Christmas Holiday Challenge

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"What's your name?" I asked, as absurd as it seemed.

"Angus." He replied. I grabbed his hands and pulled him up to me. Then I locked lips with him, tasting myself on his mouth and tongue. "You are amazing! I have friends who are going to call you. A lot!" With that I dropped off the table, to my knees and swallowed is tiny prick and spent two minutes licking and sucking it until he came in my mouth. I made sure to make a show of swallowing it and showing that I enjoyed it.

"Let that be a lesson, boys. Learn how to eat pussy like Angus and women will do anything to thank you!" There was applause, and Angus wound up high fiving everyone there. "For the rest of you, as far as I'm concerned, your names are Dick, Peter, and Cock. Now come fuck me silly!"

I so love younger men -- they come quickly, but then they are hard again and able to last longer. I started out on my back and three of them came in my pussy within two minutes. I was dripping hot male come into my ass crack, and one of them took advantage and used it as lubricant and soon my ass was getting a good dose of hard cock. Interestingly enough, it was Gale, who had a good sized (and thick) piece of man-meant. I was fascinated watching her boobs bounced as she fucked me, and probably would have been happy just watching that -- but at that point my view was blocked by a torso and a hard cock was shoved into my face. I'm not complaining, mind you -- that is what I was there for, after all -- but it took me by surprise.

I felt Gail cum in my back door, and after he withdrew, he was replaced by a very eager, very long piece of meat. The cock in my mouth only took a few thrusts before he unloaded and was replaced. This time, however, the one in my face was my big friend. At that point I stopped the action.

"The only way I can do justice to this dick is to shift positions. At this angle I can only get the head in my mouth, and you have so much more to give. I had the largest cock I had yet to fuck lie on his back; I sat on him and made sure they knew my ass was still available and then had Mr. Beer Can stand to face me.

"Okay, boys, you'll want to remember the night that the cougar came in and you spent hours keeping her air tight. I want you to keep my holes full of cock. Go!"

I spent the next two hours on that pool table. Every one of them fucked me in every hole and most came in all of them. Including Gail, the bartender. Before I left, I slipped my address and phone to Gail, Angus (the mouth) and Mr. Beer Can and told them to call me. Gail let me use a few bar rags to clean up before I pulled my dress back up and left. I did get a standing ovation, and was invited back any time I wanted.

Then it was home and into the shower. I was just getting out as James walked into the bedroom. We swapped phones and I watched his adventures as he showered and came back to view mine. I think I had a better time, but he really surprised me with how he got into it. And with what he let get into him! What the heck to do next?

December 16 -- the third day of Christmas

Well, I have to say that Claire went above and beyond the challenge yesterday. I suppose I should have expected it -- she's never been shy and she loves gang bangs. I guess I set her up. She had no complaints. As for my adventure, well, it's a good thing I'd learned some time ago that I needed to learn to appreciate cock if I was going to ask women to appreciate mine. The acting I'd done from time to time helped me to develop a character, and I did okay in the appearance department. So, it wasn't too tough to be an interested woman for eager men.

I convinced two guys to let me blow them instead of fucking them -- and then when I did, they were highly complementary.

"Best blowjob I've ever had." Said one of them. That was enough.

And now it was the third day of Christmas and the third challenge. I gave her the following -- "Get out of a traffic citation." She gave me "Fuck a coworker." That came with an exception. I had until tomorrow's dinner to accomplish it. But I decided not to wait. We left at the same time.

My boss, Cheryl, was a divorced black woman about my age. Her husband had custody of her kids. She has frequently hinted that she's lonely and horny. I was trying to be circumspect about things and hadn't made any moves. After all, I do wear a wedding ring and she had met Claire at office parties. So, I called her cell from my car.

"Hi, Cheryl, it's James. This is not a work thing -- I just realized how close it is to Christmas and thought I ought to take you out for dinner instead of trying to buy some inane gift. I know it's spur of the moment, but how about it?"

"Well, I was just sitting down to my gourmet macaroni and cheese ala TJ -- I think I can pass that up. I can be ready in fifteen minutes -- how should I dress?"

"A little nicer than daily office wear, okay?" She agreed and I drove over. She had a small house on the other side of town. I parked and walked to the door. She opened it just as I arrived. She had indeed done "nicer than the office, including a delightful perfume and some added lipstick. I stood back and whistled.

"Well, it's going to be pleasure to have you on my arm this evening. You look hot!"

"Flattery will get you anywhere, James!" She dimpled.

"Then I'll be sure to keep it up longer than usual this evening." I replied with a straight face. She locked the door and we walked to the car. I opened the door for her and got a flash of thigh as she sat in the bucket seat.

It was a short drive to the restaurant I had in mind. An intimate club with a jazz combo, they specialized in French cuisine. And had a well-stocked wine cellar. We stared with wine, and we kept drinking through a delightful dinner. We'd put away a bottle and had started on a second by the time we finished the main course. At that point the small combo was playing, and when they got to something slow, I asked her to dance. We were one of the three couples on the floor to begin with and were eventually joined by a few more.

I started out holding her at arm's length, but gradually drew her closer. Soon her head was on my chest and we were basically swaying in place. Cheryl was very well endowed, and soon her big tits were pressed tight against my chest. I began to grow hard and made no move to hide it from her. I knew things were moving in the right direction when I felt her press into it. She looked up at me and I bent and kissed her hard. She returned the kiss. When the band segued into another slow number we stayed on the floor, pressed tightly against each other.

When that song ended, we slowly separated. She said she needed to visit the lady's room and I watched her walk towards it. Her hips were swaying in a way they never did around the office. A few minutes later she was back at the table. She held out her hand, and when I took it, she pressed something damp into it. Her panties.

"What a lovely gift. Before I accept it, we should talk for a moment. I want you to know that Claire and I have had an open marriage for the past five years. We love each other deeply but we also are free to love anyone else we choose. We've actually discussed what you might be like and whether you'd want to join us. Tonight, however, I want you all to myself. Do you think we can enjoy this evening and not have it be a problem at the office? Because if the answer is no, then we'll go no further. I am hoping that's not the answer."

I felt her hand at my crotch, unzipping my fly. At the same time, she took my hand and placed it up her skirt where I found a wet pussy.

"Honey, I don't really care about things at the office. Right now, I'm hotter than a pistol and wet as I can be. I want that hard cock of yours in the worst way. Let's got make Claire sorry she couldn't join us tonight. Although I'm interested in making it a threesome at some point."

I threw enough cash on the table to cover everything and leave a healthy tip. Then we got up and walked out with her hand in my pants! Once at the car, she dug out my cock and took it all into her mouth. I came within a minute and she swallowed it all! I managed to get the car started at that point and headed back to her place. Along the way she spread her legs and I used my free hand to play with her pussy. She came at least twice just from being fingered!

When we got to her home, we rearranged our clothing, parked and went inside. She grabbed my shirt and pulled me into her bedroom and we began to lose our clothing. When I told her, I wanted to record it, she seemed reluctant at first, but then agreed.

Once the camera was on, she faced it and grabbed her breasts.

"See these big tits? I'm gonna smother you with them. And then I'm gonna sit on your face since I haven't had someone eat my pussy in months. And see this big booty? You are gonna fuck it till you're raw and sore. I ain't had anything hot and warm in any of my holes in way too long. You are going to be my Christmas treat tonight!"

Three hours later we'd done all that and more. The good night kiss I gave her tasted of pussy juice, sperm and ass. I suspect she'll be joining us at hone for New Years.

December 17 -- the fourth day of Christmas

I loved the video James showed me from last night. Cheryl was one hot momma. Her tits are ginormous -- I can't wait to get hold of them. I told him to invite her for New Year's and to plan on spending the night. Meanwhile, we still had this damn challenge to handle.

Yesterday I was told to get out of a traffic citation. The implication was that I was to use sex in some way. At least, I assumed that was the case. Judging by James' response to the video, it seems likely. But it wasn't easy!

First off, I had to do something that would have a cop pull me over. Safe driving is so ingrained in me that it was a real challenge. Finally, I remembered that the locals sometimes had a radar trap out on the highway and went for it. Driving out of town I spotted a waiting patrol car looking for incoming speeders, so I drove past, turned around and headed back about twenty miles per hour above the limit. When the red and blue lights showed up in the rearview mirror, I made sure to pull over in a location that was out of view of the highway. When the car pulled in behind me, I lost my clothes and sat behind the wheel with legs spread wide and a hand on my clit.

I saw the light in the cruiser behind me, and could tell there were two cops in it. This was going to be really interesting. I was naked when the first trooper came up along side me and tapped on the window. I rolled it down and turned to face him, making it really obvious that he had a naked woman to deal with.

"Good evening, ma'am. Is everything all right?"

"Yes it.is. Is something the matter?"

"Well, I don't usually encounter naked women behind the wheel of a car I pull over for speeding. You do know you were speeding, don't you?"

"I didn't mean to. I was playing with my pussy and I guess when I came, I pressed the gas. I'm so horny, officer. I tried some herbal remedy a friend gave me, and I've never felt this way in my life. All I want to do is find someone with a hard cock and jump on it! I can't believe I'm even saying this, but I'm desperate!" I was getting into it -- I almost believed it myself!

"Hmm. License and registration, please, I'll check with my partner and be right back." At this point, I really was horny, so I occupied the time by inserting a few fingers into my hole and flicking my clit. I was just cumming when I sensed the officer was back.

"Ma'am, my partner and I would like to see that you get help. Why don't you step out of the car so we can take advantage -- I mean care -- of you?"

"Oh, thank you, thank you, officer!" I opened the door and got out, naked. The brought to the front of my car. At that point I had two young studs towering over me. Both of them were sporting erections jutting out of their uniforms.

"If you'll stand between us, ma'am, and lean forward, we can examine you to see if there are any signs of trauma."

"Screw that." I said. "How about one of your fucks me, while I suck the other? Let's not pretend anything. I just want to get fucked and you are the guys to do it!"

What followed (caught on my dash cam) was an hour of bouncing between their hard cocks. By the time they'd each come twice, I announced that they'd cured me. They went back to their cruiser and drove off. I put some clothes back on and left for home without a ticket. Challenge completed.

So, we had the Day 4 challenges to do. Tell you the truth, I was beginning to not care what day it was -- a new sex challenged a day was simply a delight. He gave me an easy one for Day 4 -- "go to a bar and see if you can pick up a man who'll fuck you while I watch." Easy enough -- I went, made sure to flash some nipple, and soon had my pick of the eligible males. I made little pretense with them -- if they were hung, I'd invite them. Of course, I had to verify the hung part, but that's what men's rooms are for, right? The first three I checked out loved the examination but chickened out when it came time to come home. Jonas, number four, however, was not only the biggest of them but he was the most adventurous and came home for the evening. We started without James, who seemed to be having trouble fulfilling his challenge, but by the time we got home I'd let him know what to expect, and not only was he excited to watch, he eventually participated as well.

The challenge I'd given him was almost unfair. "Meet a strange woman and convince her that all you want to do is eat her pussy for two hours. There's nothing for her to do but enjoy." I know my husband can keep his nose in a cunt for longer than that, but it was the part about getting one to accept that I suspected would be a problem. As it turns out, he scored right away -- she just wouldn't let him stop at two hours. And, being the nice man that he is, James couldn't leave her stranded.

December 18th, the fifth day of Christmas

So, that was day four. Here's it was, the infamous Fifth Day of Christmas. And wouldn't you know it? We both inadvertently picked something we could do together! I handed James an envelope with the task "Find five different piercings under a woman's clothes." And then damned if he didn't hand me an envelope with five golden ring piercings and the task "Replace the piercings you currently have with these five golden rings, and then show them off!"

Well, that was an easy challenge -- he replaced the ones in my nipples, navel, clit and pussy lips and we took pictures. Then we fucked like minks for the rest of the night, laughing all the way!

We have more challenges yet to come. Or we'll come from the challenges yet to come.

We originally intended to stick close to the song, but neither of us is into bestiality or gymnastic sex. We're still working out the remaining 7 days -- let us know if you have any suggestions!

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  • COMMENTS
4 Comments
Dark_StormDark_Stormover 5 years ago
Suggestions for the next days

Geese a-laying could be laying a group of women (geese=females). Swans a-swimming could bring back the Chilton brothers and their swim team mates. Maids a-milking is obviously a lactation story. Ladies dancing could be strippers (or perhaps something less cliche, like ballerinas). Lords a-leaping could be fucking (or getting fucked by) gay men. Pipers piping doing the plumber(s). Drummers drumming fucking the boys (and/or girls) in a band.

One has to assume that the wife is leading the husband into bi encounters, so perhaps the story could end with a bi orgy with both spouses and the members of the band. The wife also needs to have a few bi/lesbian encounters along the way.

The main problem with the story, so far, is that only one partner's encounter gets fully covered and the other's is pretty much blown off. It would be better if further chapters dealt with only one day at a time and detailed both spouse's encounters.

OGHMNWOGHMNWover 5 years ago
On the Tenth day my true love....

10 Lords a leaping at the chance to screw and make my lady air tight.

Wildspur55Wildspur55over 5 years ago
Build up, don't let down

It would have been better to start with smaller challenges and progressively build on them. After the gang bang on day 2 there wasn't much left to anticipate.

AnonymousAnonymousover 5 years ago
Too superficial

Each day could be better developed.

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