When Allen Met Jill

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His long-awaited first time isn't quite what he expected.
5.9k words
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Part 1 of the 2 part series

Updated 09/22/2022
Created 02/25/2003
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The first girl Allen ever had a crush on was a curly-haired blonde sixth-grader named Candy. They were both twelve years old, they were both just starting to feel the onset of the approaching hormone storms, and Candy had no idea that Allen had a crush on her. Allen really had no idea why he had a crush on Candy, either; in later years he figured it came from the day in class when he had been walking back from the pencil sharpener past Candy's desk while she was leaning over to pick up a dropped eraser and by pure happenstance got an el primo peek directly down the front of her blouse. He hadn't been trying to look down her blouse, and even if he'd really known the full significance of what he was looking at, there wasn't much there, because Candy was only twelve years old, for God's sake. Besides, it wasn't a frozen prepubescent tableau; it couldn't have lasted more than half a second. And even if he had had the chance to stand there and feel her up with his eyes, he'd never have been able to do it. Allen, you see, was shy. And after he worked up the courage to tell Candy that he "liked her-liked her," and she replied by calling him "Pruneface" for the rest of the semester and regularly sprinkling pencil shavings in his baloney sandwiches, his bashfulness grew to neurotic proportions.

Two years later Allen was sitting in science class trying to pretend that mass displacement in liquid media was as captivating as the NBA playoffs when his teacher, Mr. Comstock, announced the long awaited and dreaded science project. Mr. Comstock, like all junior high school teachers, loved to make his students pair up into teams, and also loved to pair up boys with girls. Allen didn't know whether Mr. Comstock wasn't getting enough at home or whether he just got his jollies from adolescent awkwardness. Mostly he just wished the science teacher would find some liquid medium someplace and use himself to displace some of it. It was bad enough that everybody was silently, furtively laughing at him on a daily basis for reasons they tauntingly kept to themselves, but which he was SURE was his bashfulness around girls - now he was being forced to team up with…a girl! Terror welled up within him. What was he going to say to her? How was he going to get through this project? Oh, the life of an eighth grader is truly the toughest plight of all.

Time passes quickly during an anxiety attack, and by the time Allen managed to refocus, Mr. Comstock had reached the “G’s” on the class roster. "Grosserhahn!" "Um, yes, sir?" "You're with Miss Miller." Allen looked around, the name not striking him as being familiar.

Then he saw her, and his heart skipped a beat. She was beautiful - tall, with long brunette hair, big limpid blue eyes, an absolutely angelic smile, and the fixings of a small but firm bust. She was new, her family having just moved to town the previous summer. He hadn't met her previously, but he had heard through the grapevine that she was very nice and was very easily embarrassed.

"Hi," she said softly, "My name is Jill."

"Um, hi. I'm Groslen Alhahn. I mean I'm Hahnal Algrosser. I mean-"

His stammering was interrupted by a nervous giggle from Jill, which simultaneously entranced and humiliated him. Without thinking, he blurted, "Is it true your nickname is H.H.?" This meant 'the Happy Hooker,' one of the primary monikers used to tease Jill, or so he'd also heard.

That cut off her giggle in mid-throat, if not her own nervousness. "No," she replied, blushing furiously.

"Oh," murmured Allen, "sorry. I didn't really think you were one. A hooker, I mean." Oh, great, he chided himself, you just meet the nicest, prettiest girl you've ever seen, even if it is only as your science project buddy, and you're discussing her future career in the red light district. Come on, man, you can do better than this!

"Um, so, anyway, what project were we assigned?"

"Weren't you paying attention?" Jill asked.

"Er, ah, well, no."

"Well, it's okay, I took notes. You can look at them if you want. We'll be doing the one where you use a dill pickle to power a light bulb."

"Oh," opined Allen. "I was hoping for the one where you light a paper towel on fire inside a milk bottle and it sucks a hardboiled egg in the top. It makes a really cool sucking sound." Oh, crap, he thought, I just said "sucking" in front of her!

"Yes, well, we got this other one," Jill drawled, appearing to be losing interest in the exchange. "I've got light bulbs at home. Can you provide the pickle?"

Allen snorted a loogie halfway across the room to splatter against the front of Mr. Comstock's desk, which he covered by pretending to have sneezed. Great, he thought, the one good thing I've done is not blow boogers in Jill's face. When, in his deepest heart of hearts, what he wanted to do was kiss that face all over - and not stop there.

But such thoughts never got out of his deepest heart of hearts, and so he and Jill went on to collaborate on their pickle bulb project without incident, good or bad. The two got to where they weren't mortified in each other's presence any more, and actually came to be something like friends. Which, for junior high school, was more than sufficient.

But as the next few years passed, what seemed to still be sufficient for Jill was becoming manifestly insufficient for Allen. They were both good students, so they shared many of the same classes and were both in Honor Society and other activities together. They had many of the same friends, so they ran around in the same social settings. But they never had any real time alone together - not because Jill wasn't open to the possibility so far as Allen knew, but because he didn't dare take the risk of asking her out.

It really was a pathetic state of affairs, and it was all the worse for Allen's acute awareness of it. He was in love with Jill, or infatuated at the very least. He longed to be with her in any setting. He would go to places where he knew she'd be walking by and act like he just happened to run into her just so he could say hi. But actually asking her out on a date was out of the question. Even the slightest chance that she'd point and laugh and call him "Baby Dill" the rest of the semester was too much to take. It was an intolerable situation that was bordering on obsession.

The school year came to an end, and he went with his dad on the annual trip to Ohio to visit his grandmother. And he got an idea: he would write Jill a letter. Yeah, that was the ticket - a nice, friendly letter sharing with her what was going on with his summer and asking her what she was doing, and then hinting ever so slightly that he'd give her a call when he got home.

So he did just that: he wrote his letter, he shared what was going on with him, inquired about her summertime activities, and told her that he'd call her when he got back. He folded the paper, stuffed it into the envelope, stamped it, and dropped it in the mailbox.

And when he got home…he never made the phone call. He just couldn't do it. He was too scared. What if he'd overdone it? What if he'd come on too strong?

When school started in September, Jill was colder than a penguin's scrotum. She acted as if they inhabited separate quantum realities.

Allen concluded that the reason why was because he had, indeed, come on too strong in the letter, and cursed himself for sending it. He had no real recourse; he couldn't very well write ANOTHER letter, and he hadn't been able to call her on the phone when she had been platonically friendly to him. He didn't know what to do, so…he did nothing.

That year passed, and then senior year. Allen busied himself with other things, but he never lost his passion for Jill. Graduation came and went, and as always happens, friends and acquaintances went their separate ways. Allen was accepted at a major in-state university, while Jill moved halfway across the country to a small college in Missouri. And still he loved her, such that it never occurred to him to play the field where he was. Besides, he was still as painfully shy as he'd always been.

New Year's Eve of Allen's junior year he was home and got together with some friends to watch Dick Clark's ball descend (that's how Allen described it, anyway), when who should show up but Jill Miller. This is my chance, he thought; enough with this adolescent nonsense; I'm a man now, and she's a woman - I can talk to her. I CAN talk to her. Heck, he thought self-deprecatingly, maybe I can even talk her into joining in a game of strip-Trivial Pursuit.

So, just as he had seven years before, with his heart hammering in his throat, he stammeringly struck up some small talk with Jill. And also like seven years before, she was just as nice, and just as easily embarrassed. But this time Allen managed not to talk about "hookers" and "sucking," although the latter was still definitely on his mind, if still buried deep within it.

Jill told him, to his pleasant surprise, that she had transferred to an in-state school, which was on the other side of the state but still a lot closer than she had been. With this new relational beachhead now established, Allen began corresponding with her regularly, and she with him. And when the summer arrived, he felt emboldened enough to ask her out on a date, and was rewarded with an enthusiastic acceptance.

The two became inseparable, spending almost every day together. It didn't really matter what they did or where they were; their togetherness was all that seemed to matter. Allen had never been happier.

But he still had a problem: his pathological fear of talking to Jill had simply gone on a forced march ahead of him and had now transformed into a pathological fear of intimacy. He could talk with Jill about seemingly every subject under the sun except the personal. And forget about trying to kiss her. Even the thought of holding her hand made him break out in cold sweats, even as it also gave him a constant, running boner of granite proportions.

The dog days debuted, signaling summer's waning. Soon it would be time to return to their respective schools, he thought morosely, and he'd be reduced back to reading her letters and shooting putty at the ceiling.

With such happy thoughts dancing through his head like malignant sugar plumbs, or Dick Clark's undescended balls, Allen called Jill's house to see if she wanted to go see a movie.

"No, Allen, I'm sorry, but Jill isn't here tonight," her mother replied.

Oh, this didn't sound good. "Where is she, Mrs. Miller?"

"Jill is house-sitting for some friends of ours - the Tapletts, I think."

"Oh, yes, my family knows them too. Would you please tell Jill that I called? Maybe we can get together tomorrow."

"Certainly Allen. Thanks for calling. Goodbye."

Allen hung up the phone, an idea blooming in tandem with the grin on his face. Jill and he; in somebody else's house; alone; just the two of them. It was almost too good to be true.

Shaking his head, he realized it WAS too good to be true. But he could still go over and they could watch Seinfeld or the Simpsons together, right?

Walking up to the door, Allen was still telling himself, almost desperately, that nothing was going to happen, because the thrill running from his genitals up his spine and back down again wouldn't go away. Neither would his hardon, which was raging like a six-alarm structure fire. He'd had to change from boxers to briefs just to keep his shorts from tenting out like a storefront awning.

He rang the doorbell and waited. And waited. And waited. He peered in the side window, wondering what was taking so long. Jill's car was in the driveway, so where could she be? Then a thought erupted in his mind that maybe she was out with somebody else. Yeah, that must be it - all this time spent together this summer and I've been as shallow as a kid's wading pool. Damn it, I blew it again with her! When am I ever going to learn? Why don't I have any balls? I'm getting in my car right now and wrap it around the nearest--

The door opened, and there stood Jill. In a bathrobe. Hair wet.

Ohhhhhh, man.

"Um, hi, Jill." Allen managed.

"Hi, Allen. What brings you here tonight?"

What's underneath that bathrobe, Allen thought. Aloud he said, "Well, I called your house and your mom said you were house-sitting down here so I thought I'd surprise you. But I can see you're busy, I’m sorry I didn't call first, I'll be--"

"That's okay, come on in. I just washed my hair, so you can have a soda while I finish drying it."

And taking Allen's hand, she led him down the main hallway to the living room, where an ice cold soda already awaited him on the coffee table, as though straight from a Star Trek replicator. For which Allen was particularly thankful, as his mouth had gone very dry all of a sudden.

"Thanks. I'll just turn on the TV. What do you want to watch? It's all reruns, but there's a good Simpsons on--"

"I have a video that you might enjoy. Just sit tight here while I make myself presentable."

Why does she keep interrupting me? That's not like Jill at all. "Um, okay. Which movie is it?"

"You'll see." Jill replied cryptically.

She disappeared down the side hallway before he could come up with a suave riposte, leaving him with his stubborn spine-genitalia connection, wood of old-growth magnitude, and a belly full of butterflies.

Unable to sit still without fidgeting, he got up and browsed through the videos in the Tapletts' entertainment center cabinet. Not much of a selection there - mostly chick flicks and Hallmark drivel.

"I've got the tape right here," called Jill's voice.

Allen turned around and his jaw hit the floor with a Wile E. Coyote thud.

There before him stood Jill Miller, the girl of his dreams, both dry and wet, in Victoria's Secret lingerie. The small but firm bust of girlhood was now a C-cup rack of nothing short of perfection, and damn near just about everything but the nipples were in full, glorious view. The panties barely even qualified for the name - thong would be more accurate, covering so little of her hidden treasure that she had to be almost totally shaved. And her ass was completely on display, and was beyond belief. The overall effect was reminiscent of the legend of Helen of Troy launching a thousand ships, or at least causing a thousand sailors to lose their loads all at once. And in her hands she held an adult video entitled, "While You Were Sleeping, We Were Fucking."

As for Allen, it scared the hell out of him, and all he could think of was that she was calling his bluff and he had to get out of there. But his legs, damn them, picked this moment to turn on him, no doubt in conspiracy with his groin, which not even his briefs could conceal anymore.

"Come here, big boy," purred Jill.

"Um, uh, er, what do, um, what can I, that is--"

"Just come here."

"But Jill, we hardly know each other, I mean, well, we KNOW each other, but not THIS well, and what if the Tapletts come back early and find you, I mean, find us, well--"

"Allen…"

"And what if your mom calls? Your folks trust me and I don't want to betray that, I mean, what if they found out that I came over here and we, uh--"

"Allen!"

"Hum?"

"Why did you come over here?"

"Well, ah, like I said, I thought we could watch some TV and--"

"And that's all we're going to do."

"Really?" Allen squeaked almost in relief. "With you wearing…that?"

"It's comfortable," Jill shrugged. "I put it on for modesty's sake, actually. Usually I wear nothing at all."

"Who are you, and what have you done with my friend Jill?" Allen joked skittishly.

"Come over here to the couch and find out," she replied sweetly.

Allen complied. "Can I have another soda?" he asked.

"Be quiet" Jill commanded.

Allen complied again.

She inserted the tape into the Tapletts' VCR and the show was on.

It wasn't the first porn Allen had seen, though he would never in his wildest dreams have ever admitted that to Jill. But then he never in his wildest dreams would ever have imagined that he'd be watching one with Jill, much less in this set of circumstances.

As the erotic images tumbled and writhed and gyrated across the screen, complete with slurping and groaning and flesh slapping and a torrent of filthy dialogue that he always found irritatingly distracting, something unexpected took place - his abundance of detoured blood flow began redirecting itself to its original pathways. Truth be told, he was growing bored. And as he beheld the unfathomed vixen sitting beside him, her attention raptly held by the onscreen goings-on, he began to feel like a fifth wheel. And that began to piss him off.

"Jill?"

"Shh, this is the best part."

On the screen the man was about to penetrate the woman anally, something that also held little appeal for him. "Why are you so focused in on this movie? I mean, uh, I thought with you in, um, your present state of undress, that--"

"Allen, pay attention!"

Now he was really becoming annoyed. "To what? Jack Hammer cramming his bone up Cindy Morehead's poop chute? So what? Is there going to be an exam on it later? Do I get partial credit if I guess his pecker size within two inches? What IS it with you, anyway? Where did this slut persona come from?"

Jill's eyes narrowed as she paused the VCR. Part of Allen chilled at the realization that he may have stuck his foot in his mouth again, but damn it, as exhilarating as all of this had seemed at first, it was becoming damned peculiar, and he wanted some answers. Such as who this slut was and what she had done with his friend, Jill.

"I'll ask you again, Allen: why did you come over here?"

"I told you-"

"Bullshit. You didn't come over here to watch TV re-runs. You came over here to fuck me."

The setting was whirling away into surreality. HIS Jill, using language like that? His Jill, a closet nudist? His Jill, a porn connoisseur? What had happened to her?

"Jill, I wasn't-"

"Do the math, hon. You call my house, you find out I’m down here, alone. You don't call in advance but come over here unannounced. You and I, with an opulent house, complete with Jacuzzi, all to ourselves. What else could that possibly suggest to you? How can I spell it out any plainer? Why do you think I went to all this trouble?"

Allen had lost her after "Jacuzzi." "What?"

"This," Jill replied, dropping to her knees in front of the couch and pulling down Allen's shorts and briefs in one smooth motion. Taking his reawakening cock in her hand, she promptly swallowed it down to the hilt, with a tongue bath of his balls for good measure, with an expertise that was at once mind-blowing and disconcerting for where and how she must have obtained it.

Once again Allen was at a loss for words, but this time he didn't care. The things Jill was doing to his dick with her mouth were indescribable. It was so hot and moist that he dimly thought that this must be what a Ball Park frank feels like when it cooks. She varied speeds and motions, at times licking from the edge of his asshole all the way up to his cockhead with agonizing slowness, at others bobbing her head up and down in a blur, and all of it seemingly designed to draw out the experience to marathon lengths.

On the other hand, her expertise was pitted against his virginity, and the latter opened up a can of whup-ass on the former. Allen dimly realized that his ejaculation was approaching like a runaway freight train, and he gamely tried to warn her. "Jill, I'm gonna cum…"

Her reaction to this news was to increase the suction of her lips and somehow slather her tongue over all sides of his cockhead at the same time. This brought about an orgasmic eruption that he feared might drown her, but instead she deftly deep-throated Mr. Happy and used her throat muscles to milk every last drop of the torrent of semen that was jetting into her mouth.

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