Chapter 1: Sin to Win: Explanation, rules, and prices
Summary:
Sin to Win weekends are held every two weeks in different hotels and casinos in Atlantic City. Here is how they work, the rules they follow, and the list of prices they have.
Notes:
Hello!
This is my first fic, and I’m very excited to post it. I want to say the main idea isn’t mine, I was inspired by Sin to Win by ravenhairedgirlies, because I read it and couldn’t stop thinking about it. And even though I am a lesbian Emily Prentiss truther, this was so hot that I have become a bisexual Emily Prentiss stan for a while. I needed more, so I decided to write it myself.
This first chapter, where the whole dynamic is explained, and some of the prices I got from their fic, I made a few tweaks and additions. After that, it was all my horny mind. But I wanted to make clear that the idea belongs to them and to tell everyone to go read the original fic, too, because it is HOT as fuck.
Also, this first chapter is just the explanation and rules of the setting (if that makes sense), but the next chapter is already up, and that’s when the actual smut begins.
I hope you like it!
Chapter Text
Sin to win: The act of trading sexual acts for money and prizes. A secret weekend full of excitement and sex. Basically, men reward women for their erotic acts.
Men can collect special coins at a secret spot before the weekend begins. The coins are golden and have an S on the front and a W on the back. The women simply have to whisper the words Sin to win in a man’s ear if they think he is interesting. When the guy likes the woman back, he hands her a coin. They now made a deal to spend time together; how long depends entirely on the woman.
The woman can always discuss different prices or rewards, like expensive gifts, with the man if she wants to, but there is a standard list of prices that goes as follows for those who don’t want to:
- Striptease - 50$
- Lapdance - 75$
- Makeout session - 80$
- Watch a woman please herself - 350$
- Watch a woman and another woman have sex - 700$
- Watch a woman and a man have sex (rare) - 800$
- Watch a threesome (rare) - 900$ (add 100$ for each person (for example, 1000$ to watch four people have sex, 1100$ for five…)
- Woman pleases man, no penetration - 400$
- Man pleases woman, no penetration - 400$
- Sex - 500$
- Anal sex - an additional 100$ - 600$
- Threesome - 650$
- Sex with four or more people - starts at 850$, add 100$ for each person (example, 850$ for sex with four people, 950$ for sex with five…)
- Roleplay without sex - 200$
- Roleplay with sex - 250$ (+500$ for sex) - 750$
- Fetishes and kinks - *Consult the list of extras for specific ones with different prices.
Any other things not included in any of the lists mentioned should be discussed with the woman.
By letting the man pay for her acts, he feels in control, but because the woman can decide the time frame, the man doesn’t know whether she will do everything he wants her to do.
The important thing with Sin to Win is consent. Even though the man can ask the woman to do anything, she will be the one to decide if she wants to; she can always say no if she feels uncomfortable or doesn’t want to do something.
*List of extras (both receiving and giving): **All of these are additional prices that have to be added to the prices in the previous list. ***All of the extras needed must be included by either the man or the woman.
- Tying up or restraining - 150$
- Impact play - 150$ if it doesn’t leave marks that will last more than 5 days, 300$ if they last more. Forbidden to do anything that leaves permanent marks.
- Exhibitionism - 300$ for places with only a risk of getting caught, 400$ if it is more likely to get caught (See the previous list for people watching sex directly)
- BDSM - 100$ base + all the other additions (example, extra 150$ for restraining, 150$ for impact play…)
- Humiliation - 150$
- Blindfolds - 100$
- Choking - 90$
- Cockwarming - 180$
- Edging and overstimulation - 350$
- Orgasm control - 165$
- Toys (not included) - 75$ for toy + additional 25$ if the woman provides them
- Marking (not permanent) - 65$ if they will last less than 5 days, 90$ if they will last more
- No condom - Only if the woman consents - extra 50$ each time
- Multiple orgasms - 220$
- First times - 470$
- Teaching - 350$
For anything not included on the list, the price should be discussed with the woman.
Chapter 2: Friday, May 28th, 2010 - Oliver
Summary:
The beginning of Emily’s Sin to Win weekend in Atlantic City after her plans were ruined in 05x20.
Notes:
Hi!
Here we are, where the actual smut begins. It is my first time writing straight smut, and definitely the longest smut fic I’ve written, so I hope it’s good.
I hope you enjoy it!
(See the end of the chapter for more notes.)
Chapter Text
“And my non-refundable Sin to Win weekend in Atlantic City.” She was looking forward to it. It has been too long since she had one, and she had finally made the time to go, so a case ruining her weekend, her three days of pure fun, sucked.
“Sin to Win?” Morgan asks. Emily thinks it is cute that he has to.
“Yeah. And I always win big.” The last time was around 10K, and so many orgasms she lost count of them.
“Prentiss, Sin to Win?”
“I’m sorry, what?”
“Come on, I gotta know.” He sure would love to. “What the hell is a Sin to Win weekend in Atlantic City?”
She sighs, looking up and down between him and her cards. “Derek, I have a tremendous amount of respect for you, but there’s some questions that if you have to ask them, it means you probably couldn’t handle the answer.”
And she walks away, leaving him wanting to know more.
She decides to go to the next one once the case is over. Having to wait two whole weeks sucked, but when she finally gets there, she is buzzing with excitement. She leaves her things in her hotel room, changes into a tight black dress, and goes to the hotel bar.
She orders a Manhattan as she looks around at the crowd, most people are here for the same thing as her, and that is what makes it more exciting. She studies the crowd, trying to decide who to approach first. There are a couple of handsome men she wouldn’t mind playing with. And a couple she wouldn’t mind either.
Because this is what this is. A game. A really fun game with a very good prize. A game she always wins big.
But she takes her time. She drinks her cocktail as she considers her options.
“From the handsome man over there,” The bartender says, pointing at a man two chairs to her left.
Emily smirks, taking the glass into her mouth and taking a sip as she looks him in the eye from the distance. Then, she takes the glass in one hand and walks slowly towards him, her heels clinking on the floor with each step.
“Thank you, handsome.” She sets the glass on the counter and plays with her hair as she smiles. This is all part of her game. “That was very generous of you.”
“What can I say?” He smirks. “I’m a man of many qualities. I’m Oliver. You are…?”
“Emily.” She sometimes uses a fake name, but this time she doesn’t want to be another person. Plus, many people here use fake names, so you never know if the name they tell you is real or not. So why should it matter? “Nice to meet you, Oliver. Are you here to play too?”
He plays with his coin, slipping it between his fingers so Emily can see it. “I might be. If you say the magic words.”
Emily smirks, leaning in closer to him. Her hands move to his, and her lips close to his ear, and she whispers. “Sin to Win, baby. Now, will you give me that coin so we can go to your room?”
Without missing a beat, he moves the golden coin from her fingers into Emily’s palm. Emily closes her fingers around it, takes one last sip from her glass, and follows him out of there.
They get to his room in record time. The moment the door closes, he pins her against it.
His hands roam all over her body as he leans in and kisses her. It wasn’t gentle or slow. Not that Emily expected it to be. It’s another thing she likes about the game. She is always in control, and for the weekend, she doesn’t have to be. Well, only sometimes, depending on who she goes with. She opened her mouth, and a little gasp made it out before his tongue found its way inside it. He tastes like whiskey.
Her hands move to his hair to keep him close. His teeth find her lower lip, and he bites and pulls away. Emily can’t stop the moan that escapes her mouth. “Mhmm…”
“You’re wearing too many clothes, doll…” His hands find the zipper of her dress and pull it down before she can say anything else. As the black dress pools on her ankles, he moves his hands over her stomach. “That’s better.”
He steps back, looking up and down her body. “Like what you see?” She teases when his eyes linger on her black lacy underwear. He nods, his eyes glued to her breasts. “Want me to take it off so you can see what’s underneath?”
He shakes his head. “Not yet, doll.” His hands move from her stomach to cup her breasts over the lace. “You look too good like this.”
“Then, what do you want me to do, baby?” She purrs against his lips.
“Lay down…” Oliver whispers against her ear.
Emily nods and walks to the bed. She sits on the edge and lifts her long legs. “Should I take these off?” He nods, so she kicks off her heels and crawls into the bed, lying down on the pillows. “What now?”
He smirks. “Touch yourself,” He whispers, looking her in the eye as he unbuttons his shirt. “I want a show…”
Emily nods, her hand sliding down her stomach and her eyes glued to him. She moves her hand over her panties, rubbing over the wet spot in them. He takes off his shirt and undoes his belt. “Can I take them off?” She asks with a finger sliding under her underwear.
He shakes his head. “Not yet.”
“But I need more…”
“You can take off your bra.” He concedes as he takes off his pants and boxers, his hard dick springs free, making Emily’s mouth water.
“Thank you.” She smiles. Her hands move up to unclasp her bra. When she takes it off, she lets it fall to the floor. Her hands cup her own breasts and squeeze them. “Mhmm.”
Emily pinches her nipples under the attentive eye of Oliver. She smirks as he takes his dick into his hand and strokes it slowly. “That’s it, keep going, doll.”
She keeps playing with her breasts with one hand, and the other moves down her stomach and rubs her clit over her underwear again. “Oliver, baby…?” She pinches her nipple, making herself gasp. “Please let me take these off… You’ll get to see how wet I am.”
He thinks about it for a couple of seconds, his hand slowing down on his dick. “Push them to the side.”
Emily sighs. She will take it. And she likes being told what to do on these weekends. It is the only time she lets herself enjoy it.
Her fingers push her panties to the side, her index finger parting her wet folds. She is so wet she has to resist the urge to just fuck herself already, but she needs to put on a show. She moves her fingers over the dark curls before moving them to her clit and rubbing it slowly. She sometimes shaves for these weekends, and just for them only, but after her last fiasco, she didn’t. “Fuck, baby… Do you see how wet I am?”
“Yeah, doll…” He groans. Emily can see he is trying to contain himself, jerking off slowly to last longer. It makes her smirk. “Touch yourself. Fuck yourself how you usually do.”
“I can do it however I want?”
“Yes.” He nods. His hand moves a bit faster. “Show me how you like it.”
Emily presses her thumb to her clit as she slides one finger inside her. “Oh…” She moans, biting her lip and looking at Oliver. “Baby, it feels so good… I’m so wet…” And since he gave her the green light to do what she wanted, she adds another finger, giving him a show. “Do you wanna know how it feels?”
Oliver nods, watching her finger herself. He groans when she pinches one of her nipples again, and her back arches. “Yes.” His hand moves faster. “Tell me, doll.”
Emily moans, loving the effect she is having on him. “It feels so good…” She moves her fingers faster. “It’s… Hot… And warm…” She bites her lip. “God, so tight too…” Oliver starts jerking off faster. “I want more…”
“More…?” He smirks, forcing himself to slow down his hand. Emily can see he is conflicted between trying to last longer and giving in and making himself come. “Add another finger. “Fuck yourself, doll.”
“Fuck, yes, baby…” She moans as she enters her pussy with another finger and starts pumping in and out faster. The only sounds filling the room are the wet sounds of her fingers and her moaning. “Yes, yes, Oliver.”
“Keep going.” Oliver is starting to lose control. Emily can see him sweat with the effort of holding back. “I want to see you come.”
“Close… So close,” She moans louder and louder. She makes sure to look him directly in the eye. She even has to fight the urge to throw her head back in pleasure so she can keep looking at him. “Please, baby, let me come…”
“You can come.” He groans. “Come for me, doll.”
“Oh, Oliver!” She practically screams as she continues fucking herself. “Yes! Yes!” Sweat falls down her body. Her nipples erect and hard. Her hair a mess, as well as the rest of her. But it feels so good to come in front of a man she just met 30 minutes ago. Her legs shake until she collapses over the bed. “That was so good, baby…”
“Lick them clean,” He commands, finally letting go of his dick. And Emily nods and opens her mouth and sucks her own fingers, looking at him. “That’s it, doll.”
“Umm… Can I touch you now, baby?” She asks, crawling towards him. “You are so big… I can’t wait to touch you.”
He nods, moving closer to the bed, his dick bouncing with each step. “You can touch.”
Emily smiles, taking Oliver’s thick dick in her hand, and starts stroking it slowly. She sits back on her heels. “Can I taste you?”
“All yours, doll.” His hands are already on her head, his fingers tangling in her hair. He pushes her head towards his dick until her mouth is practically on his tip.
She sticks out her tongue and licks his entire length. Then she focuses on the tip, wrapping her lips around it and tasting the salty precum. She starts bobbing her head, making him moan. She pulls back, looking at him with fluttering eyes, “You taste so good…”
Oliver pushes her head, making her take him deeper into her mouth. Her hand moves to the base of his dick, stroking him at the same time as she sucks him. He moans louder, his fingers digging into her hair. She moves her hands to his thighs and moans against him. The vibrations around his dick make him lose control and start moving his hips at the same rhythm as her mouth. “Fuck, doll, you’re so good at this…”
Emily knows he is close. She knows it because his grip on her hair is tighter. Because he is starting to thrust into her mouth faster. Because the muscles in his stomach start tightening. So she moves one of her hands to his balls, playing with them as she keeps sucking. She relaxes her throat to go deeper.
A part of her wants to slow down so he can fuck her, but the other wants to taste him. The weekend is long, she thinks, I can get someone to fuck me later. So she works even harder to make him come.
“Fuck!” He moans when she starts to suck harder. “I’m gonna come.” Emily keeps sucking, humming on his dick. “I want to come in your tits, doll.”
So Emily lets go, moving away from his dick for a couple of seconds so she can look at the mess she is making of him. She loves it. She then takes his cock into her hands to put it between her breasts. She squeezes them together and moves up and down his length. “Do it, baby.”
That is when he loses control. Completely loses it. He closes his eyes, groans, and moans, coming all over her chest. Emily doesn’t stop until all of his hot, sticky cum is all over her. Then she moves her fingers to take some of it and brings them to her mouth. “Fuck, doll. You’re amazing.”
“And you taste great, baby,” She mutters as she takes some more of his cum and sucks her fingers again.
He smirks, taking her face into his hands and kissing her again. “Let’s do one more thing, doll…”
“Whatever you want, Oliver, baby.”
He gets into the bed, lying on his back. “Sit on my face. I want you to come all over my mouth.”
And who is she to say no to that? Not to say, it sounds fucking amazing.
She moves over his face, not bothering to remove her panties. She has a hunch he is going to want them there anyway.
And she is right. He moves his hands to her hips, pulling her down and pushing them aside, and licks the entirety of her slit.
“Fuck baby…” Emily has to bite her lip to stop herself from screaming. She is so turned on and still sensitive from her previous orgasm that she doesn’t think it will take her long to come. “Don’t tease me…”
He moves to lick her clit, taking it into his mouth and sucking slightly. Emily actually screams this time. Then he moves down, entering her with his tongue. Emily starts grinding against his mouth, needing more.
His tongue goes back to her clit, sucking and licking as two of his fingers enter her dripping pussy. “You taste so sweet, doll.”
“Keep going, Oliver.” She moans, grinding and moving so his fingers go deeper. When he adds another one without warning, she throws her head back. “Ah! More, baby. I need to come…” He seems to take it as a command because he curls his fingers and sucks hard on her clit, making her come undone. “Oh fuck.”
Emily’s legs are shaking, and it takes her a little bit to find the energy to move away from his face, especially because he keeps licking her. She lies down next to him, panting. “That was amazing, doll.”
Emily turns to kiss him. “I’m going to take a shower now.” He nods, looking as spent as her. “You were the best way to start this weekend, baby.”
While she is in the shower, Oliver writes down everything they did, counts the money, and leaves it on the table for her next to one of his golden coins for the weekend.
- Make out session - 80$
- Watch a woman please herself - 350$
- Woman pleases man, no penetration - 400$
- Man pleases woman, no penetration - 400$
- Acts with lingerie on - 75$
TOTAL - 1305$
When she comes out of the shower, she puts her dress back on, takes the money and the golden coin – after all, it’s hers to keep after everything they did –, and kisses Oliver goodbye.
She smirks as she walks back to her room. Not a bad way to start the weekend.
Notes:
Well, I hope you liked it! Please let me know what you think about it, and if you have anything you want to see for the following chapter/requests for next chapters, please let me know in the comments! (I’m open to almost everything haha)
I don’t know when I’ll have the next chapter. But the moment I have time (and a little inspiration), it shouldn’t take long (I was so excited to write this that I wrote it in less than 24 hours).
Chapter 3: Saturday, February 9th, 2008 - Jack
Summary:
Emily’s first Sin to Win weekend.
Notes:
I’m back already with another chapter!
I have to be honest, I don’t know if I’ll ever update this quickly again because life is hard and sadly responsibilities exist (let’s cry about it together), but I have started two other chapters, so it might not take too long either.
Anyway, I hope you enjoy these 4K words of pure smut.
(See the end of the chapter for more notes.)
Chapter Text
It is Emily’s first Sin to Win weekend. She was invited by Anna, a friend of a friend. She doesn’t know why she thought it would be her thing. She is pretty sure it isn’t what you expect from an FBI agent. Maybe it was because she knew her from before. Anyway, she is glad she told her.
Still, she can’t help but be a little nervous. She orders a whiskey soda to calm her nerves. She looks around, and all of the choices feel overwhelming. But she reminds herself that the point of this weekend is to let go and have fun. And to give up control.
She has been thinking about this for weeks now. Ever since Anna added her to the list, she had been trying to get the courage to do it until she finally decided to go to one. She had to get ready for it first. Think about what she wanted to do. Who she wanted to be.
She chose a fake name: Irene. She liked that she didn’t have to be herself for a few days. It felt nice to be someone else – this time, be whoever she wanted to be, not who she had to be. Not for a mission but for fun.
She bought a couple of sexy dresses for the occasion. Three lingerie sets. One for each day. Even though she didn’t get to use the one she picked for Friday the way she intended to, since she ended up chickening out after a couple of drinks at the hotel bar.
She doesn’t usually shave, but for this weekend, she did.
She is a little worried that all of the preparation won’t be used because she is too nervous to do something.
But then, a handsome man touches her shoulder, pulling her out of her thoughts. “Hi there, beautiful.”
“Hello,” She says, a little startled by the sudden interruption of her train of thought.
“Didn’t mean to scare you.” He smiles charmingly. “I’m Jack. And you are…?”
“Irene.” She smiles, feeling her stomach do a little twist with nervousness.
“Hello, Irene.” He shakes her hand. “Can I buy you a drink?”
Emily smiles, biting her lip – part act, part not. “I’d like that, Jack.”
He turns to the bartender and asks for ‘another drink for the pretty lady’, and the bartender brings it to her almost immediately.
Jack looks at her again as she takes a sip of her glass. Emily wonders for a couple of seconds if Jack is actually his real name, but then she realizes she doesn’t really care. “So you come here often?”
“Not really.” She takes another sip to try to look less nervous. “You?”
“Sometimes.” He drinks from his own glass. “What brings you to Atlantic City, then, Irene? Business? Fun?”
“Fun.” Emily nods. “And what about you?”
“A little of both.” Jack leaves his glass on the counter. “Came for business for the week, fun on the weekend.”
They make small talk for a few minutes, laughing and drinking. Emily doesn’t dare to say anything because how would it look if he didn’t know what she was talking about, and he was actually just flirting with her. The last part wouldn’t be too bad, but she didn’t come here to just hook up with a guy from a bar. Well, she did, but not like this.
“So what brings you here?” Jack asks again. “Really.”
“I already told you. Fun.” She thought about it too much, about how weird it would be if she said something that she can’t say anything now. “Just a weekend outside of home. You know. Hotel, bars, casinos.”
“You sure you didn’t come here to sin?” He raises an eyebrow.
It takes Emily a few seconds to catch it and connect the dots in her head that Jack really was there for the same thing as her. Kind of.
“Oh,” She mutters, and then she nods slightly.
He chuckles softly, but it doesn’t sound mean. “First time?”
Emily nods again. “Is it that obvious?” She feels her cheeks getting hot.
He shakes his. “Just a little.” Emily knows he is just being nice, but she smiles anyway, maybe just being nice herself. “We all have a first time here, though.”
“Have you had many weekends like this?”
“A few.”
“And what are they like?”
“Fun.” He smirks. “Really fun.”
“And what do you like?” Emily asks, trying to test the waters.
“Control.” His voice gets lower, and he moves closer to her ear. One of his hands goes to take Emily’s hair out of her face. “Is that something that you’d enjoy? Giving up control to me?”
Emily nods without thinking. She never gets to do that, to give up control. Not even in her sex life, at least not until now. With every girl and boy she has been with, she was the one in control. She wanted – maybe even needed – to see if she liked not having that control. Just letting go.
“Yes.”
“Then you know what you have to do, right?”
Emily nods. She leans in and whispers, her voice a bit breathy. “Sin to Win?”
And he takes a golden coin from his wallet and puts it in Emily’s hand. “Let’s go to my room so I can show you a good time.”
Emily smirks, taking his hand with excitement, and follows him. Jack’s hand moves to her lower back possessively, and it makes her knees go weak for a few seconds.
She is really doing this. She is finally doing this. She is excited. And wet. And horny.
So she lets herself truly become Irene and lets go of all control.
In the elevator, he moves his lips to her ear, kissing and licking all the way down to her jawline and neck. Emily’s breath becomes heavier, and a little whimper leaves her mouth. It surprises herself that she even does that, but she also likes the fact that she does.
They kiss all the way to his room, stumbling blindly as they walk. Their tongues meet, their teeth scrape against each other’s, and little sounds leave their mouths.
Jack barely manages to get his key card and swipe it to open the door without letting go.
When they are inside, Jack closes the door, pins Emily against it, and starts kissing her roughly again. Emily moans when he sucks against her pulse point. Then he bites the same skin, licks it, and sucks it again. Emily knows there is probably a hickey already there and that she will have to wear a turtleneck when she goes back to the BAU next Monday, but she can’t bring herself to care right now.
She throws her head back to give him more access. And he keeps sucking, and licking, and biting, and repeat.
Jack’s hands find the zipper of her dress and pull it down, letting the blue dress fall to her ankles. Then, she unclasps her bra, also blue, and throws it somewhere in the room. He leans in and starts sucking, and licking, and biting over there, too.
“Fuck, yes…” Emily arches her back into Jack’s mouth when he sucks on her nipple, his teeth grazing it slightly and then licking it to soothe it. She knows there is a wet spot on her underwear, the last thing left on her body. “Oh, fuck…”
She loves that he does everything, and she doesn’t have to think about anything other than how good everything feels. She never felt so out of control and so good at the same time.
Jack moves his hands down Emily’s stomach and to her center. He teases her from outside her underwear. “So wet already…” Emily just nods, speechless. “Let’s take this off, too.”
Emily nods again, letting him slide her underwear down her long legs. Then, his long fingers move to her wet folds, teasing her over her clit.
“Jack…” She pants. “Baby, a little more…”
“Patience, Irene…” For a moment, she had forgotten she wasn’t herself. But it makes it feel much better, because Emily would never do this. “Good girls need to earn their rewards.”
And the thought of being a good girl makes Emily go weak in the knees. She nods. “You’re right. I’m sorry.”
Jack keeps teasing her clit. Emily bites her lip to stop the little whimpers that leave her mouth. “Sir.” He whispers against her ear. “You’ll call me sir tonight, understood?”
“Yes, sir.”
He keeps moving excruciatingly slow. She tries to move to get more friction, but he keeps her pinned against the door, and the only thing she can do is moan. When he slides one finger inside her, even though she wants more, she throws her head back in pleasure. “So needy already, aren’t you?”
Emily is nodding before she realizes. “Please, Sir…” And she starts grinding against his hand, trying to get more friction. More anything.
“Did I say you could move?” Jack’s voice is lower than before, and he removes her finger from her, and the thumb that was playing with her clit too. Emily pouts and shakes her head. “Use your words, Irene.”
“No, sir.”
“Tonight, you get what I give you…” Emily nods. “Good. Go to bed.”
As Emily walks to the bed, she realizes that he is still wearing all of his clothes, and she is already completely naked. She crawls into the bed, lying down over the pillows. “What now, sir?”
“Lie on your stomach.” His voice is low and breathy. Emily can see him undoing his shirt before she turns around. “Hands on your back.”
She can’t see him, but she can hear him looking around, maybe even going through a drawer, but she is feeling too overwhelmed thinking about what is going to happen next to focus. Then, she feels him moving close to her.
Without a word, he moves her hands to her back and ties them together with something soft. Probably silk, but Emily can’t place it right now. She would never admit it, but she can feel herself grow wetter by the moment.
“You didn’t listen…” He whispers, tying the knot tight on her wrists. “Good girls do…”
“I can be a good girl, sir…” She bites her lip to stop the whimper that is threatening her throat.
“I believe you…” He moves his fingers up and down her back, making her shiver, goosebumps appearing all over her spine. “But you still need to learn what happens if you’re bad.” His hands move to her ass and squeeze it. This time, Emily just whimpers. “I was thinking… Maybe 10 spanks. What do you think, Irene?”
“Y-yes,” Emily mutters. It’s the first time she has ever felt like this during sex. “I deserve 10.”
She feels something cold rubbing her left ass cheek, but doesn't move. Emily thinks it might be something wooden. “Count for me.”
The first blow is hard on her left side. But it makes her moan. It stung, but it also made her incredibly horny. She never thought she could be so turned on by this. “One.”
“Good girl.” Another blow to the other side.
Her back arches, and she closes her fists around the soft silk tying her wrists together. “Two…”
By the fifth one, Emily has to bite her lip hard to contain her moans. Jack rubs the paddle over her ass slowly, admiring the redness and the heart imprints left by the paddle. “Halfway there…”
“Six!” She half moans as the paddle connects with her skin again. Her hips buck against the mattress unconsciously. She can imagine how she looks: tied up, ass red, dripping on the sheets, face on the pillow to stop herself from screaming. Before she can finish the thought, the paddle finds her sensitive skin again. “Seven.”
She can’t quite think straight anymore, but she thinks it must be quite the sight. “Eight.”
For just a moment, she thinks about how she will probably be sore for a while, or how some sort of bruise might linger for a few days. But she is too turned on to care. “Nine.”
“One more.” He whispers, rubbing the paddle against one cheek as his other hand squeezes the other. “One more and I’ll make sure you will never forget this night.” Emily is sure she won’t. Jack moves his fingers to Emily’s pussy, just teasing her entrance for a few seconds before pulling out and delivering the last blow.
“Ten!” Emily cries out. Her skin burns, but it burns so good. Emily is glad this was the last one, not because she wanted it to stop per se, but because she is sure she would have come with just two or three more. He lets go of the paddle, letting it fall to the floor, and his hands move to her ass.
“Good girl…” He massages her sensitive skin, making it burn even more, but she doesn’t want him to stop. She wants more. More anything. After a while, his fingers move to her wrists and untie her. “Turn around, baby. We’ve just started.”
Emily turns around, lying facing the ceiling. She moves her wrists slowly, trying to get used to the feeling of not being tied up again. She then looks up at him as he is unbuttoning his shirt. “What should I do now, sir?”
“Kneel.” His shirt is off by a matter of seconds, and his pants and briefs soon follow. She can finally see him: tall, muscular, big dick, hard already. She can’t help but think she was lucky he approached her in the bar. “On the floor.”
Emily nods, carefully crawling to the edge of the bed and moves to kneel on the floor in front of him. He walks even closer to her, stroking his dick slowly until the head is grazing her lips. “Open your mouth.”
Emily obliges, opening her mouth and sticking out her tongue to tease the head, but he quickly pushes his whole length inside her mouth, and his hands move to get a good grip of her hair. Emily groans, and the vibrations make Jack lose control and push even deeper. Emily gags a little, but she quickly relaxes and starts bobbing her head slowly and sucking with each move.
His grip on her hair tightens, moving her head faster. And she just lets him, moaning around his cock. She loves this. She loves that she is doing it. She loves not being in control. She loves being someone else for the weekend. And especially, she loves that she is having so much fun already.
Jack pulls away from her mouth abruptly, leaving Emily gasping in front of him, saliva falling down her chin. She looks up at him from the floor, waiting for him to say or do something else.
“Stand up, Irene…” Emily does. Her knees are somewhat red from kneeling for too long. He smirks, his eyes moving between her and the floor-to-ceiling windows. Emily has an idea of what he wants, but she waits for him to say it. And he does. “I’m going to fuck you against the window.”
She walks towards the window slowly. There is still some light outside, and she can see people walking on the street. The thought of any of them looking up kind of excites her. She knows that the chances of being seen are not that high. It is getting late and dark. They are on the 15th floor. And people don’t usually look up to see if someone is being fucked against a window. But still, someone could look up at any moment and see her. The thought makes her wet.
She has never done anything so dirty. It felt forbidden before now. She feels sad she didn’t hear about these weekends sooner. And she knows she will be coming back soon again, even if the weekend isn’t over yet.
He walks behind her, pressing himself to her back and making her move closer to the window. “Like the view?” Emily chuckles and nods, looking back to him. “Let’s give them a better one.”
He pushes Emily’s entire body to the window, making Emily shiver. “It’s so cold…”
“You’ll warm it up in no time, baby.”
Emily can feel Jack’s dick against her ass. The cold glass against her sweating body makes her dizzy for a couple of seconds. His hands move to her hips, squeezing them, and then down to her wet cunt. “Um…” He mutters as he rubs her clit slowly. “Someone’s ready.”
“Yes…” Emily sighs. “I am, sir. Please fuck me…”
“Well… Since you asked so nicely…” He positions himself, teasing her entrance slowly. Her back arches, her breasts pressing hard against the window, the cold making her nipples peak. And then, he pushes inside her with one quick thrust. “Fuck.”
Emily moans. Her forehead presses against the glass as she looks down, trying to see if someone is watching. She doesn’t know if it is wrong that she kind of wants someone to look up to. “More…” She sighs. “Please… Sir…”
He keeps moving slowly, making Emily go crazy. “Do you want me to fuck you hard? Is that what you want?” Emily nods frantically. “Use your words, Irene.”
“I want you to fuck me hard.” Emily can feel her cheeks warming, and she can imagine how red they might look. “Please, sir, fuck me hard.”
“God…” Jack can’t resist himself, and he starts thrusting faster and deeper into Emily’s cunt. It makes her back arch for a few seconds, showing the condensation in the window where her breasts were. “You feel so good.”
“Oh god, yes!” Emily moans louder as his hand moves in front of her and starts rubbing her clit as he keeps pounding from behind. Emily looks down, trying to make out if someone is looking at them.
“You’re right under the casino sign,” Jack whispers against her ear like he was reading her mind. “That’s what you’re thinking… Aren’t you?” He teases with each thrust. “They might be looking at it… They might be looking at you…”
Emily’s eyes roll. Her pants fog the window. Jack grabbed her hip with one hand and, with the other, grabbed her hair and pulled. “Fuck! More… Please… More…” Emily moans. “Please…”
She could feel the sweat all over her body and his from being pressed to her. It is messy and fast, and dirty. And so incredibly fun.
He pulls her hair again, making her look to the side and press her cheek to the window. His thrusts have become more erratic, the grip on her hip tighter, and so has the one in her hair. “Fuck, baby. I’m so close.”
“Yes!” Emily lets out a long, guttural moan and nods against the glass. “I’m close too. Can I come? Please let me come, sir.”
The hand on her hip moves back to her clit, rubbing it fast and making Emily scream. “Wait until I do,” He whispers, his voice raspy. “Wait until I come inside you. Then, you can come.”
Emily nods. She bucks her hips, trying to match his rhythm, but he is moving with no clear pattern, and she knows he is about to come. So she moans louder, trying to push him over the edge already, so she can finally come.
It doesn’t take long before it happens. Jack starts moving even faster until he suddenly goes still, and Emily can feel his hot cum filling her. Her eyes roll, and she moans at the feeling. “Fuck, fuck, fuck.”
She comes too. Her legs go weak and shake. She is only still standing because Jack is pressing her hard against the glass, and his hand is still gripping her hips still. And Jack keeps pounding into her until her orgasm is over.
“God, that was beautiful,” He whispers as he pulls out slowly. “You’re so hot when you come.”
Emily chuckles, turning around to face him. “Thanks. Didn’t see you, but I’m sure you’re not bad yourself.”
His hands move all over her body, and Emily is so sensitive that just the touch makes her whimper. “I want to see you come again,” He whispers as he presses her back to the window, but this time with her back to it, and kneels in front of her.
Emily is so sensitive that she doesn’t know if she can take it. Just him touching her skin sent her into overdrive, so she can’t even imagine what him eating her out will do to her.
Before she can overthink it, he leans in and licks her pussy from top to bottom. Just that alone makes her legs shake again. He moves his hand to her stomach to keep her steady, and she throws her head back to the window with a long moan. “Fuuuck.” Then he moves his mouth to her clit, licking it before wrapping his lips around it and sucking it hard. Emily’s vision gets all blurry, and she can’t make a coherent thought.
He keeps sucking and licking, and after a while – probably just a minute or two, but to Emily it felt like an eternity because she is so close to coming again already – he pushes two fingers inside her sensitive cunt and moves them in and out fast.
Emily can’t stop moaning and screaming. That, and the wet sounds of Jack’s fingers and mouth, are the only sounds in the room. And when he curls his fingers just right, that spot perfectly, she comes again.
She grinds against his mouth, trying to prolong her orgasm as long as possible, and he lets her. He keeps his work until she calms down and has to tug at his hair because it becomes too much.
“Fuck, you’re good at that.” She chuckles. “I can barely feel my legs anymore.”
“Thank you for letting me see you come again.” Jack chuckles, standing up and helping her to the bed. “How was that for the first Sin to Win?”
When she sits on the edge of the bed, he lets go, and she lets herself fall into the soft mattress. “So fucking fun.” She laughs softly, looking at the ceiling. “And exhausting.”
“You did great.” He chuckles. “Wanna hit the shower?”
“I can’t have another orgasm without exploding.” She chuckles too, only half joking.
“I meant alone.” He shakes her head. “I can’t take more for tonight.”
“Oh.” Now she feels a little embarrassed. “I’m fine, thanks.”
“Sure.” He walks to the desk on the side of the room, takes a little paper, and starts to write something down.
Emily doesn’t know if there is some sort of protocol, so she waits until he tells her otherwise. She would rather it be a little awkward this first time and know what to do the next time than be awkward when she doesn’t have an excuse.
Then he takes his wallet and pulls out some money.
He walks to the bed and he gives it all to her.
- Makeout session - 80$
- Tying up or restraining - 150$
- Marking - 150$
- Impact play - 300$
- Woman pleases man, no penetration - 400$
- Sex, no condom - 500$ + 50$ - 550$
- Exhibitionism - 300$
- Man pleases woman, no penetration - 400$
Extras: First time (First Sin to Win) - 470$
TOTAL: 2800$
“I thought the first Sin to Win didn’t count as a first time.”
“It doesn’t.” He smiles. “But I wanted to give you a little extra. Consider it a welcome gift. And you get to keep the coin.”
Emily should find it weird that they are doing this naked, but she doesn’t. “Well, thank you.”
“Don’t mention it. I had so much fun tonight.”
Emily smiles kind of awkwardly before standing to go for her clothes and get dressed again.
Before leaving, she asks, “The writing things down. Is that a you thing or a regular thing?”
“A regular thing.” He shrugs. “They tell us to do it when we join.”
Emily nods, walking to the door. “I had a great night, Jack. Thank you.”
“Thank you back, Irene.”
And then she goes back to her room.
When she gets there, she runs herself a bath to get all the sweat and tiredness off her body. She puts her money in her wallet and the golden coin too.
2800, almost 3000.
Not bad for a first time.
Emily doesn’t know if she will go out again tomorrow, but she does know she will be back for another weekend sooner rather than later.
Notes:
If you have any ideas for what you want to see in the following chapters, please let me know in the comments or on my Tumblr (@ellesleatherjacket). I’m here for that!
Also, I’m already writing two other chapters that are definitely more intense than this, so have patience with me, I promise it will be worth it!
Chapter 4: Sunday, April 28th, 2012 - Elle and Liam
Summary:
Emily meets someone in a bar who looks familiar, even if she can’t quite place her. One thing leads to another, and things end up in a threesome. Needless to say, it ends up being Emily’s favorite Sin to Win weekend.
Notes:
Hello!
I know this took a while, but this is the dirtiest thing I’ve ever written, and unfortunately, I still have responsibilities. But here you have almost 5K words of dirty, dirty smut.
Also, my girl makes an appearance because Elle and Emily are so hot, and together even more. Hope you enjoy it!
(See the end of the chapter for more notes.)
Chapter Text
Emily just got to the hotel bar when the bartender handed her a drink before she could even ask for it. It usually takes a little longer than this for someone to buy her something, but she is not completing. “From that girl over there.”
She looks where the bartender pointed and sees a brunette with shoulder-length hair. A really hot brunette. She is not complaining about that either. She doesn’t mind taking a break from Sin to Win if it means sleeping with a hot woman, especially after the very successful weekend she already had.
She takes a sip from the glass, looking at her and inviting her to come. And the woman does. She is just wearing a pair of jeans and a shirt that is a bit too tight and a leather jacket, but Emily can’t keep her eyes from her. And she suddenly feels a little overdressed in the blue dress she chose for the night.
She looks kind of familiar, but Emily can’t quite place her, but she isn’t trying too hard either.
“Hey,” The woman says, sitting next to her. “Hope that wasn’t too forward.” She points at the drink, and Emily shakes her head. “I just had to get your attention before someone else did.”
“Well, you’ve got it,” Emily says with a flirty smile. “Not difficult looking like that.”
“Thank you.” Her hand moves to Emily’s arm. “You look great, too.”
“Thank you.”
“I’m Elle.”
“Emily.” She stopped using a fake name a while ago. She had spent too long using a fake name last year in Paris. And it was more exciting when the person she was having sex with moaned her name instead of a made-up one. And she definitely wants to hear Elle doing it.
“It’s not the first time I’ve seen you here.” And Emily knows she means in a Sin to Win weekend because it is the first time she has ever been in this hotel. “You were always with company, though. I was looking forward to talking to you. You seem like you know what you’re doing… And how to have a good time.”
“I knew you looked familiar.” Elle chuckles, moving her hands as if it were a big deal. “I’m glad you came to say hi. And I definitely know how to have a good time.”
“Yeah?” Elle teases, and Emily nods either way. “Because I had a proposition for you…”
“You do?” Emily smirks. “What is it?”
“We could go to my room and have some fun…” Not a bad idea, Emily thinks to herself. “Or I could call a friend who would enjoy watching us, maybe joining for a little while…” Elle pauses for a couple of seconds. “And have a round two alone after he leaves.”
“What’s your friend like?” Emily asks, even though she has already decided on number two.
“Handsome, tall, big…” Emily raises an eyebrow. “And rich. The kind of rich that doesn’t care how much they spend…” Elle leans closer to Emily. “Either way, you and I are ending up in my hotel room and having some fun…”
“Call your friend. Let him spend two coins at once.” Elle reaches for her phone to text this mysterious friend. “But if you promise me we will have that round two alone after.”
“I was counting on it,” Elle whispers against her ear. “Let’s get going to my room… You and I are going to have so much fun tonight.”
“I can’t wait.” Emily smiles as she follows Elle.
In Elle’s room, Elle kisses Emily, her hands tangled in her hair, pressing her body against hers.
“Fuck… How long until he gets here?” Emily asks in between kisses. “Because I need you to fuck me already.”
“Patience…” Elle whispers against Emily’s lips. “I’ll make it worth your wait.”
Emily leans in to kiss her again as they wait until there is a knock at the door. “Finally.”
Elle chuckles when she opens the door. She kisses the man on the lips quickly, as Emily waits and says. “Liam… Come in… Let me introduce you to my new friend, Emily.”
He walks inside, and Emily waves at him, waiting for Elle to do something else.
“Hi.”
“So you're interested in a show from us?”
“Come on, Elle.” He chuckles. “You know I am. Especially with someone so gorgeous.”
“Am I not good enough for you anymore…?” Elle teases with a little pout, and Emily is in awe of how Elle can control the situation – control him. Liam goes red.
“No. No, I just…”
“Breathe…” Elle laughs. “I’m kidding.” She looks back at Emily. “She does look gorgeous…” Emily gets the point and walks closer to Elle, kisses her again, and feels he can’t take his eyes off them, which makes her feel confident – powerful. “Liam, dear,” Elle says between kisses, not even bothering to look at him. “Why don’t you get on that chair so you can enjoy the show?” He nods and sits on the chair in front of the bed. “If you’re good, we’ll even let you join.”
“What are you going to do?” He asks.
“What do you want to see?” Elle shoots back.
“Fuck her.” He says low and soft, like he was waiting for her approval. “I’ll pay as if I did.”
“You heard him,” Elle smirks, moving towards Emily. “Let’s give him a show.”
“With pleasure.”
They kiss as Liam watches, but for a while, Emily forgets he is there. Elle’s hands move to Emily’s back to unzip and then take off her dress. Emily lets her but doesn’t let go of Elle’s lips.
They pull away just for a few seconds so Emily can step out of the dress. Then Emily takes off Elle’s shirt and throws it out of the way. Her lips move to Elle’s chest, kissing down her neck to the top of her breasts, all over the line of her bra, focusing on the scar there for a few seconds. She has no idea how she got it, and she doesn’t think she’ll find out. But she knows it feels nice to feel something good on your scars. The moans leaving Elle’s mouth make her continue more eagerly.
Elle unhooks Emily’s bra as she keeps kissing her breasts and lets it fall. Then she pulls Emily away so she can move her hands to Emily’s, squeezing them together for the enjoyment of the three of them.
“Take off your panties,” Elle tells her, and Emily immediately obeys. “Give them to him.” And Emily does, walking completely naked towards Liam. She gives him her underwear, and for a few seconds, they are both frozen in place as they wait for Elle to tell them what to do. “Come back here, Emily. Let him keep them so he can use them later.”
Emily nods, walking back to Elle. “What should I do?”
“Take my clothes off,” Elle tells her, taking Emily’s hands to move them to her back so she can unclasp her bra. “I want to fuck you already, and I’m sure Liam wants to see it.”
Emily turns her head for a couple of seconds, watching Liam nod as he pats his groin over his pants, because the moment he is out of sight, the only thing in her mind is Elle, and she keeps forgetting he is in the room with her.
The moment the bra is out of the way, her mouth gives Elle’s breasts her whole attention, kissing and licking them. She takes her left breast into her mouth, sucking on the nipple before moving down to her stomach, kneeling on the floor, until she is just over the waistline of her underwear. She stops, moves her fingers to the red underwear, and pushes them down Elle’s legs.
Emily looks up from the floor, her mouth hovering over Elle’s cunt. “Can I taste you?”
Elle nods, moving her hands to Emily’s head and pushing her closer to her dripping pussy. Emily starts kissing Elle’s thighs, taking the time to enjoy it. She moves slowly until she is just over Elle’s clit, She leans in to kiss it before moving down and entering her with her tongue, humming at the taste. It makes Elle’s hands tighten on her hair, so she does it again.
Elle lets her keep eating her out for a few minutes before tugging on her hair to push her away, and Emily lets go with a pout.
Elle leaves her there on her knees as she walks to get something from her bag. She watches her, the same way Liam is, as she takes a harness and puts it on. She can see Liam getting harder under his pants, but she can’t blame her because she is getting wetter at the sight too, especially when they watch Elle put a red dildo on it.
She walks slowly towards Emily, still on her knees, and positions the strap right next to her face. “Open for me, baby.” And Emily does, wrapping her lips around Elle’s strap and bobbing her head as she sucks on it, making sure the base hits Elle’s clit each time.
Emily looks at Elle the whole time, watching how her eyes go dark, and she moans each time Emily makes the dildo press against her clit. The look in her eyes makes Emily wish Elle would fuck her already.
Elle seems to be thinking the same thing, because she pulls away from her. “Get on the bed.”
“How do you want me?” Emily asks as she stands up and moves towards the bed.
Elle looks at Liam, signaling him to answer instead of her. “From behind. Hands and knees.”
Emily obeys, getting on her knees and leaning in to rest her body weight in her hands, facing the window so Liam can have the best view of her body when Elle fucks her.
She feels Elle’s hands on her waist, squeezing for a moment before she leaves. Emily turns around to look at her with a pout. “Come on, Elle…”
“Patience…” Elle chuckles as she looks through her bag again. “You think too much, Emily…”
“I wouldn’t be thinking as much if you were fucking me already.”
“Careful,” Elle says as she turns around. “Or I won’t fuck you at all.” She walks towards the bed, her hands lingering on Liam’s shoulder for a few seconds. “I could fuck Liam instead.”
Emily shakes her head. She has never been so turned on in her life, and the idea of having to wait any longer kills her. Even if she is 90% sure, Elle wouldn’t do it. She is not risking that 10% chance. She needs Elle inside her already.
“This will help you not think so much,” Elle whispers against her ear. Then she covers her eyes with a silk scarf. And it makes Emily even wetter if that was even possible. “I want you to just feel,” Elle tells her as she finishes tying the scarf on the back of her head.
Everything is black.
Emily nods as she waits for whatever Elle wants to do next. She can hear something moving. Then she feels Elle’s hands back on her waist. “Doesn’t she look pretty like this?”
“Fucking gorgeous.” She hears Liam groan, and even though she can’t see him, she knows she is having an effect on him.
Suddenly, one of Elle’s hands moves to her dripping cunt, entering her with two fingers. “Fuck!” She moans, arching her back when Elle’s other hand moves to her clit. “Mhmmm, yes…”
“So wet already…” It is not a question, but Emily nods either way. “Look at her,” She tells Liam. “She’s so desperate. So needy for my dick and for you to see how she takes it…”
“Give her what she wants…” Liam mutters. “Fuck her already.”
“Well, if you insist.” Elle shrugs as she pulls her fingers out of Emily and quickly positions the strap on Emily’s entrance. She pushes inside in one fast, deep move, making Emily gasp and arch her back to try to make Elle go deeper.
“Fuck…” Emily moans as Elle starts moving, her fingers gripping her waist as she does. She moves slowly, but each thrust is deep, and it hits just the right spot. If her eyes weren’t covered by the scarf, she would roll her eyes with each one. “Yes…”
She loves these weekends because she gets to have fun with no strings attached. Have some random man fucking her until she comes and forgets her own name. But a girl who knows what she is doing with a strap… That is something she loves.
And Elle definitely knows what she is doing.
Elle leans in, takes Emily’s hair in her fist, and pulls to make her arch her back further, making Elle hit the perfect spot with the new angle. “Oh God…”
Liam groans in his chair. “Do you like what you’re seeing?” Elle asks him.
“So fucking much.” He replies in a low voice.
“You can touch yourself if you want to.” Elle gives him permission as she moves faster. “She is such a pretty sight. It’s a crime not to enjoy it.”
“Finally.” He moans. Emily can hear him pulling down the zipper of his pants and then a low moan. “Fuck her harder.”
And Elle does. She moves faster. Deeper. And Emily can’t contain her moans. She doesn’t want to either.
“Slow down, tiger…” Elle says to Liam, Emily assumes. “Don’t go too fast, or you won’t be able to join us later.”
By the satisfied chuckle that leaves Elle’s mouth and how his moans slow down, Emily assumes he does.
But Elle doesn’t. She keeps pounding into her, fast and deep. The hand on her hair moves to her back, pushing her down. Emily lets her until her face is on the mattress.
When Elle moves her other hand to Emily’s clit and starts rubbing with the same pace as her thrusts, Emily loses control.
“Oh, fuck, Elle…” Emily moans. “Let me come. Let me come, please.”
Elle’s hand moves faster on Emily’s clit. “Come for us…”
Emily screams against the mattress as Elle keeps fucking her. She loses control completely if she hadn’t already, as Elle’s thrusts make her move into the mattress. The fact that she can’t see anything makes it even better. She can hear Elle’s moans as she pounds into her, mixed with Liam’s. And before she realizes, she is clenching around the strap-on as she mutters unintelligible things as she comes.
But Elle doesn’t stop. She keeps the same relentless pace. “Come on, Emily… You can give me one more…”
And who is Emily to contradict someone as gorgeous, and who is fucking her so damn well?
It only takes her a couple more minutes until she is coming around Elle’s strap again as she moans a mix of “Oh fuck, Elle!” and “Yes! Yes! Yes!”
When she finally stops moving and pulls out, she carefully unties the scarf that covered her eyes. Emily turns around to lie on her back as she tries to catch her breath.
Elle gives her a couple of seconds before moving her hands to her chin to make her look to the side so she can see a desperate Liam, doing his best so he doesn’t come on his own, so that he can fuck them both. “Look at what a mess you made of him…” Emily smirks. “Should we let him come on his own, or should we let him join us for a while?”
“I think he’s earned a little fun…” Emily replies as she leans in to kiss Elle again. Even if she tries, her priority here isn’t Liam. She kisses her for a few seconds before whispering against her lips, “We’ve earned it too…”
Elle bites Emily’s lip, looking at her and taking a few moments to appreciate how good she looks right now: naked, freshly fucked, and waiting for more. It drives her crazy.
“Come here…” She tells him. “But take all those clothes off already.”
Liam doesn’t waste time either. It takes him 30 seconds to take everything off and throw it somewhere in the room, and climb into bed with them. He leans in to kiss Emily first. He is desperate already. It makes Emily smirk into the kiss.
Her hands move down his body, teasing every inch of skin, as she looks at Elle instead of him. The sight of Elle, lying down with her legs wide open, the strap pulled to the side so she can touch herself as she watches them, is too good to look away.
One of her hands wraps around his dick, hard and leaking precum already, and starts stroking it slowly, not giving him nearly enough. She has to give him some points in his favor; most men would have come already. He moans against her lips, trying to move his hips to get more friction, but Emily doesn’t give him more than that. Not yet. It’s way more fun to watch him squirm.
She usually isn’t in control during these weekends, and she likes that. But today she is in some sort of control. At least over him. They all know Elle is the one who is actually in charge there. But, still, she is enjoying having that power over him.
Elle’s breath is getting heavy as she fucks herself with two fingers. “Use your mouth.” She tells Emily. “Make sure he’s hard enough to fuck you. I want to see that too.”
Emily nods, moving around the bed as Liam lies down. She kneels next to him, leaning in to take his dick into her mouth as Elle keeps touching herself.
She wraps her lips around his dick and moves down slowly before bobbing her head slowly, her eyes locked on Elle’s. She hums and moans around him, making him throw his head back in pleasure, but she hopes Elle knows she is the real reason they come out of her mouth.
It isn’t long after that when Elle pulls Emily’s face away from Liam. He whines when he loses contact, but looks down after Elle shoots him a pointed look. It makes Emily chuckle.
“Lie down on your back,” She whispers as she moves a strand of her hair behind her ear, making her shiver.
Emily does without hesitation. The moment she is in the center of the bed, Elle moves to straddle her face. “You’re going to fuck her while I sit on her face.” Liam’s cock twitches in anticipation, and Emily opens her legs wider, already waiting for Elle to lower just a bit more so she can finally eat her out. “But, she can’t come until I do.”
God, this woman is going to be the death of her.
Emily nods eagerly because, right now, she would do whatever Elle asked her to. Then, finally, Elle moves down to her face, and she can finally taste her. It has been too long since she had a beautiful woman like this, so she is greedy to get more. She wants nothing more than to make Elle come.
She licks and kisses and sucks on every inch of Emily’s pussy, trying her hardest to make her moan so she can hear those sounds again.
Liam rubs Emily’s clit for a few seconds before pressing his dick against her cunt and pushing slowly inside her, groaning loudly. Emily moans against Elle’s clit, and she starts grinding into her mouth.
Emily loves the taste, the smell, and how Liam starts to quicken the pace. It all feels so intense, but she is having so much fun that she doesn’t care if it is sort of overwhelming.
“Oh, fuck…” Elle moans on top of her when Emily sucks on her clit. “Faster.”
Emily doesn’t know if she is telling her or Liam, but they both obey. Emily moves her tongue in between her clit and inside her as fast as she can, making her moan louder and louder. And Liam starts thrusting faster and deeper.
Emily would be moaning so loud if Elle’s pussy wasn’t muffling her moans, especially when Liam grabs her hips and pushes them upwards to push even deeper into her, and he starts rubbing her clit at the same time.
She works harder on Elle as her moans grow louder and get closer together. She knows she is close, and she desperately wants her to come in her mouth. And, not as important, but almost right there with that, she can feel herself getting close to her own orgasm, and she really wants to be a good girl for Elle and not come until she has.
When Emily sucks hard on Elle’s clit, she gasps sharply. “Oh, fuck. That… Do that again.” And Emily does. “Fuck. I’m gonna–”
Emily doesn’t let her finish. She sucks again, making Elle’s leg shake and her hips jerk and moaning even louder than before. It is the hottest thing she has ever heard.
She continues to lick her to prolong her orgasm, momentarily forgetting about her own needs, until Elle pulls away and lies next to her as Liam keeps fucking Emily.
Elle leans in to kiss Emily, moaning when she tastes herself in her mouth. Her hands move to her breasts to play with her nipples as Liam’s thrusts become erratic as he approaches his own orgasm.
“Fuck…” Emily whimpers in Elle's mouth.
“So close…” Liam groans, looking at Elle and silently asking for permission.
“Come inside her,” Elle says in between kisses, not bothering to get away from Emily’s mouth. “I think that’s what she needs to come. Don’t you, baby?”
Emily nods against Elle’s lips and, in a matter of seconds, his body stiffens as he moves in slow but deep thrusts as he comes, moaning and gasping the whole time.
“Come for me,” Elle whispers against her lips. And in between that, and Liam’s hot release inside her, she comes screaming, and Elle swallows every sound in her mouth as she kisses her.
Liam pulls away slowly and collapses next to them. Elle moves to kiss him, giving Emily time to recover. “That was so hot.”
“Fuck yes, it was.” He chuckles, kissing her back. “You think you’ve got one more in you?”
“Do you?” Elle raises an eyebrow.
“I just wanna watch, darling…”
“What do you think?” Elle mutters as she moves back to kiss Emily again for a few seconds before moving down to her jaw and neck. “Want me to make you come again?”
Emily wants Elle to fuck her until she forgets her own name. She doesn’t care if it is with Liam watching or not.
“Yes.”
Emily nods against Elle’s mouth. “Fuck me.” She sighs as Elle sucks on her neck. “Fuck, I’m yours tonight, you can do whatever you want to me.”
Elle chuckles, moving away from Emily, leaving her panting and staring at the ceiling, and Liam staring at her and how her breasts move with each breath, as he sits back in the chair like he is getting ready to watch his favorite movie.
She comes back just moments later, a pair of handcuffs on her hands and a smirk on her face. “What do you think?”
Emily nods eagerly again, putting her hands in front of her already for Elle. “Please.”
Elle puts the cuffs around Emily’s wrists and closes them shut around them. “How many more do you have in you?” Emily can’t even make coherent thoughts anymore. She can’t think at all. The only thing on her mind is how much she wants Elle to fuck her again. “I guess we’re about to find out then.”
Elle moves Emily’s hands on top of her hand and pushes her legs open and settles herself in between them, her mouth hovering over Emily’s cunt.
She licks all the way from her clit until she dips her tongue inside her, making Emily moan loudly. “Oh, fuck!”
“Keep your hands there,” Elle warns her when Emily is about to move to her head to try to keep her close to her pussy, trying to get more from her. “Don’t make me cuff you to the bed.”
Emily obeys because she is having so much fun that she would do anything Elle told her to do right now, even if she had just met her. She is so captivating, so thrilling… She is pretty sure that from all her Sin to Win weekends, this is the one she is enjoying the most. All because of Elle.
Elle moves her tongue back to Emily’s clit, and Emily loses her train of thought.
She feels like a mess. She is a mess.
She is being so loud, but she has to keep all her energy in keeping her hands where Elle told her. She wants to be good for Elle.
She is sweaty. Her hair is a mess. Still, she feels like the hottest person alive when Elle looks at her from between her legs.
And when Elle sucks hard on her clit, Emily comes, calling Elle’s name and other unintelligible things.
But Elle still wants more. And Emily isn’t going to tell her no.
Emily’s mind is blurry. And in a matter of seconds, one of her legs is on Elle’s shoulder, and Elle is teasing her oversensitive clit with the dildo.
“Please…” She whispers. “Please, Elle…”
And Elle doesn’t tease her anymore and pushes inside her and fucks her fast, just like Emily needs it.
Elle rubs Emily’s clit at the same time of her thrusts, and it doesn’t take her long to come again.
“Come on, baby…” Elle whispers as she kisses Emily, both of them ignoring Liam completely. But when Emily glances at him for a few instants, she seems fine, touching himself as he watches, so she doesn’t waste time looking at anything but Elle and how hot she looks as she keeps fucking her senseless, just like she promised. “Give me one more. Just one more… I’m so closed.”
It takes her just two minutes until she reaches another orgasm, shaking, moaning, and sweating. Emily doesn’t think she has had an orgasm like that. Seeing her coming like that makes her come too, collapsing on top of Emily.
“Good girl…” Elle whispers against Emily’s lips before kissing her, this time softer. Emily thinks she could come again just because of those two words. She pulls out, making Emily whimper, and kisses her again. And again, after she undoes the cuffs.
She lets her panting on the bed, letting her recover and catch her breath after six intense orgasms.
She watches Liam get dressed and go through his things before writing down everything on two pieces of paper. Elle gives him and leaves two stacks of money on top of each other before leaving.
Elle
- Makeout session – 80$
- Watch a woman please another woman – 500$ x 2 – 1000$
- Watch two women have sex – 700$ x 2 – 1400$
- Threesome – 650$
- Toys – 75$ + 25$ – 100$
TOTAL – 3230$
Emily
- Watch a woman please another woman – 500$ x 2 – 1000$
- Watch two women have sex – 700$ x 2 – 1400$
- Blindfolds –100$
- Makeout session – 80$
- Woman pleases man (no penetration) – 400$
- Threesome, no condom – 650$ + 50$ – 700$
- Tying up or restraining – 150$
- Multiple orgasms – $220
- Toys – 75$
TOTAL – 4125$
When he is gone, Elle goes back to the bed, lying down next to Emily before leaning in to kiss her again. “Bathtub?”
“I’m all out of orgasms.” She chuckles weakly, looking at Elle with an amused expression.
“I know.” Elle smirks. “It was so hot. Just a bath.”
“Okay.” Emily smiles. Elle’s fingers caress the burn scars on her chest. She is still not used to people touching her body, and her body tenses unconsciously.
“Sorry,” Elle whispers, moving her hand away when she notices.
“It’s okay.”
“I’ll go run you a bath.” Elle stands up to go to the bathroom.
“Only if you get in the tub with me,” Emily says from the bed. “And if you promise to have a round two in the morning.”
“Deal.”
In the morning, Elle and Emily had round two in bed and round three in the shower before Elle had to leave.
“Hope I see you around here again,” Elle told her as she got dressed. “I had so much fun.”
“I do, too.” Emily smiles. “If you ever see me around, come say hi. We can have some fun together. Maybe even just the two of us.”
“I will. As long as you promise to do the same.”
“You can count on it.”
It isn’t until a few weeks later that Emily sees Elle’s face again.
It isn’t as expected. It isn’t during another Sin to Win weekend. It’s at JJ’s place when they are looking through old photos on a girls’ night.
“Who’s that?” Emily asks, trying to keep herself from making any face that would reveal that she knows her. She really doesn’t want to explain to them how exactly.
“Oh, that’s Elle.” Penelope chimes in, sitting next to them on the couch as she brings a bottle of wine. “She worked with us before you joined the team.”
Oh, shit.
The rest of the conversation is a blur. She can’t focus on anything they say. She can only focus on how much weirder, if that was even possible, if they ever found out that she knew Elle.
Either way, she can’t wait to see her again.
Notes:
So… A little bit of plot might be forming here for future chapters/fics related to this one… But don’t worry, there will still be smut :)
Also, if anyone has requests/something they want to read (for this fic or not) tell me in the comments or in my my Tumblr/Tumblr asks (@ellesleatherjacket)
I hope I can find time to update/post soon!

mazikeensbitch on Chapter 2 Wed 15 Oct 2025 03:24PM UTC
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ellesleatherjacket on Chapter 2 Sat 18 Oct 2025 10:43AM UTC
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