Girl Posse Aspen Ski Trips Ends Pt. 07

Girl Posse Ski Aspen - Willow and Olivia

This story has been submitted for the " YAY TEAM 2025" challenge

Today's quotes to ponder are:

The best thing about skiing backwards is that you can see where you've been. ~ Warren Miller

The future ain't what it used to be. ~ Yogi Berra is a famous American sports philosopher known for his witticisms.

"The only reason I'd kick you out of bed is to fuck you on the floor." ~ Anonymous

When I call, the Posse comes. I'm Nikki Madison, and I'm the Girl Posse Leader. The Posse plays and parties together. This week, we have gathered in Aspen to ski and frolic in one of the world's most famous ski areas. Our week is winding down. The skiing has been terrific, and the sex has been even better.

We play by our own rules, and even then, there are not many rules. No means no, and an open door is an invitation to join. And the Posse shares. One would say we are all very good friends with benefits. And the Posse are independent women capable of making their own decisions and living by their consequences.

This story has been posted to Literotica. com with the full knowledge of the original author under my pen name, NikkijMaadison. No part or whole of this story may be reprinted in any other format or on any other website without the express written consent of the original author. I edited this story using Microsoft for spellchecking, flagging punctuation, grammar review, and as a dictionary. I use any other suggestions only as a guide. You may discover mistakes. That will happen.

© Copyright NikkijMaadison - All rights reserved.

This story contains sexual activities and situations between consenting adults. All characters are above the age of eighteen. Any similarity to any individual, living or deceased, or location is coincidental and unintended.

Each story will be told in the first person; however, there are eight days in our week, and eight women are members of the Aspen Posse. I am planning eight viewpoints - nine stories. Today's story will be told from Olivia's viewpoint.

The Posse Splits Up

There were no rules last night. Seeing how the Southern Boys adapted and truly lived their sexual fantasies. Seriously, what guy gets to bed an exotic dancer? And what guy to experience his first transwoman and his buddy got to live out his fantasy in real with two transwoman. You're not talking just one but two.

As Nikki and I walked downstairs, Clare was returning from dropping off the Southern boys at their hotel, while Harper was making breakfast. One by one, Heather, Bay, and Willow arrived, and soon the entire Posse was in the kitchen; no one was ready to ski. There was more talk about last night's sexual conquests than actual plans for the day.

We couldn't agree where to ski on our last full day, so we split up. Pepper and Clare were headed to Ajax; Willow and Harper wanted to go back to Highlands. Harper finally wanted to have lunch at Cloud Nine. Heather, Bay, Nikki, and I decided to ski Snowmass. So, we did.

But we did agree that all of us would meet for dinner at Bad Harriet's. Willow used her connections to get reservations.

Booty Watching

I, for one, love it when people watch me. I dress because it's who I am. I am all woman, and I dress for myself, and I love feeling and looking sexy; I love teasing guys and gals. Today, I am dressed in all red, tight, sleek ski pants and a matching parka.

But today I am one of four gorgeous, stunning women- two blondes and two brunettes - who have been gliding down the Elk Camp trails all morning. As we sped by other skiers, particularly men, they fell in line right behind us. And a woman can tell when someone is focused on her booty. Nikki is dressed in all black with fringe, Bay is in white with a blue stripe, and Heather is sporting an emerald jumpsuit.

We are four good girls who know precisely when to be bad, and we project just the right amount of trouble. We stopped for lunch atop Elk Camp, a lot of options. It's sunny, warm, and perfect. Of course, we were approached by more than one adoring man, but tonight it was the Posse's night out.

And when the Posse gathers, we all chat and compare notes about sex. Nikki is the common denominator; it's her Posse. We talked about who has or hasn't hooked up, and whether it was with another Posse member, alone, or with a stranger. In a way, we were setting up our potential future match-ups. It was an entertaining lunch conversation. Anyone eavesdropping was either shocked, amazed, or perhaps pondering how they could join in to share our pleasure.

We enjoyed a delightful afternoon of skiing. Finally, making it back to the Base Camp in Snowmass Village for a cocktail. We didn't stay long, then we went back to the chalet to get ready for dinner. Eight women are using five bathrooms. Never enough, but we managed. Tonight, everyone dressed warmly and stylishly, embracing the magic of the week and the evening.

Drink and Dine In Aspen Elegance

We took taxis over to the Hotel Jerome and nestled into a historic Aspen building. Bad Harriet's is the place where you go for the cocktails and stay for the fun. The Soiree is an experience in itself, a progressive collection of cocktails combined with a la carte menu. Even Clare and Nikki were impressed.

We were seated in a corner all by ourselves. We had room to spread out, with a bit of privacy. Other customers were noticing us but were pretty much secluded.

I spoke first, with a toast to everyone, "Cheers to Nikki for being our Posse Leader, and cheers to Willow and Harper for arranging for the exquisite chalet and all the bonuses that came with it!" Everyone raised their cocktail.

Then Heather added, "Cheers to the Posse. I've met some exciting and truly naughty women who know how to misbehave! To the Posse!"

Bay was quick to add, "And good friends for life!"

Pepper smirked, "Bay, make that friends with benefits!" And we all roared with laughter.

Our chatter was getting overly boisterous, so we tried to tone it down a little bit. Mind you, it isn't easy keeping eight women quiet.

Nikki stood and spoke, "This week has been quite the experience. We'll have to plan the next one soon. " She hesitated, and glancing at me, then Heather and Bay.

The week has been spontaneous, and today at lunch, the four of us enjoyed an eye-opening conversation that centered around Posse hook-ups." Everyone started to snicker, and I was certainly amused watching the facial expressions of each woman, as well as their subtle glances around the table.

Nikki quickly added, "I don't want to put anyone on the spot, but who have you hooked up with, and who have you wanted but haven't yet?" The Posee burst out into laughter. I saw a lot of finger-pointing.

Harper is not being bashful, "I will enjoy spending time with Bay! How about it, girlfriend?

Bay nodded and replied, "Absolutely, girlfriend!"

Clare spoke up next, " Let's go for it, Heather!" Heather exchanged seats with Bay to sit next to Clare, and Bay sat beside Harper.

Willoe looked at me, "Olivia, I've been looking at your fine ass all week, I want to lick your entire body!"

Pepper smiled at Nikki, "Babe, I've wanted you all to myself since meeting you in San Francisco. So, tonight's the night!"

So, the rest of us also switched seats. It wasn't musical chairs, since no one was left out. No one was disappointed; based on the chatter, everyone was ecstatic that we could pair up so easily.

Our server, Cassidy, whispered in Willow's ear, "Mr. Brooks has taken care of your tab tonight, and he was very generous to the staff."

Willow responded, "Wow, Ladies, we're all set, dinner is on my boss!" She removed a Franklin from her purse, tossing it into the middle of the table, adding, "Cassidy, here's some extra for the staff!" Every Posse member was just as generous.

Nikki stood again. "Ladies, let's misbehave. Our taxis are waiting!"

Back At The Chalet

It was a short ride to the chalet, and everyone hurried into the house

We were eight focused women. The Posse's last night together. Bay and Harper immediately went upstairs. Clare and Heather went to soak in the hot tub. Nikki and Pepper also hurried upstairs; they kept talking about who's cock was going where first. I'm still not positive who's kinkier.

Willow and I wanted to talk. She poured us both a cognac. We sat beside each other on the sofa and talked. We had met Nikki at different stages of her journey, and Nikki was the common bond between the two of us.

There was sexual tension building between the two of us, but neither of us was in a hurry. It was a mutual realization that we wanted to know each other better. So, we talked about ourselves. Initially we talked about Harper and Willow's relationship and how they clicked from the beginning. Willow told me that they planned to get married, perhaps in the Fall.

I asked her, "Why are you waiting until the Fall. It's too hot in Dallas during the summer, and we want Nikki to be able to attend. She was with us from the beginning, and when she moved to Dallas, we lived in her house, which is now our own." She hesitated, adding, "Nikki is very special to us!"

I remarked, "She is to me, too."

Willow spoke, "Olivia, is she your person?"

As a tear formed in my eye, I replied, "I think so, and I think she does too. We are still trying to mesh our lives and our lifestyles. I'm trying to decide my career path, and Nikki just started her new journey."

Willow sensed that I was slightly overwhelmed, moved closer to embrace me, and very tenderly brushed the wetness from my cheek. She leaned in closer, and we exchanged passionate kisses rather than just simple pecks on the cheek.

She whispered, "Olivia, I've learned that time with Nikki is precious. And I believe she thinks you are prized and valued too." I nestled my face against her neck, kissing her neck gently. I know she was sincere. Willow's life situation was similar to mine. But right now, I wanted to experience Willow's tenderness.

Willow softly cupped my chin, kissing me warmly, and I replied with more gentle kisses of my own. I felt my heart start to race, but there was no rush at all. I held her close, wrapping my arms around her waist while she snugly encircled my neck with her embrace. Willow softly drew my upper lip into her mouth, exhaling warm breath at the same time.

I turn my head slightly and gently kiss her lower lip. The heat between us intensifies. She releases my lip, and I release hers. Willow traces her tongue along the edge of my cheek, and I moan softly. She pulls back a bit. It's my turn; I gently peck my way to her right earlobe, kissing and licking the lower lobe. As I softly blow into her ear, I nibble on it. I can feel the warmth radiating from her body.

Being with Nikki is always tender and affectionate, yet in this moment, Willow captivates me.

Pushing back slightly, I move my hands up her body, gently placing them on her head and tilting it to the left. I softly run my fingers along her earlobe and then smoothly down her neck. I am not in a rush; I take my time.

I trace my fingers with gentle kisses and playful nibbles. Willow whimpers, and I break the silence, saying, "Willow, you smell wonderful; your skin is so soft!" Now, it's my turn to softly moan.

Willow removed her arms from around my neck and swiftly pulled on my beige cashmere sweater over my head, revealing my boobies encased in my black mid-cup underwired bra. She gently cupped the underside of my breasts and gently kissed my exposed skin, circling her tongue along the top of my exposed mounds. My body tingled.

I tenderly pulled her head up; we were eye to eye. She tilted her head to kiss me, wrapping her arms around my waist, and whispered, "My room or your room?"

Giggling, "The first empty bed! Tonight, Willow, you are all mine!"

She held me tightly; with her left hand, she reached up to hold the back of my neck, gently pushing my face back into hers. She gently pushed her tongue against mine. We kissed each other passionately.

I pushed back slightly, clasping her hand, and as we stood, I said, "Babe, let's go!" We scurried up the stairs. I left my sweater on the sofa. At the top of the stairs, we could hear indistinguishable moans and whimpers mixed with screams coming from the other bedrooms. We quickly ducked into my bedroom.

Once inside, I gently pressed Willow's body against the interior wall, and we kissed. She was so sexy in her embroidered bustier. I rested my hands on her booty, and my fingers roamed her clothed lower body.

Willow placed both hands and arms around my neck, pushing my face into hers... again. We kissed. Willow tenderly parted my lips with her tongue. We kept kissing passionately. I held her tighter.

As she pressed her body into me. Willow said, "Olivia, I have wanted you since the first time I met you. I can't believe this is happening now."

Time To Get Naked!

Our lust quickly turned to heat. Our chests push against each other. The feel of her body against mine sent shivers down my body. I felt her warmth; she was the flame. Her hands drop down to my hips; Willow is still fully clothed. Willow breaks our kiss. "Let's get naked!"

And we did, hastily wiggling out of our jeans; Willow kept her bustier on but removed her G-string, revealing a little heart patch just above her pussy lips. I was having difficulty squirming out . of my skinny jeans, and I sat on the bed. Willow dropped to her knees to help, hastily tugging on my jeans down my legs and ankles.

She slid up my lower torso and, in one fluid motion, pulled my black G-string down my naked leg, spreading my legs slightly, fully exposing my shaved pussy. Willow was beaming as her head disappeared between my legs, planting a soft, warm kiss on my pussy. I gasped and instinctively opened my legs wider; her warm lips felt wonderful. I was relishing in the sensation of Willow' tongue stimulating my pussy.

My head was spinning; I was whimpering excitedly. Willow gripped my thighs, spreading my legs even wider. She kissed me again, gently sliding one finger, then two, into me, whispering, "Olivia, you are so wet."

I breathlessly gasped as she parted my labia lips. Willow pressed her face tight to my sex, twirling her inviting tongue the length of my pussy, spreading my pussy lips she licked, then curled her tongue back and forth. One whimper was followed by another and then another. Her tongue had me on the edge. Either she taught Nikki, or Nikki taught her.

My fingers were vigorously rubbing my mons. Willow replaced my fingers with her tongue, flicking it with the tip. My whimpers became steadier, and I softly whispered, "More, more Willow! Don't stop!"

Willow Took Me to the Edge

As her tongue delicately danced over my clit, I felt her finger slide deeper into me, squirming as her penetrating fingers went deeper, pressing on my G-spot. I fell back on the bed, flopping my head back on the bed covers in bliss. I tried to reach Willow, but my arms and hands were aimlessly flapping. I arched my back as a wave of intense pleasure broke over me.

Willow' senses told her that I was ready, so she pressed her face down on my pussy. I thrashed about, moaning uncontrollably, and my body was tingling with overwhelming desire. Only Nikki has taken me to this plateau.

Willow had ignited the flame within my body with her fingers and tongue. The warmth was spreading like a wildfire of pleasure through my entire body. I continued shaking. My legs were weak. I bit my lip to quiet my screams of utmost joy. I didn't want this pleasure to end. Willow whispered, "Olivia, I want to hear you scream!" I was on the edge of the cliff. She was now sucking my clit into her mouth.

She removed her fingers from my pussy, forcibly sliding her wet and lubed finger into my puckered hole. I was now flamed in ecstasy. My moans were now screams, 'Oh, Oh, Oh yes!" I could no longer be quiet. I was on the brink; it was time for Willow to push me into bliss. I clutched the bed covers, twisted and squirmed, curled my toes, and surrendered my body to Willow. My body was now calm.

Willow crawled onto the bed, cuddling in beside me. We kissed gently. I whispered, "You are delightful!" Willow responded by kissing me gently while holding my chin. We exchanged soft, gentle kisses. We became silent in our thoughts. Willow wiggled out of her bustier, and as we held each other tightly, we drifted off, not into a deep sleep but instead into exhaustion.

Suddenly ...

I awoke abruptly. A warm smile crossed my face. I instantly remembered the pleasure I had just shared with Willow. I was indeed happy. We were not under the bed covers, and I could feel a slight chill, so I pulled Willow in tighter. I could feel the heat of Willow's warm body against mine. I loved the feel of her body. It felt very natural. Her hips snugly fit against my body.

Willow, with her eyes closed, her head lay quietly on my chest, and our naked bodies were intertwined. Her breasts rose and fell against my own, silently breathing heavily. At that very moment, I felt incredibly content, but I needed more of this lovely creature.

I softly ran my fingers, delicately tracing her ear lobe, then smoothly down her neck. I softly pecked at her visible earlobe, gently kissing and licking the lower lobe. I nibble on her ear, and with soft bursts, I gently blow into her ear. I am holding her body tight against me, and I feel her body twist. I don't want to wake her, so I gently nibbled on her exposed neck.

Willow unconsciously tightens her arms around my waist. Her left eye opens slightly. She's smiling; I smile back, lowering my head to kiss her. Turning my head slightly, I gently suck on her upper lip, blowing warm air at the same time. I let go of her lip. I can feel the heat building between us. It feels good.

I tenderly pulled on Willow's body, so we were lying on our sides, face to face. She tightly wrapped her arms around me, pressing us closer. We kissed passionately. My hand cupped the underside of her breast, gently caressing her perky mound. My fingers discovered her nipple, and I gently rubbed the now-hardening nipple with my thumb and finger. Willow tenderly released more soft whimpers. I whispered, "Relax, sweetie, I can't get enough of you."

My fingers were exploring her perky boobies, gently caressing her bare skin. I could feel Willow's body tighten to my touch. With my mouth and tongue, I explored her neck, her shoulders, and her breasts. I was mesmerized by Willow's soft, smooth dancer's body.

Positioning my frame in front of Willow, I straddled her; my chest was dangling over Willow's body and with two fingers on each boob, she playfully tweaked my nipples. I lowered my body into her face, and her tongue found my left nipple; as she twirled her tongue around my areola, it was my turn to whimper repeatedly.

Moving down her torso, she gradually fell flat on the bed, slightly propping her legs and knees. As my hand tenderly explored further down her flat stomach, Willow lifted her legs, spreading them slightly, and gave me free access to her sex. Her nearly bare pussy was glistening. I could feel her wetness. My fingers gently caressed her mons; her clitoris hardened to my touch, and the frequency of her whimpers increased quickly.

Blowing warm air, I brushed my mouth across her outer lips; using my tongue, I easily parted her labia, giving me the taste of her sweet pussy for the first time. It was delicious. As I pushed my tongue further inside her sweetness, I wanted more, running my tongue the length of her luscious lips to her clit. Willow's body jumped at the shockwave created by my swooshing tongue. To ease her sensations, I kissed her softly on her smooth skin.

Willow's body was glistening, trembling in tune with each gentle kiss. Willow squirmed as my tongue and mouth explored every inch of her inner thighs. To hold her still, I gently held the sides of her thighs, pulling her legs even wider. Pressing my face and mouth closer, my tongue licked and twirled around her swollen clitoris. Willow was on the edge; her breathing was heavier, and more moans followed her moans.

Her lower body squirmed and twisted; I increased my tongue movements on her mound. Then she screamed, "Oh, Oh, Oh!" followed by a second wave, "Oh, Oh, Oh!" Her body was pulsating, and fluid flowed. I eagerly lapped up all I could. I buried my head between her thighs. I, too, was close, but at the moment, this was all about Willow's pleasure.

Willow pulled my body up to lie next to her; We embraced, and Willow kissed me, "Thank you, Olivia, hold me!" We managed to get under the covers. I snuggled in behind her. We fell asleep with me holding her tightly. Her booty was nestled in my crotch. I don't remember either of us removing our makeup.

The Morning Sun Was Shining

The morning sunlight drifted into the room. Willow was still lying next to me. I peered over to read the bedside clock. It was nearly 8 o'clock. It was departure day. I gently caressed Willow's naked shoulder. And as she opened her eyes, she smiled.

I spoke, "Good morning, Sunshine!"

She replied, "Good morning. It was amazing last night. So amazing that Nikki has no choice but to bring you to Dallas to celebrate with me and Harper!" We kissed.

She paused, then added, "What time is your flight departure?"

I replied, "I think it's around ten!"

Willow gave me a slight frown, adding, "That's sad, our encore will be in Dallas then!" We kissed again.

Reluctantly, she left my bed to return to her room to find Harper. I fell onto the bed and closed my eyes. The taste of Willow was a perfect way to end this wonderful week in Aspen.

To be continued in the 'Girl Posse Departs Aspen'

This story has been submitted for the "YAY TEAM 2025" challenge. The Girl Posse is my Team!

"Dream the impossible, seek the unknown, achieve greatness!" ~ Author Unknown

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