A Surprise Family Christmas Orgy

Summary: Faithful man is tempted by sister-in-law at Christmas party.

Note: This is a 2015 Christmas contest story.

Note 2: Thanks to goamz86, Robert, and Wayne for editing this story.

A Surprise Family Christmas Orgy

"You want me to be your sister's plus one?" I asked for a second time, unsure I had really heard her correctly the first two times.

"Yes," Jasmine, my wife, replied, annoyed at having to repeat herself.

"Isn't that weird?" I asked, thinking it was incredibly weird.

"Maybe a little," she shrugged, as she pecked away on her computer like she often did. "but Jennifer isn't ready to get back in the dating pool and doesn't want to be getting the pitying, 'oh you're getting divorced', looks. So she wants a handsome man to show off."

"We'll, the handsome part I have to agree with," I smiled, always loving to pump myself up.

"And you have to act like you're her smitten boyfriend," she continued, looking up.

"This just keeps getting more and more like I'm on Candid Camera," I quipped, looking at the roof.

She said, all serious, "She's stressed out and I offered your services."

"I'm just a gigolo, and everywhere I go," I sang off key.

"I said you're handsome, I didn't say you were David Lee Roth," Jasmine quipped back, always willing to go tit-for-tat in our playful banter.

"And it's this weekend?" I asked, as I was supposed to go with her to her boring teacher's Christmas party.

"Yes," she nodded. "And yes, that means you get to miss the boring teacher party you hate every year."

"This continues to be in the too good to be true department," I pointed out, smirking that she always knows what I'm thinking.

"Have I mentioned it's at The Cassandra, the booze is all free and you get to share a hotel with my sister?" she added.

I looked around for cameras. Jasmine had been acting strange the past few months, since Valentine's Day truthfully. Spending more time with her siblings than ever, never complaining about them and being way wilder in and out of the bedroom (oral sex while I drove, talking dirty in the bedroom and even experimenting with anal sex. She even began to tolerate her annoying, overbearing and critical mother. But this, this was very strange. "You're serious?"

"Yes, I love my sister and don't want her to be alone and pitied or questioned all night," she explained.

"If that's what you want," I agreed, her sister actually really fun to be around usually...clearly the party girl and leader of the three sisters.

....

On the day of the party, my wife helped dress me, putting me in my best suit. I'm a decent looking guy and in the suit I looked smoking hot. I joked, "I'm going to be irresistible to Jennifer."

"Yes, I'm sure she is going to strip you naked and fuck your brains out," my often sarcastic wife quipped.

We both trusted each other unconditionally, so such blunt talk wasn't uncommon. I quipped, posing sexily, "Jennifer's a go-getter. I'm not sure I'll be able to hold her off if she decides she wants a piece of this."

Jasmine laughed, "If she decides to use you as her personal plaything, you have my permission."

"You know I'm utterly irresistible in this outfit," I pointed out. "You're giving me carte blanc to do your sister." The conversation was getting strange, but I was enjoying teasing my wife.

"Do away," she waved, before adding, "you need to go and pick her up. She hates being late."

"That's a family trait," I joked, my bride getting instantly bitchy if we were late for anything.

I gave her a kiss and drove across town to Jennifer's rented condo as the divorce was still in the ugly early stages... a divorce that was about millions, give or take.

As soon as I pulled up, five minutes late, Jennifer walked out and I instantly got a hard on. She was in a short red cocktail dress and mocha nylons, my favourite colour of nylon (my fetish being nylon-clad legs and feet).

I got out of the car, quickly adjusted myself and went to open the door for her like any gentleman would do.

As she walked towards me, in four inch opened toe heels, she said, in her usually pretentious tone, "You're late."

"A train blocked the road for almost ten minutes or I would have been early," I explained, which was the truth, as I opened the car door for her.

"I guess I'll forgive you," she smiled, reaching me and kissing me on the cheek.

"You're apparently going for the lavish look today," I complimented, "you look absolutely beautiful."

"Thanks," she smiled warmly, a side I didn't see often with her of late. "You look very handsome yourself."

"I clean up well?" I joked.

"Yes, yes you do," she agreed, her tone oddly ominous, as she got into the car.

I closed the door once she was in, taking a longer than socially responsible look at her sexy legs (she was in amazing shape).

I slightly adjusted myself again as I walked back around to my side thinking this was quite the temptation my wife was accidentally putting me through.

As we drove to the hotel, the nicest by far in the city, I couldn't help but continually glance at her nylon-clad legs.

She said, taking control like she usually did, the reason I believe her marriage ended - men don't like dominant women, "So what is our story for this evening?"

"We have a story?" I asked, trying not to glance at her nylon-clad legs.

"Of course," she said, "it needs to look like we are in love."

"Oh," I said, this already getting way more complicated than I first imagined.

"So to keep it simple, and kind of true, we met through my sister and have known each other for years," she explained, having obviously put thought into this.

"So far, so good," I nodded.

"We have been quietly dating for a couple of months now," she continued.

"Okay," I nodded, wanting to keep it simple as my memory was not one of my strong suits.

"Lastly, we need to look like we are very much in lust," she finished.

"Lust?" I questioned, surprised by her word choice.

"Yes," she nodded. "I can't be in love with you already, but I can definitely be infatuated. As can you."

"So I'm treating this like the early stages of dating," I clarified, remembering the daily lengthy fuck marathons between Jasmine and me the first few months.

"Exactly," she nodded. "I need you to hold my hand, to kiss me on occasion and to play the part of horny guy."

"Those are words I never thought I would be told by you," I laughed, glancing again at her legs, of which there was a lot showing.

"I'm dressed for you," she added, catching me checking out her legs.

"P-p-pardon?" I stammered, quickly returning my gaze to the road.

"Jasmine told me long ago your quirky nylon fetish," she answered, slipping out of her shoe and putting her nylon-clad foot on the dash. "Cameron liked nylons too, but not as much as you."

I was speechless as the conversation continued getting stranger.

As she wiggled her foot, my gaze unable to not stare at her perfectly manicured toes, she continued, "She also told me that you particularly love the toenails to be red and your favourite colour of nylon is dark beige."

"She told you all that?" I asked, stopped at a red light and unable to not stare at her calf, foot and toes showcased so perfectly in nylon.

"We share everything," she answered, stressing the last word excessively.

"That is incredibly alarming," I said, as a horn blared behind me.

"Green light," she said, her tone clearly amused.

My cock was rock hard, but positioned so awkwardly it was uncomfortable. As I started driving, I tried to slyly shift my cock into a better position.

As I repositioned my cock, she said, even as she continued wiggling her toes, smirking, "Good to know I can make you hard with just a tease of the foot."

"I'm a guy," I shrugged.

"And apparently you are a great pussy muncher," she added, making me gasp. She added, "I told you... everything... we have no secrets."

"That is utterly the most disturbing thing I have ever heard," I said, although really the idea turned me on.

"She says you have a magical tongue," she continued.

"I'm the Gene Simmons of pussy pleasing," I countered, deciding to play along with this bizarre conversation.

"Mmmmmm?" She said, the fake moan overdramatic and hot.

"So you dressed up for me?" I asked, trying to wrap my head around her bizarre behaviour. I mean she always was the fashionable, name brand only, high heels type of woman, but this was the kind of conversation that happens in my jerkoff fantasies when I'm stuck in a hotel (men almost never jerk off to their wives).

"Yes," she answered, not explaining her reasoning.

"Why?" I asked.

"I want you horny as hell all night," she answered, rather matter-of-factly.

"Why?" I repeated, getting more questions with each answer.

"You need to look like you can't wait to leave this party, take me back to the hotel room and fuck the shit out of me," she bluntly answered.

"Fuck," I replied, realizing I was way over my head.

"Maybe later," she quipped, her tone a mixture of playful 'I'm just fucking with you banter' and serious 'I'm going to fuck the shit out of you'.

I didn't answer, my head spinning, my pants bulging, as I pulled up to the front of the hotel.

The valet took the car, and a bell hop took our bags, as Jennifer took my hand in hers, the first woman other than my wife to hold my hand in fifteen years. Guilt instantly rushed through me and I knew I was going to call my wife as soon as I could get alone.

We walked into the lavish hotel, checked in and went to our room, which I learned was on the 28th floor, the top floor. She held my hand throughout the elevator ride, even though no one was around to show our fake love to.

The evening of surprises continued when we walked into the room, which was actually a suite, apparently the honeymoon suite. It had a Jacuzzi, wine chilling and one, yes one, king-sized bed.

I pointed this out, "There is only one bed."

"Is that a problem?" she asked, as she went to the window and looked out.

"Jasmine may think so," I pointed out, thinking this just kept getting stranger and stranger.

"Don't think you can keep your hands to yourself?" she asked, still looking out the window.

"It's not me I'm worried about," I countered, unable to not flirt back.

She ignored my response and said, "This really is a glorious view."

As I stared at her perfect body, dressed to tease, I wanted to say, "Indeed it is', but instead I said, "I should give Jasmine a call."

"And we should probably head down," she said, turning to me.

"I just need to check in first," I said.

"Sure," she nodded, "I better go make sure I look good enough to fuck."

Her bluntness wasn't unusual, but in regards to sex it was. Once she left, I quickly called my wife. As soon as she answered, I asked, "Do you have any clue what you've got me into?"

"She really doesn't want to be pitied tonight," Jasmine responded.

"Apparently," I replied. "And you told her about my nylon fetish?"

"Both my sisters, actually," she replied, "we talk about everything."

"So I learned," I said, before joking, "Apparently, I'm also good at oral sex."

"I tell you that all the time," she said, "I screamed it last night actually."

"Maybe you should Facebook it," I joked.

"You should be happy that I rave about your wicked tongue," she playfully countered.

"I'm not complaining," I said, "but your sister has been very flirty and borderline aggressive."

"Again, just go along with it," she said. "You need to look like an authentic infatuated couple."

Just then Jennifer returned from the washroom, walked to me and took the phone from me. "Hey, baby sis. Thanks for sharing your husband with me."

Hearing the word 'sharing', I thought it was an odd choice.

After a pause, Jennifer promised. "Don't worry, I'll take very good care of him tonight."

Her tone wasn't remotely subtle in her intent.

"I'm going to put him on speakerphone," Jennifer said, her right foot moving in and out of her shoe, purposely teasing me, a constant distraction as I couldn't not look...my fetish and dick controlling me.

After pressing the button, Jennifer continued, "Your husband seems a bit tentative about being my date tonight."

Jasmine sighed, "Honey, tonight treat Jennifer the way you would treat me if you were at my Christmas party tonight."

"All you do is tease me all night," I pointed out, Jasmine always touching my cock slyly, rubbing her nylon foot on my leg, and whispering naughty things throughout dinner and the incredibly boring speeches.

"As I imagine Jennifer will do, too," Jasmine countered.

"Game on," Jennifer agreed.

I quipped, trying to shock the older sister, "Those nights always end in blow jobs or marathon fucking sessions."

"Good to know," Jennifer smiled, not shocked but instead only adding to the sexual tension.

"Help Jasmine, your sister is raping me with her eyes," I only kind of joked.

"Well you are rape worthy," she quipped.

"You're not helping," I pointed out.

"I got to go," Jasmine said, "Connie is here."

"Why is Connie there?" I asked, Connie being her other older sister.

"I needed a date, since mine was on another date," Jasmine answered.

"I'm on a date?" I questioned.

"Just treat her like you would treat me at such an event," Jasmine repeated.

"Okay," I agreed, even though those events did usually lead to oral sex on the drive home and a good fucking once we got home, as I had quipped earlier... Jasmine being very submissive once in the bedroom, and very obedient.

"Have fun, and Jennifer, don't do anything I wouldn't do," Jasmine quipped.

"What won't you do?" Jennifer asked playfully.

"I don't know, Mike what won't I do?" She asked all seductively.

"I'm beginning to feel like a piece of meat," I joked, not sure I should answer that question properly... my wife a very willing participant in the bedroom and willing to do almost anything to please me.

"Hopefully you're a full course meal," Jennifer quipped, seriously eating me whole with her look.

"Gotta go," Jasmine said. "Have fun, and Mike, you have my permission to be overly touchy feely with my sister. You are her gigolo for the night."

I was about to say that gigolo's have sex with their dates, but she hung up.

Jennifer smiled, took my arm and said, "Let's go, my gigolo."

I followed her out completely befuddled with what lay ahead and hard as a rock.

As we entered the hall, mistletoe was right above us. She turned to me, leaned forward and kissed me on the lips. It wasn't a long kiss, but it wasn't a short kiss either, as her tongue parted my mouth. I loved kissing, but Jasmine wasn't a big fan, she'd rather get ass fucked than kiss... yes, I was that lucky.

She quipped, "I love mistletoe."

I remembered the time when I put mistletoe above my cock at a Christmas party with Jasmine and renamed it mistle-blow.

She then added, "I also love mistle-blow." She winked and pulled me speechlessly into the main room.

The next hour I met lots of people, all the while holding Jennifer's hand. When I went to get drinks, I planned on having a few, she kissed me on the lips. When she went to the ladies room, leaving me with three complete strangers, she kissed me on the lips.

A part of me felt undeniable guilt and yet a growing part of me was getting incredibly horny. I loved my wife, and found her to be beautiful, but there was definitely something very alluring about Jennifer, who'd never had any kids thus no baby weight and who worked out every day to keep her body perfectly toned. Sure her tits were tiny, but I wasn't a tit man so that really didn't matter.

No doubt if I was single and had met Jennifer first I would have gone after her with my full court press. She was beautiful, had an amazing body and had spunk. Yet, she was my wife's sister and I would never cheat on my wife.

At supper, Jennifer's version of being an authentic couple included her hand on my leg, slowly slithering up until her fingers grazed my undeniably stiff cock. It included her nylon-clad foot moving under my pant leg just like Jasmine would do. Yet, all I could do was try not to jizz in my pants.

As we waited for dessert, she gave my cock a firm squeeze and whispered, "Jasmine wasn't lying."

I groaned and went to move her hand away before I erupted.

She took my hand instead though and put it on her nylon covered leg. My eyes went wide as it was easily the softest, silkiest nylon I had ever felt.

She whispered, "These nylons cost me 65 bucks when I was in France last month. Do you like?"

"They're really soft," I admitted, wanting to slide my hand up and down her leg. But instead I tried moving my hand away, this temptation becoming harder and harder to resist (pun intended).

"I bought them for you," she said with a seductive smile as she moved my hand slowly up her knee to her thigh.

"For me?" I asked, mesmerized by her words and her leg... getting drawn into a sinister sexual web I was going to be unable to get out of.

"Of course," she said, as the dessert arrived. "Mmmmmm, pie. I love pie, do to love pie?"

"It's an acquired taste," I quipped back, the flirtatious me beginning to take control as my lower head began to lead.

"Some pie is heavenly," she offered, as she took a bite and moved her hand off mine.

I allowed my hand to remain. Not moving, just enjoying the silk and letting her know her aggressive attitude didn't faze me. "Pie does need to be savoured."

"I couldn't agree more," she nodded. "Plus no two pies are alike."

There was silence, the naughty innuendo lingering between us.

We chatted with the others at our table and drank more wine. Three bottles done between the two of us, my hand never moving off her leg.

I didn't enjoy the pie, raisin not really a great choice. The server asked as she was cleaning up the plates, "You didn't enjoy the pie?"

"No, I like my pie to be much moister," I answered.

Not rattled by my response, Jennifer said for all to hear, "Oh, then you will love my homemade pie, it's a recipe like no other."

I don't know why I said it, knowing it would only encourage her (I blamed the wine and her nylons), as she wasn't rattled by my overtures at all, I countered, "I can't wait to taste it."

I'll make sure to have it made nice and warm for you when you come for some," she said, making my mouth literally water, as she reached and squeezed my cock again.

She asked, "Is this because of me?"

"Actually it's for the pie," I countered, not playing Mr. Nice Guy any more, giving Jennifer a very firm squeeze on her leg...deciding a full frontal attack may be the only way to calm her aggressive behaviour.

She leaned in and whispered, as she shocked me once more, fishing my cock out of my pants in lightning fashion and beginning to jerk me off, "I think you have the filling for my pie."

"Fuuuuck," I quietly grunted, paralyzed by her touch as my cock, long teased tonight, was instantly ready for eruption.

"Shit, you two should go and get a room," Wanda, a pretty co-worker of Jennifer's quipped.

"We have one for later," Jennifer replied, her intent in the words and her hand stroking my cock obvious, "but I can't resist this sexy stud."

"I am utterly irresistible," I added, trying not to come, as I also tried to act casual.

"Hot as a volcano about to erupt," Jennifer added, as she continued stroking my cock.

"You two lovebirds make me sick," a guy whose name I couldn't remember said.

"I can't help it," I shrugged, trying to play the doting boyfriend, "She's just so fucking hot."

"You know just the right words to say, baby," she purred. I tried to keep a straight face as I focused on not coming under the table.