Christmas Holiday Challenge

This was a new twist to holiday gift giving -- my wife and I agreed that we were up for a change. Each of us prepared twelve challenges for one another. One for each day of the twelve days of Christmas.

You should know that we weren't your average plain-Dick-and-Jane-couple. For the past five years of our marriage, we had loosened the boundaries of our relationship and our sex lives. I started it, but Claire picked it up and ran with it. It began when she walked in on my home office to find me jerking off to internet porn. At first, she was affronted, but then that rebellious spark that I fell in love with initially reared up.

After I shared my interests, we went exploring together. Turns out her interests were even more varied than mine.

There are many things that had happened in the five years since then -- enough for more than a few more Literotica chapters one of these days -- but, summing it all up, we were having more sex with more people than we had in all the years before we met. We had our groups together and apart. Through it all, we continued to look to have it be more interesting. Then came the Christmas season. I came up with the idea after reading through some blogs on Tumblr where challenges were being enumerated ("Give a stranger a blowjob and film it for your partner" and the like.)

"Okay, Claire, how about this? We each write up twelve challenges for the other, and present them for the twelve days of Christmas."

"I like it. But let's think -- what if we don't complete them? What will be the penalty?"

"Damn. I hadn't thought about that. Do we need a penalty? Can't we just promise to do everything?"

"I have some ideas you might be hesitant to try -- and you might have a few for me -- so what do we do to guarantee that all the challenges are met?"

"Well, we either promise to do them all or let's not even bother. I'm game if you are."

And that's what we did -- we decided to go ahead even though we each had some delightfully wicked thoughts about pushing each other's boundaries. (We did agree that some things were out of bounds -- no scat, no physical harm, and nothing risky.) And then we had about a week to come up with them for each other.

December 14 -- the first day of Christmas

This was our first challenge day. I had spent the past week making list after list of challenges for Claire, and slowly whittled them down to twelve. She -- as it turns out -- had done exactly the same.

We went out for dinner that evening, meeting after work at a favorite restaurant with a romantic setting. Candles, low key jazz and a multi-course dinner with plenty of wine had us both satiated and glowing.

"It's time." I said, pulling out the card I had prepared for her. Claire did the same and we exchanged them. "Tonight, you open yours first so I can see your reaction; we'll change the order tomorrow."

With that, she used a dinner utensil to open her envelope. I watched as she read it. Her expression changed. At first, she was nervous and anxious. As she read the card her eyes grew wide. When she was done, she looked at me. Then she closed her eyes and another change came over her -- she must have imagined the scenario and I saw her face come alive as she opened her eyes."

Her first challenge, for the first day of Christmas, was to find identical twins and get spit-roasted between them. Picture were required for proof.

"How did you ever come up with this?" She asked.

"I just figured a pair was the closest I could get to a pear tree." I grinned awkwardly.

"It's a lousy pun, but a great challenge. Now open yours."

She'd been creative as well, and as it turns out, in a similar vein. I had to find a mother and daughter and satisfy them both. Together.

"And just how did you figure this one?" I asked.

"Pretty much the same line of thinking you used, actually. So, when do we start and when is this due?"

"As soon as the check is paid, and proof due by midnight, since we both have work tomorrow." She nodded and got herself together as I paid the check. Since we'd arrived separately, we left separately.

I didn't think mine would be tough to fulfill. We had a mutual friend (Geri) who was a little older, widowed, and with a single daughter in her late twenties. We'd encountered them both -- but separately -- through the years. I called ahead and determined that Geri was home alone but her daughter was expected in a bit, and I invited myself over.

Geri was in her early 50's, but you wouldn't necessarily notice it about her, other than a certain gravitas that comes with age and experience. She was a bit of a gym rat, since it not only helped her keep her figure, it also provided a ready sample of testosterone and cocks. Her daughter Marci, on the other hand, was less attendant to the hard body look and more the luscious, curvy type. I knew they both favored men and women -- I didn't know if they knew that about each other.

Geri met me at the door in a robe. Whatever was on beneath it was translucent as I glimpsed it.

"Hello, James, what brings you here?" She asked.

I explained to her about the challenge game Claire and I were playing.

"Oh, so you come over and expect me to simply drop what I'm wearing and fuck your brains out to prove something to your slut wife? How wonderful!" With that she peeled off the robe, gave me a moment to appreciate the blue negligee that she was wearing, and then that too slipped to the floor.

"Yes. That's right. I came to use you for sex. I came to turn you into a cum bucket. I came to come!" I had dropped my coat and was unbuttoning my shirt as she stepped forward and fell to her knees. Her hands went to my pants and soon they were on the floor, revealing my semi-erect, eight-inch uncut cock.

"Oh, thank goodness. I hate small talk and I love to fuck, I'm glad you remembered!" And with that she took the head of my cock in her mouth and soon her tongue brought me to full erection. Once I was hard enough for her, she simply lay back on her thick carpet, spread her legs and placed my cock at the entrance to her pussy.

"I'm wet already. Just shove it in and start fucking me like the slut I am!" Of course, I complied. We were busily banging when I heard the door open.

"Mother? How selfish! From the back, I'd guess that would be Mark, and you better be willing to share that big cock of his! Hello, Mark." As I said, we weren't strangers. "Did you know he and Claire have come up a set of challenges for each other for the twelve days of Christmas? Don't you think that's clever? And guess what? You and I are his first challenge. Get naked and get over here!" Geri and Marcie may have been closer than we thought....

"Do you mind if I pee first? I'll be right back. She stopped as she passed us to bend down and kiss each of us -- and she and her mother were definitely more than just mother and daughter. More likely mother and mother-fucker!

"Relax, James, and just keep fucking me. She'll be back and join in in a moment." What could I do? I resumed my long strokes in and out. And, a short while later, movement at the doorway caught my eye. There was Marcie, her large natural tits hanging down with their nipples extended, and belted around her waist was a dildo almost the size of my cock, bobbing up and down as if it were natural. She had something in her hands but I couldn't discern it.

"Marcie, before this goes further, would you take my phone and set it up to record this? It's part of the challenge." I asked. She went to my coat and took it out, then propped it up and made sure it caught the action before turning it on. Then she approached us on the floor.

"I'm so glad you want this recorded. I've wanted to do this for years!"

With that, I felt something cold and liquid in the crack of my ass, and then fingers were rubbing around my asshole. She was lubing my ass! At the same time, her mother was now more urgently pulling me into her pussy. I felt a finger move past my sphincter and begin to move, then, as I relaxed, another entered. And another. When they stopped, I felt her move closer and then I felt the tip of her dildo pushing into my back door. This was definitely not in my plans! As I moved into and out of her mother, that artificial cock at my ass began to move in and out of me. Or rather, I moved onto and off of it. As she pressed forward, it sank deeper and deeper into me until it was buried and I could only move back and forth for an inch or so. It was enough for Geri, whose orgasm was doing amazing things to my cock as Marcie's cock was pressing on my prostate. I lost control and felt the come rise out of my balls and into Gwen, and with Marcie jamming her dick up my ass, my prostate added a new level of pleasure to that orgasm. Strangely enough, I could detect that Marcie was also coming; evidently that harness made contact with enough of her to bring her off.

Getting separated was a bit sticky, but we managed. I spent another two hours with mother and daughter, during which I saw how they had developed a very unique bond between one another. Finally, I cleaned up, dressed and left. They enjoyed the holiday presents, I know.

Arriving home, I found Claire already in bed although far from asleep. As I came into the bedroom, she was naked on top of the bed covers, playing with herself as she stared intently at her phone screen. She looked up to see me, and slowed down to a stop. I was soon naked and we traded phones.

I didn't think it would be difficult to find twins, since we knew a few pairs of identicals from our circle. She had found the Chilton brothers (Alex and Nate), both of whom were still swimming competitively and therefore, in good shape. In addition, their cocks were about the size of mine. They too seemed to take to the task, and were delighted to record themselves in action with Claire. She did everything from sucking both of them at once, to DP, to fulfilling on the spit roast challenge. Then she had them both come on her face as she looked into the camera and said "Challenge one complete."

We looked at each other, high-fived, and fucked ourselves to sleep.

December 15 -- the second day of Christmas

It's time to tell the other side of this tale. James likes to think that he's in control. He thinks his dirty mind is superior to mine, but I've always been one for pushing the sexual limits. Don't tell him, but once I figured out where he was going for the first challenge, I called Marcie and gave her the suggestion to use the dildo. She loved it, and I can't tell you how I enjoyed seeing the expressions flash across his face as he realized he was about to get fucked. It's still one of my favorite videos.

So, we got to day two, after both of us found it relatively easy to fulfill on our day 1 challenges. I mean, really, he knew I knew twins, although the filming of the episode was an added kinky delight. But it was time to up the game. As it turns out, he was thinking like I was.

Dinner the next night was a simple meal at home, a little bit earlier so we each had time for fulfilling on the next challenge and getting home for some sleep. We both had work during this week, and as much fun as constant sex can be, lack of sleep can be a problem. In any case, it was my turn to give the gift first. I handed him his envelope and watched carefully as he opened it. His eyes rapidly went from serious to incredulous. He started to bluster and make noise as if he would refuse, so I calmly asked for my envelope. He passed it over as he reread his challenge -- to pass himself off as a woman at the trendy bar downtown. I thought I had outdone myself with that one.

Then, of course, I opened his challenge and had to consider who had outdone whom. It took me a moment before I could get it. "Wear a short skirt and no underwear. Go to a pool hall. Get free drinks by flashing the bartender; then play pool and show off. Anything that you want after that is up to you." What a wonderful gift -- he knows the exhibitionist in me! I reached over and kissed him deeply.

"It's a good thing we've shaved you, isn't it? Have fun!" I said as I went to prepare. You might think it would be a snap, but I had to do my makeup, my hair, and then pick out the right outfit. I decided I would do him one better -- I took off my bra and found that t-shirt that just showed the bottom of my tits. I wore that with an A-line skirt that came half way down my thighs. If I twirled around, I showed everything -- so I changed. I decided on one of my little black dresses; the fabric was sheer enough that in the right light my aureolae and my nipples were visible -- especially if I stretched. It hung from there and came midway down my thighs. I added thigh high stockings and heels, and peeked in on him as I was leaving.

He'd managed a pretty good look. His hair was already long enough to style; with makeup his face took on a very feminine look. He too was in stockings, but he was in panties and bra. I knew he had a set -- can't hide from momma! I left him to finish and I turned to leave, bending over and looking over my shoulder at him. "Will this do?" I asked, feigning innocence. He laughed loud, and I left.

The pool hall wasn't in the nicest neighborhood, but we'd been there a few times. Mid-week it tended to have a younger crowd -- just out of high school and some in college. In other words, some hot young studs trying to outdo one another. I could feel myself getting wet as I entered. I went to the bar and settled myself on a chair, my hips thrust forward and leaning back. I was sure my chest was in the light, and I hiked my skirt up to reveal my shaved pussy. When the bartended came over, it was my turn to be surprised -- it was a woman. But she looked at me like a man would -- that surprise turning to dirty thoughts kind of look.

"I'm Gail. What'll you have?" She asked. "Or should I say, what can I do for you?" She grinned.

"For now, just a beer. In a bottle."

She opened one, handed it to me in a way that suggested she could find another use for that bottle. Our hands touched as I took it, and I felt a bit of a spark.

"On me." She said.

"Maybe." I replied. I so loved that kind of suggestive flirting! I took my time getting the bottle to and into my mouth, all the time watching her watch my tongue. She swallowed hard at one point. I eventually took a long pull of it, and finished it with two more.

"Another?"

"I can't ever get enough....." I let that trail off into a suggestive smile. "I'll be back." I said as I got off the stool and headed over to the tables. I managed to add a little more sway to my hips as I did. I got a wolf whistle from someone behind me -- I think it was from her.

There were two tables, side by side, that had four young studs at each of them. Sexy young things -- no older than 22, and just bursting with that hot energy of horny men. I simply stood there between the tables until they noticed me. It didn't take long.

"Hey beautiful. Oh wait, are we allowed to say things like that?" Said one hottie, a well-muscled six-foot two.

"Are you saying I'm NOT beautiful?" I teased. "And here I went to all this trouble to look pretty tonight. Maybe these fellas are nicer to a lonely woman." I turned to the other table as I said it.

"We would love to have such a hot, beautiful woman watch us." Said one of the boys at the other table. He was kind of cute. He was the smallest guy there at five-four, but I liked the look of him. A little rough and edgy.

"Why, thank you. How do you play this game?" I asked -- as if I hadn't spent hours with a stick in my hand. The four at this table proceeded to tell me details about the fine art of stick handling. I made as if I didn't always understand, and kept finding ways to make the conversation very suggestive. Holding sticks. Putting things in holes. Like that.

Finally, one of the boys suggested I play. They racked the balls and gave me a cue. Well, here was the opportunity I'd been waiting for. I made sure there were at least two of them behind me as I bent over the table. I felt the hem of my dress rise up above the curve of my ass and knew I was showing them everything I had. I took my time in this position, and could see by the reactions of the guys in front of me that they all suddenly knew what was going on. My plan was working perfectly at this point. I finally broke and the balls scattered. The nine went into a pocket.

I turned around to the boys behind me, and noticed they now had significant bulges in their pants. "Don't you just love watching the holes they go into?" I asked. One of the boys seemed oblivious, but the other one registered some surprise. "Does that mean I get to stroke this again?" I asked, rubbing my hand suggestively on the cue.

They assured me that it did, so I moved to the other side, ostensibly to line up the white ball, but more importantly, to give me a bigger audience when I bent over the table again. I had flashed two of the guys at my table. Now I made sure that the other two would get their chance. Of course, it happened to also put most of the other table in a position to peek -- not that I minded, of course.

I bent, took my time as if measuring the shot, and finally stroked it. I made as if I stumbled and fell forward, onto the table, with my legs splayed for balance, I was giving half a dozen horny, virile young men a fill view of my moist pussy and puckered ass hole. In addition, I was getting wet and excited.

The boys stepped up on either side of me to help me off the table -- although they certainly took their time about it -- and as I came to my feet, I feel back against them, and my hands somehow landed on hot, stiffening cocks. Eventually I stood up straight, but not before exchanging looks around my table with the four young men there. Unless they were oblivious, it should have been obvious that I was up to more than a game of pool.

The good news was that they weren't oblivious. Within moments I was surrounded by the four guys from my table. I felt hands all over me. My boobs were squeezed and caressed. Hands were on my ass and running inside of my leg to my pussy. I stood there and let them have their fill for a few moments.

"Just a minute, fellas. Gail?"

She looked over.

"Can I ask a favor or two?" She nodded. "Why don't you turn off the open sign. It seems these gentlemen have a different game in mind. It's still one that uses sticks and holes and balls, but it's a little non-traditional. Then why don't you come join us? I need someone to film the action. That's at first. There may be a more interactive role for you. Eventually."

The grin on her face was all the answer I needed. As she was taking care of business, I turned back to my now hungry horde. "All right, boys, anyone interested in fucking an older woman? Because I'm sure interested in getting fucked!" I undid the halter tie at the back of my neck and my dress fell to the floor. It started an avalanche of clothing as they lost theirs as well.

I had a pretty wide selection of young men. From the short guy at five-four to a few who were well over six-two. Interestingly enough, Mr. Five-four had the most impressive cock of them all, at least nine inches and thick as a beer can. The rest were generally average.

One guy was tiny at about four inches, but he didn't seem self-conscious at all. I stood looking at a forest of cock, and was wondering what to do first when our bartender showed up and shocked us all.

It seems that Gale was both a large-breasted woman and a dude with a big cock! I hadn't ever encountered a she-male before, but could see that we'd be going at it at some point. As requested, Gail was filming, so it was time for action. I reached behind me and pulled myself up on a table, spreading my legs.

"It's always smart to get your lady friends in the mood, isn't it? Who'll do the honors?" That young guy with the small dick was there in a flash, and it was obvious that he'd discovered how to compensate for his lack of size. Oh. My. God! His tongue was soon buried deeper in my pussy than most cocks! When he shifted to my clit I immediately came. Hard. Again, and again! He was magical! I finally had to push him back off me to catch my breath.