Middle Age Sugar Baby Ch. 01

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.

I spotted John waiving for me as soon as I deplaned in San Francisco.

John greeted me with a bid ole' hug: "Hey mom, I missed you so much, it's great to see you"

"Johnny', it's so good to see you too." I responded enthusiastically. I was surprised how genuine I meant it too. "Your such a handsome young man in your suit".

"Mom, you must be hungry. Do you want to stop some place to eat?"

"I'm, starving, but I need to find a bathroom to freshen up after three hours in that plane" Kathy replied.

"You look great mom, but sure, let me take that bag."

As easily as that, John and I started our adventure as mother and son. Driving from the airport and all through dinner we chatted pretty much as a mom and son would chat. It gave both of us the opportunity to catch up on each other's lives.

John said he was glad that I found Brian. He shared with me that he always felt like I had stayed single all those years because of him.

I told him I had no regrets about my life. I loved raising him and always hoped that he would have he opportunities he now has. I was very proud of him and wanted to know all about his new Job.

John shared the experience of landing his first real big executive role. The firm he joined was very traditional. John had shared many stories about how I had worked so hard to raise him on his own. He was anxious to show me off Saturday evening. He also told me how much he wanted to give me some of the luxuries that I had sacrificed in order to send him to college.

I was touched by the sincerity of John's story. I don't really know the story of his real mother or whether she is even alive. He didn't share that when we first met, and now that we had commenced our relationship I was no longer at liberty to step out of character in order to ask him.

When we got to John's condo I was truly impressed. I remember thinking I could get used to this pretty quick. The first thing I did when we got there was to call my husband to let him know I had arrived safely. I know Brian had a lot of questions I couldn't answer, but I let him know that things were going well.

I had my own bedroom and was happy for the chance to shower and get comfortable. John and I talked for a little while longer however I soon tired and went to bed. It had been an exhausting day and I looked forward to the solitude of my own space for the rest of the evening.

On Saturday John and I spent the morning shopping. Not many men want to spend a few hours shopping with their mom, but John seemed to enjoy it. I was getting lost in the role and enjoyed having my son spend time with me- not to mention spending lavishly on me. I wasn't sure how I would enjoy the evening, but the day had been wonderful.

Saturday evening turned out to be a delightful time as well. The formal dinner was a little boring, but afterward we had the opportunity to dance. I love dancing and to my surprise John was quite an accomplished dancer. We danced well enough together that I am sure his colleagues were completely sold on our relationship. Even his boss, who was a bit of a stuffed shirt, was a pleasure to dance with. This was going to be a fun way to earn some money.

I looked forward to returning to back to John's. He was very quiet on the ride back to his condo, which gave me time to think. John was a nice handsome man, and I was growing fond of him. He was also very good looking and I wondered how fast he would progress the relationship along its inevitable course. He didn't act like he was in any hurry for anything sexual and I had no idea how he planned to move in that direction.

When we got home, John finally broke his silence.

"Did you enjoy yourself mom?"

"Yes, John, very much. I had forgotten what a great dancer you are".

John chuckled, "You were the one who insisted I learn ballroom dancing mom. Remember the hours we would practice?"

"Yes, I enjoyed that time, I am glad you stayed with it", I replied.

"Well we better get to bed early, I usually leave for church my seven-thirty"

Church. That never occurred to me. I grew up with church, but long lost the desire to participate in any organized religion. I had not been to church in years, and when I did it was either for a wedding or a funeral.

"We are going to church?" I inquired, hoping maybe he was joking.

"Yes of course mom, don't worry, its not like I grew up with, it is a much more liberal theology. You will enjoy it".

"Well OK", I relented, but why so early.

"It is about an hours drive from here, don't worry we will have a relaxing afternoon. I have nothing else planned for your time here."

"Well, that's good", I said, honestly relieved. I will enjoy just spending some time alone together.

Sunday morning we took the drive out to church. We chatted a bit, but I was mostly enjoying the beautiful scenery along route 101 toward Santa Rosa. It was beautiful country here, especially when we got off the main highway and into the more winding secondary roads. 'This was certainly a long way to go to church', I thought.

We left the main road and went down an unmarked dirt road leading through the woods. We probably drove about three miles until we reached a large field with a single building on the top of the hill in the center of the field. This was certainly not at all what I expected. The 'church' looked more like a very large old house, at least on the outside. From the looks of the place I thought we might be a bit over dressed, but as I saw families walking up from the parking area to the church, I noticed that everyone was dressed in 'Sunday best'.

We parked on the grass with the other cars and walked up the hill to entrance of the church. People seemed friendly. It was apparently a small enough 'congregation' that they realized I was a new guest. John introduced me to several people as we walked inside.

The inside of the church was very simple, but beautifully maintained- much more so than the outside of the building. We were welcomed as we passed though the entry way and into a very large circular room. There were no pews, just a large number of individual chairs mostly placed in a semi-circular arrangement facing a smaller group of chairs in more traditional rows. John and I took our seats in the circular section, with John introducing me to a few other members along the way.

The 'service' was not really a service at all. In fact it did not really seem all that spiritual in nature to me. Perhaps it was a little too communal in nature. There was lots of talk about love and caring for each other, that sort of thing. There was some sharing from the group. I was perhaps the only visitor, so John stood up and introduced his mother and told them a little about me. He explained that this was my first visit but that I would be visiting often. Then things ended as abruptly as they began.

"So what happens now", I inquired of John.

"Now we leave and go back home", he answered

"Isn't everyone leaving now?"

"No, there is another session in the next room that is for members only, we can leave now".

"OK". I tried to not sound too relieved. But it all seemed a little cultish for my taste. At least is seemed very strange.

We drove home, mostly in silence. I was beginning to miss my husband Brian and would be glad to be returning home in the morning. The afternoon was pleasant enough though and I soon forgot about the uneasiness I felt at church. True to his word we returned to his condo and spent a quiet afternoon and evening there.

This was then end of my first weekend with my John. I reflected on a few things about this trip on my return back home. I enjoyed spending time with John and even enjoyed being paraded around as his mom. He was successful and confident and very loving to me. He liked to be in control in all aspects of his life. While he seemed to be able to share some intimate thoughts with me, I felt like he was always holding back a little. This must be part of his need for control- to only share what he wants, when he wants to.

In our very first meeting in Atlanta he had me agree to accommodate his sexual needs as part of our relationship. However he did not move in that direction at all during this trip. He is completely immersed in his character as my son. So much so that I almost felt guilty hoping he would move in a sexual direction. For this trip, it did not happen and I was not so sure that it would. Now I had a month to wait until I returned for a visit.