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My Earliest Fantasy

Category: Mature
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I grew up in Charleston SC. My mother and my father had divorced when I was 12. Mom met my stepfather, and moved my sister and I to Charleston after they were married. It’s a nice place, but I digress…

Ms. Wells was probably the toughest teacher at my high school. She was very demanding and accepted nothing less than 100% from her students. The problem I had was that school always came easy for me. Not much of a challenge, if you know what I mean. For most teachers, that was enough. Not for Ms. Wells though.

Ms. Wells hadn’t been out of college long. She probably was no more than 27 or 28 years old. And while she had the reputation of being a hard teacher, she was also easily the most attractive. She usually wore loose fitting sweaters and ankle length dresses. But at 18, all you did was wonder what was under those clothes.

Ms. Wells quickly found out that I was sand bagging, and not taking her English class as seriously as I should. Although my grades were fine, she knew I was not applying myself 100%. She tried putting more pressure on me to apply myself. Not only with after class discussions, but also putting me on the spot in front of the class with questions that the average student probably wouldn’t know. I think that was the breaking point.

I mean come on, I had a reputation at school. I was a jock, not a bookworm. I couldn’t simply answer her questions in front of my peers, with out facing ridicule in front of them later… could I? So I made jokes. Disrupted class. And was your basic stereotypical jock asshole.

And that was all that Ms. Wells needed.

Now I lived in a middle upper class neighborhood, and I had absolutely NO idea that Ms Wells lived 6 or 7 houses down from me.

So imagine my shock when on a Saturday afternoon while out raking the yard, Ms. Wells turns into my driveway.

“Chris, are you parents home?” She asked, as she cut the engine and stepped from her car.

“Uhhh… yes mam,” I manage to stammer out.

“Great, I think its about time I had a talk with Mr. and Mrs. White”.

“Ummm … sure,” I manage to mumble as I dropped the rake and guided her toward the garage. “Mind if I ask how you knew where I lived Ms Wells?”

Glancing back at me with a stern look, she stopped. “I didn’t know until 5 minutes ago. You see that newer house on the other side of the street?” she asked pointing.

“Yes mam”.

“I moved in in July,” she said as she whirled back around and headed for the garage door.

Now let me tell you… My Mom didn’t fuck around when it came to school. So she was none to thrilled to have her sons English teacher show up at her house on a Saturday afternoon.

I introduced Ms. Wells to my parents. Turning back to me, Ms. Wells asked if she could talk to my parents in private. With an obvious angry and upset look in her eyes, my mother barked me back out into the yard.

Fucking aye!! What the hell is going on, I thought to myself as I got back to raking the yard. I was getting nothing but A’s in Ms. Wells class, what more did she want.

After maybe 45 minutes to an hour, Ms. Wells walked back to her car. Looking over at me, she paused and smiled.

“See you next Saturday Chris,” she yelled as she sat back in her car and drove off.

Next Saturday, I thought.

Christopher!!, my mom yelled.

My parents quickly explained to me, that my behavior was unacceptable. And that I was too not only receive extra homework during the week, but I was also to spend the next 4 Saturday afternoons at Ms. Wells house for extra tutoring.

There was no reasoning with my parents. It was a done deal. I was screwed for the next four Saturdays. This was going to absolutely suck… or so I thought.

Now, as I said before, Ms. Wells was no more than 27 or 28. She had attended and graduated from Charleston Southern University, and as I would find out later, was their homecoming queen her senior year. Even though she was a huge pain in the ass and rapidly becoming a bitch in my book, I had to admit that she was an incredibly attractive woman. She had shoulder length light brown hair, green eyes, stood maybe 5′ 7″ in height and probably weighed no more than 120 at best. But most of her beauty was concealed by her more than conservative dress.

School continued as usual the next week, with me meeting Ms Wells after class for additional homework assignments. And Jesus where they assignments! This was my senior year in High School. I had just turned 18! This was a time for fun and frolic, not college level work assignments! She explained to me that we would go over all of the additional homework, as well as anything new on Saturday.

Needless to say, my evenings were filled with me pouring over literature. The best way to get past this, I thought to myself, is just to bust my ass for a month. Get it over with.

Saturday morning, I woke up and did what little work I needed to get done around the house. My Mom reminded me that I was to be at Ms. Wells’ house by noon. Yeah yeah yeah, I thought to myself. So much for watching football with the guys today!!

Grabbing my books and notebook, I walked down to her house. Maybe she won’t keep me all afternoon, I thought as I rang her doorbell.

“Glad you could make it she said as she held the door open for me”.

I stood in complete silence unable to speak. Before me stood Ms. Wells wearing a pair of cut off jeans and a loose fitting white T shirt.

“Well?” she asked.

Snapping out of my trance, I quickly walked in. After closing the door, I followed her as she guided me to her desk. My eyes locked on her as I followed. I watched as her bare feet lightly slap against the floor. I watched as her slender shapely legs met perfectly at her denim-clad ass. And what an ass. Her cut offs were short … REAL SHORT!! And her ass fit them perfectly.

As she swayed gently to her desk, she explained how she had almost finished her housework. My young virgin cock, strained against my Levi’s as we reached the desk.

It was more of a large table than a desk. Grabbing a chair, she pulled it to the opposite side of the table. “You can sit here,” she said as she moved to the other side. Pulling out a week’s worth of work, I gently laid it on the table. I was really finding it harder and harder looking Ms Wells in the eyes. While her T-shirt was loose, it was more than filled. And I could have sworn she wasn’t wearing a bra.

Grabbing a book of Shakespeare from a shelf, she had me read it while she looked over my work. My eyes often wandered.

“Good work,” she said looking up at me after 20 minutes or so. Oh shit, I thought. I had been staring directly into her bosom… and I was busted.

“Uhhh … ummmm… yeah, thanks Ms. Wells, I stammered.

A slight grin slipped across her lips. She had me.

“See what happens when you apply yourself,” she said as she rose from the table. “This is college level material that you’re doing Chris. I want you to finish reading the play I gave you, while I finish my last bit of house work”.

While I don’t recall the play, I had read it before. It was almost unbelievable how I was able to concentrate on the Shakespeare, as well as Ms. Wells as she moved about her house.

I watched as she dusted… reaching up high to dust shelves… her T shirt rising above her shorts, exposing her lightly tanned lower back. I watched as she bent over .. her knees not bending … her ass beautifully encased in her cutoffs.

Finally around 3:30, I finished the play.

“Uhhh, Ms Wells,” I called to her. “I’m done”.

Rising from her squatting position, she brushed the sweat from her brow and walked over to me.

“Ok Chris, I guess that’s enough for today. I know you have practice Monday afternoon, but do you have a free period before school lets out?” she asked.

“Yes mam,” I’m free the period after second lunch,” I replied as I gathered up my things.

“Great, meet me in my class room then and we’ll go over what you’ve read”.

“Yes mam,” I replied.

“But, before you leave can you carry this box of garbage to the curb,” she asked gesturing to the den.

As an 18 year old, I had absolutely no control over the erection that was pounding against my Levi’s. This was exactly what I was most worried about. I’d been watching Ms. Wells dance and sway about her house, creating a nice adolescent bulge in my jeans.

Rising carefully, I picked up the box and carried it outside for her. Ms. Well met me at the door holding my books and notes, with what appeared to be a sly grin on her face.

“Here you go Chris, see you Monday.

Taking my books from her, I hurriedly walked home. My god, I thought to myself. I had no idea my English teacher was so hot, I thought to myself as I walked.

Throughout that night and the next day, all I could picture in my head was Ms. Wells. She was in my head… in my thoughts. Hell she kept me hard for hours … hell days!! Our meeting during 4th period was somewhat brief. Sitting in a student’s desk, she asked me to stand before her and give a brief synopsis of the play I’d read.

Being 18, I don’t know if it was my hormones or me … but she seemed different. She was dressed differently I mean. She wasn’t wearing the conservative pant suites, or ankle length dresses she normally wore. Instead she had on a short skirt (maybe 2 or 3 inches above the knee) and a white blouse with more than one button undone.

As I gave my report, I couldn’t help but watch her cross her lovely long legs. My groin stirred once more as my eyes ran from her legs to her chest. God I gotta get outta here, I thought to myself.

I was in hell … Pubescent hell!! Was she doing this on purpose?? Or was it my imagination. Whatever … it didn’t matter. It was one HELL of a motivator. I almost looked forward to our sessions.

Week after week, it was the same routine. The 2nd week she wore a pair of running shorts, and the 3rd Saturday a pair of spandex biker shorts. And after every session, she’d ask me to do some sort of task for her. Whether it was taking the trash out for her, or moving furniture. Whatever it was, I couldn’t wait to rush home… strip out of my cloths … and stroke my young hard cock until I was spouting cum across my bed. She had become my fantasy. Looking back at it now, I guess most kids that age fantasized about a teacher at one time or another. All I can say is that Ms. Wells was constantly in my thoughts.

On the Friday before our last session, Ms Wells pulled me aside after class. “Chris, I am very pleased at the way your attitude has improved over the last several weeks. Good luck in tonight’s game, and I’ll see you tomorrow at noon,” she said with a smile on her face.

Yes mam… and thanks, I said as I walked from the room.

We were playing our cross town rivals that night, and as the QB I took quite a beating. We not only lost the game, but I woke up the next morning feeling every hit I took the night before.

I was sore as hell, but thoughts of what Ms. Wells would be wearing for our last session, kept a smile on my face.

I rang her doorbell twice, before I heard her call for me to come on in.

“Go ahead and make yourself comfortable at the table,” she called out to me. “I’m upstairs and will be down in a minute.

Finding the table, I set my things down, made myself comfortable and waited.

“Sorry about that. Going to a Halloween party tonight and was trying to decide what to go as,” she said as she rounded the corner.

My breath stopped. I could not move. Standing before me was my 27ish English teacher wearing her college cheerleading uniform!! My cock immediately sprung to life, as I squeezed my legs together in an attempt to hide my arousal.

“So I guess you were a cheerleader at CSU,” I sheepishly asked. Her skirt was short, and the top was much tighter than I thought it should have been.

“I thought I might, but I seem to have grown a bit since I last had this on,” she said as she tugged at the top.

My eyes were transfixed. Glancing over at me, she saw me watching… she saw the expression on my face.

“Do you think this is alright,” she asked with a wide grin.

“Uhh … yes mam. You look great… errr… I mean fine,” I stammered out.

“Well thank you Chris. Are you ready for our last session?”

“Yes mam,” I replied.

For our last session, I thought you could watch a Shakespeare play I have taped. Sound good to you? By the way, how did the game go last night?”

“Yeah, that sounds fine Ms Wells,” my eyes still unable to slip from her tight body.

“We didn’t play to well last night,” I groaned as my muscles ached when I stood. “Goose Creek hammered us … Especially our QB.”

“Oh… I’m so sorry to hear that… wait a minute. Don’t you play quarterback?”

“Yes mam,” I said with a grin and a groan.

“Men and football,” Ms. Wells said as she pressed play on the VCR. “Sit in this chair,” she said gesturing to an oversized armchair. “Maybe I can work some of the soreness out.

As the play started, Ms. Wells moved behind me. Her small soft hands found my neck and shoulders and gently kneaded the muscles. “How’s that,” she asked as her hands worked through my T shirt. “Fine… feels great Ms. Wells,” I almost moaned.

“Just for today, you can call me Kathy … but just today,” she said with a chuckle. What is going on?, I thought to my self. The tent my cock was creating in my sweat pants was more than evident. Picked a fine time to wear sweatpants I thought to myself. Crossing my legs, I tried in vain to conceal my excitement.

“Chris… just relax,” Ms Wells said as her hands slid down my sides. “I used to be pretty good at massages,” she said with a chuckle. “Just watch the play, relax and enjoy. Do you mind if we get this out of the way?” she said as she grasped the bottom of my T shirt.

Before I could answer, she had it up and over my head. “Jesus chris,” she almost gasped as she saw a large bruise on my ribs. “I had no idea,” she said.

“I told you we got beat pretty good Ms… errr… I mean Kathy,” I stammered out.

“Sit right there, I’ll be right back,” she said as she dashed up the stairs.

She returned with a large pillow and a bottle of message oil, which she lay out on the floor. “Lay on your stomach, and I’ll see what I can do.”

“You really… I mean, Kathy… you don’t have…”

“Lay down and hush she interrupted.”

Ms. Wells quickly removed my shoes and socks, as I felt her squeeze the oil out onto my back. My cock seemed to grow harder and harder, and I was thankful that I was lying on my stomach. Closing my eyes, I quietly moaned as she spread her fingers across my back… gently messaging the oil in. Working her way up to my shoulders, I turned my head to the side as her hands slowly slid down my side. Opening my eyes to slits, I could see Ms. Wells kneeling to my left as her hands stroked my oil covered back.

Tightening my ass, I was unable to stop myself from grinding my hips into her carpet.

“Feel ok Chris,” Ms. Wells asked. There was a change in here voice. She no longer sounded like my teacher …it was different.

“Yes … feels great,” I almost gasped out.

“Lets get these off so I can finish,” she said as she hooked her thumbs into the waist band of my sweats.

Before I could answer, she had my pants down and off. I was stunned. Here I was in my English teachers home, lying on her den floor in only my cotton briefs!!

Gently her hands reached for my legs. Gently she messaged oil into my feet and calves. Slowly her hands kneaded upward. About mid thigh, I felt her staddle my legs. Gently she kneaded and massaged my thighs … higher … and higher. Her hands slid to the inside of my thighs and gently slid them apart.

I couldn’t move… couldn’t talk. My cock strained against my briefs… the head pocking above the waist band. Neither of us had said a word. I could hear Ms. Wells breathing heavier, as her hands slid over my brief covered ass. Leaning forward, she slid her hands farther up my back as her ass moved higher up my thighs.

As her hands reached my shoulders, she leaned down to my ear. “Does it feel good,” she whispered horsely. All I could do was moan.

“Roll over Chris,” she whispered as she lightly kissed my cheek.

As she rose to her knees, I rolled onto my back under her. Her ass rested on my upper thighs, as her short skirt spread out over her soft thighs. I watched as she smiled, her chest heaving. Slowly, she pulled her top up and over her head. Her nipples were hard, her breasts without sag.

I didn’t know what to do… I was lost. Hell I’d only seen my girl friends breasts a couple of times, but these… oh god!!

Slowly, Ms. Wells bent down and lightly kissed my lips. “Just relax Chris,” she moaned against me. Lightly she licked my lips, as her hands stroked my hair.

Reaching up, I reached for her. Finding her waist, I slowly slid my hands upward, as her tongue slowly parted my lips. With my hands trembling, I found Ms. Wells breasts, as she hungrily sucked my tongue into her mouth. As I squeezed and messaged, her nipples pressed against my palm.

“Mmmmm…,” she moaned as she pulled back from my mouth.

Grinning, she knelt over me, and slowly ran her fingers down my belly. Reaching my briefs, she stared for a moment at my hard cock peeking through the waist band.

“Is this for the teacher,” Ms. Wells asked with an evil gin on her face.

Lightly she ran a finger nail over my exposed head. Gasping, I arched my hips up into her. Grasping the waistband, she pulled my briefs down and off… allowing my cock to bounce free.

Moving from my side, I gasped as her fingers found my hardness and her lips found my belly. Slowly she traced a line to my shaft… lightly tracing upward.

“Oh yes,” I moaned as Ms. wells lips reached my head.

Glancing down, I watched as her lips slide over my swollen member. Slowly my cock slid deeper down her throat, as she sucked my virginity from me.

“God yes… I’m gonna cum,” I moaned. “Oh god I’m sorry,” I moaned to Ms. Wells.

Pulling my cock from her mouth, Ms. Wells looked me straight in the eye. “Cum for me Chris,” she said as her hand stroked my cock. “Cum for me,” she moaned as she once again swallowed my cock.

“Oh god… OH GOD YES!!” I almost screamed, as cum rushed from my throbbing cock.

As my orgasm subsided, Ms. Wells stood and slid her skirt and panties to the floor. “Did you like that,” she cooed as she sat down in the arm chair in front of me. Pushing myself up on my elbows, I watched as her hands slid from her breasts… where she pinched and twisted her hard nipples…down her soft belly …finally reaching her nicely trimmed pussy.

Slowly she slid one, then two fingers in her wetness. I was transfixed. I couldn’t move as she watched me … watch her.

“You want to help me Chris,” Ms. Wells cooed. Unable to speak, I nodded yes. Grinning she beckoned me with her free hand.

“uhhh… I’ve never … ummm …,” I stammered as I crawled over to her.

“I’m the teacher remember,” she said as she guided my head between her soft thighs. “let me teach you”.

“Lightly lick the lips Chris…yes… yes, thats it baby. Now slowly slide your fingers upward… OHH!! yeah… find it?? Thats my clit Chris. Thats my key to heaven,” she gasped.

Looking up from her thighs, I watched as she closed hers while squeezing her breasts. Looking back down, I gently sucked her clit into my mouth.

“Oh God yes Chris,” Ms. Wells moaned.

Reaching up with my hand, I slid 1, then 2 fingers deep into her pussy as I sucked her clit harder into my mouth. Her ass slide further down the chair, as she arched her hips to my mouth.

As I slid the 3rd finger in, she cied out in bliss. “God yes… don’t stop Chris … Please don’t stop!!”

I could feel her muscles tighten around my fingers as I thrust in a final time. Grasping my hair tightly, she pull my face hard against her pussy as she exploded in sexual bliss. I never stopped licking… I didn’t know to. Sliding to the edge of the chair, she brought her lips to mine… gently she sucked her juice from my tongue, as she kissed me hard.

Pulling back, she rose to her feet… smiled and took my hand.

Reaching the table that we had used for a desk for the past 4 weeks, she swept it clean with her right arm. Sitting on the edge, she reached for my waist and pulled me to her.

Lightly she stroked my cheek as she looked deeply into my eyes. “Did you know, I knew you were watching me Chris, she cooed at me. Did you know I wore those cloths for you?” Did it make you hot? Hard? It did me, Chris,” she almost moaned as her hand slid down to my cock.

“I know we shouldn’t being doing this, she quietly whispered. But just the way you watched me … looked at me,” she quietly said as her hand stroked my cock.

“I need you Chris. I need to teach you,” she said as she slowly guided my hardness to her swollen lips.

Gently I pressed inward as she grasped my waist. I looked down and watched as my swollen cock slowly slide between her wet lips. Grasping Ms. Wells waist, I thrust my cock deep into her pussy … unable to wait… not wanting to wait.

With a gasp, she wraps her legs around my waist and moans as I thrust my cock faster and deeper into her.

“Oh God yes… Slower… don’t cum yet,” baby.

I try to slow, but Ms. Well has to pull me up on the table. Gently she rolls me to my back and straddles my cock.

Smiling she slowly slides her pussy down my hard cock.

“God yes…,” I moan out as she slowly rocks back and forth. Reaching for my hands, she places them on her breasts, as I thrust my hips to hers.

I can feel her pussy tightening… gripping my cock, as the cum wells up in my balls. As she arches her back, I explode hard up into her as she reaches orgasm as well.

As I regain my breath, she slowly slides from the table, and reaches for a robe draped against a chair in the corner.

As she ties the sash, she walks back toward me as I sit up.

“So, Chris… ”

“What time is our next study session?”

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