Experience Ch. 01

Story Info
First steps on a sexual odyssey with sweet older woman.
2.7k words
4.11
53.9k
20

Part 1 of the 2 part series

Updated 10/16/2022
Created 03/05/2012
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I was not your ordinary kind of high-school geek. I didn't have the typical hallmarks that would get me voted "Least Likely To Lose His Virginity ... Ever" in the senior yearbook. I wasn't oversize or undersize, dressed fashionably enough, and had good personal hygiene. I wasn't into Star Trek or role-playing games. I wasn't in the marching band (and, consequently, didn't have any band-camp stories to bore my classmates with). I didn't have a weird family, wasn't very rich or very poor, and if you asked any of the other kids, they'd probably say I was fairly normal.

But, make no mistake, I was an oddball. I was tall and skinny, grew my blond hair to the middle of my back at a time when the buzz-cut was king. I listened to heavy metal when it was no longer cool and the preferred genre was hip-hop, which I hated. Other guys lived for video games; I could take 'em or leave 'em. Other kids went to the movies, but I always preferred books, and the teenage sitcoms that were popular at the time held no interest for me.

My grades were good enough to get me in to advanced-placement classes, but I didn't have the same attitude as the other nerds. I didn't work myself to death, stress myself out on purpose, didn't think being in A.P. classes made me somehow special, and, truth be told, didn't particularly enjoy schoolwork. My best subject wasn't science or math, but English, and yet, I didn't have the deadly-serious English-major mindset I would discover when I became one myself in college.

If it was possible for a geek to be a class clown, I was it. I cracked jokes constantly. I turned oral reports into comedy routines. I genuinely enjoyed making people laugh, but also, as with most class clowns, I did it to cover up my own shyness. I was so good at it that, then and now, people who knew me only casually refused to believe that I WAS shy.

I grew up without a constant male role model, but, with two sisters and lots of aunts, plenty of female ones. As a result, I didn't always relate well to guys my own age, being fairly indifferent to sports, and the typical locker-room talk about girls made me uncomfortable. I was gangbusters with the ladies, but only up to a point. I didn't know when to quit with the jokes and get serious and show another side of myself, or simply wasn't able to. My comedian persona was my shield; it attracted women, but also kept them at arm's length

Occasionally, a girl would show real interest, but by that point, I was so convinced it would never happen, I completely missed it when it did. One time, a girl I was friendly with walked up before history class and asked, point-blank, if I had a girlfriend. I must've gaped at her, because she added, "I'm taking a survey." She wasn't holding a clipboard or a notepad, and didn't write anything down when I told her I was indeed unattached.

"Sorry to disappoint you," I said.

She grinned. "Oh, I'm real disappointed," she said.

Golden opportunity. And I didn't do a goddamn thing about it.

Somehow, I got roped into being the statistician for the girls' basketball team. The coach, Mr. Steffens, was a neighbor and a friend of my uncle's, so he knew me, and I think, wanted to help me. But I didn't give a shit about basketball, and none of the players really interested me in a sexual or romantic way.

By that time, I had already just about given up on my own generation, and turned my attention to older women. My sisters' college friends, my mom's friends, a neighbor lady or two, and teachers. I could be comfortable around them, found it easier to talk to them, and could lust after them, safe in the knowledge that nothing would ever come of it.

I had my favorites. There was Stephanie, my sister's busty blonde roommate from Tennessee. There was a hot but somewhat trashy redhead named Debbie down the street. There was Serena, the flirty brunette who trimmed my hair, and there was Ginger, my six-foot-tall dental hygienist. There was my big-titted Spanish teacher, Diane Burkhart, who got animated and talked with her hands a lot, causing a rather well-known jiggling phenomenon. But my favorite fantasy woman was Rita Distefano.

Ah, Rita! She was my mom's friend, who had moved back into our area after her divorce, when I was a freshman. She was in her early 40's, and very attractive in a classy, low-key way. She stood an even five feet tall, with a trim figure and thick, curly black hair and big, dark eyes. Her nature was gentle, and she spoke in a soft, low-pitched voice, but I found I was often able to get her laughing long and loud, flashing big smiles, eyes sparkling. And she was an English teacher by trade (at another school), so we could talk about books.

When I was having some trouble with trigonometry as a junior, notes coming in the mail saying I was in danger of failing, Rita offered to tutor me. I managed an A, just barely, because Rita was a great tutor, and because I very much wanted to please her. When I showed her my report card at the end of the year ("Feast yer big brown eyes on this!" I crowed), she got the biggest smile, put her arms around me, gave me a squeeze and a kiss on the neck (all she could reach, because I was too surprised to bend down). "I'm so proud of you," she murmured, and kissed me again.

To say my blood was roaring after that little episode would be a gross understatement. And I figured Rita would probably find it pretty gross indeed if she knew, but even without the physical contact, she had become the star attraction in my sexual fantasies. For one thing, she was divorced, which made my fantasies more believable, made her seem somewhat more attainable than the married women I liked to entertain myself with.

She and my mom were tight enough that I knew when she had the occasional boyfriend. Sometimes, of a Saturday night, I would wonder, is Rita having sex right now? What position? Is she climaxing this very minute? Is some guy coming inside my Rita--squirt, squirt, squirt!--right this second? I tried to picture it, some teacher or lawyer or accountant humping away on top of Rita's small body. Or maybe she would be on top, perched on his hips, riding a large cock. I wondered if I might somehow be able to watch. That was the absolute best I could hope for, I figured. But of course, what I really wanted was to be the lucky man myself.

Then, after I'd finished masturbating, I'd sometimes give myself a vigorous noogie. "What the fuck are you doing, Kevin?" I'd ask myself. "You're nuts, pathetic, a moron, to be thinking like this! Pull your head out of your ass before you turn into a stalker or do something else to humiliate yourself. And DON'T, for Chrissake, say anything to Rita about it." And I'd be fine for a few days, get my rocks off thinking about Stephanie or Debbie or Serena or Ginger or Mrs. B. Sometimes, I'd think about Lisa Layton or Holly Porter, girls from school. But then, some afternoon, Rita would stop by to visit my mom, and I would find myself wandering out to the kitchen to say hi. Rita always seemed happy to see me, and would ask how school was going, what colleges I was applying for, and we'd talk about what books we were reading, what music we were listening to, and then she'd be right back in my fantasies.

A couple times, Mom had to run off to a doctor's appointment or to get her hair done, and Rita made like she was leaving too, but ended up staying around and talking with me.

It was the damnedest thing. So easy, so comfortable. When I got into conversations with girls at school, or on the back of the bus going to a basketball game, when I had run out of zingers and we'd start to actually TALK, I would get so nervous that I would tremble visibly. More than one girl asked if I was cold. How embarrassing! None of that with Rita. We talked about anything and everything, and the part that amazed me, even more than my own composure, was that Rita seemed to enjoy our talks as much as I did. I didn't get any more hugs, but sometimes, as she was getting ready to leave, I thought she might have wanted to. She usually settled for a pat on the shoulder.

I never told her that I was lonely, but I think she could tell.

As my senior year went by, it was beginning to seem like Rita was just as much my friend as she was my mom's. And I was coming out of my shell and flirting a little bit with her. She seemed flattered, would give me her big smile, squeeze my hand and say, "You're sweet ..." and sometimes hang on a little longer than normal.

Her touch inflamed me.

One day, I recounted a squabble Mom and I had gotten into earlier about my hair. She wanted me to cut it short, thought it was a phase I should have "outgrown" by now. I thought my long hair had become a part of me. Rita was in my corner; her attitudes were a bit more liberal than my mom's. "Maybe someday you'll decide it's time to cut it on your own," she said. "You'll know when the time is right. Besides," she said, reaching out and lightly stroking my hair, "it's beautiful."

I blushed. "Well, it's me," was all I could think to say.

Her fingers kept moving through my hair. "It sure is," she said.

Touch me, please, touch me, I begged silently.

But she took her hand back, and we went on as normal.

A couple weeks later, I got up my nerve to try steering the conversation in a more sexual direction. We were talking about books again, just me and Rita in my living room, my mom off having her roots done (at 42, she'd been coloring her hair for several years). I mentioned I had been reading Stephen King's "The Stand," which got Rita going about what a classic it was. When she started to wind down, I said, "I'm about halfway through, but I got sidetracked last weekend. Found this book in Rachel's room," referring to my sister, who was away at college. I snickered to myself, using the extra two seconds to ready myself before taking the plunge. "Jackie Collins," I said.

Rita looked startled for a second, and then a small, mischievous grin curled her lips. "I bet you DID get sidetracked," she said.

I tried to grin back in a way I thought was sheepish, and not creepy and pervy. "Yeah," I said. "Purely for literary research purposes."

Now Rita laughed. "You liar," she said, swatting my shoulder with evident fondness. "You just wanted to read the dirty parts."

Which was of course true. The incident in question had actually occurred the previous summer, and not just days ago, like I was making out, but I had decided to alter a few small facts for my present needs.

"No, really," I protested. "I was studying it in a scholarly way."

"Really," Rita said skeptically.

I crossed my heart, making her laugh again.

"And what literary conclusions did you come to?" she asked. Was there an extra emphasis on the word "come?"

"Uh," I said, and paused. Shit, now what? I hadn't thought this thing out very well. Then I blurted, "I think she writes sex scenes like a dude." I had no idea where this came from, it just popped into my head. But after I said it, I realized it was true. "People are always screaming and flailing around and knocking lamps off the bedside table," I went on, warming to my subject. "It just seems so overblown and unrealistic."

Rita considered, and admitted that I had a point. "But," she said, "I guess it depends on how excited you get, how turned on you are."

All right, I thought, now we're cookin' with gas! liquid propane, maybe, or lighter fluid. She could just as easily said something about the role of fantasy in fiction.

"And then," I said, not sure I dared share one of my more favorite passages, "there's this part where the woman's on top, and it describes her 'riding him furiously, her breasts bobbing wildly.'" I made exaggerated juggling motions with my hands on front of my chest. I grinned, probably a bit maniacally, but inside, I felt like I was walking a tightrope, about to take a nosedive any second. One false step, and by the time I knew it, it would be too late.

Rita burst out laughing, but then sobered and said, "Well, again, it depends. She could be pretty ... energetic." She seemed to be searching for the right words. "You know, when you're ... near the end ... things can get prewtty ... wild." She laughed again. "They wouldn't even have to be that big," she said. "The boobs, I mean." I thought I caught her glancing down at her own chest.

Oh my God! Did that ever put an image in my mind: Rita on top of me, nearing orgasm, with her mouth open in some sound of ecstasy and her bare breasts bouncing.

I suddenly felt I needed to lighten the mood. This was getting deeper than I'd expected, and I began to flounder toward shore. Some comic relief should do it.

"And then there's one part, where she's doing this young English guy, and right when he, uh ..." Shit! Back in the deep water again. "When he's about to, you know, climax ..." Whew! Was that so tough? "He yells out ..." I put on a thick British accent. "Gorblimey! Oy'm comin' so fahst it's loik a bleedin' express train runnin' through me cock!"

Oh my God! I just said "cock" in front of Rita! I was so busy doing the accent, I'd forgotten what I was actually saying. Now I'd blown it for sure!

Rita threw back her head and laughed. "Oh my God!" she cried. "You are hilarious!" She laughed some more. "And you're right," she said when she'd calmed down again, "that is horrible dialogue. Just awful!"

"I know it," I said. "I sure wouldn't be able to string that many words together at that moment, without a bunch of them being your name, or just 'Oh!'."

Your name? Not "the girl's name," or "the name of the woman I'm with," but "your name?" Nice going, Kevin, you just can't find your way out of this one.

But Rita was still chuckling and maybe missed it. Or maybe not.

Somehow, the conversation found its way to safer territory. After a few more minutes, Rita grabbed my hand, in order to look at my watch. But I noticed her fingers wrapping around mine quite securely.

"Oh, it's almost six o'clock!" she said. "Your mom'll be home any time now. If I'm still here, she'll think we were doing something naughty while she was gone." She winked and squeezed my hand, but didn't make a move to get up.

"But we were discussing literature," I said, squeezing back, not wanting to let go, imagiing that same hand roaming my body.

"We sure were, honey," she said, smiling at me, giving my hand another squeeze. "We sure were." This time she did stand up, pulling me with her. We walked to the door, still holding hands. Finally, she had to let go to put on her coat.

"Keep reading that scholarly literature," she said, still smiling. She turned her shoulders to the left, then to the right, then left again, then right. Was she just getting her coat situated, or was she ... actually ... giving me a little boob-shake? With the coat, it was impossible to tell. I'm sure my own intentions were more obvious, as just the thought of her possibly jiggling her tits at me was causing some stirring in my jeans. But she was patting me on the arm and telling me bye, see you soon.

As I rushed off to the bathroom to take care of some urgent business, I hoped it would be very soon indeed.

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5 Comments
cricketxcricketxover 10 years ago
No sex but very very good

No sex but very very good. Exceptional dialog and moved at a very fine pace.

GrimsbainGrimsbainabout 12 years ago
Liked it so far...

I like this story so far even with no action in the first part. Looking forward to the next part.

AnonymousAnonymousabout 12 years ago
Good Start

A good start and I'm looking forward to the rest

bruce1971bruce1971about 12 years ago
Nice

Unique characters, a slow build, this is very promising!

AnonymousAnonymousabout 12 years ago
Nice Start

You’re off to a great start; I look forward to that first liaison with Rita.

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