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Shane’s Sexting Misadventures

Summary:

Ilya
Do you think I can make you cry while you cum?

Shane
If you’re rough enough. 

After being teased one too many times about his subpar sexting prowess, Shane seeks out help to elevate his skills and makes Ilya fall a little in love with him during the process.

Notes:

please keep creator’s style enabled.

rated M because honestly, i don’t think it gets that explicit tbh, but if anyone thinks i should change the rating, lemme know!!

filth levels are like at middling imo. i would write more but coding was a pain in the ass and i ran out of steam, hehe!

but very fun to write so hope you enjoy the read!!

(See the end of the work for more notes.)

Work Text:

It’s starts with Ilya insinuating, for the umpteenth time, that Shane kind of sucks at sexting.

This, serendipitously, coincides with his visit to Hayden’s home while he’s away to the mandatory bimonthly acquarium visit, supervising the girls as Jackie spends a relatively peaceful day lounging around with the baby. 

“Did you bring another box of chocolate to woo my children?” Jackie asks him when he sets down a big package onto their kitchen counter. 

Shane gives her a half-smile, settling into the armchair that is more or less reserved as his spot in their house, and shrugs affably, “I need to do something to maintain my top spot in their hierarchy of Uncles.”

“You can just show your face every once in a while and that’ll be enough,” Jackie says. She’s nursing a hot cup of coffee that is starting to get tepid. “Missing Hayden? He won’t be back till nightfall.”

“No, no,” Shane chuckles, regarding Jackie with a meaningful look she can’t decipher. “I am glad he isn’t here, actually. I need some advice. From you.”

Jackie’s brow makes a perfect arch and she sits up, her antenna for gossip standing taut, “Oh? What’s this about?”

Shane clears his throat awkwardly, looking around, “Arthur?” 

Jackie waves a hand, “He’s sleeping Shane. Don’t worry.”

“Okay,” Shane says haltingly and braces himself. Generally, he would rather pull teeth than reveal anything about Ilya and his relationship to anyone in his life but this is an exception. This is a matter of competition and well, ego. And one thing Shane’s never gonna do is back down from a challenge. Even when it’s ill-advised to pursue it. 

“I was just wondering... ” Shane says, trying to adopt a casual sort of air. “About—um, sexting.”

Jackie stares blankly at him for twelve long seconds before her expression cracks and she huffs a laugh, “Oh my god, Shane. I thought it was going to be something monumental and serious. Sexting? Sexting is easy.”

“It is?” Shane says before he can stop himself, sounding genuinely impressed. “Can you— can you share some tips?”

“Bless you,” Jackie says, still sobering from her bout of laughter. She places a hand on Shane’s arm and squeezes it. She has that look on her face only her kids ever coax out, like she wants to pinch the life out of their cheeks but is holding herself back from doing so. Shane isn’t sure he likes being the receiver of that look. 

“Sure, I’ll share a few tips,” Jackie says graciously, a smile playing on her lips. 

“You can’t tell Hayden,” Shane says. 

“I can’t?” 

“No, please, don’t,” Shane emphasizes. “He’ll tease me to death, Jackie. I can’t handle that.”

“You think I won’t?”

“You’re too decent for that.”

Jackie leans back, sipping from her mug, then she nods her head resolutely, “You’ve convinced me. I’ll be the bearer of your secret. But, well, the issue is Shane that I have only ever sexted men.”

Shane momentarily forgets to react. It’s not an issue—infact, it’s the perfect experience for him to gain wisdom from, but Jackie doesn’t know that and he will be screwed if he lets her gain a clue about this. 

“That’s fine,” Shane says, keeping his voice decidedly neutral. “I can just... translate the context for, um, women.”

Jackie laughs again, not even attempting to get a hold of herself time around, “You’re really determined about this, huh?”

“I’m always determined about everything, I think,” Shane says flatly. “So? Tips?”

Jackie finishes her coffee and gathers her blanket, pooling it on her lap. She has a twinkle in her eye, like Shane has awoken something within her, and she grabs a notebook and pen off the coffee table, and begins to write. Shane watches her with fascination, wondering if this is what consulting with a witch would feel like. 

 

Tip #1: Walk the road less traveled by. Go for the unconventional, niche compliment. 

 

Lily

22 January 2016 8:15 PM
What do you mean?

You really do suck at sexting, wow.
Shut up.
25 January 2016 3:05 PM
Hey

Do you know why I can’t see your face when I’m sucking you off? 
Why?
Because your huge tits get in the way
Is this compliment?
Yes. Your manboobs are very appealing.
What a fucking sentence.
Are you trying to up your game, Hollander?
5/10
Fuck off

“Will you stop smiling at your fucking phone?” Marleau says, throwing his sweaty shirt at Ilya’s head. “It’s starting to get gross.”

Ilya pins him with an unimpressed look and discards his filthy tshirt on the handle of the benchpress.

Sidling upto him, Ilya leans against the treadmill’s stand, watching Marleau ramp up the speed.

“Say, Marleau,” he crosses his arms underneath his clothed chest. “Are my tits really that impressive?”

Marleau groans in exaggerated agony and presses a hand against Ilya’s face, pushing him away. “I don’t give a fuck, Rozanov. Ask your... lady about it.”

Ilya smirks, ducking under him and letting out a humored laugh, “My lady is the one who pointed it out in first place.”

“Goddamn, bro,” Marleau says, starting to get out of breath. “She’s got your ass whipped.”

“Russians don’t do “whipped”, okay?” Ilya says, as he walks back to his spot, unlocking his phone to go over the texts with Shane once more.

Despite himself, he can’t help but crack another small smile.

 

#Tip 2: Everything is a sexual innuendo. The world is your oyester. Sexy lies within the dick of the beholder, so behold that dick. Metaphorically.

 

Lily

08 February 2016 11:16 PM
You’re being boring again.
Do you know what rhymes with boring?

No. Enlighten me, Hollander.
Whoring.
Are you calling me a whore?
You called me a bore!
Neither of us is incorrect.

Lily

17 February 2016 2:45 PM
Do you read?
Read what? Books?
Yes.
Sometimes.
Do you like bookmarking your books?
Yes. Where the fuck are you going with this?
Just saying.
You called me an open book a couple days ago
Holy shit, Hollander.
2/10
I thought it was witty!
My boner just died. Good bye.

Lily

08 March 2016 11:45 PM
Rozanov, I think I am a little drunk.
Congratulations?
Thank you.
Why are you drunk?
Mom’s hosting a party.
Must be nice.
Sure.
Anyway.
I was thinking about hockey.
Shocker.
And you know.
I realised hockey is a very. You know.
Us-friendly sport.
Us-friendly?
Friendly to us. You and me.
Is it? Explain your reasoning.
Well.
Pucks and holes and sticks.
Isn’t that kind of gay?
Oh my god, Hollander.

Lily

10 March 2016 10:12 AM
When I was a preteen, my mom enrolled me in some fancy horseriding lessons.
Thought I should let you know.
Don’t worry. Your experience shows.


Tip #3: Be blunt. Nothing is more arousing than being extremely honest. Hornier the better. 

 

  Lily

28 March 2016 12:25 AM
I’m going to finally answer your questions.

7 inches.
Too small. Boring colour. Nice veins.
Sounds like an Amazon review.
How’s the real thing?
Adequately big. Pretty colour. Nice veins. Excellent thrust.
Finally you’re getting it, Hollander.
9/10.
More like a 7/10 if you ask me. Lots of room for improvement.
Who are you and what have you done to my slow as fuck archrival?
You poked the bear too many times, Rozanov. :))
I’m going to fuck you so hard the next time we meet, Hollander. Throw away that fucking dildo.
Yes, sir. :))

  Lily

17 April 2016 12:25 AM
Do you touch yourself while thinking about me?
Is that a rhetorical question?
Yes, I do. Don’t you?
Doing it right now.
No wonder you’re typing slow today. Typing one-handed right?
Call me.
As you wish.

  Lily

06 June 2016 12:25 AM
Do you think I can make you cry while you cum?
If you’re rough enough.
Is that a challenge?
No. It’s a request.
That’s hot.
It’s time I edged you so hard you beg me with tears in your eyes.
Wow.
Happy pride month to me, I suppose.

“Marleau,” Ilya says, placing a grounding hand on his friend’s shoulder. Sombrely, he confesses, “My lady is a freak. An absolute fucking freak.”

“Match made in heaven, you two,” Marleau replies, shrugging him off with a disgusted but also envious look. “Stop rubbing your thriving sex life into my face. Get lost.”

Ilya bursts into happy, cheeky laughter, content beyond belief that Shane’s started being unreserved in their texts. It’s simultaneously the most bizarre yet the most entertaining thing he’s ever witnessed.

He sighs and pockets his wallet and phone. Time to go buy some rope—for some recreational purposes.

He’ll die before he lets Shane outfreak him, after all.

Notes:

thank you for reading, loves!! xP