While Kat's Away, Tif Will Play Pt. 02

This is the fifth independent story of our teenage whore Tiffany "Tif". This story accompanies the Katherine "Kat" storyline. The timing of this event aligns with module one, chapter ten, while Kat is in Hawaii with her family. 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.

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The next morning Nicole wakes up when she feels Michelle stroking her breast. Nicole turns into her and they lightly kiss. Nicole says, "Looks like you have come around."

Michelle responds, "A little. I am still scared shitless that this is going to get out and my dad or my boyfriend will find out."

Nicole responds, "Your secret is safe with us 3 girls. What happens here stays here, unless you don't want it to. Personally, I think I am changed forever. I think I am going to continue to have side flings with other girls, especially Tif, if she'll have me."

Michelle says, "I don't know what I will do once we leave here. But I think I want to have more fun while I am here. Can we go again?"

Nicole leans in and kisses Michelle again. She turns her over and quickly ends up between her legs. She does all the things that Tif taught her and that she would want done to her. Michelle enjoyed them because after a few minutes, she shook and filled Nicole's mouth with nectar.

As Nicole works her way back up to Michelle's big tits, a voice from the other bed says, "What do we have here?"

The girls look up and see Callie sitting up watching them. Michelle gets nervous. Tif says, "Callie, Michelle had a low key experience last night with us girls and it looks like she wanted an encore this morning. Nice job by the way Nicole."

Nicole blushes and says, "Thanks Tif. I just took your advice."

Callie says, "Well. Welcome to the fold Michelle. It will make the next few days much more fun."

Michelle responds, "Uh. One problem. I have only been on the receiving end. Can one of you help me with the giving part? I want to try it."

Nicole says, "I want to receive. Tif can you teach Michelle how to do it on me?"

The girls all look at each other and Tif shakes her head. She looks at Callie and says, "Are you okay with that?"

Callie says, "Yeah. My pussy needs a break after last night and you are a much better teacher than I am."

The girls get in their positions and Tif teaches and allows Michelle to work on Nicole. Michelle took to it quickly and really enjoyed giving Nicole two orgasms. When they are done, Nicole kisses Michelle and tells her it is a nice finish to kiss the girl that just gave you orgasms as a show of appreciation. Tif smiles.

The girls get dressed and head to breakfast. Michelle comments that she is surprised that her dad and Jack are not down yet. "They must have had a late night," she says. Tif hides her smile behind her napkin. Callie notices.

When they are headed to the beach, Callie sneaks over to Tif and says, "You fucked Brett and Jack last night didn't you?"

Tif smiles and says, "You can't tell the others."

Callie says, "Fine. But you have to give me the details."

Tif says, "Well. What you said about Jack was true. He had not been with a woman for a while. So I gave him first dibs and special treatment. In fact, I made Brett wait through 3 rounds with Jack. I think that made him angry and he pounded my throat, my pussy, and my ass."

Callie responds shocked, "Whaaaat? So not only did you fuck both of them, but you gave them anal? And Brett has enough staying power to service all three for you?

Tif laughs, "Well. Brett is the only one that got anal. It was part of the peace offering I gave him for waiting. And he is really weird. He came in my mouth once, my pussy twice, and my ass twice in like 30 minutes."

Callie says, "Wow. You better not do it again without me."

Tif says, "Really? I don't know if Brett is always that aggressive, but damn. He fucked me as hard as he could."

Callie sighs, "I can only imagine. I want to get fucked as hard as he can. Take me with you next time. Maybe if I taunt Brett he will do me hard like he did you."

Tif just shakes her head in disbelief, "Sure. I'll let you know."

The rest of day goes by quickly. The girls spend time on the beach flirting with guys and some girls. Every couple of hours, a different pairing of the girls would sneak off to the room to go down on each other and share orgasms. At dinner that night, Michelle and Nicole were so enamored with each other that they did not realize that the guys were flirting non-stop with Callie and Tif. As they all left, Tif pulls Brett aside and says that she wants another go tonight and that she is bringing Callie. He agrees.

The late evening included a couple hours of lesbian lovemaking. Nicole and Michelle quickly become more comfortable and are ready to branch out. Michelle lied on her back for more than hour while the girls rotated, one eating her pussy and another riding her face. Michelle's abdominal muscles ached from cumming so much and her face was caked with dried lady juice. Tif introduced some light anal play to Nicole who seemed to like it. Tif and Callie took it easy on each other knowing they still had men to please later that night.

Finally, the girls tap out and crash. Nicole and Michelle are unconscious quickly. Callie and Tif quietly sneak out enter the guy's room just after midnight. Jack seems hesitant again until Tif reminds him how much fun he had last night and that tonight should be twice as much fun. Brett is happy because he assumes he doesn't have to wait tonight. Callie teases him, "Just because I don't make you wait, doesn't mean that I don't want you to fuck me hard. Understand?"

Brett replies, "You don't have to worry about that."

Callie says, "Well boys, we are already hot and ready. Let's see those cocks."

Brett pulls down his boxers and Callie is on her knees servicing him immediately. Jack is still moving slowly. Tif gets undressed and comes over to help him out. She helps him reluctantly pull off his shorts. She eases his hand to her swollen pussy where he starts to move his fingers around. She lowers his head to her breast where he takes hold of it and starts sucking it. She reaches down and starts stroking his member, which rises quickly.

Callie stops sucking Brett and pushes him over onto the bed and tells him that he is going to eat her pussy. He starts to protest, but she crawls on top of him and lowers her pussy onto his mouth and starts grinding. He has not choice but to open his mouth and tongue her young pussy.

Meanwhile, Tif has disengaged Jack from her parts and has moved down to start sucking his erect manhood. She slides up and down slowly to make sure he does not cum too fast this time.

Callie rides Brett's face for a little while before she gets bored. She moves down a bit and hovers over his stiff unit. She asks him if he is ready to feel her warm goodness. As he shakes his head yes, she lowers herself onto him. Her wetness allows him to enter her easily. Within a few strokes her box has completely consumed him.

Tif pushes Jack back and climbs on top of him. She aims his manhood at her love box and lowers herself down. It takes her several minutes to get him completely in. Soon both men are moaning at the young girls grinding on their cocks.

Tif leans down and starts kissing Jack and telling him how good he feels inside of her. She kisses his ear and then asks him, "Would you like to cum inside my tight young pussy Jack?"

When Jack finally responds he says, "I... think... it's ... coming... right now..." And he shoves his hips up sending his hot cum into her pussy. She slowly grinds him milking his manhood for every drop. Tif waits out his orgasm and then slowly pulls off his softening member. She clinches her pussy together and stands up without losing a drop.

By now Callie is lying on her back with her legs in the air getting worked by Brett. Tif hops over and crawls onto Callie's face and says, "I have a surprise for you."

Once in position, Tif pushes hard and two big gobs of cum slide out of her pussy into Callie's waiting mouth. Callie swishes it around and then swallows it down. Then she spends a few seconds cleaning Tif's pussy up.

Tif crawls off of Callie's face and walks over to Jack to check on him. He tells her that he is still a bit out of wack. He says, "I mean, it has never been in my nature to have sex with another guy in the room or to have sex with young women like this."

Tif's responds, "Jack, if you are uncomfortable, we can leave. Otherwise, my advice to you is that this your opportunity to try anything that you have ever thought about. Callie and I are willing partners to do anything you want. After we leave here you can go back to be as conservative as you want to be."

Jack ponders this for a moment and then says, "Anything?"

Tif responds, "Anything."

Jack smiles and says, "Well. There is this one thing I have always wanted to try."

Jack stands up and taps Brett on the shoulder. Brett responds, "What?"

Jack says, "Can join in? Let's double penetrate this girl."

Brett smiles and says, "Okay. But I get her ass."

Tif winks at Callie. Brett steps back and Callie gets off the bed. Jack lies down. Callie crawls on top of Jack, who is hard again just thinking about this. Callie lowers herself down on top of Jack. He is bigger so Callie moans as he fills her up. Brett starts to move forward, but Tif stops him. She says, "Let her become acclimated with his size first. And by the way, do you have any lube?"

Brett laughs, "Why would I have any lube?"

Tif sighs and says, "Okay, Option 2. Brett you wait a minute."

Tif walks over to Callie and pushes her forward completely on top of Jack. She licks her fingers and starts playing with Callie asshole. She massages and gets her relaxed, all the while she is still riding Jack. Soon Tif slides in a finger and as soon as Callie's anal opening relaxes again, she slides in a second. She finger fucks her ass slow at first, but then with more speed. Without intending to, this sends Callie over the top and she clamps down on Jack's member and Tif's fingers as her orgasm pulses through her body.

Finally Tif pulls her fingers out, swabs up her fingers and lathers Callie's ass. Then Tif turns around and drops to her knees. She starts sucking on Brett's cock, getting him nice and hard and lathering up his cock. When she pulls away and stands up she says, "Now you can go."

Brett steps forward and aims his dick head at her wet opening. He pushes in aggressively and pops his head in right away. Callie yelps. He pushes his cock in deep on the first plunge. Callie yelps again. Tif taps him on the shoulder and tells him to slow down. Brett slows down and lets Callie relax to the double penetration. Within a few minutes, both guys are going deep and develop a rhythm. Tif reaches around and starts twisting Callie's nipples. This causes her to shake in another orgasm.

They go like this for a few more minutes until Brett starts pounding Callie's ass hard. Callie starts moaning loudly and Brett grunts. He slams himself into Callie one more time and lets go of his load. Callie feels Brett's cum hit the walls of her rectum. She tightens her ass and the pulsing sends her into her own orgasm. This tightens her pussy, which sends Jack into an orgasm. Callie moans loudly over and over as two men fill her holes with cum.

When Brett's orgasm subsides, he pulls out and Tif gets on her knees and cleans the cum off of his cock. He sits down. Tif leans over and cleans Callie's ass of the cum she can get to. Callie climbs off of Jack and lies on her back. Tif cleans up Jack's cock first and then moves to Callie's gaping pussy. Callie pushes and some cum comes out of her orifices. Tif cleans up and swallows what she can. Then she creeps up and kisses Callie.

They guys lie on their respective beds spent. Callie also lies there spent. Tif looks at the bungled group. Then she suggests they call it a night and reconvene another time. All three shake their head. The girls make it back to their room and back in their bed without notice. Callie looks at Tif and asks, "Why did you let them DP me instead of you? It was your idea?"

Tif responds, "Because I am a giving person. I am always trying to make the other person's experience great. Plus, I had them last night."

Callie says, "I am glad we have added this to our relationship Tif. I enjoy you a lot."

Tif says, "Likewise."

The girls go off to sleep. The next couple days go by very quickly. The girls spend most of their time on the beach or in the room in various lesbian positions. Now that Michelle is okay with her decision, she has been gung ho on participation. Callie was even able to get her to enjoy fingers in her ass. Nicole has become an oral queen who loves the taste of her friends orgasms in her mouth.

The next two days prove even more interesting for Callie and Tif as they found themselves in the guys room almost as often as their own. The girls took turns going to the room with only one guy at a time during the day and usually fucked both of them at night. Callie, especially, made sure to keep their balls empty. Jack is very much coming out of his shell.

They reach Friday night toward the end of their week. Tif independently reminded each person that they need to keep their recent trysts under wraps at group events like dinner. Dinner still included a lit of flirting. After dinner, Brett pulls Tif aside and asks if the girls are coming to their room later that night. Tif replies, "I am getting worn down Brett. The late nights are taking their effect."

Brett smiles and says, "Are you telling me that an old guy like myself is outdistancing you?"

Tif stops herself from telling him that she is also spending half of her day fucking his daughter and the other girls. But instead she says, "I guess we are only here for a couple more days. We'll be there."

The girls go back to the room for their usual ritual of lovemaking. When Nicole and Michelle fall asleep, Tif drags Callie out of bed and down the hall to the guy's room. They guys spend the next 2 hours fucking them in every position and in every hole. Jack was good for 3 orgasms and Brett easily had 10.

The girls finally make it back to their room around 3 am. When Nicole and Michelle get up, they leave without waking Callie or Tif. Callie gets up an hour later and leaves. Tif wakes up late morning realizing that she is alone, finally.

Tif gets some fruit for breakfast downstairs and then decides to enjoy her solitude by going to the hotel pool. She lays out getting some sun for a little while. A couple next to her in the early stages of a disagreement distracts her.

As Tif is entertained by their discussion, she gives them the up and down. He is handsome, maybe mid-forties. He has a good-looking body with a little body fat around the mid section. She is bleached blonde, and has had a lot of work done on her body and face. She looks amazing.

The guy says, "You keep complaining that you are worried about burning, but you don't want me to put any lotion on you."

The woman responds, "It's because every time you do, you stick a finger in my cooch or ass."

The guy responds, "Can you blame me? You're so hot I can't keep my hands off of you."

The woman replies, "I told you we could have sex in a little while. I want to get some sun."

The guy says, "Are you going to let me have that booty later?"

She says, "You know I have never done that. Maybe you need to find someone else to help you with that."

The guy says, "I am going to go get us a drink. Maybe someone up there will be interested in some booty sex."

Tif watches him go and then gets up and steps over to the woman. Tif says, "Excuse me. I could not help but overhear your dilemma. I'd be happy to help you with your lotion needs."

The woman looks up and says, "Oh my. I am so sorry we bothered you. Robert is over the top sexual and sometimes I just need a little lotion on my body you know?"

Tif replies, "I understand. You are incredibly hot though. It is going to take a lot of restraint on my part to put lotion on your body without letting my hands wonder into your cooch or your ass."

The woman laughs and hands her the lotion and says, "I wouldn't mind if you touch me darling. I am sure you have a much gentler touch. By the way, I'm Sophie."

Tif smiles and takes the lotion and says, "I'm Tif. Nice to meet you."

Tif goes about putting lotion on the woman's bare back. As she moves down her back to ass, she notices that the lady has spread her legs and Tif can see the outlines of her pretty star peaking out from her thong. Tif puts a generous amount of lotion on the ladies butt cheeks and starts to rub it in. The woman arches her ass a little. Tif takes the hint and runs her hand inside her legs and up the woman's puss.

As Tif adds pressure, she hears the woman moan 'Mmmm'. Just then Robert returns and asks, "What do we have here?"

Tif quickly removes her hand and stands up away from his wife. Sophie responds, "I found someone that would put some lotion on me dear."

Robert replies, "Yeah? It looks like she was doing it the same way I do, but getting a better response."

Sophie replies, "It's because she was gentle and allowed for some intrigue. You shove your fingers in immediately."

Robert says, "Uh huh. Well miss. I am Robert. I see you have already become acquainted with my wife Sophie."

Tif shakes his hand and introduces herself.

Robert says, "It appears my wife enjoys you. Would you like to have lunch with us so I can get to know you as well?"

Tif agrees. They find a table inside. Chatter quickly turns sexual once more. Robert asks Tif, "Can you provide your thoughts on something for me?"

Tif agrees. Robert continues, "It has been my experience that there is a way to have anal sex with a woman and for her to enjoy it. What is your opinion?"

Tif looks at Sophie and gets no nod from her, so she answers, "It is true. In fact, I love anal sex. I regularly have orgasms when having it. But before you celebrate, I have to add, that it has to be done correctly by someone who knows what they are doing."

Sophie jumps in, "See. You need to know what you are doing or I won't enjoy it."

Tif adds, "Both of you need to know what you are doing, not just the guy."

Robert says, "Ha!"

They finish up their meal. Robert looks at his wife and says, "Hon. Are you interested in inviting our young friend back to our room so she can guide us through an anal experience? Then you would enjoy it?"

Sophie looks at Tif, who nods and says, "I'm game if you are."

Sophie says, "Okay, but you are to take her every instruction without argument then!"

Robert agrees. Tif says, "Robert, can you give me and Sophie an hour to prepare for this event without you?"

Robert frowns and is ready to disagree when Tif adds on, "You want her to enjoy it right? Well, she needs more prep than you do."

Robert shakes his head and signals for the bill. He says, "I will hang out here until 2 pm then."

The girls head into the hotel and up to the couple's room. As soon as they get into the room, the woman looks at Tif and says, "Thank you so much for helping us out. I have wanted to do anal for a long time, but I am afraid. And he pressures me all the time since I told him I was interested."

Tif says, "I think we are both going to enjoy it. Let's get you ready."

Tif leads her to the bathroom and starts to undress her. Halfway through, Tif starts to explain what 'getting her ready' entails.