Madison is the Entertainment

Another one of "those" stories

Madison Becomes the Entertainment

My name is Ryan and my beautiful wife is Madison, we have been together for about 9 years now and often have the conversation about extramarital activities. It mainly happens on long road trips or when we are feeling extra kinky in the bedroom but nothing has ever come of it. Now to be clear our sex life has never lacked but after this long, sometimes it's nice to add something to spice things up a little.

Having moved from another state to the deep south of Louisiana it's obvious that Madison had a lot of friends and it took me a while to get to know them all. Once they figured I was going to be around for a while everyone was pretty friendly. Some dropped off while a few still remained. One in particular I'll call him Randy, he played the stock market and had done pretty well for himself. All he did pretty much was travel to locations for business and he made a pretty good living for himself. Both of them swore they had no romantic history although from a guys point of view I could tell Randy would definitely jump if given the chance.

Soon after relocating and meeting Madison I started a job off shore working on tug boats that went all over the south end and eastern side of the country. It was a great job with great pay, the only down side is I was away from home for so long at a time. Now I trust Madison and she has never given me a reason to doubt her. We constantly have phone sex when I am on the boat and off my shift and we shake the house when I get home. She always tells me of conversations she has and is always willing to show me texts. I don't need to look at them because 90 percent of the time it is people asking about either watching kids or somebody needing a ride or wanting to borrow money.

It was this job that sparked our conversations about her and I opening up because we have the understanding that we both have needs to be met but it's almost like neither of us wanted to be the first to do it. I was home for a week and Randy came by to say hey and chill out while we grilled and drank a few beers. He never crossed any lines and he was good company to have around. We got a little buzzed and the conversation of an old friend Frank came up.

Frank had moved away to Arizona few years ago due to work and I never really got the chance to meet him, but I had heard stories of him and the crush he had on Madison, although she would never give him the time of day for friendship sake. He was getting married and Randy was tasked with providing the entertainment and knowing of the crush that Frank had he wanted to give him a shot at what never was, that's where Madison comes in. Randy wanted the evening to be with old friends and didn't honestly expect Madison to agree to being the "entertainment" for the party. "I'm glad that Frank finally decided to settle down" Madison said. "Well Madison we are going to need entertainment and I don't know how to ask this but, after a slight pause and an audible gulp of nervousness, I was wondering if we could count on you to fill that spot." Randy said half expecting to get told off. He didn't give any details on what exactly that was but we are all adults and could figure it out. As the question was asked I saw a slight look of shock and then Madison looked away and bit her lip as if she was into the idea but didn't want to let on like she was.

Madison looked at Randy with a sparkle in her eye and replied "I don't know, can I talk to Ryan and discuss it with him? How long do I have to give you an answer?" with a slight bit of hidden excitement in her voice. This was her chance to do what we had always talked about and she realized it. After dinner and a few more drinks Randy said he had to go get ready for a trip he had planned, as Randy was walking towards the door he looked back and let her know she had one week to give him an answer so that he could book plane tickets or try to find another woman.

We cleaned up everything and didn't really talk much about it but we both knew that was the elephant in the room and we needed to address it. Later that night we had an amazing love making session where the topic of Madison stripping in front of all those guys came up and we also mentioned what could happen if things got a little wild. Madison came multiple times and definitely got a little wilder than usual.

The next day Madison and I had a talk over breakfast and she asked me the one question I was waiting on. "Would you be mad if I said yes?" she asked with a concerned look on her face. My response was very simple "We have always talked about it and I know it has just been in the heat of passion but it drives us both wild" I said with a grin just to let her know that it was now or never. She thought about it for a few minutes and I could tell that the idea really got her going.

"I don't even know what I would wear or what I would do, I never thought I'd be put into this situation." she just kind of thought out loud about how everything was going to happen. I took the conversation where we both knew it was going and told her with a sincere tone in my voice " I'll call Randy and tell him to book the flight just as long as I can be there with you just in case things go where you aren't comfortable."It was like a huge weight was lifted with me taking control of the situation as she smiled at me with that playful grin she normally gets with the thought about doing something we both fantasized about.

I made the call to Randy and let him know the stipulations and what we had agreed on and he was overjoyed at the idea of finally seeing Madison in a situation like this. "When you get off the boat after your next hitch go pick up Madison and be at the airport by 5pm" He gave instructions on the flight and let me know that all the expense was paid. My next hitch seemed like it would never end mainly because we spent most of it docked with not a whole lot to do. I talked to Madison pretty frequently and she had let me know of some shopping she had done and some ideas she had for the "entertainment" that evening. I pleaded with her to show me what she had planned but she refused and simply replied "Nope you gotta wait, it'll build anticipation." with a giggle in her voice and I could tell she was now looking forward to it.

Finally crew change day rolled around and I was packed and ready to go as soon as I got finished with breakfast. When I got to Madison something seemed different, more sexual than usual. Her 5'2 frame was covered in a pair of tight purple yoga pants that fit like a second skin with a white halter top. It was nothing to revealing or overly sexy but her aura was beaming with the power of a woman that knew what she wanted, her confidence was a turn on like nothing I have ever seen.

Our flight was pretty uneventful outside of the head turning that Madison was causing. Just a few hours later we landed at Marble Canyon Airport in Arizona. Seeing the Colorado river as we flew over before landing kind of took my mind off of what we where there to do. I was quickly snapped out of my daydream and back to reality when Madison let me know that Randy was waiting for us at the exit gate.

Madison was real tight lipped about all the details of her plan which made us all a little more anxious about what she had planned. "I haven't let Frank know yet so this will be a huge surprise when he sees you after all these years. I also have a local girl that will be there to help things go a little smoother." Randy said with excitement in his voice. As a joke I said "well I guess I gotta be good." as I winked at Madison who smiled playfully.

We made it to the hotel and I was taking a shower when Madison appeared naked and wanting to play. "Please fuck me so I can get my mind straight but I have a request tonight, please don't cum in me. You can all you want tomorrow night." She said as I nodded in approval of her request. We then proceeded to have one of the best hardcore fuck sessions that we have ever had. She has let me fuck her in the ass a handful of times but tonight she wanted it hard in all her holes. I could tell she was ready for whatever happened at the party.

The next morning Randy was there to pick me up while Madison stayed at the hotel to get ready for the nights events. Frank didn't know who I was so he still had no idea that Madison was in town or what she was here for. When I met him Randy had introduced me as one of his friends and we drove around trying to get food and booze for the party tonight. "Hey Randy, what time does this party start tonight?" I asked with curiosity and a need to know how long it was going to be before I saw Madison again. 7PM sharp was his reply.

Knowing what could potentially happen tonight had my nerves in a frenzy and my stomach was in knots knowing that this could be it, this could be what we had fantasized about all this time. I sent a text Madison to see how she was doing and her reply was a little surprising to me. "I'm grabbing lunch right now then I will be going back to the hotel to get ready. I hope you are ready ;)". I could tell that she was ready, and to think she would normally be the one with rattled nerves. "7PM sharp is when it starts, I'll see you around then I love you." I wanted to make sure that she was ready and it seemed like I was the one getting cold feet but I had my mind racing and an uncontrollable hard on thinking about it.

We continued to text back and forth and it was clear she was anxious to do this. Time seemed to fly by and soon it was 7 on the nose and the guys started arriving, in total 25 guys came and the liquor started flowing. We all sat around shooting the shit, telling bullshit stories and waiting for the entertainment to arrive. The doorbell rang and Randy went to answer it and the next thing I saw dropped my jaw to the floor. A blonde came in first her name was Ali and she was wearing a schoolgirl outfit that was short enough to see her very firm ass and the top revealed ample amounts of cleavage with material that was straining to hold back her breasts.

Next entered Madison wearing crotchless mesh stockings with a short blue jean skirt and a plaid shirt that was tied in front and had her long brown hair in a ponytail, not at all an outfit she would normally wear in public, that was a surprise worth waiting for. I thought that Frank was going to nut in his pants at the sight of Madison, considering that he hadn't seen her in what seemed like forever. He started to get up to greet her and before he could stand Madison put her foot on his chest and pushed him back down while giving him a clear view of her pussy under her skirt, and what a view he got as her skirt rode high up her thighs.

The music started and the girls started dancing and grinding on each other almost to the point of making out. Madison kept an eye on Frank and Randy as she would bend Ali over and act as if she was fucking her from behind. Ali made her way behind Madison and started to untie her shirt to expose her firm C cup breast. With her shirt off and out of the way Madison reached behind her and undid the clasp of her bra to give the full show. Sliding her arms out of her bra she made her way over to Frank and used it to pull his face into her chest as she shook her tits while bending at the waist to give the rest of the party a good view as the hem of her skirt barely covered her ass.

Ali was working the rest of the crowd pretty well. She got in front of me and bent over shaking her ass as she pulled her panties down from under her skirt showing a well trimmed pussy as she shook her ass. The cat calls were loud and excitement was definitely in the atmosphere. Madison mainly worked with Frank and Randy but also paid attention to the other patrons in the room. After about 45 minutes both girls were completely nude except for Madison still wearing her crotchless stockings and a jeweled butt plug that I hadn't noticed until she shed her skirt, she could be considered nude, nothing was hidden. Both girls were in the middle of the room teasing the crowd and acting as if they were going to go at it right there.

With the booze starting to get to everyone I noticed Frank unzip his pants and pull his cock out and I thought to myself this is it lets see how it goes. Ali got up to work the crowd and noticed Frank and froze in place. "I didn't agree to this. Our agency doesn't allow it so I gotta go." and with that gathered her clothes and looked at Madison and said "have fun honey." as she made her way to the bathroom to get dressed. So there was Madison essentially naked in a room with 25 horny men. Looking at me she just licked her lips and made her way over to Frank and sat on his lap asking him what he was going to do with his "big ol cock" as she ground her pussy on his lap.

Soon a lot of the guys had their cocks in hand and started jerking off at the sight before them. One of the guys pulled a bar stool into the middle of the floor and Madison was pulled to it and bent over ready to suck and fuck all cocks available. It didn't take long before Frank got behind her and placed the head of his long erect dick at the opening of her pussy which was sopping wet. "I've been wanting to do this for a while." he exclaimed as he drove every inch of his cock into Madison making her moan loudly at the intrusion. Randy got in front of her and while looking at me fed his cock down Madison's throat and started to fuck her face with slow deliberate strokes.

She showed no protest to anything that was happening and although Frank wasn't really thick he was long so I know he was reaching the bottom of her pussy while Randy was more of an average size so she was able to take her face fucking with little trouble. Frank must have been worked up good because it didn't take long for him to grip Madison's hips and really start driving deep into the tightness of her pussy making her moan with a muffled loudness through the face fucking she was getting. There was definitely a line forming and I wasn't going to pass up this opportunity to really give it to her good.

Frank started grunting and holding himself deep inside Madison and I knew he was cumming deep inside of her. He held her by the hips and grunted loudly as he finished as the next guy in line was waiting his turn. We didn't know anyone at the party except for Frank and Randy and at this point Names were the last thing on our minds. Frank pulled out and was replaced by a guy I would guess that he was of Island descent due to his complexion all I do know is he had a massive unit between his legs and Madison was about to get it. He was only about 7 inches long but easily as think as a coke can, as Randy finished cumming in Madison's mouth I saw her eyes shoot wide open trying to accommodate the massive intruder trying to work its way into her wetness.

She swallowed all she could of Randy's load and was soon biting her lip as the Islander drilled her from behind showing no mercy as he stretched her folds to limits that they have never known. The room was quiet except for the sounds of Madison Moaning and cumming and the sounds of skin slapping skin as each cock took its turn in dumping load after load of semen deep into my wife. Finally it was my turn and when I saw her pussy it was a frothy mess with cum dripping down her thighs and a slight gape from all of the cocks she had taken. I slammed my cock in her and after a few strokes I was going to see how far she was going to let this go as I pulled out and placed the head of my shaft at the entrance to her asshole. She pushed back and let out a groan as the head pierced her asshole for the first time tonight.

Seeing this gave Frank an idea and as soon as I shot my load into her bowels he had her straddle him on the couch as he entered her for the second time. A large black man about 6'3 with a slight pot belly got behind her to take her ass and as soon as she felt his size froze and asked him to go slow. I moved over to get a better look at the scene and holy shit he was huge. He worked slowly as soon every bit of his 9 inch cock was in her ass stretching her to the absolute limit of her tolerance.

Frank held Madison around the waist and slowly worked his shaft in and out of her as the monster in her asshole started to pick up its pace. With her face buried into the cushion screaming in pleasure the Guy in her ass had a good grip on her hips and was really starting to a good rhythm as he neared his orgasm cramming the entire length of his giant manhood into her bowels and flooding her with his cum. We all took turns with Madison through the night and soon things started winding down and Madison having pleased all these men multiple times needed a shower to clean herself up.

This is what we had talked about in all of our conversations. Maybe not on this scale but it finally happened. As I sat in the living room with Randy and Frank and a few of the other guys explaining to Frank that I was Madison's husband and how we had planned this I noticed that a few people were missing. I excused myself and made my way to the bathroom where I could here Madison talking to someone but I didn't know who. I heard her say "one more time and then I have to shower and get some sleep." The mystery guy said in a deep rough voice "OK but this time I want your pussy, so bend over that sink and get ready."

I stuck around by the door to hear what was going on when I heard Madison exclaim "Holy Shit that's huge" as she started moaning and I could hear the distinct sound of skin slapping skin while she was being fucked without mercy. I didn't want to get caught listening in so I made my way back to the living room and let them finish. After about 30 minutes I noticed the black guy coming down the hallway and that confirmed who I thought it was. Madison had finished her shower and told me she was going to lay down for the night. I couldn't blame her it was well after one in the morning and she had been fucking for hours. I lost track of time while talking and bullshitting with the guys when I was ready for bed. "It's been fun guys but I need some sleep I'm wore out" I said getting up and making my way down the hall to the bedroom.

The door was cracked and I could hear moaning and thought to myself surely not again. I peered into the room and saw Madison with her legs over the shoulders of one of the party goers as he was driving deep and hard into her. As he sped up his strokes and slammed into her one last time before dumping the contents of his balls into her unprotected womb I made my way back down the hall to make it look as if I just started making my way down the hall. As the guy opened the door and saw me, he just kinda smiled and let me know that there was a hot willing piece of ass in that room if I wanted it. Not knowing she was my wife because he was fucking her when that was revealed I grinned and said thanks as I walked into the room, closed and locked the door. Madison was laying on the bed on her back and looked up at me with a grin "God I'm glad it's you I am ready for bed" she said with a tired laugh.

We laid in bed and as I held her we both drifted off to sleep. The next morning when we woke up everyone had gone home Madison and I got dressed and ready to leave. Randy was getting ready take us back to the airport when Madison came out of the bathroom wearing a short sundress that would have shown everything if the wind blew the right way. Madison wanted to give Frank a proper farewell and asked if he could ride in the back seat with her. Shortly after we left the house Madison had straddled Frank and had his cock buried deep into her swollen and sore pussy as she rode him with vigor. They fucked like rabbits for 30 minutes before he finally dumped another load of cum in her shortly before we pulled up to the airport. This was the spark that opened our marriage and gave our sex life a new fire as we have both had multiple partners since then. That's a topic for another story and another time.