A Christmas Caroling

Winter Holidays Story Contest 2023 Submission

Please kindly rate my story and leave me comments, I would like to hear what you all have to say, constructive criticism is welcome. If you want to troll and be nasty in your comments I will ignore them and it will be a waste of your time. This is fantasy fiction and I choose to have no STI's in this world. All participants in sex acts are 18 years old or older and similarities in names or descriptions of the characters are purely coincidental and are not based on any real person living or dead. Please enjoy!

Thank you,

-Joker

A Christmas Caroling

My wife Carol has a slight gambling problem. Now she doesn't go out and blow all our money at casinos or on lottery tickets and the like. No her gambling problem stems from our childhood and I guess you could consider me an enabler.

My name is Mike. Carol, my wife, and I grew up next door to each other. We were thick as thieves growing up given that our parents were less than reputable in our town. Not a soul that knew us ever doubted that we would be together forever. Since we knew each other since we were kids we got along well enough, but we had our share of fights.

That's where the gambling comes in. As children after a really bad fight in junior high school, we decided that we would never fight again. However, we would need a way to settle any disagreements before they blew up into a fight. Our fathers were both card players, always running games at one of our houses.

It was there that both Carol and I learned various styles of Poker as well as Blackjack. So we had decided that we would play three hands of either Poker or Blackjack, best two of three wins. Whoever won, won the disagreement and the other had to go along with it.

Over the years this way of deciding arguments evolved. We still used it for disagreements, but now my wife uses it to get or do things that she wants. I was lucky in this aspect as my father had taught me to count cards and stack the deck. This always gave me an edge over my wife.

I wasn't an ass and took advantage of her, I picked and chose my battles. As our game of decisions evolved into a way for my wife to get things she wanted, we reworked the rules a bit. If it was just a standard argument the regular rules would be in play, but if the game was to be used for my wife's wishes then we would use a different set of rules.

If my wife won then she would get what she wanted or we would do what she wanted. If I won, obviously she wouldn't get what she wanted or we wouldn't do what she wanted. Since this was her way of getting what she wanted, I had proposed that if I won she would then have to do whatever I told her to do for a whole day of my choosing.

Carol agreed to these conditions and our little game of decisions became a fairly regular occurrence. I let my wife win most of the time as long as the things she wanted weren't some big life-changing or costly item or event. Sometimes I'd just let the games play out naturally.

She wanted a puppy and thought I would be opposed to it, I had no problem and let her win. She wanted to buy a sports car, I won that game as we weren't that financially secure at the time. This is how our games played out and how it led to a pretty fun and eventful night.

It was early November and my wife was watching Christmas movies on the Hallmark channel. This always bugged me, it was too early for Christmas stuff and it seemed like just last week Hallmark had their Christmas in July. Carol was watching a movie that was set at an Ice Hotel, where the hotel is made out of ice.

Well, she got the idea that for our Christmas Vacation this year, we should go and stay at an Ice Hotel. I wasn't very fond of this idea but knew at this point in the year that she would never be able to book a stay at an Ice Hotel. So I let her look into it. She was disappointed of course when she couldn't find any openings.

In her infinite wisdom, she broadened her search and presented me with spending two weeks in the Alaskan wilderness in a tent at some sort of outdoor retreat. I looked at her like she was out of her mind, at which point she got up walked out of the living room, and returned a few minutes later with a deck of cards and placed them in front of me.

"What's the game?" I asked.

"Texas Hold 'Em," my wife stated.

"Who's dealing?" I inquired.

"Let's cut for it!" Carol proclaims. So I shuffle the deck and push it in front of her. She cuts the deck in half putting the bottom half on top. I reach forward cut the deck and pick up about one-third of the cards. Carol reaches out and grabs a small stack as well. We show our bottom cards to each other. Carol has a Seven of Hearts and I have a Jack of Clubs. I deal.

"What's your part of the bet?" I ask as I begin shuffling.

"If I win, we spend our Christmas Vacation at the outdoor retreat in Alaska," Carol says with a smug look on her face. She must be feeling confident. I am confident that I will not be freezing my ass off for two weeks. Not that it would be much warmer here in Syracuse, New York.

"Okay, and as usual if I win you have to do whatever I say for a whole day of my choosing. Agreed?" I questioned.

"Agreed!" My wife said as she nodded her head.

I let her win the first hand and then I won the last two. We would not be spending two weeks in Alaska over Christmas. She was definitely upset that we would not be in Alaska for vacation.

"Why don't we go to Costa Rica instead. It will be nice, warm, and sunny" I offered.

Carol's frown went away and she now seemed pleased at our new destination. "Okay, I like that idea too." My wife says. "So what do I have to do for you?"

"I haven't decided yet, but I'll let you know when I do." I smile and then begin to think of a worthy punishment for my wife.

The weeks passed by and it was getting closer to our Christmas Vacation trip and I still hadn't come up with any idea on a punishment for Carol yet. As I sat at my office desk pondering what on earth I could have my wife do, the restaurant manager knocked on my door and peeked his head in.

"Hey, Mike. Do you have a moment?"

"What's up, Dan?" I asked.

"There is a lady here from a local Church Choir, and she was wondering if we wouldn't mind letting them sing Christmas Carols outside the entrance?" Dan inquired.

"When and for how long?" I replied.

"She says starting on the twentieth til the twenty-fourth from 6:00 p.m. to 8:00 p.m," Dan stated.

"Sure, no problem. Just make sure they know we are closed Christmas Eve!" I answered.

"Okay, thanks," Dan said as he headed back out front.

Christmas Caroling huh! Now that gave me an idea. I quickly started looking up Christmas Caroling and found out that December 20th is Caroling Day. That would make sense as the Church Choir asked to start on the Twentieth. I then checked online to see if any local groups would be caroling that night.

Sure enough, there were quite a few groups that would start caroling on the Twentieth, and one of them would be meeting up in our neighborhood. I visited Amazon and ordered a Christmas suit for Carol to wear as part of her punishment that I now had planned.

It was getting late in the afternoon and I still needed to check in with our other restaurant across town. So I decided to call and check in, instead of heading over so late in the day. Carol and I had worked hard to get to where we were. Once we graduated high school, we got married and moved away from our deadbeat parents.

It wasn't easy being on our own but we worked hard. One day on a whim Carol dragged me into a Ralph Lauren outlet store. This stuff was way overpriced for what we could afford, but I went along with her anyway. My wife and I looked around until we came to a clearance rack we started going through it and found some really great bargains.

I pulled my wife outside so that we could talk out of earshot from the store employees. It was then, that we made a huge decision and maxed out our credit cards by purchasing all the clearance stuff we could. We then started selling the clearance items online for more than we paid but less than the original retail price.

Thus our first business was born. Once we had started banking a lot of money from our online store, we decided it was time to get into a brick-and-mortar business. We found a good chef who was doing well with a food truck and bought him out, hired him as the head chef for a restaurant, and kept the food truck for catering purposes.

With a successful restaurant under our belts, we decided to open another using the same criteria. So now at the age of twenty-seven my wife and I owned an online shopping store and two restaurants with catering businesses. We were doing quite well for ourselves which allowed us the freedom for Christmas Vacations.

Three days had passed and I got home Monday evening to find a package on the armoire by the front door of our home. I knew exactly what it was and brought it into the kitchen with me where Carol was cooking dinner. I set the package on an open counter and started looking for a pair of scissors to open the box.

My wife walked over and kissed me, "Good evening honey." Carol said to me, "Did you get me something?"

"Actually it is for you and it's multipurpose as well," I answered.

"Really! What do you mean?" My wife inquired.

I started opening the box as I explained it to her. "You see, this is something for our trip to Costa Rica and it is also going to be used for your loss in our decision game last month."

"Oh... I thought you had forgotten about that," Carol stated.

"No, I didn't forget. I just couldn't think of anything until a couple of days ago." I smiled, "So the thing that I want you to do Wednesday night, is go Christmas Caroling wearing this!"

From out of the box, I pull out a red bikini with Ho-Ho-Ho written all over it in white. I showed it to my wife.

"No Mike! Absolutely not! It is too damn cold out to wear a bikini around outside." Carol decreed.

"I'm sorry, Darling. But you know the rules, you have to do anything I want for one whole day of my choosing." I reiterated the rules to her, "I am sparing you and you only have to do this for two to three hours tops."

"But Honey, I'll freeze to death!" My wife exclaimed.

"I'll tell you what, you can wear a knee-length winter coat while we walk from house to house. But you have to take the coat off while you sing. That's the best I can do." I told her, compromising just a little bit.

"Well I guess that's fine, but I'm definitely going to get a Brazilian wax tomorrow and pamper myself at the spa. I don't want any pubes showing while I sing Christmas Carols." My wife declared.

"That's fine with me. I can't wait to see you wear this while caroling and while we are on vacation." I stated.

The next two days seemed to drag on forever as the anticipation of my wife's punishment drew near. Earlier I had printed out some carols in large lettering for my wife to use as reference. I left work early and got home around 4:00 p.m. Carol and I had an early dinner as I explained that the Carolers that we would be shadowing should be coming by around 6:00 p.m.

Right around half past five Carol went upstairs and changed into the Christmas bikini, she looked absolutely stunning in the red and white bikini. The bikini top barely contained her perfect 36C breasts. They stood proudly upon her chest with hardly any sag, and her nipples were quite erect, it was either from the cooler air or she was excited.

The bikini bottoms covered her vulva, but it was apparent that she had no pubic hair as the thin material clearly showed the outline of her lips. In fact, you could tell she was excited because could just make out the bump of her clit protruding out from under its hood. My cock began to twitch in excitement.

Further down my wife was wearing a pair of over-the-calf black leather boots with a two-inch heel. As she spun around to show me her backside her beautiful ass was barely covered at all. It was dangerously close to looking more like a T-back or a G-string. My wife was gorgeous and would definitely get plenty of pleasing glances tonight.

A little after 6:00 p.m. there was a knock at our door. I was sure it was the carolers. I yelled out to my wife and she came to the door wearing a puffy white knee-length winter coat. I opened the door and the carolers began to sing. We listened to them sing a couple of songs and then they moved on to the next house.

We waited for them to get down the block aways as we didn't want to be too close to them as Carol partook in her punishment. We were pretty private people so we didn't know anyone on our street with the exception of our immediate neighbors. We were too busy to hang around and be chummy with all our neighbors.

We had a core group of close friends and they didn't live in this neighborhood, so we didn't have to worry about being recognized by anyone other than our immediate neighbors. With the other carolers far enough away we ventured out and down the street.

We walked up to the front door of the first house and rang the doorbell. I took my wife's coat and she began to sing 'Frosty The Snowman,' a little old lady and her husband opened the door. The old lady yelled out 'Hussey' at my wife and slammed the door in her face, the old man had a grin from ear to ear.

Carol put her coat back on as we chuckled. The next couple of houses pretty much reacted the same way, mostly parents not too happy that their kids saw a half-naked lady singing Christmas Carols. Finally, after a half dozen tries we got to a house where the owners enjoyed my wife's singing and attire.

Once Carol was done singing 'Silent Night' the wife complimented my wife on how bold she was and how she would like to try it as well. Her husband handed me a business card and told me to call them next year if we wanted another singer. We thanked them and told them we would be in touch.

The next couple of houses were equally as receptive and Carol was really starting to enjoy it as much as the people she was singing to. Eventually, as the night got later the people that my wife was singing to really started to get into it. We climbed up the steps to the front door of a nice colonial, their front yard was brilliantly lit up in Christmas decorations and the lights shimmered across the snow.

I took my wife's coat once again as she began to sing 'Santa Baby.' A gentleman in his mid-forties answered the door. "Holy Shit!" He shouted, "Ginny! Come quick you got to check this out!" A few seconds later his wife came running down the stairs.

"What the!" The wife gasped.

"Pretty fuckin hot right!" He said to his wife.

"Fuck yea!" She replied and then started filming my wife singing in her Christmas bikini. Carol moved on to 'Chestnuts Roasting on an Open Fire.' I couldn't help but notice that the wife's nipples were getting hard and her husband was beginning to rock a serious erection.

When Carol finished the song we wished them a Merry Christmas and headed to the next house. Now judging from what happened next; I can only assume that the neighbors started calling each other because every house we went to after, the occupants were ready and waiting with phones in hand.

At the next house, we were greeted by a couple in their late thirties by my guess. They already had their door open and phones recording. My wife handed me her coat and before she could even start singing, the gentlemen spoke right up. "Wow, would you look at how hard those nipples are!"

"Jesus! You could hang stuff off those nipples." The guy's wife exclaimed.

Carol began to sing 'Jingle Bell Rock,' when the guy shouted out. "Bounce them titties!"

"Yeah! Make 'em rock to the song!" The lady shouted as well.

I was surprised that my wife started bouncing her tits and adding a little sway as she sang. Her gorgeous ass was swaying in front of me and I could feel my dick starting to grow. She then switched to 'Little Drummer.' When she stopped singing we wished them a Merry Christmas.

"You have a Merry Christmas as well!" The lady replied.

"Thank you for the entertainment! Your tits are perfect!" The guy added as we turned to walk to the next house.

We had noticed that we had kind of caught up a little to the other carolers so we hung back a bit and took our time going to the next house.

"Mike, this is really starting to turn me on. Those two couldn't stop staring at my boobs." Carol announced.

"Well, you sure were shaking them quite a bit." I commented, "And you looked like you were enjoying yourself as you did it."

"It is more fun than I thought it would be," my wife remarked.

With a little more space between us and the carolers, we went to the next house on the street. No surprise as the next people were waiting for us. Carol handed me her coat and I noticed that her areolas were starting to show. Bouncing and shaking her tits before most have moved her bikini top some.

As she sang she was more animated with her movements and was putting on a good show with her gorgeous tits bouncing about. The couple at this house were recording my wife as well and both seemed very pleased with her performance. The husband leaned into his wife and whispered something in her ear.

The wife smiled and lightly nodded her head. Carol had moved on to her second song, 'It's Beginning to Look a Lot Like Christmas.' I stood just behind her and slightly to the right so I couldn't see that her tits had sprung completely out of her top.

When she stopped singing the lady pointed out that her tits had popped out. "Oh dear, Miss. It looks like your breasts have come free of your top. Let us fix that for you." Much to my surprise both the lady and her husband reached out, each of them grabbing a breast and slowly and carefully adjusting her top back into place.

"O-oh. Thank you. Have a Merry Christmas!" Carol said to the couple and then turned to me. We headed down the walkway and back to the sidewalk. Carol stopped and looked at me. "That was so freakin hot! I didn't realize that my boobs had popped out and then when they touched my tits, I just about creamed myself."

"Did you like showing off your tits to strangers?" I asked.

"I did! It felt exhilarating. I want to do it again!" She exclaimed.

"If it makes you feel good then you should," I told her.

We got to the crosswalk and checked the street before crossing over to the next house. When we were safely on the sidewalk Carol opened her coat and moved her bikini top to the sides so that her nipples were uncovered but her breasts were still partially covered.

When we started up the walkway to the house the door swung open and we were greeted by a man in his early fifties. Carol handed me her coat and strode right up to the door and started singing. The man had a handheld digital video camera and was quite intent on filming my wife's boobs which by the shaking she was doing had to be completely exposed by now.

As she started singing the second Christmas Carol I noticed the man pan down her body and focus in on her pubic area. This excited my curiosity. Once she had finished and wished the gentleman a Merry Christmas, he spoke.

"You know, you have a gorgeous rack and you should just ditch the top completely." Then he added, "By the way, your bottoms are soaked!" He then closed the door.

My wife turned to me and her face was beet red. I looked down at her bikini-covered vulva and saw that they were indeed drenched.

"You must really be enjoying this," I remarked. All she did was nod in a cute little embarrassed kind of way. She took her coat and put it on her but didn't close it, instead, she readjusted the top once again to where her nipples were slightly exposed. And we were off to the next house. A young couple were waiting on us at this house, phones already recording.