Izzy is Taught to Handle 4 Guys

Story seven: Tif Teaches Izzy How to Handle More Than One Guy

This is the seventh independent story of our teenage whore Tiffany "Tif". This story accompanies the Katherine "Kat" storyline. The timing of this event occurs between the end of Kat's first module and the beginning of the second module; specifically during the first couple of weeks of summer. 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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Tif and Kat are in the car on the way to the swinger house to pick up Izzy when Kat says, "I remember you met Izzy as part of the outdoor game at the house a couple months ago. But remind me what happened and how you ended up volunteering to mentor her."

Tif replies, "You had an appointment at the house, I don't remember who it was with. I chose to go with you and just hang out. I went out to the back patio and walked up on Izzy and two of her friends, Rob and Steve. We ended up playing truth or dare, which I did not know at the time is a usual weekly event. Anyway, during the dares, I learned that Izzy is shy but also very sexual. We were dared to do some light sexual stuff between us and she was turned on but nervous. So I told her I would work with her on becoming more comfortable doing stuff with girls."

Kat interrupts, "Which is what we are doing next weekend with Steph right?"

Tif replies, "Right."

Kat asks, "So what is this about you mentoring her on being with more than one guy?"

Tif says, "Well, the game continued and the dares became more involved. One dare included guy and a girl that were not part of our group. Long story short, the game went by the wayside and people started hooking up with each other. The other girl fell out quickly leaving Izzy and I. Izzy was overly nervous so she focused on one of her guy friends leaving me with the other two. Naturally, I took care of them. Afterward, I got props from the guys and envy from Izzy. I told her I would help her get better at handling more than one guy."

Kat remarks, "Well, aren't you the little helper?"

Tif responds, "Hey. It wasn't that long ago that you got some mentoring. You had some help along the way becoming the badass you are now."

Kat laughs and says, "Yeah. Yeah. I am on board. Remind me again what you want me to do today."

"I am going to concentrate on giving live instructions to Izzy. So I would like you to have two roles. First, stay connected to me and orchestrate guys coming in and out of the scene. We need to tell them what they are to do with Izzy. The second role is that you may need to be a fluffer. If there is a period of time before a guy is to go in and do something, I don't want him getting bored. It is going to be hard enough for Izzy to multi task. I don't want her to also have to always get the guy erect on top of it."

"Alrighty then."

The girls pull up next to the house and park on the street. They walk into the living room. Kat sees Will and Moe, both regular oral recipients of hers, on the couch. Kat tells Tif she'll be right out and walks over and gives Moe a hug. He squeezes her ass. Then she kisses Will. They have a small conversation before Kat says she needs to go. Kat heads outside to meet Izzy.

Izzy is standing in her usual spot with her usual friends, Rob and Steve. Tif is already by her side. Izzy is tall with flowing black hair. She has the strong body of a recent athlete. Kat approaches the group with a warm smile. As she approaches Tif says, "And here she is. Everybody meet my best friend Kat."

Kat hugs and gives a kiss on the cheek to Rob and to Steve. Kat comes to Izzy and embraces her. They are almost eye-to-eye. Kat leans in and kisses Izzy softly on the lips and says, "I am pleased to finally meet you. I am looking forward to today."

Izzy lowers her head a little displaying her shyness. Tif interjects, "Izzy, a soft kiss on the lips is an inviting welcome. You have nothing to be shy about. We'll get to that later. Guys, will you excuse us girls so we can talk to Izzy and get her ready?"

Izzy looks up and says, "Can't we do this here, with these guys?"

Tif says, "We could. If I felt that you only wanted to ever be with these guys, then that would be okay. But if you really want to learn how to manage multiple guys and get good at it, you have to do it with guys you do not have an emotional attachment to, so we can focus on mechanics. Don't worry, we will be there helping you every step of the way. Besides, Kat knows these guys pretty well and will vouch for them."

Izzy nods her head and says goodbye to her friends. They wish her luck and the girls head into the house. They find chairs in the dining room and begin to talk.

Tif starts, "Izzy. Explain to us why you want to be with more than one guy. In fact, maybe tell us why you want this lifestyle first."

Izzy replies, "Short answer is that I am always horny. My dad caught me masturbating a few times and said he heard me numerous other times. Then he caught me having sex with an old boyfriend. So he knew I was sexually active. My dad is a member of this house. So, when I came of age, he worked out a deal with Richard for me to experiment with some guys in the house. I even experimented with a couple girls, one-on-one of course. Rob and Steve were two guys I experimented with and I have stayed close to them ever since."

Kat asks, "So why not have a boyfriend and have sex with him every day?"

Izzy says, "Because I am genuinely interested in lots of people. I want to experience having sex with lots of members of this house. I am just nervous, so I talk myself out of setting up or accepting appointments. Then I saw Tif in action firsthand and was in awe. I want to be like her."

Tif blushes a little and says, "That is why we are having this conversation today. Have you tried to be with more than one person at a time? Have you had a threesome before?"

"I have tried to have a threesome with Steve and Rob before. Both times it ended up being one-on-one back to back as opposed to all three of us engaged at once. I feel like I get so focused on the one thing I am doing, that I stop doing anything else. I think I am bad at multi tasking."

Kat says, "So to sum up what we heard, you are a very sexual person, but maybe don't have the confidence to act on it. And that is probably a big contributor to you being so focused on one sexual act that you struggle with multi tasking. Did I get that right?"

Izzy says, "I think so. I had never thought of it as a confidence issue before, but I think you are right."

They continue to go back and forth and delve into any specific concerns that Izzy has. Finally they get to the mechanics of the planned event for the day.

Tif says, "Let's talk through what we are going to do today. First, Kat describe the guys for Izzy so she knows what to expect."

Kat says, "All of them are 21 or 22, so a little older than us. Two of the guys are friends of my older brothers. The first guy goes by the nickname Rock. He uses it because his real name is horrible, apparently. He is tall and sexy. He has a very big dick that he keeps shaved. He can get excited from time to time and you can tell he watches porn all the time because he always wants to do facials and things like that."

Tif jumps in, "He has a big cum load. That is why Kat likes him."

Kat smiles and continues, "His roommate is Zach. Zach is a normal looking college guy. He has a long skinny dick. When he cums he has high volume rapid shots. You will need to be prepared for that. The third guy is our host. His name is Sam. He looks pretty normal. He is the sweetest guy ever. Not sure why he is friends with the other guys to be honest. He has a mostly average dick, but thicker than usual. He has a pretty average cum shot. The last guy is Sam's roommate Eric. He is pretty cute. He has a fat dick and enormous balls. He usually has a huge bust when he cums."

Izzy reacts, "Four guys? Holy moly. How am I going to handle four guys? I struggle with two."

Tif says, "I wanted you to experience lots of different situations and lots of different personalities. It is not an uncommon mixture that you might come across in real life. We will not give you more than we think you can handle and if you are struggling with something, it is okay. The guys know it is a learning experience for you and will handle it accordingly."

Tif spends the next 15 minutes walking through the various scenarios she envisions are possible. She asks Izzy, "Have you ever done anal?"

Izzy responds, "Not with a person. I have used a dildo before. I really want to do anal with a guy. Did you plan on me doing it today?"

Tif replies, "If you were already comfortable with it, we might include it or introduce double penetration. But if you are not prepped, I don't think today is the best day to do it. Let's see how today goes and if it goes well, I will help you in a session with Rob and Steve and we can include an anal lesson."

Izzy's face brightens up. She says, "Okay. That sounds great."

Tif asks, "Are you sure you want to continue and go through with this?"

Izzy replies, "I think I am ready to do this. Let's go."

The 3 girls jump in Kat's car and head to Sam's house. On the way there, Tif lays out a couple strategies. She states, "One strategy is to try to get a guy to cum as fast as you can so you can move to the next one. Do you know some tricks for that?"

Izzy replies, "Well, I am not an expert at deepthroating, but I am very good with my hands. When I focus on trying to get a guy to cum, I am usually pretty good."

Tif says, "That's good. I would only use that in specific targeted instances. The goal is for you to have fun not power through it. Otherwise, why do it right?"

Izzy shakes her head in agreement. Tif continues, "Your second strategy and the one we are going to work on mostly today, is to multi task while still being able to enjoy it. We are going to teach you how to handle multiple guys orally and how to handle a guy with your mouth while you are having sex as well. Maybe we will even have you sucking one guy while stroking two others. We'll see how you do."

Izzy says, "So how do I enjoy it if I am concentrating so much on what I am doing?"

Tif responds, "It is a process, but there is nothing wrong with pausing what you are doing to moan or enjoy an orgasm. But you have to get back to it and not get completely lost."

Kat pulls up to the apartment building and parks. Tif asks Izzy one more time if she is ready. Izzy shakes her head in agreement. They knock on the door and Sam answers. He gives them a warm smile and welcomes them in with hugs. Sam tells Kat that Rock is running late, but they should not wait on him.

The crowd spends some time with idle chat and getting acquainted. During the conversation, the guys are looking Izzy up and down. She is very curvy with a nice ass and a handful of tits. She has very pretty eyes that can be mesmerizing.

Once everyone is acquainted, Tif lays out the rules and roles. "I will be with Izzy the whole time giving instructions and advice as needed. Kat will be the traffic cop. If you want to get involved, you go through her as opposed to just jumping in. This needs to be a controlled environment."

All the guys agree. Tif says, "Excellent. Let's get started."

Kat speaks up, "I have a suggestion for a way Izzy can get comfortable right away. Guys, please stand up. Izzy, follow me."

Izzy follows Kat to the beginning of the line of guys. Kat looks at Izzy and says, "Remember when I met you earlier today at the house, and I kissed you gently?"

Izzy nods in confirmation. Kat continues, "Well, it is similar with guys. In this case, I would be a little more sexual because your intent is more sexual. Introduce yourself to each guy."

Izzy nods and approaches Sam, who is first. He is a little shorter than her so she leans down and kisses him. She pushes the sensuality by sliding her tongue in his mouth and leading the kiss. He reaches around and squeezes her supple ass.

After a few moments, Izzy breaks the kiss and moves to Eric, who is next to Sam. He is eye level and accepts Izzy into his space. Their kiss is immediately sexual. Sam starts getting undressed in the background. While still sharing an intense kiss, Eric reaches down and starts sliding Izzy's skirt down. Without breaking the kiss, Izzy steps out of her skirt.

A naked Sam comes up behind Izzy and gently kisses her butt cheek, Izzy jumps a little and breaks her kiss. Sam gently kisses the other butt cheek as he slides his fingers into the waistband of her thong. He slowly pulls them down as Izzy turns a little and smiles down at him.

Eric reaches down and pulls the bottom of Izzy's tank top over her head. Zach joins the group and unclasps her bra freeing her full round tits. Now naked, she turns and kisses Zach while 3 sets of hands explore her naked body. In between gentle gropes, Eric and Zach finish getting themselves undressed.

Zach gently grips a handful of breast and attaches his mouth to one of her delicious nipples. Eric reaches in between her legs over her closely shaved bush and starts massaging her pussy; which is already wet with anticipation. Sam stifles Izzy's moan with a kiss.

Izzy breaks the kiss and lets out a big moan. Zach has switched nipples and Eric has moved directly to her clit. Before the action gets too heavy, Kat intervenes to reorganize the group. She pulls Zach and Eric away and instructs the host to go first.

Sam is not fully erect, so Tif instructs Izzy to help him out. She drops to her knees and brings his half hard member fully into her mouth. She sucks hard as she pulls off. Izzy wraps her hand around the base of his shaft and starts to bob. Within a minute, Sam's manhood is standing at attention.

Once Izzy establishes a rhythm, Kat sends Eric back in. Tif instructs her to keep Sam hard with her hands while she brings Eric to attention. At first glance she is enamored with his huge balls. She struggles to keep Sam hard while she focuses on Eric at first, but then finds her way with encouragement from Tif. Izzy pulls off of Eric and looks at Sam's erection in her left hand and Eric's fat unit on her right. She smiles.

Now that Eric is hard, Tif instructs Izzy on how to go back and forth between the guys, making sure each one is getting specialized attention without feeling left out. Izzy builds a rhythm where she takes one of the guys in deep and holds it there for a brief second. During that second, she strokes the other guy a couple times. A few times up and down and then she switches attention.

At Kat's instruction, Sam pulls away and lies down on the floor. Tif instructs Izzy to sit on his face. When she does, he puts his hands on her ass and pulls her in close. Then he attaches himself to her pussy licking up and down her tiny folds. Sam worlks up and down swallowing little bits of nectar along the way. Soon he settles in on her clit and goes to task immediately sending shock waves through her body. Tif instructs her to return to task with Eric.

Multiple times Izzy stops blowing Eric as a spasm surges through her body as Sam continues to lap and suck on her sweet pussy. Tif has to refocus Izzy a few times when her breaks go too long. Finally Tif asks Sam to take a break. He goes over and replaces Zach who was getting fluffed from Kat.

Zach moves in next to Eric and Izzy practices going back and forth between the two. She gains a rhythm more quickly than the first time. Tif lets this go on for a while until Eric gives Tif the hint he needs to break away before he busts. Tif sends him to the couch. Sam comes over and replaces him. Izzy continues without missing a beat, causing Tif to praise her for her adapting so quickly.

Izzy starts to moan in enjoyment as she sucks and strokes the two erections in front of her. Tif gives the signal to Kat who sends Eric back in. Tif instructs him to lie on his back this time. She tells Izzy to break away from the guys and mount Eric. Kat keeps the guys hard while Izzy get used to Eric. She hovers over his long dick for several seconds before she reaches down and positions him at her holy entrance. She rubs his head up and down her slit to moisten his entrance and then slowly slides down.

Only a about an inch at first, then all the way back out. Then almost 2 inches down and back out, her pussy squeezing his erection both directions. A few more strokes barely gain any advantage. Tif asks her to hover completely off for a moment. When she does, Tif grips Eric's meat and slides her mouth all the way down it causing a moan to escape out of Eric. She leaves a saliva trail behind for lubrication and then points him back up at Izzy.

Tif says, "Slide down again and see if that lubrication helps you out a little. And by the way, you are quite tasty. I can't wait to put my mouth on you."

Izzy blushes a little and then aims her love nest back over Eric's erection. She is able to go down a couple more inches this time. Tif leans her back a little and then reaches down and starts massaging Izzy's clit as she moves up and down. Her pussy tightens and loosens and she sinks down a couple more inches. Eric moans as Izzy squeezes his manhood with her tightness. Izzy takes in a short breath at the top and lets it out at the bottom, each time going a little more down.

This repeats several more times until Izzy pushes down hard and lets go of a big orgasm. Her legs shake and she leans farther back on Eric's shaft. Her pussy tightens with each wave of orgasmic bliss. Eric grunts and unexpectedly loses his load inside Izzy. He fires shot after shot of hot cum inside her matching her pulses almost exactly. Finally Izzy collapses down on top of Eric as their shared orgasm comes to a close.

Tif says, "Oh no. I had not planned on that. What happened Eric?"

Eric takes in a deep breathe and replies, "I couldn't help it. She is super tight."

Tif sighs, "It's okay. We will adapt. Izzy, slowly come off of Eric and push his cum out. Kat, you're on clean up duty. Izzy come with me."

Izzy pulls off of a softening Eric and pushes his cum back out onto his groin. Then she stands up to follow Tif to the bathroom. Kat stops sucking Sam and Zach and comes over to clean up Eric. She reaches out and takes Eric's now limp tool and brings her mouth down to it. She cleans it up nicely and then spends some time cleaning the rest of his midsection.

Tif grabs her purse and leads Izzy to the bathroom. Once in, she pulls out her baby wipes and hands a couple to Izzy. While Izzy cleans herself up Tif starts talking, "Ordinarily Kat or I would have cleaned you up, but I want to focus our lesson on the guys today. Otherwise, Izzy, I think you are doing wonderfully. You are taking instruction well and so far you are keeping these guys going. Are you enjoying yourself?"

Izzy pauses and then answers, "I thought I was doing okay. But then I look over and see that Kat is working the guys over as well. So it isn't really me. Then I made Eric cum by accident. I'm sorry Tif."

Tif looks at her sympathetically and says, "No No No. Izzy, You're doing great. I did not expect you to be perfect the first time. It was never my intent for you to try to keep all 4 guys going. Kat is here to help. You will get better with practice. Now, as it goes with Eric, well, things happen. There are still a few other guys to get back out there with. I want you to enjoy yourself."

Izzy smiles and says, "I am. I will try to have more fun."

The girls come out from the bathroom. The guys are all on the couch laughing. Kat is standing talking to Rock.