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How I Became A Courtesan

Long story, but here goes.

About 3 years ago Michael and I began talking about our fantasies and we both shared the fantasy of me with another man. We talked about it a lot, and eventually decided to place an ad on another swinger site and see what happens.

Well, we received many responses from guys, most not very good ones, but we enjoyed the process and I enjoyed having Michael help select another man to share our bed. Like many people new to the lifestyle, we wondered if we could really go through with it or if it should remain a fantasy.

Well, one gentleman in particular stood out, a man from Chicago that was coming to town for a convention. He was very persistent, very attractive, and seemed like a good candidate. We were hoping to find someone from out of town, not having to worry about them becoming a nuisance and all.

He was to arrive on a Friday and invited us to join him for dinner at an upscale French Quarter restaurant called Louis XVI with his sales team, even better for us because surely he must be safe if he’s going to introduce us to his employees. He even said he’d send a limo to pick us up from our house.

Still, I was a little apprehensive, my conservative upbringing and natural fear of the unknown was getting the better of me. The excitement was real and Michael and I spent most of Friday shopping for the perfect dress and sexy things to go along with it, got my hair and nails done, all the while feeling like a queen. We found the perfect red evening gown and a wonderful pair of heels to match. Michael is wonderful at knowing what looks good, and as always he found the perfect outfits for later that night, a burgundy bustier with garter, stockings and heels, as well as a few other things to make the night special.

As wonderful as all this made me feel, my nerves were getting the better of me. I told Michael that I was having some serious reservations. Michael would never pressure me to do anything, so he called our gentlemen friend and told him that we would not be able to make it, that my daughter’s father had bailed on watching her that night and we would have to stay home with her. To our surprise, he asked how much money it would take to pay my ex to watch Olivia. We told him that we would talk to my ex and get back to him soon.

Well to be honest I’ve had a call girl fantasy for quite a while and the thought of someone paying for my pleasures was enticing, and more than enough to relieve my nerves..Lol. Michael called him back and told him that my ex had agreed to watch Olivia for $300, and to make it more exciting, we asked John (I know, great name for someone that would help me live out my fantasy) if when he gave us the money we pretended that it was payment for services rendered. He readily agreed to play along.

We spent the rest of the afternoon getting ready, it was so exciting having Michael there helping me, making sure my makeup, hair and jewelry were just right, trimming my pussy, and making sure everything was just right for another man to share. Time flew by and before we knew it, the limo was at the door.

The ride in was exciting, the limo was well stocked and Michael and I enjoyed a few drinks, the nerves lessening, Michael never taking his eyes off of me or the smile off his face.

Once at the restaurant we were led to a private room where John and his employees were just settling in for dinner. Michael was introduced as John’s old college buddy, and we settled in for a wonderful dinner.

Soon we were through with dinner and John, Michael and I headed out to the limo. Our next destination was Harrah’s Casino for a little Black Jack. Once inside the limo, John and I sat next to each other in the back while Michael sat near the bar and poured us fresh drinks. John looked into my eyes and we slowly began and deep passionate kiss, his hand touching my knee, then moving slowly up my thigh. I could see Michael out of the corner of my eye, the smile on his face reassuring as I began to let myself go. As John’s hand reached my pussy, I could tell my panties were soaked. My hand began moving down his chest and stomach, and when I reached his pants, I could feel the reaction I was having on him.

Slowly, I unbuttoned John’s pants and slid my hand inside, feeling his cock for the first time. Through our chats during the past week John had mentioned that he had a rather large cock, and once my hand was on it I knew he wasn’t lying. As John and I continued to kiss and as I began stroking John’s cock, I glanced at Michael through the corner of my eye. The smile on his face was undeniable, and I could tell from the look in his eyes that he approved and that I could let myself go.

John broke our kiss, his hands now caressing my breasts, as he pulled down the spaghetti straps on my dress and began to kiss and suck my nipples. I was able to lower John’s pants enough for his cock to pop out; my God his cock was gorgeous! With John’s fingers in my pussy and another hand squeezing and pinching my tits, I could feel my clit throbbing and could hear the wetness of my pussy.

After staring at John’s cock while he pleased me, I knew I needed to taste it. Pushing him back into the seat I got down on my knees, his cock now only inches from my waiting mouth. I glanced over at Michael one more time and could see that he was rubbing his cock through his pants, the smile still on his face. I pride myself on being very good at sucking cock and it took all my skill to slowly guide his huge cock down my throat. Slowly I moved up and down on his cock with my mouth, rubbing his balls as I did. I could feel him thrust up to meet my mouth every time I guided him in.

Out of the corner of my eye I could see outside the limo’s windows, we were now driving through the French Quarter, thousands of people walking past the car, unable to see me be bad, but clearly visible to me. Michael had now moved over and sat next to John, and I continued to swallow John while making eye contact with Michael. John’s breathing was really picking up and I was sure he was about to cum, but just as we were at that point, Michael announced that we had arrived at Harrah’s.

We all quickly rearranged our clothes, just in time for the limo driver to open the door for us. Once inside the Casino, John gave me $500 and I joined him in the high roller section of the Casino for some $50 minimum bet black jack. He gave Michael $500 and Michael, who is not a gambler headed to the bar. Sitting there at the table with John was magical, wearing such a gorgeous full length evening gown, all my best jewelry, and my hair and makeup just so, playing footsie under the table with John, my mind drifting back to the limo ride. I turned my $500 into $1500, John won about $4000 and after about an hour we decided it was time quit gambling and head back to the room at the Ritz Carlton.

The limo ride back to the Hotel was just as fun and soon we were in his suite at the Ritz. While the gentlemen fixed us another round of drinks, I retired to the bathroom and changed into the burgundy bustier that I mentioned earlier, complete with Fuck ME pumps, and made sure my hair and makeup were just so.

When I came out of the room, my men were sitting on the bed and I moved over to John and standing between his legs began to kiss him. His hands were all over me and I could feel his already hard cock against my leg. Quickly I was on my knees and his pants were coming down. As I began sucking his cock, I could hear Michael getting undressed, and soon he was behind me, rubbing my pussy through my panties, reaching around and offering my tits to John. I continued to suck John, tasting his precum in my mouth, as Michael removed my panties. Michae’s tongue was quickly inside me, as John’s cock strained my throat. I was in heaven; remember this was the first time I’d ever been with two men at once. My pussy was on fire.

After a few minutes of this wonderful position, we all stood up and I turned around and gave Michael a deep wonderful kiss. There is something so erotic about kissing your husband right after having another man’s cock in your mouth. I stood between them now, kissing one, then the other, their hard cocks pressed against me, their hands exploring every inch of me. John lay back on the bed and I moved up between his legs, sucking his cock with my ass in the air in the doggy-style position. Michael moved in from behind and slowly slid his cock inside me. It absolutely took my breath away. Our fucking quickly was in unison, each stroke on each end perfectly timed. It was at this point I came for the first of what would be 5 times this night. Although my men could tell I was coming, the both held back, saving their cum until they were ready. After I came, we took a slight break, all lying in a pile on the bed. Soon I was ready again, and since Michael was lying on his back next to me, I climbed on top of him and began 69ing him. My pussy was still soaked, and Michael’s hard cock tasted so good with my pussy juice still on it. John just watched us for a while before I looked at him and asked him to fuck me. Still in the 69 position, John expertly guided his cock into my pussy, Michael’s tongue working feverously on my clit. This was the most intense sexual feeling in my life, and once again I was cumming furiously, my wetness covering Michael’s face and John’s cock.

After a small break and a change into another sexy little lace outfit, I was ready for more, and ready to make my men cum. Jumping between my guys, I would kiss one deeply, then the next, their cocks standing at attention for me. I moved off the bed and got on my knees, both guys now standing next to me, their cocks at my lips. I moved from one to the other, sometimes straining to take both at the same time. I never broke eye contact with them as I sucked them, looking into their eyes, sensing that they both were about to cum. I asked John how he would like to cum and he said his favorite position was doggy-style. I moved over to the bed and put my ass in the air and looked back over my shoulder at John. As he neared me he asked if I would like Michael underneath me again. HELL YEAH! was my response. Once Michael was positioned underneath, John slowly guided his cock into my dripping hole. I could tell that he was teasing Michael more than he was teasing me, since Michael had such a wonderful view of his wife being fucked.

John’s thrusts were steady and soon began to build in speed and intensity. Michael’s tongue also picked up the pace, and I could tell from the amount of precum he was leaking that he was about to fill my mouth with joy. I could hear John’s breathing picking up and I looked up to notice that I was staring right into a mirror. I could see Michael’s cock buried down my throat, and clearly see John pounding me from behind. Suddenly John screamed that he was cumming, and that announcement immediately caused Michael and I to do the same. There is nothing quite as enjoyable to me as that feeling of a cock exploding in my mouth. I can feel each wave as it moves up the shaft, then my mouth fills with a hot salty load. Each burst brings more until I’m ready to swallow it all. At the same time I could feel my wet pussy getting wetter as John unloaded inside me. It’s amazing how wet and slippery it gets when someone shoots inside me. You’ll have to ask Michael how he enjoyed being so close to the action that he could taste it. Needless to say, making two men cum at the same time sent me into a frenzy that I’ll never forget. I knew at that moment that I wanted to do this again.

Well, we fucked several more times that night, in fact we fucked until we noticed that the sun was coming up the next morning. John needed to get to his convention and Michael and I needed to go home, so we all hopped in the shower (and one more quick fuck), and Michael and I were dressed and ready to head to the limo for the ride home. As we were leaving John handed me an envelope and Michael and I went down and got in the limo. Michael and I sat in the back of the limo now, the same place where I had first tasted another man’s cock, and we just leaned against each other and smiled. At that moment I noticed the envelope that John had given me was sticking out of my purse. I reached down and picked it up. Inside were 30 $100 bills. Michael and I looked at each other and were stunned. Along with the $1500 from playing black jack and the $500 Michael was given, that was $5000 for a wonderful night of pleasure. We hugged and kissed each other then fell fast asleep in each other’s arms for the ride home.

Well, it was later that week that we wrote our ad and that is why our user name is what it is. John came back 2 more times, both great experiences that I’ll share at another time. He has since moved on, but we hope he comes back again one day. We’ve never had any luck duplicating our first experience with anyone else, but we hope one day we will. As a side note, John was always interested in bringing another female along for the ride. If he ever asks again are you two interested?

I hope that answers your question,

Stephanie

End of Story