A Few Days Away: Day One

It started one night over a few too many drinks at a small quiet bar in Charleston, SC. My wife Annie and I had spent the day exploring and ended up in this out of the way bar talking – about anything and everything. Per usual the topic turned to sex – having been together for seven years there are few things we couldn't discuss and even fewer things that we hadn't tried. Sex with Annie had always been spectacular – she was a willing and able participant in anything I could dream up. While adventuresome and uninhibited in many ways our exploits were always solo endeavors – in other words it was she and I alone – we had spoken through the years about all manners of things, threesomes, swapping etc. – but to this point had never felt the urge to explore beyond each other. This would all change as we started discussing two of our dearest friends– Jake & Lora.

We had been friends with Jake & Lora for years – going on long weekends and sharing many good times. I had met Lora years earlier in college and there was always this spark between us however nothing had ever come of it as we both grew into happy relationships with our respective spouses. There had been comments made and innuendo tossed about from all of us but nothing beyond the usual flirting and playing. This would soon change as Annie and I delved into the topic with vigor – finally admitting our attractions. We decided that we would invite them down to our place for a weekend and make the proposal.

Once we were all together a few weeks later over wine and a lovely dinner we finally broached the subject – our concerns that they might be offended were quickly diminished when they both laughed and said they had been thinking the same thing but never had the nerve to bring it up – even to each other. From there things moved quickly – they went back to Chicago and I went to work making the arrangements. I have knack for planning trips and took on this task with a smile on my face and a stirring in my shorts. For me it was the fulfillment of two long held fantasies. My beautiful wife was going to fuck another man and come back and tell me everything and I got to spend a weekend with Lora one of my all time dream girls – it all seemed perfect.

I planned it so our 'dates' would arrive and depart at approximately the same time – so each new couple was restricted to 72 hours of free time. My Annie was to land in Chicago on Friday afternoon where Jake would pick her up for their adventure in the windy city, while I was to meet Lora at Miami International for our weekend on Miami's South Beach.

The beauty of our little arrangement was that we were foremost all still friends. It provided each of us the opportunity for a little variety without having to lie & cheat. We were all tested and perfectly safe and we all loved and respected each other. Physically the ladies were on opposite ends of the spectrum both beautiful in their own right - but different. Annie was dark and mysterious with perfect little breasts and perpetually hard nipples. Her eyes and hair were dark and she had an ass to die for. Lora on the other hand was light skinned and blonde with large full breasts and long legs – they were both perfect in completely different ways. Jake & I could not go wrong – their differences only made the adventure more exciting.

Day One

Annie and I made love at first light – slowly and deliberately, without speaking we were able to convey our excitement and apprehension on the journey we were about to take. Afterwards, over coffee we assured ourselves that everything would be alright. As I helped her pack we tried to choose things that would keep Jake on his toes. The weather in Chicago was cool in September and their itinerary called for lots of walking – so comfort and style needed to go hand in hand. In the end there was a variety of skirts and sweaters with the perfect accents of thigh high stockings and camisole tops underneath and her sexy black boots really topped off the various ensembles. For the trip she choose a simple short black skirt with a light gray cardigan sweater held together with just one button – just barely covering her lacy white camisole top and proudly displaying her constantly erect nipples.

As she pulled on her black stockings I couldn't help but notice that she wore no panties – her perfectly trimmed little kitty peeked out at me – despite our earlier lovemaking I was growing aroused and had to busy myself with my own packing so as not to be late. We were both a bit quiet and introspective on the drive to the airport and I held her hand and told her I loved her more than once. Before she left the car I held her tightly and asked if she wanted to back out – winking she looked me in the eyes, guided my hand under her skirt and whispered "I've wanted to jump Jake's bones since the day we met – I hope you warned him that he is for the ride if his life." With that she walked off with a little extra shake in her step – her black boots clapping loudly on the asphalt. Her dark hair and sassy attitude has always caused heads to turn and today was no different. I laughed out loud hoping my pal Jake has ready for some fun. Feeling more at ease I drove off to park the car and wait for my 'date' to arrive.

Miami

Standing outside the security gate scanning the faces of those departing Flight 1233 from Chicago – my head spinning with the reality of what was happening. At this very moment my wife was walking into the arms of another man while I stood in anticipation of seeing his wife's smiling face. While it was all a bit overwhelming, it was even more exciting. I caught a glimpse of blonde hair in the crowd and suddenly there she was - as radiant as I remembered. Her face broke into a wide smile when our eyes met and she ran into my arms – with a great big bear hug and a glancing kiss our weekend had begun.

Walking to my car she masked her nervousness with mindless chatter about the flight, the weather and such. Walking next to her I marveled at her natural beauty – dressed casually in a yellow sundress and sandals she was a vision of Midwestern beauty. Blonde hair recently cut into a stylish bob with big green eyes and milky white skin that glowed. Her body was as fine as ever her large breasts swaying freely beneath the flimsy material of her little dress. I could tell she wasn't wearing a bra and was simply dying to see if she had bothered with panties. Upon reaching the car I threw her bag into the trunk and walked around to hold her door open – before she sat down I took her face in my hands and kissed her fully on the lips. Pulling her close, I whispered in her ear "you look beautiful and I feel like the luckiest man in the world to have you to myself for the entire weekend…" She said nothing but sighed heavily as she felt my hardness growing between us. With that I helped her get situated and was treated with a perfect view of her breasts and an ample amount of her long legs. With the top down on my new Saab convertible we wheeled into the bright Florida sun on our short drive to South Beach…

Chicago

Meanwhile at the newly remodeled Midway airport in suburban Chicago Jake had his hands full. To get up her nerve Annie had had a few glasses of wine on the plane. On seeing Jake she jumped into his arms wrapped her legs around his back and whispered in his ear "I have been dreaming of your big, hard cock for 2000 miles!" With that she slipped his hand up under her skirt and he could feel her soaking wet and freshly trimmed pussy - his dick jumped to attention. As they waited for her luggage, she continued to tease him whispering in his ear and groping at his crotch. Upon reaching his Range Rover they paused for a moment and kissed - her mouth tasting of wine was nearly as hot and wet as her little kitty. Grinding against his leg and throbbing cock she reached over and opened the passenger side door. Making a bit of a show of it she climbed up into the truck briefly exposing her perfect ass and the tops of her stockings. Shutting the door Jake adjusted himself in his pants and silently thanked the heavens for his luck. When he got around to his side of the truck he took a moment to contemplate what was happening – this incredibly sexy woman was inside just dying to get fucked and his wife had no problem with it at all. Jake was a good looking man and had his share of pussy in his life but he had remained faithful to Lora for all these years and he was more than ready for a bit of 'strange.'

Opening the door he was treated to a view of Annie's flawless ass poking out from her little skirt as she dug around in the back seat for her bag. Sitting and pulling the door closed – he just sat and admired the view. After a moment he couldn't take any more he slapped her lightly on the ass, pushed her into the back seat and climbed in after her. Struggling with his belt he pulled out his rock hard cock and plowed into her from behind – her soaking wet pussy offering little resistance. With her skirt bunched up around her waist and her head buried in the soft leather interior, Annie felt another man's cock slam into her for the first time in years and she was in heaven. Jake fucked her like a kid on prom night and came in torrents as her muffled cries of ecstasy echoed around the truck. Pulling out of her dripping wet pussy with an audible pop Jake lay back in the seat and caught his breath. Smiling widely she adjusted her little skirt and stockings and announced – "well I think this is going to work out just fine – it's nice to see you again Jake…" with that the both burst out laughing and the weekend was officially under way.

Miami

Meanwhile back in Florida, the drive in from MIA was filled with the usual catching up conversation with no mention of what was about to transpire. Upon reaching South Beach, Lora and I were stuck in traffic on Ocean Avenue as we inched towards our Hotel. She had her sunglasses on and her head back soaking up the late afternoon sunshine with a big smile on her pretty face. I was gently caressing her warm thigh and slowly working my way upward. With the music playing softly ad the warm sunshine we were in our own little world - oblivious to the noise and the traffic – her legs parted slightly as my hands drifted up her thigh inching closer to that pussy I had dreamed of for so many years. I just lightly brushed her kitty as I slid my hand down her other leg – feeling her heat and wetness and causing a serious stirring in my shorts. She let out a soft moan, barely audible over the sounds of the street but her legs opened further and I knew she was ready.

Upon reaching the hotel we were temporarily forced out of our dream state and back to a small piece of reality. Tossing the bellman a twenty I popped the trunk and hurried to the front desk to check us in – Lora was standing in the lobby admiring the waterfalls and tropical fauna when I grabbed her hand and pulled her to the elevator. Once inside the elevator car I pulled her close and kissed her hungrily on the lips – wallowing in the sweetness of her lips and the wetness of her mouth. Sliding my hand down her waist I found her ass and gave it a squeeze whispering in her ear how badly I wanted her. Upon reaching our floor we practically ran down the hall to room 2015 and burst in. The sunshine off the Atlantic was blinding and we both put our sunglasses back on and moved onto the balcony. Standing looking out at the blue Atlantic and the bustle of Ocean Ave. twenty floors below I pulled her tightly to me and we kissed again. Turning her around so she was facing the sea I wrapped my arms around her and cupped those magnificent breasts as I had longed to do.

As she pushed her ass into my growing hardness I fondled her tits and tweaked her nipples as I softly kissed her neck and told her how beautiful and sexy she was. Slowly I worked my throbbing cock out of my pants and slipped it between the cheeks of her ass – raising her little sundress in the process. Feeling my bare flesh against her she leaned forward and offered herself to me and I slid inside – feeling her warmth and wetness envelop me – I let out a gasp. As slowly as possible I moved in and out of that amazingly hot pussy relishing every single stroke.

Her breathing intensified as she pushed back into me with more energy – reaching around I put my right hand between her legs found her swollen clit - with one gentle rub she came - in a wild rush of moans and juices her pussy pulsated and squeezed me tightly prompting my orgasm to coincide with hers. Complete sated for the moment I pulled out of her and led her to the nearby patio chaise on shaky legs. With a weary smile she dropped down into the shade and closed her eyes. I stood and looked down at this beautiful woman – smiled broadly and thought of what might be transpiring up North with my sexy Annie.

To be continued...