Multiple Creampies

Story one: Multiple Creampies -- Teenage Girl Assists in Her Best Friends Training

This is the first independent story of our teenage whore Tiffany "Tif". This story accompanies the Katherine "Kat" storyline. The timing of this event is mere hours before chapter 6 starts in that storyline. 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 hoped it would come. Kat told her that she was going to ask Richard if she could come to her next lesson. Kat is her best friend and a recently admitted cum addict. Tif has always been a whore, but the nature of their friendship changed in a very good way a few weeks ago when Kat realized what she is. Richard is an older man that Kat has recently met. He is going to teach her strategies on how to meet her 'needs' more safely and more often. Tif is excited to help her bestie in any way she can.

Richard called and interviewed Tif. He thoroughly investigated the degree of her and Kat's friendship. Tif told him that she is best friends with Kat and would do anything for her. Then he told her to meet him at a hotel a few hours before Kat's lesson was to start. And lastly, he said keep it quiet. Only tell Kat that Richard said she could be there and nothing more.

It has been a rough week for Tif. It is very hard for her to keep things from her best friend. So instead of lying, she chose to avoid her. Now it is finally Saturday morning. Tif goes for a run, like she does every Saturday morning in the offseason. Tif is a cheerleader, but there is not much to do in the early spring except stay in shape. So Tif works out 3 times a week, runs twice a week, and swims for the high school team. At 5'6", blonde, and slim, she keeps herself in excellent shape. She has strong legs and an excellent, firm ass. Her tits are only a B cup, but her nipples are long and sensitive.

Tif gets in the shower after her run and goes through her usual shower ritual. She shaves her legs, shaves her pussy completely bald, and gives herself an enema. She absolutely loves anal and a whore can never be too prepared.

Tif drives to the hotel as instructed at the time she was told. She gets into the elevator and heads to the top floor suite. She takes a deep breath and rings the doorbell to the room. A handsome man that fits the description of Richard answers the door.

With a tight hug, Richard says, "You must be Tif. I am so happy to meet you. Please come in and sit down."

As Tif enters the suite, she sees that it has a large bedroom and a large sitting area. She takes a seat on the couch. Richard sits in the chair across from her. For a moment, they size up each other without talking.

Richard begins, "I asked you to join me here so early for a couple reasons. First, I would like to get started by bringing you up to speed on what I have planned for Kat and discuss what role you can or are interested in playing in her development and ultimately in her life as it might be."

Tif nods her head okay.

Richard then says, "Some rules of engagement. First, I am a very forward and blunt person. It saves time and removes confusion. Second, I am a very trustworthy person. I know you don't know me and will need time to come to believe that, but I want to start you on the right foot. I have Kat's best interests first and foremost. And by your connection to her, I will have your best interests first and foremost as well. I ask you to be honest and to be forthcoming. I don't want any surprises."

Tif nods her head again.

Richard continues with more personal questions like, "I want to hear about your sex life. How often do you have sex? How many partners do you have sex with? Do you like women? Etc, etc."

Tif pauses before she answers and determines that she needs to be completely honest or she will be on the outs and Kat will be on her own. That is the last thing she wants.

Tif takes a deep breathe and replies, "In a sentence, I'm a whore. I don't like the word whore, but it describes me. I need to have sex a lot. I get cranky if I go without for any length of time. Sometimes I go for new people, but mostly I have regulars I go to. Let's see, what else? Oh, you asked me what I like. I like to do anything sexual with men or women. I really love anal sex. At the risk of ruining what might be the start of a great relationship with you, I would fuck you right now if you wanted to."

Richard smiles and comments, "Good to know. Based on our conversation, I think I can trust you. Can I trust you Tif?"

Tif replies immediately, "Yes. Richard. I want to be a part of this. I love Kat. I plan to be her best friend for as long as she'll have me."

Richard nods in acceptance and continues; "I think you will provide great assistance for me in Kat's training. You said you would be willing to do anything to support Kat in her training right?"

Tif shakes her head and says, "Yes. Absolutely."

Richard continues, "We will have to work out some specifics, but let's proceed forward with the assumption you are all in." Then he takes out his phone and types for a few minutes.

Richard then spends the next 30 minutes laying out his vision for Kat and a high level his plan to get there. He talks about the need for things to happen in order without pollution. He asks Tif not to divulge anything to Kat unless they talk about it ahead of time.

Richard continues, "I won't ask you to lie to Kat. But I may tell you more things than I tell her in the short term so that you can support the process. And if you spill it to her, it will not have the same effect."

Richard continues by telling Tif what her role can be and gauges what her interest is. They work out the logistics and the specifics with examples.

Richard pauses and then continues, "We agreed that you are willing to do anything for Kat. I want your role to be a supporting actor for her. In the short term, it might be as a companion to help her get what she needs to meet her growing addiction. You might have to schedule meet ups for her. You might have to help run interference with her family. Stuff like that. In the long term, you need to be one of a few people in her inner circle, continuing to do this on a larger level. You will be the one she trusts. I believe you can be this person for Kat. She trusts you and will need someone like you."

Then, there is a knock at the door. Richard doesn't move. A very sexy older woman walks out of the bedroom and answers the door.

Richard asks, "Do you trust Kat?" Tif nods yes. "Then through her, will you trust me?" Tif nods yes.

Richard continues, "I want you to know that this is a safe environment. And that I will not ask you to do anything you do not want to do. But I think you are going to enjoy what I have planned for you today."

Then the sexy woman leads 3 young guys into the sitting area. Richard gets up and holds his hand out to Tif. He helps her off of the couch.

Richard then says, "Tif, I would like you to meet some associates of mine. They are here to fuck your brains out. In addition to the satisfaction you will get, I want your tight little pussy to be full of cum when Kat gets here. It's part of her next lesson."

Tif is slightly shocked at this turn of events, but then recognizes that her pussy just drooled down her leg. The first guy comes over and leans down and kisses Tif passionately. His tongue gently darts in her mouth. He reaches down and pulls Tif's skirt up and grabs her bare ass. When he picks her up off the floor, Tif wraps her legs around her new suitor. They break their kiss in time for Tif to see the other two guys have come up next to them. The second guy leans in and starts to kiss Tif a little harder than the first. The third guy reaches under Tif's skirt and starts rubbing her pussy through her thong. Tif breaks the second kiss so she can moan. This lasts a few moments before the first guy takes her over to the couch and lies her down. He starts taking off her clothes. The two guys behind him start taking their clothes off as well.

With her clothes off, the first guy spreads Tif legs high into the air and brings his mouth to her now sopping wet pussy. He immediately starts attacking her clit. Then he shoves two fingers deep inside of her and starts rhythmically finger fucking her. The second guy is now naked and he brings his hard cock over to Tif and pops it into her open mouth. The third guy comes over and starts pinching and sucking on Tif's long hard nipples. Tif is building an orgasm is quickly with a mouth on her pussy, a mouth on her nipples, and a cock in her mouth.

The first guy pushes Tif's legs even higher, so that her ankles are right next to her ears. Good thing being a cheerleader requires her to be so flexible. Then he moves down to her puckered star. He dives in with his tongue first and then a finger. The second guy pulls his dick out of Tif's mouth and moves his mouth down to her pussy. He starts flicking her clit with his tongue and then inserts two fingers deep inside. The third guy comes over and slides his cock into Tif's vacant mouth. He keeps pushing deeper and deeper until he is all the way in. He holds it there for a few seconds and then pulls it all the way out allowing Tif to gasp for breath. Then he repeats this over and over. The first guy inserts a second finger into Tif's ass and really starts to work them in an out. Guy number 2 starts adding more intensity to his finger banging of Tif's pussy. The third guy pulls his dick out of her mouth just in time for Tif to moan through a powerful orgasm. Her pussy and ass both clinch down on the invading fingers.

Then all 3 guys back off of Tif for a moment. As Tif shakes off the remaining effects of her orgasm, Richard approaches.

He asks her, "Do you want to keep going? You said that you love anal sex. I want them to fuck you in your ass and then cum in your pussy. Remember, this is important to Kat's lesson later today. Is this something you are willing to do?"

Still panting a little from her intense orgasm Tif replies, "Hell yes. Fuck me. Fuck my ass. Cum inside my pussy. I am yours to do whatever you wish."

Richard continues, "One after each other they will do this until they can't go anymore or we run out of time. Remember, I want that pussy to stay tight and able to hold onto what we are going to give you. Then you are to hold all of this cum in your pussy until Kat gets here. It is part of her next lesson. Are you okay with that?"

Tif replies, "Yes of course. All of you can fuck my tight ass. Since I am an anal loving whore, I always prepare myself just in case. And I can't wait to feel you shoot your loads in my pussy."

With that, Richard gets undressed and sits down on the end of the couch. He starts stroking himself and is almost instantly fully erect. Tif watches Richard stroke himself and her eyes pop when she sees that he has a huge dick that is at least 10 inches long. She notices that he also has huge balls. Richard indicates for Tif to come over. She smiles and then joins him on the couch. He pulls her down to his cock and she happily starts to go to work on it.

Tif feels a cold, slimy substance she assumes is lube being dropped on her ass. One of the guys, Tif is not sure which one, pushes two fingers deep into her ass. He rhythmically moves them in and out and soon adds a third. Tif moans between trips up and down Richard's hard-on.

After a few minutes, the guy banging her ass pulls his fingers out and positions his cock at the entrance of her back door. He slowly puts pressure on it until his head pops through. Tif stops sucking Richard's cock and moans louder. Then he starts slowly working his dick in and out of her tight ass pushing more and more of it in each rotation. Out of the corner of her eye, Tif sees the beautiful woman sucking the dicks of both of the other guys. She is not stroking them, but only sucking one then the other. The realization that she's a fluffer comes to Tif's mind briefly before she goes back to sucking Richard's dick.

Over the next few minutes, the guy behind her works his dick in and out until he is able to get balls deep into Tif's ass. Now fully in, he slowly moves all the way out and pushes back in again. Over and over again he does this listening to Tif's muffled moans get louder and louder. Tif has been focused on getting more and more of Richard's dick in her mouth and down her throat. She is not sure she can deep-throat suck a huge dick, but she is determined to try.

After several minutes of slowly working Tif's ass, the guy behind her pulls all the way out and steps away. Tif groans at the backdoor emptiness she feels. But he is quickly replaced with another. This guy is a little thicker than the one before and it takes some time for Tif's ass to accommodate his entire length. Tif's pussy is draining juice down her leg so she reaches down with her free hand and starts to masturbate. Within a few minutes, Tif is shaking with her second orgasm. Her ass clinches her invader and she moans on Richard's dick.

Following Tif's orgasm, the second guy pulls out of her ass and is replaced by the third guy. He is longer then either of the two before him. He slides in easily, but takes some time to make his depth. Once he is in, TIf increases her attention on Richard's dick. She is determined to show her appreciation to him for the fucking she is getting right now. She stops masturbating her pussy and puts both hands on Richard's dick and starts stroking. She matches the stroking rhythm with her mouth and goes deep on Richard's manhood. She is diligently trying to make him cum, but Richard is holding out with his amazing stamina.

The guy behind Tif starts fucking her ass harder and faster. Just before he is ready to cum, he pulls out and calmly slides his cock about 2 inches into Tif's pussy. She completely stops sucking Richard's dick and looks back to see the guy bust. The guy leans his head back and has a glorious expression of pleasure on his face as he lets loose a torrent of cum inside Tif's tight pussy. She can feel his cock pulse as shot after shot hits the back wall of her pussy. Tif's clenches her pussy on his dick and milks it for every drop it has. The man leaves his dick in her pussy until it goes limp and then he very carefully removes it. He walks over to the beautiful woman and she uses her mouth to clean him up. This time she starts stroking his cock with the intention of getting it hard again.

Tif continues her onslaught on Richard's dick. Guy number two comes over and slowly slides his cock back into Tif's ass. He goes balls deep almost immediately, much to Tif's delight. She almost has an orgasm when he hits bottom. Tif sucks Richard deep and hard and fast. Richard moans, but still won't cum. The man behind her puts his hands on her hips and starts pounding her ass hard. Tif feels an orgasm building. Not long after, the man pulls his cock out of Tif's ass and slides it into her pussy and starts emptying his balls. Tif loves the feel of his cock pulsing with every shot. It causes her to go over the top and have her own orgasm. Her pussy squeezes the guy's cock tight. With all the pressure of the orgasms, nothing escapes out of her pussy. The man slides out after becoming limp. He walks over to the beautiful woman so she can clean him up. The first guy is erect again.

Tif tries to go back to Richard's dick again, but guy number three slides his cock back in her ass. It is not long before he is grabbing her hips and banging her ass with reckless abandon. He soon pulls out and pushes his cock into her pussy as well and unloads a huge amount of cum. Tif can feel his dick pulse again and again as the cum pours out into her young pussy and adds to the other two loads that have already been deposited by his friends. Tif sits and enjoys the bliss of the man's orgasm inside her pussy until he pulls his limp dick out slowly.

The pace quickens, The third guy is quickly replaced with one of the other two. He quickly fucks her ass hard and dumps another load in her pussy. Another guy replaces him. He fucks her ass again and cums in her pussy as well. With this revolving door, Tif's ass is wide open. The guys are sliding right in down to their balls immediately. Tif tries to clinch their cocks to invoke their orgasms. One after another they rotate, dropping whatever cum they have left in her pussy. Tif has given up sucking Richard by now.

When it looks like the other guys are spent, Richard gets up and tells Tif not to move. After a brief moment of silence, she hears the lube bottle and then a moment later, feels Richard press his cock against her ass. He pushes his head into her dark tunnel. Even though Tif has been fucked a dozen times in a row in her ass. There is still a 'pop' when Richard's head pushes through. He pushes his cock deeper and deeper into Tif's ass until finally he is all the way in. Tif feels fuller than she ever has. This is the biggest cock she has ever taken anywhere, let alone her ass.

Richard goes all the way in and pauses and then slowly pulls back out. Then pushes back in and repeats the process. Every time he pushes in and out, it rocks Tif slightly. She can feel the liquid in her full pussy slosh with every rock. Richard speeds up his pump until finally he pulls out. Tif feels him put just a couple inches of his cock inside her pussy. Then she feels his cock spasm as he unloads his jizz inside. She is in blissful heaven. Blast after blast hits shoots inside until she feels her pussy overflowing. The extra cum starts to slide down Richard's balls.

He waits a moment for his dick to go limp and then pulls his cock out slowly and tells Tif not to move. Then he slides around and puts his cock back in Tif's mouth. She starts to clean him up, enjoying the scent of herself and the taste of his cum. 'How juicy' she thinks. She works his dick with special attention trying to coax any remaining cum drops out of his dick. Richard puts his hands on the back of Tif's head and starts fucking her mouth. He starts going deeper and deeper and faster and faster. And then unexpectedly he unloads another load of cum deep into Tif's throat. Tif starts swallowing as soon as she feels it. He keeps sliding in and out of her mouth, but comes out a little more with each pulse. Soon, Richard is almost all the way out and he is still unloading cum. Finally, Richard pulls his cock out of her mouth and lays it on Tif's tongue where she cleans up the last little bit of cum off of Richard's slit.

Richard smiles down at Tif and says, "What a performance. You are almost ready. Honey, can you come over here please and help Tif out?"

The beautiful "fluffer" comes over while Richard and the guys step away.

She looks down at Tif and says, "Hon, I am going to get you staged okay? But I need you to make sure you clench that pussy of yours as tight as you can. Got it?"

Tif shakes her head. The woman moves behind Tif and starts using her tongue to clean up the cum that had escaped out of her pussy when Richard busted. She licks all the way up her leg. Then up the other leg and all along the outside of Tif's pussy. Then she cleans up Tif's sore asshole.

The hot older chick says, "You are one hell of a trooper Tif. I would like to spend some time with you sometime and get to experience you more fully."

Tif smiles and responds, "I think I'd like that."

Richard comes in and says, "Kat will be here any minute. Let's get her ready."

Richard looks down at Tif and smiles. Then he looks into her eyes and says, "You are wonderful. On any given day, where I am not trying to stage something for Kat, I would have cum in your mouth earlier. I know you gave it a heck of a try. And even with my stamina, I was almost not able to hold out. That is why I came back and gave your mouth another round. I would like to spend some more time with you soon. After you heal up of course."