Teacher Surprise

Teacher Surprise

Summary: College student bumps into his high school teacher at a club and...

Note 1: This is a Halloween 2023 Contest Story so please vote.

Note 2: Thanks to Tex Beethoven for editing.

Teacher Surprise

A social club I'd joined recently had convinced me to go check out their home base... a college about three hundred miles away from the town where I'd grown up. And then the tour guide invited two other guys and me to meet him that evening at the Hot Wire, a nightclub a block away from campus. That night I got a blow job in a bathroom stall from a hot forty-something MILF wearing a wedding ring, and I finished the night with another woman in her SUV, where she fucked me with a child booster seat right next to me.

Which turned out to be the main focus of the club. On campus, it had a variety of nicknames: from Cougarville, to The Sure Thing, to the MILF Hut, to Pound City. I learned the Hot Wire was prime real estate for a plethora of MILFs looking for young dick.

Since I myself was a young dick (and never left home without it, yuck yuck), I learned quickly that unlike girls my own age, who were exhausting, expensive, and often just cock teases, older women didn't play those games. They wanted dick. They wanted to be fucked hard. They wanted a guy with enough stamina for a marathon fucking and multiple loads.

I also learned quickly that older women were sexually more experienced, much more willing to do kinky stuff, so they did a lot of the things those pretty coeds wouldn't do.

My first anal fuck? A brunette in her early fifties had me bend her over the couch in her house, where I could see photos of her four kids hanging on the walls.

First threesome? With two besties from Canada in the city for a conference. I fucked them and unloaded loads in each of them.

First facial? A large black woman in her sixties blew me and took my load all over her face... and even wilder... her early forties daughter was our lookout.

First prostate orgasm? With a wild tattooed Latina, who slid her finger in my ass while she deep-throated me, making me erupt in her mouth almost immediately.

First awkward husband encounter? I fucked a woman in her bed for a marathon fucking, stayed over, and she was riding me in the morning when her husband came into the bedroom. I was freaking out and about to run, when he asked me, as he grabbed some clothes from the closet, "I hope you're enjoying my wife?" I learned he'd been sleeping in the spare bedroom, just like he always did whenever she 'went on the prowl' (her words).

Anyway, those incidents lead us to my story.

It was Halloween, so we all made plans to go to the Hot Wire.

We all were a little geeky, and so we agreed to dress in various superhero costumes. I chose Spiderman, since I already owned the outfit.

We were there for about half an hour and two drinks in, when my mouth dropped wide open. In a slutty schoolgirl uniform with a skirt so short that her black thigh-high stockings were completely visible, was my high school English teacher from back home, Ms. Britch. I double and triple checked, since we were four hours away from my hometown. But there was no doubt it was her.

I should note that in high school before my MILF obsession, when I usually jerked off to the out-of-my-league cheerleaders, who paid no attention to me at all, I had a crush on a couple of my teachers... and one of them was Ms. Britch. She was sexy, always wore nylons, and was as sweet as pie. She was the reason for my nylon fetish, as was Mrs. Walker, my former math teacher. MILFs wore them way more often than girls my age did. And tonight, seeing her dressed so slutty, in thigh-high stockings, in a MILF club notorious for older women stalking young meat (and vice versa), instantly got my dick hard.

Questions like What was she doing here (both in this city and in this club... although being in this club dressed like she was, pretty much answered the question Why this club)?

I watched her interacting with a couple of other hot older women, and watched her dance to a couple of songs, as I finished my second drink.

Then I followed her to the bar, where she was waiting to order a drink. I noticed that her stockings had sexy seams down the back, and what looked like a Cuban heel. Then I said to Walter, the bartender, whom I was good friends with, "Another usual for me, and whatever this beautiful woman wants to drink."

Ms. Britch turned to me, and her eyes went wide.

"Hey, Ms. Britch," I greeted her warmly. "What can Walter get for you?"

"Joey?" she asked.

"Yep," I confirmed, even though she wasn't really asking, but processing.

"Ma'am, what can I get you?" Walter asked, the line beginning to get a little long.

"A rye and coke," she said, then added, "short."

"And two orgasm shots," I added, already on the attack.

"Joey!" she gasped a little nervously.

"Trust me," I said, the last couple of months making me way more confident and brazen, "they're delicious."

"You go to school here?" she asked, her British accent sounding so sexy.

"Yep," I nodded, "and I live at the dorm a few minutes from here."

"I see," she said, still processing my sudden surprise.

"What brings you to town?" I asked.

"A teachers' conference," she said. "I spoke at it today."

"What about?" I asked, keeping this casual, slyly trying to lower her guard.

"Assessment," she said, "it was rather boring."

Walter placed our shots on the bar.

I grabbed them both, handed her one, and said, "To serendipity."

"Serendipity?" she asked. I knew she knew the word, since we'd read a story in class all about it last year.

"Yes," I nodded, smiling.

"Okay, to serendipity," she agreed, and she downed the shot, as did I.

"Well, now I've given my favourite teacher an orgasm," I smiled, a line I'd used with fairly good success in the last couple of months.

She laughed, "Does that work?"

"Does what work?" I asked, feigning obliviousness.

"That line," she said.

"It has a pretty high success rate," I admitted, looking directly into her eyes.

"I see," she smiled. "Well, I'm impressed."

"You are?"

"Yes, you're a lot more confident than you were in high school."

"This place builds confidence," I said, as Walter placed our mixed drinks on the bar.

She grabbed her drink and took a big sip.

I said, "You look hot, Ms. Britch."

"Thanks," she said, looking down at her attire. "I never expected to meet someone I knew here."

"Me neither," I said, taking a sip of my drink.

"You can't tell anyone you saw me here," she cautioned me.

"Around here, I keep a lot of secrets," I assured.

"Good," she said, taking another sip.

Walter finished with a couple of ladies, and I said, "Two aphrodisiacs, Walter."

"Your shooter choices are a bit transparent," she smiled playfully.

"You knew I had a huge crush on you, right?" I asked, just throwing it out there.

"I knew you liked my legs in nylons."

"You knew?"

"Yeah, you were a little obvious."

"Did you ever wear thigh-high stockings like these ones under your much more decorous dresses and skirts?"

"Sometimes," she said, then leaned in and whispered into my ear, "or a garter belt with stockings."

"Here you go," Walter said, his timing a bit off this time.

She backed away, took the shot, and never breaking eye contact, downed it. "Mmmmmmmm," she purred, before she surprised me by taking the second shot and downing that one too. She then smiled, "I wonder if these will work."

"I hope so," I said, completely enamoured by this beautiful woman.

The two shots were perhaps her own liquid courage, since she asked bluntly, "So you must know why I'm here?"

"A conference," I replied a little densely.

"I mean you should know why I'm here... here," she said, pointing around, "in this specific establishment."

I could have joked about how she was likely the first person ever to call this bar an 'establishment', but sensing where this was going, I answered, eloquent and suave, "Oh. I can guess, but please tell me."

She leaned in very close to me, her hand went directly to my cock and gave it a firm squeeze, whereupon she gave me a facial expression that inferred she was impressed, "I came here to find some hot young stud to fuck. One such as yourself. Do you think you can handle me?"

"Y-y-yeah," I stammered, in awe of what was happening.

"I mean if you're down for it, I'm going to fuck you like you've never been fucked before," she said wickedly, her hand still on my dick as her lips tugged on my ear.

I was used to this direct approach, that's why women came here, but hearing those words coming from my hot high school English teacher, was a entirely different level of Wow!

"Tell me more," I said, worried I might burst in my pants.

"To be specific, I'm going to fuck the shit out of you," she said wickedly.

"You had me at fuck, "I joked.

"I'm staying at the Lux," she said, "room 312. Meet me there at 12:30. Right now, I need to say goodbye to my new girlfriends."

"I'll be there," I assured her, and she gave my dick one final squeeze, kissed me on the lips, and sauntered away, wiggling her pert ass.

I admired her backside until she disappeared into the dance crowd of costumes, before I finally adjusted my dick.

Walter the bartender said a minute later, "She's a real looker!"

"She was my high school English teacher," I said, still in a bit of a daze.

"Fuck off!"

"Yeah, and she just invited me to meet her in her hotel room."

"And you're going?" he said. In a way, it was a question, but also a statement meaning, 'You have to go!'

"Of course," I nodded, unable to believe my good fortune.

I had one more drink, and then I took a piss, where a chubby MILF in a not-very-flattering Jessica Rabbit costume was bent over the bathroom counter getting fucked by a cowboy while two other guys watched, and they were likely planning to do a train on her... public trains in a public bathroom being quite common here.

I then headed to the hotel. Usually when I was invited back to this hotel, I would be late, and sometimes not even show up at all, if a hotter MILF offered herself to me. By the way, for a hotel known for illicit sex, it was actually a nice place.

I went to the elevator, pressed the third floor button, and once the door was closed, I adjusted my dick. It was already hard with anticipation.

I got out on the third floor, went down the hall to room 312, and knocked.

A moment later my former teacher opened it, grabbed my hand, tugged me into the room, closed the door, and pushed me against it... before pressing her lips against mine.

We made out urgently and passionately for a couple minutes. Her hands roamed over my body, while I squeezed her ass.

She then dropped to her knees, pulled down my thin fabric of an excuse of clothing, and squeezed my dick through my underwear. "I've wanted this dick for some time."

"You have?"

"Mmhmmmmm," she affirmed. She pulled my underwear down as well, and my hard, seven-inch cock stood tall before my ex-teacher's eyes. "Teachers have naughty fantasies too."

She then took my cock in her mouth, while she stroked it.

"Oooooh, Ms. Britch," I moaned, in awe of who was sucking, me while I looked down at her.

"Isn't this nice?" she said as if we were sitting down to tea, in that sexy English accent that had always driven me wild.

"Oh yeah, Ms. Britch," I moaned again. "Suck my dick."

"You up for shooting multiple loads tonight?" she asked, looking up at me while stroking my dick.

"Oh yeah, definitely," I agreed, hoping for a marathon fuck session.

"Good. Because I'm going to fuck the shit out of you," she promised again, looking me right in the eyes, before sliding her tongue down my shaft and going to my balls.

"Yeah, you are," I agreed awkwardly. It was another interesting MILF quirk, where unlike girls, they often sucked on my balls... one of the reasons I manscaped regularly down there... and it made my dick look bigger.

"Oh yeah, I'm going to pound you so fucking good," she said wickedly, but choosing her words oddly, as if she were the man... before she sucked a ball into her mouth.

It seemed like semantics at the time, so I went with it, although I shifted the narrative slightly, "Oh yeah, I'm going to pound you so good!"

"I'm going to give you the fucking of your life," she promised, as she found and retrieved my other ball and replicated her tongue bathing and lip massaging, which felt damn good.

"I can't wait," I said, loving to hear such nasty things coming from the lips of a woman who'd taught me Shakespeare just a few months ago.

"Mmmmmmm, let's see this asshole now," she said, and she grabbed my hips, spun me around, spread my ass cheeks, and began eating my asshole... all in what felt like just a heartbeat of time.

"Ooooooh my," I moaned, my ex-teacher's tongue suddenly licking my asshole... which I hadn't ever experienced before, in my many kinky MILF adventures. It was shocking, especially when I looked down to see Ms. Britch between my ass cheeks, but it felt surprisingly pleasant... and made my dick pulse.

"Such a delicious asshole," she said, licking my hole up and down.

"Uh, thanks?"

"Nobody's ever eaten your asshole before?"

"No, never."

"That's a shame," she said, continuing to bathe my puckered hole with her tongue.

"So I'm learning," I said, at first thinking this would be gay, feel gay, but as she continued doing it, it didn't feel gay at all. This being a hot woman doing it, likely helped me accept that it wasn't gay. For the record, I have nothing against gay people, I'm just not one of them. I'm straight. I like women. I like pussy. I have no interest in dick. (On the other hand, I usually find the personalities of gay men more appealing than straight guys... a lot of times the latter have too many testosterone-driven dominance games going on.)

"Does this feel good, baby?"

"Yeah, it does," I admitted.

"You have such a pretty tight little asshole."

I wasn't sure how to respond to such a compliment... someone's butthole can be pretty?... but I did manage a soft moan, while she reached around and stroked my cock, while she kept eating my ass, "Thanks."

After another minute or so, she spun me back around, stuck my dick back in her mouth, and resumed giving me an amazing blow job.

"Oh, yeah! Suck it! Take it all!" I moaned, as she bobbed on my dick hungrily... easily deep throating me.

"Mmmmmmm," she moaned as she sucked.

I wasn't going to last much longer, so like a gentleman I warned her, "I'm going to come soon."

Like many MILFs I'd had the pleasure of receiving blow jobs from, she just kept sucking me, thus giving me nonverbal permission to come in her mouth.

But unlike all the other MILFs in my experience, she next reached around me and grasped my ass, gave both of my cheeks a firm squeeze, making my dick go even deeper into her mouth when she pulled me forward, and then before I had any time to realize what was happening, she stuck a finger inside my asshole. "Oooooooooh," I groaned, the sudden intrusion not painful, just weird.

She then finger fucked my ass, single-handedly spit-roasting me, without ever stopping her hungry cock sucking.

The intensity inside me multiplied in ways I couldn't explain. Her finger inside my asshole seemed to be connected to my dick, I was experiencing multiple pleasures, and in less than thirty seconds of having her finger in my ass, I came in her mouth.

I was overwhelmed... the intensity so strong, and so unlike any orgasm I'd ever experienced before... I didn't say a word as I filled her mouth with my load... which she easily swallowed, not slowing down at all. Her finger stopped moving, but it remained lodged in my ass, while my body continued trembling, with without a doubt the most intense orgasm I'd ever experienced!

A couple minutes later she pulled out her finger, stood up, and kissed me.

I was in a complete daze. I was used to aggressive women, even though most of the MILFs I fucked were utterly submissive... but this was a whole new level of kink!

I broke the kiss, and being aggressive too, I pulled her blouse apart... several cheap buttons flying every which way.

"Do you want to see your teacher's tits?" she asked. She wasn't wearing a bra.

They weren't large, but they were firm and shapely, her nipples hard and mouth-watering. I pushed her against the side wall and said, as I cupped them, "I've wanted to see... and to suck on... these tits for more than a year."

"Mmmmmmmm," she moaned, as I bent down and took her right nipple into my mouth. "That's it, suck on my nipples."

"Such perfect tits," I said, as I repeatedly switched from one to the other, bathing them with my saliva's wetness.

"I wish they were larger," she said.

"I don't. I think they're the perfect size for your perfect body," I disagreed agreeably, as I went to move my hand to her pussy.

"Not yet, big boy," she said, stopping my hand just a couple inches away from it. "Just focus on my tits for now."

"Okay," I agreed, bringing my hands back up to her chest. I was in no hurry to fuck her... I wanted this to be a lengthy marathon evening, so the more foreplay, the better.

So for a few more minutes I sucked on her nipples, cupped her breasts, and kissed her. Then I whispered in her ear, "It's time for me to repay your favour, Ms. Britch."

"Mmmmmmmm," she purred. "And what do you have in mind?"

Deciding to take control, I grabbed her hand, led her to the bed and said, "It's time for me to worship your entire body."

As we reached the bed, which only took a few seconds, she said, "I should warn you that I'm not like most other women."

"That's for sure," I smiled.

"No, I'm serious," she said, her tone shifting from sensual to no-nonsense in a heartbeat.

"Okay," I said, feeling a little thrown off my stride and confused.

She took my hand and carried it directly to her pussy... whereupon I immediately discovered it wasn't a pussy at all... but a very hard, big... dick!

My eyes went wide.

I was speechless.

She said. "I'll understand if you want to call a halt to our proceedings and flee."

Even with my hand on her dick, I couldn't fathom that Ms. Britch had a penis. A big penis. A hard penis!

I could have fled.

Perhaps I should have fled.

Yet I remained... in shock, bewilderment, and growing curiosity.

A moment later, I felt her hands on both of my shoulders, then a little pressure, and before I knew it, I was bending my knees and lowering myself to the floor.

I wasn't gay.

I'd never even once considered whether to suck a dick.

But as I found myself on my knees, and she lifted her plaid skirt to show me a bulging cock confined in a pair of pink panties, I felt my mouth watering and my cock flinching.

"Pull down my panties," she ordered.

"Yes ma'am," I said, and I brought my hands to her hips and pulled her panties down, my eyes focused on her dick as it flipped out and almost slapped me in the face.

She raised her stocking-clad feet to step out of her panties.

She then pushed her cock into my mouth, before I had any time to react or think. I was stunned to suddenly have a dick in my mouth.

She then said, "Suck my cock, Joey."

I could have refused.

I could have backed away.

I could have walked out.

But instead, I began ever-so-slowly to bob.

"Oh yeah, Joey. That's it, suck my cock," she moaned.

I was surprised by how natural sucking a dick felt. I couldn't explain why, but it actually felt good! My cock was throbbing while I sucked. No way would I ever suck another guy's cock, but since it was attached to a beautiful woman, it didn't seem gay at all. It just seemed right.