The Fall Semester


Usually I get about one per semester.  A crush, I mean.  This year it was a quiet boy again; an incredibly smart shy boy who sat in the back of my second period English class and didn’t seem to have many friends.  He wore a lot of black, and he clearly had no idea just how adorable he really was.  He had a really cute ass- nicely shaped and tight- the kind I could imagine spending many hours exploring.  His name was David.  I have to confess that I became a little bit obsessed with him that September.  You (or at least I) can’t NOT get crushes as a high school teacher; the trick is that you also can’t act on them.

He was fairly tall- probably not quite six feet, but lanky and awkward, not yet used to his height; and he seemed painfully shy.  His writing was incisive, and maybe even on the path to brilliant, but he hated speaking out in class.  I felt bad for him, and learned not to call on him, even though I knew that he would have had something interesting to say.  Sometimes though in class I would make eye contact with him, sitting in the back row, and sometimes he would blush.  Sometimes I would blush too, and get all tingly and squooshy inside.

David started to dominate my fantasy life; more often than not it was him- dressed all in black, shy and a little awkward, tentative but full of lust and oh so cute- that I pictured in my (embarrassingly frequent) masturbation sessions.  I started to get a little worried about myself.  I’d had crushes before, but never one this intense.  How old was David anyway?  He was a sophomore: that meant what fifteen, sixteen?  I looked up his age in the file; he had turned 16 in early September.  Wow, I could get fired just for thinking the kind of thoughts I’d been thinking!

Now and then, I got the distinct impression that the crush was mutual.  Sometimes I thought there was something in his eyes, his body language when he talked to me after class.  He often stopped by my desk after class to ask for help with his writing.  Not that he needed my help, not really; he was writing at an advanced college level already.  But I was happy to give him what help I could.  Once in a while I caught him looking at me with a kind of searching intensity in his eyes.  Those moments always made me blush furiously.  What was he thinking when he looked at me like that?

I knew however that I was fourteen years older than he was, and fourteen years is a lifetime to a sixteen year old.  A thirty year old woman is, if not actually on death’s door, practically a senior citizen.  And anyway, I’m overweight.  I mean I’ve lost a ton of weight since my high school and college days- I watch what I eat and I exercise, but I’m never going to be a skinny woman.  And boys, I’ve learned the hard way, don’t get crushes on fat girls.


September turned into October, which turned into November, and the days got shorter and darker.  It was Saturday, and I had a big day ahead- a ton of papers to grade, and then a friend of mine, another teacher, was hosting a dinner later on.  Hopefully I’d have time for some internet porn (my favorite guilty vice) and a few orgasms in between.

I was driving to the grocery store early that morning.  It was raining.  Not raining incredibly hard, but a steady soaking rain that kept me alternating my wipers between ‘intermittent’ and ‘low’.  I was distracted, listening to the NPR on the radio, thinking about the stack of essays waiting for me at home, going over my grocery list in my head, when I saw David trudging along the side of the road, without even an umbrella.  I almost didn’t recognize him.  I almost passed right by.  But I managed to pull over in time to roll down the window and offer him a ride.

He climbed into the car with a great big smile on his face that made my heart (and certain other parts) melt.  He was soaking wet.

“David, what are you doing out walking on such a wet morning?”

“Walking home from work.” was his succinct answer. He told me that he worked three or four nights a week at a convenience store.  That accounted for the dark circles under his eyes.  The poor kid must be exhausted.

“Could I offer you a ride home?”  I held my breath.

“Sure, that would be awesome.  Thanks so much for picking me up, Ms. T”

“Call me Jenn” I said, barely daring to breathe “Since we aren’t in school.” I ventured a smile.  God, I felt like a schoolgirl out on her first date.  His presence was like a nuclear reactor over there in the passenger seat.  I could feel the heat radiating off his core, threatening to send me into meltdown.

His house, where he told me he lived with his father, was about two miles away.  We drove mostly in silence; I felt tongue-tied and awkward; he seemed tense.  The closer we got to his place, the more nervous he seemed.  Finally we were there: a run-down shabby looking little house on a suburban block. I pulled into the empty driveway.

“Thanks for the ride, Ms…. Jenn…”

I can’t really explain what happened next.  There was an infinitely long, awkward pause as I waited for him to get out of the car.  I was holding my breath.  Somehow my hand found his.  Fingers intertwined.  One hand squeezed the other.  I leaned across, meeting him halfway.  Our lips met, and then we were kissing.  It started very tentatively- soft almost prudish pecks; it accelerated rapidly to full on tongue-wrestling.  He was a good kisser, and a fast learner.  I playfully bit his lip to see how he would react.  He bit me back, harder.  Good.  He planted soft butterfly kisses up and down my neck.  Very Good.  He nibbled my earlobe.  Very Very Good.

Throughout it all, our hands remained clasped together, each of us clinging to the other like a drowning person clutching at a rescuer.  I’m not sure how long we sat there in my car necking like, well, like teenagers.  It might have been ten minutes or half an hour.  At one point I opened my eyes (I am a confirmed closed-eye kisser) and saw his erect penis outlined clearly through the damp material of his black jeans.  He obviously wasn’t wearing any underwear.  I swear I could see every detail, down to the outline of his swollen glans.  My clitoris was in very much the same engorged condition.  Seeing his reaction to me only made my pussy drool even more.

Finally, we came to our mutual senses.  We had thoroughly steamed up the car windows.  We had steamed up my glasses.  He had to go.  I had to go.  He kissed me one more time, a sweet, lingering kiss on the lips, and then got out of the car and headed up the steps to his front door without a backward glance.  I watched that cute little ass in those wet black jeans until he closed the door behind him.

I didn’t make it to the grocery store.  I barely made it to the next block.  I pulled over, parking on the side of the road behind a grey SUV.  Wasting no time, I unbuttoned my pants, pulling them and my underwear down around my ankles.  The crotch of my panties was thoroughly soaked.  I lifted my heels up and rested them on the steering wheel, spreading my knees wide apart.  Parting my labia, I found my pussy exceptionally wet and slippery.  I couldn’t resist slipping a finger up inside, pretending that it was his finger exploring me.  But I couldn’t linger there.  My clit was calling.  Spreading my wetness generously up and down my slit, I started rubbing, strumming and grinding my over-excited clit.  I went off almost immediately, with an orgasm that shook my body, made me raise my ass up off the driver seat and didn’t seem to ever stop.  Just when the last spasms were receding, I realized that I was on the edge of coming all over again.  I reached down with my free hand and penetrated my asshole with the tip of one finger as I drew crazy tiny circles around my clit.  The second one was as just good as the first, and as I came, I pictured David’s beautiful cock, hard as steel and offered freely for me to do with as I wished.

In the end, I made it home, and even managed to finish grading my papers in between furious masturbation sessions.  By the time I drifted off to sleep that night, my clit was too tender to be touched.


I looked forward to my Monday morning English class with a mixture of dread and lustful anticipation.  There he was, in the back row, hot as ever, unwilling to meet my eyes, blushing whenever I looked his way.  I felt those eyes on me through the entire period.  The class seemed to last forever.

I had worn a skirt that day, a modest brown thing, and in a feckless moment that morning I had chosen not to wear any panties.  It was perhaps not the wisest choice.  From the moment he walked into the room, my pussy got wet, and for the entire class I was hyper aware of being naked under my skirt, of the moving air brushing against my pussy and of my labia rubbing against my clit as I moved.  It drove me crazy.

The bell rang, and the students filed out.  David, as usual, was one of the last headed out for the door.  I cleared my throat, tried to keep my voice level, and asked if I could speak to him for a moment.

He came over to my desk.  His proximity nearly drove me crazy.  More than anything in the world I wanted right then to get down on my knees, unbutton his jeans and suck his hard penis into my mouth.   But of course I couldn’t.

He spoke before I could say anything.

“Ms. T, I’m really sorry about Saturday.”

“Oh David, don’t be sorry.  Please don’t ever be sorry for that.  It’s just that we can’t…”

“I know.”

“It wouldn’t be appropriate.  We can’t…”

“I know.”

The next class was starting to come into the room.  “You’re beautiful David” I told him in a low voice “You should get a girlfriend your own age.”

“Thank you Ms. T.  You’re beautiful too” he whispered.

And then he was gone, and I had to teach a class.  Only I couldn’t concentrate.  He kept appearing in my minds eye, his voice in my ears.  Did he really think I was beautiful?  Me?

We didn’t speak again that week, but our eyes spoke volumes.  Whenever David was in my classroom, the sexual tension was almost unbearable.  All week, I felt like I was teaching second period English naked.  And I enjoyed that feeling.  Several times that week I had to lock myself in the faculty bathroom and masturbate just to get through the day.  Hardly professional behavior!

In class on Friday morning, I felt his eyes on me like two hot coals.  Did he have any idea at all how sexy he was?  Did he want me like I wanted him?  Had he ever masturbated to me?  He seemed to hesitate before leaving class at the end of the period, fussing with his papers at his desk after most of the other students had left, but then he seemed to change his mind, and left without a word.  I was relieved- for obvious reasons involving not getting fired- but at the same time I felt deeply disappointed.

I didn’t sleep well that night.  Erotic dreams, with stressful, anxious overtones haunted me all night.  I woke up early on Saturday morning, exhausted and physically turned on.  I couldn’t remember the exact details of the dream; they had evaporated as soon as I woke up, but my pussy was slick and drooling, and I’m pretty sure those details were downright perverted.

I looked at the clock.  It was only seven in the morning, and I was fully awake.  There was going to be no more sleep for me.  Running more or less on autopilot, I got dressed, brushed my teeth, got in the car, and drove over to the convenience store that David had told me he worked in.

I sat in the parking lot with the engine idling, working out just what I would say to him: –That I was incredibly attracted to him, but that nothing could ever happen between us. –That he was a beautiful young man and should get a girlfriend his own age.  –That I valued him as a student and someday as a good friend. –That…

I almost missed him as he walked out of the store, striding purposefully down the sidewalk.  I beeped my horn and waved frantically, like an idiot.  He stopped, turned, saw me, and his face lit up with the biggest smile.  Three seconds later he was in my car.

“Hey Ms. T!  It’s great to see you!  I kept thinking about you last night at work.”

All the things I had meant to say evaporated clean out of my head.  “It’s Jenn.” I said “Call me Jenn.  Don’t you get tired working overnights?”

“Yeah” he said “It totally sucks.  Sometimes I just feel like a zombie.  But I’m trying to save money.  I really need to get my own apartment.”

“You’re sixteen, right?” I asked, dumbly.

“Yeah.” He nodded.  “I think I’m old enough to take care of myself though.”

I risked a covert glance at his lap.  He seemed to be sporting quite the erection, and I was pretty sure that he was once again unencumbered by underwear.  For a second I was deliriously tempted to reach over, unzip his fly, and set that delicious sex-wand of his free.  But I didn’t.  “I couldn’t imagine living with my parents again” I said instead “When I was a teen I couldn’t wait to move out and live on my own.”

“No kidding,” he said “Living at home really sucks.” He sucked air through his teeth in a low whistle.

We had arrived at his house.  There was a battered old Toyota pick-up parked in the driveway.  I parked across the street.

There was a long, silent moment.  Our eyes met.  I leaned in to meet him as he leaned over to kiss me.  Our lips pressed together with an electric surge, then opened as our tongues teased and explored.  I felt his hand on my sweater.  Taking his hand in mine, I placed his hand on my rather small (but highly excited) breast.  He squeezed gently, and a thrill of excitement surged through my entire body.  He was an amazing kisser.  His hand stayed on my breast, strong and warm even through the various layers of fabric.  My own hand landed on his jean-clad thigh, stroking, petting, moving incessantly upward…

He broke off the kiss.  I was gasping with lust, practically ready to explode in my own panties.  “My dad’s home.” he said “we shouldn’t really be doing this here…”

“Yeah…” I said, more or less struck dumb.

“He’s not usually up this early, but…”

God I wanted him.

“Thanks again for the ride.”

And then he was gone, and I was alone in the car, alternately cursing myself for not stopping it before anything had happened and cursing myself for letting it stop at all.  At least this time I was able to drive myself home before I ripped my clothes off and masturbated like a hard-up nympho.  Which, I suppose I was.


In class Monday morning, David and I kept making sizzling eye contact.  I blushed every time our eyes met.  I was afraid that the rest of the class was going to pick up on our sexual energy.  That thought made me nervous and flustered.  I kept losing track of where I was in the lesson.  The class seemed to last forever, and by the time it was over I was exhausted.  And annoyingly horny.

That was just the start of a painfully long day.  Nothing seemed to go right all day.  Papers were overdue, students were late, announcements interrupted, meetings were held, glasses were misplaced and coffee got cold.  Even the weather was nasty.  It rained and blew all day, and several times the lights flickered as if the power was going to go out.  Finally, at four o’clock, I was cleaning off my desk, ready to go home where a good stiff drink and an (embarrassingly) large selection of sex toys awaited me.

There was a tap on the door.  It was David.  Shyly, he came into the classroom and approached my desk.

“Hi.” I tried to look up casually and gave him what I hoped was my best demure and most professional smile “What’s going on, David?”

“Oh…” he said “I missed my bus Ms. T.  I was wondering if you could give me a ride home.  I wouldn’t normally ask, but…” he gestured over to the window.  It was still pouring outside.  It had been raining hard all day, and showed no sign of letting up.

I didn’t feel comfortable giving him a ride in my car.  I didn’t want to be seen leaving the school with a student in my tow.  I didn’t know if I could control myself once I was in the car with him.  I didn’t know if I even wanted to control myself.  And of course I wasn’t about to make him walk home in this weather.

“No problem David.  I’ll just be a minute.”  I fumbled the file I was holding, and spilled 11th grade essays all over the carpet.

He seemed nervous once we were in my car.  I know I was.  We were both nearly silent.    It felt like we were on the edge of something big and dangerous.  It was scary, but exciting.  I didn’t know what was going to happen.

I thought about driving David directly to my place, dragging him into my bedroom, and ravishing his body there.  But I chickened out, making a left turn out of the school parking lot instead of a right.  David’s house was about six miles from the school, in the opposite direction from my apartment.

I pulled into the driveway.  It was dark already, and the rain was coming down harder than ever.  The wind whipped the trees along the street, sending the last few stray leaves swirling into the gutter.  No other car was parked at the house, and all the windows were dark.

“Thanks again for the ride… Jenn”

“Sure” I said.  “Any time.”  I paused “We really shouldn’t be doing this, you know?”

“I know.” He said “I wouldn’t have asked except for the rain.”

“Oh I don’t mind.  I really don’t mind at all.”  I smiled.  He smiled.  My heart melted. My pussy wasn’t far behind.

“Would you… would you like to come in for a minute?”

Oh YES I wanted to.

“No” I said “I don’t think that would be a very good idea at all.”  I smiled again and squeezed his hand “I’m not sure I could trust myself to behave.”  His hand squeezed mine tight.

And then, against all our combined better judgment, we were kissing.  It was more passionate, less tentative than it had been before.  I was aggressive with him, biting his lip, pressing my tongue deep into his mouth, guiding his hand to my sweater-clad breast.  I slipped my hand under his black t-shirt, feeling his soft skin, his smooth chest, rubbing then pinching then finally tugging and twisting on his hard little nipples.  He groaned out loud as I played with his boy titties.  It was too much for me.  Still locked in a hungry, open mouth kiss, I guided his hand underneath my sweater, under my blouse until only the sheer fabric of my bra separated him from my breast.  My nipple ached for his unrestricted touch.

I regretfully left his nipples, and went to work on the chore of unbuttoning his jeans.  The task was impossible to complete one-handed.  Even with two hands it wasn’t easy.  I had to break off our kiss and look at what I was doing.  His erection threatened to burst the seam of his pants.  Finally I got them open.  He lifted up his ass, and I pulled his jeans down around his ankles.

I had been right; he didn’t have any underwear on.  His penis stood straight up, pointing at the roof of my car.  It was harder than hard.  I could practically see it pulsating.  He had no pubic hair at all.  I guessed that he must shave or wax it.  It looked sexy.  I’d never seen a guy like that, so naked.  His cock was bigger than I had thought.  It looked delicious.

I hadn’t fooled around with a guy in a car in years.  In well over a decade, it occurred to me.  The windows were completely steamed up.  The rain had become more intense, and I could hear big fat drops spattering down on the roof of the car.  Some rational part of my mind told me that what I was doing qualified as a Very Bad Idea.

I dropped my head onto his lap and kissed his penis all over.  He was already leaking copious amounts of clear sticky pre-come.  I kissed very tenderly all over his sexy hairless balls.  Nudging his thighs apart, I kissed the tender flesh up behind his ball sac.  I relished his smell, his taste.  I wanted to eat him, I wanted to eat all of him.  He rolled over onto his side, raising his shoe-pant-and-sock entangled feet up onto the dashboard, giving me better access.  He was moaning out loud as I spread his muscular little buns apart, getting my first look at his beautiful tight crinkled anus.  My hand reached around, wrapping my fingers around his cock.  He was red hot.  I moved my hand in the tiniest little up and down motion, gripping his penis hard.  I stuck out my tongue to lick his sweet asshole.  I circled around his opening, teasing him (and myself) before zeroing in on his hole.  I loved how smooth he was back there.  I let the tip of my tongue drag across his opening.  I wanted to stick my tongue so far up his ass…

As soon as my tongue made contact with his anus, I felt his whole body go stiff.  His cock jerked in my hand.  He came with a long, throaty, drawn-out moan.

He squirted what seemed like a pint of come all over his belly.  Fortunately his t-shirt had ridden up during the action, so most of it ended up on the soft skin of his stomach.  It was kind of a pity, really- I had intended for him to come in my mouth- but I was way too excited to sweat the details.  Ravenously, I slurped up the salty, bitter puddle that extended from the end of his now softening (and extremely sensitive) penis all the way up to his belly button.  At last I came up for air.

“Was that ok?” I asked, a little abashed.

“Oh My God” was all he could manage to croak.  That was probably a good sign.

“I’m kind of a pervert” I hadn’t really meant to go the anal route with him.  At least not right away.  But then I hadn’t really meant for any of this to happen.

“That was amazing.” he said “I’m sorry I… came so quickly.”

“That’s OK” I smiled “But I think I need some attention now.”

It was only too true.  Ever since I had gone down on his ass, I had been on the very edge of a massive orgasm.  I hiked my denim skirt up onto my lap, and pulled my panties off over my shoes, cursing the steering wheel.

He only needed a little encouragement.  He was hesitant, afraid of hurting me maybe.  I helped his fingers find the entrance of my cunt, wide open and hot and drooling with lust.

“Is this alright?” he asked.  How sweet!  As if anything he did wouldn’t be alright with me.

“Yes! It’s very alright.  Please finger fuck me David.”

One of his fingers slipped straight up into my more than ready pussy.  It was quickly joined by a second digit, filling me deliciously.  “Move them in and out” I instructed him.  “Oh Yeah, like that.”

His fingers felt really good inside me.  Another finger started boldly probing between my ass cheeks, threatening to penetrate me.  I couldn’t stand any more teasing.  As his more and more confident fingers fucked me, I let my own finger find the red hot button of my clitoris.  I rubbed for all I was worth, and in two heartbeats I was coming all over his fingers, kissing him and calling his name over and over again.

His fingers were absolutely covered in my come.  Very endearingly, he licked them clean.  His young cock was already nice and hard again.  This time I would give him a proper blowjob.

My dirty thoughts were interrupted by the glare of headlights.

“Oh Crap!” he said, “That’s my Dad coming home.”

I started to panic, then felt stupid for it.  After all I was just a friend, who had given David a ride home on a stormy night.  Giggling, I tried to help as he struggled to get his jeans back up and buttoned. He gave me a quick goodnight kiss before going out into the rain.  As I backed out, his father, a stern looking bearded man, gave me a dirty look from the cab of his Toyota.  I didn’t care.  I was on top of the world.


David didn’t make it to school the next day, or on Wednesday.  That was very unusual for him, and it worried me.  In fact it knocked me right off the erotic cloud I had been riding ever since Monday night.  I started to worry that something bad had happened, and that I was my fault.  Could it be that having a (slightly) overweight thirty year old woman anally assault him in her car had traumatized him so badly that he had dropped out of school?

On Thursday, my fears were allayed when he showed up for class.  I was hugely relieved to see him at his desk in the back of the room, and though no words passed between us, I gave him a look that absolutely smoldered.

It was fifth period, and the school was having some sort of assembly for the football team, that was apparently going to state or something.  The whole school, staff and students, was supposed to be there, but I had weaseled out of it.  Midterms were coming up, and I was swamped in papers.  I was sitting behind my desk, wading through essays, when David walked into the classroom.

I gave him a sharp (well, not really very sharp at all) look through my glasses (I hate my glasses.  They make me look like- well, like a schoolteacher) “Shouldn’t you be at the assembly?”

“Yeah, I guess so.  Shouldn’t you be too?” he smiled shyly.

“Well I suppose I should be” I stifled a grin “David, I need to get some books out of the storage closet upstairs for my freshmen literature class.  As long as you’re skipping the pep rally, would you mind helping me?”

Ok, I admit it.  I had more than just fetching books on my mind.

I let the closet door swing closed behind us.  It locked itself with a click. I thought the odds were pretty damn good that we had at least twenty minutes of privacy before the assembly was over.  Instead of starting to collect the thirty copies of ‘The Grapes of Wrath’ that I needed for my next class, I went straight for the good stuff.  I pulled David to me and kissed him on the lips, flooding with relief (and lust) as he enthusiastically kissed me back.

“God I’ve missed you Ms. T”


“Hey, we’re in school now, right?” he gave me a naughty grin “I’ve been thinking about you constantly.  I can’t get you out of my head.”

“Mmm, me too.” We were clutching each other close, and the proximity of his parts to mine was driving me bananas “Where were you the last two days?  I’ve been worried.”

“Oh God.” He broke off the hug and took a step back, more or less falling into a folding chair that sat in front of the bookshelves “My Dad’s a real freak.  I should have told you before.  I’ve been locked in my room.  Grounded.”

“For what?”

“See, he’s really protective of me.  He doesn’t like for me to be um, he calls it ‘fraternizing’.  This is kind of embarrassing for me.”

“It’s ok” I said “Go on.”

“Are you sure you want to hear this?”

I nodded dumbly.

“Well, when I was thirteen, he caught me, um you know fooling around with another boy my age up in my room.  Ever since then he’s been really… strict with me.”

“Oh Sweety…”

“Yeah….  So on Monday he wanted to know who was in the car with me, and when I told him you were just a friend and had given me a ride home, he didn’t believe me.  He put me in ‘Lockdown’ and told me to pray for my soul.  I didn’t spend much time praying though.”

“You don’t have to put up with that David.  You’re practically an adult.  You can move out.”

“Yeah, I’ve been trying to save enough money to get my own place.  I can’t wait.”

“You could always come stay at my place” I blurted out.

He looked hard at me.  The intensity of his gaze was heart stopping. “Are you serious?”

I swallowed.  “Yes I’m serious.”  I could hardly breathe.

“I think that’s the most generous thing anyone’s ever said to me” he stood up and took my hands.  Feeling his skin touch mine sent shivers up and down my spine.  “You know we can’t do that.  I’m really crazy about you Jenn.  I really, um, like you a lot.  I don’t want you to get fired because of me.  Oh Crap, I shouldn’t even be in this closet with you.”

He was right, of course.  I could feel his breath on me, and it was driving me crazy.  “Here” I said, pulling out a scrap of paper and a pen “Here’s my phone number.  Call me if you ever need anything.  Or if you ever just want to talk.”

David thanked me, carefully folding the slip of paper up before sticking it in his wallet.

“We should probably get those books pulled out before the assembly’s over” I paused, then whispered in his ear “God I want you.”

“I want you too” he whispered back, then giggled softly “I’ve been crazy horny ever since…”  He was actually blushing!

“Well do you want to do something about that?” I asked “We don’t have much time” I looked at my watch.  We had a little more than five minutes before the passing bell rang and the assembly let out.

“What did you have in mind?”

Oh Boy.  Now I was the one who was blushing.  “Well…” I said “I thought maybe you could masturbate onto me…”

“Really?  Would you like that?”

“Yeah, a lot.”

He was already unbuttoning his jeans.  I got down on my knees, pulled my sweater over my head and unsnapped my bra, setting the little ladies free.  “Wow Jenn” he said “They’re beautiful.  I’ve never actually…”

“Just do it” I whispered throatily “We don’t have any time.  Come on David, put it all over my tits.”

He took his cock out, letting his pants fall around his ankles.  He was rock hard, pointing straight at me.  The fact that it was bald just made it look even bigger than it already was.  I’m no size queen, not by a long shot, but damn that looked good!  The head was bright purple, and freely oozing clear joy juice. He was clearly just as turned on as I was.

I love watching a man masturbate.  Actually, I love watching almost anyone masturbate.  But a really hot guy masturbating just for me, when I have a front row seat…. Heaven!  It didn’t take him very long.  He obviously knew how to handle his equipment.  It took less than a minute of his strong hand rapidly stroking his erection before he closed his eyes, arched his back and gasped, and I greedily watched as glob after glob of hot sticky semen jetted out onto my waiting boobs.  It was so incredibly erotic!  I reached out my finger, picking up the strand that threatened to drip out of his urethra and fall wasted to the floor, and licked it off.

“Oh My God” he said, his voice shaking “Can I?”

“Yes.”  Anything.

He got down on his knees in front of me and started licking the come up off my breasts.   Holy Shit, I was so turned on, I almost came just from that.  As he was cleaning my tits, the bell rang for the end of fifth period.  They would be dismissing the assembly now.

“Out.  Now.” I told him, groping for my bra.  He pulled up his pants, gave me a flavorful kiss, and slipped out into the hall moments before it became filled with noisy, bustling teenagers.  I got my sweater back on and collected the books I needed, making it back down to my classroom late, but not half as late as most of my students; painfully aware of my swollen clit, soaked panties, and the moist sticky skin of my breasts.  I don’t know how I ever made it through that class, but somehow I did.


I was sitting at home in front of the computer later on that evening, wearing nothing but a t-shirt, doing some pornographic research on my latest obsession: pretty girls anally assaulting their hotty boyfriends (um, did I mention that I’m a pervert?) when the phone rang.

It was David.


“Hi!  It’s great to hear your voice!”  I’d been secretly hoping that he would call.  The action on my computer screen was forgotten for the moment.  “Is everything ok?”

“Yeah, great!” his voice was low, I had to strain my ears to hear him “I’m calling from home.  I can’t talk very long.”

“That’s ok, I understand.  What’s up?”

“Um, first of all I wanted to let you know that you shouldn’t pick me up on Saturday morning.”  Damn, that had been precisely my plan “My Dad said he is going to pick me up from work and take me straight to a prayer meeting.”

“Ok, no problem.  Thanks for warning me.”

“I wanted to say, I really appreciate you giving me a ride.  Especially that first time.  You know, I haven’t really had a chance to really talk with you since… since all this started.”

I waited for him to go on.

“Um, the other thing is that I told my Dad I have to work on Sunday night.  I don’t have to work on Sunday night.”

The implications of that statement were already hitting me.  Like a truck full of sex.

“So…” long pause “I was wondering if you would like to hang out on Sunday night.  I can’t get out of my house until late.  I don’t usually leave for work till eleven-thirty.  I’d understand if that’s too late” he added.

“David, that would be so awesome!”  I was giddy.  Literally giddy.  My freaking head was spinning.

“Cool!” he sounded relieved, but nervous.  He was so CUTE! “So would you like to have dinner, or watch a movie or something?”

“Why don’t we just hang out at my place?” I said.  The implications of THAT went dripping along the phone line.  “I could pick you up at the end of your block.”

“That would be great!” he said “Listen, I have to go.  My father doesn’t know I’m on the phone.  I can’t wait though.”

“Cool” I said “Me too.  I’m really looking forward to it.”

I have to confess that as soon as I hung up the phone, I danced around my living room, spinning like a cheerleader.  He was going to be mine, all mine!  Then I was back in front of the computer screen with one hand on the mouse and the other between my legs.  Only the petite girls doing the butt-fucking were David, and their hot boyfriends were me.  And sometimes it was the other way around.

The next day seemed to last forever.  The following week was Thanksgiving, and all the students and teachers were restless.  It was midterm time, and everyone was trying to wrap up their midterm projects.  David and I didn’t interact at all that day.  We both knew that we were playing a very dangerous game.

During my prep period, the principal asked if I could drop by his office for a minute.  I was certain that I was busted.  My heart raced, my hands shook.  My instinct told me to walk out the door, get into my car and drive away and to just keep on driving.  Instead, I went meekly to Mr. Sander’s office.

He just wanted to see how my classes were going this fall, and to ask if I’d be interested in teaching a modern poetry class the next semester.  When I left his office, I was riding high on relief.

The weekend just crawled by.  I looked at porn, graded papers, and stared out the window at the naked, wind-torn trees.

I left early to meet him.  I was a nervous wreck.  The ‘What If’s were plaguing me.  The biggest ‘What If’ I didn’t even let myself think: What if he doesn’t show?

He was there, precisely at eleven-thirty.  He opened the car door, got in, kissed me on the lips.

“Are you hungry?” I asked

“No, I already had dinner.  Are you?”

No, I wasn’t hungry.  Not for food.

“Is it ok if we just hang out at my place?”  Is it ok if I just ravish your delicious young body?

“Sure” he said, lighting up the inside of my car with that charming smile of his “That sounds great.”

My apartment, like my salary, is modest, or to be more accurate plain small. I live in a one bedroom on the second floor of a complex near the train tracks: an apartment not unlike the one I lived in when I was in college, minus the roommates and the marijuana.  It is usually a terrible mess, but nervous energy had been spent that day doing a furious clean-up.

I pretty much dragged David up the stairs and into my den of iniquity, and right away introduced him to my futon couch.

We reveled in the sensation of freedom; unrestricted freedom to touch and kiss and roll around.  No one was going to walk in on us, no seatbelts or steering wheels to get in the way.  At one point we fell off the couch and onto the floor.  He landed on top of me.

His t-shirt had already come off, his pants were unbuttoned, and bulging precipitously.  He held my wrists pinned down to the carpet and kissed me fiercely.

“Oh David I want you so badly!” I managed to gasp when we stopped for a second to breathe.

“You know I’m a virgin, right?”

I smiled “Yeah, I had sort of figured that one out.”

“Is that ok?”

“David, haven’t you learned?  Everything about you is ok by me… What would you like to do now?”

He rolled off my body.  I could see the head of his cock peeking out from his unsnapped jeans.  “Well, um if its alright…”

“Anything David, anything.”

“I’d really like to see you naked.”

“Well then why don’t you undress me?”

I’m not very good at doing the dress up sexy thing.  After agonizing about it most of the afternoon, I had decided that it was best to just be myself: I had worn my favorite loose fitting faded blue jeans and a green tank top.  My only concession to sexy had been my favorite pair of red bikini panties that said in white cursive “It’s Not Going To Lick Itself”.

His hands were shaking a little as he pulled my clothes off, but for all that he didn’t seem to have much trouble.  It was a joy to watch his face as he undressed me.  He looked like a little kid at Christmastime. When he got to my panties, he grinned outright.

I raised my legs up in the air, and he pulled my panties off.  I felt momentarily self conscious about the triangle of light brown hair between my legs.  I wasn’t as bushy as those Penthouse models I had grown up with in the ‘70s, but weren’t all the girls shaving these day?  I hoped David, with his big bald cock, didn’t mind.

I probably shouldn’t have worried.  “Well, can I?” he asked

“Can you what?”

“Lick it?”

“David, you can do anything you want to me.  Anything at all.  But especially that.”

“Let me know if I’m not doing it right, ok?”

“You’ll do fine.  Just do one thing for me?”

“What’s that?”

“Take off your pants.”

He stripped out of his pants, releasing his proud, bobbing cock.  I took the opportunity to climb back up on the couch, spreading my legs wide apart for his eating pleasure.

Tentatively at first, then more confidently and aggressively, he started to lick my pussy.  Now I’m hardly celibate, but it had been several months since anyone had gone down on me.  David may have been new to it, but he was a naturally talented pussy-licker, and anything he lacked in technique, he made up for with enthusiasm.

“Jenn, you taste good!”  I loved seeing my wetness on his grinning face.

“Put a finger inside me.”

He was finger fucking me really good.  I was pretty much in heaven.  “Show me your clitoris.” he said from between my thighs

With two fingers, I pulled back the hood of my clit, fully exposing my happy button for him.  “Should I lick it?”

“Oh Yeah” I said “Mostly just around it, not directly on it.  It gets too sensitive.”

His busy tongue went back to work, lapping all around my clit, driving me crazy while his fingers slid in and out.  He was going to make me fucking come.  He was going to make me come all over his face.

“Play with my asshole” I burst out as I felt my orgasm start to rumble up from the tips of my toes.  Obligingly, he pressed a finger up against and just barely into my anus.  I exploded, grinding into him, riding the wave as my body shook through what seemed like the longest, most intense orgasm ever.

“Holy Shit!” I laughed out loud when I could at last speak again.

“That was amazing.” He was grinning ear to ear.

“You’re telling me” I said “So what would you like to do now?”

“What would you like to do?” he asked

“Honestly?  I’d like to suck your dick.  I want to give you a real blowjob.  And then, if it’s all right with you, I’d really like to fuck you.”

“That would be really amazing Jenn…” but I already had his cock in my mouth.

I’d been dying to eat that thing since… well, since he’d first walked into my classroom in September, but especially for the last couple of weeks.  It felt so good to have him in my mouth.  I thought I could happily suck him for hours and never get tired of it.  I’ve never been accused of giving a lax blowjob, but I really put everything into this one, swirling with my tongue, sucking hard, stroking him with my free hand; stopping and blowing on him whenever I felt him getting too excited.

“Oh Please Ms. T” he begged, rigid cock bobbing as I held my mouth just millimeters above the swollen purple head.

Very deliberately I ran one finger between my labia, getting it all slippery with my come.  I reached between his cheeks, searching for that special place.  It didn’t take me long to find it.  I worked the tip of my finger into his tight little hole.  “Is this ok?”

“Yeah…” he whispered “It feels… incredible.  Amazing.”

I pressed my finger a little further up inside him.  His body seemed to open up to welcome me.

“Do you want this?”

“Yeah… please…”  I pressed harder.  My finger slipped all the way up inside him, buried to the knuckle in his asshole.  He was super tight back there, clutching my index finger like a fist.

“I want you to come in my mouth” I told him, looking up into his eyes “Don’t hold back.  Don’t even think of holding back.”

I lowered my mouth back onto his cock, and sucked for all I was worth, bobbing my head up and down, letting his penis fill my mouth.  He responded instantly “Oh Jenn, I’m coming!”  I felt him come from the inside-out as his ass shuddered and clenched on my finger and he flooded my mouth with his semen.  He seemed to keep coming forever.  I hungrily drank every drop.  At last, his wet, diminished penis slid out of my mouth, and my finger slipped out of his butt.

“Oh thank you… thank you…” we kissed for a long time.

“Would you like to move to the bedroom?”  It was after one in the morning, way past my bedtime.  Not that I was sleepy.  Not at all.


I might not have been sleepy but David was.  I really couldn’t blame him at all; the poor kid had worked all night the night before, and had just been subjected to the most vigorous blowjob I had to offer.  We tumbled into bed together, snuggling and kissing and touching, but he kept drifting off.  Eventually he fell asleep on me, softly snoring, his hand on my breast.  He smelled good.  It felt so good just to have my skin pressing against his.  I quietly masturbated myself to an intense little orgasm as he lay sleeping next to me.  Then I drifted off into a dreamless sleep myself.

We woke together, with a start, at seven in the morning on Sunday.  Instantly we both had big grins on our faces, and we laughed to see each other’s happy face.  It felt so good to wake up together.  Then he saw the clock and the smile faded from his face.

“Oh Crap Ms. T- Jenn- I’ve got to get home.  I’m supposed to be getting off from work right now.”

Crap was right. “Do you think you might have time to lose your virginity?” he looked worried “I’ll drive you home.”

“I don’t know if I’ll be able to last very long…”

“Don’t worry about that!”

“I didn’t bring any condoms.  Do you have any?”

“I do.  But I don’t think we need to use one.  I’m on the pill.” I smiled “And I guarantee you I’m clean.”

“Ok” he said “I’m just worried… my dad would freak out if he suspected anything.”

“What are you waiting for then?” I asked as coyly as I knew how, and tossing the blanket in a rolled up heap off the bed.  “I’m ready for you!”  It was true; I’m one of those girls who gets wet at the merest thought of sex: at that moment I was Niagara falls.

David clambered on top of me, his extremely erect naked penis bobbing pleasantly.  I spread my legs wide for him, parting my labia with my fingers.  With my other hand, I helped guide him to my drooling entrance.

“Is this ok?” he asked hesitantly

“Fuck Me” I told him, pulling him down on me.  His penis slipped up inside me, filling me deliciously, like a hand filling a glove.  A smooth, sizeable hand in a hot, well oiled glove.

For a moment we just lay there breathing.  It felt wonderful to have him inside me, to have his cock in my cunt.  “Go ahead” I whispered “Fuck me.  Use me.  I want you to come inside me.”

He started moving in and out.  Oh it was delicious!  I wanted nothing more than to fuck him all day, every day.  “Go ahead” I encouraged him “Don’t be shy!  Fuck my cunt!”

He started humping me more vigorously.  The whole thing couldn’t have taken five minutes.  He was kissing me hard on the lips when he came, and I had my hands on his ass, pulling him deep into me.  I loved feeling him shudder, feeling his cock twitch, feeling the sudden rush of squishy heat inside my vagina, I loved feeling him go suddenly tense and then relax.

He kissed me again “Thank you, oh thank you Jenn!”

“Anytime, David” I said, meaning it.

“We should-“


His greatly reduced cock slipped easily out of my very slippery vagina.  At that point I would have liked nothing more than to make it nice and hard again.  But we had to get going.

David was already getting dressed.  “Does it bother you” he asked as he pulled his pants on “that I don’t have hair down there?”

“Oh no!” I said as I adjusted my bra “Actually I think it’s really sexy.”


“Really.”  I was buttoning my blouse.

“That’s funny.”

“Why’s that?”

“It’s my dad who makes me do it.  He’s made me shave ever since… He says pubic hair is dirty, sinful.”

I looked over at him, fully dressed now, strong and handsome and yet vulnerable.  “You’ve got to get out of that house,” I told him

“I know.” he said.

I drove him back to his house.  The drive was practically silent.  We held hands the whole way.  The beat up Toyota was nowhere to be seen.  David kissed me very sweetly on the lips before getting out of the car and hurrying up the steps to his house.  I pulled away, driving distractedly back home.  His come was still inside me, leaking out of my pussy and soaking through my panties.  I couldn’t wait to get back home and to rub his wetness all over myself.  I couldn’t wait to get him alone again.


David wasn’t in class again on Monday.  Immediately, I feared the worst.  The most frustrating thing was that there wasn’t anything I could do.  I just had to wait and hope.

The day seemed to last forever.  As soon as school let out, I went home, hoping that he’d call me.  The phone remained obstinately silent.  Time slowed down to a crawl.

I didn’t want to stay and I didn’t want to leave.  It was exhausting.  I ordered a pizza.  I tried to correct papers, but I couldn’t concentrate.  I tried going to bed early, but I couldn’t sleep.  Finally, at eleven o’clock, I got up and opened a beer and slipped a dvd into the drive.  If anything would make me sleep it was alcohol and an orgasm.

I hadn’t been watching the movie that long- my sweatpants were down around my ankles and my beer was still three quarters full- when there was a soft tap at my door.  I sort of panicked, pulling up my pants, shutting down the sound and pausing the movie in the midst of some of the raunchiest action.  I didn’t dare hope that it was him.

I flung the door wide open.  It was him.  The lust that had been building up inside my body as I watched the pornography on the lcd screen instantly melted away.  He looked terrible.  He had a black eye and the side of his face was all puffy and swollen.  Trying not to burst out in tears, I pulled him into my apartment where he stood, blinking.

“I’m sorry” he said “I should have called first.”

“No no, don’t worry about that.  What happened?  Are you alright?”

“My dad went to pick me up from work on Sunday morning…”

Oh No.

“He got really mad.  He wanted to know where I’d been.  When I wouldn’t tell him, he only got madder.”

Oh David

“When he was done with me, he locked me in my room.  He… threatened to really hurt me.  I’m scared of him.   I think he’s crazy.  So I jumped out the window.   I didn’t know what else to do but come here.”

“You did the right thing David” I hugged him close to me.  We held each other for a long time.  I realized that he was crying.  I realized that I was too.

I got him out of his clothes and into the shower.  He seemed a little embarrassed to be naked in his current state.  He had a nasty collection of scratches and bruises- he said he fell through a bunch of tree branches when he jumped out his second story window- and there were ugly red welts across his ass, thighs, and lower back.  But it didn’t seem like there was any permanent damage done, and when he got out of the shower, wrapped modestly in a towel, he looked a world better.

“I can’t go back there” he said simply.

“You don’t have to” I said “You don’t ever have to go back there.  You can stay here until we get you your own apartment.  It’ll be ok.  You’re going to be alright.”

“Thank you Jenn” he said.

“Think nothing of it” I replied “There’s benefits for me too” I ventured a little smile “Can I get you some hot tea?”

“That would be great” he said, still standing in the middle of the room “I’m exhausted.”

I stepped into the kitchenette and put water on for tea.  Soon I had two cups steeping with herbal tea and honey.  That made two of us who were exhausted.  I was so glad that he was alright, so glad that he was here and safe in my apartment.  I carried the two steaming mugs back into the living room.

I was mortified.  David was standing with his back to me, watching the computer screen.  The movie that I had paused before was playing again with the sound still turned down.  The pretty girl (prettier and slimmer and younger than me) was still butt-fucking her sexy boyfriend with her big blue strap on dildo, and he was still loving it.

David must have heard me.  He turned around.  “Do you think that’s hot?  Do you think that’s sexy?”

Oh My God, I felt terrible.  Dirty.  I’d never told anybody about my porn habit.  Porn isn’t for girls, it’s for guys, or at least that was what I’d learned growing up.  Oh, he’d have found out eventually.  But I really hadn’t wanted it to be tonight.  And I hadn’t wanted it to be that particular movie.

“Yes” I said miserably “I think that’s really hot.  Sexy.”

“Really?” he asked “Me Too.”

“Are you serious?”  The girl on the screen had her boyfriend on his back and she was sliding her silicone cock in and out of his asshole while she fondled his very erect dick.  He was loving it.  I knew (from prior viewings) that he was about to spurt all over his stomach and that this would set her off, moaning and groaning and grinding herself onto the base of the strap-on; and this was usually when I timed my own orgasm to occur.

“Would you do that to me?” he asked.  His right eye was still black and swollen, and the right side of his face was still puffy, but he looked miles better than he had when he had walked in my door.

“Only if you wanted me to.”

“And what if I wanted you to?”

I looked hard at him.  “Are you serious?

“Are you?”  The girl on the computer screen was coming, a real orgasm as far as I could tell, breasts flushed and bouncing, grinding herself deep into her already spent boyfriend.

“I’ve got one of those things” a strap-on harness I meant “But I’ve never actually used it.”

“So… do you wanna…?”

Oh My, YES I did!

We ran- yes, ran- into the bedroom.  The pink towel had fallen from David’s waist, revealing him in his beautiful nude state.  His smooth cock was already hard.  I couldn’t believe this was happening to me.  I fished out the harness from the bottom drawer where I kept my toys.

“Is that really going to fit?” he asked, eyes a little wide.

“Well we’ll see,” I said as I fumbled with the straps, feeling faintly ridiculous, “We’ll make it real slippery and I’ll be really gentle.”

His dick was really really hard.  I had him get on his hands and knees on my bed.  He looked incredibly hot, incredibly lewd like that; ass thrust up in the air, cock pointed straight down at the bed.  I could feel my own joy juice running down my thighs.

“Is this normal?” he asked me.

“No, I don’t really think it’s very normal,” I said, “But I think it’s really hot.”

“Me too!” he said, wiggling his bottom invitingly.  I clambered up onto the bed, my fake dong wagging comically.  There were angry red stripes across his pale ass cheeks from where his dad had beat him which looked both sad and disturbing, and disturbingly sexy.  I parted his ass cheeks with one hand and stuck my tongue deep into his dark male nether region.

I loved licking his ass, and I loved the reaction I got.  With my hand wrapped around his throbbing dick, I stuck my tongue as far as I could get it up his asshole.  He moaned and wiggled.  His cock was drooling precome.  I licked his dangling balls, licked is asshole, licked his crack, licked all over him.  His anus was winking with desire, and I didn’t think I could stand to wait one second longer.  I inserted one wet forefinger.  He was super tight.  His asshole clutched my finger the way a 2-year old clutches your hand when you help her walk downstairs.  “Oh My God Ms. T!  That feels so good!”

I let my finger slide out with a little pop.  “I want to fuck you David.”


I smeared lube generously all over my purple cock.  It suddenly seemed outrageously big.  I had had it up my own ass (of course, I AM a pervert after all!), and it stood to reason that David’s butt was at least as accommodating as mine, but his little butthole looked so tiny and vulnerable.  I vowed to stop the moment he seemed to experience any discomfort.

“Please…” he repeated.  He was spreading his own butt cheeks apart for me.  I positioned myself behind him, running my slippery dick up and down his wet crack.  “Please…”

Carefully, very carefully I aimed the head of my realistically shaped dildo at his puckered hole.  I nudged forward experimentally.  He moaned and pushed back at me.  His asshole opened up and swallowed the end of my dick.  I was in heaven!

“More!” he groaned through gritted teeth, “Fuck me more.”  I carefully pushed a little more into him “Oh Jenn it’s so good.  I love you fucking my ass!”

Every time I thrust forward, the base of the dildo bumped against my super-engorged clit, sending a shockwave right through me.  Every time I thrust forward, the dildo slipped a little bit further up inside his teen-age body.  Eventually my pubes were pressed right up against his tight little ass.

“Fuck Jenn!  Oh Ms T!  I think you’re gonna make me come!   Fuck me harder, please fuck me!”

I obliged him.  I was SO right on the edge of my own humongous orgasm.  I wrapped one hand around his dick, grabbed a fistful of his hair, and started humping him as hard as I could.  My thighs protested, but it was totally worth it!  He was screaming, I was pretty sure with pleasure, but to tell you the truth at that moment I didn’t really care because I was busy coming all over his fine fine ass.

We were both glowing when I finally gently extracted the dildo.  He had shot come all the way up to his chin!  As soon as I had the harness off, he rolled me onto my back, climbed between my legs, and licked me to another delicious orgasm.  After that he was hard again (being sixteen and all), and I sucked his dick until he came in my mouth. After that, we slept together, long and hard and peacefully, cuddled up like spoons.


Our story didn’t end there of course, although that seems like a pretty good place for me to leave it.  I helped David find an apartment and a better job, and he graduated from high school and went on to college and then grad school and then a career as a journalist.  We were lovers for a while, and then we weren’t for a while, and then we were kind of lovers again, and then we were just friends.  Friends who sometimes fucked like crazed weasels.

I had it out with David’s dad.  It was a Saturday, and I was helping David move his stuff (what little he had, he didn’t really own very much stuff) into his new apartment.  I had sent David out with my car to get some kitchen and bathroom stuff, when I saw the beat-up primer-gray Toyota pickup pull into the apartment complex and park by the pool.

I screwed up all my courage, and walked straight up to the bearded little man who got out of the truck.  “You must be David’s father?”

He was spitting with rage.  He called me a bitch, a whore, a Jezebel and a temptress.  He demanded I ‘render the boy from thy filthy clutches’.  I’m not kidding.  It was scary, but it was also surreal, and I had to fight back the urge to laugh in his face.

When he paused to catch his breath, it was my turn.  Turning on my pest parent-teacher-conference voice, I told him that if I ever saw David again, I wouldn’t hesitate to shoot him.  I told him that as a feminist and a modern woman, I carried a handgun with me at all times and that I knew how to use it.  (Lies, outright lies.)  I told him to get back in his truck before the cops showed up.  I told him that I knew what he had been doing to David, and that if he didn’t want the police called on him, he’d better get his skinny ass back in the truck.

My bluff worked.  Seething with rage and shame, he slunk back into the truck and drove away.  We never saw him again: I guess he just wrote David off as a hopeless sinner.  I was afraid he might get the school board or the police involved, but I guess that just wasn’t his style.  I drove by the house a few weeks later and it looked abandoned.

I didn’t tell David that his Dad had come by, but I did let him fuck me up the ass, probably damning him to another eternity in hell in the process.  But I sure enjoyed it, and I didn’t hear any complaining from David.

Sometime in January, David started dating a girl in his class, which made me a little sad, but happy for him too.  And anyway, it was a new semester, and I had a new crush.  This time it was a plump little girl named Emily who sat in the front row of my Modern Poetry class.

1 Comment »

  1. ROJ said

    This was a well written story…Now why couldn’t I have found an English teacher like this…le sigh, LOL.

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