The Anniversary Vacation Ch. 06

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Tom, Kenzie and Aunt Anne try something new.
5.2k words
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Part 7 of the 12 part series

Updated 06/08/2023
Created 08/10/2017
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If you have ideas for something you want to see comment or message me and I'll see if there is a way to work it in. All characters are 18 and up.

Hope you Enjoy!

*

I wake up to weak sunlight coming through the blinds covering the sliding glass door. I rub the sleepiness from my eyes and see Kenzie still asleep. I wonder what time she finally fell asleep. She was so worried about Aunt Anne yesterday; I wonder as I lay in the bed. I roll around for a few more minutes, before falling back asleep, wondering what today would hold.

I wake up for real several hours later. Kenzie is already awake and walking around the room in a bra and panties. "Your finally awake?" She asks me. I nod and yawn. Kenzie gives me a look of almost pure panic, "Good, Aunt Anne is going to be here. They wanted us over there as soon as possible."

"Hold up! They say why?" I ask, still confused from my sleepy state.

"No. I'm just worried that it might be... weird..." Kenzie says.

"Give me a second." I say throwing the covers off, reveling I'm only wearing my boxers. I quickly dress in gym shorts and a shirt, similar to what Kenzie put on. I brush my teeth then emerge from the bathroom ready for the day.

As we make the short trim to our parent's room I look at Kenzie and say, "Whatever happens today... I don't want it to change what we have going."

Kenzie gives me a smile, "Same here. I love you."

I smile back at her, "I love you too." Then I knock on the door. Almost instantly, Dad opens the door and ushers us inside. Mom is inside dressed in jean shorts that barely cover her ass and a crop top that barely hides her breasts.

"Good to see you two." Mom says, looking up.

Kenzie and I both stare for a second before I say, "Good to see you too."

"You guys nervous?" Mom asks. Kenzie and I both shake our head.

Dad stands behind Mom and puts his hand on her shoulder, "Good! Anne is really fun and once you get to know her... well you'll see."

After several minutes, there is a knock on the door. "I'll get it!" Mom says, standing and walking to the door. She looks through the peephole, bending over slightly so her shorts ride up and the bottom of her ass is exposed. Mom then opens the door and stands back as Aunt Anne who is slightly shorter than Mom walks inside. Aunt Anne has smaller breasts than Mom, probably being about a C cup. She is 40 years old and has a suitcase in one hand. She is wearing a very similar outfit as Mom is, her body fairly exposed to the air. Anne and Mom hug for a second before pulling apart. Anne turns and upon seeing us, she smiles.

Walking over to Dad first, she hugs him and in a voice similar to Mom says, "Long time no see."

Dad hugs her, giving her a kiss on the lips. "Oh trust me... it was memorable."

"Oh yes it was..." Aunt Anne says before turning to Kenzie and I. She pulls me in first and says, "You grew so much! You're a very handsome young man!"

"Thanks!" I say returning the hug.

Aunt Anne then turns to Kenzie and hugs her as well. Kenzie returns the hug and smiles at Aunt Anne. After the two of them pull apart Mom asks, "So who's room do you want to stay in?"

Anne thinks for a second then answers, "Tom and Kenzie. Do you guys mind if I stay with the two of you?"

I smile, "Go ahead. Want us to help you bring your stuff over."

Aunt Anne gives me a smile back, "Yes please. We'll be right back!" She calls to Mom and Dad as her and I walk out. "Which room is yours?" She asks, when she's alone with Kenzie and I in the hall.

"This one, 212." I say, opening the door. Aunt Anne leads the way and I follow, examining her from behind. My aunt's ass was the same sizes as Mom's. From the short time I had seen her, so far she didn't seem so bad.

After I close the door behind us Anne asks, "So... how have you been? I haven't seen you in years!"

I set her suitcase down on the cabinet, next to Kenzie's. I say, "It has been a really long time..."

"What are you and Kenzie up to these days?" She asks.

"I'm in business school, and Kenzie is going to be a nurse." I answer.

"That's great! I'm just enjoying life and its many pleasures. Speaking of that... how are you enjoying this resort?"

"It's been... interesting." I say, not really sure how to answer the question.

"In a good way?" Aunt Anne asks.

"I guess... I've learned a lot about Mom and Dad's lifestyle." I answer.

Anne smiles, "And from what your Dad told me a fair amount about Kenzie as well!"

I go red, "How do you know?"

Aunt Anne just smiles, "It doesn't matter, the only thing that does is if the two of you enjoy it. Your Mom and I used to do something similar. It started innocent enough but over time..." She trails off, a smile on her face. I hear a knock on the door. Looking through the peephole, I see Mom standing there, dressed for the beach.

I open the door, "Yes?"

Mom says, "Your father and I are heading down to the beach now and I think Kenzie will be down shortly after if you two want to join. If not, just... have fun."

I nod, "Thanks for the heads up." Then I close the door. When I turn back, Aunt Anne is looking at me expectantly. I say, "Mom and Dad are going down to the beach and we can join them if we want. Kenzie is probably going down in a bit as well."

Anne smiles, "I'm sure that would be really fun! But I just got here and still need to unpack. If you help me it will only take a little bit..."

"I guess it wouldn't hurt." I say, stepping forward to help. Aunt Anne opens her suitcase and begins to dig through it, handing me a smaller black bag with several bottles inside.

"Set that off to the side, it's for later." She tells me. I set it down on the table in the middle of the room. After several smaller bags, Aunt Anne is finally unpacked. She looks at me and asks, "The beach requires the people to be completely naked right?"

I nod and say, "Yes."

She makes a hhhmmmm noise and looks back into her suitcase. "Can you help me pick out something to wear down there? I don't want to look tasteless."

"If you want me to." I answer, wondering where this is going.

Aunt Anne smiles at me before pulling out some clothes. She takes her hand and drops her shorts, revealing that she is not wearing any panties as well as her large meaty inner lips and completely bald pussy. Then she pulls her crop top over her head, reveling her still firm breasts and small pink nipples, both of which are pierced with a bar going through both of them.

I look away as I feel my cock begin to become hard, hopefully not visibly so. Aunt Anne sees me and laughs, "What's wrong Tom? You've had sex with your mom and sister but don't want to see me naked?"

"It's not that..." I start.

Aunt Anne cuts me off, "Or is it because you think Kenzie might get jealous? Because let me tell you, I'm sure the three of us can work something out later."

Seeing her gesture around, causing her tits to sway around makes me hard, my cock clearly visible to her. I stammer, "It's... ummm..."

Aunt Anne looks down and sees my hard cock poking into my shorts and smiles. "Well, I guess your clearly not disgusted. Unfortunately for you, it's not polite to have an erection at a nude beach so we just have to wait for it to go away."

I snort and jokingly ask, "And I'm guessing you have the solution?"

Aunt Anne smiles at me, "Wise ass. I actually do if you get over here we can make this a quickie." I cross the room and drop my shorts and boxers in one motion. Aunt Anne lies back on the bed that Kenzie and I have been sharing for the past several days. I run a finger over her sex while I bring my lips to hers. Aunt Anne and I explore each other's mouths for the first time. I insert one finger inside her, feeling that she is already wet. I continue to kiss her as well as teasing her pussy with my fingers.

After several more seconds she says, "Stop teasing and fuck me!" I smile at her and reach for my cock, sliding it directly inside her. "Mmmmmhhhhh, that's it!" Aunt Anne sighs as she takes my whole length on the first thrust. Her moist pussy grips my cock and squeezes it as she works her muscles. I slowly slide in and out of her for a few more thrusts, each one causing my aunt to groan in pleasure. She pulls me close to her and I feel her hot breath on my ear, her moans filling the room. Down by my chest I feel her soft breasts pushing into me, topped by the cold metal of her nipple piercings. After several more seconds of this Aunt Anne pulls away and looks at me with pleading eyes, "Fuck me faster!"

"Really?" I ask, enjoying the feeling of filling her pussy with my cock and taking my time.

Aunt Anne nods gasping out, "Yes... we need to meet... up with the... others..." I nod and pick up my pace so I'm slamming in and out of her pussy, the sound of skin slapping on skin mixes in the air with her moans. I feel her pussy begin to contract as she cries out in orgasm, her juices being forced from between her meaty lips by my cock. I feel my own orgasm build and continue to slide in and out of her dripping pussy. I slide inside her warm pussy as far as I can release my cum, feeling my hot load mix with her own cum deep inside her.

I slide my cock out of my aunt who lays back on the bed and sighs, reaching a finger down into her dripping slit. My cum begins to slowly drool out of her as she touches herself. "Something wrong?" I ask, concerned.

"Well... you had no way of knowing this but I really hate having cum in my pussy. I just don't like the feeling." Aunt Anne says.

Fuck! I think before saying, "So..."

Aunt Anne sighs, "Let me go clean this up quick and we can talk then." She stands and makes her way into the bathroom, closing the door behind her. Hopefully she's not angry at me I think. After a minute, she returns and passes by me for her suitcase, picking her clothes up off of the bed. She rummages through her suitcase for a second while I stand there in silence.

"I'm sorry." I say, wanting to clear the air.

Aunt Anne sighs, "It's fine. I should have told you." She then pulls out a white pullover kind of dress. She slips it over her shoulders and it covers her ass, just barely though. She turns to face me and I can see the metal bars on her nipples pushing through the thin material. "For next time I like cum in my ass." She says with a joking smile.

"Really?" I ask, having never done anal before.

She laughs, "You'll just have to wait until later to find out. Now let's go. I'm sure everyone else is wondering where we went." With that, she leads the way out of the room and I follow. We make our way downstairs and out of the hotel. Walking down the stairs, I can see why she chose this outfit. The bright sunlight makes it practically see through, allowing me to see the outline of her breasts and nipples as well as her shapely ass through the material.

"I like what your wearing." I say with a smile.

Aunt Anne smiles back, "Well we are going to a nude beach so it's not like it matters too much." We reach the beach and begin crossing it, heading to where she saw Mom, Dad and Kenzie. After a minute we get there and we both undress. Kenzie watches me, with a look that makes me think she has a very good idea what happened.

After Aunt Anne and I are both naked, Kenzie stands and whispers to me, "Let's take a walk."

I nod in response and she and I begin to make our way up the beach. After we are out of earshot of Mom, Dad and Aunt Anne, Kenzie asks, "So did you and Aunt Anne... do anything?"

I sigh, "Yes... we had sex. Why?"

Kenzie frowns, "I just don't like where this whole thing is going. I liked when it was just me and you at the beginning. When Mom joined in that one time it was fun for me because I had never done anything with a girl before. Now with Aunt Anne here..."

"You feel jealous?" I ask.

Kenzie nods. We continue to walk up the beach for another few minutes in silence, both lost in thoughts. Finally, I say, "I'm sorry you feel that way. The thing is... you're my sister. How much longer is this really going to last?"

Kenzie gives me a funny look, "You mean after we go back home?"

I nod, "Yeah... This whole thing between you and me is great and you're really fun. But we go to different schools and only really see each other on breaks."

Kenzie sighs, "That's a problem for later. Right now we can be together and for the rest of summer at home we can be together. After that... it's an issue for the future. Besides we have Aunt Anne as the current... potential problem."

I ask, "What do you mean potential problem?"

"Remember what Mom said about her probably wanting to get both of us involved..." Kenzie asks

"Yeah." I answer.

"Well... I'm worried about what she's going to want to do with me. What if she wants me to try anal, or brought dildos to use on me or something?" Kenzie says with worry in her voice.

I laugh, "Well, I'm pretty sure she's into anal, but not giving it."

Kenzie gives me a dirty look, "What do you mean?"

I sigh and say, "Well earlier when she and I were... alone, I came inside her pussy and she wasn't really happy. She told me she hates the feeling and prefers it in her ass."

Kenzie raises an eyebrow and looks at me, "Honestly?"

I smile, "I swear to god!"

Kenzie lets out a relieved sigh, "That's good. I tried using a butt plug back at home once and... well... I didn't enjoy it."

"Really? You have your own toys at home?" I ask.

Kenzie smiles, "Of course! A girl has to have a way to take care of business. I would just wait for the house to be empty."

We reach the end of the beach and Kenzie turns around and we slowly begin making our way back to our parents and Aunt Anne. On the walk back I ask, "So that first night... what made you want to masturbate together?"

Kenzie walks several more steps before answering, "I thought about doing something like that for a while..."

I smile at her, "Really? How long?"

Kenzie nods, "Really. For a few years. At first, I thought it was just a phase but after a long time of being interested it didn't go away. Were you into me at any point before this?"

It's my turn to take several steps in silence. Finally, I say, "Honestly... I knew you were beautiful and you have a killer body." Kenzie smiles at this, jokingly elbowing my arm for looking her naked body up and down. Her tan ass sways as she walks and her breasts jiggle slightly with each step she takes.

"So did you think about me sexually?" Kenzie asks.

"At several points... yes." I answer, making Kenzie smile.

We walk the rest of the way back to our family in silence, enjoying each other's company. When we get back to the beach chairs, Mom asks, "You two go in the water?"

"No, we just took a walk." I answer.

Mom nods, "Your father and I are going to head down to the water now."

Mom stands and Dad follows suit, the two of them holding hands and walking into the ocean, leaving Kenzie, Aunt Anne and I together on the beach.

Aunt Anne waits a second before asking, "This might be a little forward but... Kenzie, what do you think of your Mom?"

Kenzie looks confused for several seconds, before asking, "What do you mean?"

Aunt Anne smiles, "Do you love her? More than most daughters do?"

Kenzie raises one of her eyebrows, "Like sexually?" Aunt Anne nods. Kenzie sighs, "Well there was the one time with her, Tom and I."

Aunt Anne smiles, "Well? Was she good?"

Kenzie shrugs, clearly a little embarrassed by this conversation, "I'm not sure. She's the only woman I've ever been with."

Aunt Anne nods, like she was expecting this answer, "Want to change that?"

Kenzie looks slightly worried, "Like right here? Right now?"

Aunt Anne laughs, "No... later. When we get back to the room."

Kenzie thinks before answering, "Maybe..."

Aunt Anne gives her a teasing smile, "Oh don't be like that! Tom and I already had some... fun. Didn't we?"

Kenzie gives me a funny look. I say, "Yeah, we did."

Aunt Anne sighs, as she sees Mom and Dad walking back toward us, "Well you have plenty of time to decide." The rest of the day passes quickly for me, as I hope to see Kenzie once again get with another woman. Finally, all five of us pack up to head back to the rooms at about 6 pm. On the short walk to the hotel, Mom asks, "Tom, Anne and Kenzie will your Dad and I see you later or will you be doing your own thing?"

Aunt Anne looks at Kenzie and I to answer Mom. Before I can say anything, Kenzie says, "You two have fun... just you know... don't get pregnant Mom!"

Mom laughs, "I wasn't planning on it! You guys have fun, see you tomorrow."

We all say good night to Mom and Dad, before we walk back to our room. Once we enter room 212, Aunt Anne smiles at Kenzie, "We're going to have a lot of fun. Right now... I'm going to freshen up before this goes any further."

Kenzie smiles back, but doesn't say anything. Once Aunt Anne goes into the bathroom and closes the door, I ask Kenzie, "What made you decide to do this?"

Kenzie gives me a smile, "I really enjoyed the time with Mom and... well Anne is her sister so..."

I smile, "God, it's so hot to see you opening up like this."

Kenzie gives me a smile and quick kiss on the lips, before stroking my slowly hardening cock through my shorts. After several minutes, Aunt Anne comes out of the bathroom smiling. "So... what do you guys want to do first?" She asks.

Kenzie and I both think for a second, as Aunt Anne tosses her white cover up over her shoulders, revealing her naked body to both Kenzie and I. Kenzie asks, "Ummm... how do those feel?"

Aunt Anne laughs, "Well I really like my nipples being played with so I figured why not. What about you Kenzie? You like your nipples played with?"

Kenzie smiles, "I do."

Aunt Anne nods, looking at Kenzie, "Well... you going to make me be the only naked girl here?"

Kenzie shakes her head and begins to unbutton her shirt, allowing her firm breasts to spill out. Leaving the top on, but having it open starts to make me hard. Aunt Anne looks at Kenzie with a look of lust, as she clearly undresses my sister with her eyes. Kenzie then teasingly drops her shorts, showing off her shaven mound.

Aunt Anne smiles at Kenzie and steps toward her, "You have such a sexy young body."

Kenzie smiles back, "Thanks." She closes the distance between herself and Aunt Anne. Kenzie is several inches taller than Anne, and the two of them begin to kiss. They start with just lips, but it quickly evolves into swapping tongues and clearly enjoying the feel of each other's bodies. Kenzie's hands begin to wander down to Aunt Anne's pierced nipples first, feeling them and pinching slightly at them.

Aunt Anne pulls away from Kenzie and smiles, "You sure know how to get a woman worked up!" Aunt Anne then begins pinching and sucking on Kenzie's nipples, while our Aunt's hands start feeling Kenzie's ass and pussy. Kenzie lets out a gasp as Aunt Anne runs a single finger over Kenzie's sex.

"Kenzie your soaking wet already!" Anne says, pulling her finger away from Kenzie's mound.

Kenzie smiles, "Well after Mom and I... had our fun... I found I'm pretty open to the idea of sex with other women."

Aunt Anne pulls away from Kenzie, "Want to try something?" She asks.

Kenzie shrugs, causing her breasts to bounce up and down. "Depends on what it is."

Aunt Anne pulls out the smaller bag she handed me earlier, opens it up and produces several bottles of lube. "These are for you. Trust me when I say it makes anal easy and fun." Kenzie frowns and Aunt Anne asks, "What's wrong Kenzie? Don't like anal?"

Kenzie shakes her head, "I don't know. I've never done it."

"Would you be open to it?" Aunt Anne asks.

Kenzie nods, "It's something I think about when I masturbate. I've wanted to try it for a while."

Aunt Anne smiles, "Want to try it tonight?" Kenzie nods. Aunt Anne continues, "Come into the bathroom with me then. We've got a little preparation to do!" Kenzie tosses her top to the side and makes her way into the bathroom and Aunt Anne grabs another smaller bag from her suitcase. She turns and looks at me before going into the bathroom, "Tom, we'll be out in a little bit."

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