The Principal and The Star Student

Author's Disclaimers: First, another different sort of story for me. Second, all sexually active people are over 18 years of age. Third, every character in my little tale is fictional, and reside in the recesses of my mind. Lastly, this story is not wall to wall sex.

I am Sandra Rosen, a 51 year old principal of a prestigious private school, located outside the city of Seattle. I spent the first 21 years as an English teacher and was hired as principal just over 7 years ago. For the first 10 plus years of my teaching career I was married to my first love, Brian O'Conner. We met in college, with him 2 years ahead of me. While not exactly love at first sight, we dated exclusively my last year and a half, and got married, while I was completing my 5th year, for my teaching credentials.

Let me try to describe myself. In flat heels, I barely reach 5 feet tall. With constant exercise and trying to eat properly, I try to keep my weight under 135 or so. With twin daughters, Carol and Cheryl, now 26 years old, I won't try to fool any of you about what age, child birth and gravity have done to my tits. When Brian and I got married, I was a 36 C. Now, I'm lucky to fit into a 38 DD. At least my exercising keeps the rest of my body parts in decent shape.

While I was busy trying to mold the minds of the next generation, I soon realized Brian was trying to mold other women into their mattresses. It must have been during our 8th or 9th year of marriage, when this lady of very average features knocks on my office door, and when I showed her inside and asked how I could help her, she stated she was busy fucking my husband.

"And that's my problem, how?" I responded, knowing Brian was dipping his wick places other than at home. I continued, "I'm just waiting for the right time to kick his sorry ass to the curb, then you can have him!"

With that, she stomped out of my office. I really didn't know what she expected me to do.

Let me interject, here, that while having the morals of an alley cat, Brian was a first rate financial analyst, with the largest local bank in our area. A top notch provider, and a good father to our girls. It was just too bad I wasn't aware of his wandering eye before we got married. I was plotting my freedom from him for several years, and when we parted, I was left with my daughters, my job, and my financial freedom, thanks to a top tier divorce lawyer.

It was during our final year of marriage, I had heard whispers of yet another fling he was having. This, I later found out, left him with a pregnant girl friend. This only added to my case in divorce court.

My girls and I flourished on our own. I finished my PhD work, my girls excelled in all subjects in school, and they tolerated their 2 or 3 weeks each summer with their father. He really tried his best to dote on them, but he now had a son with his new, younger wife.

During the first few years as a newly single, still young woman, any sexual happenings weren't even in my thoughts, let alone actions. I guess you could say I fell into a celibate lifestyle. As my girls grew and entered middle school, I started getting dating offers, which at first I ignored. My girls were my top priority, and with them entering puberty, I convinced myself I had to set a great example in the morality game.

Along with me staying on the moral high road, some of the offers I was receiving bordered on the ridiculous. One gentleman, who had to be 25 years older than me, asked me to come on a cruise with him! This was going to be a first date? I don't think so. He was actually hurt when I declined.

With others asking for just a dinner date. I decided to try, just to break my boredom.

First date number one. Gene, or I think that was his name, took me to a family pancake house. Wow, what a guy! When we finished, he actually had the balls to ask, "your place, or mine?" My reply was right to the point, "I'm going to my place, by myself, you can go wherever you want."

First date number two. The father of one of my students asked me to dinner, so I checked the school files, and sure enough, he was listed as having a wife! Oh, just for the record, his name was Brian, too. When I asked if his wife was joining us, he actually said, "If you want her to, that's O K with me."

After these two, I stopped even considering any number three. It was around this time I discovered the joys of self pleasuring. I built up the nerve looking online and found what looked like an average sized vibrator. Batteries not included.

With the twins going to sleepovers some weekends, I discovered how much I truly missed a cock that didn't cheat on me. I just had to make sure the linens were washed before the Snoop Sisters returned on Sunday afternoon.

The years were flying by, with both girls off to college, any my love life stuck in a horrible rut.

I actually accepted a first date number three. This was way out of my comfort zone. This date was with Alice, one of my student's mother. We had known each other for just a little while, and when she picked me up, I let her know that I had never dated a woman, and truthfully didn't know why I was doing so, at this time. She quietly informed me that dinner would be the only thing, if that was to my liking. It proved to be a very enjoyable dinner and we talked for nearly two hours, afterword. As she got up to leave, she took my face in both her hands and gave me the softest, most sensuous kiss I had received in years. My vibrator gave me multiple orgasms that night, but we never dated, again. We remained friends, but nothing more.

One afternoon, with my girls both graduated, and working in the world of finance, and each living with a girlfriend, I was looking at mid year applications to my school. Yes, both of my daughters came out in college. and I wasn't bothered in the least.

One application caught my eye. A young man entering the final semester of high school. Nearly 18, perfect 4.0 grades, with many advanced placement classes, and a very familiar name. Byron O'Conner. Yes, the son of my ex husband. As I am looking at his paperwork, I noticed a glaring omission. On the line asking for siblings, he wrote, none.

I made an appointment for his interview for the next day. He told me he would be there, by himself.

Right on time, this Byron O'Conner walks into my office, skin the color of light milk chocolate, standing around 6'2" or so, on the slender side, and very soft spoken.

"Good morning, Mr. O'Conner,"

"Good morning, Dr. Rosen,"

"Let me say, first off, we pride ourselves at this school on honesty, as well as academics," I told him. Before he could answer, I took a picture of my daughters from my desk drawer, put it on top of my desk, and watched as his face blanched.

"Byron, I want you to meet Carol and Cheryl O'Conner, my daughters, and I believe your sisters!"

"Half sisters, to be accurate, Dr. Rosen," with his head down. "Do you want me to leave?"

"No, young man, but I would like an explanation,"

"They never got along with my mother, if you want the truth. I think mom thought they were stuck up."

The more we talked, the more relaxed he became. In truth, my girls made me well aware of the constant tension between them and "step mommy" It didn't help matters that their father allowed this to fester.

"Are you aware they are moving to The Bahamas, next month?" And I will be living with friends of my mothers.

I told him I had heard that it was a possibility.

I quickly approved his admittance, and since he was 18, he could live with any adult.

As the semester got into full swing, we actually had several family dinners, showing Byron his sisters were pretty cool kids, as were their girl friends.

As graduation neared, I asked him if his parents would be there, and he very quietly answered in the negative.

"Do you want me to contact them?"

"Absolutely not!" he said. "Its their loss."

I could see a tear starting to roll down one cheek. It broke my heart that my thoughtless Asshole of an ex wouldn't make time for his only son's graduation. I moved next to him, giving him a little hug.

Not only did he hug me back, he started crying and hugging me a bit closer. Oh, fuck, I am getting wet panties! Holy shit, he seems to be getting hard!

I quickly broke off the hug, and he couldn't apologize quickly enough. I was hoping he couldn't see how red my face was. I already knew it would be a long, happy night with Mr. Dildo.

A few days after graduation, and getting accepted into my alma mater, the University of Washington, he came over to my house, and started to apologize all over, again.

Very quietly, he says he has something extremely personal to ask me.

"First, let me tell you, if this makes you uncomfortable, tell me right away. I have been seeing this girl in one of my classes, and she has hinted at moving our relationship to another level."

"Go on, Byron, I have an idea the nature of your question, but I want to be positive."

Sighing, deeply, he tells me he has never done anything more than kissing her, while being fully clothed.

I was almost going to remind him of the 1946 Broadway play, Annie Get Your Gun, with the song "Doin' What Comes Naturally", but kept my mouth shut.

We were sitting outside, enjoying the late afternoon sunshine, with me wearing a light cotton blouse and shorts, and Byron in board shorts and a tank top. While we were talking, I asked him if the girl he was seeing was one of the girls I had met. He told me they had classes all semester and had studied together several times and enjoyed each others company, and yes, I had met her.

I happened to glance down and noticed a bulge growing in his shorts. The thoughts running through my head had me headed straight to Hell.

"Byron, are you still a virgin?"

An affirmative nod.

"How about I show you instead of telling you?"

I moved closer, and let one hand lightly grip his growing cock.

"Oh, shit, Dr. Rosen"

"Byron, I have my hand on your schvantz, call me Sandra!"

My hand slid up inside the leg of his shorts, and briefs, touching his now throbbing cock (schvantz). I moved my other hand behind his head, and gently kissed his lips. I was very aware by his movements, and quickened breathing, he was already very close to exploding. Quickly, I undid his shorts and pushed them and his undies down around his knees. Just in time, as he literally exploded with stream after hot stream of cum, filling the napkin in one of my hands.

I couldn't believe how much he came. Topping that, he remained rock hard! Maybe, it had something to do with my hand still stroking him, very softly. The look in his eyes was pure bliss, so I leaned over, taking the head of his cock in my mouth, and running my tongue all around the uncut tip. Pushing the foreskin the rest of the way down, and taking about half his 8 inches into my mouth. My other hand gently caressed his balls, as he unbuttoned my blouse, letting it fall off my shoulders.

I sat up, still holding onto his package as he unhooked my bra. Before I could say a word, we laid down on the chaise lounge kissing and fondling each other. He managed to get my shorts and panties off, allowing him his first view, touch and hopefully taste of a vagina.

"Lets take this inside," getting up and guiding him to my bedroom, both of us naked as jaybirds.

"Are you sure about this, Dr, oops Sandra?"

"I'm not really sure, but I think actual demonstration is the best learning tool."

With that, he leaned over and gave me one soft kiss after another, with his hands gently massaging my aching boobs. Falling onto my bed, locked in our embrace, my hand kept rubbing his cock, making it grow even harder, if that was possible. I rolled onto my back, gently nudging him between my opened legs.

"Be careful, I am a little out of practice, and you are very large!"

Very slowly, the tip of his shaft entered my sopping wet sex. It didn't take him too much more encouragement to get the drift of what was expected of him. While I grabbed hold of his shoulders, he started pumping a bit faster. Leaning over, licking my very engorged nipples, one at a time. My head was spinning, and thoughts of me heading straight to Hell left my mind, as he continued his piston like fucking.

I think when I let out two or three "Oh, Fucks!" his eyes shot open and he whispered if I was O K? God, yes, I cried, as I felt yet another orgasm building starting at my toes and rocketing throughout my entire body. Just as I was cumming, I felt like a fire hose went off in my pussy! Jesus, this kid came just a few minutes ago, and let loose another torrent of white hot cum into my very essence.

Panting, he leaned over and whispered in my ear, "that was the most intense feeling I have ever experienced!"

"Just wait, Byron, we have just started your lessons," I said, with a mile wide grin.

"There's more?"

"Oh, yes, much much more, if you are willing to learn."

After cleaning up the huge mess he made, and giving my stretched pussy time to recover, I went back into my bedroom, just as he finished cleaning himself.

"Do you have any questions?" I asked rejoining him on my bed, still naked. "Don't be shy about anything," I told him, noting his reluctance to speak.

"Please, don't take this the wrong way, but I am guessing younger girls have breasts that are a bit firmer."

"My God, Byron, age, child birth as well as size determines what a woman's boobs look like."

Smiling, he gently took one nipple between his thumb and forefinger and very slowly started rubbing. Leaning down, he took my other nipple in his mouth and started sucking, softly. My breathing quickened, and I placed my hand on his semi hard cock. My fucking goodness, doesn't this kid ever go soft, I thought?

Rolling him onto his back, I gave his manhood a very sensual kiss, and moved on top of him, taking his sex into my still excited pussy, and slowly moving up and down. With my boobs hanging right at his shoulder level, he took each one in his hands, giving them an equal amount of attention. The one thing he didn't need any teaching was his fantastic kissing. At first, he was a bit reluctant to use his tongue, but quickly learned of that pleasure.

After a few more minutes, I whispered, "new lesson," and moved off his rock hard member, and eased upward until my pussy was right over his mouth.

"Take your tongue and move it up and down my pussy lips," I instructed. Without any further instruction, he started licking me up and down, and soon had both hands gripping my ass cheecks and findind my clit without having to be told where to find it.

Fuck me, but this kid is a natural, I thought, as my body started shaking. It took just a few more serious licks and I came about as hard as I could remember. Rolling off to one side, trying to catch my breath, I glanced back, seeing him still rock hard. I kept one hand on his tender face, looking into his eyes. "More?"

"Oh, yes, Sandra, anything you want to teach me will be great,"

I moved slowly onto all fours, giving my ass a little shake, telling Byron to get on his knees. Giving me a really strange look, I realized he was looking right at my back door entrance.

"Not the butt, kiddo, you are way too big, for this old broad, stick to my pussy!"

It took him about 5 seconds to enter my sex, slowly pumping in and out. Reaching under me, touching my nipples, then taking each mound in his hands, massaging each one, while building his pace, in and out. I must have been moaning a bit too loud as he asked, again if I was O K. All I could do was nod in the affermative.

Just about the time of my 10th or 11th orgasm, he let loose yet another wave of his youthful offering, overflowing my pussy. As he rolled off, I basically collapsed on my bed. I couldn't believe how exhausted I was. To show what a thoughtful young man he was, he took a few tissues and started cleaning up my mess, before I leaked all over my bed.

After cleaning myself up, I went back and get on my bed, laying right next to Byron, looking at his smiling face, staring back at me.

"I guess I found the best teacher in the world, Sandra," he quietly said.

"Any questions, and nothing is off limits," I added.

Thinking for a few minutes, he started by thanking me, many times, telling me neither of his parents ever talked about sex with him. I couldn't believe in this day and age, that two responsible parents wouldn't talk about sex with their son. I guess my ex didn't qualify for being thought of as responsible.

"Is anal just something you don't like, or is it my size," he asked.

"Your size is one thing, but with a very good lube and a willing partner it is something to be considered, I am not a big fan of having a cock, especially one as large as yours up my ass." Pardon me for being a bit crude, I added. He just smiled, and gave me yet another soft kiss.

"Anything that you and your partner agree on is fair game, agree on being the operative words."

And always remember safe sex practices. Even if your partner is on the pill, until you are sure you are her only, use a condom. That goes for anal, no matter what.

"I guess you are not worried about becoming pregnant?"

"No, Byron, I am way past that concern, but thanks for asking."

Glancing down, I noticed his cock growing again. "Oh, no, Byron, I am far too sore for anything more, right now,"

Without thinking, I whispered, "I love you. Byron!"

"I love you, too, Dr. Sandra, you will always be my first."

I must have fallen asleep, because I found myself in bed, by myself and noticed it was getting dark outside. Throwing on a robe, I went to my living room, finding Byron sitting on my couch with just his shorts on and one huge grin.

Sitting next to him, after several scorching kisses, I looked him in his eyes and said, "you know this can't continue, don't you?"

Nodding his ascent, he quietly told me no matter what he ever did in life, he would always remember me as his educator, in each and every phase of life.

We spent that night in bed, cuddled next to each other. Sometime during the night, I felt something pressing between my butt cheeks, and it truthfully was turning me on. Should I try? Am I brave enough? Did I have a condom?

Rolling over, and opening my night stand, I found a condom, put my finger to his lips, silencing him, I handed the condom to him, heard the wrapper opening, and took my well lubed fingers rubbing my ass entrance. Moving so my backside was right up against his constantly hard cock, he knew what to do. Very slowly, the head of his cock found my little brown pucker.

"Slowly, Byron, very slow!"

"Oh, my, this is so tight,"

"A little more"

He pushed another inch popping inside my sphincter.

"Fuck, fuck, a little more, more!"

Finally, with all 8 inches up my ass, I was on fire. I had never felt like this. Ever! We changed positions, with me on my back, with my legs resting on his shoulders, and his cock back inside my behind.

Picking up steam, he just was the kindest, most gentle soul I would ever have fucking my near virgin ass. I actually squirted, a little, that sort of scared both of us, but didn't cause us to stop.

When he finally exploded, I was near exhaustion, so when he rolled off me, I just laid on my back, panting, like a dog in heat.

"Are you O K, Sandra?" my beau asked, quietly.

"Better than you could ever imagine!" I answered after catching my breath.

Glancing down, I finally noticed he was no longer hard! We both showered, with him having to hold me upright. Even though we slept together, I had to warn him there would be no funny stuff.

While eating a casual breakfast, we talked about most everything, except our day long fuck fest. He did, though, have a constant grin, all morning.

As I was putting our dishes in the dish washer, he came up behind me, wrapped his arms around me, lightly touching my breasts, and kissing each ear lobe. Just as I was ready to tell him to stop, my body betrayed that thought, as my panties became wet, all over, again.