Tawns of Fun

Imagine Tom asking why he shouldn’t fire you like he did Nancy and Jonathan. 

Because I’m willing to do whatever you want to help you relieve stress. Because I don’t always wear anything under my work clothes. Because I want to be your lover.

“How about,” you found yourself asking, “we go into your office and I’ll show you why you should keep me?”

Imagine thinking you’re a dead woman when Esme finds out about your affair with Carlisle. 

Imagine Ransom blackmailing you into dating him after finding out you used to have a casual affair with his father.

Imagine not having a Tethered counterpart, so Tex has more incentive to pursue you. Your family’s on vacation with the Wilsons and Tylers. With everyone around, you’re frustrated you can’t properly consummate your affair with Josh. But he’ll be replaced soon, with Kitty to follow, and Dahlia doesn’t care what her “husband” does.

Imagine thinking you hooked up with Josh outside his vacation house. 

It was risky, with the possibility of being discovered by Kitty, but that’s just what made it all the more hot. The only thing that slightly unnerved you about the encounter was that Josh seemed to be roleplaying. But you had no idea what. 

Red jumpsuit, slicked back hair, and was he wearing makeup? Or not wearing makeup? He’d either shaved his brows and painted himself to look sleepless or... You’d been invited in to have drinks with the Tylers earlier, so you shrugged it off. Maybe the darkness had distorted his features. 

“How did you manage to change your outfit so quickly?” you asked softly, in case his wife was near. Josh already had a drink in hand and looked comfortable lounging. 

“My outfit? Like what I was wearing on the beach?”

Imagine Tom stealing Heather’s keys so you and him can go skinny dipping in the Hawkins Community Pool afterhours.

Imagine your boyfriend Ransom being amused when he finds out you had affairs with Richard and Harlan before you started dating him. Without either his father or grandfather knowing about the other man.

Imagine a weight lifting itself off your shoulders when you learn about Michelle’s affair. It makes you feel better about what you did with your coworker Marcus. Sure, it involved inappropriate usage of hospital equipment, like a thermometer. But it was just a one night stand. Purge Night is not the time to bring it up.

Imagine Tom noticing you could use some cheering up when you come into work.

You start to thank Nancy for placing tea on your desk, when she cuts you off to tell you it was Tom. Trying not to grin too broadly, you thank her for telling you. It tastes a bit different than whatever brand Hawkins Post usually uses.

The next time you’re given tea, your boss actually hands it to you. His fingers brush against your own and he smiles as you take your first sip.

Before you leave for the day, you find yourself with yet another cup in hand. It’s just you and Tom at the office. Janet thinks he’s working late again, your lover explains.

“So we finally get to have some fun?”

Tom chuckles and explains that he’s been having fun all day: discreetly cum/ming in your beverages. Now he wants to make you c/u/m three times, but he’ll take it straight from the source.

Imagine step-nepotism landing you a job at the Hawkins Post. Heather got a sweet gig at the pool, you got a sweeter gig under her father. 

Literally, you muse while he rubs his c0ck along your folds. Tom arches his back before finally slipping inside. The great thing about older men is they last longer. Hence all the fore/play. Your stepdad was going to make a considerate lover.

Too bad you didn’t examine the dark veins on his member more closely. The dark veins that were now visibly pulsing on other parts of his body.

The Mind Flayer was luxuriating in his new vessel. There was no need for Tom to mate with his wife anymore. Janet was just another host. Your unknown lover wasn’t going to infest you. At least, the Mind Flayer would keep you unpossessed, but you’d look good stuffed with tentacles.

Imagine Jonathan taking pictures of Tom’s dalliances with you. Your coworker’ll squirrel them away, in case he needs to blackmail Tom for a raise. In the mean time, the photos will make some excellent masturbatory material.

Imagine asking Billy if you can borrow his Camaro. He asks why. You tell him you’re planning on having sex with his coworker’s father.

“No, really, why do you want to borrow it?”

“I want to have sex with Mr. Holloway in it before you have sex with Mrs. Wheeler.”

Billy leers before tossing you the keys.

You decide to leave your pant/ies as a thank-you. Tom wasn’t, to your relief, too bothered by that. He even joked that it was a good thing you made him wear condoms, otherwise Billy would be finding spunk-soaked pairs in his backseat.

“‘Backseat’? I was going to try to be more discreet and stash them in the glovebox. Also, ‘pairs’?”

“Well,” replied Tom, setting his hands on your hips and pulling you closer, “I think we should not only show him how grateful we are, but-”

“But how much we trust him?”

“Sure.” Tom’s smile widened. “He hasn’t started in on Nancy’s mother yet, has he?”

“I don’t think so.” 

A couple days later, you caught Billy’s eye in the rear-view mirror. Then Tom hit a bundle of nerves, causing you to a contented sigh as you squirmed on his lap.

“Billy, do you want these?” asked your boss, holding up your freshly discarded pant/ies. Your friend let you moan from the finger caressing your c/l/i/t before responding.

“Yes, but let me finish this pair.”

Leaning forward, you saw that he was using your under/wear to jerk o/f/f.

Note: I want to clarify the car was not in motion during this session.

Imagine starting an affair with Tom Holloway but having difficulty initiating sessions at first. Your homes are off-limits. Even quickies in his car might accidentally leave physical evidence for Janet to find.

One day he drives you to the next town over, rubbing you through your pan/ties whenever you come to a stop. Shifting in your seat, you wonder if Tom has a friend who’s place you can use. Until you realize he wants to take you in a back alley. Tom has you bend forward, place your hands against the wall, and spread your legs.

Later, feeling spunky, you ask Billy if you can borrow his Camaro. He asks why. You tell him you’re planning on having sex with his coworker’s father.

“No, really, why do you want to borrow it?”

“I want to have sex with Mr. Holloway in it before you have sex with Mrs. Wheeler.”

Billy leers before tossing you the keys.

Imagine, despite you both being married to different people, convincing your boss Tom Holloway to give you a baby. He’s so grateful. Janet enjoyed being pregnant because her husband could barely keep his hands to himself. But she only wanted one child. Once he’s deposited a heavy load of c/u/m inside you, Tom wastes no time in pulling you off his d/i/c/k and onto his face. He’s planning on orgasmically rewarding you for fulfilling several of his fantasies at once.

Imagine getting your boss Tom so flustered in his office that he bends you over his desk and takes you without bothering to wrap it. A first.

“Oh cool, are we giving Heather a little half-sibling?”

Imagine Mr. Lerner not bothering to hide his erection/s after the first time you sleep together. It might be a little early to tell you he wants to give Luke a half-sibling, though.

Imagine Tom convincing you to quit your lifeguard job to work for him. Heather just thinks he did you a favor. What your friend doesn’t know is that her father wants you where you can be easily coaxed into an actual affair. 

You two already kissed. His wife and daughter never visit the office. You’re always trying to discreetly check him out. It’ll work.

Too bad he won’t get to see you in a swimsuit as much. Well, Tom amends, you could wear one under your clothes. After you feel what the editor-in-chief can do with his tongue, you’ll wear whatever he wants.