The Sissy Life

Chapter 1, The beginning

I married a beautiful lady younger than me, the second marriage for both of us. She is a successful lady in her own right, I was getting ready for retirement. We were not the young couple that you find in most of these stories. She was only 58 and had not been with a man in 18 years when we met. I had just got out of a bad relationship, we both were looking for something long term. After a few months we knew we would be together for life. Married in less than a year, one thing was missing, she needed more sex, ie, a man with stamina. We joined a swinger site and met other men and couples, our sex life became, me watching other men fuck her. What follows is my best recollection of what happened after we met Tom. Our ad on the lifestyle website said we were looking for a well endowed bull.

We met Tom for dinner at a nice steak house he had chosen. We had exchanged photos prior to meeting, he liked how my wife looked. There were no nudes or anything like that, this was a first class guy, 52 very attractive 6`2, 200, in great shape and as we would find out well endowed. He was a perfect gentleman,he was in charge from the moment we met him. He had an air of dominance I had never seen before. I noticed how he ignored me and kept all his focus on my wife, Barbara. As the evening progressed it was clear he was taken with her and her, him. At times I felt invisible but he made it very plain he was only interested in us as a couple. I found that confusing but if she was happy, then I am happy. He made it clear that he wanted to explore all possibilities with a couple, including sexual. He asked us to go home and discuss it and if we wanted to proceed, he would like to come over this coming Friday night to get well acquainted. We both were confused by his desire to have us both involved sexually, it was obvious to me that she wanted to see more of this man and I did as well.

Friday evening could not come fast enough, we were intrigued. Tom arrived at 6 sharp, handing me a nice bottle of wine and her a bouquet of flowers. He told me to open it and bring glasses. I was taken back a bit by his demand, yet it felt right in a way. I served dinner and we had a great conversation. He is the president of a large sales company that does business all over the world. I explained I was retired and did all the housework and cooking and Barbara was still working from home and hoped to retire in a few years. Looking around he complimented me on how good a housekeeper I was and how I cook.He said I should be wearing a maids outfit and then we all laughed.

After dinner, I cleared up the dishes and cleaned up while he and Barb went into the living room. When I was finished they were sitting very close on the sofa deep in conversation, her hand on his upper thigh. I could see the outline. I thought of his cock, Tom looked up and said, "Jim,refill our glasses". Then returned his attention to my wife. When I returned, they both looked up and he told me to sit down. He said" I understand it from your wife, you guys are much in love but sexually things are lacking, I find you both to be what I am looking for, a mature woman that is beautiful with a submissive husband who can not sexually please her" I started to object and he held up his hand saying: Wait till I finish." He went on to explain that in his job, he travels a lot and does not have time for a traditional relationship. He prefers having a couple that are responsive to his sexual needs and that we should both be available when he calls. I started to object and explain that I am not gay and into men at all when my wife looked at me, with the hush up look. She said " I told him how much you like eating the creampies men leave in my pussy and how you like to suck the cum off their cocks' '. She even told him how I liked for her to use a strap on, on my "sissy pussy", as she calls it. I did not know what to say, my face must have been red because they both started laughing. Then he said '' look he is rock hard", looking down I saw that he was right. My pants were tented out and I was harder than I had been in years. I was so confused and didn't know what was happening. There was something about this man and how he took complete control that seemed to make me want to please him. I could see my wife was taken with him as well.

What happened next is a bit of a blur. He turned to my wife and kissed her passionately while sliding his hand under her blouse. I knew she was not wearing a bra, his hand was on her firm breast, a moan escaped her lips. When he broke her kiss, he looked at me and said "it's time for you to get to work". He pointed to his crotch, for some reason I understood what he wanted. Dropping to my knees I undid his belt and unzipped his pants. He was not wearing underwear and I fished out the biggest cock I had ever seen. It was about 7 inches simi soft. Taking the head in my mouth. I knew my life had changed forever. There was a little pre cum that I licked off as his cock began to harden., so focused on it I did not realize my wife was watching, I had it about half way in my mouth when I looked up and saw her smile at me. I don't know what to think, was she pleased or laughing at me. Then she said the words that changed my life" see Tom I told you he would make a good bitch for you".

When I had sucked his cock till it was too big for me to handle, he told me " I needed to work on my cock sucking skills because it was the only sex I would be getting from now on". Barbara told me I would be sleeping in the guest room when he visited and that he expected me to move my clothes to the guest closet. The master bedroom was for Tom and her, as he was the master from now on. I was so humiliated I had no idea what to do, yet my cock stayed rock hard. Tom explained he and Barbara had decided he should stay the night, so I would be sleeping in the guest bedroom. I laid in the bed listening to their love making, he squeals of pleasure and delight, I had never heard before. It was humiliating and in some sick way very exciting. I jacked off twice as I listened.