Is Your May-December Relationship Struggling? Why You Might Be the One to BlameIs Your May-December Relationship Struggling? Why You Might Be the One to Blame

Have you ever stuck around and clung on to a May-December relationship even if you weren’t the happiest in it? It might have something to do with your self-esteem. Researchers from the University of Waterloo recently conducted a study and found that when people have low
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What Not to Do When You’re Meeting Your Older Man’s Ex-Wife for the First Time: Part 1What Not to Do When You’re Meeting Your Older Man’s Ex-Wife for the First Time: Part 1

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
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What My Older Man Was Hiding From Me... And What I Did When I Found Out!

It starts off like a dream come true. I got pampered with luxurious gifts, vacations, even my own house, all from a man who’s old enough to be my father.
Things really heated up in the bedroom as his sexual experience really turned me on. I thought he was a perfect gentleman. But things aren't always what they appear...
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How I Know Sugar Daddies Give Better Dating Advice Than Best Friends: Part 1How I Know Sugar Daddies Give Better Dating Advice Than Best Friends: Part 1

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
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5 Critical Facts About Sex with Men Over 505 Critical Facts About Sex with Men Over 50

Some of the most common questions we see about couples with a big age gap, particularly when it’s a younger woman in a relationship with an older man, are about sex. A lot of people assume that if he’s much older, the sex can’t possibly
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At First I Thought My Sugar Daddy Was Perfect, Until I Discovered His Secret

He was old enough to be my father. But his age only opened me up to sexual experiences like I never imagined. And then, the money! Cars, jewelry, vacations, even a house! I was in love. That was until I found out about his secret.
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What It Took to Make Me Realize That I Didn’t Want to Be a Sugar Baby AnymoreWhat It Took to Make Me Realize That I Didn’t Want to Be a Sugar Baby Anymore

Getting off of the ship a couple of days later was a long, nerve-racking ordeal, what with passports, luggage, and getting a flight back to Chicago. I couldn’t wait to be back in my own apartment—I couldn’t wait to spend some time alone and to
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Too Much for a First Date? The Big Surprise My Sugar Daddy Had for Me and My Friend: Part 2Too Much for a First Date? The Big Surprise My Sugar Daddy Had for Me and My Friend: Part 2

We arrived at the casino rather quickly. As we approached the blackjack tables, the Greek God pulled the chairs out for me and Tori to sit down. He then laid a stack of one hundred dollar bills in front of me and handed Tori her
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Were the Great Sex and Luxurious Gifts Worth Dating a Sugar Daddy?

I was always attracted to older men, but I never thought I would wind up in a situation like this! Sure, the sex was amazing… the gifts were expensive… and the attention was addictive. But when I dug a little deeper, I realized that my sugar daddy may not have been all he claimed to be.
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How I Landed a Luxurious French Cruise from a Rich Man Who’s Old Enough to Be My Father: Part 2How I Landed a Luxurious French Cruise from a Rich Man Who’s Old Enough to Be My Father: Part 2

One evening, Patrick took me to the casino and insisted I play the slots. I had never been to a casino before, but I knew there was some serious money flowing there. Within five minutes, I won $1,000.00. Patrick beamed; he was so proud of
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Too Much for a First Date? The Big Surprise My Sugar Daddy Had for Me and My Friend: Part 1Too Much for a First Date? The Big Surprise My Sugar Daddy Had for Me and My Friend: Part 1

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
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My Sugar Daddy Affair with an Imperfect Gentleman

He seemed so perfect. Older, sexy, wealthy and established. He catered to everything I ever wanted, in and out of the bedroom. But there was something not right about him. And when it was exposed, it created one of the most sensational stories ever published.
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Too Much for a First Date? The Big Surprise My Sugar Daddy Had for Me and My Friend: Part 1

high end dating

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.…

The Best Way to Strengthen Your May-December Relationship

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When you’ve been in a May-December relationship with the same person for a long time, it can sometimes start to feel like it’s fizzling out. That’s not to say that the relationship has gone completely sour—it’s just not as exciting as it may have been in the beginning when everything was new and electrifying. We’ve seen this happen to a lot of May-December relationships, because they often start out hot and steamy and then calm down once the couple becomes more comfortable with each other.…

The Elaborate Plan My Sugar Daddy’s Wife Came Up with to Get Rid of Me (For Good): Part 2

dating a sugar daddy

When I finally spoke to Keith, I told him I got robbed, but I just didn’t tell him who I was with. I had nightmares after that and my mom was worried. The police had gotten information implicating Keith’s wife, and my mother didn’t want me taking the case any further out of fear for my life. I had started getting anonymous calls and when I answered, the person on the other end would hang up.
That December, Keith told me he was going to come to the island for two weeks and his plans were to spend one week with me and the other with his wife.…

Why I Know There’s Nothing My Older Man Won’t Do For Me: Part 2

dog collarThe Stetson man felt responsible for Frankie being gone, and I was a mess of emotions. The three of us searched the neighborhood, and after several hours with no luck the very married Stetson man needed to get home. My friend and I continued the search well into the dark hours of the evening. We put up fliers; we called out his name; we asked people if they had seen him. But still no luck. The Stetson man felt horrible, and he phoned many times that evening to follow our progress. The next morning he called and said that we needed to replace all our Frankie posters with ones that offer a reward—my boyfriend was going to give $1,000 for Frankie’s safe return.…

Sugar Baby Exposes the Truth About Her Married Sugar Daddy

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Getting an education doesn’t come cheap these days, and with tuition fees constantly rising, more and more students are turning to a sugar daddy to help cover the costs. In fact, one popular sugar daddy dating site saw a 53% increase in the number of college students signing up in 2013 alone.
Although sugar daddy dating is quickly gaining momentum, a lot of people still question whether it’s really the right path for a young woman in school. To help set the record straight, one young woman from the University of Westminster has opened up about her decision to become a sugar baby and what her relationship is really like with not one, but two sugar daddies.…

I Can’t Afford My Sugar Baby, But I Think I Love Her—Now What? (By the Way…I’m Married)

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QUESTION: I am 55 and just started dating a 23-year-old college student—this is my first time trying this.  We hit it off right away and have already had a lot of fun together. However, I am married so we have to be very discreet. Plus, because of my situation, I can’t support her enough financially to meet her expectations. So she has been honest that she can’t be in an exclusive relationship as a result. She is also coming off a sugar baby relationship that ended suddenly, leaving her with bills to pay, so she doesn’t want to put all her “eggs in one basket.” Since we can’t be together all the time, it drives me nuts thinking she might be on other dates, but I have asked her to never discuss other sugar daddies she might be seeing. …

Is This What He Really Means When He Says He Doesn’t Want to Get Married?

age_gap_dating_september17_13If you’re dating an older man, have the two of you discussed marriage? If he’s a lot older than you are, there’s a good chance that he’s already walked down the aisle once, and if he has apprehensions about a second or third marriage, it may actually have nothing to do with you. It turns out that a lot of people nowadays are simply choosing not to get married again, and instead opting for just living together.
The number of people in the U.S. who are remarrying has dropped by 40% over the past 20 years.…

Why You Should Think Twice About Asking Your Rich Older Man If He Ever Plans to Marry You: Part 1

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As Marco packed for his trip and I sat there reeling, wondering what changed, I couldn’t help but feel hurt, so I dug my “grave” a little deeper. I asked him the dreaded question at the worst possible time: “Where do you see us in one year, or three, or five, or even 10 years?” But before he could respond, I fired a few more heavy hitting questions at him. “Do you picture us ever getting married? Having kids? Are we OK in that respect?”
Looking back, it was a bit nuts for me to run full speed into that type of conversation so early into our relationship, and especially as he was packing to leave.…

The Outrageous Bedroom Experience My Sugar Daddy Gave Me on New Year’s Eve

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My older man, Patrick, knew the whole idea of his son donating sperm for us to have kids was out of the question, so he didn’t push it. We returned to our “normal” selves, just enjoying each other and Chicago. His sexual desire for me was stronger than ever and I pretty much responded, including the early morning trysts. And I mean every morning.
New Year’s Eve was coming up and he made a reservation for us at a new posh hotel in Chicago. It was a package deal that included dinner, dancing to live music, a suite, and breakfast served in the room on New Year’s Day.…

A Surprising New Place to Meet a Future Sugar Daddy

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If you’re on the hunt for a sugar daddy, you know it isn’t always as easy as walking into a bar, cuddling up to a handsome older man, and calling it a night. It usually takes just a little more effort to find a sugar daddy worth keeping, but it helps if you know where to look. The next time you’re invited to a wedding, you should join in the festivities because, as a new survey reveals, there’s a good chance you could meet someone. If you’re a younger woman on the hunt for a sugar daddy, weddings are a good place to start looking.…

What You Don’t Know About the Older Men Who Date Younger Women: Part 2

age gap dating

The following morning at nine o’clock sharp, Peter called. I told him I was free for the day and asked what his plans were. That would be my first time actually driving anywhere with him; I could never resist an offer to drive out in the country. I loved the smell of the field and the scenery. It always made me feel a sense of freedom, as if I had nothing to worry about; everything felt perfect.
As much as I wanted to tell myself that I was street smart, I was so naïve. I had no right entertaining a conversation with him or even going anywhere with him for that matter.…

The Most Awkward Situation I’ve Ever Been In with a Rich Older Man

age gap dating

We arrived at the wedding reception hall a half hour early. My older man, Keegan, quickly located the bathroom and the bar—thankfully, too, because I needed both. My nerves were going crazy. This wedding was going to be the first time I would meet Keegan’s whole family, and he had already told me that there may be some who wouldn’t take too kindly to our big age difference.
I was so anxious that I downed a rum and coke seconds after it was given to me. “Whoa! Slow down there, lover,” Keegan whispered to me.…

What to Do When You Don’t Come First

He Said, She Said: Chelsea and Trent on What to Do When You Don’t Come First

QUESTION: I just found my boyfriend’s stash of adult videos discreetly hidden in his sock drawer. Am I not enough for him? Why would he hide them from me?
CHELSEA SAYS: He is probably hiding them from you because he knows that you’re going to freak out, kind of like you’re doing right now, and he just wants to avoid having to talk to you about it. Everybody has their thing, maybe this is his and he’s just not comfortable sharing that with you, at least not yet. It doesn’t mean that sex with you isn’t enough.…

Why Older Men Make Better Lovers

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If you’re in a May-December relationship, whether you’re the older man or the younger woman, you’ve probably been asked at least once about your sex life. That’s because people are curious about the chemistry in the bedroom—if she’s young and vivacious, and he’s significantly older, can he keep up? Or even more importantly, can he get it up?
A lot of younger women who are in a May-December relationship with an older man will tell you that their sex life is not only active, but it’s very satisfying as well.…

How Do I Convince My Sugar Daddy to Get a Little More Creative with Our Sex Life?

age gap dating

QUESTION: Let me start by saying that sex with my older sugar daddy is amazing. We’ve been together for almost six months now, so he’s learned what really drives me wild. However, he isn’t very spontaneous and only likes to have sex in the bedroom. Meanwhile, I love changing things up once in a while—I especially love doing it in crazy places. There’s just something so thrilling about it. How do I even begin to approach the subject with my sugar daddy?
CHELSEA SAYS: It sounds like you both just have different tastes when it comes to sex.…