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.
