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.
