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 series focuses on my midlife journey as a sugar baby.
From "Middle Age Sugar Baby...The beginning of a new adventure."
There was something strangely exciting about this first sugar adventure. On the one hand it was a mutually beneficial business arrangement. I would get an allowance, the opportunity for travel, the benefit of some wonderful gifts, and some upscale social opportunities I would otherwise not have. On the other hand I was having sex for the pleasure of strangers. On top of all this my husband of 35 years was OK with it. Brian even seemed to get enjoyment from it. He also enjoyed a few days per month to play on his own- the benefit of an open marriage.
"From Middle Age Sugar Baby...Mom/Son Part One"
In part one of 'Mom/Son' I introduced John as my most recent Sugar Daddy. 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 me out about once a month or so and I would stay with him for a few days. During that time, we 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 we would write and converse by phone, but always 'in character'. I understood that at some point I had to be open to a sexual component; however he did not move in this direction at all during part one. John 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. In part one, it did not happen and I left wondering if it would.
And now, Middle Age Sugar Baby...Mom/Son Part Two
This Sugar experience was unique: For one thing John was only 27 years old. I was now 52. While the age difference made it easy to play the role of 'mom', it was strange to have such a young man in control. No matter how well I played mom, the fact is John was my sugar daddy. In that role he had a lot more say in our activities. At least that is how I felt. I was still a relatively new sugar baby, not sure of what my limits were. In my two previous sugar baby experiences, both with older men, I was fine just going with the flow.
The other strange part of this experience was that John never left our mother son role. There are now so many things I realize I should have asked him before we hit the start button on this adventure: What type of mother should I be? Did he want a mother who was more controlling? Did he want his mother to punish him? He mentioned that I should be accepting of a sexual relationship. Did he want me to initiate this? Did he want it to be consensual? There are so many things I just didn't know. Now, he refuses to leave the role-play to discuss these things...even for a moment.
As for my husband, we live in an open lifestyle relationship. We are both very sexual people who enjoy sexual experiences with other people as well as together. We both have our various interests and fantasies and the Sugar experience is one of mine.
Which brings me to the third odd thing about this sugar relationship: John's church. Brian and I are not particularly religious people, so I had not been to church in a while. My son's church was, as he called it, a very liberal order. I couldn't put my finger on it, but there was something about it that didn't set right with me.
Well enough of my pondering...back to being mom...
It had been a month since I had visited my son John. He had been so busy in his first year in San Francisco that we had not seen each other. But he promised now to fly me out once a month to visit. I was eagerly awaiting my second visit, now only two days away. He has had a great start to his life since joining his new firm. At twenty-seven years old, he was already seeing the fruits of his hard work, first as a student and then in his first job here in Atlanta.
I had hated to see him move away to California, but we each needed to move on with our lives. After many years as a single mom, I finally remarried. John seemed to get along with his step-dad. Brian was as proud of John's success as I was. Interestingly they both chatted by phone from time to time as well. Brian said he was just playing along with the fantasy.
During the weeks following my visit John and I talked by phone every two or three days. He kept me up to date on his job, and his church. He didn't seem to have much of a social life outside of those two venues. I tried to pry a little more about the church, but he insisted I would be more comfortable with it as time went by.
I kept him up on my life as well. John's step dad and I keep a pretty busy social life, enjoy dancing, and when we can afford it, travel. Other than that there wasn't much to talk about. The lifestyle aspect is not something that one shares with their son, so John and I never talked about it.
John wanted me to stay longer on this next trip. Although I didn't like being away from Brian that long I agreed to stay for four nights this time. He suggested I pack light, since he had a fun shopping day planned for me. He suggested I might even want to keep some outfits at his condo so I didn't have to travel with checked luggage each month. He had a free bedroom that was just sitting there empty anyway, so I should feel free to leave some items there. John insisted I would feel more at home when I visited.
I wasn't sure if Brian would like me leaving clothes there or not, so I thought it best not to bring that up. Instead I packed the usual suitcases with clothes I was comfortable with. In truth I figured if I left anything at John's it would be my old clothes. I wanted to bring the new clothes home.
I left Atlanta early Saturday morning. Flying first-class is a luxury my husband and I have rarely had. So when my son fly's me out to San Francisco first-class it is a real treat. This makes flying cross-country each month a pleasurable experience.
The choice of a Saturday-Wednesday trip was John's; however it worked for me. I could have passed on the Sunday church day though. At least I would get that out of the way early. I arrived Saturday before lunch local time, so John and I had a pretty full day. We had a nice lunch together before driving in town to his condo. Even though it was early, John had some frozen banana daiquiri's ready for us to enjoy.
"Wow, you painted the guest room", I announced.
"Your room mom, whenever you are here at least. I want you to feel comfortable here. Maybe this week you can help me pick out some more appropriate furnishings"
I plopped into the couch in the living room. "Oh, your furniture is just fine", I insisted.
"Well, we'll see, maybe you can help make it more like a home away from home", he replied with a smile.
John was always very well dressed in public. Even in the more casual settings he wore business attire. However at home he preferred the shirtless/seat pants look. It was a stark contrast, but a welcome one. As John stood across the room, his 6'1" muscular frame was pleasant to look at. Like many Italian men, John had olive skin and dark black hair. He shaved both his chest and back. I was curious how he managed the latter. I found him to be very handsome indeed. I am guessing he is second or third generation American because I did not really pick out any signs of an Italian accent.
In contrast, I did not really look much like John at all. I wasn't sure his friends found that strange or not. At 5'6" I was definitely not short, but in most other ways I contrasted quite a bit with John. My skin was milky white, and I rarely attempted to change that by tanning. I wore my hair blond, but my natural hair was also very light. Even my blue-green eyes stood in contrast to my son's very dark, almost black eyes. I was no longer thin, but carried 148 pounds pretty well thanks to long nicely shaped legs and large DD breasts.
"So tell me a little more about this church. I assume we are going again tomorrow."
"Well mom, there is not too much to tell really. But of course, we will be going. That will become a regular part of your life while you are here. You will get a chance to socialize a little bit more tomorrow. Last time you were here, they had a members meeting right after. Tomorrow we do not have to rush off."
