Outdoor Truth or Dare

Story three: Outdoor Truth or Dare

This is the third 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 nine part two. 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 arrive at the house early afternoon on Saturday. The house is owned and run by a man named Richard. He is her dad's boss and he also happens to be Kat's mentor. The house appears to be a normal house, but is used for all varieties of sexual activities by its members. It is a swinger house. Tif and Kat have recently become members.

Kat has a sexual appointment with a family friend, who is also her dad's co-worker. His name is Tony. Kat is a little nervous since she knows the guy. Tif is here unattached so she can support her best friend.

When they arrive, there are a lot of people 'hanging out' at the house, meaning they do not have an appointment and are available to be invited to join other activities. The girls head up to the bedroom that Tony booked. Tony has not arrived yet. The girls sit down on the edge of the bed and talk.

Tif starts by asking, "On a scale of 1-10 how nervous are you?"

Kat replies, "Maybe a 7. And it is completely because I have known him for years. He has eaten dinner at my house. He is a co-worker of my dads and they see each other every day. I am not nervous at all sexually."

Tif continues, "On the other side of it, how turned on are you to hook up with an older hot guy?"

Kat smiles, "Very. I am very hungry for some cum. I appreciate what you gave me last night, but it is fading about now. I am looking forward to the encounter hoping I get a delicious load in my mouth."

Tif tells her, "Well, I am here to support you. Come downstairs and find me when you are done. Text me if you need me before."

Kat looks at her best friend lovingly and says, "I am sure I will be fine. But thanks for being there for me."

Just then Tony knocks on the door. Kat tells him to come in.

Tif looks at Kat and says, "I was just leaving. See you soon babe."

Tif leaves Kat alone in the room with Tony. She wishes her a silent good luck and heads downstairs. When she gets downstairs, there is no one in the living room or the kitchen. It seems eerily quiet given all the bustle that was going on when they arrived.

Tif decides to head outside to enjoy the nice weather. When she walks onto the patio, she sees a bunch of people outside with the same idea she has. There are a few people in the pool. There is a guy sitting on the top step of the pool entrance. He has a naked brunette sitting on top of him. The up and down motion gives away what they are doing.

Tif continues to survey the scene and sees a few people lying out tanning. A couple of them are naked hoping for no tan lines. There is a guy lying back on a pool chair with a tanned blonde sucking his dick. Seeing these people in action is making Tif a little hot herself.

Tif looks over to the outdoor bar and sees 2 guys and a girl laughing and talking. Tif decides that is her spot. She heads over to say hello.

As Tif steps up next to the girl, she says, "Hi there. I'm Tif. Nice day to be outside next to the pool and take in the scenery isn't it?"

The tall handsome guy with blonde hair and a tanned surfer body says, "Ah, the new girl. My name is Steve. Welcome to the house."

The slightly shorter, but athletic looking guy with brown hair says, "I'm Rob. Good to see you here."

The girl, who has long black hair and a curvy body says, "I'm Isabelle. People call me Izzy. Finally another girl to join our conversation." Tif notices that in addition to having very sexy hands with painted nails, she also has very pretty eyes with long eyelashes.

Rob laughs, "And quite the conversation it is."

Izzy looks at Tif and says, "We were talking about the best position for a blowjob. As you would expect there are different opinions from the guys to this girl."

Tif says, "So catch me up. What is everyone's favorite position?"

Steve says, "Oh no no no. We need to hear your favorite before we can continue."

Tif thinks for a minute. Then she says, it is so hard to choose. I mean. I really love to be split roasted. So blowing a guy while getting fucked doggystyle is great. But if it is a straight blowjob and not part of a larger sexual situation, then ... well... dang."

Tif pauses but speaks up again just as Izzy was going to save her, "I've got it. I want my head hanging off the end of a bed. The man comes at me from above. Then he can get his dick all the way down my throat easier. But wait, that is not the best way to swallow cum. Wait..."

Tif pauses again. The others look at her in delight. Then Tif says, "No. I think I've got it. He is standing and I am on my knees. It gives us both the maximum flexibility and also numerous options for the cumshot. That's the one."

The others laugh and agree. Then Rob says, "Tif, I think you are on the guys side. Izzy here likes for the guy to be on his back or in a chair. Then she will go down on him that way."

Izzy says, "It is more sensual. And I am in complete control. Tif, do you like doing it that way?"

Tif replies, "For sure. I do it that way at least once a week."

Izzy smiles like she got a victory.

Rob speaks up, "So Tif, I have read your profile. It says you are full service. I did not see anything in there that you are not willing to do. It tells me you love anal. Is that true?"

Tif says, "It is true. I don't lie. I do love anal. Usually do it once a week at least."

Rob is taken aback, "Once a week. Woo-wee. What about me? My manhood is a little thick. Would you be able to handle a thick dick in your ass?"

Tif smiles and replies, "Of course. I would need some warm-up and some lube. But I am sure I could accommodate."

Rob smiles from ear to ear. Steve adds on, "Well, you better let me go first." They all laugh.

Tif laughs and then says, "No one has said that either of you are getting any ass from me today though."

Izzy smiles and says, "I think I'm going to like you."

Steve says, "I assume you are a popular girl. How come you do not have an appointment right now?"

Tif answers, "I am here to support my best friend Kat."

Rob says, "Ah yes, the other new girl. The one who loves to suck dick and loves cum in her mouth."

Tif says, "Yeah. That's her. She is here for an appointment with Tony. Tony works with her dad and is a family friend. So I am here in case it gets awkward or she needs me for anything."

Rob asks, "So Kat's profile says she is open to the discussion on sex. Does that means she is not up for having sex at all? What does it mean?"

Tif replies, "It means she is very selective at this point. She has only had sex with a handful of men. So she is working up to the promiscuity of it."

Steve says, "Do you think she will have sex with any of the guys in this house? Or Tony today?"

Tif replies, "I don't know. I think she will eventually. Every girl needs a fuck buddy or two."

Izzy shakes her head in agreement.

They continue to talk a while longer, mostly about sex and about Tif. Then Izzy looks at her watch and tells the guys it is time.

Tif says, "Time for what?"

Izzy explains that almost every Saturday, there is a truth or dare game at this time. Anyone around can jump in and participate.

Tif says, "I'm down."

Izzy announces loudly to the rest of the pool area that the game is starting and that if they are going to play, now is the time. She also reminds them that they are all at risk of being included in a dare.

Tif asks, "We can include them in a dare?"

All three shake their head in agreement. Rob suggests that they all start the game naked as usual. They all look at Tif, who shrugs and says okay.

The group starts taking their clothes off and sitting them on the bar. Tif catches the other three peeking at her constantly. Tif looks at Steve. Apparently he has been tanning nude, as he has no tan lines. He has nice abs and is decently muscular. It looks to her like he has a pretty normal size dick. Rob is thicker and more built. He looks like he was telling the truth. Even limp, he has a thick cock. Izzy is very toned and in good shape. Her skin looks flawless.

Once they are all naked, Izzy speaks up first, "Tif, you have a completely hairless pussy. Isn't that hard to maintain?"

Tif smiles and touches herself where she would normally have pubic hair. She says, "I completely shave twice a week. It takes about 5 minutes in the shower. It is not too bad."

Izzy replies, "Don't you have to worry about ingrown hairs?"

Tif replies, "Not really. I use a new razor every other time. Seems to do the trick. And besides it takes me much more time to get my ass ready each day."

Izzy asks, "Ass ready for what?"

Tif smiles and replies, "Well, a girl who loves anal wants to always be prepared."

Izzy looks confused and then it hits her, "Oh. Ohhhhh. I get it. Sorry. This is a bit new to me."

Rob jumps in, "As stimulating as this conversation is, it would be much better if one of us dared you to shave your lady parts. Can we get started?"

Steve says, "Great idea. But I have more fun daring Izzy to do things to and with other women. Although we go easy on her."

Tif looks at Izzy. Izzy blushes and then replies, "I had never even kissed a woman until I became a member of this house a couple months ago."

Tif says, "Are you interested in women?"

Izzy says, "Yes. I am struggling along though. When you don't really know what you are doing, it can be intimidating and embarrassing to try to do things with experienced women."

Tif says, "I understand completely. I think you just need the right woman or women. Kat was in your position a month ago. I know just the right women to help you out. Will you let me help you?"

Izzy looks concerned but shakes her head in agreement. "Let's talk later. We should get the game going."

Steve suggests that ladies first and that the new lady should get first dibs. Everyone agrees. Tif starts off, "Steve - truth or dare?"

Steve replies, "Truth. Let's get started slow."

Tif asks him, "Is there anything that intimidates you sexually?"

Steve replies, "Like what? Give me an example."

Tif says, "Like a threesome with another dude and the other guy has a bigger dick. Or a sexually aggressive woman? Or an older woman?"

Stev laughs and says, "Oh. Uh. No. I don't think so. I have a wide range of sexual experiences, so at this point I know my capabilities and limitations. I have been in a threesome with Rob here before. I just told him I needed to go first."

They all laugh and Rob adds in, "Happens to me all the time."

Next up is Izzy. She asks Tif truth or dare. Tif responds, "Truth, I've got nothing to hide."

Izzy asks her, "What is the most number of men you have taken on at one time. Same for number of women."

With a smile Tif says, "Is that two questions?"

The guys laugh and Izzy frowns. Tif says, "I'm just kidding. Let me think for a moment."

Tif pauses and thinks it through. She smiles halfway through. Then she says, "The most men I have been with without another woman to help me is 4. I can tell you that story some other time. I have only been with two women at a time once. However, I have been in groups where there have been multiple women and multiple guys."

The guys are shaking their heads enjoying her answer and visualizing them included in some scene with Tif later. Izzy stands there a little shocked.

Izzy says, "You are amazing Tif. You need to teach me some things."

Tif says, "I look forward to it."

The game continues with questions for a while before Rob says, "Can we just play dare or dare? We can learn these things during pillow talk later."

Izzy says, "Okay Mr. Impatient. Tif, do you object to moving to dares only?"

Tif says, "I just want to note Rob, that we all have the option to choose dare including yourself when asked. Izzy I am fine with moving to only dares."

Tif is up next, "Rob. You see that blonde chick over there riding Mr. Handsome?" Rob shakes his head yes. "I'd like you to go over there and ask her to lean forward and when she does, tongue her asshole for one minute."

Rob says, "Oh shit. Swinging right out the gate. Okay."

Rob walks over and signals the guy to bring his girl forward. When he does, Rob leans down and starts tonguing her asshole. Her moans get louder and the guy underneath her smiles. He makes it the whole minute. He winks at the guy and heads back to the group.

Rob comes back to the group getting high fives from everybody. Izzy is up next. She says, "That was so hot, Steve, I dare you to go do the same thing to the same girl."

Steve shakes his head and heads over to the couple. The girl is still leaning forward. He signals the guy what he is going to do. He kneels down and tongues her asshole as well. He has a longer tongue and does more work. Inside the minute, the girl's moans turn to a groan and she shakes and has an orgasm. Steve tells the guy you're welcome and heads back to his group. Steve says, "We should not do any further dares with that couple today."

Tif says, "That got me all hot and bothered. I am going to need some dick soon."

Steve is next. He says, "It is time Izzy. I dare you to tongue kiss Tif for a full minute."

Izzy looks at Tif. Tif looks back at Izzy. Tif asks her if she is ready. Izzy shakes her head yes. Izzy is a little taller than Tif, but Tif still leads the motion. Tif reaches over and embraces Izzy's lower half and leads Izzy's hand to her ass. Tif leans in and their lips meet. Tif reaches around and softly squeezes Izzy's ass. As their tongues tango, Izzy gets into the kissing and starts squeezing Tif's ass. The kiss is gentle and passionate. The girls go way beyond the minute, but neither guy complains.

When Tif breaks the kiss, Izzy lingers with her eyes still closed. She slowly opens then and says to Tif, "That was wonderful. You are so sexy."

Tif smiles and replies, "There is more where that came from."

The dares continue around the group. Each person was able to do the dare they were challenged to do. The final dare of the afternoon set Tif up to repeat the performance that Steve and Rob started with.

Tif walks over to the same couple, which has now returned to the same position as before. Tif indicates to the guy to lean his girl forward. When he does, Tif deafly starts licking the balls of the guy underneath and then slowly moves up to the girls pucker hole. Tif gently inserts her tongue in just past the rim and back out several times. Then she flicks and licks her pick star. This causes the girl to lock up for several seconds, her pussy squeezing the guy's cock inside of her. When she lets out her breath, she follows it with a powerful orgasm. Her pussy clinches hard on the man pumping into her from beneath. He can't hold out and lets loose his orgasm inside of her.

Tif steps back to watch their mutual orgasm finish up. By now the other three have gathered around. The girl crawls off of the guy. When she rises off of the man's dick, cum pours out of her pussy onto the man's groin. The woman says, "I need to get cleaned up."

Tif touches her arm and says, "May I take care of that for you?"

The woman looks puzzled, but allows Tif to lead her to the pool chair next to the spent man. Tif lays her on her back and kneels between her legs. Before the woman truly realizes what is happening, Tif has her mouth on the ladies pussy. She licks all around the edges, swallowing the bits of cum she finds. She licks up and down the ladies clit sending jolts of pleasure to the rest of the woman's body. Tif sticks two fingers inside the woman's pussy and digs out all the cum she can reach. She pulls it into her mouth and then goes back to town on cleaning up the woman's pussy. She keeps almost constant attention on the woman's clit until it is time to push her over the edge. Tif sucks in the woman's clit and batters it with her tongue. Within a minute the woman's legs start shaking and a full lady orgasm into leaks into Tif's mouth. Tif spends another minute cleaning her up. Then she stands up and asks if the woman is all right. She responds, "I am wonderful. Thank you." The now satisfied woman gets up and heads into the house.

Tif turns and realizes that Izzy is standing there with her mouth open and her hand massaging her pussy. Steve and Rob are standing their stroking their erections. The new guy, who just busted is standing there with his hands crossed enjoying the scene.

Tif says, "I guess the game is over."

Rob says, "But now the fun begins."

Tif replies, "Well, I owe this gentleman a clean up first. It is only fair."

Tif sits on the pool chair and motions for the mystery man to come over. When he does, Tif leans forward and pulls his limp manhood completely into her mouth. She uses a lot of saliva and sucks him thoroughly and swallows down any remnants from his orgasm. Then she pulls her mouth off his dick and lifts it up and cleans his balls. While she cleans his balls, she strokes him energetically, bringing it back to life.

Meanwhile Steve and Rob are standing next to Izzy with their hands roaming all over her sensitive parts. Izzy has a hand on each man's cock stroking it gently. Steve asks Izzy if she will blow them. Izzy hesitates and says, "You know I am not good at handling more than one of you at a time."

Rob replies, "I am sure Tif can show you a thing or two about that too. Let's see what she can do."

Rob and Steve walk over to Tif bringing Izzy along to watch. By this time, Tif has the new guy completely hard and ready to go.

Rob says, "Sorry to interrupt Tif, but Izzy wants to see how you handle blowing multiple dicks at the same time. Alan, do you mind sharing Tif with us?"

Alan responds, "She is amazing. This ought to be good."

Tif smiles and motions for them all to stand in front of her. For the next 15 minutes, she expertly sucks one cock while stroking the other two. She really shocks them when she is able to deepthroat each guy while maintaining her dual stroking. Rob is the most surprised when Tif goes all the way around his thick meat.

Tif pulls off of Rob and looks at the guys and says, "Are any of you guys going to fuck me today or am I just sucking your loads out of you?"

Rob laughs and says, "Well, it depends on where you want our loads."

Tif replies, "I would love to feel your man meat pulse in my tight pussy. Are you willing to do that for me?"

They all nod in agreement.

Tif stands up and walks over to Izzy and says, "What are you interested in doing? You should get preference."

Izzy says, "I am nervous in a group this big. Can I just take one guy at a time and then send them to you?"

Tif says, "That is fine. But I want to talk to you away from these guys at some point and learn more about what you want and how to get you comfortable."

Izzy smiles and says, "Thank you Tif."

Tif looks back at the guys and says, "Rob, you are with Izzy. Steve and Alan, you are with me."

Tif sits Alan on a pool chair and leans over doggystyle to blow him. Steve walks up behind Tif and lines his erection up to her dripping wet pussy. Tif goes deep on Alan just as Steve starts to slide in. Both guys moan.

Izzy sits on a different pool chair and Rob follows her over. He says, "Tif really is something isn't she?"

Izzy looks over at Tif being split roasted and says, "Yeah. She is very talented and she seems very nice. I think I am going to ask her to teach me a thing or two."