Condom Capers - Cover

Condom Capers

by Mat Twassel

Copyright© 2021 by Mat Twassel

Fiction Sex Story: Edward has had a thing for Jenny since second grade, but in high school she took up with star athlete Derek Big Dog Dawson. A few years later Edward spots Jenny at the drugstore looking at condoms, and she asks him for advice. Illustrated.

Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa   Consensual   Fiction   .

Edward’s crush on Jenny began in second grade, and in the thirteen years since then it hadn’t abated. Throughout elementary school she was always friendly toward him, sometimes they even joked around, but he was always too shy to declare his full interest. Early on in high school she began dating this upperclassman, Derek Dawson, star athlete, and, to Edward’s way of thinking, a total jerk, not worthy of Jenny.

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One time in the hallway at Jenny’s locker, Edward tried to let her know that she could do better. Unfortunately Derek appeared just in time to hear Edward’s indictment. Derek didn’t bother with words.

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With one punch he flattened Edward. Both were expelled for three days, and as a result, Derek had to miss the quarter final basketball game that week, the team lost, and so went all chance for the state title. Edward had hoped that the episode might at least get him some sympathy from Jenny, but she, like the rest of the school, the rest of the community, shunned him.


Jenny and Derek married the summer after her junior year of college. At the corner drugstore, on his lunch break from his dad’s body shop, Edward had hoped to find the monthly magazine that had published a poem of his—it was due out any day now—but he found instead a copy of the local newspaper, which contained the story of Jenny’s marriage, including a picture of the happy couple.

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Well, whether she looked entirely happy, Edward thought Jenny did look quite stunning if a bit stunned. Derek, to Edward’s eye, still looked like a jerk. Edward was thinking about buying a copy of the paper—just looking at the picture of Jenny gave him more than the beginnings of an erection—when whom should he see at the end of the aisle but the recent bride. She seemed to be undecided about something. Edward thought maybe he could slink away unnoticed, but he took a deep breath, told himself it was time to be a man, and the newspaper firmly in his fist, he stepped down the aisle toward Jenny.

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“Hey,” she said.

“Hey,” he responded. He noticed atop her little shopping basket lay several copies of the paper. “I see you made the Clarion with your wedding.”

“Yeah,” she said. “We just got back from our honeymoon. I managed not to get sunburned too bad. Now Der’s at training camp. The Bears drafted him.”

“I heard,” Edward said. “I used to like the Bears.”

Jenny grinned. “You’re such a...”

Edward wondered what she thought he was, but she didn’t say. Instead, she said, “As long as you’re here, what do you think about these condoms?”

Edward followed her glance to the shelves. Boxes one atop the other. Like cereal. Or skyscrapers. Or ... Square silos. In that instant Edward wondered if he could include them in a poem.”

“So many to choose from,” said Jenny, after a moment. “Do you have a preference?”

Edward, who had never in his life purchased a condom, said, “Um...” He thought maybe “Rubber City” would make a good title. Or did that call to mind automobile tires? The back corner of his dad’s body shop had used tires piled to the ceiling.

“Maybe we should try them all,” Jenny said.

“We should? I mean, we should!”

“Not you and me, silly,” Jenny said. She shook her head, half smile, half scowl. “You’re such a funny guy.”

Edward was thinking about how he could ask her why she wanted condoms, but then, why does anyone want condoms, when she said, “I think I’ll just get these,” and she took a box down from the shelf, said, “Nice running into you again,” and at a fast pace set off toward the cashier.

Edward watched her go, and after she’d left the store, in addition to that week’s Clarion, he bought a box of the condoms Jenny had chosen.


Right after dinner that evening, having made sure his bedroom door was locked, he tried out one of the condoms. It wasn’t that easy getting it on. Once the thing was fully fitted, he spread the newspaper on his childhood desk, opened it to Jenny’s wedding picture, and, trying hard to ignore Derek, that feckless, foolish jock, he masturbated.

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A few minutes of stroking later, he convulsed, and the condom was filled. The bloated tip dangled. It wasn’t that easy peeling it off. That task accomplished, he squeezed what cum he could onto Derek’s smiling face. “Rain of Cum,” he thought—possibly a better title for the poem. Or should it be “Reign of Cum”? He felt bad—not because he’d defaced Derek but because were Jenny aware of this deed, she’d think even less of him than she already did. At least I didn’t get any on her, he thought. But then he couldn’t help thinking that Derek likely got his stuff on her all the time. Or maybe just in her. Or maybe not even that, if he was wearing a condom. He crumpled the newspaper haphazardly and flung it toward the wastebasket. The shot, if it could be called that, hit the rim and fell to the floor. “Impotently,” the poet in him decided. “Fruitlessly.” He retrieved the paper, straightened it out, bundled the used condom inside, crumpled the paper again, and made another toss. Dead center.

Fifteen minutes later, whatever satisfaction remained from his ejaculation had disappeared. Remorse set in. Edward fished the crumpled newspaper from the wastebasket. Cautiously he spread it open. The wedding photo was soaked with semen. Ruined. Even so, Edward found himself freshly aroused. He couldn’t quite decide whether to masturbate again, to shower Jenny’s picture with his stuff, or to hurry back to the drugstore to get a fresh copy before they closed. And maybe that magazine would be in. Maybe he could buy two copies of the paper. Or three. Or all they had. Such were his thoughts when his mom tapped on the door. “Eddie Bear, you have a phone call.”

Edward looked at his phone. It sat still and innocent on his bed.

“I didn’t hear it ring,” he said, only after his words were out realizing the foolishness.

“It’s some girl,” said his mother through the door.

“Be right down,” Edward said. “I was just going to, um, take a shower.”

He wrapped himself in a bath towel and hurried downstairs, wondering who it could be.

“I’m sorry for disturbing your mom, but I didn’t know your cell,” Jenny told him. Somehow he’d recognized her voice though they’d never before spoken on the phone. Until this afternoon he hadn’t spoken to her at all in more than four years. “I’m sorry for hurrying off from you this afternoon. I didn’t mean to be rude. My thoughts are kind of in a jumble.”

“It’s okay,” Edward said. “Mine too,” he mumbled. “Mine too,” he repeated, with what he hoped expressed some vigor.

“But I didn’t know who else to call,” Jenny continued. “I have the hugest favor to ask. You know, about the condoms. Is there any chance you could help me out?”

“Help you out?” Edward asked, his voice feeble again.

“Yeah, it would be so fantastic if you could. If you could come over?”

“Tonight? Right now?”

“Yeah, or maybe in an hour. We have a place at the new apartments on 4th Street. Brand new. Number 606. Okay?”

“Okay,” Edward said.

“That’s such a relief. You’re a life-saver.”

Before Edward could figure out how to ask exactly what the favor was, Jenny had hung up.

An hour ... Edward took a quick shower. While toweling off in his bedroom he wondered if his mom had noticed the open box of condoms on the bed. Or the semen smeared photograph of Jenny and Derek on the desk. Once again he crumpled the paper and dropped it in the wastebasket. He was about to discard the box with its eleven unopened condom packets when he had a wild idea. He could sabotage these condoms, poke a hole in them using a needle or something, and then—wouldn’t that serve Derek and Jenny right? But then he thought, no, the world doesn’t need any more Dereks, and he wouldn’t want to saddle Jenny with two of them, or three, if she had twins. Obviously she didn’t want kids if she was using condoms. Not Derek’s kids, anyway. And that’s when an even more brilliant idea came to him. He’d sabotage one of the condoms, and then when he and Jenny made love, it would be his kid, and Derek would be so upset he’d leave Jenny, and Jenny would be so ... so what? And what made him think he and Jenny would make love? And how would he switch her condoms with his sabotaged one? And would a pinhole even work? Not such a brilliant idea after all.

Still ... maybe a test was in order. From the shelf of his closet, Edward pulled down the dress shirt, a Christmas gift from his mom, still in its plastic sheath. He withdrew the shirt from the casing, and sure enough, pins.

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He used one of them to poke a hole through one of the condom packets. The hole wasn’t too noticeable, especially if you didn’t look for it. But would such a tiny hole be sufficient? He knew sperms were microscopic. Or maybe the condom would break inside Jenny. Edward’s erection bowed his underpants. “Fuck,” he said, not quite aloud. There wasn’t time for a test. And the entire scheme was ludicrous. What made him think he had any chance of ... He put on some jeans and the new shirt, then, ever hopeful, he stabbed a pin through a fresh condom packet, put it into jeans’ pocket, and set off for Jenny’s 4th Street apartment.


“I’m so glad to see you,” Jenny said, ushering him into the apartment.

“Um, nice place,” Edward said, looking at the bare walls. The bare everything. Almost everything. Some gift-wrapped boxes were stacked in one corner. Some wrapping paper was crumpled and on the floor. And Jenny was wearing what looked like a nightgown, nearly transparent.

“At least it’s not a mess,” she said. “The furniture is supposed to arrive later this week. Right now we just have the bed. Actually just the mattress. And some wedding presents we haven’t opened yet.”

 
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