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Chapter 35
by princessjasminedoll
What's next?
Double Cucked
"No promises, but I'll think it over," Cloud said, noncommittal.
"You will?" Jessie said, eyes sparkling. "I make a mean pizza, you know? The pussy is renowned too!"
She kissed Cloud, and she felt hot and wet and ready as his tongue pushed into her mouth, dancing with her tongue. Why did he have to wait, he thought? She broke it reluctantly, then turned perkily back to the inside.
Cloud started the walk back to Stargazer Heights, when he saw Biggs and Wedge walking in the opposite direction. Wedge was in a new pair of pants, munching on a giant slice of pizza as he tried to keep up with Biggs. They were headed to Jessie's place.
Cloud quietly turned around, following them at a distance. The two men indeed went into Jessie's house. Cloud snooped around her building, and finally found a hole, from which he could peer into the apartment. These slums were great, he thought, for a voyeur or a spy.
"I'm glad you guys showed up," Jessie said. She lacked her usual bravado. "I want to ... seal the deal with Cloud. But I'm still a virgin. And I'm worried I'm going to disappoint him. So I want my two best guys to fix that problem. And if you tell, I'll kick your ass into next week."
"Jessie ... you're serious?" Wedge asked, mid-bite.
"Wedge ... drop those pants before I change my mind," Jessie said, hitting her forehead with the back of her hand.
Biggs was fit, with a seven inch cock, only slightly longer and no thicker than Cloud's dick. He lined up behind Jessie first, while Wedge kept shoveling food into his mouth, Jessie almost fixated by the tree trunk hanging between his thighs.
"You ready, Jess?" Biggs asked.
"Yeah, of course," Jessie said, shaking her head. "Don't take it easy, either. Fuck me like the merc will tomorrow."
Cloud watched, jaw dropped, fumbling at his trousers and tugging out his cock. He watched Biggs give Jessie her first orgasm from fucking, burying his stiff pecker where Cloud's should be, right then, right now.
"Fuck, Biggs, that's good," Jessie said, slapping the floor. She was sucking the tip of Wedge's prick, but it clearly intimated her. "But ... switch."
"Jessie ... you're sure?" Wedge said, holding a fresh slice. Jessie rolled her eyes.
"Yes, Wedge. Stretch me out," Jessie said. "I want my first time to be memorable."
Cloud's emotions were mixed. Don't do it, he thought to himself. You're going to ruin her cunt, Wedge. Why are you doing this, Jessie? It should be me, us losing it together. Why are you so hard watching, Cloud?
Jessie's ass shined with grease, as the tubby Wedge hadn't stopped consuming. She grunted loudly, and Cloud watched, rapt, tugging his prick as the three came, Biggs all over Jessie's face, Wedge all over her ass, and Jessie's tight body flexing between them both. Cloud grunted, cumming onto the wall.
"Did you hear something?" Jessie asked, suspicious even in the post-coital moment. Cloud froze, hiking up his trousers and slipping away into the darkness. That was one thing operators were good at.
***
Cloud slipped back to the Stargazer, to find Tifa waiting outside.
"You've been gone awhile, Cloud," Tifa said, her voice soft and sweet.
"Was out walking," Cloud responded vaguely.
"I ran into Johnny, by the way. Said not to worry, he was getting out of town," she said, evading what she really wanted to talk about.
"Oh yeah, the himbo," Cloud said knowingly. "Did you ... fuck him again?"
"Yeah. I wish I could explain it, but it wouldn't make sense," Tifa said, with a little weariness. "I wanted to ask you ... you're not thinking of leaving Midgar anytime soon, are you?"
"Well, seems this old friend of mine's in a tight spot… Long time ago I said I'd be there for her. Made a promise, so…" Tifa smiled at the memory, and she sparkled in that moment, Cloud thought. She could be so innocent and so powerfully seductive in the same moment. It was moments like this that made Cloud want only her.
"Can't say this is quite what I had in mind when I put that on you way back when," Tifa said slowly.
"If you wanna talk, I'm listening."
"Huh? What's with you all of a sudden? It's like you've lost that hard edge," Tifa said, looking confused, like she was trying to reconcile multiple versions of Cloud at once.
"Is that .. really a bad thing?"
"Not at all—I like it," Tifa said, shaking her head, smiling that perfect smile again. "Maybe Marlene won't be so scared of you next time… I'm really glad to have you back, Cloud. Really glad. I'd love to catch up more, but we should probably both get some sleep. Good night!"
This was his in, he thought. To be the antithesis of Barret. To be the guy Tifa could talk with. A guy capable of being more than just an eco-terrorist. But he heard Barret came in, and the sweetness of Tifa yielded to the whore within, as she rutted with the Black man, praising the size of his Black cock, calling him her Daddy. Which was the true Tifa? Which was the true him, for that matter? He jerked his cock, listening to Barret pound Tifa raw next door. He'd had a blowjob today, his first ever, and he was still cumming to other people fucking. What the hell was wrong with him?
What's next?
Constantly Cucked Cloud
An FF7 Remake Fanfic
Cloud Strife is a man of multitudes. From a small town, he ascended to the height of SOLDIER. Now a mere mercenary, he tries to forget a confused past and land some pussy...any pussy.
- Tags
- BBC, Cuckold, Interracial, Tifa, FF7, Cloud, Femboy, Gay, Lesbian, Bisexual, Aerith, Cocktease, Feminization, Submission
Updated on Jun 21, 2025
by princessjasminedoll
Created on Mar 17, 2025
by princessjasminedoll
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