What I Say Day

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I cash in when my girlfriend loses a bet.
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This is my entry into the 2021 Nude Day contest. I always like to reinforce that, like my author name says, all of the stories I tell here have a basis in truth and are always based on actual events from my life. That being said, I do like to add some twists & embellishments to keep them interesting for the readers. This one has a bit more embellishment than some others.

This story has waves of exposition, story and sex, so be prepared for some repeated build-ups between sex scenes. I also had to "bend" the rules a bit and not have it take place in Summer for Nude Day -- because the original real event was in winter and would have changed the story too much. I think it keeps with the general "Nude Day" theme though.

Hope you enjoy -- please leave feedback.

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I was first introduced to "What I Say Day" when my then-girlfriend, now-wife, Sherri and I had been dating for about a year. We met at work and were both in our late-20s. We were out to dinner one night and I commented on the wedding date of a mutual friend. Sherri said it was in mid-August while I vividly remembered it being in June.

"Wanna bet?" she asked.

"Sure" I replied. "What are we betting?"

"Whoever is right gets a 'What I Say Day' from the other person."

Confused, I asked, "What is a 'What I Say Day?'"

"Oh. It's something my family used to do to get out of chores or when we wanted to do something different on a weekend or were arguing about a movie. Basically, winner gets to dictate what the loser does for a day."

Confident I was correct on the dates, I reached across the table and we shook hands, "Deal."

A few weeks later, we were in my car, driving to visit Sherri's Aunt Marie who lived about 4 hours away. When we got there, I had the unequalled joy of loading up three SUV-loads full of things from her attic and basement and brought them to the local church for their annual sale. We enjoyed a ~lovely~ early-bird meal at 4:30 before going back to Marie's house to watch TV and old movies for the night. That night, I got to sleep in a twin bed in a spare room down a creaky hall from my girlfriend.

Yeah, the wedding had been in mid-August.

Over the years, we brought back the "What I Say Day" bet a few times. Winning days consisted of everything from art museums to baseball games. Once, I got clever and told her my "What I Say Day" would consist of golfing with my pals while she had dinner ready when I got home, followed by a massage and blowjob to "relax my golf muscles". I still think my worst loss was when I had to go to an endless marathon of the Lord of the Rings movies that went all night long. By 3am, I was hoping some sort of troll or ogre would end my suffering.

But that loss was offset by my best win, that came thanks to the actress, Tia Carrere. For those who don't know her, she was an immensely popular Asian-American actress in the late 90's. She's probably best known for her roles in "Wayne's World" and "True Lies".

Sherri and I happened to be out one night and Tia Carrere was shown on TV at a local sporting event. When she looked up at the screen, Sherri asked me, "What James Bond movie was she in?"

"She wasn't ever a Bond girl" I replied.

"Yes she was" insisted Sherri, "she was a villain. I remember." I could hear the confident tone in Sherri's voice, but (to sorta-quote the Princess Bride) I knew something she didn't know. I was a colossal James Bond fan growing up. I knew all the movies in order, sure, but also more than that. I could name Bond Girls, villains, songs and artists with years they were released. I could even name the "Obligatory Sacrificial Lamb"- the ally or friend of Bond who dies -- from every movie.

Knowing I had her, I simply extended my hand and said, "What I Say Day?". Sherri shook on it and sealed her fate.

"You're thinking of 'True Lies'" I started, "It's with Arnold Shwartzenegger and Jamie Lee Curtis. Tia Carrere played a bad guy who kidnaps Jamie Lee. But it wasn't a Bond movie." A quick internet search when we got home proved I was right and solidified my prize for a future date.

Some time passed and occasionally the bet would come up in conversation but I hadn't really had an effective use for it yet. We were living in the Northeast and toward the end of winter, we decided that we wanted to get away for a weekend. Sherri found a resort that offered private lodges and chalets by a lake and ski resort. We hadn't skied in years, but the thought of a large resort with a lodge, restaurant, fire pits, indoor/outdoor pools and hot tubs was definitely appealing. Plus, we would have the privacy of our own chalet with a fireplace, outdoor hot tub and kitchen if we just wanted to hang around. We booked a long weekend, arriving on Thursday evening and leaving Monday.

The drive up took about 3 hours and by the time we got there, it was dark out. We checked in at the main lodge around 7:30 where they gave us a little driving map to our chalet about a half-mile away. The map showed all the attractions and amenities of the resort -- pools, slopes, lodges, trails, activities, restaurants and more. They even had a complimentary heated shuttle bus to take guests around. We decided to drop our bags in the chalet, then grab a shuttle to the pub that was on the premises.

We parked in front of a two-story shingled chalet that the map guided us to. We opened the door to see that we had a fun, rustic property for the weekend. The main floor had a full kitchen, breakfast area with a table and chairs, living room with couches, tv, gas fireplace and a half bathroom. There were sliding doors by the fireplace that led outside.

By the kitchen was a set of open stairs that went to a loft bedroom that looked over the main room. It had a king-sized bed that looked like it was made of logs and a huge bathroom with a tiled shower with multiple shower heads that was clearly built for two people to occupy at the same time. The entire second floor was surrounded by large windows which provided a view of the entire resort. We could see the lights of the other chalets, the main lodge in the distance and some of the lit trails for night skiing.

We walked back downstairs and opened up the sliding doors to see that we were on an oversized deck that we assumed in Summer would have lounge chairs and tables for relaxing. While all these were stacked up at this time of year, there was a hot tub at the very edge of the deck, seemingly leaning over the hill the chalet was built on. The chalet seemed completely private, but when you walked over to the hot tub, you could see the lights of the other chalets around. In fact, the most prominent thing we could see through the darkness was the misty-blue glow of the hot tubs from other nearby chalets.

Sherri was ultra-organized and asked if she could have 15 minutes or so to unpack and freshen up. I took that time to put the beers, wine, and food we had brought with us into the fridge. When Sherri came down, she had freshened up her hair and makeup a bit. Sherri was built like a model at 5'8" with long legs and a slight build. She had smaller b-cup breasts and a tight, athletic ass. Her long blond hair flowed down to the middle of her back and was pulled back into a ponytail. She was wearing a pair of tight skinny jeans and hiking boots with a small heel on them, the combination of which boosted her amazing ass up for perfect viewing. She had on a tight red turtleneck that highlighted her slim waist and breasts.

I called for a shuttle to pick us up and a few minutes later, we were pulling on our big winter parkas to head to the pub. Sherri's was a more fashionable parka that came down to the top of her ass, since she wasn't planning on any major winter activities beyond drinking wine and watching snow fall. Mine was longer and heavier and I brought it just in case I wanted to go snowmobiling during our stay.

The pub was a quaint little place with good food and great drinks. Because it was our first night and we knew there was a shuttle, we ate a great meal and took full advantage of the drinks menu. By the time we left the pub and made our way to the shuttle, I was confident that it wasn't the ice that had us a little unsteady on our feet.

We got back to the chalet and climbed the stairs to the bedroom loft. Sherri told me to use the restroom first and then she would meet me in bed. After I was done and as I got undressed, I realized that with the room fully lit, people in the higher chalets or even some of the walkways could see directly into the loft. More concerning was the realization that we would be up at the crack of dawn when the morning sun started pouring in through the window-walls! Fortunately, I found a bank of switches on the wall, that as you turned them, they closed the various sets of blinds surrounding the inside of the chalet. I closed the blinds and settled into the bed to wait for Sherri.

A few minutes later, the bathroom door opened and Sherri stepped out. She looked amazing and obviously had gotten into the spirit of a "winter weekend getaway". She was wearing a pair of lacy black panties that were cut high up on her hips. On top though, she had on a Boston Bruins hockey jersey that she had cut, so it ended just at the bottom of her boobs. She was showing the perfect amount of under-boob and was flashing her nipples with every step she took. Her long legs were the highlight of the outfit, though. She was wearing a long pair of thigh-high white hockey socks with gold & black stripes around her thighs.

Sherri wasn't an athlete or even a big sports fan, but she looked like every fan's dream girl. The socks made it seem like her legs went on forever, and the cut jersey was showing off her tight stomach and abs. Watching her tits bounce under the shirt as she walked over and climbed on to the bed made me instantly hard.

As she straddled me on the bed, I couldn't help but reach up and start caressing her tits under the half-shirt, running my thumbs over her nipples and into her cleavage.

"So, I guess you like my outfit?"

"Babe" I replied, "You look incredible."

With Sherri, there was always a perfect point of alcohol consumption and I think she hit it that night. Too little, she remained her normal conservative self. Too much, she got tired. But when she had the perfect amount, her inhibitions would melt away and she would become a hellcat in bed. It was during these times that she would try new positions and often orgasm more easily. I think that the alcohol would allow her to stop being self-conscious; relax, and let her sexual instincts take over.

Sherri was rotating her hips on me, grinding her crotch against my cock through my boxers. I kept my attention on her breasts, switching between gently rubbing and stroking them to an occasional pinch of her nipples. I could feel her nipples getting harder every time I went back to them and her gyrations were getting faster and harder against me.

I reached around and grabbed her ass, forcing her down against my crotch with a bit more friction and pressure.

"Oh fuck," she moaned, "I think I can come this way." She braced her hands on my shoulders and really began to grind her pussy on my crotch. She switched from a back-and-forth motion to more of a circular movement, grinding her panty-covered clit on the head of my cock. Her breath was getting shorter and faster and could feel some beads of sweat starting to form on her chest.

"Uh...uh....uh....I'm so close." She was moaning now. "Grab my tits. Pinch my nipples."

I switched my hands back to her tits. "Please.....oh, my.....I'm gonna come...That's it...I'm uuuugggggghhhhhhh." Sherri's entire body started to shudder as she climaxed. She knocked my arms out of the way and collapsed on my chest as the aftershocks rippled through her. I could feel the wetness of her orgasm as it had soaked through her panties and my boxers. Sherri's head was resting on my shoulder as she worked to get her pulse rate back to normal.

After a few minutes, Sherri began to stir on top of me again. Grinding against my still-hard cock she said, "Feels like someone is ready for some relief, huh?"

Sherri rolled off of me and peeled off her top and panties revealing her mostly bare pussy with just a dark blonde landing strip. I could still see the moisture of her recent arousal and orgasm as she laid back on the bed and spread her sock-covered legs wide.

I slid between them and lined my erect cock up with her spread lips. As I slid into her, it was a mixture of sensations. She was still nice and lubricated from her orgasm so I thought I would have slid in easily. But that same orgasm had the walls of her pussy so aroused and inflamed that it felt tighter than it usually did. I adjusted my weight forward and pushed my cock further into her slick tunnel.

Sherri began moaning again, "MMMMMMM...babe. You feel good. Go nice and slow for me. I'm still so tight." I took her cue and started slowing moving my hips back and forth, not rushing my pace. Sherri had her hands on my ass and was digging into my skin with her fingernails. A quick smack on my right ass cheek and I knew I she wanted me to pick up speed. Just as I started to build up some rhythm, Sherri shifted a bit and brought her legs up and put her ankles all the way up on to my shoulders. I was always impressed and excited by her flexibility and this move spread her pussy wide open for my thrusts.

"Fuck me, babe. Fuck that pussy." I could feel the pressure building up as I wanted to shoot inside her. The combination of her hands grabbing my ass, her dirty talking and the feeling of her socks on my shoulders became too much. With a loud moan, my entire body tensed and I felt my balls release a load of cum into Sherri's pussy. I continued thrusting until I felt the final shots cover her walls.

"Jay.....I need to move my legs." In my excitement, I forgot that Sherri's legs were still perched on my shoulders and her hips were being stretched. I gently grabbed one ankle and eased her leg off to the side. She was able to slide the other one off, allowing me to roll off of her.

"Wow" she said. "That was awesome." Sherri was running her fingers through our combined juices flowing out of her. "I'm exhausted. I'm going to clean up and get some sleep." After cleaning ourselves up, we got back into bed and fell into a deep sleep for the night.

The next morning, we slept in thanks to the blinds working the way they were designed to. I was up first and used the bathroom to brush my teeth and wash up a bit. I knew Sherri would get up soon and we hadn't decided on a plan for the day, when an idea hit me.

I crawled back into bed and Sherri started stirring a bit. Her back was to me, so I wrapped my arms around her and spooned against her naked body. She could feel my morning wood pressing against her ass and started to push back against me. Once again, my free hand found her breasts and I started gently twirling around her nipple.

"Mmmmm....Jay, stop it. I'm still exhausted from last night and my head is pounding." Not listening, I let my hand roam down toward her pussy before she grabbed me by my wrist.

"Ugh. I'll be right back." Sherri rolled out of bed and went into the bathroom. I could hear her brushing her teeth, washing up, peeing and the familiar shake of a bottle of Advil. A few minutes later, she emerged from the door and started walking naked back to the bed.

"Stop there for a second" I said.

She listened and looked at me with a curious look on her face. "What's up?"

With a smirk emerging on my face I said, "I'm calling in my 'What I Say Day' starting ... now."

"What are you talking about?"

"Tia Carrere. True Lies. Not a Bond Girl. You owe me one day of whatever I say!"

Sherri knew the bet and the rules so she slumped a bit and said, "Fine. It's your day. So what are we doing? Snowmobiling? Hiking? Freezing our asses off somehow?"

"Nope." I replied, "As a matter of fact, we will barely leave the Chalet. But I have one rule."

"What is that?"

"You have to stay naked all day."

"What?"

"My day, my rules. No clothes for you all day." The look on Sherri's face was a mix of confusion, anger and defeat.

"What about food? You want me to go to the restaurant naked?"

"Nope. We can eat in here today. We'll do the restaurant tomorrow night."

Knowing she was beat, Sherri reluctantly gave in. "Fine. I'll stay naked. But I'm going to remember this the next time I win." With a smile she then added, "But since we're both naked right now, we might as well make use of the time, right?"

"Absolutely!" I said as she started walking toward the bed. "But first...". I then reached over and hit the switches for the blinds letting the sun pour into the room.

As Sherri's eyes adjusted to the streaming light, she screamed, "Jay! No! People can see in the room and I'm naked!"

"That's the idea. There's a good chance some of our neighbors are going to get a view better than the mountain and lake today!"

"Holy shit. I can't believe you are turned on by me showing myself off to strangers all day."

"Babe" I said, "It's not like you're going to be parading down main street in the nude. You just may be giving a few glimpses to any peeping toms who get lucky today! And since it's my day, I know the perfect way to start it."

I peeled back the covers showing my erect cock. I started to gently stroke it, bringing it to its full length.

"I think that's enough debate for now. It's my day, so why not put that mouth to use?" Sherri climbed back on to the bed and replaced my hand with her own and started stroking me. She leaned down and used her tongue to start licking up and down my shaft.

"You really are a sick fuck, you know that?" she said just before she plunged her mouth down the length of my cock. She started licking and sucking building up speed and moisture as she did. Using her hand, she fondled my balls while she continued her expert blowjob. Her long blonde hair had fallen around her head and was tickling my hips and thighs every time she would move her head down.

As I looked down at Sherri's head bobbing up and down, with her ass up in the air, I felt myself get even more aroused at the thought of who could be watching through the open windows. Sherri must have sensed the slight change because she increased her suction and used her tongue to lick the head of my cock. I couldn't last and shot a full load into her mouth and throat. As I continued to pulse out some weakening streams of cum, Sherri pulled off my cock and aimed my dick at her chest. The final spurts of milky fluid left ragged streams on her tits and torso. As the final drops came out, she backed off, licked her lips and gave my dick a gentle kiss.

"Well, now I definitely have to go shower. If I have to be naked in this place all day, you better go down and turn on that fireplace to warm it up for me and I'm sure not doing it with your dried cum all over me."

While Sherri went to shower, I threw on my shorts and t-shirt and went downstairs. I started some coffee and turned on the fireplace to start warming the chalet a bit. I also took the opportunity to take a look at the deck and patio in the light. The patio actually had a large heater that could be turned on from the inside, which warmed up the entire area to the hot tub.

I went back to the kitchen and opened up the container of muffins we had brought with us, throwing two of them in the toaster oven. When I heard the shower shut off, followed by Sherri's hair dryer, I started to pour the coffee and put muffins on some plates. I heard Sherri's feet coming down the stairs and looked up to see her naked body descending. Her skin was still flushed from the shower and I could see the combined effects of the heat and moisture on her body. Her small pink nipples were tight and puckered having come from the hot shower to the cooler room. Her shoulders were still red and flushed and I could see her long legs shining from the moisturizer she usually used. I would never get tired of looking at her tight, athletic ass as it rippled and bounced with every step she took.