This is the start of a (currently) 3 part story, dealing with the world’s biggest sissy, the world’s biggest she stud, the greatest hookup ever written and (eventually) all that follows! If you want to read the rest of the night and stay informed of all the nights beyond, subscribe to my patreon:

https://www.patreon.com/c/SissyGirlSammi

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Cayli had promised to be on her best behavior, but even that was far outside the bounds of polite society. She had a reputation that crossed state lines, that was known to multiple members of the same families, and that made her own family a bit uneasy when it came to events such as this. Her sister was getting married, after all. Her mother was worried that she might wear a white dress as well, never content with someone else as the center of attention. But Cayli’s sister knew that was the least of their possible problems.
Cayli was a femboy.
Whether you called her that, or a sissy, or whatever term seemed most apt for the body that expertly combined girlish and boyish beauty into something you’d want to bend over, you were struck by a single word when you first saw her:
Trouble.
Cayli had always been trouble, and she was darn proud of it. It was usually the bottom who couldn’t walk in the morning, but she was glad to be so good that she sent her tops stumbling. The strongest athletes ended up totally drained after a night with her. The biggest studs were panting for air when she had her way. Sure, she was the image of feminine fragility, a dainty flower that seemed like she might shatter if a strong wind hit her. But she was also the queen of the broken bed, who made men feel like they were going to have an aneurysm without breaking too much of a sweat.
Today she was wearing a green dress that showed off her bottom heavy shape, despite all efforts of the designer. It was usually the case that the bridesmaid dress would diminish the attractive features of the girls so that the bride could shine, but there was just nothing that could be done about Cayli’s rear. It would make a scene even in a wood-hooped dress. Her tiny waist, wide hips and absolute dumptruck would just have to exist in the green number, despite some people’s objections. Talia was fine with it, after all. She loved her sister despite all her wildness, and the wedding put her in mind of a brighter future. Love, settling down…
If she could do it, maybe Cayli could too?

“As if!” scoffed Cayli as her sister got ready. She was checking her makeup in the mirror, styling her lovely brown pixie cut a bit more and looking at herself from all angles. She had only an A cup chest, so there wasn’t much lost with this concealing dress, but seeing that her hefty bottom overcame its attempts at modesty was quite the victory. She was incorrigible. She always had been. She remembered back to when the entire college football team had run a train on her. She was a bit exhausted by the time the special teams had their turn, but she still hadn’t relented.
Incorrigible.
Insatiable.
Incredible.
“I’m just saying, maybe you’ll meet the one someday!”
“There is no one for me. There might be a group, but even then I’d be too much.”
“Oh come on…” pouted Talia, walking over and looking at her adorable little sis. She’d always supported her in her femminess, even when she realized that her brother was now far prettier than her! But if there was one thing she always hoped for, it was that there’d be more than just hookups. Sure, she didn’t judge…much. Anyone would get a bit wide eyed and shocked when they found out their sister could fit two forearms in her. But even if she was okay with it, she would have liked her femboy bro to find love. “It’s a wedding! Love is in the air! Maybe you’ll meet someone!”
Calyi rolled her eyes. “We’ve been at this hotel two days. I’ve already met several someones. I met someone already today. Why do you think I was late?” she winked.
Talia sighed. “You know, it’s a good thing you’re not a cis woman because you’d be ‘late’ all the time if you were.”
“Is that a sense of humor from Talia? And a dirty joke too! Wow, marriage really does change someone” nudged Cayli.
“Fine, fine! Have your fun. I’m just so happy to be with Freddy and I want that for you.”
Cayli wasn’t entirely paying attention, thinking of all the several someones she had hooked up with this weekend and trying to order them from best to worst. None were incredible, but it was a wedding. She was bound to hook up with someone interesting…or at least as interesting as one person could be in the sea of partners Cayli had been with.
“And I’m happy you’re happy but we’re two super different people” reminded Cayli. “I mean, I don’t think there’s a person alive that could keep up with me.”

Kelly kept a full bottle of Plan B on her at all times.
Even if she pulled out, used a condom or acted as safe as humanly possible, Futas were the most potent beings in existence. That, matched with their overdriven desires, meant that you had to be as careful as possible to avoid accidents. She had it all down to a science by now, and had certainly put her 10,000 hours in. Heck, she’d probably gotten to that number before she was a sophomore in college, running through sororities until every girl on campus blushed when they saw her.
She wasn’t just a Futa, although that would be enough. She was THE Futa, at least according to herself. She had turned bragging brats into drooling, incoherent messes, had broken wannabe dommes and confident minxes alike. There was simply no one that could stand up to her mighty shaft, and the muscled yet feminine body that wielded it. She stood 6ft1, not counting her short and spiked up red hair, and every inch of her was taut and boiling with need. It wasn’t that she minded weddings, it was just that they were a reminder of how weak most women were. That wasn’t quite fair to them, as asking them to survive Kelly’s onslaught more than once was like asking someone to take a jackhammer inside them every night, but it was still annoying. Kelly could never find love, although maybe she didn’t want it. Futa were meant to hook up with new girls every night, and few if any let themselves get tied down. Kelly would probably go crazy if she had to actually be in a relationship.
She looked down at her masc suit, whose sleek black coloring could do nothing to hide the massive bulge in the pants. No matter how big her biceps were, how shredded her abs got or how much she worked on her hair, that was always the eye catcher, and she could hardly be mad about it.
It was her cousin getting married, so she had at least tried to be discreet about her hookups. It wasn’t as if Freddy didn’t know, but you could make a man feel a bit emasculated when you did what Kelly did and when what he did was ‘normal’. Talia seemed nice and all, and she was happy for him, but the idea of being tied down?
As if.
She had just hooked up with a girl in the shower and was already feeling like she needed some more, as if the hot blonde from the bar had just been an appetizer for the main course. Weddings were rife with hookups and she was expecting one tonight. Maybe two or three, if she really wanted to be satisfied.
As she took one last look in the mirror, she wondered how Freddy did it. Well, she actually understood how he did it. He was normal, and was happy with a normal wife in a normal marriage. But Kelly was exceptional. She ought to be studied in a lab that researched how to be a stud. One woman would never be enough.
At least, none she’d ever met.

The wedding had been beautiful, and even Cayli had to admit that. Seeing her sister getting married made her feel a certain type of way, and she cried as she stood next to her. She even managed to avoid any craziness, pulling off the role of Maid of Honor without getting into her typical lewd hijinks. No, lewd hijinks were earmarked for after the wedding.
As she minced into the reception, wearing 6 inch heels yet barely reaching 5ft6 in them, she kept a lookout for prey. Some people saw femboys as prey but that’s only because they had a simplistic view of things. A venus flytrap is a predator, even if it just sits there in wait. It attracts victims, and then it takes them inside it until it’s over.
Femboys are much the same. And Cayli was one of the best.
She stalked across the floor, each click of her heels on the hardwood forming a rhythm like the approach of a stalking lioness. Her butt bounced with each one, its movement visible even beneath the loose and heavy green fabric of her bridesmaid dress. She understood Talia making her wear this for the wedding, but it was a bit unfair she was stuck in it for the reception. After all, this was her time to play.
She leaned over the bar in a pose that could only be described as “I dare you to look at something besides my ass,” rapping her pink nails against it until the bartender came over.
“Just a water.”
She wanted to be hydrated for whatever came next.
It was slim pickings from the looks of it, though she hadn’t met many of Freddy’s family and friends. As the Maid of Honor, her focus had been on the stage and not the guest, and she doubted anyone would be worthy of her. Maybe if the whole groomsman party railed her in a train, it’d be a nice capstone to a weekend, but she got the idea they were squares. Sure, they looked. Everyone was looking, even if they were pretending not to. An older man got caught by his wife, who shot him a withering look before she took her own glance. Cayli’s bottom ought to have been in a museum, insured for millions of dollars and reproduced by the world’s greatest artists. Beyond anything as high minded as that, it was just impeccable. It was more than the elephant in the room.
If they had been a literal elephant in the room, they would have all ignored it in order to oogle that butt.
However, Cayli softened her pose as the first dance began, and as Talia and Freddy swayed across the floor. The happy couple moved to cut the cake and took their places as everyone began to mingle.

Kelly stood in the bathroom, scrolling through Tinder. Every single time she swiped right, it was a match. She would have liked to meet someone at the wedding though, even if she had opted to sit in the back. She could hardly see the stage from her seat, and more or less daydreamed as the ceremony went on. She was of a few different minds about it, but there was one part of her that was sure what it needed.
She’d been right when she thought that the blonde would only be an appetizer. She needed more.
The last time she was at a hotel like this, she’d hooked up with a girl on the beach, and another on a boat, and another in the ocean, and then another in the hotel room. But the craziness of the wedding had limited her ability to get out there, and as she walked into the reception, she wondered if anyone was worth her time. It wouldn’t be great to start off the joining of two families by her making one walk with a pronounced limp, but there weren’t any other options.
She shook her head, telling herself that a she-stud shouldn’t worry. The world had a way of throwing willing women in front of her, or making women willing by her mere presence. So she went to the bar, ordering a scotch and thinking back to this afternoon.
The blonde had been hot. She’d had a great body. The noises she made were incredible to hear.
But it just wasn’t enough. Maybe Kelly had to start focusing on three ways from now on?
Either way, she sat there and drank, waiting for someone to fall into her lap.
And then, when she was in her lap, she’d see just how much there was to sit on…

“Are you sure this is a good idea?” whispered Talia.
“Good idea? No. Interesting…” mused Freddy.
“I’m serious. It sounds like it makes sense but I’ve never heard of someone trying it before.”
“Well then, let’s do it. If we’re wrong, then they’re both bulletproof. If we’re not and they’re vulnerable with each other…how could that be a bad thing?”
They looked out at their respective relatives from across the room, wondering how they’d come up with an idea this insane.
Or was it insane?
“I’ll get Cayli.”
“I’ll get Kelly.”

The last time that Talia tried setting Cayli up with someone, she had slept with him an hour in and then asked what all the fuss was about. That was her way, and she had come to expect nothing different. But this might be different, so she went over to the bar and sidled up to her sister with a nervous grin. “Hey, there’s someone I want you to meet.”

Freddy had long ago recused himself of any competition with Kelly. She was always going to get the girls, woo the ladies and outshine him in any physical department. It wasn’t as if she needed any help getting girls, or as if Freddy had the ability to give them to her. He’d once suggested that a girl on his college campus would be a great match for her, as they had all the same interests, but she had merely broke her mattress and said goodbye. He never imagined she’d find anyone that kept her attention for more than a night.
Until now.
…hopefully.
“Hey” he said, walking over to Kelly on her side of the bar. “There’s someone I have to introduce you to.”

The sissy and the she-stud were ushered by their respective relatives, confused looks on their face, until they met in the center of the bar.
“Well” said Talia. “I’ll let you two get to know each other.”
“Yeah, have fun!” said Freddy as the bride and groom made their way back to their table.
They hardly got ten feet away before they turned around to see what was happening.

The femboy looked at the Futa.
The Futa looked at the femboy.
They recognized something in each other, almost before they saw anything else.
Trouble.
Then, their eyes narrowed.
Both of them seemed to share the same expression, as if to say: “Fuck you. You’re not trouble. I’m trouble.”
It was going to be a challenge.
It was on.
And, as the happy couple looked at the newly introduced pair, they realized it was too late to stop it.