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Middle Age Sugar Baby Ch. 01

By: justgeena



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.

Middle Age Sugar Baby Ch. 02



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."

I was pretty sure there was more to it than that. However, the daiquiri I was drinking had a mellowing affect on me, so I just let it go. John could be very mysterious, but I was growing very fond of him. He was comfortable to be around and genuinely seemed to care for me. I loved the idea of my mini little vacation on the west coast each month and I had new clothes, jewelry and an allowance to boot. 

John kissed me good night and I headed to my bedroom. It was Saturday night, so no point in trying to call my husband. I knew he would be out enjoying the single life for a night. I felt a little lonely at that moment. It was strange being far away and sleeping alone. John was in the other room. I removed my clothes and climbed into bed. I don't know if it was the drink, or the loneliness, but was feeling horny. I reached down to pleasure myself for few moments, but quickly tired and fell asleep.

The next morning we enjoyed breakfast at home before heading to church. The church was in a secluded wooded area about an hour north of the city. Last month I recall a moment of panic as we left the secondary road and entered the dirt roadway through the forest. Today I had no such misgivings. I remembered the drive would be another few miles before the relative darkness of the woods gave way to the bright open field with the single building in it's center. About a dozen or so vehicles were already parked at the base of the hill below the church.

A few members where making their way up to the church as we got out of the car. They turned and hesitated, waiting for us to catch up with them so they could greet us.

"Hello John". A young man, about John's age called out to us. "You brought your Mom with you. Good to see you again, was it Katie?"

"Kathy" I corrected. The young man was a tall and very good-looking young man.

"I'm Paul," he offered. "You remember my mom Sandy"

"Hi Sandy, good to see you again", I replied, not really sure I remembered her.

"Hello Kathy, I am so glad John brought you. Maybe we will have time to chat after service".

Sandy was very well dressed, but I thought she could use a make over. She was perhaps my height and very thin- not very many curves. She had a pretty face and smile, but obviously did not like to use make-up at all. Her dark shoulder length hair was simply parted in the middle and combed straight down. She didn't wear any jewelry save for a simple choker necklace. 

We continued our walk, exchanging pleasantries along the way. As I glanced around I noticed that many of the lady's were also very conservatively dressed though some wore more jewelry than others. Oh well, I was a more colorful person and preferred that to show in my dress. 

The 'service' itself was not so different than before. A group of maybe 30-40 formally dressed people gathered in a very informal setting. There were a few readings, lots of discussion, but no formal ceremony to it. From the announcements I gathered that there were more formal rituals conducted at other times, but it was difficult to ascertain what they were. 

Apparently there were many different levels of membership. I looked around to see if anyone wore any special symbols to signify what level they were, but there didn't seem to be any. Everyone was dressed in similar fashion- men in suits, ladies in dresses. 

After the service, I caught up with Sandy in hopes of learning more about this place. Sandy was friendly by soft spoken. I loved her dimples when she smiled and thought she should do that more often. She was enthusiastically open about discussing the church.

Apparently the church was started by a group of successful millennia's. They sometimes refer to themselves as the Church of the 5th Commandment. The members are all in their 20s and 30s and grew up in working class families. Most, but not all, came from single parent homes. These children are grateful for the sacrifices their parents made and are now in a position to return that gift. All 'First Level' members are fully supporting their parents. 

"My son, Paul is a 1st level member", Sandy offered. 

"You mean you are both first level members?" I inquired.

"No Kathy, it does not work that way. Only sons and daughters can be 1st level members. You see I raised Paul as a single mom. Now he is supporting me. Of course, I live with Paul and he provides for all my needs. Most of the young people you see here are doing the same for their parent's. 

I just nodded as she continued. 

"Your son John seems like a very nice man. We have known John for some time, but only recently has he introduced you to us".

"Yes", I said. "John was very busy the first year out here with his new Job. We are very close, but I did not get to see him much during that time. Now that he is settled a bit he will have me out more often".

"Oh I hope so", Sandy replied. "I think you will like it here. John talks very fondly of you. He seems like a good boy who would take good care of his mother. Paul takes very good care of me. I do not have to worry about anything. So we hope to being seeing much more of your in the future Kathy (pausing)...enjoy your visit with your son".

Sandy gave me a big hug and kissed me on the cheek. I was surprised at the intensity of the embrace. 'Hmmm, wonder if she is bi', I thought. Smiling I winked as she turned and walked away to rejoin her son. There was no sign that she understood the unspoken question. 'Oh well, silly me', I thought.

I searched out John and found him talking with some of the younger members. Not wanting to interrupt I just hooked his arm and stood behind him. We all said our goodbyes with hugs and little pecks on the cheeks. John took my hand and walked me to the car. Once inside he inquired about my discussion with Sandy.

"Oh, she just told me a little about her and her son and a little about the church." I answered. "Sandy is really his mother right? I asked.

"Of course she is mom".

"John, she told me he takes care of all her needs?"

"Yes, Paul is a very good son". I didn't want to come right out and ask him what that meant. I suppose I was a little afraid of the answer. I had my suspicions, but it was not something I wanted to say out loud. Perhaps I would bring it up later.

"So what do you think now after two visits, mom?"

"They are really nice people, John, I can see why you like it here. Of course there seems to be a lot about the group that I don't know".

"Next visit you will learn a little more. It is a lot to take in all at once. But it is really a nice group of people. I think once you get to really know them; you will look forward to our time here. It's important to me, so I am glad you are giving it a chance."

I just smiled and looked out at the scenery going by. On the way back to San Francisco I reflected on my experience so far. My first Sugar Daddy experiences were pretty straightforward. They were just some older gentlemen with money to spend who wanted a companion to share for fun every now and then. That seemed to be what most of the sugar daddy's that contacted me wanted. 

I had received many offers with various role-play scenarios. However, John's offer was a little outside the norm. I took it because I figured, 'what the heck'- a little harmless role-play was no big deal. I figured maybe he had some mommy issues and wanted a little freaky sex. I could deal with that. I even understood that he wanted the role-play to continue 24/7 and abided by this for phone calls and chat sessions in between visits. But this church thing had me a little on edge.

"You are being quiet mom, what's on your mind?"

"Oh nothing", I lied. "What do you have in mind for the rest of the day?"

"I figured we would go back to the condo, makes some drinks, and relax. Tomorrow we have a busy day of shopping."

"Sounds great, just what I need".

Back at the condo, we mixed some drinks and sat out on the balcony overlooking the city street below. I was thinking I could fall in love with my city home. I am really a northern city girl kind of stuck in the country of the Deep South. Coming to San Francisco each month for a few days was something that I really started looking forward to. Rural Georgia was something neither hubby nor I enjoyed. We are from the city and would love to move back to the city. Right now hubby's work kept him in Georgia, but I bet he would love it here.

I pushed John a little more on the church. "So how long have you known Paul?", I asked.

"I guess almost a year now", he offered. "Paul introduced me to the church. But before that he was a client of my firm. We kind of hit it off. Anyway I met his mom at his house- she lives with him. Sandy is very nice as well and the two of them are very close."

"I gathered that. So does Paul have a girlfriend...I assume he is straight."

John chuckled. "Yes mom, Paul is straight and no he does not have a girlfriend. Like me I guess he is too much of a workaholic to date anyone seriously. Besides he spends a lot of his off time with his mom. Occasionally he and I will grab a beer or something, but I think he is happy right now the way things are."

"What about you, no lady in your life?" I probed a bit.

He chuckled, "No, just you mom."

We finished our first drinks as the cool evening air put a chill on my enjoyment of relaxing to the view of the city lights. John must have read my mind as he suggested we take it inside. I took a sit on the sofa as John poured the remainder of the drink left in the blender. He handed me one of the glasses and sat next to me on the couch.

"Would you like a foot rub mom?"

"Oh yes, any time." I quickly responded. "You know I love foot rubs."

John grabbed a container of lotion, slipped off one of my house shoes, and began warming up the lotion in his hands. As he started applying the lotion to my tired feet, he continued our conversation.

"Mom, I can tell you are worried about the relationship between Paul and his mom Sandy. The important thing to understand is that he is now taking care of her. He has the means of providing things for her that she never had while she was sacrificing to get him a good education and a good start to his life. Like many of the parents of the group, she resisted moving in with him and leaving behind her life back home. But soon she realized how nice it was to have someone who not only could take care of her, but also provide her with relative luxury. In many ways the roles are much reversed now. Paul makes all the important decisions for her, so that she doesn't have to concern herself with trivial matters.

"Is this what you want of me son? Do you want to take care of me and make decisions for me? You know I am a pretty independent woman...and I have your step dad as well. So I am not alone."

"I realize all that mom, you don't have to worry. But perhaps while you are visiting me, you could let go a bit and let me pamper you. Let me take care of all the important matters."

I looked at him and smiled. I was thinking of more than pampering, but I replied, "I think I would like to be pampered once in a while."

"Good then, that is settled." He declared. "You will see that you will enjoy this. Tomorrow we will go shopping so that I can pick out some things for you".

"You are going to pick out my clothes?" I interrupted.

"Yes of course. Now lay back and let me massage those calves".




Middle Age Sugar Baby Ch. 02



I enjoyed the firmness of John's hands as be massaged my feet and calves. He was talented and the relaxation was putting me to sleep. Somewhere, I dozed off.

In the morning I woke to the sunlight glimmering through my window. I was naked in my bed, which was not unusual. I always slept in the nude. However I didn't remember getting undressed the night before. The last thing I remember was dozing off on the couch last night. But there was no time to ponder this mystery; I had to get up to pee. Quickly I got out of bed, grabbed my bathrobe and proceeded to my private bath. I didn't hear John up yet, so I decided to go ahead and jump in the shower.

By the time I showered and dried my hair, John was up in the kitchen making breakfast. I put on my bathrobe and joined him. John was a good cook and enjoyed making breakfast. If we ate at home, I generally made lunch or dinner. As I came out to the kitchen John handed me a cup of coffee. It was a luxury to have a cup of coffee waiting for me when I got up. Shirtless, John was wearing just a pair of sweats and slippers. He was a well-chiseled young man, with just a hint of a six-pack. His hair was wet, and he smelled a bit of Irish Spring, so I assumed he just got out of the shower.

Breaking the silence, John asked, "How did you sleep mom?"

"Oh... great John...I don't even remember going to bed last night."

"Well, you fell asleep pretty early while I was giving you a foot massage. Anyway, sit down for breakfast. Then we will get on our way shopping. I already called Brian and caught him up on your visit. I told him we will be gone all day shopping. He said everything was fine at home."

"You called your step dad?" I asked, rather surprised.

"Yes, I let him know you fell asleep early before you could call him, so I wanted to check in before we hit the road. We talked a little bit. He said he went out to Delaney's with Frank last night. I told him you were doing fine. Anyway, sit down and eat, and I will go lay out your clothes."

He was out of the kitchen before I could protest. 

Forty minutes later we were on the road. John explained that we would be spending some time at Great Mall in Milpitas near San Jose. That sounded fine with me- I loved shopping malls. I decided against asking John about how I got to bed, or how I got undressed. Maybe I got ready for bed by myself and don't remember. Or perhaps John took me to bed and undressed me. Either way the topic would be embarrassing. 

My son and I spent a lovely Monday shopping. He selected several dresses skirts, tops, and shoes. I was not used to someone selecting my clothes. I never even let hubby pick my clothes, preferring instead to do my own shopping- even for birthdays or holidays. John insisted though and fortunately he had good taste. He selected some conservative outfits I could wear to church as well as some tastefully suggestive outfits I could wear at nightclubs. I am sure we got some strange looks from others as I modeled them for his approval, but I didn't really care. 

It was early evening when we got home and I was quite tired from shopping all day.

John carried the bags in the condo and let us in. John bought more than I realized. I gave him a great big hug and thanked him for all my presents. He just smiled and said, "I bet you could use a nice bath. Why don't you go relax in the tub a bit and I will make us something to drink."?

A bath sounded great. I went to my bathroom and started running the water. I loved this bathroom and been admiring the big tub since the first time I saw it. It was standing one level from the floor with a big bay window along the back wall. The other three sides were open to the rest of the bathroom. I found some bubble bath, poured it in and went back to the bedroom to undress. Taking off my jewelry, I placed each item carefully on the dresser. I admired them a bit before removing my clothing and placing them on the bed.

I walked naked back to the bathroom and glanced over at the full-length mirror before approaching the tub. 'I wish I could lose a couple pounds around my hips and tummy', I thought. My boobs had dropped a bit with age, but still looked darn good for 52. Satisfied, I grabbed my book, walked over to the tub, tested the water and lowered my self in. 

Moments later I heard John enter my bedroom. There was no door between the bedroom and the bath area, just an open doorway. So John appeared in bathroom without further warning. He was wearing his usual sweatpants, no shirt, and no shoes. "I thought you would like your drink in here mom", he offered.

"Uhmm, thank-you?" Without thinking, I raised my arms to cover my exposed breasts. I was not really sure how to respond to him seeing me naked, but I was genuinely surprised to have him walk in on me.

He came over and sat on the side of the tub. 

Glancing down I realized my partially inclined position was not the most flattering. I felt as thought my boobs lay low against the top of my belly and was a little self-conscious for a moment. I tried to sit up a little straighter. John didn't give any indication that he noticed. 

"How is your bath mom?" He asked, handing me my glass.

"Just wonderful....umm, Thank-you." I took the wine and gave up the modest attempt at covering my nudity. 

John must have noticed, as he offered, "Mom, it's OK, it's not like I haven't seen you naked before."

"No?" I questioned.

"Just last night I undressed you for bed, you didn't act modest then... Why don't you just slide back down a bit and let me wash you," he responded. Then, without waiting for a reply, he grabbed the bath sponge and ran it along my shoulders."

"John, are you sure you should be doing that", I asked, not really sure what to say.

"Why not, just sit back and relax"

'Well, there was one mystery solved', I thought. John had apparently taken me to bed and undressed me last night. I must have been really out of it. The thought was unsettling.

As I sat there thinking about it, I was only vaguely aware of John running the sponge up and down my back. I have to admit I was enjoying it. When he returned to my shoulders I just lay back against the end of the tub and enjoyed the gentle massage my body was experiencing. He ran the sponge down my chest, over and around each of my boobs- lifting each one slightly to reach underneath. Then he drew circles around my belly before dropping down between my legs. I spread them slightly to provide better access. As he washed my laser smooth pussy he just stared expressionless into my eyes. He grabbed one hand at a time to lift each arm, then ran the sponge up and down by arm and around each armpit. Similarly he cleaned one leg at a time, stroking my pussy just momentarily after each leg. I closed my eyes as he passed over the most sensitive areas, not wanting to betray my excitement. 

Despite spending several nights with John between this visit and the last one, this was the first erotic moment I had with him. At least it was erotic for me. If John was equally excited, he didn't show it. I just let my body relax as he made his way over every inch of it. I was laying back and soaking it all in when I heard him turn the drain to release the water. I looked up to see him holding a towel with one had and reaching for my arm with the other. He helped me to my feet and I stood naked before him. He helped me out of the tub and began to dry me off.

"Let's get some lotion on you" he announced, breaking the silence. John then began applying the body lotion, first on my arms and back, then over my shoulders, before working his way around front to my chest. I enjoyed his soft bare hands gently rubbing the lotion over my breasts, one at a time. Too soon he moved on and continued down, my belly and then down one leg at a time. He walked me to the bed and motioned for me to lie on my belly. Here I got the most amazing back, leg and foot massage. When he was done, he bent over and kissed me on the cheek and said good night before leaving the room.

I lay on the bed relaxing for a moment before rolling over. Now on my back I caressed both breasts simultaneously with my hands. Closing my eyes I encircled each areola with my index finger. I had large pink areola that blended gently to my light skin. I loved to have fingers run very lightly over them. My nipples were very large and protruding. I loved to have then sucked, but would have to settle for pinching them with my finger and thumb, rubbing back and forth for greater stimulation. I reach my left hand between my thighs, raising and spreading my knees to provide better access to my pussy. I played with my labia using my index and middle finger for a few moments before moving to my clit. My juices were already flowing when I began pressing on my clit with my middle finger. 

My first orgasm was beginning to develop as I continued circling my clit with my finger. I arched my head back, trying to enjoy myself without being too loud. My thoughts were of John and I imagined him pleasuring me as I began to orgasm. I needed to be filled, but I would have to settle for being teased. John was good at teasing me, but I needed more than that. I played more vigorously, arching my back in response to the rushing feeling pulsing through me. It was over too soon, but I settled down, lying there with my fingers in my wet pussy for several minutes. I looked over at the open door and noticed a light in the distance- but there was no indication that John was still up.

I had only one day remaining before I had to return to Georgia and I remained very conflicted. I liked John, he seemed like a nice young man. He was also great eye candy, and the thought of a sexual adventure with him was stimulating. But he seemed to tease a lot around the edges, leaving my sexually frustrated. I had to remind myself that he was in control and this was his fantasy, not mine.

John again had my clothes laid out for me. Though it was a little cool this time of year in the bay, John selected a black sleeveless silk dress with a high-low hem. The selection coupled with my high heels highlighted my long legs and looked rather elegant. He laid out a bra, but no panties. I assumed it was not an oversight and went along without. John was dressed in business casual.

This was my first day of seeing the city. I always wanted to ride the cable cars and thoroughly enjoyed our ride down to Fisherman's Wharf. 

I am not one for seafood, so we made our way around the bakeries instead; sampling some of my favorites and a few items I had never tried before. But the highlight of my day was our visit to the Aquarium of the Bay. There will be many things for me to see and do in future visits, but I thoroughly enjoyed the hours we spent in the aquarium and John was a doll to be so patient with me.

Throughout the day, much like yesterday, we walked arm in arm. John always made a point of referring to me as mom, so as to leave no doubt in anyone's mind that he was out with his mother. It was a great day overall, but I was still anxious to make it back to the condo and spend some alone time with John. In two visits with John, we had spent six nights together. However, with the exception of some painful teasing last night, he did not make any sexual advances on me. I knew I wanted him to. 

We returned to the condo just before 7pm. It was hard to believe that my visit was near its end. As anxious as I was to see hubby again, I also wanted desperately to see where John was taking our relationship.

"John, are straight?" I asked, hoping to steer the conversation in the right direction.

John chuckled a bit, "Yes mom, why do you ask such a thing?"

"Well, it is OK if you are", I asked, pausing to see what reaction I would get. He moved over to the couch where I was sitting and sat down beside me. Seeing no intention on his part to respond, I continued: "I guess because you don't seem to have had any relationships since you have been here in San Francisco...at least you haven't talked about any." 

"Oh, I guess I have had a few, nothing long-term really. Most of my friendships are those associated with either the firm, or with the church," he offered.

"But nothing romantic really", I countered.

"Mom, where are you going with this? What are you concerned about?"

God, he was being terribly evasive. I was becoming very confused as to what he really wanted with our relationship...or agreement. Determined to stay in the 'role' and still find out where he was going, I probed some more. "John, do think I am attractive", I inquired.

"Yes, mom, you are a very beautiful lady. That is one of the reasons I enjoy buying nice things for you to wear...that, and because you appreciate them".

"Yes, John, I really do appreciate those things...it's just that...well... You have undressed me...and last night, you bathed me and massaged me- very erotically. But you have shown no erotic interest in me."

"John stood up quickly, looking genuinely surprised. Of course not mom, you're my mother after all, why would I...I mean why would you want me to."

Wow, I did not expect this. Thinking out of character, I considered for a moment how I could possibly have misread his intention. In the Sugar Daddy agreement, he specifically indicated that I should be prepared for a sexual component to our relationship. Perhaps this was part of the role-play. Did he want to stretch this out even further, claiming some sort of righteous indignation, only to be slowly drawn into some sort of incestuous relationship later? I was truly confused...and frustrated- sexually frustrated actually. But instead of speaking, I sat there staring at him waiting for him to continue.

"Mom, I actually understand what is going on here. You are a wonderful person, and I love you. You have taken care of me and I truly appreciate that. But you have an obsession with sex." 

He paused to see my reaction, but getting none he continued. "Look, I know more than you think I know about your lifestyle. Brian and I have talked about this. You are a very sexual person and so is he. Mom, there is really nothing wrong with that. But it is important to channel that sexuality in the right direction."

"What exactly have you and Brian talked about?" I inquired, truly curious now.

Ignoring my question, he continued. Mom, the people that you met at church are not unlike you and Brian...or at least they were at one time. Sandy would have indiscriminate sex with complete strangers all the time. However her erotic needs are now met within the context of healthy loving relationships. You will find out about these things in future visits. Perhaps Brian will join us at some point as well, he expressed a willingness to do so. 

"Is that what this 'church' is all about?" I interrupted. I actually had dozens of questions, but I was trying to process what I was hearing.

"It is more complicated than that mom," he continued. "But yes, the parents you saw there have similar sex drives as you and Brian do. The children...my generation...have a much more balanced outlook. But more to the point, we help our parents channel their desires in a more suitable way. You will come to understand more as you spend more time here. Listen, we have had a wonderful time together, and I know you have enjoyed your visit. This is a lot to take in, but I promise you, you have some amazing, safe experiences in front of you. You have to trust me and let me direct you on this journey."

I looked at John, rather surprised by this turn of events. 'God, what a body that boy has', I thought. Truthfully, I just wanted him to fuck me. That did not seem likely, certainly not on this trip, and perhaps never. Now I was not really sure where this adventure was going, but two things I realized. First, Brian and I were going to fuck like crazy when I got back home. And Second, I was going to come back and see where this crazy adventure was going to take me (and perhaps Brian as well).