Homecumming - When Dolly Met Jeff

Jeff West was a total heartthrob and went to my school.  But he was a senior when I was in seventh grade, so it’s not like we could have dated.  Or that he even knew my name.  He was the football team quarterback, was the point guard on the basketball team, and did a variety of track and field events.  He went on the do the decathlon in college and finished just short of making an Olympic team at the trials, and then he went into the family real estate business in my community.  So you’re wondering, why is Dolly bothering to tell us about some dude she didn’t hook up with who sounds like everyone’s All-American when what we really want from Dolly’s blog is hot stories of her sexploits?

I didn’t say I NEVER got to enjoy Jeff West.  Just not when I was a seventh grader going to my friends’ Bar and Bat Mitzvah parties (I learned that when the thirteen year old is a girl, you use the word Bat, pronounced “Baht”, and when it’s a boy, then you use “Bar”) as a thirteen year old.

Didn’t any of you handsome gents ever go to your school’s Homecoming?  <Wink!!>

So again, Jeff was five years older than me, and I felt about as invisible to him as Molly Ringwald felt around Jake for most of Sixteen Candles. 

I guess the four years from age thirteen to seventeen must have been good to me.  (Blushing with false modesty).  Our football stands were filled, I was doing some flips as a cheerleader, and as we finished our cheer and I went back to my pom-poms, I saw Jeff shaking hands with the director of athletics, the track coach, the principal, the PTA President…everyone who was anyone wanted to see Jeff and be seen with Jeff.  I think God himself might have waited a turn to shake the boy’s hand.  He was THAT popular.

About the PTA President, Melissa Renzuli’s mother Angela:  Unbeknownst to her, she is a role model of mine.  Kept her University of Florida cheerleader figure, had a visibly happy marriage, maintained her social standing, and never missed any of her family events or community volunteering commitments, and only much later did I find out that she was fucking her husband’s boss, as well as her personal trainer, her banker, Jeff’s dad, and on a few occasions, Jeff.  She was a cougar before any of us knew the sexual meaning of the word. 

When I later found out that she’d seduced Jeff, that made sense to me but at the Homecoming game, the soft peck on the cheek didn’t look out of place at all, just what a warm wholesome mom does when she’s affectionate.  Damn, Angela Renzuli had it going on.  But back to Homecoming.

So I feel my heart skip a beat, feel my pussy moisten, and imagine if Jeff had been one of the sex partners I’d been with by that time, when I was a seventeen year old HS junior.  And then my heart stopped when Jeff, a few handshakes later, looked out toward the field, observing a player one of the administrators was telling him to take a look at, and his eyes scanned back from the field and stopped on me.  ME!  And I saw him take notice, eyebrows up, smile, and then….a wave.  He waved.  To me!

My eyes must have shown terror, and here was my second Sixteen Candles moment:  he mouthed, “yes, you” just like Jake did from across the street after the wedding. C’mon, it’s not just a chick flick, it’s a teen flick, you’ve all seen the movie, haven’t you?  Well if not, now that you know I like it, maybe when we have our next Dolly Date we can watch it online streaming and act out what we think Farmer Ted the Geek did with Ginny the popular girl in Jake’s Dad’s Rolls Royce.

Back to When Dolly Met Jeff.  Homecumming.  Yes, as I smiled back to the “yes, you” and mouthed, “Hi” and winked, I thought to myself that Homecumming should be spelled with a “U” like that.  Because I was getting wetter.  And Jeff was making his way down the bleachers to the front, in front of where we were.  Not sure I ever had a faster heartbeat during any races, marathons, triathlons, ever.  This was my adolescent crush, looking even better than I remembered, heading my way. 

“I’m Jeff.”

“I know.” (Could have kicked myself.  I was already sexually experienced and talented, and here I was, in hero worship fan-girl mode again.)

He laughed.  “I’m flattered.  I used to go here.  Someone said your name is Dolly, did they tell me that correctly?”

Fuck he was good.  Pulled me back from the humiliation of “I know” in a split second to make me feel wanted.  Only later in the afterglow did I find out who told him my name.  Angela Renzuli.  Seems the whispering before the peck on the cheek included Jeff asking if she was busy after the game, Angela letting him know her husband and children were all there and that she couldn’t that night but that she’d make it up to him, and she whispered something like “third cheerleader from the right, front row, Dolly, she’s seventeen.”

I still send holiday cards to Angela Renzuli, that dear sexy cougar.  Bless her heart.

“Yes, I’m Dolly.  I remember when you were here.  Everyone does.”

He blushed.  I made Jeff West blush.  And he was making my pussy gush.

“I’m not doing anything after the game,” I blurted out.  Everyone in the marching band heard me.  Not that any band geeks stood a chance with me.  Well, except for the couple guys who were in my study groups for a couple of honors classes.  Funny how when they’re all in a group in dorky uniforms they’re “band geeks”, and when they’re in regular clothes, one on one, they’re regular guys and if they’re nice and helpful, that’s attractive and turns me on.  But the only instrument going in my mouth that night wasn’t a saxophone, it was going to be Jeff West’s tool.

“I’ll find you.”

Yes, it was that easy.  No prescreening or references.  Simpler times, my youth.

After celebrating the victory, doing the post-game cheers, and all the post-game hugs and call you tomorrows, I spotted Jeff, still shaking hands, getting hugs (including another from Angela Renzuli.  Slut had good taste, I admire that about her, too. She’d been his first.  Lucky bitch). He told me we could come back for my car.  Of course I was safe, this was Jeff West. 

Who was I kidding.  He was the one who was in danger.  I was well on my way to becoming the Dolly Jewel who offers so much happiness to me these days.  But I hopped in his car and off we drove into the south Florida night, warm, humid….kinda like my pussy was feeling.

He offered me a beer when we got to the portside park near where my daddy’s friends docked the yachts we’d built for them.  Jeff had a beer cooler full of ice and long necks in the trunk of his Mustang. I asked him if he had any wine.  He confessed no, and asked if that was a deal breaker.  My answer was to lean over, put a hand on his thigh, bring my lips to his, and find the outline of his cock while his tongue made itself at home in my mouth. More kissing, I progressed from tracing to rubbing and his hand cupped my breast and I grabbed that hand not to stop him but rather to place it fully on my breast and moan, “God yes, touch me, take me” into his mouth.  Never play coy with the first boy you ever thought about as your masturbation fantasy while frigging yourself when the amazing day comes that you’re actually with Mr. Fantasy Frig.

I was starting to un-do his belt when he said, “we should go someplace private, I can drive us to a hotel.”

I took my hands off his pants long enough to gently hold his face as I passionately kissed him and then whispered, “how about a yacht?’

Felt his cock throb.  Yes, I impressed Jeff West!

Janie McAlister and I had been friends forever and her father Doug McAlister’s yacht was close by, and she and I had been on it so many times and I knew how to get in and I also knew that Janie and her family weren’t going to be here that night.  Wouldn’t have been the first time I’d orgasm’d on that yacht.  But as to whether it was cute Janie, the pixie tennis player with the tight body, perky personality and blue eyes, or her daddy, Doug, a slightly less than fit but always charming man with green eyes and a great smile and an unsuspecting wife, I’ll save for another story.  Or was it both of them?  I’m such a tease.

I led Jeff by the hand, and we boarded at the stern, made our way up to the wheelhouse and entered from the outside up there, then down a spiral staircase.  I knelt and took Jeff’s cock out and licked the length of the underside of his cock in the lower lounge, a main gathering place with a huge comfy sectional I’d been fucked on before. Then I took the head of his cock in my lips, and swirled my tongue, and took as much into my throat as I could without gagging.  I wasn’t as through a deep-throater in those early Dolly days. But he wasn’t complaining, he was moaning, rocking back and forth, stroking my long blonde hair.  I was sucking Jeff West’s cock!

“Wait, wait, I want to save it, don’t make me cum in your mouth, Dolly, it feels so good, you’re so beautiful.”

Guys—telling a girl she is beautiful when she’d got you in her mouth scores major points.  Most guys say “hot” or “sexy” if they can think clearly enough to form words.  Jeff said “beautiful”.  God I was ready to give myself to him completely when I heard that.

And I might have.  I had a wispy thin landing strip, these were the earlier days of trimming and I wasn’t fully hairless yet downstairs as I enjoy being today.  I had this image of his raw, powerful, hard flesh directly in me.  Imagining his hot cum splashing all over the inside of my love hole.  And yes, the word “love” was in my mind.  Complete teen irrational fantasy cumming true.  He half took our own clothes off, and half stripped each other, kissing and touching and groping and oh God, whatever else he wanted to do.  I’d have detailed his Mustang for him if he asked, if only he’d fuck me.  I think my body was preparing for impregnation when he grabbed his jeans from the floor and recovered a condom from the pocket.  It didn’t quite register to me that he’d brought condom to the game, that cocky handsome devil.  But that’s okay, turned out he hadn’t.  You guessed it.  Angela slipped him one from the secret compartment in her purse when he made his way back into the bleachers after saying he’d meet me after the game.  And then she went home, fucked her husband good and long, all the while thinking of Jeff.  And me.  I squirted when she told me that some months later, while she was going down on me after gently tying my wrists to the bed posts with scarves.  And Jeff was taking her doggy style, smiling at me while she told me that.  Sorry, getting ahead of myself again.

I told him that I wanted him to use that condom under the stars, and led him outside, this time near the bow, facing away from the dock, and we went up to the sky deck, where a padded cover had been placed over the hot tub. 

Jeff’s fingers worked me off to my first pop of the night, and his lips and fingers partnered for number two, and then I rolled the condom on his cock after sucking him back to bursting, and I opened my legs for this smooth muscular chested athletic handsome dreamboat.  Like a hot knife into butter, slid in, well lubed, deep, until his bottomed out, slowly, gently and tenderly. He looked in my eyes, motionless, while I adjusted to how it felt to be full of…Jeff.  I whispered his name, “Jeff”.  He kissed me, softly at first, and then building slowly, passionately, the heat building and his rocking and rhythm increasing and soon I had hooked one leg around his hip and he threw my other leg over his shoulder.  I couldn’t decide where I wanted my free hand, the one he didn’t have pinned to the firm cushion beneath me, whether to grab his tight butt and pull him into me, or around his waist, or up to his shoulder and just try to hold on for dear life.

Even the finest athletes can get winded.  He slowed, his breathing was so heavy, and again, he told me I was beautiful.  “Let me be on top of you, Jeff, I want to ride you.” You think girls love being told they’re beautiful?  Men love women saying they want to ride them.

We both giggled as we each noticed that we’d had the same idea without discussing it.  We moved slowly and carefully to swap positions, top for bottom, without dismounting.

I leaned back and felt his cock hit my g-spot.  I put my hands on his chest when I leaned forward to kiss him.  A great kisser.  His hands either assisted my ass in bounding up and down on his rod, or else they fully engulfed my tits and tweaked my nipples.  I threw my head back and looked at the stars and moaned and cried out as I came.  I’m sure that brought out some inquiring eyes, but who cared, I was making love with Jeff West.

Yes, you read that right.  I thought this was making love.  I was young.  It wasn’t, but it was tender, sensual, and caring.  Just because its only sex doesn’t mean you can’t try to make your lover feel like the center of the universe for the time(s) you’re together. He never hurt my feelings when we stopped having sex a couple years later.  We became fuck buddies of the first order.  We shared Angela.  I eventually got all of the scoop on Angela from Jeff, Angela herself, and that banker she was fucking, who also financed many of the yachts my daddy’s company sold.  Yes, I slept with the banker eventually too.  And then told Angela all about during a nude hot tub interlude with her.  Like I said, she’s something of a hero of mine.  Or did I say role model?

Jeff eventually filled the condom doing me in a seated reverse cowgirl overlooking the bay, lights flittering all around off the water from the high rises.   He kissed my back, then collapsed, sweaty and spent, onto his own back.  I waited until he softened enough to slip out, then I moved over and snuggled next to him.

So that’s my favorite “Homecumming” story.

One I got to re-live.  Not just on future sexual encounters with Jeff.  Or Angela, who he told all about it step by step, blow by blow the next time they hooked up.  Nope, that wasn’t all.  I got to re-live it when I hooked up with Doug McAlister a week later when Janie and her mom went to take a tour of Vanderbilt.  Not that I’m saying just getting laid on the yacht was re-living it.  But when Doug turned on the monitor and showed me the yacht’s security cameras had recorded the entire evening with Jeff, including in night vision on the top deck, I felt so dirty.  In the best meaning of that word possible!

Happy Homecumming everyone.


Purely fictional fantasy for your reading pleasure!

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