One of the biggest problems with me and my older lover isn’t where to get intimate or what to try—and, so far, we have been lucky to not have to worry about that “blue pill.” Our biggest problem has been our difference in sex drive. With my man’s packed work schedule, and with me juggling work and motherhood, when we are together, I crave sex and intimacy. I would want to make love multiple times a week, whereas he is perfectly fine with doing it once a month. He is completely OK if we are not intimate on a regular basis.…
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Women and men of all ages, shapes, and sizes love being in a relationship. But what constitutes a good relationship? For some people, a friends-with-benefits relationship is all they need—they’re perfectly OK with having someone to just hang out with, with the perks of being able to mess around with no strings attached.
Everyone has a different version of what an actual relationship means, and no one needs to make any compromises for anyone else. That’s why a sugar daddy relationship was what worked best for me at the time.…
My older man, Mr. Brown, had just gotten drunk and spent the evening with his partner and two escorts that his partner had brought along. He knew I was upset, but he had too much to drink, so I didn’t make a scene. Instead, I helped him get back to the hotel so that he could go to bed.
After I dropped Mr. Brown off, I just wanted to grab a bite to eat and spend some time with my daughters. I also wanted to talk to them about how they felt about my relationship with Mr. Brown, who also happened to be my boss.…
On the trip to Canada, the Stetson man—my older, married boyfriend—had brought photo albums and other personal artifacts because he wanted to share his life with me. I saw pictures of his mansion, his prize animals, his businesses, and much more—including his family. He had shared these pictures with my friend and me, and at the time I hadn’t said much. The truth was that looking at those pictures made me feel sort of like a voyeur, which was a weird perspective of his life. As well, judging from his photos, his life had nothing to do with me.…
The Christmas holidays were fast approaching, and they were going to mark the first holiday season since my older, wealthy boyfriend’s wife had moved out of their mansion. The Stetson man was still technically married, but I wanted to celebrate this holiday as a couple. I persuaded him to allow me to throw a Christmas party at his home.
This party was the first time I would be completely entrusted with something of this nature in his territory. He had a staff that normally handled these kinds of arrangements.…
I ignored my cell phone ringing two or three times. I knew it was my lover and my boss, Mr. Brown, calling to check up on me and make sure I had made it home safely and that the girls were happy to be home. Unfortunately, I couldn’t answer it because I was standing face-to-face with my ex-husband and he was at my new home, that I was just gifted from my boss.
My ex had a look of confusion on his face and immediately started with the questions. Where did I get the money for a house payment? Who really paid for my vacation with the girls?…
Now would be the best time to be honest about the role that sex plays in my relationship with an older man, Patrick. Its frequency, importance, and power over how we grew as a couple had a lot to do with him, at least in the beginning.
Patrick was a man who was obsessed with being with me and, because I had never been in that kind of a relationship before, I was aghast and amazed by his attraction to me. What I thought might be a very affectionate but occasional affair grew by leaps and bounds. I had trouble being responsive to all of Patrick’s demands and, at times, I would try to be unavailable to him, just so that I could catch my breath—and some sleep.…
After I decided to break up with my older lover, Patrick, over the phone, he immediately called one of my best girlfriends for sympathy. “Not a big deal,” you say? It wouldn’t have been such a big deal, except he then told her in very vivid terms how much he liked my body and why. And I’m not talking just breasts either—he went into intricate detail about exactly which parts of my body he adored when we had sex.
Needless to say, my dear friend Carolyn was, of course, horrified, disgusted even.…
I had done my best to put the haircut incident out of my mind, but it was clear that the dynamics of my relationship with my older lover, the Stetson man, had changed drastically—after all, he cheated on me with the lady who cuts his hair. The Stetson man was no longer possessive or jealous the way he had been before. I was not being invited to as many events as I had once been. Often, I didn’t know about something until he was preparing to leave the house. I started spending more nights than usual alone at my own house.…
My girlfriend, Tori, knew everything about me, including what happened the night I met the Greek God at the auction. I have always said that Tori and I have to stay best friends, no matter what—we have too much on each other to be enemies. She knows me better than anyone else, which is why when she suggested that I call the Greek God, I decided to listen to her.
After a long conversation with Tori, I decided to text the Greek God instead of calling him. This sparked a texting conversation that lasted through the evening.…
They say the easiest way to connect with someone is by making eye contact with them. Yet a lot of people don’t realize how much of an effect simple body language cues like this can have on forming relationships. In fact, eye contact is so powerful that it can actually significantly improve your May-December dating life, and there’s proof!
Looking into someone’s eyes can tell you a lot about their feelings, which can come in very handy for the purpose of May-December dating. The idea of mutual gaze (when you look interrupted into each other’s eyes) is one that’s been studied a lot.…
My friend, Tori, and I boarded the jet with the Greek God, his ball players, and their girlfriends. A few bottles of champagne were popped, toasts were made for good luck, and congratulations were shared for some of the players’ birthdays. I didn’t ask any questions about where we were going. I decided earlier that I was going to let the universe bring me a great time on this trip—and so far, it was working.
The Greek God was a complete gentleman and kept asking if I was having a good time.…
I had just spent the most incredible night partying with my friend Tori, the Greek God, and all of his ball player friends—we had dinner, went dancing, and then took his private jet to a casino in the Caribbean.
The sun was up before we even left the Caribbean, and it was nearly noon by the time we landed in the Greek God’s city. He drove us back to our hotel—we all were tired and made small talk during the drive. He pulled into the long driveway that leads to the hotel door. He drove past valet and parked himself so that he could open our doors for us.…
Although my relationship with my older man wasn’t classified as “cheating” or adulterous, since we were both technically single, there was still a tinge of illicitness to it. Patrick was still close to his ex-wife with whom he had had three children. In fact, they worked together at the company he founded. And she was not just some secretary or administrative assistant; she was the chief of operations, which means she was responsible for managing the staff and making day-to-day administrative and financial decisions.…
I had been home for a few days since my first travel date with the Greek God, although I’m not even sure you can call it a first date. I was constantly checking my e-mail for word from the Stetson man. I was watching my phone pretty much all day. I was a complete nervous wreck. I could not understand how the Stetson man could just go floating down the Rhine River without me without even checking in once. If I had gone off for several weeks with no way to contact him, well I can’t imagine the hell I would pay.…
Patrick’s ex-wife’s name was Deborah. She didn’t get up from her chair behind the teak desk to meet me, but I offered my hand and, somewhat reluctantly, she took it. She was a small, full-figured woman who was obviously quite a few years older than I was. As most women do, she sized me up as quickly as I did her. I couldn’t help but notice the resentful look on her face.
She was wearing a Chanel suit, dark stockings, and pumps. I was wearing a grey Donna Karan suit, dark stockings, and pumps.…
The Stetson man was still in Europe, and I still had no contact with him. I convinced myself that he was showing the barber a great time—after all, he did cheat on me with her. The Greek God kept phoning. I didn’t answer—all I could hear in the back of my mind was Smack telling me that he had multiple mistresses and that I was just another one of them. So, I decided that if I was going to keep this man’s attention, I had to make him think he was going to have to work for my attention.
The night I spent dancing and gambling with the Greek God made me realize that the universe might be providing me with a sugar daddy replacement for the Stetson man.…
My older man, Patrick, had one son, Michael, who, at 22, was the youngest of his three kids. After the positive experience of meeting his oldest daughter, Juliet, I actually looked forward to meeting Michael—I got along really well with Juliet, so I was sure I’d do just as well with Michael. Besides, I always got along better with men than women anyway, and I also thought that at that age, he would be pretty non-judgmental.
Michael worked at Patrick’s family business and saw his dad pretty much every day.…
It was several months after I met my older man, Patrick’s, son and younger daughter that I had the chance to meet the last of Patrick’s three children—his other daughter, Isabel. She loved horses, spent daddy’s money liberally, and did some kind of work for the family business, although, from what I could tell, she was not there much. She did have a man in her life, and it looked like it was headed for the altar, but no dates had been sent.
I remembered Patrick telling me she was very much like her mother, which made me think she was not going to be very open and accepting of me, the way her sister Juliet had been.…
Saturday morning finally arrived—I was going to meet the Greek God in his city again for another date. I had another to-do list that I checked off in pink highlighter to make sure I didn’t miss anything. The page was full of pink.
I drove to the airport with a nervous feeling in the pit of my stomach. It had been far too long since I had any contact with the Stetson man. I was sad about where our relationship had ended up. I had no idea what he was doing or thinking, or who he was even with for that matter.…