Tag Archives: May-December relationship

My Rich Older Man was Amazing in Bed, But When He Did This, It Just Blew My Mind

Being on vaca­tion with my older lover, Mr. Brown, who was also my boss, was amaz­ing and exhaust­ing. The entire time we were there, he was so atten­tive to me and my daugh­ters. Every day was beach adven­tures or trips to the zoo. At night, we went for din­ner at a fun restau­rant that catered to the kids—the enter­tain­ment kept them happy, and wore them out. We would come home from a […]

It’s Been 2 Years and the Sex Isn’t What It Used to Be—What Happens Now? (ANSWER!)

Mick Jagger Honoring L’Wren Scott

QUESTION: Me and my older man (he’s 18 years older) have been together for just over two years now. Our May-December rela­tion­ship is great and I’m very happy with him, but our sex life just isn’t as good as it used to be. What’s hap­pen­ing? Is our rela­tion­ship in trou­ble? CHELSEA SAYS: I’m guess­ing what you’re really try­ing to say is you’re not hav­ing as much sex as you used to? This […]

What 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 resume work­ing. Sur­pris­ingly enough, my older man, Patrick, did not act out­raged or hurt by my flat-out refusal to get mar­ried on the cruise. We really didn’t […]

The $8,000 Mistake My Sugar Daddy Made Trying to Make Me Commit: Part 1

If sex with my older boyfriend, Patrick, was like the ele­phant in the liv­ing room, then the sub­ject of mar­riage was the dinosaur stand­ing next to it. Unlike many May-December rela­tion­ships where both peo­ple are com­fort­able just being together—or one, if not both, of them are already married—Patrick was dying to marry me. At first, it was flat­ter­ing and, although I acted pleased, I tried to make light of it, change the subject, […]