What My Abusive Sugar Daddy Taught Me About Being a Good Wife: Part 2What My Abusive Sugar Daddy Taught Me About Being a Good Wife: Part 2

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,
Read the whole Story

What Happens After You Tell Your Family You’re Dating a Rich Man Who’s Twice Your Age: Part 1What Happens After You Tell Your Family You’re Dating a Rich Man Who’s Twice Your Age: Part 1

Just before Thanksgiving, my new older man, Keegan, and I slept together for the first time—and it was incredible. But then we kissed each other goodbye and headed our separate directions for the holiday. I spent Thanksgiving with my family and he spent thanksgiving with
Read the whole Story

What My Abusive Sugar Daddy Taught Me About Being a Good Wife: Part 1What My Abusive Sugar Daddy Taught Me About Being a Good Wife: Part 1

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
Read the whole Story

The Weirdest, Most Unforgettable Thing He Ever Did to Get Me Into Bed (Not What I Expected!): Part 2The Weirdest, Most Unforgettable Thing He Ever Did to Get Me Into Bed (Not What I Expected!): Part 2

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,
Read the whole Story

The Shocking Confession My Sugar Daddy’s Son Made About His Father: Part 2The Shocking Confession My Sugar Daddy’s Son Made About His Father: Part 2

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
Read the whole Story

The Weirdest, Most Unforgettable Thing He Ever Did to Get Me Into Bed (Not What I Expected!): Part 1The Weirdest, Most Unforgettable Thing He Ever Did to Get Me Into Bed (Not What I Expected!): Part 1

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
Read the whole Story

The Shocking Confession My Sugar Daddy’s Son Made About His Father: Part 1The Shocking Confession My Sugar Daddy’s Son Made About His Father: Part 1

My sugar daddy, John, was waiting years to develop a piece of land he owned to build property. His plans had finally been approved and it seemed everything was going to work out. I was hoping he’d unwind a bit after getting the good news,
Read the whole Story

What My Sugar Daddy Did For Me to Make Our First Thanksgiving Together Absolutely UnforgettableWhat My Sugar Daddy Did For Me to Make Our First Thanksgiving Together Absolutely Unforgettable

My new older man, Keegan, and I headed out for the night; it was the night before Thanksgiving. Dealing with the holidays while dating someone new is always a tricky feat. Despite this, we were insistent on going out. This time, we went out to
Read the whole Story

Why You Need to Be Careful with Rich Older Men Who Go to Strip ClubsWhy You Need to Be Careful with Rich Older Men Who Go to Strip Clubs

It was my best friend’s birthday and I told her I would be bringing a date with me to the party she was having at her home. My new older man, John, and I were an odd match and when I introduced him to my
Read the whole Story

What It Means When an Older Man Tells You He Loves You… and Then DisappearsWhat It Means When an Older Man Tells You He Loves You… and Then Disappears

QUESTION: I met an older man online a couple of months ago; I’m 28 and married, and he’s 43 with a girlfriend. It was an instant connection. We talked online every day, which led to eventually talking over the phone. He told me he was
Read the whole Story

How a $6,000 Lap Dance Gave Me the Courage to Leave My Controlling Sugar Daddy: Part 2

dating a sugar daddy

By February that year, I was restless, to say the least. Even though I was just bartending at the strip club, from time to time I would get up on the stage and dance a set, just like the rest of the girls. The male attention was flattering and a huge ego boost. The extra money was great, but the guys were not jiving with the fact that I wouldn’t do private dances with them.
On Valentine’s Day, Marco was in South Carolina at a client site, but had sent a bouquet of flowers, chocolates, and a card to my work.…

The One Offer My Sugar Daddy Made Me That I Just Couldn’t Refuse: Part 1

dating_a_sugar_daddy_november2_13

The next morning, I awoke to the sound of a doorbell. My Greek God ordered breakfast. He was one sight to see, wearing his jeans and a white dress shirt with the buttons undone. I couldn’t help but feel like I was in some dream. “Good morning, princess. I thought you would enjoy breakfast in bed.” He smiled and brought a tray to the bed. Everything was just perfect. Plus, I was starving after our night together.
After I finished eating, I told him that I was going to take a shower. He nodded his head and I walked very slowly to the bathroom—I wanted him to see my body.…

Why I Couldn’t Leave My Older Man, Even After I Caught Him Cheating: Part 2

WhyICouldntLeave_Pt2As the months passed, it became more and more evident that Derrick, my older married man, was having some sort of a midlife crisis—and I was part of it. Everything we did was spontaneous and all about his desires. It was hard to see at first because, after all, I was the one receiving all of the lavish gifts. But at the end of the day, everything revolved around him. My existence in his life was dependent on him and his desires. Whatever he wanted from me he got on demand and to his liking. The times he spoke about his wife, and the reasons behind his unhappiness, were always all about him feeling trapped and exploited.…

What My Luggage Revealed About My Sex Life with My Older Man

age_gap_dating_december17_13

My older, wealthy boyfriend—the Stetson man—had a voracious appetite for sex, and I was surprised to discover just how healthy his sex life was. I had always assumed that as men grew older they became less interested in sex. I went from years of not being desired by my husband to being wanted on a daily basis by the Stetson man. And I have always made a point of pleasing my man, but there was this one instance when we had huge disagreement over how to handle a situation that involved highly sensitive information about our sex life.…

What Scares Rich Older Men the Most

older_man_younger_woman_october1_13

We tend to assume a lot of the time that all rich older men have no problem approaching a beautiful woman—isn’t it in their nature? But it turns out that the prospect of dating can sometimes be a scary thing for many older men, especially if they’re a single dad or divorced.
A recent survey asked roughly 500 men between the ages of 35 and 55 who earn a six-figure income (at least $100,000.00) about their biggest dating fears. More than half of the older men (54%) admitted that they usually struggle when meeting a woman in person for the first time, and the most common reason was that they didn’t know how to start a decent conversation with her.…

My Older Man Went on Vacation Without Me, So I Did This to Make Him Regret It: Part 1

My Older Man Went on Vacation Without Me, So I Did This to Make Him Regret It

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.…

The One Travel Destination You Should Never Let Your Lover Visit If You Want Them to Stay Faithful

may_december_relationships_january28_14

If you cheat on your sugar daddy while you’re on vacation, would you fess up? We recently put this question out to EarnTheNecklace.com readers and more than three-quarters (77.7%) of the respondents said they would keep their lips sealed. That might be because a lot of people are guilty of straying when they travel.
In a recent survey out of Britain, one in 20 respondents admitted to having an affair while on holiday, and they also revealed where they think it is mostly likely going to happen again: Ibiza, Spain.…

Is My Older Boyfriend Going to Cheat on Me with His Ex?

may_december_relationships_december12_13

QUESTION: I’m dating this older man who’s separated from his wife—they’ve been separated for about a year now, but they’re not legally divorced yet. He just told me he’s going to Maui with his ex-wife and their two young kids for the holidays; he says it’s an annual family tradition and they want to continue it for their kids’ sake. He also assured me that they would be staying in separate rooms. I’m trying not to get crazy jealous, but do you think I should be worried?
CHELSEA SAYS: I don’t blame you for being jealous, but unfortunately, I think this is one of those cases where there isn’t really much you can do, especially since it sounds like he was telling you, not asking you.…

The Weirdest, Most Unforgettable Thing He Ever Did to Get Me Into Bed (Not What I Expected!): Part 2

may december relationships

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.…

My Lucrative “Play Date” with a Very Rich Older Man (Who Also Happens to Be My Friend’s Ex)

age gap dating

The phone rang at 11:45 p.m., just as I was drifting off to sleep. It was my new billionaire sugar daddy, Michael. “Hello?” I asked still half asleep.
“What are you doing?” Michael asked chuckling. “You aren’t sleeping are you? Because I want to see you, say in a half hour?”
“I’ll be there in 45 minutes,” I responded as I sat up. I was suddenly very much awake.
“See you soon sexy.” And with that, he hung up. My friend and his ex-sugar baby, Kate, said he was exhausting, and boy was she right.…

What Happens to a Young Beautiful Woman Who Tries to Make Friends with a Rich Older Man: Part 1

What Happens to a Young Beautiful Woman Who Tries to Make Friends with a Rich Older Man

My new friend Keegan enjoyed working out and wanted a new workout partner, since he was alone for so long. There was this older man who was never married, never had kids, and was devilishly handsome with a personality that just clicked with mine so nicely. He apparently didn’t think I would be interested in him after hearing about my time with Michael, who was much older and much richer. Keegan thought I was out of his league altogether, so he never really considered me as a dating prospect—he “friend-zoned” me.…

How I Broke the News to My Sugar Daddy That I Was Pregnant (and It Might Be His)

may december relationships

For the first few weeks of my pregnancy, I was depressed. I still didn’t know whose baby it was and I hadn’t decided what to do. I hadn’t told a soul about it, including my older lover, Derrick, and my husband, Robert. I contemplated telling Derrick, but I wasn’t sure what his reaction would be. I could not tell my husband until I decided my plan of action. One way or another, I had to figure everything out. In my heart of hearts, I wanted to raise my child with my husband, but I could not live with the idea that it could possibly not be his.…

The Outrageous Gift My Sugar Daddy Gave Me to Make Up For My Horrible Boyfriend: Part 1

may december relationships

For days, I was in turmoil over breaking up with my boyfriend, Kirk. It’s funny, when everything was fine between Kirk and me, I was happy with my sugar daddy, Keith. But now it seemed like I didn’t want to be happy unless they were both in my life. Kirk couldn’t deal with knowing about my relationship with Keith, and that constantly led to arguments. And, because Kirk couldn’t handle the fights, he would just disappear.
After I decided to leave Kirk, he called consistently and kept asking people to speak some sense into me.…

Why It Pays to Be the “Other Woman” This Valentine’s Day

Why It Pays to Be the “Other Woman” This Valentine’s Day

Tomorrow may be Valentine’s Day, but it turns out that today is just as important if you’re dating a sugar daddy who’s married, because February 13 has reportedly become known as “Mistress Day.” Since married men who are having an affair will presumably be wining and dining their wives on Valentine’s Day, the majority of them will be spending the day before spoiling their mistresses and secret sugar babies.
According to a recent survey, nearly three-quarters (71%) of the married men polled said they’ll be spending February 13 with their mistress so that February 14 is left free for their wife, dousing any suspicions of their illicit affair.…

Why You Sometimes Have to Lie to Your Older Man to Get What You Want: Part 1

Why You Sometimes Have to Lie to Your Older Man to Get What You Want: Part 1After the lunch date with Mrs. Brown, my older man’s wife, I was nervous to go back to work the next day. Mr. Brown had sent me a text asking me to meet him at his condo, but I never responded. I decided that I needed to finish working on the Easter egg hunt that was being put on by our firm, and I had two daughters who wanted to spend some time with me. I figured I could afford to put my office romance on the back burner for the time being.
I spent the rest of the day playing with my kids, and finishing all of the work that I had been putting off.…

My Sugar Daddy Suddenly Broke Up with Me—What Went Wrong?

dating a sugar daddy

QUESTION: For the first time in my life, I tried being a sugar baby. I was dating this older man for almost a year and a half and I thought things were going great, until he randomly told me last week that he wanted to break up with me. When I asked him why, he just said that our relationship had “run its course” and it was time to move on. I couldn’t help but feel like I was just being used until something better came along for him. Is this normal behavior for a sugar daddy, or did something go wrong?…

The Real Reason I Called Off My Engagement to a Much Older Man

may december relationships

I was madly in love with my older man, Brian; we were both so madly in love with each other that at one point, he even asked me to marry him. I said yes instantly—he bought me the most beautiful ring with matching earrings. We had only just met maybe three months earlier, but with the time we spent together, it seemed like so much longer. He was so ecstatic I said yes that he sent me flowers and surprised me with a beautiful Gucci handbag. It was like a fairy tale. We visited a dress shop once to look at gowns, but I felt uneasy trying anything on as the shop attendant gave me a dirty look because of our obvious age difference.…

How Can You Get an Older Man’s Attention Online without Being Overly Sexual?

dating_a_sugar_daddy_november27_13

QUESTION: When it comes to finding a sugar daddy through online dating, how can I really get an older man’s attention without being overly sexual? The overly sexual thing seems to work, but it makes it that much more difficult to withhold sex as part of the arrangement. I’m willing to spend as much time with him as he wants, but I’m not comfortable having sex with him right off the bat. And I’m scared that if I’m overly sexual with my messages, they’re less likely to agree with holding off on sex.…

What My Sugar Daddy’s Assistant Did to Ruin My One Chance at a “Pretty Woman” Experience: Part 2

high end dating

Wow! I guess we’re all just cattle then. Thanks for the ego boost,” I retorted sarcastically as I grabbed the five outfits to try. As exciting and exhilarating as it was, this guy was just rubbing me the wrong way all together. I tried on the outfits, picked the only one I liked, and showed Anthony. He immediately vetoed it.
“No, get the black one. Mike will like it better on you,” he snapped.
“Well, I don’t care. I’m wearing it, so I choose this outfit. We have a whole store of outfits.…

How Do I Get My Older Man to Stop Flirting with Other Women?

may december relationships

QUESTION: My boyfriend is 18 years older than I am and we’ve been together exclusively for about a year and a half now. My older man treats me really well—he makes me feel special, always spoils me with gifts, and the sex is unbelievable. My problem is that when we go out together in public, he’s the biggest flirt. He’s always buying other women drinks and chatting them up, but when I ask him about it, he says he’s just being a gentleman and that I’m overreacting. What do I do?…