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This is the fourth 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.
It’s about to be spring break of her senior year and Tif is feeling sad. She just found out that her best friend and favorite lover Kat is going to be in Hawaii with her family. One of Tif’s cheerleading teammates, Callie, comes into the locker room and says, “What’s up Tif? You look down.”
Tif replies, “Spring break is coming up and I have not planned anything. I am terrible at planning.”
Callie snidely says, “I thought you might be hanging out with Kat. You two are thick as thieves. If I didn’t know better, I would think you two were lovers.”
Tif does not acknowledge the dig and says, “Kat is going to be with her family on vacation. That is irrelevant to my point. I need to figure out what I am going to do.”
Callie smiles, “Well, a few of us girls are going to Cabo San Lucas. Do you want to go? All you would have to cover is airfare. The rest is covered.”
Tif’s eyes light up. She asks, “Who else is going and why are the rest of the expenses covered?”
Callie replies, “In addition to me, it will be Michelle and Nicole. We would all be sharing a room. Nicole’s and Michelle’s dads are going as chaperones. They are both single so I think they are going so they can try to hook up with young chicks. Anyway, Nicole’s dad is paying for most of the stuff since he is well off. “
Tif replies, “I did not know they were single.”
Callie answers, “Nicole’s dad is a widower. Nicole’s mom, died a few years ago. As far as I can gather, he does not have a steady girlfriend. Michelle’s mom and dad divorced when she was 4 or 5 I think. He got remarried and divorced again. A few years ago I think.”
Tif considers the offer. She likes all these girls. She would consider them friends. And it would give her an excuse to hook up with new hot people. She replies, “Count me in then.”
Callie smiles and says, “Excellent. I will text you the details so you can get on our flight.”
The flight to Cabo was easy. Tif had great conversation with the other girls. They switched seats often to keep the topics fresh. Inadvertently, Tif found out that Callie is bisexual, that Nicole is bi-curious and that Michelle has never considered it because she has always had a boyfriend. Tif also learned that Callie is unattached, but both Nicole and Michelle have boyfriends.
The most interesting discovery Tif made on the flight over was that Nicole’s dad, Jack, has barely been on a date since his wife died. It is not through lack of effort. He is a handsome guy. But apparently, he has no game. She learned that Michelle’s dad is also good looking and a bit of a player who chases tail a lot; hence his multiple divorces. They both eyeball the girls, especially Tif, all the way to Cabo.
The flight arrives late in the evening. They get a quick bite to eat and then head to their rooms to get settled and crash. Callie leads the charge by assigning Tif to share her bed while Michelle and Nicole share the other.
Once Tif and Callie come out of the bathroom, Michelle and Nicole head in to get ready for bed while Tif and Callie head to the bedroom. As Tif gets undressed, she catches Callie looking at her. Tif asks, “What?”
Callie smiles and responds, “I have always thought you were hot as hell. I mean, you’re a prototypical cheerleader who is blonde, athletic, pretty. But you have incredibly sexy legs and a super nice ass. You probably have great tits too.”
Tif is a little shocked. She responds, “I had no idea you looked at me that way. You’re pretty hot yourself.”
Callie finishes pulling her clothes off and stands naked in front of Tif. She turns around in a circle slowly and asks, “What do you think my most attractive feature is?”
Tif looks her up and down and salivates a little. She finally responds, “Hard to tell. You have so many good features. You’re a tall brunette with long sexy legs, a pretty face and a more than handful of tits. But I think your sexiest feature might be that bald pussy of yours. I am sure the guys love it.”
Callie smiles and remarks, “The girls love it too.”
Tif says to Callie, “I usually sleep naked, but of that bothers you, I won’t do it this week.”
Callie responds, “You normally sleep naked? Me too. I planned on sleeping naked like usual. Unless it is going to bother you?”
Both girls giggle a little.
Tif finishes taking her clothes off. Callie comments, “You do have nice tits. Those bayan arkadaş nipples look delightful.”
Tif smiles and crawls under the sheets. Michelle and Nicole make their way out of the bathroom. Michelle is a short, thick, powerful brunette with big D cup tits that are not hidden very well by her bedtime t-shirt. Nicole is a thin, blonde with a very flat stomach and what appear to be B cup tits under her tank top. Finally all the girls are tucked in bed and lights go out.
Some time in the middle of the night, Callie works her way over to the other side of the bed. She gently snuggles up next to a lightly sleeping Tif. Callie sighs as she feels her hand against the nakedness of Tif’s body. Callie gently rubs her hand up and down Tif’s leg. She brings her hand down to Tif’s supple ass cheek and gives it a small squeeze. Tif jostles a little but does not seem to wake up.
Callie runs her hand up and down Tif’s leg again. She also leans down and plants a dozen tender kisses down Tif’s bare back. Tif jostles again, this time turning toward Callie some, almost fully lying on her back. Tif crinkles her nose and then appears to doze back off.
Callie waits a couple minutes and then runs her hands over Tif’s flat stomach and then down her hip and finally her leg. She follows this pattern two more times before her return trip has a detour. Callie softly runs her hands over Tif’s lower stomach and then slowly heads farther down. Callie smiles as she passes over the completely shaven part of Tif’s pussy and touches the top of her wetness.
Tif jostles again, this time causing her to completely lie on her back. She puts both of her arms under her pillow and pushes her head to the side. Callie raises her hand off of Tif and lets her settle. Callie waits a few minutes and then swiftly pulls the sheet off of both girls. As they lie there completely exposed, she goes back to where she left off.
Callie lands her hand on Tif’s pubic bone and moves down. She starts to slide her middle finger down making sure not to put too much pressure on her clit. She gently runs her finger up and down Tif’s moist slit. After a dozen times up and down, Tif’s pussy starts getting wetter. It is subtle, but Callie realizes that Tif’s legs are parting ever so slightly. With the extra space, Callie pauses to push her middle finger into Tif’s small opening, only to the first knuckle the first few times.
Tif’s legs part some more. With the further encouragement, she slides her finger in to the second knuckle. In and out her finger moves slowly. Callie pushes her middle finger in deep and pulls it back out slowly. She puts her coated finger to her mouth and sucks it clean. Then she moves back in sliding her middle finger back in deep. In and out a few more times and then back to her mouth.
When Callie goes back a third time, she adds a second finger. She is still gentle, but eventually gets both fingers deep inside Tif’s wet tunnel. The next time she pulls her fingers out; she moves them up a little and starts slowly circling Tif’s clit. Tif spreads her legs even more and she moves her upper body slightly.
Callie slides two fingers back inside Tif and leaves them there while she skillfully massages Tif’s clit with her thumb. The very experienced move causes a small moan to escape Tif’s lips. Callie uses this as a sign. Without breaking the hand movements, she leans down and puts her mouth on one of Tif’s nipples. She gently sucks and swirls her nipple causing a more audible moan to escape from Tif.
Tif spreads her legs completely and pulls her left hand from under the pillow. She runs her hand through Callie’s hair and moans again. Callie pulls her hand out of Tif and repositions her body in between Tif’s spread open legs. Callie takes hold of each of Tif’s breasts and leans down and starts sucking on the other nipple. She squeezes and fondles Tif’s tits while she goes back and forth sucking her nipples. As Callie heads down, she leaves Tif’s nipples hard and aimed at the sky.
Callie kisses her way down Tif’s stomach and soon reaches the promise land. She wastes no time putting her mouth on Tif’s love nest. She licks up her slit stopping to flick her clit and then back down. She pushes her tongue inside her box over and over and then back up to the clit. She pulls the entire hood inside her mouth and swirls it with her tongue. Tif reaches down and runs her hands through Callie’s hair again.
Callie continues to munch on Tif’s edibles causing Tif to moan. She moves her hands up to Tif’s nipples and starts pinching them more intently. She shoves her face deep into Tif’s bare box licking and sucking all the sensitive places. Finally she stays on Tif’s clit and flicks it vigorously. Tif moans, then lifts her hips and pulls Callie into her deeper. Tif lets go of her orgasm filling Callie’s mouth with sweet juice; which she gobbles up and swallows down.
Callie pulls off slightly and moves her hands from Tif’s nipples bayan partner to behind her legs. She pushes Tif’s legs into the air and sends her head back down. She makes a small stop back on Tif’s pussy and then heads farther down. She runs her tongue over the soft skin below her pussy and soon hits Tif’s rosebud. She flicks it a few times and the presses harder with her tongue. She leaves a generous amount of saliva behind. This causes Tif to moan again.
Callie wraps one hand around Tif’s leg and rests it on top of her pussy. She starts circling Tif’s clit again. Callie moves her other hand to Tif’s anal opening. Using the extra saliva, she starts massaging her pink star with her thumb. Tif starts moaning again. After a few moments of this, Callie slides a finger into Tif’s pucker hole. When Tif does not resist, she pushes it deeper and then back out. She repeats this several times when she recognizes Tif rocking her hips. She pulls her finger completely out and starts tonguing Tiff’s butthole again.
This continues for a few moments before Callie leaves another dollop of saliva. Then she slides two fingers deep into Tif’s anal passage. This causes Tif to moan and start rocking her hips again. Callie smiles as she realizes that Tif is an anal lover like herself. She starts moving her fingers in and out Tif’s ass faster and harder. She leans down and starts tonguing Tif’s pussy hard. Within minutes, Tif groans much too loud and tightens her ass around Callie’s fingers and explodes in a huge orgasm. Yummy pussy juice floods Callie’s face again. She drinks it down.
Callie pulls off of Tif’s pussy and ass when she feels Tif stop shaking. She kisses up her stomach, pausing to lick and orally caress each nipple. She continues to kiss up Tif’s chest and starts kissing Tif’s neck. Tif cannot wait any longer and uses her hands to bring Callie’s face into hers. Tif pushes her tongue into Callie’s accepting mouth. Tif can taste her own orgasm on her lips and tongue.
Callie lets her weight come down on top of Tif. As they continue to kiss, Tif wraps her legs around Callie and pulls her close. They tongue hard and hungry. Tif rolls Callie over on her back and it is now Tif in the dominant position. She quickly breaks the kiss and works her way down Callie’s neck to her tits. She takes a tit in each hand and sucks hard on each nipple before moving on. She kisses down her stomach and quickly makes it to her vulnerable places.
Tif wastes no time putting her hands on Callie’s hot box. Tif realizes that she is drenched. She lowers her face down and licks up the inside of Callie’s leg cleaning up tasty lady juice. She does the same on the other leg. Tif pushes her legs up high. Then Tif flattens her tongue and runs it from Callies butthole all the way up past her clit. Tif repeats this several times before the copious amount of lady juice is gone. A soft ‘ah fuck!’ can be heard from Callie.
Callie pulls her legs up by her ears baring herself to Tif’s pleasures. Tif goes right for the ass. She licks her pucker hole a few times before Callie reaches down and spreads her cheeks even more. This opens up her hole even further for Tif’s access. Tif takes advantage and shoves her tongue in deeper. She tongue fucks her for a few minutes causing Callie to moan in appreciation.
Tif licks her fingers and pushes two fingers into Callie’s ass. Callie moans and rocks her hips. Tif pushes them in deeper causing Callie to moan a little louder. Callie’s ass relaxes even more. Tif pulls out and pushes in a third finger. Soon Tif is shoving her three fingers all the way in. Callie is bucking her hips even harder now. Tif pulls out and adds a fourth finger. She pushes it in slowly. Callie reaches down and pulls Tif’s hand causing all four fingers to go all the way in. Callie moves her hips in a circular motion, feeling the full effects of having four fingers lodged in her ass.
Tif leans down and starts licking Callie’s clit sending her into small convulsions. Callie’s pussy is leaking so much wetness, it starts running down to her ass-crack. It assists in the finger fucking. Tif spits some saliva into her hand and fingers to add to the lubrication. Callie starts pulling Tif in deeper while she continues to rotate her hips. Soon Tif’s top knuckles pop through causing a small yelp from Callie. She continues to push her ass against Tif’s hand sending more and more in. Within a couple minutes, Tif has her whole hand inside Callie’s ass, her thumb being the only missing part of a full fisting.
Callie starts pushing and pulling Tif’s hand wanting to be fucked. Tif gets the idea and starts doing the motion herself, fucking Callie with her with most of her hand. Tif increases the pace with her hand and her mouth. Callie continues to hump Tif’s hand until she finally tightens up and groans loudly. Her orgasm squeezes Tif’s hand and sends a flood of lady juice into Tif’s mouth and down her throat.
As Callie’s orgasm subsides, Tif slowly bdsm escort pulls her hand out of her ass. Callie lowers her legs and pulls Tif up to her. They kiss for several minutes vigorously at first, passionate in the middle and then tender at the end. Tif breaks the kiss and then tells Callie, “You’re a bad girl.”
Callie responds, “So are you.”
Callie gets up and cleans herself up in the bathroom. When she comes out, Tif goes in to clean herself up. When Tif returns, Callie is asleep. So Tif crawls in bed next to her and goes to sleep.
The next morning Tif wakes up and has Callie wrapped around her. She peeks over to the other bed and sees that Michelle and Nicole are gone. Tif starts to slide forward moving out from underneath the weight of Callie’s arm and leg. Just before she makes it to freedom, Callie grabs onto her and pulls her back into her grasp. Tif falls back into bed this time facing a smiling Callie.
Callie says, “Where do you think you’re going lover?”
Callie kisses her and slips her tongue in. Tif returns the favor, but breaks the kiss soon after.
Tif says, “We should get up and get decent in case Michelle and Nicole come back.”
Callie responds, “Where is the fun in that? Can we sneak in at least one quick orgasm?”
Tif says, “Ok. But it has to be quick.”
Tif pushes Callie on her back and quickly crawls on top to 69. Both girls start lapping up right away. Callie starts flicking Tif’s clit rapidly sending her into a frenzy. Tif sticks a finger in Callie’s pussy and another in her ass and fucks her while she licks her clit. Callie is the first to cum sending some juice into Tif’s mouth. Tif is not far behind. She shakes in a good morning orgasm.
The girls dismount and quickly shower and ready themselves. They barely make it down to the hotel restaurant for breakfast. Over in the corner, they see their chaperones. They decide to join them. As they approach, both guys smile and look the girls up and down.
Brett speaks first, “Well. Well. Well. Look who we have here. I told you if we sat here long enough a coupe of beauties would join us Jack.”
Jack replies, “These beauties are our daughters friends Brett. Hi girls, come join us.”
The girls sit down. They work through their food. As Jack does most of the talking, Brett can’t stop ogling Tif. It is blatant and probably inappropriate. Tif does not take the bait. She seems sexually satisfied for the moment.
The girls head to the beach to meet up with Michelle and Nicole. As they get arranged, the small talk is minimum. Finally all are sunning. Callie mentions that she wants to go get drinks. Michelle volunteers to show her where to go.
Tif asks Nicole, “So why are you and Michelle so quiet? Is something wrong?”
Michelle hesitates but answers, “Kinda. Your activities with Callie last night woke Michelle and I up. And kept us up for an hour. I am not that mad. I am more curious. But Michelle is pretty unhappy.”
Tif turns red, “At what point did we wake you?”
“Michelle woke me actually. The first thing I heard from you guys were some moans that I thought might have been one of you having a bad dream. But then Callie told you to fuck her harder. So I knew what was going on at that point.”
Tif turns even more red, “Oh. Uh. I’m really sorry we woke you. What can we do to make it up to you?”
Nicole looks around to see if anyone else is around. Then she says, “As I said, I am not that mad. In fact, it turned me on listening to you two go at it. It was super dark, so I could not see anything, but I tried to picture it.”
Tif says, “Oh.”
Nicole continues, “I am going to tell you a secret.”
“I have never been with a girl. But I have thought about it a lot. It turns me on to see women kissing or caressing each other. I think the woman’s body is so hot.”
Tif replies, “So what stops you?”
“One, I have a boyfriend. Two, I am incredibly nervous and don’t really know what I am doing.”
Tif smiles, “Do you know how to please yourself?”
Nicole replies, “Of course.”
Tif says, “Well, it is not much more than that. What I will say is that it is true that different women like different things, but you know most of the variations I am sure. You just need to find a patient partner and explore.”
Nicole sighs, “And how do I go about doing that?”
Tif laughs, “Hello. I am right here.”
“But it seems that you are way too experienced for me.”
“I said find a patient partner, not an experienced one. I am patient and I would be interested in guiding you through whatever experience you want to have and at whatever speed.”
Nicole blushes, “That might be nice. What about Callie?”
“Callie is obviously aggressive. But I think I can keep her reigned in if you want her to participate.”
Just then Callie and Michelle return bringing drinks. The rest of the morning goes well. The girls spend time in and out of the water and getting hit on by hot guys. The girls decide to head back to the room for lunch and some rest away from the sun. While in route, Tif and Callie bring each other up on their respective conversations with Michelle and Nicole.
Callie says, “Yeah. Michelle is a bit pissed.”
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