Middle Age Sugar Baby - Mom/Son Ch. 01
My name is Kathy. Most of these stories stand alone, but you may want to read the introductory story first to get a better background. The stories focus on my midlife journey as a sugar baby. They are inspired by real life experiences, but are still largely a product of my imagination. In other words I took literary license to deviate a bit from actual events. What is authentic is the fact that at middle age I entered into a sugar baby lifestyle. The feelings and emotions I experienced are very real, even if I have altered the characters a tad...
John wanted a sugar lady for a very particular role-play. He wanted someone who would play the role of his mother. His expectation was that he would fly her out about once a month or so and she would stay with him for a few days. During that time, they would go out socially as mother and son. This could include business as well as social events. So he needed a very sophisticated lady that could convincingly maintain the role-play 24/7. In between visits they may write or converse by phone, but always 'in character'. He wanted to be able to introduce her to his friends and colleagues who would then get the impression that he had a very happy, healthy relationship with his mother.
So far that was very easy. I enjoyed role-play and am actually quite good at remaining in character. I am well traveled and comfortable in all social situations. Of course as expected this was not the end of the fantasy for this young man. He also wanted a sexual component to the mother-son relationship. I know I surprised my husband Brian when I did not hesitate to agree to this. He was quite use to me having a sexual relationship with other men; He just didn't think I would go for the role-play this particular man wanted.
Brian and I are a lifestyle couple who have lived in an open relationship for most of our time together. Best friends since childhood, we have shared some amazing experiences. We enjoy exploring all kinds of new erotic adventures, though this foray into a sugar baby life was relatively new for us. Even at 52, it was providing a new erotic thrill that was both lucrative and exciting. It opened me up to a refined lifestyle that I found exhilarating.
By this time, I had experienced a couple of Sugar Daddy encounters, but they were with much older men. These were new experiences for me: Being involved with men both geographically and culturally distant from my husband. I enjoyed the financial benefit, the lavish gifts, and the company of successful, culturally refined gentlemen. I was not really physically attracted to either of my two previous sugar daddies, but the sex was still thrilling in its own way.
John would be quite a different encounter for me. I was very attracted to him sexually and looking forward to that aspect of our relationship. His kinky taste in role-play was not especially a fantasy of mine, but a role I felt I could put myself into. I have children, but honestly never fantasized about them sexually.
My Husband had come to enjoy my first two encounters. Although hesitant at first, he knew they were both married men, neither of which was particularly attractive to me sexually. John; however, was single, much younger and definitely a carnal attraction for me. In addition, there is always the safety issue. I met my first two sugar daddies alone, on our first encounter. However, my husband preferred that he met John before flying out to the west coast.
So for this first meeting John flew both of us to Atlanta Georgia. We all stayed at the Westin downtown. We were comfortable there- it was an upscale hotel downtown that we had stayed at a few times in the past. We had dinner that first evening and hit it off with John right away. He was a good-looking young man, very true to the pictures in his profile. It quickly became apparent how such a young man enjoyed his level of success at such an early age. My husband was very impressed with him. John carried himself very confidently without being arrogant. He was very skilled socially and I suspect he will be very successful in his life. More importantly I took a liking to him right away, and there are few men that I instantly form a bond with. My husband and I both left the next day confident that this would be a safe, fun and possibly even financially beneficial relationship.
When we returned home we contacted John once again and let him know that we were ready to move forward with the arrangement. He replied immediately and let us know that he too was looking forward to beginning our new relationship. He stated that he would draft a letter outlining his requirements. If we found the agreement acceptable he asked that we acknowledge such within 7 days of receipt.
A few days later we received a letter with a rather formal agreement attached. The agreement stated that I would make myself available to John several times each year, not to exceed once per month for up to three days per visit. At least one of those visits could extend up to a week at his discretion. John would arrange and pay for all transportation costs. He would also provide me with a monthly stipend of $2,500 for incidental costs. He may also provide me other gifts at his discretion. I would normally be expected to stay with him and dine with him, but should the trip require other arrangements, John would pay for all expenses. During the period of the agreement I was not to enter into an agreement with any other sugar daddy.
The agreement also outlined very specifically what he expected from me: Once we accepted the terms of the agreement, we would always interact with each other as mother and son. This would include any communication in between visits as well as during the visit itself. At no time during the year would any of us step out of character. In essence, I was to be his mother. Likewise Brian as my husband would only interact with him as his step dad. Although he did not have any plans for Brian to participate in any actual visits, he left that option open.
A great deal of the agreement provided a shared history that matched with things John had previously told his acquaintances. This includes anecdotal stories about his childhood and relationship with his parents. I was to memorize this and include it in our role-play. John never knew his real father, but was raised by a single mom for most of his childhood. They were very close, until he moved to San Francisco and she re-married a short time afterward.
Finally the agreement covered the more personal expectations of this relationship. He would slowly steer the mother and son relationship into a discrete sexual liaison. In our earlier meeting we had discussed how I was to be reluctantly lured into this. I was also not to share the sexual aspect with anyone, including my husband.
My husband Brian found this last requirement strangely exciting. He would only know that his wife was going to visit John, but he would not know if I was having sex with him. It would be very different than any of our swinging experiences where I would normally come home and share my experiences with him. John also left open the possibility that Brian might somehow be brought into the fantasy, but there were no promises in this regard.
We agreed to all the conditions of the agreement and John made the arrangements for the first trip to San Francisco five weeks later.
In the interim John and I chatted by phone once or twice per week. This gave us the opportunity to get into our mother-son roles and 'reminisce' about our shared life. He would also text me quite a bit, something I found a little annoying- I am not much into texting. But gradually I was getting into the role, even updating my husband on our son's activity from time to time. At home Brian and I continued the role. This was simply a means to help me in my role-play.
Over time though a friendship started to develop and my husband really got into his role as well. Sometimes, though less frequently, John would call Brian and chat with him. So we learned a little about John's work, his friends, his hobbies, etc. This helped alleviate some of the anxiety Brian still felt about having me travel alone across country to see a man he really didn't know all that well.
When the day arrived for me to make my trip, I was comfortable, and a little excited about this whole idea. Brian drive me to the local airport and felt pretty content until I actually had say goodbye and pass through security. At that moment I could see that he was a little uneasy. I tried to reassure him that I could take care of myself in any situation.
The first leg of the trip was a small commuter flight to Atlanta which is never very enjoyable. But the flight from Atlanta to San Francisco in first class was great. I sat by a young lady on her way back to school. She was studying at San Francisco State University. I enjoyed the opportunity to explain that I was flying out to visit my son. It was a great opportunity to practice my knowledge. I think I did well as she remarked at how proud I seemed to be of him. In a strange way I was. I was starting to get into the role.
