Tif has Sex with Infamous Jacques


Story eleven: Tif Fucks Jacques

This is the eleventh independent story of our teenage whore Tiffany “Tif”. This story accompanies the Katherine “Kat” storyline. The timing of this event aligns with the third night of Module Two Chapter Six in the Kat series. While it is feasible to read any of these independently, this is a carryover story, so reading them in order is beneficial.

Disclaimer: Nearly all chapters with this character have some exposure to young/old, group sex, lesbian sex, ass-to-mouth, and/or cum sharing, etc. If any of these things offend you, please move to another story.


Tif stands in the shower letting the hot water drain over her body thinking about her pending date. Jacques is super smart, well connected, handsome, and a great lover according to the first hand experience of her best friend Kat.

Jacques is the primary leader of a corporate initiative that Kat and Tif are working on. Currently they are in London, home country of Jacques. During the workday Kat and Tif got separated working on different things and Jacques took the opportunity to approach her and ask her out. He mentioned opportunities that he wanted to discuss and that he did not want Kat to come along.

This makes Tif wonder. Her mentor has taught her to think ahead and to consider all possible outcomes, prepare for the worst, but work toward the best. Tif considers the worst possible outcome, that he just wants me alone to probe me for information about Kat and our friendship or our relationship with Richard. That wouldn’t be that awful. Just disappointing.

She ponders the other more favorable opportunities as she cleans her body, her pussy and her ass. ‘One can never be too prepared’, she thinks.

Tif makes sure to be in the lobby by a quarter to 7. She wants to be early. What she knows about Jacques is that he is a busy man and would not appreciate her being fashionably late. To his reputation, as soon as she walks into the lobby she spots him across the way. He is talking to Phillip, the concierge and a recent lover for Tif.

Tif stands tall and proud and walks up to them, “Hello boys. Nice evening isn’t it?”

Phillip leans down and hugs Tif and gently kisses her on the cheek. Jacques patiently waits and does the same. He comments, “You look very nice tonight. Let’s head out. We have a lot to get to. Phillip, it’s always nice talking to you. We’ll catch up again soon.”

They exit the hotel and get into a sedan with a driver. Jacques comments, “I have access to the company car most of the time as part of the business I do. It has its perks.”

They drive for 30 minutes and talk about business. Tif is fascinated by the breadth of knowledge and influence he has across all the major functions of the company. Just as it starts to come back around to Tif, the car stops. Jacques climbs out and helps Tif out like a gentleman.

Jacques peaks his head back in the car, “I’ll let you know when we need you again. Should be a while.”

Tif looks around and comments, “Uh. Is there a restaurant hidden around here somewhere?”

Jacques laughs and says, “Follow me.”

They walk through a few corridors, through a courtyard, into the main building, and to the elevator. As the elevator rises to the top floor, Jacques comments, “I am going to cook you dinner tonight in my flat. I hope you don’t mind.”

Tif starts adjusting her scenarios quickly. When they walk into the flat, Tif is delighted. It is very open with only a few posts to break up the view. It is like a studio apartment but much nicer, with a nicer view.

Jacques breaks Tif’s gaze with a glass of wine. “It is a nice place. It took me a long time to find it and a long time to decorate it. It is a shame that I am not here more often. In that glass is a nice 10 year old red chardonnay. It is not too hefty in case you do not like wine.”

Tif tells him thank you and tries the wine. It is sweet and has a crisp fruity finish. He leads her over to the sitting area. She hears some soft jazz in the background. It is quite the scene.

“Do you know why I asked you to dinner?”

Tif plays coy, “I have a few ideas. It could be one. It could be all of them.”

“Tell me what those are and I will tell you how close you are.”

“You appreciate brevity and bluntness, as you have already said.”

Jacques shakes his head in agreement as he sits his drink down and gets comfortable.

Tif continues, “You said there are some work opportunities that you want to discuss with me.”

Jacques replies, “Yes. I would like to talk to you about a potential future scenario with you. You might think it odd that I did not want Kat here as well as the opportunity has a part for her too. But I want your opinion on a few things without her presence being an influence. What else?”

Tif nods and continues, “I thought you might want to probe me for information about Kat and/or our friendship.”

Jacques laughs, “I am fascinated by your friendship, or what I know of it anyhow, but I do canlı bahis not need to probe you for information about that. What I need or want to know I already do or I will find out over the course of our future interactions.”

“You keep saying you know things about our friendship but I don’t know how you know. Unless Richard told you specific things.”

“Richard did not tell me very many specific things. As I mentioned before, he told me what kind of people you are, specifically characteristics about you. What I am very good at is translating that into specifics about you, your friendships, your work, etc.”

Tif looks a little confused. She says, “Intellectually I understand what you are saying. But I am not seeing how you would extrapolate that into specifics.”

Jacques replies, “Follow this line of thinking. Richard told me that you two were nearly inseparable. He also told me that you two were very competitive, that you were winners. That leads me to believe a few things: one, you to get along extremely well so I am to extrapolate that you are more interested in winning as a team than you are as individuals. I can extrapolate that you two would kill to help the other person be successful because you view each person’s individual success as a success for the team. It is like you two have stopped thinking about competing with each other because you realize that you will be far more successful together.”

Tif looks a little stunned. Jacques continues, “I can also lead on to expand that into your sex lives. I am confident that you two are lovers, that you have shared lovers, and that there is practically zero jealously between you two. How am I doing?”

Tif takes a moment to respond. She finally says, “You are spot on. I followed your logic, but it did not seem as natural for me to make those connections.”

Jacques smiles and says, “I have practiced it for a long time. I will teach you and Kat how to do it and you can practice it. It is very valuable in business and in life.”

There is a break in the conversation as he refills their glasses. He sits back down and asks Tif, “So why do you think I am interested in having dinner here at my home instead of out in a restaurant?”

Tif laughs and says, “Because you love to cook?”

Jacques smiles and says, “Yes. I do. But that is not the reason. I am confident that you know that Kat and I had really great sex the other day. Correct?”

Tif nods her head in agreement. Jacques continues, “I have two motivations. One, I expect that the three of us are going to be good friends and important work colleagues. I want to talk to you about your role and your opinions on things apart from Kat. I want to get to know you individually as opposed to Kat’s best friend. I want to make sure you are not left out of anything you deserve. And by the way, I am going to talk to Kat about this too and be completely transparent. I am not looking to do anything behind her back. I am sure you are going to tell her as well.”

Tif nods in agreement. Jacques continues, “Secondly, you are sexy as hell and I want to fuck you.”

Tif smiles and takes a sip of wine. As she sits her glass down, she comments, “I am on board with both of those motivations.”

Jacques replies, “Excellent. Why don’t you join me in the kitchen so I can get dinner started.”

They move themselves to the kitchen. Jacques starts working on seasoning and preparing the main course. Tif sits on a kitchen barstool and moves the conversation along. They flirt and talk about sexual preferences.

Jacques puts the dish in the oven and sits his mitts aside. He walks around the counter to Tif and crowds her space. He leans in and kisses her gently. The kiss breaks and there is a slight pause before they resume more heavily. After a few moments, there is a break where Tif pushes Jacques back a little. She stands and they resume kissing briefly.

Tif reaches down and undoes Jacques belt and the clasp on his slacks. They fall to the floor. In between kisses they both lose their clothes. As they stand there naked, Tif kisses him one more time and then falls to her knees and sees his uncut manhood poking back at her eye level.

Tif reaches out and wraps her hand around his swollen cock and jerks him gently. He is almost completely shaved. She pushes his foreskin back and engulfs half of his cock in one motion.

Tif wants to make him feel good so she works him over well, pulling him in deep down her throat and massaging his balls. He moans and runs his hands through her hair. This continues for several minutes until Jacques realizes that he needs to get back to preparing dinner.

Jacques grips Tif’s hair more firmly and starts fucking her mouth with more vigor. She moans at him taking control. He feels his balls swell and his orgasm building. He starts pushing himself deeper into her throat and grunting. “Oh yeah. Here it comes.”

Tif readies herself as Jacques starts firing. The first shot is huge and fills her mouth. She quickly swallows as he grunts again. bahis siteleri His cock pulses filling her mouth again. She swallows quickly. Jacques moans as the rest of his orgasm slides down her throat. There is a brief pause as Tif gently sucks the remaining dribbles off of his softening tool before finally letting it fall from her mouth. She looks up and sees him smiling back at her and says, “That was amazing. I am sorry to dump and run, but I need to attend to dinner.”

Jacques helps her off of the floor and back to her barstool. He goes back to the counter and resumes working on dinner. They continue to flirt and talk dirty for the next several minutes as he finishes preparing the main course. She gazes at his sexy body as he works. Once he puts the entree in the oven, he washes his hands and turns to look at Tif. She gazes back at him and comments, “How much time do we have?”

He replies, “Enough for what I want to do.”

Tif smiles as he walks around the counter and approaches her. He leans and kisses her hard and squeezes her left breast. His tongue darts and dances with hers. He flicks her nipple with his fingers sending a charge through her body. She moans and her pussy starts tingling again.

They continue to kiss as Jacques hands work over Tif’s tits. This drives Tif wild and her pussy starts really aching. He breaks the kiss and starts nibbling down her neck. Soon he makes it to her nipples and pulls one into his mouth. Tif starts moaning and running her hands through his hair pulling him in harder.

Jacques pulls in her long nipple and rapidly flicks it with his tongue. Tif’s moans get louder and she leans back and arches her back giving him full access to her chest. He moves a hand down and slides it over her bald pussy.

Jacques methodically massages her pussy stopping on her clit every few passes. It is not long before Tif is practically panting. Jacques moves to the other nipple and applies even more pressure. He slides his middle finger gently into Tif’s tight box. Tif groans, “ohhhh yessss.”

Jacques slides a second finger into her hungry pussy. Tif’s moans become inaudible and she soon starts to buck her hips. Jacques pulls off of her nipple and increases the pace of his fingers. He leans in and kisses Tif hard again. She sucks his tongue in like it’s a dick.

Tif breaks the kiss and leans even father back and starts moaning loudly. Her pussy starts leaking all over Jacque’s hand and the barstool as she starts humping his fingers. He changes the angle a slight bit and increases the pace even more. She feels a huge orgasm building and knows it is going to explode like a bomb when it hits. He knows he is going to fuck her, but he wants to make her beg for it.

Jacques brings her up to the edge when he leans in and asks, “Are you going to cum all over my hand Tiffany? Are you going to soak my hand with your sweet pussy juices?”

All Tif can muster is an ‘ughhhhg’.

Jacques starts furiously finger fucking her. Tif holds her breath and arches her back even more. When it hits her, she almost screams as she exhales all the air inside of her. Her body shakes and her pussy explodes soaking Jacques arm, his lower body and the floor.

He slows down and pulls his fingers from her dripping pussy and brings them to his mouth and sucks off her juices. He looks down at her as she tries to catch her breathe when his timer goes ‘ding’.

Jacques comments, “You have a sweet little pussy Tif. I look forward to tasting it again later.”

Jacques walks back into the kitchen leaving Tif to recover. He moves about the kitchen doing this and that continuing to prepare dinner. He puts a couple more things in the oven and then makes his way back over to Tif.

“Have you recovered yet?” he asks.

Tif smiles and says, “I think so. That was really good.”

“I am glad you are recovered because we have a few more minutes.”

Jacques reaches under her arms and picks her up and lays her on the counter. It is cold and sends a shock through Tif’s naked body. Before she can react, Jacques pulls her legs up in the air and starts kissing the sensitive insides of her thighs, inches from her still swollen pussy.

Jacques wastes no time running his tongue up the length of her tiny slit. He licks his lips and says, “Tasty”. He repeats this process multiple times enjoying the tender little folds of her juicy pussy before finally settling in on her little pink bud. He clamps down on her clit flicking it rapidly with his tongue. Tif moans loudly and squeezes her erect nipples.

Jacques sucks and slurps and tongues her clit for a few minutes bringing Tif to a body shaking orgasm. Jacques cleans up the extra juices flowing out of her pulsing gash and stands up just as his timer goes ‘ding’.

Tif lies there for a moment needing to recover again. Jacques goes about tending to dinner. After a few minutes Tif rolls off of the counter and stands up. She looks at Jacques naked body standing across the kitchen working on something on the counter. She saunters over bahis şirketleri and hugs him from behind and comments, “Can we skip dinner so you can fuck me? Or can I help you with dinner so we can get to it?”

Jacques laughs and replies, “Patience young lady. We have a little work yet to do for dinner and you need your strength. Why don’t you take over here and finish prepping this salad.”

Jacques moves aside and starts tending to what he has in the oven and Tif takes over cutting ingredients for the salad. A few minutes later Tif comments, “I think I am about done here.”

Jacques closes the oven and walks over behind Tif and hugs her from behind. He kisses her neck several times while reaching around to squeeze her handful of breasts. Tif feels him wedge his cock in between her ass cheeks. He comments, “Is that what you want Tif? Do you want me to fuck your tight little pussy right now?”

Tif reaches around and pulls his head in closer and says, “Very much so. I am ready to feel your stiff cock inside me.”

“Let me see how ready you are”, Jacques says as he reaches down and rubs her wet pussy. “Very wet still. Maybe you are ready.”

Jacques backs up pulling Tif with him. A small nudge causes her to bend over making it easier for him to move in. He bends his knees a little and aims the head of his erect cock at her tiny entrance. He moves the head of his cock around her hole and across her clit several times, teasing her. “You want this Tif?”

“Yeeeesss. Please. Fuck me now.”

The stimulation was driving her nuts. She is on the verge of another orgasm with all this teasing. She moves her hips a little and shoves back causing his cock to penetrate her. With the seal broken, Tif moans and Jacques takes back control. He pushes his cock in deeper before pulling it back out and pushing it back in. Several rounds of this occur before Jacques is fully buried inside his tiny date.

Once completely in, he pulls almost all the way out and slams back into her, driving his cock balls deep into her cunt. He lets it sit there for a moment before repeating this process.

“Oh fuck yes!”

Tif’s orgasm approaches quickly as his hard cock hits all of the right spots. Her legs shake and her pussy pulses around the unit pounding in and out of her. She groans and heartily says, “Yes. Fuck. Oh yes. Right there.”

Tif grips onto the counter and braces herself as Jacques starts pounding her faster and harder. Her head begins to spin as multiple orgasms surge through her body. Jacques grunts and slams in one more time before his cock explodes inside Tif’s hot box. Together they share a long orgasm that leaves each gasping for air.

Still breathing heavy Jacques pulls his half limp cock out of her causing pussy juice and cum to start leaking down her leg. Tif uses her finger to catch it and brings it to her mouth. She smiles at Jacques as she does it again. She comments, “I can’t let this good stuff get away.”

Jacques smiles and watches Tif do her work. When she finishes, she drops to her knees and cleans up his messy unit. As she finishes cleaning his balls, the timer goes ‘ding’.

They break. Jacques quickly brings the food to the table while Tif refills their wine glasses. They sit down to eat dinner and Jacques comments, “Have you ever eaten dinner naked before?”

Tif thinks for a moment and says, “I think I have, but it was not as nice as this or with such good company.”

Jacques smiles at her compliment and continues, “So tell me. Rank these in order of preference. Oral, anal, or regular sex?”

Tif replies, “What makes you think I have ever done anal or like it at all?”

“Remember how I told you that I put things that I know together and then make educated assumptions on the others?”

Tif nods her head in agreement.

“Well that is what I did here. I deduct that you are willing to do anal. I am trying to gauge where it fits in your pecking order.”

“I see. Well I like all three a lot. I guess it depends on the day or the person which of those I may prefer at any given moment.”

“You are a very sexy woman and to know that you are truly a full service girl, you are an amazing catch. I look forward to working with you and Kat in the future.”

“I hope that includes fucking us in the future too,” Tif says with a laugh.

“Of course. Of course.”

The topic moves over to career interests and opportunities as they finish dinner and clean up the dishes and the kitchen. Soon after Jacques suggests they move back to the seating area.

Jacques sits in his favorite chair and barely gets settled before Tif climbs in the chair on top of him. She leans in and kisses him passionately. When the kiss breaks Tif comments, “I appreciate you talking to me about me and my career and opportunities you see for Kat and I. But to be honest, we’ll have to continue that conversation later. Because right now, I need more of your stiff cock inside me.”

Jacques reaches around and grabs her ass as Tif grinds her wet pussy all over his growing manhood. He leans in and starts sucking a nipple bringing a moan out of Tif. Within a couple minutes, Tif reaches down and maneuvers his erection inside her hungry cunt. As she lowers herself down, she moans deeply.

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