Escorting for My Boss

I met my first husband, Steven, through work. We were both at the same large company. Not long after we were dating we had a conversation about being open with our sex lives and sharing each other and swinging. I had been promiscuous before and during college and while I loved Steven I missed the excitement. We laid some ground rules about communicating before we did anything with others. In swinging situations we both had to be comfortable, whether it was a threesome, a swap, or a larger group. I readily acknowledge that this sort of arrangement is not for everyone. In my opinion, you an your partner/spouse need to have so much trust in each other and a strong, loving relationship.

At work we both were successful. I had climbed the ladder quickly to become an executive assistant for one of the big shots. Mr. Edwards (Jim) was in charge of many big deals for the company. He was a great boss to work for. We were fortunate enough to be invited to some social events that included him and his wife, Tiffany. Tiffany Edwards was a true trophy wife. She had "hobby jobs." She was involved with running a large charity ball each year. She is a gorgeous blonde - though not a natural blonde. Jim had purchased her an incredible set of breasts. She worked out like a fiend to maintain an incredible body, which made her appear at least five years younger than her age of 40. For the record, Jim was 50 at this time.

Steven had definitely taken a shine to Tiffany and I also found Jim quite attractive. While having pillow talk we often wondered how they would be in bed. We agreed that it could be dangerous to mix business with pleasure when it came to our careers. It just stayed a topic of conversation and even some fantasy.

Over time I learned that to "seal the deal" with gentlemen from other companies Jim would arrange a dinner date for the visiting business associate with he and his wife. He would have Tiffany invite a single girlfriend to be the date for his associate. One particular time Tiffany was not able to secure a date for the man coming to town. They both thought of me, feeling that my attractiveness and the level of class I demonstrated would work well. Plus, Jim had heard rumors about the relationship Steven and I were in.

Jim calls me into his office and asked me if I would go on the date and is Steven would approve of it. I told him I was in and that I was sure that Steven would be good with it.

In the week leading up to the dinner date some of the girls in the office were talking to me about it and they said they had heard that the visiting executive was expecting some sort of sexual favors. Jim had said nothing about that. I think he just assumed I would go with the flow if that's where it led. (He was right.)

Jim's wife, Tiffany, called me about my outfit so we would be dressed similarly yet different enough and not in the same color. Tiffany chose a slim, form-fitting, black dress with a halter-style bodice with a deep neckline and it was backless. It had a slit up to her thigh. She had on black hose and four inch stilettos.

I wore a dark green, satin, strapless dress. It was also tight and had a high slit. I opted for a garter belt and stockings - both in black, to go with my black heels.

Jim and Tiffany picked me up and then we swung by the hotel to pick up the businessman. His name was Ian. He was a tall black man from England. He had gone to college in the United States played basketball.

The drinks and dinner were marvelous at this very high-end steak house. We went to a night club after. The men talked business while Tiff and I chatted about woman things. LOL. She and I excused ourselves to the restroom. While I was re-applying my lipstick and giving myself a spritz of perfume Tiffany got a text from her husband. He said that Ian was smitten with me and hoped I would join him back at his suite at the hotel. I grinned broadly and to her that I would be happy to. I also confided in her about the openness of the relationship Steven and I had. She just grinned and gave me a hug.

After another round of drinks the Edwardses dropped us off at the hotel. We took the elevator to his suite. I took his arm as he offered it to me when we exited the car. I looked up at him with a big smile and gleaming eyes.

Once in his suite he helped me with my wrap and complimented me, again, on my dress and how nice I looked. He poured me a glass of wine as I looked out the window, onto the city. Ian came up behind me to hand me the glass. I felt his towering presence behind me and his body brush up against mine. My nipples felt like they had received an electric shock. Ian's large hand was on my hip. I sipped my wine and turned into his chest, with little room between him and the windows. I looked up and him and smiled. My free hand reached toward his groin. I felt a large lump in his dress pants. My eyes opened very wide as I couldn't believe the size of what I was feeling. He chuckled and told me not to be afraid of it. (I love that English accent.)

I assured Ian that I was not afraid but that I was, rather, very excited about the rest of the night. He looked at me and asked, "The whole night?" I replied with a squeeze of him and saying, "If you don't mind me staying the whole night." Ian looked at my diamond on my left hand and gave a quizzical look. I assured him that it was more than 100 percent okay. He then popped a little blue pill and commented about "going all night."

With that he leaned down and kissed me. His long arms enveloped me an his hans held my bottom. Our tongues danced and we sucked on each others' lips. I set down my wine glass and led him to the sofa. I unfastened his belt and pants and pushed the pants and his boxers floorward. I turned so he could unzip my dress. I made a hand bra as it slid down my body. I stepped out of it and turned to him and he grabbed my breasts and squeezed, causing me to elicit a moan and roll my eyes. I pushed him to sit and I knelt between his legs, with my dress under my knees. I grabbed hold of the massive black penis before me. I had not seen one that large before and I had been fucked by many large cocks over the years. I stretched my mouth as wide as it would go to just suck the head of this beast. I spit on it repeatedly and stroked his firehose with both hands. I looked up and his bright smile and nod encouraged me to keep doing the best I could at fellating this behemoth of a penis. I'm not sure how long I tried but I told him my jaw was getting tired.

With that he stop an literally swept me off my feet and carried me to the king-sized bed. He gently laid me back and spread my nylon-encased legs apart. He paid beside me and kissed my nipples while his long fingers teased my nether region. His oral skills on my nipples - licking, kissing, sucking, and nibbling - had me squirming in pleasure. There is a direct line of stimulation from my nipples to my pussy and I was getting wetter with each passing moment. I felt a long finger probe deep with in me, and then a second, and a third. He was stretching my slit. He whispered that he was preparing me to take his gigantic dick deep inside me. My hips were bucking. His thumb rubbed my clit and I burst into an orgasm, with creamy cum coating his fingers. I moaned and screamed loudly as I clutched at the bedding when the orgasm rocked my body.

Ian kissed his way from my breasts to my navel, and eventually down to my pussy. He spread my labia apart so his tongue could lightly flick across my clitoris, making me squirm and beg for more stimulation so I could once again cum for this gorgeous man. He orally pleased my clit while slipping fingers deep into my cunt. I then felt him take his pinky finger and he slid it into my backside. I erupted once more and my body convulsed and shook violently.

Ian backed off to allow me to catch my breath and regain my senses. Once I felt slightly recovered I was between his legs slobbering all over his cock, stroking it and taking his large balls into my mouth. His cum-filled nuggets each filled my mouth as I bathed them with my tongue and sucked on them.

Ian looked down and told me it was time for me to take a ride. I climbed up his body and I hovered over him and held his might meat stick in one hand as I very slowly lowered myself onto him. I felt his big hands on my hips, very gentle in guiding me onto him. Once the thick head was in I moaned and rolled my eyes back and then held them closed while i adjusted to his size. I slowly worked myself down, in what felt like a long time before I felt him hit my cervix, adjusting my body to his girth. I slowly started riding up and down on that glorious shaft. The sensations were mind-blowing as I felt every vein of his cock rubbing the walls of my slick cunt. I found orgasmic bliss more times as I rode him. Ian's big hands guided my hips up and down and began dictating the pace of the fuck. Before long I was riding him and panting as I moaned with each stroke. Ian announced that he was about to blow. I saw a look in his eyes and he thrusted upward with incredible force. His ejaculation was so intense that I could feel my flooded pussy dripping down onto his balls and into his pubes.

After we both caught our breath I asked if I could take a pic of his penis to send to my husband. He agreed, as long as I didn't show his face. Steven's reply message was a simple "OMFG!" I replied back with, "Amazing! I love it!"

We showered together and we put on the plush robes provided by the hotel. The clock showed midnight. I snuggled into Ian and we fell fast asleep. I woke up an used the bathroom. When I climbed back into bed I put his penis in my mouth and began sucking him. He awoke, smiling, and he ran his fingers through my hair. Once he was at full staff, I climbed atop him and laid myself down on his huge prick. It was easier after having been stretched by his massive dick and the creampie still sitting inside me. His large hands massaged my breasts to start. Then he grabbed my waist and hips and I felt like a rag doll as he moved me up and down his shaft. I was rolling from one orgasm into the next. Moaning, eyes fluttering, convulsing. Eventually I felt his powerful load blast deep within me as his hips lifted me off the bed.

Ian ordered us room service breakfast and I arranged a ride home with the service the company uses. While eating I asked if he had enjoyed other women provided by Mr. Edwards. He said that he had but that I was by far the best. He did also mention that he would love to have a shot with Tiffany Edwards.

Later that afternoon, after I had a relaxing bath and a long nap, I noticed I had missed a call from Tiffany Edwards. I called her back straight away and asked how I could help her. She was curious about my evening and was wondering if we could have coffee. I met her at a coffee shop in town. She was so curious. I told her what we had done and she was enthralled when I told her about his gigantic cock. In fact, she licked her lips without realizing it. I then told her that Ian was interested in her. She confided with me that Jim had just flown out for a meeting out on California. She asked if I would come with her to Ian's hotel. I readily agreed.

More to come in part two.