Being in the same phase of life has its advantages when it comes to relationships.
I wish Alfred was my age because we would have the luxury of growing old together and sharing life’s experiences. We’d both be energetic lovers, without complaining over an achy knee, a tired back, and feeling sleepy at noon. We’d have an economical advantage by having two incomes growing the household instead of just one.

If I was 70 years old, I may feel content living a retired lifestyle and taking a nap during the day. I wouldn’t have goals and dreams and plans of going to graduate school. I may be happy making dinner and doing light housework. I would have a small dog on my lap and eat candy while I had a fish in the smoker. I could go to the local pub on a Wednesday at 2:00 p.m. for some socializing and a drink before others got off work and made the place crowded. My professional goals would be accomplished. My sons would be raised and have families of their own. I could go fishing and camping and spend a few days on the river during the week without having to get approval from the boss. I could wake up naturally instead of to the scream of an alarm. Alfred would be happy to have someone around the house taking care of him and just being a full-time companion. I’m certain our dynamics would be much different.

If Alfred was 45 years old, he would be in the prime of his career and ready to move up. He would be sending his daughter to college. His dark hair would have some flecks of silver on the edges instead of being entirely white. He wouldn’t need me to read the menu at the café on the days he forgot his reading glasses. He would have a strong back to cut wood for the bonfire and drive a taller pickup truck that he could step up into. He would have his own motorcycle to drive on our Saturday afternoon cruise. He’d be a valuable member of the household—fixing the family vehicle, walking the dog, taking out the trash, mowing the lawn, fixing the TV, bringing in an income and paying the bills.

I wish I was 70 years old, because then I would understand him and his life better. I can’t look back and remember what it was like to be 70 years old. Alfred understands and remembers what it was like to be 45 years old, though.

Alfred gets his excitement and high-speed action when we get together. For me, the weekends together are a time to slow down, relax, take a nap, cut some wood, have a drink over the bonfire, and enjoy a slow pace. Even when we are together, our perspectives of our time together are much different, yet we both find a very peaceful and enlightening experience with each other.

If you are content living a day at a time and not having long-term plans for a future in your May-December relationship, it works. If you appreciate each other in the moment, it works. If you have a spontaneous nature, it works. If you have peace and happiness living in the moment, it works. But if you have long-term goals for a partnership for your future, and want a similar lifestyle, the obstacles can be enormous.

I have decided to be content with the age difference and live life a day at a time. I appreciate the time shared together. Love, trust, friendship, and companionship do not come easy, and when they did, I grabbed them. If my level of contentment ever changes, it will certainly change the path of our May-December relationship. That’s how it is. Nobody is promised a tomorrow, and who knows, perhaps Alfred, at 25 years my senior, will outlive me.

The post Proof That Age Is Really Just a Number When You Love the Man You’re With appeared first on Sugar Daddy Online Dating by EarnTheNecklace.com.

Let’s talk about my sex life with my older man. Sam was 46 and I was 24. By the time we got together, he had years of sexual experience “under his belt,” with his marriage, with extramarital affairs, and with using his creative mind and spirit.

My young husband and I had never ventured outside of traditional intercourse. We were both shy and inexperienced, and I guess we just didn’t desire to venture into those waters. So imagine my first experience of it with Sam. Wow! Where had THIS been all my life? Sam knew I was new to this, so he enjoyed doing it to me and experiencing my reactions. This was such a major part of our May-December relationship—and so exciting for me—that I childishly kept a calendar, noting when it happened. Years later, I looked back on that calendar and was reminded that some weeks it was a daily occurrence. It was daily if he was not with his 11-year-old daughter, with whom I had to compete for his time.

Sam introduced me to a whole new world in the bedroom. There were dildos, feather ticklers, massage oils, Ben Wa balls, and even “dirty” movies. There was even one night he surprised me by dressing up in skimpy underwear and a baseball cap, and dancing sensually to music in his living room—I was speechless. Sam had the maturity and self-confidence to not feel “silly,” and wanted to try everything with me. His adventuresome approach to lovemaking helped me to learn and grow in my own sexuality, and I learned that sex could be so much more fun and exciting than what I was experiencing with my husband.

Naturally, we had intercourse, too, and his goal there was to one day bring me to an orgasm that would make me cry. It finally did happen, while we were on a vacation. What Sam didn’t know was that not all of those tears were the result of the orgasm. Half of them were tears of sadness, as I thought about the fact that I would never truly “have” this man, because he did not want to marry again, and certainly didn’t want more children, as he’d had a vasectomy after his wife had their fourth child. Yet, I was still so young; all of those things should have been ahead of me.

I think that Sam’s show of prowess in the bedroom was spurred on because of our age difference, too. He was very possessive of me, and by making sure I was fulfilled in this area, he reassured himself that I would have no thoughts of seeking pleasure from anyone else.

The problem there is that, as time goes by, we come to the realization that sex is not all we need, and while I certainly had all that I wanted, he was still unable to give me what I wanted most—a stable marriage, children, and a future that included growing old with someone.

The post Why the Sex Is So Much Better with a Man Almost Twice My Age appeared first on Sugar Daddy Online Dating by EarnTheNecklace.com.

Along with being 26 years older than me, my boyfriend Brandon had very different views in life. The most crucial to our relationship was our religious standpoints. As a Christian man who wanted a woman who was “equally yoked,” I was not up to par with his expectations. Brandon was not the kind of guy that believed that women belonged in the kitchen or that we are to be submissive to men, but he did expect me to practice what he preached and that was not OK with me.

I was not Christian and did not plan to be anytime soon. I liked to be open to the concept of different beliefs and all I got from Brandon was a narrow-minded Bible thumper. Don’t get me wrong; I liked Brandon and his faith was refreshing, but when he started to point the finger at me, I did my best to not tell him to look in the mirror before he judged.

This subject is a really big sore spot in our otherwise happy relationship, but it was a situation that needed to be talked about and as Brandon expressed more and more of his feelings for me, the more I got angry at myself.

“It’s just that, Lena, I’m starting to have deep feelings for you, but I want to know that you’ll walk with me and Him. I can’t sit here and pretend that I’m OK with being with someone that is not walking with Jesus and at any moment can leave me if she finds someone who has the same beliefs,” I remember Brandon telling me that night in his car.

I was so angry and tears were streaming down my face from the sheer anger I had in myself. “I just don’t get why you think that me being Christian is going to change the possibility of me cheating on you,” I replied. “I think by now you should know the kind of person I am. I accept your beliefs and I wouldn’t leave you and go with someone else because your beliefs aren’t the same as mine. And how can you say that I’m the one keeping you from going to church? Didn’t you ask to go tonight and I said yes?”

He looked at me and hesitated on what to say next. It was the first time that Brandon had seen me crying and I knew that it was making him uncomfortable. But I was not the type to just scream and shout when I felt like I was being attacked; I got angry and with that, tears usually followed. “I know Lena, and I appreciate that you do go, but sometimes I feel like you don’t want to go and you do it just to make me happy,” said Brandon.

“I don’t feel like you’re forcing me, and if I really didn’t want to go, I would tell you. But I do it out of consideration for you and I respect you. Trust me, if I didn’t want to go I wouldn’t,” I retorted. “And if I don’t like it, what is the big deal? I’m going to support you, not to change my life.” I knew the last part was like a punch in the mouth, but at that point, I didn’t care. Here I was dating this guy and it hadn’t even been a year and he wanted me to change. I prided myself in never being in a relationship where I was being told that I wasn’t good enough and the minute Brandon said the words, “You’re not the woman I thought you were,” it was as if he had said I wasn’t good enough.

“Wow, isn’t that typical. Just like every woman. You all know just how to make yourselves the victims and turn it around on the man,” Brandon said with an angry laugh as he shook his head.

I looked at him, surprised and hurt. He was again generalizing women, but this time he didn’t understand just how resentful he had sounded. This wasn’t about me being non-Christian; this stemmed from something else. This was pain and hurt that Brandon didn’t know what to make of and he didn’t know how to express it, let alone where to point it. And I had to wonder, was he even over his previous marriage?

The post How to Know If You’re Really Arguing, or If It’s Just Because He’s Not Over His Ex appeared first on Sugar Daddy Online Dating by EarnTheNecklace.com.

Nothing could beat my older man’s sense of surprise and creativity! Our 22-year age difference gave Sam an edge over younger men in knowing how to keep the fun in a relationship. Most men in my age group—mid-20s—didn’t have the money or inventiveness to keep me on my toes the way Sam did.

“I want to take you somewhere for dinner Friday night. Wear a nice dress, but bring a warm jacket,” Sam said. Knowing how he operated, I would spend the next few days in great anticipation about where we were going, which, of course, was exactly what he intended. That Friday, he drove 60 miles to a romantic, outdoor restaurant that overlooked a lake. Ironically, the area we had just driven from was surrounded by lakes.

Another one of his favorites would happen as I was following him home from work. I’d see his turn signal indicating he was turning off the regular route. Following, I’d see him drive into the parking lot of one of our favorite restaurants, and he would buy me dinner. He did this just enough that I didn’t expect it, so when it did happen, it was always a delight.

One surprise Saturday, he picked me up for lunch and drove 75 miles up into the hills to a porcelain factory that had a restaurant attached. We had lunch at a table overlooking the hills and then toured the factory.

Sam’s years of experience with women—his wife and his affairs—had taught him that we like to be “swept away.” He did his best at this, which, of course, gave him extra rewards in the bedroom.

Like most women would, I loved the pampering! Sure, he was 46, but I was only 24 and still enjoying life. There was plenty of time for me to marry and have a family. I was so into pleasure-seeking, however, that the next thing I knew, I was 34. That was when I pulled the plug on our May-December relationship and ended it.

Sam had always told me, “I make a better boyfriend than a husband.” I eventually found out that he couldn’t be more right.

While he was very much into the courting aspect of our May-December relationship, he didn’t want the attached strings of another marriage. The truth is, early on in our relationship I did want to marry him, but he did me a huge favor by leaving us status quo, because when it ended, it was clean, and I did not have the heartbreak of a divorce.

Two years later, I did marry a wonderful man, but our attempt at having children proved unsuccessful. I had one non-functioning ovary, fibroids in my uterus, and severe endometriosis. We did not seek out extraordinary procedures to get pregnant, since I was getting older; rather, we decided to leave it to fate. So, while I might have been too late to have any children, fortunately I was not too late to find the ideal man to marry, share my life with, and grow old with.

The post Why I Said ‘No’ to Marrying My Sugar Daddy appeared first on Sugar Daddy Online Dating by EarnTheNecklace.com.

There’s a pretty good chance that if you choose to be with an older man, he will come with baggage. Sam was 46 and had been married over 25 years by the time he divorced. He had four children with his wife. I was 24, so with a little math, you can conclude that his eldest child was around two years younger than me. “Cold” is too soft a word to describe my first meeting with his son. I spent 10 years with his father, and the second time I saw him was 11 years later at Sam’s funeral, where he looked right through me.

The second child, another son—now we’re talking four years younger than me—I did see a few times. He was not as distressed over the 22-year age difference, because he was quite preoccupied with his own life, and furthermore, he told Sam I was nice! I guess “nice” only gets you a few meetings in 10 years.

As if that wasn’t enough, I also had to meet Sam’s two daughters. You’d think after meeting his sons I would be prepared, but even still, my unusual experience with his daughters caught me by surprise.

Next were one daughter and then another daughter born five years after her, whom Sam described as a “surprise.” She was the surprise that prompted him to get a vasectomy. (No more children for Sam. So, think hard about what you want in your life!) These last two children were just young enough that the age difference was not as apparent to them as it was to their older siblings. What they recognized was that I was good to them and that their dad was happy. I saw a lot of both of them, and I have to say, I have some very special memories of those times.

Let us not forget the ex-wife, however! Chances are you will share some of your man’s time with issues regarding the ex-wife, like issues about money, housing, and kids. He may also see a lot of her since they did have kids together. Former spouse matters can also lead to arguments between you and your older man, which, years later, I wondered why I expended so much time and energy on.

Now, back to those younger children. While we were able to do things together, what about those many times when I was not part of their events? Special occasions like graduations, birthdays, school events and when they wanted time just with their father. That will happen, and you will feel hurt and left out. You will feel like you have just taken two steps back regarding your relationship with those kids, and you will feel animosity not only toward the “ex,” but toward your man, as well.

Only you can decide if the relationship is worth it. Look deeply into your heart and first figure out what you want for your life. Go over the positives and negatives in your relationship with your older man. Consider if you are holding yourself back from anything that could make your life fuller or more satisfying if you were not in this relationship. Remember, you are in the driver’s seat, and only you are in control of your destiny.

Not every first meeting with your older man’s kids will be like mine, but it doesn’t hurt to prepare for both the best and the worst.

The post How I Handled My Older Man’s Kids Who Were Almost the Same Age as Me appeared first on Sugar Daddy Online Dating by EarnTheNecklace.com.

I was 34, Sam was 56, and our age difference was becoming more obvious. Sam was getting grayer, and had less to become gray. He wore reading glasses, but now needed a small distance correction, so he got prescription glasses. He decided they made him look distinguished, so he wore them constantly. I thought they made him look old.

Sam had a fondness for alcohol. After retiring, he bought a bar/restaurant. The liquor was handy, and being the owner, it was just too easy. As the weeks passed, his coming-home time changed from early to late evening. I’d go to bed alone, only to awaken during the night, still alone. I would call the restaurant, and he would answer in a groggy voice. He had passed out in his office. I began to feel like a mother, calling in the middle of the night and asking him to come home. The drinking and late nights aged him further, making him appear more drawn and haggard.

One night, I awoke at 4 a.m., alone again. This time, I lacked the energy and interest to call him. I had had enough. It wasn’t until the next morning when I was leaving for work that I found out where he had really been all night. I found him asleep in his car, parked next to mine in the garage.

My parents invited me to spend a long weekend with them, during which I spent a lot of time gazing out the window and walking on the beach. I examined my life. I had given a precious window of my time to Sam—ages 24 to 34—a time I could have spent seeking my life partner. That weekend, I made the decision to end it, to give it up and spend some time alone.

Upon returning, I asked him to go for dinner. I waited until after dinner and coffee to tell him all of my thoughts. I told him I could no longer live with the ups and downs; not knowing if he’d come home; not knowing if he’d be drunk. We were no longer a team, and the sleepless nights were wearing on me emotionally and physically. And I couldn’t do it anymore.

He listened in silence, and then I saw the veins come out on his forehead. He became red-faced and furious. He exclaimed, “Oh, I see! Because I have a business to run and need to be there, and that doesn’t suit you, you want to end it! What about all I’ve done for you?! Apparently, since things are not going well as far as YOU’RE concerned, you’re ready to throw it all away!” He sure missed the point.

The discussion was escalating, so I convinced him to leave the restaurant. We drove home in silence. My mind actually wandered to how my family would cope after they learned Sam wrapped the car around a tree. He moved out the next day.

It was my choice to be with an older man, but time changed both of us, and the age difference only contributed to those changes, causing us to have incompatible goals. So, I made the choice to go forward alone. My choices then were limitless. Being in an age gap relationship has its perks, and I never regretted it, but there comes a point when the relationship runs its course and you have to decide what’s best for YOU.

The post Why I Ended My May-December Relationship with an Older Man appeared first on Sugar Daddy Online Dating by EarnTheNecklace.com.

My older man was certainly handsome, and always knew how to treat a lady. But as the years progressed, he became something else—tired. There was a 22-year age difference between us, and while his energy was good when he was in his late 40s, it had declined significantly by the time he was in his late 50s. At the time, I was in my mid 30s, and still raring to go. Our difference in vitality caused contention between us.

After we started living together—eight years into our May-December relationship—his energy began waning so much that it was getting hard to deal with. His idea of a good Sunday was turning on the television and falling asleep to a ball game. Sunday was my housework and laundry day, so I would move between the bedrooms upstairs to the living room downstairs with baskets full of laundry, each time passing this loud, snoring lump on the couch. As I’d look at him lying there, I’d get more infuriated every time. I tried to explain to myself that he was tired after a long week, but so was I.

When I had had enough of watching him sleep, I’d wake him up and suggest that we go for a walk, out for a quick dinner, or to the store—anything to get him to move. He’d admit that he didn’t have the energy, and would (sometimes) do what I asked, but I would just end up having to deal with his cranky attitude the entire time.

I realize that this scenario could also very well take place in a relationship with two similar-aged people, but the truth was that I could see his age was slowing him down—he was starting to act like an old man. We had been together almost 10 years, and although at first it didn’t bother me, our 22-year age difference now seemed to be blinking at me like a big, neon sign.

I decided that I wanted to join a fitness club, and thought it would be fun if we joined together. I also had an ulterior motive. He had just done his yearly physical and was diagnosed with high blood pressure and high cholesterol, but he did not seem to be as concerned about improving his health as I was. He was “too tired after work” to go to any sort of gym—and he certainly did his best to discourage me from going on my own. I’d always hear, “Why would you want to go without me? Are you going shopping for a younger man who’s full of muscles? Is that what you want now?”

Always keep in mind that if your man is at least 20 years older than you are, there’s a good chance he will develop some health problems long before you ever do. The health issues may be minor, but they could potentially change the entire relationship game plan. He was tired, and I was nagging him. He put in a heavy work week, but I worked 40 hours a week, too. He wanted the couch, and I just wanted him to be with me.

We love our older men, but chances are you’ll find they get tired faster and sooner than you’ll want them to. So, you either have to start joining him on the couch, or realize that you have a lot more living to do, and it may just have to be without your couch potato of a man.

The post The Biggest Challenge a Younger Woman Would Never Expect When Dating an Older Man appeared first on Sugar Daddy Online Dating by EarnTheNecklace.com.

Before I could get out of the house for my weekend trip with my boss, Mr. Brown—who also happened to my older lover—my husband pulled me in for a kiss. It was awkward, as it had been quite a while since we had been intimate like this, but it was nice. He told me to be safe, and off I went.

Also see: Why My Wealthy, Older Boyfriend Is Absolutely Irresistible: Part 1

The drive to the airport was long and boring—until my phone rang. I expected it to be my husband looking for the diapers or a lost shoe, but it was Mr. Brown. He asked for my location, and then told me to take the exit that came before the airport. I asked where I was going, but he told me not to worry about it, and that he would text me the coordinates to put into my GPS. I followed the directions, and 10 minutes later I pulled into a gravel parking lot. I saw the dresses in the window and realized that this was one of the best boutiques in the area. This shop specialized in designer dresses and jewelry that weren’t available to just anyone.

I got out of my car and walked to the door. When I stepped inside, I could immediately smell fancy perfumes and fresh-cut flowers. Not only was this a boutique, but they also had a small area partitioned off that looked like a fancy salon or spa. I was so anxious that I jumped when someone came over to greet me. She asked if I was Mr. Brown’s guest, and when I nodded, she told me that they would treat me well. I was led to a seat and handed a spa service list. The prices were well above what I could afford, so when she let on that Mr. Brown had set no limit, I was ecstatic. I selected a facial, massage, and body treatment. She then informed me that after my spa treatment, I was to go to the boutique to select a dress for the Gala.

I was pampered from head to toe, and I was so relaxed. I strolled into the area where all the dresses were kept, and while normally I would be too distracted chasing my children around a store to really look, today these dresses had my full attention. The lady helping me brought out a number of dresses. When she laid them out in front of me, I was immediately drawn to a red Herve Leger dress, which ended up being formfitting in all the right places. I did a double take in the mirror—I never thought I would feel as sexy and confident now in my 30s as I did when I was in my 20s. The sales associate picked out a matching necklace and earrings set, along with a pair of cream-colored heels, and then she wrapped it all up. I tipped her generously, signed the receipt, and got back in my car.

I needed to be at the airport in 45 minutes, but first I wanted to text Mr. Brown to let him know how much I appreciated his thoughtfulness. I was at a loss for words. The only thing I could think of texting him was a photo of my delicately laced bra. When his only response was a smile, I knew he was as ready for this weekend as I was.

The post Why My Wealthy, Older Boyfriend Is Absolutely Irresistible: Part 2 appeared first on Sugar Daddy Online Dating by EarnTheNecklace.com.

Mrs. Brown was in her 30s when she married my boss—who was also my secret lover—and the agreement was that her father would take care of Mr. Brown’s education. The only thing that her family wanted in return was for the couple to generate new money for the family business. Mrs. Brown told me that the marriage had nothing to do with love—it was all for wealth and power. If people knew their marriage was unsuccessful, it would taint her family’s name and legacy. She knew that he had messed around with other women before, but she had always caught him before any of these ladies had the chance to dig their heels into his fortune, or to convince him to leave her.

Mrs. Brown continued to tell me that while he fooled around on her, he would never end the marriage because then he wouldn’t inherit any money if she died before he did. I looked at the sadness in her eyes as she spoke about her husband. She never loved him, she just did as her father wished, and I could see she was regretting her decisions. She told me that she wanted her husband to date and live the rest of his life the way she couldn’t live hers, especially now that her health was getting worse. She wanted him to be happy with someone who really loved him.

She asked again if I would be her ally. I told her that I would keep an eye out for anything suspicious. She responded by saying that she always liked me, and wished that her husband could have found someone more like me.

She started to tear up, so she pulled her Dior shades over her eyes and ordered us both another round of drinks. I thought about what I was going to do with this information—was I going to tell my lover that his wife might actually be OK with our situation? Or should I pretend like this meeting never happened? I went with the latter and decided not to tell Mr. Brown about the meeting, at least not right away.

I casually mentioned to Mrs. Brown that I needed to get back to work to finish organizing the company’s Easter egg hunt, and that I couldn’t stay for another drink, but she insisted so I stayed put for a little while longer.

The conversation eventually died off and I was relieved when I could feel my phone vibrating. It was a text from Mr. Brown asking to swing by his condo later. I finished my drink and told Mrs. Brown that I’d surely see her around. At this point, I was officially at a loss for what would happen to my relationship with Mr. Brown.

The post The Dangers of Getting Way Too Involved with a Wealthy Older Man…And His Wife: Part 3 appeared first on Sugar Daddy Online Dating by EarnTheNecklace.com.

A lot of women these days are asking about the concept of chivalry, probably because you don’t see much of it anymore. But if you grew up in an earlier generation, you’re probably a little more familiar with the term.

Chivalry was a term used to describe knights who were loyal, courteous, protective, honorable, and gentle with their women. A knight was also supposed to possess traits like courage, humility, obedience, and chastity. Knights who lived by the code of chivalry were to show self control and respect toward women, as well as protect the innocent, weak, or unarmed. They were to administer justice, avoid cheating or lying, and were expected to avenge the wronged. In love, chivalry usually refers to the gentlemanly way that a man treats a woman—doing the right things, for the right reasons, at the right times—like opening the door for her and refraining from taking her to bed the first chance he gets.

Chivalry definitely seems hard to come by these days, with so many women under the impression that if a man is being nice to a woman, it’s only to get into her pants. As a woman in her 30s, it has been difficult dating a man who’s 23 years older, but my gentleman’s manners more than make up for the big age difference.

I have found it very refreshing to be with someone who is used to treating a woman like a princess. Most of the men I’ve dated between high school and now have no idea how to treat a lady—they don’t open doors, pay for dinner, or even compliment you on the little things. I’m sure a lot of women have had similar experiences. That’s why sometimes it can be hard to just accept an older man’s gracious or kind ways—you always feel the need to doubt his intentions.

When I talk about chivalry, I don’t mean in the sense that the man does everything for you, like taking care of each and every bill when you go out to eat, or carrying you through the front door every night. Ladies, your independence is still very important. But I, as well as most women, just want a man to be courteous and to show respect to me as a woman.

Believe it or not, being catcalled and groped doesn’t count as a compliment. Older men understand this, and as hard as it might be for you to accept his chivalrous ways, it doesn’t take too long to get used to. Take advantage of it if you’re dating an older man. Let him pull out your chair at dinner and hold your hand. Let him carry your heavy bags and pick up the tab. Older men were raised differently then men today. Older men would be more than happy to shower you with gifts, and pay you a compliment if you’ve worn your hair differently or cooked a delicious meal. It’s OK to lavish in this and feel like a princess. Take pride in the fact that your man does these things for you, and show him how much you appreciate his gestures.

If you’ve never dated an older man before, or a man who knows what it means to show chivalry, you’re missing out. I know in today’s times, a lot of women are used to doing everything themselves and don’t think they need that from their relationship. I used to be the same way, but now, I will never turn down my older man’s offer to carry my groceries or save me from a big spider. All ladies deserve to be treated like a princess, and my older man knows just how to get it done.

The post Proof That a Younger Woman Gets Treated Better When She’s Dating an Older Man appeared first on Sugar Daddy Online Dating by EarnTheNecklace.com.

I was out on a romantic dinner date with my new older man, Keegan. As the evening wore on, we both drank a lot more than planned, but we were having a really great time. We tried making it through a movie, but decided it was best we head back to my apartment nearby and sober up. The weather was bad, so we rode in one car and once we got home, we both fell asleep. That was the first night Keegan stayed over. He fell asleep on the couch, and I on the bed. Around 2 a.m., I woke up confused, so I went to find him.…

The post The Weirdest, Most Unforgettable Thing He Ever Did to Get Me Into Bed (Not What I Expected!): Part 1 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

During the summer break when John’s son was around, we went out a lot. He seemed to like me and began confiding in me. “Isabella, promise you won’t tell my dad,” he once said out of the blue. “Tell your dad what? I promise, I won’t tell,” I said. “Why is it that my dad always pushes people away? He doesn’t deserve you, you know? I listen to the way he speaks to you and you don’t even deserve it. I worry about him. I worry that he’ll end up alone with no one who cares about him.…

The post The Shocking Confession My Sugar Daddy’s Son Made About His Father: Part 2 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

Very slowly, Keegan removed his shirt, revealing a thick hairy chest and stomach. I immediately touched it; his chest hair was definitely covering up defined pectoral muscles. He pulled me in close, lifting my shirt, and sliding it effortlessly over my head. Tit for tat, piece for piece, we helped each other remove our clothing until we were naked. I remember the feeling of his warm body and hot water against my skin in the shower. As he held me close, he kissed me gently as the water just rushed over us.…

The post The Weirdest, Most Unforgettable Thing He Ever Did to Get Me Into Bed (Not What I Expected!): Part 2 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

John was extremely loving for the first two weeks after I returned from England—he had no idea that I was secretly planning to move there just to get away from him. He showered me with attention and whenever I mentioned that I needed something, he gave me as much money as I wanted. He was acting paranoid, telling me he knew I was going to leave him and that he could feel it. I denied it, but in reality, I was going to leave him in the most discreet way possible. I was tired of his ways and I wasn’t going to deal with it anymore.…

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I spent most of that January in England with Brian. I liked what he stood for and it didn’t take him long to love me. He was single, and this time he really was—there were no secret wives or girlfriends. He had never been married, so that was a plus. He had his own business as well, but with him it was never about the money, and it still isn’t. He loved me, he adored me, and all he wanted was for me to feel the same. It didn’t take long for Brian to propose and I accepted. When I went back to the island where John was, I began to put my plans into action.…

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Keegan was extremely hesitant and cautious while dating me, even though he was the happiest and most compatible with me. But because of the stigma attached to our age difference and the taboo “cradle robbing” labels that he was terrified of, he continued seeing me semi-seriously, while keeping one foot out the door and his dating options open “in case” someone more appropriate came along. This was all new for both of us, and because we were so happy when we were together, it hadn’t occurred to me that this was exactly what he was doing until just after New Year’s.…

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Everyone has some sort of criteria of what they do and don’t want in a relationship, and May-December relationships are no different. Most young women who date older men are looking for someone who’s mature, confident, financially stable, and can look after them both physically and emotionally. And that’s on top of good looks, a sense of humor, and all those other things that women generally tend to favor in a partner. Most older men in May-December relationships also have their own list of requirements when it comes to finding the perfect younger woman, but there’s one thing that both men and women value in a relationship—an active sex life.…

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I longed for my happily-ever-after ending. At the age of 18, that was the only thing that I was missing—at least that’s what my 18-year-old self thought. I had been accepted at a good enough college and my best friend was going with me. It was all falling into place for me; I was just missing him, that Mr. Perfect, that Mr. Right, the one relationship to complete my perfect after-high school ending. I was young, naïve, and had read too many romance stories than should be allowed. Before I knew it, the first semester of college was over and done—I was still single.…

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As I walked across the stage at my graduation, I could sort of hear my mom talking to my older man, Keegan. She purposely chose to sit right next to him, so that she could say what he needed to hear as he watched me accept my degree.  I could see his eyes lighting up as she talked and he put two and two together. His friends were doing him a serious disservice by trying to talk him out of dating me, especially having no experience with an age gap relationship. The only experience they were going on was horror stories other people had had in the past.…

The post The One Thing My Rich Older Man Wouldn’t Give Me (No Matter How Much I Begged For It): Part 1 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.

Much to my surprise, Keegan didn’t give me an answer that night. So, I assumed he did not want a serious relationship with me, despite telling me that he loved me and working so hard to get back together with me. Then it dawned on me that he had unfinished business with another woman and needed to end things entirely with her before committing to just me. I felt so insulted. This made me sad, as I was really hoping we could put that whole situation behind us and move on.  If you asked him today, he would tell you that he did in fact answer me, and I insulted him.…

The post The One Thing My Rich Older Man Wouldn’t Give Me (No Matter How Much I Begged For It): Part 2 appeared first on Dating Older Men | Age Gap Dating, Relationship Advice & Real Stories.