The Ski Bunny Ch. 06

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Anna brings a video camera and her best friend Hailey.
9.9k words
4.7
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Part 6 of the 7 part series

Updated 10/27/2022
Created 10/02/2011
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"Is it awkward?" I asked.

She looked at me with the bright blue eyes that I fell for right after I fell on her at the ski resort. She enjoyed a sip of sauvignon blanc without breaking her gaze.

"Awkward?" Her lips, perfectly covered in scarlet smudge-proof lipstick, effortlessly formed the word. Even having just finished a four-course dinner, they were nearly flawless.

"This sex triangle we have. You and your daughter sharing me."

Anna wasn't just her daughter. They were almost best friends. It had been nearly five weeks since Anna and I first had sex with Sherry's knowledge and consent. Since then I had been living the dream, sleeping with both women regularly, sometimes doing both of them in the same day. A few times I slept with Sherry at night, then after she went to work early the next morning, I did Anna in the shower before heading out.

Three nights ago, Sherry had walked in on Anna and me in the throes of sex on her living room couch. Anna was sitting up on me, cowgirl style. My cock was fully erect and fully implanted in her gloriously tight and clean-shaven pussy. I grabbed her thin waist as she bobbed up and down on me. Her large tits bounced in a rhythm that matched her torso.

I heard the door to the garage open from the far end of the kitchen behind me. I knew it was Sherry. Anna must have seen her, but she didn't stop. She was trying for her third orgasm of the afternoon and couldn't be interrupted.

"Hi Mom," she spat out between breaths without skipping a beat.

"Anna, what are you doing?" Sherry sang. I could hear the smile in her voice.

"Having sex with Will."

"Hi babe." I waved a hand above the couch. "I'm humping your daughter's brains out." My hands then went to squeeze her bouncing tits.

"How is it?" Sherry asked, unfazed.

"Fucking incredible!" "Ohmygod, sooo good!" we answered simultaneously.

"Well, don't let me interrupt."

I began to gyrate my hips. At the same time, I placed a thumb on Anna's clit and began to rub it. She immediately shrieked. "Oh my God!" Then she shrieked again. After a third yelp, rhythmic moaning took over.

"He's good, isn't he?" Sherry commented from the kitchen. Anna was too blissed to respond. I asked myself why I wasn't embarrassed or uncomfortable to have my lover watching her teenage daughter have sex with me. But I didn't dwell on it too long. I was enjoying Anna's body way too much to worry about it.

After a minute more Anna finally said, "Watch this," and leaned over me so that her creamy white tits were right in my face. I began to suck on one of them, using my tongue to play with the erect nipple. We began to gyrate our hips faster and faster. My long, slick rod was plunging into her depths more and more furiously. Her moaning indicated a significant increase in the sensations she was feeling.

I felt such an increase as well. Suddenly Anna surprised me by squeezing her pussy around my dick in much the same way her mother had perfected. As if her pussy wasn't tight enough on its own, this new skill took fucking Anna to a whole new level. I could feel the inevitable ascent to orgasm accelerate. I initially thought that I could still stop and change positions to prolong it, but I thought Aw, fuck it, and decided to just let it come.

And did it ever come. Anna and I were banging our pelvises together so fast and hard that the slapping echoed off the far walls of the kitchen. She squeezed her pussy around my dick again, and that was all she had to do; My orgasm accelerated past the point of no return.

The intensity of sexual pleasure soared through me as I pushed myself hard and deep into Anna. I grunted repeatedly. She was nearly screaming as I ejaculated. Stream after stream of my cum shot out my dick and into her pussy. I grabbed her ass as more and more cum came out, each spurt accompanied by the most heavenly sensation. We gyrated and milked it for everything it was worth. We were only half conscious when we slowly came down from our highs.

Anna was still hunched over me when I heard Sherry speak up. "Ahh, the lovely transfer of semen from one body to the next. Nice job you two."

Nether Anna nor I said anything right away. We were left speechless and breathless by the remarkable climax.

Three days later I was out with Sherry on our formal date that we had been planning for two weeks. She glanced down at her nearly empty dinner plate. Her long eyelashes were like the tassels of a curtain closing on her lightly brushed eyelids. When the curtain raised, the glimmer in her eye matched the glint of chandelier light that reflected in her dangly metallic earrings. My lady held onto her beauty like the blooms of an amaranth.

"Is it awkward?" I repeated.

Sherry took another sip of her wine. "There are so many situations that can make someone feel uncomfortable. Jealous. Snubbed. Angry. But I believe that sometimes we can choose how we think about them."

"Human nature is what it is," I said as I finished the last bite of my salmon tilapia. "It's not always easy to choose."

"True," she replied as she leaned forward a bit. I glanced at her chest for the 30th time that night. The top of her black dress wrapped around the back of her neck and barely concealed enough of her breasts to be considered appropriate for this restaurant. "But it's always better if you can. If you make up your mind...." She paused. "If you are determined to approach a sticky situation with a mindset that will result in the best possible outcome, that is exactly what will happen.

I nodded, figuring that my little optimist was going to have a great response when I pressed her again: "So how are you choosing to think about the three of us?"

She didn't answer right away. She just stared back at me. I was transfixed by her beauty. Sherry had pinned her hair up, but allowed a thin lock on either side of her temples to fall, framing her face with an elegant blonde luster. Finally, she broke her gaze and sat up straight.

"My friend Molly has an eleven-year-old boy who has been involved with Little League baseball for a couple years," she began. "The kid has become quite the star pitcher, and the coach said he sees big things happening for him in the years to come: Little League world series, college scholarship, maybe even the majors someday. Who knows? But toward the end of last season, he only went to baseball practice about half the time. The other days he was at soccer practice. Molly says her son likes soccer just as much, even though he isn't as talented at it. She was afraid that the baseball coach could become upset and demand full commitment to his sport."

"But he didn't?"

"The coach is very good—as a baseball coach and as a person. His philosophy is that he is not just coaching a baseball player. He is coaching the whole child. He chose to accept Molly and her son's decision gracefully. He understood that playing soccer made the boy just as happy as playing baseball, and he wants what was in the boy's best interests."

"But if he could earn a baseball scholarship, isn't that in his best interests?"

"Someday it probably will be. But for now, he's only eleven. The coach knows that he can spend a couple years trying out different things, finding what he enjoys doing, and have the experience of a well-rounded childhood without having to become too serious too soon. Then if he comes back to baseball as his primary sport, he can pour himself into it wholeheartedly. If it's the boy's choice, he will enjoy it more and get even better at it. But if he's forced into it too much, he will hate it and might quit altogether."

Sherry stopped speaking and waited for my response, but I didn't know what she was getting at.

"OK, makes sense," I said. "Good for Molly and her son. And the coach. But unless you want to get kinky in the bedroom, you and I aren't playing baseball or soccer."

Sherry sat back, and sighed. "Don't you see how this relates to us?" she said.

I felt like a typical male: thick-headed. "I'm sorry," was all I could say. Sherry reached across the table and took my hands in hers.

"Will, I've never felt this way about anyone else. Every time I see you...every time I know I'm going to see you, I get a rush of adrenaline, and I swear I can fly. It's more than just sex, although I admit that that is really, really good! You make me so happy, and I want you to be happy, and I want Anna to be happy."

"So do I," I said, squeezing her hands.

"And if that means we share you for a summer, that you don't commit yourself exclusively to me yet while you experience things that make you happy, then I'm all for it. I'm watching you go through your summer of love, and it's like you have a permanent smile. Your energy infuses everyone around you, especially me. Anna will go away to college in a couple months and then it will be just you and me."

I thought about it for a moment. "So you're willing to wait for me to get it out of my system, after which, if it's mean to be, we're with each other exclusively."

Sherry smiled and nodded. "See, you're not so dumb."

I chuckled. "Wow." I had counted my blessings to myself numerous times in the last couple months, but this time I had to say it out loud. "How did I get so lucky? You are the perfect woman."

Sherry beamed. I motioned for her to lean over the table. I met her halfway and we kissed slowly and passionately. Her eyes stayed shut well after our lips separated.

After we both sat back, Sherry reminded me, "Just remember the terms of our agreement, loverboy. I always come first."

"As you wish, m'lady."

And with that, my summer was set. I absolutely loved having sex with Anna. Just the thought of it made me get hard instantly. But I knew that this arrangement couldn't last forever, and even though I knew I would miss it when it ended in just a couple months, I was actually looking forward to having an exclusive relationship with Sherry. My feelings for her had only increased since the first time I humped her daughter. The long-term implications of this were not lost on me. I had not yet used the L-word to describe how I felt toward Sherry, not even to myself. I had avoided even thinking it so far. But I knew the possibility was there.

As compatible as we were in the bedroom, we had grown closer outside as well. We had become each other's motivator-in-chief for staying in shape. We bought memberships at a health club halfway between our houses. If one of us felt like flaking out on a self-assigned workout day, the other played the part of the personal trainer. All the men at the club appreciated Sherry's presence, as she normally wore little more than a sports bra and a pair of skin-tight yoga shorts. The lap pool offered more temptation: Even in a one-piece, she was eye candy.

In good weather we would run or bike a few miles on a trail near Sherry's neck of the woods. We even went back country camping at a state park a couple hours outside of the city. A tent may not be the most comfortable place to have sex, but it certainly was exciting. We didn't even squelch our noisemaking.

Our dates kept us active in the downtown scene. We went to concerts, plays, soccer games, baseball games, art festivals, and an air show. We even found ourselves in the middle of a gay pride block party a few weeks ago and befriended some of the hippest party people in the metro. I went with her to see her nephew in a swim meet, and she came with me for clothes shopping. I usually hate that, but she made it fun, and now my wardrobe is notably better because of her advice.

On separate occasions we found ourselves running through a fountain fully clothed, infiltrating the club lounge of the local five-star hotel by pretending we were guests, and driving through the theater district with windows down, belting out every lyric to "Ice Ice Baby". There was even an ill-conceived attempt to imitate the song "Escape" by making love at midnight in the rain with piña coladas, but we ended up running from a security guard while caked in mud and with a cut on my hand from a broken glass. We laughed so hard I thought I was going to vomit. I was never bored with Sherry. Her smile was captivating, and I became addicted to her touch.

Tonight was no exception. After resolving any uneasiness from our love triangle, Sherry and I flirted with each other the rest of the night, playing footsie under the table and inserting sexual innuendo into our conversation. She revealed her lack of panties, and even flashed me a boob when she thought nobody was looking. After dinner we went to a local dance club that was known to cater to the 30-something crowd. The men gawked at Sherry, and she said she noticed a few female eyes turned on me. Neither of us worried. We drank and danced until we could no longer wait to rip each other's clothes off.

I drove her back to my place, we ran to the bedroom, and our clothes were off instantly. With absolutely no foreplay, I got on top of her in missionary position, and before she could say "Fuck me!" three times, I inserted my dick into her eager pussy and immediately started pounding away at break-neck speed. The sound of our grunts filled the room right from the start. We were both as horny as we had ever been, and we were both satisfying our lust with a high-speed fuck. No other positions were necessary. We just fucked and fucked and fucked and fucked.

Sherry grabbed my ass as I kissed her between bouts of heavy breathing. I was so energized that I felt like I could go on like this indefinitely. But after a mere three or four minutes, I felt my troops amassing in my balls. They were getting ready to be launched into Sherry's abyss. It was a heavenly feeling, and it just kept intensifying. I didn't slow down, and neither did Sherry. I drove as deeply into her as I could, making micro-thrusts as cum gushed out of my cock. My orgasms are particularly debilitating, and this one was no exception. I grunted through it without being aware of anything else in the room. When it finally ended, I collapsed on top of Sherry, and it took a minute or so for me to remember where I was.

That was our initial quick fuck. I didn't even pull out, and after laying in each other's arms for fifteen minutes, we started to make love. We both went more slowly this time. Sherry climaxed twice, and I lasted much longer. Hours later, when sunlight streamed between the blinds and onto the bed, we woke up and made love again before falling asleep for another few hours. When we finally got up for breakfast, I was all but ready to tell Sherry that I was in love with her.

* * * * * * * * * *

Two of my closest friends had noticed a change in me after I got back from my ski trip. They knew it was a woman, and after a few weeks of dating Sherry, I introduced her to them. They were duly impressed. Sherry often came with me to hang out with them. She didn't shy away from yelling at the refs when we watched a game on TV or even in person, which impressed my friends even more.

But they didn't know about Anna. I was cautious at first, and as the weeks went by, they pushed me for more details about why I was cancelling so much time with them. So I finally told them. Naturally, they didn't believe me at first, and we never brought it up around Sherry. But they had faith after I showed them a sexually charged text message that Anna had sent, complete with a picture of her in a skimpy outfit. After that I became their god, much like the frat boys on the ski lift just three months ago.

Summer was in full swing, and I found myself refusing my friends' invitation to see our local MLB team blow another game so that I could hang out with Sherry and/or Anna at their house. They understood, but warned me not to overdo it. I took their cautions to heart and wondered, as I pulled into Sherry's driveway, if I should have just gone to the game.

Nobody answered the door, but it was unlocked so I let myself in. My calls for "Anybody home?" went unanswered. The pool looked inviting, so I stripped down naked—knowing none of Sherry's neighbors could see her pool—and dove in. I wanted to swim a few laps, but the water was too hot for exercise, so I relaxed back against a wall until I heard voices inside the house. I swam to the wall closest to the house and pressed my body against it. Anna emerged from the house with a beautiful brunette who looked to be her same age and height.

"Hi Will! Getting' in a swim?" Anna said cheerily.

"Yeah, but it's a little too warm for a workout."

"So you brought your suit?" What a tease. She knew the chances of me having anything on were very slim.

"Who's your friend?" I asked, dodging her trap. Anna pulled Hailey closer to the pool, and I braced myself tighter against the wall.

"This is Hailey. Hailey: Will."

"Hi Hailey."

Hailey responded only with a quick hand wave and a sheepish grin. The tips of her long brown hair swayed in the slight breeze. Her skin was a shade darker than Anna's. She had a thin, athletic build like Anna, which was shown off best by a tight pair of pink volleyball shorts. I couldn't see her butt, but the shorts clung to her hips and upper thighs, emphasizing her muscle tone. I took advantage of my vantage point from below to see a slight camel toe at her crotch.

"Are you a cheerleader, too?" I asked.

"No, I play volleyball. Well, I mean I played volleyball. Past tense."

"Aww give yourself some credit," Anna said. "You know you're gonna make your college team. Will, she has the second highest number of ace serves in our school history."

"Not bad!" I said.

Hailey had all the right curves. They gracefully traced a line of classic beauty and sex appeal all the way down her lithe body. Her face was beautiful too. More rounded than Anna and Sherry, her dimples belied her age of what I assumed to be 18, and made hers the cutest face I had seen since I was in college. Black eyeliner emphasized her bright green eyes, a product of colored contact lenses, I assumed. Her upper lip curved up to reveal perfect front teeth, and both lips subtly curved up at the ends, leaving her with a perpetual Mona Lisa smile.

Her low-cut tank top stretched tight over what I estimated to be B-cup breasts. Anyone who appreciates the female form as I do knows that a woman need not have huge breasts to be sexy. Hailey's were a nice size, to be sure, but more than that they seemed perfectly rounded. The curves of her cleavage shone in the midday sunlight and complimented the rest of her body's curves. Her nipples poked at the tight fabric, making tiny tents just under the hemline.

"We're gonna order a pizza and hang out here for a while," Anna said. "You in?"

"Sure," I replied.

She threw me a towel which I caught just before it hit the water, and I used this to exit the pool without revealing my complete nakedness to Hailey. She made no secret of looking at the rest of me. The girls mixed themselves a pitcher of lemonade, tea, and vodka, which they called a John Daly. Anna threw me a beer, and we sat by the pool and chatted.

The girls talked about college: the promises, the unknowns, and all they hoped it would be. I told them a few stories of my own experiences, but kept them rated PG-13. They begged me for some R-rated stories, which I would have told Anna, but I was too hesitant to do that in front of someone I had just met.

Hailey was certainly very attractive, but it was slightly mitigated by her nervousness. She fidgeted with her hands and laughed anxiously. She had no trouble contributing to the conversation, but there was a hint of coyness to her. I knew that Anna had probably told her about our relationship as fuck buddies. Anna probably thought that, as her best friend, Hailey would be comfortable meeting me.

The pizza came and it was quickly consumed. I drank a couple more beers, then tried the girls' drink which was actually quite refreshing. Hailey became more relaxed as the evening went on, opening up a bit about her high school life and volleyball career. I had gotten a few glances of her butt, and it was indeed everything I had hoped: The extra short, sheer shorts showed off a tight and muscular butt that was still round enough to want to grab hard. And that completed the package. It was official: I was hot for Hailey!