Middle Age Sugar Baby…The beginning

My name is Kathy. This series of stories focuses on my most recent experience in pushing the erotic envelope. 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.

I am now fifty-five and my 5'6", 148-pound body is much younger looking than my age would suggest. I have perhaps a pound or two I would like to rid myself of, but I still look and I feel great. I think my legs are my best feature, but most men seem to notice by boobs first. At 36DD and very real, my chest draws attention. I have worn my hair blond and shoulder length for most of my life. My Husband likes it that way.

Oh yes, I am married. Brian and I have been together since childhood. It is probably a bit cliché to say that we are soul mates, but truthfully this is the way we feel about our relationship. We both love exploring new adventures and pushing things as far as we can. He is the only person with whom I could share any fantasy and thought, without the concern for being judged. We love to share those thoughts and find a way to make them a reality.

From childhood friendship through 35 years of marriage, we have had some truly amazing experiences. We are very sexual people who happen to believe sexual monogamy is unnatural. And so we have been a lifestyle couple, in an open relationship for most of our lives. Of course the problem with that is, if it is a problem, is that one keeps 'raising the bar'. This series of stories focuses on the most recent adventures I experienced when I decided to explore the world of being a sugar baby.

Now most sugar babies are young women looking for some cash and adventure in a world they might otherwise never have the opportunity to experience. For them the sugar daddy is simply a means to an end. But I was fifty-one when I decided to explore this new world. At fifty-one I was still pretty hot. Besides in the lifestyle much younger men and woman, who are interested in older, in shape couples, often approach us. So it was not such a stretch to believe there would be some young sugar daddies seeking much older women.

We started this project together; creating a profile on a couple of the more prominent sites that specialized in Sugar Daddy relationships. My husband did most of the work in creating the profile. It was kind of exciting to see how far he would go advertising the services of his wife. Brian is a quiet kind of guy. But that reticent personality masks a very sexually adventurous character.

We started getting inquiries immediately. We already had a great deal of experience on lifestyle sites, so we were able to sort through the fakes and flacks pretty quickly.

There were several candidates that interested me; however it was also important for Brian to feel comfortable with our choice. He gravitated to the older gentleman that were married. I never thought John was insecure, but perhaps the fact that these were all wealthy men intimidated him just a little.

I looked for men that had at least $1 million validated net worth and could provide a minimum of $1000 allowance per month. I am sure the younger ladies could fetch much higher sums, but I had no idea how high a gentleman would pay for the companionship of a fifty something lady. I was pleasantly surprised.

I also had to see myself being able to have sex with the guy. The candidates were very specific in inquiring what I would and would not do. I consider myself pretty open sexually. I have never been into anal, but beyond that I have few sexual restrictions. Most of the sugar daddies had a specific 'role' I was to play and I was good with that.

For several weeks, I just exchanged e-mails and chat sessions with some of the more promising candidates. However, I found that most of these men wanted to move things right along. Apparently they many had experiences with woman who backed down or otherwise did not follow-through. I had no such compunction. Once I made up my mind, I made it happen. This was not a social site for these gentlemen: It was a business transaction. So I learned to be just as straightforward as the Sugar Daddies were.

Some of the men turned me on more than others. But the purpose was not just sexual adventure. I wanted this to be lucrative and safe. I had offers to fly overseas. I had offers for long-term live-in situations. You name it; there were all kinds of options. I was having fun, but I knew I needed to get down to business and make a selection for my first candidate- one that would be exciting for me and comfortable for hubby.

So after some discussion we selected a candidate for my first experience. His name was Frank. He was a 68 year-old businessman from Miami Florida. At 5-10, 220 pounds he was perhaps a little heavy but carried it well. I guessed he probably weighed a little more than his profile indicated. He was bald, which I do not mind at all. I wouldn't say that I was sexually attracted to him, but I enjoyed our conversations and thought we would get along well. The two of us exchanged a few e-mails and had several conversations on the phone.

Frank loved Latin music and claimed to be a great dancer- something that I really looked forward to. He lived in Miami, but often traveled to Atlanta and Charlotte for business. I was to be his travel companion for these occasions.

Frank knew that I was married as well, and he was OK with that. I offered to let him chat with my husband to demonstrate that Brian was fine with this; however Frank declined, saying it was unnecessary.

Frank also indicated that he could not use a condom. This practice made me uncomfortable. However, Frank provided documentation that he was clean and asked that I do the same. Reluctantly I agreed to this one last provision.

Once the decision was made we agreed to our first meeting, which was to take place in Charlotte. It would be a short visit, just one evening to make sure we were both comfortable with it.

Now that the reality of this was setting in, my husband was getting a little uncomfortable. The sex was no problem; Brian was a little excited about that. But since I would be traveling alone, and we had not previously met this guy, he was concerned for my safety. I have always been able to take care of myself, but there are a lot of kooks out there.

It took several days, but eventually hubby seemed to be settling in fine with the decision. Perhaps he was even a little excited.

Frank provided us with the details of our first trip. The date was non-negotiable and I soon learned that I would need to be flexible to the schedule of my sugar daddies. Frank offered to fly me to Charlotte, though I felt more comfortable driving there. The security of having my own care was worth the two-hour drive. I also insisted on my own room at the hotel. To my relief Frank agreed to both.

A few weeks later I arrived that the Omni Charlotte Hotel in downtown Charlotte. I spotted Frank waiting for me in the lobby. There was no doubt is was him and I just walked up to him, gave him a hug and said, 'Hi Frank'.

As he hugged me, Frank turned his head to give me a little peck on the cheek. He seemed like the nice gentleman I expected. "Its good to finally meet you Kathy, how was your trip."

"It is a long drive, but I am glad to be here." Frank was as easy to talk to in person as he had been on the phone. He took care of my check-in and bags and we sat down for a drink in the hotel lounge. I was anxious to get to my room and settle in, but he seemed to want to spend some time chatting so I went with it. I had no experience with this lifestyle so I was not sure how much say I had in our activities. I decided to just let him set the direction and tone of our adventure.

Frank interrupted my thought. "I have a present for you Kathy".

"Wow, I love presents...and surprises". I was not playing, I really did, but what girl wouldn't. I opened the gift-wrapped package and looked inside...a beautiful pair of earrings. Not just earrings but yellow gold, round white & champagne diamond cocktail earrings. I loved them and silently wondered what I would be doing to earn them. But I thanked him and hugged him once again. This time I turned to him and kissed him on the lips. It was kind of a natural reaction, but he let it linger a little longer than I expected. As kisses went, it was nice. I was happy about that because I love kissing as a part of sex.

After our drinks we went up to our respective rooms to settle in and prepare for dinner. Laid out on my bed was a sexy black beaded evening dress in my size. The dress was a beautiful low-cut style in front with a long slit on one side. Fortunately I had brought the perfect 4-inch high heels for it. I quickly changed, fixed my hair and make-up and was ready to go.

I took the opportunity to first call hubby and let him know that I had arrived safe and sound. He had a lot of questions so I knew he was a little excited by it. He wanted to know all the details, but so far I had few to share. Frank looked like he might be older than 68 but I was not sure. He was very nice, though I wasn't really all that sexually attracted to him.

Frank and I looked stylish as we made our way out of the hotel. I felt wonderful and was looking forward to a nice evening with my new gentleman friend.

Dinner with Frank was very nice. We ate at the Fleming Steak House which is attached to the hotel through a glass covered walk way. It was probably not Frank's first choice, but of the choices he gave me, it was my choice. I made a mental note that if we continued this arrangement I would have to accept some of his taste in cuisine. I thanked him for the use of the dress, not sure if it was a gift or a loan.

"The dress is yours Kathy, you are a stunning lady who should have elegant things."

I honestly felt like this was over the top for a single night of companionship, but I was excited. Perhaps it was a down payment for futures services. Either way I felt sophisticated and trendy. I decided I would just enjoy the evening and see where it went.

After dinner we went to the Stage Door Theatre at the Blumenthal Arts Center to listen to Jazz. I would have preferred to go dancing, but it was actually quite nice. Throughout the evening Frank entertained me with his sense of humor. I was enjoying myself. He gradually became more affectionate now that we were in this relaxed setting. He sat beside me holding my hand ever since we arrived at the theatre. Eventually he had his arm around me and he would move his face closer to me as we talked.

I was curious about his personal life, as he had shared little of it to this point. I knew he was married and had two children, a son and a daughter. He had also told me that he loved his wife very much and never intends to leave her. Tonight he shared little more other than to tell me that she did not like to travel with him and was quite content to stay home and enjoy the social life there. He said they would engage in sex about once a month or so, but she had largely lost interest. Beyond those details he seemed pretty guarded about it.

Frank enjoyed traveling and having a companion who enjoyed many of his favorite activities was what made it special.

I could have ended the evening just going back to my room and reading a book, but I was pretty sure the evening would not play out that way. He was being very polite, but I know he wanted to kiss me, so I leaned in and gave him another opportunity to share a kiss. This time I kissed back with a little more enthusiasm.

We talked for a little while longer before deciding to leave the club.

"Shall we retire back to the hotel?" he asked.

"Sure" I responded. I wasn't certain if I was saying, 'sure you can fuck me' or not, but somehow I felt that way. If he didn't at this point I would not have been disappointed. We walked back to the hotel arm in arm. In the elevator he reached behind my neck to pull me in for another kiss. I felt his tongue explore mine as he pressed his lips against my mouth. I reached behind his back and pulled him in close to me as we enjoyed a few moments before the bell announced we had reached our floor.

"Give me a minute before you come to my room?" I asked invitingly.

He smiled and gave me another quick kiss. "OK, but stay in your beautiful dress until I get there." And with that he turned to go to his room next door.

As he turned away I entered my room and rolled my eyes to myself as I passed the mirror. There really was no turning back now. I wanted to talk to hubby, but there was no time for it. He must be wondering what was happening by now. I wasn't sure if he would go out with his friends or stay home, but hoped he was enjoying himself.

I went to the bathroom to pee before straightening the room. 'Hmmm, why did I bring my red baby doll lingerie and black stockings', I wondered. I still had a moment so I quickly sent my husband a text: "Back from dinner, think he is going to fuck me now" He just sent back a smiley face emoticon. I hoped that meant that he was excited by it all. I replied with the 'unsure' emoticon.

Moments later Frank knocked on my door. I swung the door open and just said, "Hi".

Frank had a bottle of white wine and a couple of glasses. I did not really want anything else to drink this late, but decided it couldn't hurt. He had left his jacket in the room and removed his tie. The top three buttons were unbuttoned exposing his white t-shirt underneath. Several gray chest hairs were protruding over the top of his t-shirt.

Frank walked over to the table and put down the bottle and glasses, then reached over and pulled me to him for another kiss. This time he put his hands to the side of my face and gently stroked my hair from behind my neck as he continued kissing me. His hands paused to admire the earrings. "They look gorgeous on you Kathy."

"Thank-you, again Frank, I love them". That was the truth. I wondered if his gesture was meant to mean something more. 'Was he trying to send a message?' That would be unnecessary; I had decided long ago that he could fuck me if he wanted to, so I hope he did not find that remark necessary to remind me of my obligation. No, I decided Frank was foo much of a gentleman for that.

Besides, I was getting the feeling he might even be a talented lover. Plus I liked him. I wondered what he would look like naked. Or perhaps I was concerned about that. I had seen some older people naked at nudist resorts and it was not always pretty. At this point I had no idea what Frank looked like without clothes.

Frank sat down in one of the chairs at the table and reached for the bottle of wine. As he prepared to open it he asked me if I was still OK with this.

"Yes", I insisted, trying to sound just a little anxious.

He smiled and continued to pour us each a glass of wine. "Great, because, I really like you Kathy, you are an incredible woman". He then stood up and walked over to me and started kissing me again, this time reaching behind to undo the hook of my dress. After fumbling with it for a moment or two, he pulled the zipper down my back.

He placed his hands to the side of my face once more as he kissed me. Then he dropped his hands to my shoulders and slid my dress down to my hips. You have sensual shoulders Kathy; I have men admiring them all night. He started kissing my shoulders and then knelt in front of me so he could continue pulling my dress down to my ankles. I lifted one foot at a time as he passed my dress over my high heals. As he looked up at me I stood before him in only bra, panties and high heels as he stood up to continue kissing me.

Frank turned to the table and handed me a glass of wine and we each took a seat at the foot of the bed. "You are an amazingly beautiful woman Kathy. I hope this is the first of many experiences for us".

I touched my glass to his and said "to the first of many". Not sure how that came off, but he smiled as he took his sip of wine.

He then knelt down again to remove my shoes, caressing my calves with one hand and pulling the shoe off with the other. "Wow, you have amazing legs", he said admiringly.

"Comes from dancing, afraid my feet show some wear and tear from dancing though".

"You have beautiful feet too he said, would you like a foot rub?"

"I love foot rubs!"

He gave me the most amazing foot rub: Rubbing lotion in my feet and massaging my toes, balls, arches, and heals with his talented fingers. As he finished with my feet he worked his way up my legs kissed me over my panties, and up to my belly. His fingers gently caressing each part of my body as we worked his way up and then back down again.

Suddenly he slid my panties down and over my feet.

"Why don't you get more comfortable?" I said.

With that he stood up and began to undress himself. As he took off each article of clothing, he carefully laid it over the chair. When he removed his t-shirt, I could see that both his chest and back were pretty well covered with gray hair. I didn't mind chest hair, but am not fan of back hair. He then removed his shoes, and socks and dropped his pants exposing his 'whitie tighties'. There was not too much of a bulge yet, so I was not sure if he was still soft, or if he was small.

He came back on the bed to reach around and unclasp by bra. Now I was totally naked and he enjoyed my boobs for a while, first with his hands and then with his mouth. He didn't talk much but he was enjoying my naked body, caressing me with his hands, kissing and licking with his lips and tongue. He kept this up for some time before probing my labia and clit with his fingers. Pleased that I was wet, his kissing was becoming more powerfully than before. Then he came down to explore me with his tongue. He was very talented and I enjoyed his oral skill for several minutes before stopping him.

"Let's get rid of these", I said, pulling down his underwear. He offered no resistance.

He was semi hard, maybe three inches, but very thick. He didn't shave or trim down there, which was a little bit of a turn-off for me. Still, I went down on him, pushing his pubic hair away from his shaft with one hand and caressing him with the finger and thumb of the other. I loved to suck on a cock while it was still soft and I clasped my lips over the thick 'helmet' of his penis. I swirled my tongue around the tip of his penis. I could smell a faint odor of pre-cum and he started to get hard. I kept working his cock as it gradually grew to five inches or so. I was not sure if it got any bigger, but it was very straight thick and hard.

His ball sack was large and hung low; but he didn't seem to particularly enjoy me playing with it, so I was glad to leave it alone. I didn't like hair down there either. I wasn't sure how long he would stay hard, but he kept his hand on the top of my head, so I guess he wanted me to keep going. I moved up and down his shaft, easily able to take it all the way to his base.

I didn't want him to cum in my mouth, so I pulled away and said: "Come here. I want you inside me". I tried to climb up and position myself cowgirl style. This proved fruitless as his penis kept slipping out. I turned around to reverse cowgirl, but he was getting soft, so I decided to give up being on top.

He seemed content to let me decide positions, so I rolled over on my back in missionary position. He was much more comfortable this way. He pushed his penis in very slightly and began caressing up and down along my labia. Finally I was able to get wet again and his penis was hard enough to enter me. This was obviously his comfort zone.

I get very loud during sex, and even though I had told him this before, I think it surprised him. It also probably made him feel confident as he pushed himself inside me and started pumping. Now his length was not a problem, his thick cock felt snug as he stroked up and down. I reached my legs as high as I could so that I could get him deeper inside. He was very quiet, but seemed to be enjoying himself.