds as my brain tried to process what I’d just seen. I was jolted out of it by the bell sounding for the next period, and I got up and stumbled my way to my class in a daze.
That was the first lesson of the afternoon, and Miss Coombe’s was the last. She must have known what I’d seen, and I spent most of the afternoon trying to plan how to play it when I saw her. In the end, I concluded that all I could do was to try not to make eye contact, and, if she challenged me, to pretend that I hadn’t seen anything.
It seemed to be working just fine until the final bell went, and she told the class to pack up and leave. My heart was just beginning to settle, and I was halfway to the door, when she said, “James Russell, could you stay behind, please?”
Suddenly, my heart was hammering in my chest, and thoughts were racing through my mind. It wasn’t fair! She couldn’t punish me! It hadn’t been my fault! I hadn’t meant to look up her skirt!
But strangely, she didn’t look angry as I stood before her desk; if anything, I thought she looked as frightened as I felt.
“James,” she said softly, “or is it Jimmy?”
“Jimmy,” I mumbled into my chest.
“I think we need to talk ... but not here,” she said, and then handed me a small piece of paper. I looked at it, and it was an address. I recognised it as a street about a mile away. “I believe that it’s almost on your way home ... if that’s OK?”
I was confused, but it wasn’t a detention or having to see the head. “Yes, sure,” I agreed, hugely relieved.
On my way to my bike, I was wondering what was going to happen. Just in case, I rang Mom to tell her that I might be a bit late. She wanted to know why, so I improvised, “I’m getting a little extra tutoring in math,” I explained. I thought it was genius: if anyone saw me at Miss Coombe’s house, it would explain everything. And it wasn’t as if I didn’t struggle with the subject. Mom seemed happy with that, and I cycled fairly slowly to the address that I’d been given. I leaned my bike against a hedge and then took a deep breath and rang the bell.
Before I continue, let me describe Miss Coombe as I knew her up until that day. She wore no makeup, her hair was palest blonde, almost gray, and always pulled severely back and up in a bun. She tended to wear baggy cardigans and thick woollen pleated skirts that came to just below the knee. She certainly wasn’t fat, but her clothes gave little idea of what was under them. If asked to guess her age, I would have said anywhere between thirty and forty-five.
When I knocked on the door and saw the woman who answered it, I had to check that I’d gotten the right house number. The woman who stood before me had her platinum blonde hair cascading in soft waves down to her shoulders, a slash of bright-red lipstick accentuated a sensuous mouth, and she was wearing a silk kimono, the same color as the lipstick, that clung to her perfect breasts and clearly erect nipples like a second skin, and came maybe a third of the way down her shapely thighs. She was gorgeous.
“Jimmy,” she said softly, dispelling any lingering doubts that I might have had about being at the wrong house. “Please come in.”
We stood in her lounge, facing each other. “Miss Coombe--” I said, trying to begin the little speech of apology that I’d come up with on the way.
“Tricia,” she interrupted.
“Tricia--” I began again, but she held a hand up to stop me again.
“We both know what you saw earlier, Jimmy,” she said. “I know I shouldn’t do it, but it brightens my day. Do you have any idea how boring it is, teaching the same thing, year after year?”
I shook my head and tried to look sympathetic.
“So, what’s it going to take for you not to tell anyone?”
I almost laughed. “Tricia, I’d--”
I was going to say, ‘never tell anyone’, but she spoke over me, “Do you want to see me completely naked?” The words died on my lips, and I stood there, my mouth opening and closing silently. “More?” she asked, “A blowjob?”
My poor brain was fizzing, and before I could even think how to reply, she undid the sash and let the robe fall off over her shoulders and onto the floor.
I literally whimpered at the sight of her wonderful body: her high, pert, upturned breasts, with fat, long nipples, narrow waist with flaring hips, long, slender legs, and, of course, her bald, luscious pussy.
In seconds, I was so hard that my cock was bending uncomfortably in my briefs. She looked down at my groin, and her lips curled just slightly at the edges. “I see,” she said, coming over to me and kneeling in front of me.
As she began to undo my pants, my heart was pounding, and my head was spinning. Miss Coombe, no, Tricia, this gorgeous woman, was going to suck my cock! Me! Jimmy Russell! She pulled my pants down to my knees and then ran a fingertip along my shaft through my underwear, making it twitch and me gasp, before putting her fingers in the waistband and drawing them down as well.
She was looking at my erect cock with every sign of pleasure. “Perfect,” she said, so quietly that I thought maybe I wasn’t supposed to hear. ‘Perfect?’, what the fuck did that mean? Before I could even begin to think about that, she looked up into my eyes and then covered my knob with those wicked red lips of hers.
I could feel her running her tongue around my tip as she bobbed her head up and down, sucking away. With one hand, she was pumping up and down on the base of my shaft, while the other was caressing my balls. It was insanely wonderful, and my legs began to tremble as I very rapidly approached a climax.
“Miss Coombe ... erm, sorry, Tricia,” I groaned, having the idea from somewhere that it was polite to give a girl a little warning. But her eyes just seemed to smile up at me while her lips tightened and her hand moved faster.
I’d never had an orgasm like it, and she just kept sucking and licking as my hips jerked, swallowing what seemed like gallons of my cum. And still she didn’t stop, and my legs began to spasm wildly as my knob entered that super-sensitive post-orgasm phase. It was exquisite torture for maybe two or three minutes before I began to get hard again, and then it was heavenly all over again.
When she seemed happy that I was fully erect, she took her mouth from me. “Is that enough to buy your silence?” she asked.
“I-I-I--” I stammered, overcome with gratitude to this amazing creature.
“Am I going to have to let you fuck me?” she asked, sounding sad even though her eyes were sparkling.
I’d never, ever had any intention of telling a soul about her ... indiscretions, but how could I turn down an offer like that? I nodded hopefully.
“Oh dear,” she said sorrowfully, standing up and turning away from me. Her ass was a work of pure art: beautifully curved, so firm and yet soft-looking, and, as she walked over to a chair, the cheeks moved in such a way as to make my already hard cock crank up several more notches.
She bent over the back of the chair, parting her legs widely, which displayed the toy in her asshole. “Do what you must, young man,” she said, sounding resigned, but her pussy was clearly very, very wet.
I moved a little closer, and my eyes roamed over the beautiful curves of her ass, and the plump mounds and shiny lips of her pussy. ‘Do what you must,’ she’d said - did that mean anything? Did that mean that I could touch her? I reached out a trembling hand and stroked her right cheek, fully expecting her to whip around and slap me in the face or something. But she didn’t. I thought that maybe I heard a soft moan, but it did seem that I was allowed to touch her!
With my other hand, I began to stroke the other cheek as well. The skin of her butt felt incredible in my hands - stunningly soft and smooth and warm, and I adored it, squeezing and fondling her firm flesh. This time, I was sure I heard her moan, and she began to move under my hands, pressing herself into them.
My cock was so fucking hard that it hurt, but I ignored it - I wanted to touch her pussy! Each circular motion of my hands got a little closer to the gap between her thighs, and again I was half expecting her to object, but the moment that my fingers brushed against her wet lips, she opened her legs wider. “Oh, no,” she groaned, “You’re going to finger me before you fuck me, aren’t you?”
I was so confused: what she was saying bore no relation to the way she was acting. But I was too excited to even think about stopping, and my fingers explored the silky folds of her pussy, smearing her juices all over the soft cushions of her mound. Then she thrust her hips back at my hand, and two of my fingers slid inside a hot, pulsating tunnel. I had my fingers in her pussy!
“Is there no end to the indignities you’ll put me through?” she wailed, but at the same time, she was rocking her hips, forcing my fingers ever deeper.
“Tricia--” I began, wanting to try to make her understand.
“No, no,” she interrupted. “Let’s just get this over with.” And she reached one hand behind her back and fumbled for the zipper on my pants. As soon as she got it down, she reached inside and dragged my briefs to the side so that she could wrap her hand around my erection. Having her touch me was incredibly exciting, but being only half out of my fly and my briefs was really uncomfortable. Reluctantly, I stopped groping her so that I could push my clothes down to my knees.
“So hard,” she whimpered, her hands now all over me, pulling my cock toward her as she played with my balls. I kind of shuffled forward until she was rubbing my knob up and down her wet slit. The softness of her lips on the tip of my cock felt sensational, and then it slipped inside her, and I groaned out loud because her hot, wet pussy felt like absolute heaven.
“Go on then, take me,” she said pitifully as her hand released my cock. “I’m just your plaything, and there’s nothing I can do to stop you.”
Her words were confusing, but nothing on earth could have stopped me from thrusting my hips forward and burying my cock in her sweet pussy until her gorgeous ass cheeks pressed against my thighs, and then pulling out to do it again and again.
“No,” she cried, thrusting her hips back to meet each of my thrusts so that our bodies met with a slap. She flailed a hand behind her until she found one of mine, and then dragged it forward and pressed it to her breast. It was wonderfully soft and surprisingly heavy, and she groaned as I squeezed and caressed it, falling across her back and reaching around with my other hand to grope the other one as well.
“You cruel, cruel boy,” she moaned, but still managed to grab my ass with one hand and urge me to fuck her even faster. I was almost delirious with happiness: I had Miss Coombe’s tits in my hands, and I was fucking her incredible pussy for all I was worth! Me, no-longer-virgin Jimmy fucking Russell!
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