My brothers were excellent athletes and although my teachers always compared me to them, I had no athletic ability at all. I'd rather play the piano or read a book.
Not only that, compared to them I was small. They made sure that I wasn't harassed too badly at school, but at home they called me ‘runt,' and mercilessly picked on me.
When we became adults, I got even with my brothers for all their bullying. Dwight worked for the town; he was called a garbage man back then. George worked the midnight shift in a factory. Me? I went to law school. I joined a law firm in town, mostly handling residential and commercial real estate transactions.
In school my favorite teacher was my sixth-grade teacher, Mrs. Donaldson. I had a crush on her. I thought she was beautiful. Of course, I was twelve, just starting puberty and Mrs. Donaldson was married and I guess she was about thirty, which I thought was very old.
Whatever Mrs. Donaldson asked me to do, I did it 100%. My homework was always perfect. I'd do anything to please her.
Not just a sixth-grade crush; all through high school when I jerked off, I always thought of Mrs. Donaldson.
One summer, my dad and mom took us to a lake about an hour from home. It had a great beach. I saw her there. She was with some guy probably her husband; he was a dork. Of course, he was. He was with her and I wasn't. Ah, the fantasies of a teenage boy.
Anyhow, they were in the water just about to their knees; just talking. At school, she usually wore her hair up, in what used to be called a bun. Now, that blonde hair hung to the middle of her back. However, it wasn't her hair I was looking at. At the time, I thought she had the greatest ass; perfectly sculpted. And her tits: my God, they were huge.
She may have been able to hide them at school; her tits and her ass, I mean, but not in a bathing suit.
I couldn't wait to get home to jerk off. I didn't. I went into one of the bathroom stalls and jerked off right there. I didn't even care if I got caught. I never shot so much in my life.
This story really starts when I received an invitation to my tenth high school reunion. I didn't even think about going. I wasn't part of the "in crowd;" I was kind of a loner. On the other hand, I could throw it in those assholes' faces that I was a lawyer and many of them, like my brother, George, worked in one of the local factories.
At the last minute I sent back my RSVP.
With the massive influx of baby boomers, the town, Franklin, built a huge school campus. One wing was K-6; another was junior high (7-9) and the third wing was the high school (10-12). The fourth wing was the gym, cafeteria and administrative offices.
The reunion activities included a tour of the new school on Friday afternoon of reunion weekend. I'd gone to the "old schools," built after World War I. I'd never been in the new school. I thought I'd join the tour. School was out for the summer. The campus was empty except for us alums.
The tour was of the high school wing, but we were invited to wander about but to meet at the cafeteria in an hour for lunch.
There was no one in the tour group of alums that I cared to hang out with. I went off by myself and got lost in the maze that was the new school. I heard some noise in one of the classrooms. I walked in, "excuse me, can you direct me to the cafeteria? I'm lost."
It wasn't until she looked up that I recognized her: it was Mrs. Donaldson. She started to say, "Gladly, it can be a little confusing. . ."
"Mrs. Donaldson?"
"I used to be Mrs. Donaldson. I'm divorced. It's Miss Richman."
"I'm sure you don't remember me. I'm Doug Fineman."
"Ummm, this happens to me all the time. I'm sorry but after teaching for almost twenty years, I've had so many students that I can't possibly remember them all. I'm sorry."
For a woman now over forty, I thought she looked beautiful. For a moment, my mind flashed back to those nights in bed when I was in sixth grade, thought of her and my hand slipped inside my pajama bottoms.
"I understand. You must have had hundreds of students."
"That's true. Let me walk you to the cafeteria and you can tell me what you've been doing since sixth grade."
"I didn't mean to interrupt you. If you'll just point . . ."
"I was just cleaning up my classroom at the end of the year. It's not a bother. Tell me about yourself, it's Doug, right?"
"Doug Fineman." I told her about going to a state university for my undergraduate work and then to law school in New York."
"After seeing New York City, you still came back here?"
"New York was much too rushed for me. I needed something a little quieter; what better place than Franklin?"
"Me, too. I'm from Los Angeles. My husband was from here. Even after we were divorced, I didn't want to leave. It's a lovely town."
By this time, we'd arrived at the cafeteria. I looked around, there was no one I wanted to sit with. "Mrs. Donaldson . . ."
"Miss Richman."
"Yes, Miss Richman, I'm enjoying this conversation. Why don't you join me for lunch? I don't think anyone will mind, and if they do, I'll gladly pay for your lunch."
"I was going to finish up and go home to a tuna sandwich. This has to be better," she laughed. "Thank you."
We continued to talk. She asked more questions about law school and I asked about her undergraduate days. "Doug, those were so long ago. I look back and think how could I have gone to an all-girls school? I'd never wish that on anyone."
All too soon our tour guide announced that we had a question-and-answer session with some current students. "Miss Richman, you may thing I'm bold or crazy, but I've enjoyed talking to you very much. The reunion committee has activities planned for tonight and Saturday night, but what would you say about dinner next Friday night?"
She looked at me as if I was crazy. After all, I was twenty-eight and she was somewhere over forty. "Mr. Fineman, Doug. I got married at twenty-two, divorced at thirty. I haven't been on a date since I went out with my ex-husband in college. What do people do on dates?"
"I'll be honest with you, I don't date very often myself, but I'm thinking dinner or dinner and a movie."
It was true. I'd finished law school and moved back here three years ago. I could count on one hand my dates. It's not that I didn't want to, but I rarely found a girl interesting enough to spend an evening with. Mrs. Donaldson, er, Miss Richman was interesting.
"A movie sounds good. Have you seen the latest James Bond movie?"
"I'd love to. I can't imagine anyone but Sean Connery playing James Bond. We'll see. And Doug, maybe after the movie, we could share a pizza. Nothing fancy."
Miss Richman, Diane, and I started seeing each other on weekends.
It started with a kiss goodnight. By mid-summer, "Doug, I'd like you to spend the night, but as a divorced woman, I have to be careful about my reputation. There are members of the school board who are a bunch of busy bodies. I drive over to Marklinburg just to buy a bottle of wine. They're so nosy."
"I understand." For a few weeks we tried to be as circumspect as possible. I wasn't a virgin, but I also wasn't all that experienced. Not like Diane must have been; after all she was once married.
Just two weeks before school started, Diane hit me with what I thought was a bombshell. "Doug, I'm moving."
"Where? Why? What about school? What about us?"
She put her arms around my neck. "Don't worry about us, and don't worry about school. I'm moving Marklinburg. It's just ten miles from here. They're called condominiums. It's like an apartment, but I own it."
I'd recently done a real estate transaction for one. It was a new concept in housing. "Why?"
"I'm out of the school district. They're unlikely to see what I'm up to in Marklinburg. Besides, my new community has over a hundred units, even if they find me, they're unlikely to find out who's coming and going."
We'd been sneaking around. I'd arrive and leave after dark. Diane was a willing lover but she seemed nervous. She put a robe on in her bathroom and wouldn't take it off until she joined me under the blankets; as if there was a Peeping Tom checking on her. She was concerned with every car that drove through her parking lot. Was the car driven by a member of the school board scrutinizing who she might be entertaining? And what kind of entertaining was she doing?
Now, that she moved, it was like there was a different woman in bed with me. "Doug, I've been so unfair to you since we started seeing each other. It's just that. . ."
"I'm sorry, my mind was somewhere else. I'm so enamored with your beautiful breasts, I wasn't listening," I smiled.
"You're so understanding. What you don't know about me is that I'm not the goody-two shoes school teacher that my students know. Doug, in bed, I don't have breasts; I have tits, which you seem to be enjoying."
"They're lovely."
"And Doug, I have a pussy and this big hard thing," she reached between my legs, "is a cock, which I haven't had the pleasure of sucking yet." Then Mrs. Donaldson, I mean Miss Richman, Diane went down on me.
We'd had sex before, but it was in the missionary position; there was no oral sex. It wasn't me. Diane wasn't willing to go there. It was her fear of the school board. I assume because she'd been married, she'd done it all.
As for me. I had a couple of girlfriends through college. We tried of variety of positions; one girl's favorite was 69ing; another liked the doggie position. My one girlfriend in law school insisted on blowjobs only. "Doug, I can't take a chance on getting pregnant." Of course, I didn't mind.
As I said, she was a different woman now that she'd moved out of the school district. The blowjob was incredible; far better than that law school girl who only did blowjobs.
Not that I have a big cock, but Diane took it all and then bobbed up and down on it from my cockhead to my pubic hair enthusiastically. "Wow, Doug, your cock is so good to suck; I'm counting on you to remind me to suck it more often."
She didn't make me cum, but that's only because I insisted that I desperately needed to reciprocate. "Oh, you do, do you?"
"Ummm, Diane, I have to admit that it's not something I've done too often and I'm not sure even then I did it right."
"Well, Doug, there's only one way to learn how to swim." She spread her legs. "Jump in."
I didn't literal jump in, but you get the picture. Fifteen minutes later, "Doug, you have my pussy so ready for your cock. Come up here and fuck me."
We fucked in the missionary position as always. Later, when we were snuggling, "Doug, I had a grand time sucking your cock. However, would you mind if I helped you improve your pussy eating? Your tongue is certainly enthusiastic, but there are some things I like."
"Not at all. I'm all about making sure I'm pleasing you." Just like I'd done in sixth grade.
That started a wonderful adventure that I'm not sure Diane planned on. I certainly didn't.
As a reminder, I was a twenty-eight-year-old successful lawyer and she was a well-respected school teacher: at one time my sixth-grade teacher; now in her forties. She was a divorcee and my sexual experiences were somewhat limited.
It started innocently enough. The next time we were in bed, I went down on her. She stopped me. "Doug, here's what I like. Spend a lot of time on my titties; that gets my pussy wet."
For me that wasn't a problem. At school, Miss Richman wore over-sized blouses and blazers. She knew what tight blouses did to boys going through puberty and she knew what they were going to do when they got home: in their beds or in the shower. I certainly had.
What I'm trying to say is that Diane had big ones; or as she liked to ask me: "Doug, do you enjoy playing with my big titties?"
Big and beautiful. I could suck them all night, but that was only the beginning. Once her pussy was wet:
"Tell me all you've thought of for days or since the last time we were together, you've been looking forward to eating me; my pussy has been on your mind."
I didn't have to make it up. I'd been looking forward to fucking and eating Diane's pussy since the last time I ate and fucked it.
Diane Richman was a blonde and when kneeling between her legs, I was faced with the most beautiful pussy. She shaved all the hair from her fat labia majora. There remained just long wisps of golden-brown hair above her pussy on her pubic bone. Unlike most women I'd known, and there weren't that many, her pubic hair was not small tight curls. Instead, there were long curly strands.
Being blonde, her open pussy was a delicious pink. Once I was comfortable with her, that's what I called it. "Diane, you have the most delicious pink pussy."
There was one more part: her clitoris. It stood out: a fat purple button about the size of the tip of my thumb. It was prominent, the purple stood out against the pink; the delicious pink of her pussy. Better yet, it was very, very sensitive.
"Doug, as you leave my titties, tell me how beautiful my pussy is and how just thinking about it has your cock hard."
Diane didn't know I'd been thinking about her tits and pussy since sixth grade.
"Once you're there, I'll open my pussy for you, and I need you to be just as enthusiastic as you were before when you ate me. Don't spend too much time there because my clitoris will be begging your tongue to play with it.
"Once you start, whatever you do, don't stop even if I scream at you to stop. Doug, I love to cum and cum. It turns me on to be multi-orgasmic. If you do all that, I'll be yours. You can have anything you want: fuck, blowjob. You can even fuck my ass."
I had no interest in fucking Miss Richman's ass. Once in college, after a night of drinking, my girlfriend suggested it. I didn't like it all that much. Neither did she.
"Doug, I hope you remember all this, but right now, I'm in the mood for a blowjob. What about you?"
Who turns that down?
A month later, we were in bed when I went down on her. My hands and mouth were all over those incredible tits. I was working my way from those fabulous tits. "Diane, I didn't sleep much last night thinking of your sweet pussy. I'm so looking forward to eating it."
"You're a quick learner." She pushed my head down.
The truth was that I hadn't slept much. I was thinking of eating Diane's pussy. Eating it the way she wanted to be eaten. Pleasing her the way little sixth grader Dougie Fineman followed her directions.
"Oh yeah, oh yeah just like that. Hmmmmm, hmmmmm, you have my clitoris on fire. Keep eating me, Doug."
I continued even after she begged me to fuck her. Finally, she pushed me off her. The multi-orgasmic Diane Richman was a wild woman. We may have started out in the missionary position, but soon we were rolling around on the bed. She ended up on top. "Suck my titties; suck my nipples hard. I like it when you use your teeth just a little."
Actually, I didn't. Not that sucking her tits wasn't enjoyable; it was just that Diane was bouncing up and down on my cock, and those tits were bouncing too. I never had a chance.
As I said, as a once married woman, Diane had much more experience than me. As she bounced, she was making herself cum. The orgasms my tongue generated, continued as she rode my cock. "Ooooooooooooh, ooooooooooooh, ooooooooh," she moaned as she bounced. "Ooooooooooooh, oooooooooooh, ooooooooooh."
Although, I couldn't get her tit in my mouth, I could enjoy the spectacular view of those magnificent tits bouncing. Magnificent is an understatement.
"Cum, baby, let me feel you cum." She bounced faster; those tits continued to bounce. "Oooooooooh, oooooooh, ooooooooh." This time we came at just about the same time. Diane collapsed on my chest.
Twenty minutes later, still in each other's arms. "Doug that was the best fuck ever, and it was all because of the way your tongue did my pussy."
I was still trying to catch my breath. It was the best fuck for me, too. "If that's what it takes, I'll gladly eat your delicious pink pussy every time we make love." That wasn't the first time, I called it her ‘delicious pink pussy.'
"Oh Doug, I'm so happy to hear that." Her hand went to my cock; my very dead cock. "When you're ready, my mouth will be too."
Of course, it took a while; a long while, but once she started, Diane proved to be a vociferous cock sucker; much more so than when she'd given me blowjobs before. When she came up for air, which she did infrequently, "Doug, this is what you get when your tongue does my pussy."
From then on, with Diane's direction, I became an avid pussy eater. "That's it, Doug, do my clitoris again. Eat it, eat it good."
Without thinking, sometimes, I'd mumble, "Mrs. Donaldson has the sweetest pussy. Mrs. Donaldson's delicious pink pussy makes Dougie's cock so hard."
She didn't correct me. After all, she was on the verge of cumming again.
After numerous orgasms, and more rolling around on the bed fucking, followed by a period of recuperation, "Doug, when you were eating me, did you call me Mrs. Donaldson?"
"I guess I did. I wasn't thinking with my brain. I was thinking with my cock."
"And your tongue. Oh yeah, your tongue. Doug, when we're making love, are you Doug Fineman, twenty-eight-year-old attorney pleasing forty-three-year-old Diane Richman or are you sixth-grader, Dougie Fineman, trying to please thirty-three-year-old, Mrs. Donaldson?"
"I didn't even realize it. Did I really say that?"
"You did and when you did, your pussy eating got even better and my orgasms were beyond words. Fireworks were going off in my brain."
The blowjob the next morning was beyond description. Diane didn't stop even after I came; even after my cock shrunk, she kept licking, kissing, sucking until I was hard again. Then Miss Richman started all over again. It was a morning to remember.
The following weekend, in bed, after playing with those majestic tits, I slid down between her legs. My tongue started on her pussy. "Does little Dougie Fineman want to please Mrs. Donaldson's pussy; her delicious pink pussy?"
She may have realized what she was doing, but at the moment I didn't. After all, my cock was hard and I was eating her delicious pink pussy. I was thinking with my cock again, not me brain.
I just kept eating; just like she'd instructed me. "That's it, Dougie, eat Mrs. Donaldson's pussy. Don't stop. Oooooooooh, oooooooooooh, oooooooooh, Dougie. I'm cummming, Mrs. Donaldson is cumming. I'm cumming."
Her pussy was delicious. When she finally dragged me up, "fuck, my pussy, Dougie, fuck Mrs. Donaldson's pussy," I thought for sure I was going to cum. I had another flashback.
Yes, a flashback to sixth-grader Dougie Fineman slipping his hand inside his pajamas, jerking off thinking of Mrs. Donaldson's pussy.
Diane brought me back to reality. "Fuck me, Dougie. You have Mrs. Donaldson's pussy so ready."
From then on whenever we got romantic, "Is little Dougie Fineman in the mood to please Mrs. Donaldson's delicious pink pussy?"
I didn't say anything; I just started on those spectacular tits. "Dougie, you know what Mrs. Donaldson needs." Gently she pushed my head down.
TO BE CONTINUED
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