The Ski Bunny Ch. 07

Story Info
Word of Will's expertise spreads to more of Anna's friends
9.8k words
4.59
45.6k
18

Part 7 of the 7 part series

Updated 10/27/2022
Created 10/02/2011
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Thank you to everyone who read any of my previous stories, especially to those who give me feedback and voted them so high! If you haven't read them yet, I recommend doing that first. You won't regret it!

I apologize for the delay of 7+ months, but real life got busy, and I wasn't sure how to end the saga. I came up with a two-part ending that I hope you enjoy. The last chapter--whenever I get a chance to finish it--will likely appear back in the Erotic Couplings category. Either way, if you like them, please vote and leave comments. If you don't like them, then poo on you!

*

Sunday nights are never something I looked forward to. As far back as middle school they were depressing because another fun weekend was ending, there was homework to do, and I was anticipating another week of weathering the heartless jungle that was junior high. It was better now that I was 30 and had established myself in the "real world" for which school was supposed to prepare me. Still, I would rather stay up late with my girlfriend Sherry--talking, cuddling, humping, knowing we could sleep in the next morning--than to have to think about my boring insurance auditing job that awaited my arrival in twelve hours.

My phone chimed: A text message from Sherry. "Hey lover! You up?"

"Hi hotness!" I replied. "How's Denver?"

It was mid July and my air conditioner was struggling to keep up. I kicked back on my recliner and brought up the on-screen menu and scrolled through over a hundred channels, looking for something I might want to watch. Nothing. Like that old Springsteen song, "57 Channels and Nothing On," except now it's 570 channels. I ultimately settled on a documentary about the USS Ronald Regan, but I wasn't really paying attention. I considered checking out some of the premium movie channels to catch some soft-core porn. But I decided against it with a big smile: I don't need porn, I thought. I'm getting as much tail as I can handle this summer.

"Not bad," Sherry texted back. "Miss you."

"Me too."

The improbable events that brought me to that decision played out in my mind like a movie I've watched too many times: I met a gorgeous blonde at a ski resort. She had big tits and a great ass, but also girl-next-door beauty and accessibility. Her quick wit and dry humor were matched by me. Sherry and I did the four-legged frolic, first in a gondola, then at her condo. In between she revealed that she is four years older than me and well financed. After we got back home, our sex-crazed relationship quickly evolved into a beautiful meeting of the minds and bodies, and as we relished our astounding adventures in carnal knowledge, we began to fall for each other in a more meaningful way.

"When you coming home?" I asked her.

"Might be another week."

I replied with a sad face emoticon. Sherry had only been gone two days, but we had never been apart for a week since we first met. I suppose I had been lucky so far, since travel was normally part of her job as an executive at her small advertising agency. I sent a follow-up text: "???"

"Potential client in Seattle. Flying there tomorrow morning."

"Hurry back. Balls already blue. ;) "

"Call Anna."

Turns out Sherry had a smokin' hot eighteen-year-old daughter: a cheerleader named Anna. She was a younger and even hotter version of her mother, so it wasn't hard for her to seduce me into doing the horizontal hustle with her. In a stroke of pure brilliance, she convinced her mom that a sex triangle was beneficial to everyone. She was going to start having sex again anyway, so it might as well be someone trustworthy, someone with whom she shared a mutual attraction: me. Sherry wanted to see both me and her daughter happy, so she agreed to share me, at least for the summer. Suddenly, the most improbable but erotically tantalizing arrangement was in effect, and keeping these women satisfied kept me and my dick as busy as I could imagine.

"You mean booty call her?" I texted.

"You know she'll be up for it."

"True dat."

I had counted my blessings several times. I am neither remarkably good-looking nor smooth with the ladies. I'm an average 30-year-old, but I do like to keep in shape. Both Sherry and Anna have complimented me on my body. I also have a slightly larger than average package when fully erect, and I'd say I'm better than average when it comes to using it. Perhaps that's why I ended up getting more business: customer referral.

"Seen her lately?" Sherry texted.

"Not last week. Been hanging out w friends a lot."

By "friends" I meant her best friend, Hailey. My summer of love got even wilder when Anna introduced me to the brunette volleyball star who was jonesing for an experienced Don Juan to tickle her belly from the inside. It had been about an month since I had first experienced Hailey's smooth, tanned nakedness, headlined by her round but tight bubble butt. Since then, I had been living the dream: dating the most incredible woman I've ever met, keeping her gorgeous daughter satisfied, and dabbling in the humpty dumpty dance with her sex-crazed friend. It was enough to keep me so busy that I rarely got a chance to hang out with my friends. They understood at first, but their patience was wearing thin. I needed to stay connected to the real world.

"Have fun," Sherry texted. "But behave!"

"Only when I'm not with you."

I also had a bigger problem. After my first three-way with the barely-legal duo, Anna had promised that she would find a way to make this acceptable to her mother. She knew Sherry was my main lover, and she had orchestrated our prior arrangement, but taking it one step further proved more difficult than she had anticipated. As the summer progressed and Hailey's visits to my house became more common (sometimes with Anna, sometimes without) I found myself needing to hide from Sherry the fact that I even knew Hailey. That made me feel guilty. I was all but ready to profess my undying love for Sherry, and while she had given a temporary stamp of approval to regularly bang her daughter, a second teenage girl was not part of the agreement.

"We should talk when I get home."

Uh oh. "Let's talk now," I bravely texted back.

"Can't -- at a dinner w client."

"Bad girl!"

Don't get me wrong; Getting it on with Hailey was pure erotic bliss. She was a tiger who became increasingly aggressive with each encounter. She sometimes engaged us in role-play, the most recent being a flight attendant and a business traveler joining the mile-high club in the airplane lavatory. (My hall closet still retains the faint tell tale odor of her juices.) Every minute of our adult playtime was fantasy fulfillment, especially when Anna was with us.

And did I mention how much I relished having sex with Anna? I had a bit more history with her, so it was easy for her to stand out as the preferred teen sex kitten. We couldn't keep our hands off each other, and each roll through the hay was so thrilling that I tried to savor and remember every moment of it. It seemed all I wanted sometimes was the sight of her naked perfectness, and the feel of my rock-hard cock rubbing away at the inside of her pussy.

At the same time, I couldn't help but notice that sex with these two hotties seemed to be slightly muted by the worries hanging over my head. Was I jeopardizing my relationship with Sherry? Not only was I was hiding something important from her, but could these teenage distractions cause me to love Sherry less?

Wait, I thought to myself. Did I just say "love"? It wasn't the first time it had crossed my mind: the possibility of truly being in love with Sherry. But it was the first time I actually felt something when I thought it. I couldn't deny the fact that sex with Sherry was more enjoyable. It carried something deeper with it, an emotional connection that couldn't be matched by two recent high school graduates.

"Yup I'm your bad girl!" Sherry texted back. "Just remember that."

I could feel a slight change in the way Sherry had been behaving in the past couple weeks. It wasn't anything I could put my finger on as a definitive Exhibit A, but she seemed a bit more distant and less energetic. Our lovemaking was still passionate and satisfying. A nine out of ten is still outstanding, but had always a ten with Sherry until recently. I sensed something was a bit off. I began to wonder if she was jealous of her daughter and ready to cancel our arrangement, or if she had sniffed a hint of what I was doing with Hailey. I could deal with the former, but the latter would spell trouble for our relationship, and it would be completely my fault.

* * * * * * * * * *

"So how are things going with Sherry?" Russ asked over the din of our surroundings. "And Anna? And...Hannah? No, what's her name?"

"Hailey," I corrected. The table at our booth wobbled on uneven legs. Its veneer was heavily scarred from years of drunken abuse. It was par for the course at the Wall Nutt, a dirty little watering hole for which we were fully overdressed.

"Lucky bastard," said Sean, the most cynical of my friends. "I'm still not sure I believe you one hundred percent."

"Shut up, Sean. Let us live vicariously through him," said Russ. "If it's made up, I don't wanna know."

"You wanna be Manti Te'o before the shit hit the fan?" asked Gene.

Sean half laughed and half sighed, then looked at his phone. A text message had just buzzed in.

"That Mantra?" I asked.

"Yep. Fifteen minutes. Let's close out and start walking."

"I'll get this round," I offered to my friends.

"Damn straight, you will," Russ said. "You owe us one, if only because of all the tail you're getting and we're not."

"Speak for yourself," piped up Gene, the only married one among us.

"Shut the fuck up," countered Russ. "You know it's not the same." He turned back to me and pressed for more details on new adventures with my girls.

"First of all, Sherry's still out of town. Some new client in Seattle," I explained.

"So that means Tinkerbelle and the Cheerleader are keeping you company?" asked Russ.

"And then some," I said. My friends all had their eyes locked on me, waiting for more. "Lemme get the tab first," I said. "Then we'll walk and talk."

I didn't tell them the real reason why I offered to pay our tab: I wanted to cross paths with a beautiful redhead I spotted from our table. She sat at the bar with a couple female friends to her right, easily outshining them both. I squeezed my way in between her and another bar patron. While I waited for the bartender to return my credit card, our eyes met.

I was enamored immediately. I was looking at true beauty, a mermaid with legs. Her big, deep green eyes shone right into me, and for an instant I felt like she could read my thoughts. Her wavy, shoulder-length hair was the perfect shade of red, a la Emma Stone. A pair of dangly silver earrings glimmered in the faint light of the dingy bar. They complimented her bracelets and her smile, which absolutely lit up the room.

Her outfit shouted classy sex appeal: She wore a tight, sheer turtleneck in ivory white that did nothing to hide the size of her chest. Her maroon pleated skirt matched the color of her hair. It reached halfway down her thighs and fell gracefully around the barstool where she was sitting. A pair of high-heeled, knee-high leather boots completed the ensemble. They emphasized the muscle tone in her legs and butt and made a rather tantalizing view of the eight inches of exposed skin on her leg. Anna could have worn this outfit and made it look just as sexy, if not more.

"You're dressed up for something better than a junky place like this," I said to her. I expected her to return the compliment.

"Yes, remind me to never become part-owner," she quipped. "Excuse me." The mermaid turned away and walked with her friends, right out the front door.

Ouch.

Well that went well, you douchebag! I scolded myself as I walked away with my receipt.

Yeah, right. Like I'm ever going to pick up anyone at a bar where the most sophisticated drink is Miller High Life, I replied to myself.

Trying to forget the woman and the rejection, I went back to the booth to pick up my friends, and we proceeded to the back of the bar. We often used the Wall Nutt as a warm-up for a better place. Tonight, that better place was Mantra.

We left through the back door and weaved through a small crowd of bar hoppers and their cloud of cigarette smoke.

"That girl you were talking to at the bar," began Russ after we had reached the sidewalk. "I think I know her from somewhere."

"Did she shoot you down too, at some other bar?" I asked.

"No, he's right. I think I've seen her too, but I just can't place her," said Gene.

"Ain't too many redheads out there," Sean offered, "So you'd think you would know how you know her."

"You would think," said Gene. "But I just can't remember. Maybe I'm wrong. Will, did you recognize her?"

"Nope."

Without any more ideas, Russ and Gene let it drop. We continued walking through midtown.

"So what about Sherry?" Russ asked after an awkward moment of silence.

"What about her?" I asked.

"He's avoiding it," declared Gene to the others, but looking right at me. I gave him a smug look. "He doesn't want to talk about it," he continued. Then, addressing me: "I'm right aren't I? She about to break it off with you?"

"More like break it off of him," Sean emphasized. "How can she be OK with you screwing her daughter and her daughter's friend?"

"I never said she was OK with the friend," I said. "In fact, I never said she even knows about the friend."

"You despicable bastard," Gene deadpanned with a smirk. "You're a goddamned disgrace."

"Oh, it gets worse," I added. "Something else happened last Sunday night."

* * * * * * * * * *

"Need me to pick you up from the airport?" I texted Sherry.

"You can pick me up anytime you want! :) "

Another text popped onto the screen, this time in a new conversation. "Hi sexpot. You home?"

It was Anna.

"Yup!" I replied.

"We're horny. Can we cum over?"

"Get your hot ass over here!" I replied. Naturally, I assumed she meant herself and Hailey. Both had graduated from high school just two months ago, and both were about to head off to college. When I wasn't sleeping with Sherry, the three of us had spent plenty of time together fulfilling fantasies we didn't even know we had.

But there was one more fantasy to go.

Twenty minutes later, Anna's car arrived in my driveway. She, Hailey, and two other girls emerged. Immediately the air was filled with a cacophony of young women's laughter and loud gabbing. They all appeared a bit tipsy except Anna, who drove. All were wearing tight cleavage shirts, except Anna. She wore a thin, white loose-fitting shirt with long sleeves. It didn't show any cleavage, but it was cut off quite high on her naked torso. The loose end of it swung free in the air, like a short flirty skirt over her C-cup breasts. I could tell by the bounce of her tits and the protrusion of her nipples that she wore no bra. She and one of her friends wore extra-short, pleated skirts, almost like a cheerleader but shorter, and thinner fabric. Hailey wore a tight tube of fabric around her hips that showed off her curves, while the last girl wore a pair of shorts that were so skimpy that they could have been painted on.

Anna greeted me with a kiss, and before I could inquire about her friends, she passed into my house and my lips were greeted with a hard kiss from Hailey. She was still locked on me while the unknown girls followed Anna into the house. They made cat calls as they passed by. My hands quickly found Hailey's best feature--her glorious globe of an ass--and we made out on my front doorstep for another minute before going inside.

The new girls seemed comfortable with all of this, as if they already knew all about me. One was a brunette like Hailey, and the other another blonde like Anna, but unlike the two I already knew, both new girls had curly hair. I began to wonder what Anna had told them. Do they know that she and Hailey come here to get laid? That I'm her mom's boyfriend and she approved our love triangle?

Before I could ask, Anna planted a deep kiss on my lips while Hailey found my iPhone, placed it on my stereo dock, and made a selection. It was my guilty pleasure that I hoped no one would ever find in my possession: Katy Perry's "Firework". The girls immediately started dancing and singing to it. Anna finally released from our kiss and joined the other girls. She raised her hands above her head, causing the scandalously short hem of her shirt to ride up. I could see the bottom curve of her otherwise naked breasts. My dick started to rise to the occasion.

Anna soon went to the refrigerator to get two beers, smacking Hailey's lovely ass on the way. Opening both drinks, she handed one to me and drank nearly half of the other in one throwback.

She smacked the new girls' asses. "Gotta catch up with these bitches!"

Her friends responded with a hearty "Woo-hoo!"

"And so do you, loverboy!" She guided the beer bottle to my mouth and tipped it up, forcing me to drink more quickly than I had anticipated. The beer nearly overflowed out of my mouth before I accepted what was happening, opened my throat, and let it all wash down. The girls cheered when I finish the bottle in one guzzle. Anna bounced back to the fridge and returned with another beer.

In the ten seconds it took her to do this, Hailey wrapped both arms around me, pressed her gracefully curved body against mine, and leaned in for another lustful kiss.

"Hey there, beautiful," I managed to eek out between smacks.

Hailey looked me in the eye as Anna hands me my next beer. "We really need some dick tonight," she said in a sensuously low voice. "Ready for some fun?" She had really come out of her shell in the month that Anna had been sharing me with her, revealing herself as an assertive sex kitten.

"You know I am," I replied. "Who are your friends?"

"Kaylee!" she shouts to one of her dancing friends. "Get over here, you whore!"

"Fuck you, slut!" the blonde replied as she pranced her way over to us. She introduced herself as a college sophomore-to-be, majoring in graphic design. She was on the volleyball team with Hailey when she was still in high school, but doesn't play anymore. Her skimpy shorts were rolled up around her hips and rode low enough for me to see a tattoo of a tough looking anime character. Her low cut cami revealed all I needed to know about her upper body. While not as athletically toned as Anna or Hailey, her delicate curves nonetheless made my cock start to tingle when she pressed her hip against mine. I wrapped an arm around her waist. It felt perfectly natural to do so. Her curves were more dramatic here than those of her friends, and I lightly brushed my hand up and down this space between her hip and ribcage.

The spaghetti straps of her yellow shirt suspended the hemline of her shirt so low that I can see the corner of her pink bra. But I wasn't looking at her bra. I was taking glances at the cleavage that she has proudly put on display. She was only a B-cup at best, but they were wide and perfectly curved. String bikini tan lines ran up to her neck. Her chest was pressed tightly against her shirt, tits aching to burst free. Of course, she saw me looking, as her pretty hazel eyes--surrounded by a thin mote of eyeliner--were locked onto mine. She didn't seem to mind.

"Nice to meet you," Kaylee said with a smile. Her button eyes and matching small nose complimented a face that was framed by curly blonde hair with hints of red in the darker parts.

"So Hailey and Kaylee are friends?" I said, laughing at the similarity. "That's awesome. So if I said 'Hi, Ka-Hailey!' you wouldn't know who I was talking to."