Assmates: A Blast Into The Past

I spend way too much of my time hunched over the computer in my home office chatting, looking at and reading erotica, and living an extremely proactive fantasy life.

I've often thought that were I to experience some sort of actual fulfillment of those fantasies, it would come via meeting someone in an AOL chat or something of that ilk, and in a way I guess I was right. In reality, though, it happened through a much more apparently innocent set of circumstances.

Three months ago, I came across a website which is an online database of high school alumni. My class, from my high school, is particularly active there. Fully 80% of our class has registered and is available for chat or e-mail via this service.

I have reconnected with dozens of friends and former classmates, all in all a terrific experience. Most extraordinary, however, is the meaningful exchanges I have had with people I wasn't particularly close to in school, but through some shared experience or similar life circumstance, now find I share some stronger relationship.

The deepest of these post-school connections came with Sharon, who was a shy, studious, and beautiful member of the modern dance team in school. We had been in mutual classes, but while she was in a popular clique, I was a class-cutting, smoke-in-the-can, class clown. We knew each other, but we never spent much time hanging out.

Unbeknownst to her, she was the subject of a daily adolescent fantasy for me our junior year. She sat in the desk directly in front of me in Physics. Every morning at 9:04 she would slip into the chair behind her desk, the freshly showered and perfumed scent of her would waft over me, which would've been enough in and of itself. But, and I ought to say "butt", it was her ass that drove me wild.

Her incredible rear end would slide back against the chair back support and the thin, single steel bar would accentuate the natural crevice between her cheeks, pulling her skirt or pants taut around her perfect hips.

For an adolescent 16 year old, the effect was as riveting as the Food Network to a starving man. The unrequited arousal was the star of nearly every fantasy, and the focus of my every masturbation for the entire year. I was fortunate to even pass the class. Only my fear of her disapproval and the possibility of being dropped from the class kept me from ignoring the subject matter entirely. I am sure that my current fetish for a great ass has its root in those first period fantasies.

All this was squeezed from the recesses of my mind when I received an e-mail notice from that alumni site, which originated from her. Delighted, excited and with her still being a nubile 17 year old in my mind, I read that e-mail as if it were a Publisher's Clearinghouse notice. What are the chances really? How can I possibly be so lucky? This must be some sort of extravagant ploy by a soon to be ex-friend from high school. I couldn't believe that out of the 200+ classmates, she had remembered me distinctly enough to e-mail me. I wouldn't have thought she would've remembered me at all.

We exchanged several friendly e-mails, updating each other about our current lives, spouses, kids, jobs, etc. I told her I now lived in South Florida; she still lived in a suburb of New York. We laughed over old friends and teachers, and I probably said in closing once or twice, "Well, if you're ever in South Florida..." or something along those lines. But after half a dozen conversations, the thread just petered out.

After not having heard from her in a couple weeks, I had gotten the old yearbook out and her sweet young face and body in those 15-year-old pictures brought back more than memories. I could picture that ass in that chair so clearly that my crotch started to twitch. I adjusted myself in my pants, rubbed myself a little and would've consummated the fantasy if the phone hadn't suddenly rung. "Hi..it's me...Sharon."

"I was just thinking about you!" I said, totally honestly, while smiling to myself and rezipping my fly, "What are you up to?"

"Well, I am down here in Miami for a convention and I have the night free. I was hoping you would like to have dinner or a drink or something?"

And just like that, I was showered, shaved and cruising down I-95 headed for her hotel. I walked into the lobby, found the bank of elevators and headed for her room on the 12th floor. It seemed to take hours to traverse those twelve stories. What would she look like? What would she be wearing? How much older did the 10 lbs more weight and 10 lbs less hair make me look? We had decided on going casual and just getting together to relive old memories, so I wasn't dressed to the nines, just a white Oxford dress shirt and a pair of pressed khakis. When I knocked on the door, and I heard the lock click, I caught my breath and waited with anticipation.

I can't say she hadn't changed a bit since high school. She was more beautiful than ever. She had the beautiful face of a woman, in place of her sweet girlish face, but her body had aged like a fine wine. I had known that her career as a choreographer would've kept her in great shape, but I wasn't prepared for the physical perfection that was framed by the doorway. Her breasts, which I had remembered as sweet little handfuls, had blossomed into magnificent orbs of perfection, barely contained by the tight, low cut, black dance leotard she wore tucked into a classic pair of jeans.

"I'm so happy you were free tonight!" she gushed as she hugged me and pressed herself tightly against me, "Why don't you come in?"

As she turned and walked back into the room, I got my first look at the object of my erection. Every curve, every crevice, every nuance was exactly as I remembered.

"I'm gonna have a beer, do you want something?" she asked as she bent down to open the courtesy fridge. "Sure...a beer", I stammered as she showcased that perfect rear end. "Rolling Rock", she giggled, "Just like the old days!"

She handed me the ice-cold beer, which had been a staple of every high school party we'd ever been to. She bounced down on the edge of the bed, and I sat in the desk chair that faced her. She smiled at me and I took a long draw on the ice-cold beer.

"So," I offered, "I have one big question."

"Shoot."

"What made you e-mail me in the first place? Not that I mind, but it wasn't like we were best buds in school."

She blushed a little, "Do you remember Melinda Castro?"

I nodded my head. I did. Mel had been my prom date and one of Sharon's best friends. She was a sweet, bright, and hilarious girl, but was kind of heavy and somewhat ordinary looking. My initial prom date had had an emergency appendectomy the week before the prom, and Mel hadn't been asked. I remembered asking Mel, and going the whole nine yards, with her. Flowers, limo, acted like a real gentlemen. Even though she wasn't my first choice, I had treated her like she was. Took her out to all the after-parties, doted on her and treated her like a princess. I had figured that if my prom couldn't be everything I wanted, at least her's could be.

"The way you treated her, making it the best night of her life, and taking her home later when she got so drunk, without taking advantage of her...well, I always thought it was the sweetest thing I ever saw a guy do."

I smiled, "I remember. When I kissed her goodnight, I think it was her first kiss...Half of me was worried that she would mistake a great night for something more than that. I was hoping she would appreciate the great night for what it was. It turned out we were both just happy she didn't get in trouble when she came home so drunk!"

Sharon smiled at me, "At our 10 year reunion, she said the way you treated her was her best high school memory and that it was still the best kiss she ever had. She was so disappointed that you weren't there. I always promised myself that if I ever had the chance, I'd find out for myself. If you'd bothered to show up, this might have happened there!"

And with that, she put her hand on my cheek and leaned in to kiss me...the sweetest, softest, little kiss. As I kissed her back her lips parted ever so softly, inviting me to kiss her more passionately. Our tongues tips brushed, I gently licked her lower lip and sucked in gently between mine. "Oh my!", she whispered, as I lifted my head from hers and gently ran my fingers through her hair and we looked in each other's eyes.

"I have a confession to make, too." I breathed, feeling a lot more confident right now than I did fifteen years ago.

"Remembering something from Physics?" She laughed, as her eyes sparkled, "I'm so sorry I tortured you so badly back then."

I was dumbstruck. "You...you knew?" I stammered.

"Knew? Of course I knew. Did you think I usually rub my ass on a chair back for 40 minutes every morning? Of course I knew. Everyone knew. You looked like you had a flashlight in your pocket every day on the way out of class!" She had a good laugh at my expense.

I flushed with equal parts embarrassment and arousal. She stood in front of me and turned around, with her perfect ass just inches from my face. "Does it still meet with your approval?" She purred as she undid the front snap and pulled her jeans slowly down over her hips. The black leotard was cut with a deep V down her back and high over her hips so that both cheeks of her incredible ass were exposed to my view. The tight cotton Lycra fabric hugged her so tightly I could see the definition of her taut dancer's muscles move as she pulled first one leg and the other out of her jeans.

I sat mesmerized. She slowly and gracefully bent at the waist, her long fingers tracing lines down the backs of her naked, muscular legs. Her legs were perfectly straight as she held her ankles and grinned up at me from between them, "I don't dance as much as I used to...but I think it's still in pretty good shape." Her eyes twinkled, "Are you just going to look at it? Or are you going to see if it's everything you imagined?"

In a trance, my hands slowly reached forward, one palm gently touching each of her cheeks, and slowly caressing them. She raised her head and rested her elbows on the bed, her legs slightly spread but still perfectly straight. I could feel how tight the muscles of her ass were, and could see there was nothing between it and me except a thin layer of Lycra and the 4 or 5 inches of airspace that separated us.

I lifted the leg bands of her leotard ever so slightly with my thumbs, pulling the thin cloth between her legs and ass cheeks taut and heard her gasp as I pulled it higher and tighter and ran it between her cheeks and swollen lips with my finger. I could see the fabric darken with her wetness as my fingertip softly caressed the Lycra. I moved my face close to her magnificent ass and ran the tip of my tongue gently up the inner curve of her left ass cheek. She gasped and pushed her hips back towards me, silently begging for more.

I leaned back, and still holding the bunched Lycra, took my keyring from my pocket and opened the small pocketknife on it. Pulling the Lycra taut, I sliced it. The tight elastic fabric snapped away, exposing her to me.

She was completely shaved. Her engorged lips spread open right before my eyes, glistening with wetness, begging for my tongue. But I had another target in mind.

Using both my hands, I spread her ass apart, exposing the perfect pink rosebud between her cheeks. I pressed my mouth against it and drew little circles around it with my tongue.

"Oh...God...yes!" she breathed, pressing her ass against my face. My tongue licked up from her wetness, tasting her for the first time, and pressed against her sweet tight ass. Her tiny hole tensed at the pressure, then parted, letting my tongue dart in and out. For what seemed an eternity, I slowly tongued her butt, my rock hard cock oozing in my pants. I could feel her ass squeezing my tongue. I slowly rubbed her clit with my right hand as my tongue moved in and out of her ass, my hand drenched with her juices. I slid my thumb inside her and felt her pussy clench tightly around it she came.

She spun around as gracefully as you would expect a dancer to and in a single deft move, dropped to her knees in front of me. I lifted my hips as she pulled my pants off, freeing my rock hard cock. She wrapped her hand around the shaft and looked up at me. "You aren't the olny who fantasized about this", she murmured as she slowly rubbed my hard cock, and with out ever breaking eye contact she took the head of my cock in her mouth, and slowly took my whole shaft into her throat. Her hand rubbed my balls gently as she buried her nose all the way into my pubic hair. Her throat swallowing repeatedly, squeezing my shaft, which was, buried deep in her mouth. Her saliva dripped from the corners of her mouth, running in little rivers around my swollen sack and dripping down my ass crack. She starting fucking my cock with her mouth, while her finger rubbed my ass. I felt my muscles clench and I knew I was going to cum.

"Oh God...Sharon...I'm cumming", in one deep swallow she buried my whole cock in her throat again as she slipped her finger in my ass. I started to shoot like never before. Spurt after spurt. 15 years of orgasms wrapped into the biggest load I had ever shot. She swallowed every drop. Never pausing, she started sucking the head of my cock gently. Rubbing my shaft keeping it hard, still looking at me. She let the head of my cock pop out of her mouth. Her lips glistening with my cum, "I know you want to fuck my ass...will you please? I have never let anyone before...I've been saving it for you."

She got up and bent over the table. I stood and reached under her sticking my fingers into her wetness. I smeared her juice up between her cheeks, massaging it into her tight little ass. As I spread her ass cheeks with my hands, I first slammed my cock into her soaking pussy, hard and fast. She yelped, with surprise, as I hammered hard with 3 or 4 fast strokes. I pulled out and was covered with her juices. I let my shaft rub against the crevice between her cheeks like I had watched that steel bar do so many times, so many years ago.

She reached back and pulled her ass cheeks apart as I pressed the head of my cock against her asshole. "Gentle...gentle...this is my first time", she whimpered as I pressed harder. Her tight little hole spread open and the head of my cock popped in. "Oh God!!" she screamed.

I paused a moment before rocking gently easing a little more of my cock inside her. I heard her grunting as each little thrust moved me slightly deeper inside her. Suddenly, I felt her ass loosen and let another inch or two in all at once. She simultaneously moaned with a deep guttural sound I'd never heard before. I pulled back until just the head of my cock was in her and thrust more forcibly...deeply into her. As deep as I had been moments before...and then deeper.

"No...careful...No!....Yes!Yes!" she screamed as her ass muscles finally loosened again, and I buried myself into her as deeply as I could. I slowly began to fuck her tight ass. I have never had my cock squeezed like that before. I started stabbing deeply into her with long strokes. All the way out and then plunging all the way in. She was pounding her fist on the table, begging for me to fuck her harder. I complied. I could hear the table slamming against the wall as I thrust against her, sweating, grunting, holding her hips with my finger tips as the palms of my hands spread her ass open wide.

"I'm cumming, baby, I cumming!" she screamed and when she came her ass clenched my cock so hard, that I came too. My hot load shooting in her ass as she ground against my pelvis. With each hot spurt, her ass clenched my cock tighter, squeezing and sucking every drop of cum from my shaft. I slowly rocked my hypersensitive rod in and out of her, I could feeling her trembling with pleasure with each slow, pleasure filled, thrust. I finally recognized that this was a fifteen year old fantasy cum true.

We staggered over to the bed as I slipped out of her and we lay there spooned. My limp cock pressed against her ass and she fell into a deep, blissful, sleep. As I held her sleeping body, and buried my face in the sweet smells of her hair, I knew that later we would make love again, but that this one had been for me. A payback for the good karma I had unknowingly put in place so many years before.