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.
Sherri came over to the kitchen, grabbed her muffin and coffee and went over to the sofa in the living room.
“So, I’m just supposed to sit around naked all day?”
“Sorry, babe, that was the bet.”
“But you get to wear clothes? That doesn’t seem fair.”
I shrugged a bit, wondering if she was right, but thinking to myself that her naked body was a much better sight than mine walking around naked all day.
“I was going to sit and have breakfast at the table” she continued, “But it feels awkward just sitting naked with my tits out like that.” I grabbed my breakfast, walked over and sat in one of the chairs in the living room.
“Sher, I don’t think you realize just how hot you are. Your tits are amazing, your ass is almost inhuman and I think you know how much I love the rest of you. Look, we were planning on taking one day this weekend to sit around, read, drink, and fool around, right? Let’s make today that day, but you get to be naked!”
“Fine” Sherri said with a shrug. “I’ll go get my Kindle and read for a bit while I have my coffee.” She jumped off the couch and gave me a quick peck on the cheek. “You’re still a dick for making me go through with this.”
With an awful British accent, I said to her, “Bond. James Bond.”
“Such a dick!” she yelled over her shoulder. I swear as she walked away this time, she purposely added a little extra wiggle to her walk.
The morning passed pretty normally. Sherri settled back in on the couch, with her Kindle, coffee and a blanket over her legs. I was sitting on my laptop mixing some work, with some browsing, with some YouTube videos. Every once in a while, I would look up to see her sitting demurely with her tits bare above the blanket. Of course, a number of times she would catch me looking and would smile back.
As the day approached noon, I decided to wander out to the deck and see how the heater and hot tub worked. I threw on a sweatshirt and sneakers and opened the sliding door, letting in a quick blast of cold air.
From the couch I heard “Fuck! Warn a girl before you do that!” I looked back to see Sherri’s nipples had instantly hardened from the cold air and she was pulling the blanket up higher on chest.
In the daylight, I had a better look at the deck and hot tub. The deck was about 15 feet long with a log railing that went up to about my chest. Because it was a solid railing, you couldn’t see under it. The hot tub was on a slightly raised platform to the left, probably to allow occupants to see over the railing while sitting there. There was some deck furniture stacked to the right. I looked up to see a large gas heater on the ceiling that ran the length of the deck, with a timer switch on the wall.
I turned the dial and heard a “whoosh” sound as the gas ran through the unit and the pilot light caught the flame. Within seconds, I could feel the heat starting to pour down. Since I was out there, I uncovered the hot tub and stuck my hand in. Even though it was just in “resting” mode, the water was bubbling and hot to the touch. I turned that timer on to get the water fully churning. Finally, I walked back, grabbed two lounge chairs and laid them on the deck. Even though it had only been a matter of minutes, the deck was warming up. If you stood up, you could still feel the cold air coming over the railing, but further down the heat was getting trapped creating a nice comfortable temperature.
I ducked back inside and started heading up to the loft. “What have you been doing out there?” Sherri asked.
“Hold on. Not done yet.” I went upstairs and got some extra bath towels from the bathroom. Taking them back down to the deck, I put one towel down on each chair and then rolled a second one making a little pillow. I knocked on the glass door to get Sherri’s attention and when she looked up, I signaled her to come outside. She got up, wrapped the blanket around herself, and slid open the door.
“What do you want? It’s freezing out?” As she said it, Sherri felt the heat from the blower and saw the hot tub. “Wow. This is so cool.”
“I was thinking since it’s about lunch time, I’ll grab some of the cheese, bread and wine and we can sit out here for a bit.”
“That sounds awesome. I have to pee anyway.”
While Sherri went to the loft, I grabbed the lunch items and opened a bottle of wine. I was just putting them on a tray when she came back down the stairs. The fact that she still had the blanket around her wasn’t lost on me.
“C’mon” I said, “I’ll carry the tray, you open the door.”
As I expected, Sherri opened the sliding door to let me slip outside. She followed, closed the door behind her and started to sit with the blanket around her.
“Uh, are you forgetting something? Lose the blanket.”
Sherri’s face went from relaxed to angry in seconds. “Are you fucking kidding me? You aren’t serious. We’re outside. It’s winter. Someone could see me. I’ll freeze.”
“Sorry, babe, you lost the bet. And for ‘What I Say Day’, I said you have to be naked. You can lay on the blanket or put it back over your legs, but I want to see some skin on display again.”
Sherri glared at me but adjusted herself so that she was laying on the blanket, keeping it wrapped around her legs as much as possible. I poured some wine for both of us and we started to eat some of the cheese, bread and fruit. Even though Sherri was tense, angry and fidgety at first, she started to settle in. With the heat lamp on, it was warm on the patio as long as you stayed below the line of the railing. She continued to sip her wine and read her Kindle as I worked on my laptop. Every so often, I would look up and could see people walking on the trail nearby and even some distant skiers on the slopes.
We had been sitting for around an hour when I heard footsteps coming closer to the patio just before I heard a man’s voice saying, “Hello! Don’t want to startle anyone!” Sherri must have dozed off in her chair because the voice startled her and she sat up quickly, dropping her Kindle on the floor. Just as she did, a middle-aged man and woman dressed for winter hiking came around the corner of the chalet and appeared over the railing.
“Sorry! We are in the next chalet over and was wondering if you knew how to get to the Caribou tra…….” The man’s voice trailed off as he realized he was staring at a naked woman less than 4 feet away from him. Sherri hadn’t done herself any favors as she had swung her legs off the chair when she got startled in an attempt to stand up. So, just as the couple appeared, Sherri was basically sitting naked with her legs slightly spread giving them a view of her pussy and her tits had hit some of the cold air and prominently perking up.
The other woman was the first to recover as she half-turned away and grabbed her husband’s arm. “Hal, let’s leave these kids alone. We can find the trail ourselves.” You could hear by the tone of her voice that she wasn’t offended and was even slightly amused by the whole situation. Hal, on the other hand, couldn’t seem to form a coherent sentence.
“I swear…Donna…I didn’t…I tried to call out…why was she naked?”
As she led her husband away, Donna called back, “Sorry to interrupt, kids! We’ll find the trail ourselves! Have a good afternoon.”
I started to chuckle until I saw Sherri’s face. It was red with a mix of anger and embarrassment and glaring at me.
“Jay, you fucker! Two strangers just saw me completely naked. That guy literally just got a full look at my pussy and tits.”
As I started to respond, I noticed a couple of things. First, Sherri hadn’t covered up. She had turned to face me, but she was still naked. She hadn’t used the blanket to cover up or run inside. Also, I knew her looks. Yeah, she was mad. Yeah, she was embarrassed. But she was also aroused. Despite everything, she was starting to get the appeal of the game.
“Babe. You probably just gave that guy the highlight of his trip and a story he’ll be telling his pals for years.” I went over and sat on Sherri’s lounge chair with her in front of me, “And even if you don’t want to admit it, your tits and pussy are a sight ANY guy would give his left arm to see.”
Since Sherri wasn’t pushing me away, I started to run my hand around her back and started to cup her breasts. I started kissing the nape of her neck which I knew she loved. Her body started to react as she leaned back into me, rolling her head to let me keep kissing.
“I’ll bet you later today, when they get back to their chalet, Hal & Donna are gonna have amazing sex thanks to your little show.” I was now snaking one hand lower, trying to gently spread her thighs apart to give me access to her pussy.
“Ok” she admitted, “It was kind of hot to be seen like that. But it’s still so embarrassing.”
I now had one hand between her legs and I was starting to spread some of the moisture forming in her pussy to her clit. I was alternating my fingers between dipping slightly into her wet opening and circling her clit with them. My other hand kept rubbing her breast and teasing her nipples. Meanwhile, Sherri had taken her hand and was started to stroke my cock through my shorts.
“I can’t believe this whole thing has me so turned on” she started, “Let’s go inside and fool around.”
“Nope. I have a better idea.” I stood her up and led her toward the hot tub. At this point, Sherri wasn’t even resisting. Even though her naked breasts were exposed to anyone who looked our way, she no longer seemed to care. As we got to the hot tub, I stripped off my clothes and we walked up the steps.
“This may be ‘your day'” Sherri said, “But after that, you owe me.” Sherri sat on the edge of the hot tub and put her feet in the water up to her knees. Then, she leaned back and spread her legs. I took the hint and continued into the hot water, moving myself so that my shoulders were between her thighs.
I leaned forward and took my first lick up her slit. She was already nice and wet from the last few minutes of activity and I could taste the sweet and salty mix of her arousal. I danced my tongue over her clit and used two of my fingers to start moving and out of her pussy. Using my tongue, I licked down one side of her outer lips, across my own inserted fingers and up the other side. Every time I reached her clit, I would stay there and gently flick and lick over it. I kept my fingers at a slow, determined back and forth pace, focusing my efforts on the pattern of my tongue. Sherri had a solid grip on the back of my head and was starting to force me tighter against her.
I kept up this rotation and pattern for another minute or so before changing things up. I adjusted my wrist and got my fingers pointed up inside her vaginal walls, searching for her g-spot. Meanwhile, my tongue stopped it’s long licks and I bared down on her clit. I had read ages before that when giving a woman oral a great trick was to trace the letters of the alphabet on her clit, so that’s what I started to do. Very slowly, very lightly, I started to lick in a deliberate pattern…. A….b…..c….. At the same time, found the silky soft pocket of her g-spot and began to gently rub it with my finger tips.
Sherri started to buck her hips against me as her orgasm started to build. K….L….M…..N…….
To push her over the edge, I took her clit between my lips and started to suck on it, keeping up the efforts with my tongue…. S…..t……u
That did it. Sherri’s pussy flooded my mouth and she bucked and moaned, keeping a tight grip on my head. I could feel all her muscles contracting, from her legs to her hips to her pussy. Her moans build to low screams as her legs thrashed in the water of the hot tub and I did my best to desparately hang on.
“Fuck! Jay! So….good! Fuuuuuuuuuck!”
I’m not sure how far down the Caribou Trail Hal & Donna had walked, but if they were anywhere close, I’m pretty sure they knew what was going on. As Sherri started to calm down, I slipped backward into the hot tub and dunked my head under to rinse her fluids off of me. When I came up for air, Sherri was still sprawled on the edge of the hot tub, her legs spread, pussy red and inflamed still leaking juices, and her breasts flushed with rock hard nipples.
She opened her eyes and saw me sitting in the hot tub and started to slide in, letting the hot water envelop her body. She floated over the other side and propped herself on the edge on her elbows, with her ass facing toward me. The position had her head, shoulders and tits over the top of the railing, giving her a view of the resort.
Looking over her shoulder, she said, “Fuck me from behind. The water makes it tough, but I want to try something.” She raised her hips above the water and I approached her with my hard cock leading the way. Grabbing her wet hips, I was able to find her opening. The water had washed away some of her natural lubricant, so I rubbed my cockhead against her until I could feel it getting coated. Once her juices were flowing, I started to slide into her. Her recent orgasm made her tighter, but I was able to press against her until my balls were against her.
“MMMMMMM….that feels good. Now, fuck me slowly.”
Following her instructions, I began stroking myself in and out of her. One of the things I always loved about doggy is that I can look down and watch Sherri’s pussy lips grip my cock as it moves in and out of her. That’s exactly what I was doing as I slowly watched her lips grip and pull in as I thrusted forward, then stretch out and extend as moved back. Unable to help myself, I started to pick up speed, despite her instructions. I was fucking her faster, sending waves splashing out of the hot tub. We were both grunting and moaning when Sherri spoke up again.
“Push all the way in and then stop. I want to try something.” Again, I followed directions, rammed my cock in as far as it would go and stopped. Sherri shifted her weight up to her arms and pushed back against me. She told me to move lower into the hot tub with her, staying inside her pussy. It was awkward to keep my cock in her plus my balance on the slippery floor of the hot tub. I couldn’t figure out what she was trying to do until she settled a bit further back and I felt it.
Sherri had moved lower so that one of the jets was hitting her directly on her clit. I could feel the water hitting her, then rolling down and under my cock to my balls. The hot tub and I had become one giant vibrating dildo for Sherri. With all this stimulation, her orgasm was nearly instantaneous. Her hips began to buck back against me while she tried to maintain her grip on the side of the tub. I ended up wrapping my hands under her tits just to keep her above water.
“Fuck me. Fuck me harder!” she yelled. I picked up the pace and waves of water kept splashing over the side of the tub. Sherri was slamming her pussy back into me as she tried to ride both me and the pulsating water jet at the same time.
“That’s it! Fuck my pussy! Fuck it hard! I’m going to come!” At that point if anyone had been walking by the chalet, they would have heard and possibly seen us, but neither of us cared. Sherri’s orgasm started to rip through her just as the pressure in my balls became too much. Her pussy was spasming around my cock which began to pulse and shoot my cum deep inside her. I had been hard off-and-on for hours, looking at her naked body stretched out in front of me and now that tension was releasing itself inside her. I grunted a final time and felt myself slip out of her. We both sat in the hot tub for a moment, but the exertion combined with the heat wasn’t doing us any good. Both of us were having difficulty getting our breath back.
I was the first to move, lifting myself out of the hot tub. The cool air coming over the railing felt great and I reached out to Sherri to get her out of the hot water.
“I can’t believe I’m saying this” she started, “But I really need to cool down a bit.” With that, she stood up, bracing herself against the wall of the chalet. For the first time that day, she was completely exposed to anyone who could have looked over to our deck, but I could see her body reacting to the cold air finally hitting it. She lasted for about a minute before announcing, “I’m going to take a nap upstairs. Wake me later.”
I let Sherri sleep for a few hours and started to think about dinner…and the next phase of my “What I Say Day”. I went upstairs and woke her up, telling her that if we wanted dinner, we had to run to the store to get some groceries. She groggily agreed and went into the bathroom.
I started to get dressed when the bathroom door flew open and I saw Sherri staring at me.
“What do you mean WE are going to the grocery store?”
I smiled and replied, “Yup. Both of us. Going to the grocery store. I was thinking some scallops, rice, maybe a salad?”
“I’m not going to the grocery store naked!”
“Of course not. That would be insane and get you arrested. But I do have a plan!”
“Oh, do you?” Judging by her tone and her reply, I got the sense that Sherri was fully on board with my little game, finally willing to play along and take some risks.
“Of course! Do this. Put on those socks you had on last night and your boots. I’ll take care of the rest. Meet me downstairs.”
“Fine. But I want to know the plan before I walk out of here, otherwise forget it.”
A few minutes later, Sherri came down the stairs looking sexy as hell. She had the socks back on, pulled up to her thighs and her hiking boots on her feet. Despite all the sex so far that day, I could feel myself getting hard all over again. I handed her the parka she had brought with her and told her to put it on.
Sherri took it and sighed, “This won’t work. It only comes to my hips and won’t cover my ass or pussy.” She put it on and she was 100% right. The cut of the parka was too high and left her exposed.
“OK” I said, “Take it off and put mine on instead.”
Sherri did as I asked and lo and behold, my plan had worked! My parka was definitely big on her, but it completely covered her top and extended almost down to her knees. When she zipped it up, she looked like she just had on some ski outfit underneath a big parka. Nobody would be able to tell she was basically naked under it.
I grabbed the heaviest sweater I had, my keys and her hand and we went out to the car. It took a few minutes for the car to warm up and despite that she had on next to nothing, Sherri was actually warmer in my parka than I was in my street clothes. Once the car warmed up, I started driving to the store that was about 15 minutes away.
Even though it was still early, the sky was kind of dusky at that hour. After we had been driving for about 5 minutes, I looked over and said, “Ok. Car is nice and warm. Unzip the coat.”
At this point, Sherri had committed to the day’s game and just rolled her eyes at me. She undid her seatbelt, reached up and completely unzipped the jacket, exposing her skin from her collarbone to the tops of her stockings. She tucked the jacket to her sides and buckled back up. The road was a full of curves and Sherri caught me glancing over at her a few times.
“I’ll stay like this, but you need to keep your eyes on the road, Jay. If we go off the road, I’m not explaining this outfit to the local cops.”
We continued the drive and although I tried, I still couldn’t resist glancing over at my girlfriend’s exposed body in the seat next to me. As we approached the grocery store, I pulled up to a stop light and slid into the left-hand lane to make my turn. As I did, a large pickup truck pulled up in the lane next to the car. I didn’t think much of it until I heard a horn start beeping and what sounded like a bunch of teens whooping and hollering.
I looked over and there were three young men in the truck next to us, crawling over each other to get a better look out the driver’s window at Sherri’s body. It was then that my girlfriend, who was mortified at the “rules” earlier in the day, did something I never expected. She unbuckled her belt, turned toward her window and wiggled her tits at the men. The light turned green and I heard a mixture of more yelling, more beeping and Sherri laughing as we made our turn. Sherri zipped the coat back up as we pulled into the grocery store.
Once we were in the store, nobody gave us a second glance as we started to fill the basket. We looked like two people who were grocery shopping after a day outside. When we went to the produce section, Sherri picked up a long carrot, held it up and asked if we needed one for dinner.
“Nope. No carrots.” I replied.
“What about zucchini?”
“No. I’ll get what I need.” I was still oblivious to her shenanigans as I was focusing on getting everything I needed for dinner.
Then Sherri walked over to me and got very close. She leaned up and whispered in my ear, “What about a big cucumber? Should I get one of those? I mean, is it really shoplifting if I shove it inside me under this coat?”
I was literally dumbstruck, unable to reply. Sherri simply walked away with a smirk, put the cucumber back, and motioned for me to follow her with her finger. As I started to follow her around the corner to the next aisle, I had to adjust the basket I was carrying to cover my erection in my jeans.
We wandered through the entire store, I kept grabbing what I needed for dinner until we took a turn down the aisle that had “personal products”, baby supplies and the like. Seeing it was empty, Sherri quickly said, “Get your phone camera out.”
I fumbled for my phone and got the camera up JUST as Sherri turned to face me from down the aisle. She had unzipped her coat and was giving me a full-frontal flash. I hit the button to take as many pictures as I could before she closed the coat and continued walking. Sherri was much more flirtatious, constantly rubbing up against me as we walked. At one point, while we waited at the seafood counter, Sherri took my hand that she was holding and ran it up under her coat to get a quick grab of her bare ass. Just as the clerk turned back, she dropped my hand and her coat.
We ended up in the frozen section where there were still a few people shopping. Sherri took me by the hand and kept me close. All of a sudden, she stopped and opened one of the frozen doors by the ice cream, letting her coat fall wide open. But because it was so big, nobody to her sides could see her reveal anything because it hung down on both sides like a set of curtains. When she did it though, she took a blast of cold air directly on her naked body. Then, with me right behind her she bent over to get a container of ice cream from the very back of the case.
From my view, I could see the coat ride up and give me a glimpse of the bottom of her ass cheeks. To everyone else, the coat and my body blocked their view. Sherri stood back up, gripping her coat closed and handed me the ice cream. Leaning in again, she whispered in my ear.
“Fuck, babe. My tits and pussy are soooooo cold right now. Too bad you can’t warm me up right now.” As she talked she reached into the pocket of my jeans, running her hand over my rock-hard cock. Right when I thought she was getting a better grip, she pulled out my car keys.
“OK!” she laughed. “I’m done shopping! See you in the car!”
With that, she almost skipped out of the store, leaving me stunned, flushed and sporting an erection that the basket was barely concealing. I was able to finish the shopping and made my way out to the car where she was sitting, bundled in the coat, with the heat blasting.
“Wow. That was just mean!” I said placing the bags in the back seat.
“Seriously? You have me parading around naked all day and take me into a store like that and I’m the mean one?”
“Still though…”I whined as I started to pull out of the parking lot.
“Huh. Maybe you should have thought of this when you set the rules for today. It’s not my fault you have me naked in places where you can’t take advantage. Like, when you are driving the car?”
Her tone made me look over to see that she had unzipped the coat again, but this time had her legs spread up on the dashboard. As I waited for the light to turn green, she slowly licked two of her fingers and ran them down to her exposed slit. She had one slowly moving in and out of her pussy, while the other one feathered her emerging button.
“BEEEEEEEEEEEEEEEEP” I almost hit my head on the top of the car when I jumped at the sound of the horn behind me.
“Light’s green, babe.”
As luck would have it, there was not one red light or stop sign on the ride back to the chalet which became the longest 15 minutes of my life. Sherri was taking advantage of the situation and continued to pleasure herself. The scent of her arousal was starting to fill the car and I could hear her wetness as she stroked her fingers in and out of her pussy. If the sights and scents weren’t enough, she decided to add more sound to the situation.
Sherri started rolling her hips and moaning and grunting next to me. She had moved one hand up to her left tit and was grabbing it while rolling her nipple in her fingers. Her other hand kept up the rhythm in her pussy, occasionally going back to rubbing her clit.
“I think I like this” she moaned. “Being on display like this. Uhhhhhh. Thinking about people looking at my tits and pussy. Ohhhhhhhh. I was getting so turned on in that supermarket, babe. I wanted to find a place to fuck you right there. Mmmmmm. Just lift up my coat and stick that cock in my soaking wet cunt.”
I knew Sherri was getting close as her language got more course. Her hips were rolling and bucking against her fingers as her orgasm took over.
“Fuuuuuck. Oh my…… fuck. Fuck. Oh, fuck.” Sherri was panting and gasping for air with her fingers still deep inside herself. She was getting hit with some aftershocks of her orgasm as we pulled into the parking spot of the chalet. Sherri’s eyes fluttered back open and she said, “Perfect timing.”
With that, she opened the door of the car and got out, this time not bothering to close her coat or cover herself up. As I lifted the bags from the car, I saw Sherri turn to face me, smile and drop my coat on the walkway. She then walked the final 25 feet to the door completely exposed while waiting for me with the key. I picked up the coat on my way, opened the door and she strolled in.
“I’m going to sit with a glass of wine and read while YOU make dinner” she declared. With that, she poured herself some wine, grabbed her Kindle and settled back on the couch by the fireplace. The difference in her comfort level from eight hours earlier was startling.
As directed, I made dinner and announced that it was ready about an hour later.
“I have one request” Sherri said as she walked over to the little table. “I want you to be naked for dinner too.”
I thought about pushing back with the “rules” of the day but decided against it. Sherri had been an amazing sport all day and was now actually seeming to enjoy herself (both literally and figuratively). So, after I put the plates down on the table, I peeled off my clothes and sat next to my beautiful, naked girlfriend at the table.
We enjoyed the dinner and dessert and had a normal conversation. We talked about the rest of the weekend and what we had going on when we got back. Our nakedness certainly kept a higher level of eroticism in the air, but it wasn’t overt. At one point, I reached over to give Sherri a kiss on the cheek and I gently stroked her nipple. At another, I felt her foot sneak under the table and start to massage my cock. Throughout dinner, we both managed some subtle grabs, strokes and pinches just to keep each other aroused.
We finished the chocolate cake (that admittedly we bought pre-made in the grocery store bakery) and some glasses of brandy, full & satisfied. Sherri’s foot had worked its way back to my crotch and she was gently rubbing me getting me hard again.
“What do you say we head upstairs and finish the night right?”
Sherri didn’t have to ask me twice, I stood up and started up the stairs with Sherri following closely behind me. As we reached the loft, I went toward the bed but Sherri reached over and flipped the switches opening up all the blinds in the chalet. She then turned on all the lights in the loft. For anyone looking from above or outside in the dark, the entire bedroom was completely lit up and visible.
Sherri strutted over to the bed and climbed on top of me.
“I thought that we would finish your ‘What I Say Day’ the right way” she said as she lifted her hips and lined my cock up with her wet tunnel. The teasing all through dinner had us both ready without any additional foreplay. My cock was rock-hard and her pussy was well-lubricated. I slid in effortlessly and grabbed on to her hips as she started rocking her pelvis back and forth. Sherri’s hands were on my chest, allowing her to control the speed and friction of her motions.
Sex this time was the complete opposite of our frolic in the hot tub earlier. Where that was fast and raw and rough, this was slow and deliberate. With all the lights on, we were able to look in each other’s eyes and see every inch of each other’s bodies. I caught myself looking up and out through the windows of the chalet, wondering who might be out there.
“You think anyone is watching us?” said Sherri, obviously thinking the same thing.
“If they are, you’re giving them a great view.”
“Mmmmm, babe. I have to tell you, when this all started today, I thought you were insane. But as it went on, I have to say I was getting pretty turned on.”
I loved hearing Sherri talk about sex, so I wanted to encourage her to keep talking while she gyrated on me.
“Yeah? So, you liked it after all? What changed?” Sherri shifted a bit and leaned back, bracing herself on her arms back by my knees. It actually opened her up to me a bit more so I could see her pussy enveloping my cock and her clit peeking out at the top of her slit. I licked my fingers and started to gently massage her button as she slowly rode on top of me.
“I think it was when we were out on the deck. Depending on how I moved, I kept getting hit by a mix of warm and cold air all over my body.” She paused, “Play with my nipples.” I reached up and cupped her b-cup tits and used my thumbs to run small circles around her erect nipples.
“Yeah, that feels amazing. It was the cold air on my tits that really got me. When that couple…”
“Hal and Donna?”
“Whatever. When they surprised me and I sat up, I was definitely embarrassed, but the way the cold air felt on my skin had me too aroused to even think about it. Then, having you go down on me by the hot tub, then into the hot tub, it was just so much.”
Sherri was picking up speed now. She dropped all the way forward so she was laying on my chest. She started pistoning her hips up and down, driving herself down on my cock.
“Once you gave me that outfit to wear at the store, that was it. I was so fucking turned on, my pussy was dripping the minute we left the house. Oh….that’s it. That’s so good. Fuck me, Jason. Fuck me as hard as you can.”
I started to meet her thrusts with hip movements of my own, driving up into her.
“Is it turning you on?” I asked. “Knowing that everyone can see you getting fucked right now?”
“Yes. Yes!”
“The same people who saw your tits and pussy on the deck? And the ones who saw your ass at the store? You think they’re watching?”
“Oh, yes, Jay! Fuck me, I’m so close.” I was pounding up into Sherri now, gripping her hips to give as much power to our thrusts as I could.
“Right now there are men watching you from their rooms, jerking off, wishing they were the one fucking you right now.”
“Mmmmmm….keep going.” We were at a fevered pace now. I had a firm grip on Sherri’s ass cheeks, and she was kissing and biting at my neck and shoulders. The sounds of her pussy slapping down on my cock were filling the room. I could feel her juices flowing out of her, down my shaft and balls.
“Maybe that woman is down on her knees, sucking her husband’s dick? While he’s thinking about how tight your pussy is.” I shifted my hands a bit and used one of my fingers to spread a bit of moisture around Sherri’s asshole. I didn’t insert it, but I started running it in circles around her tight rim.
That did it. Sherri let loose a howl and began to come on my cock. She was thrashing and pounding down on me.
“Please Jay. Come in me. Fill my cunt up with your cum. I need it. I want everyone to see you fill me up.”
I couldn’t hold back anymore and my final load of the day exploded out of me and into Sherri’s depths. She kept grinding against me as I spurted more and more until I was finally drained. Sherri slipped off of me, leaving a trail of our mixed fluids on my thigh. We laid side by side for a few minutes until Sherri started to get up.
“OK. Day’s over. I’m getting changed into my PJs. You close those blinds and turn off the lights.” As she closed the bathroom door, she made sure to add, “And you better be real careful with any bets you make for a while because payback is gonna be a bitch.”
That night, I slept like a rock and woke up late the next morning. Sherri was not in the bed, and I could smell coffee brewing downstairs. I went downstairs and didn’t see her anywhere. I poured myself a cup and went over to the sliding doors by the deck. I looked outside and Sherri was back in her lounge chair. She had on a bathrobe, but it was untied and open showing her breasts and a bit of her landing strip. I slid the door open and Sherri turned to look at me.
“You know the bet ended yesterday when we went to bed, right?” I asked.
“Sure. But we have a few more days here, so I see no reason why we can’t continue the tradition when we’re in the chalet. But, I’m telling you right now that tonight, you are taking me out to the lodge restaurant where you are buying me a very expensive meal and I will be wearing all my clothes.”
Then, with a wink she added, “Well, maybe not ALL of them.”
Author’s Note: Hope you enjoyed my twist on “Nude Day” — please rate the story and leave feedback! Thanks for reading!