When to Have Sex with a Sugar Daddy

By Downtown LA SD

Oct 21, 2016

Finding the perfect arrangement doesn’t happen just because you want it. It takes patience, and playing the game with the pieces you’ve been dealt. Yes, I’m talking about your body. It’s confusing gauging when to have sex with a Sugar Daddy. I’m about to offer some powerful advice here, so lean in Babies.

A Sugar Baby friend texted me the other day asking me how I am, about my current exploits, etc. Nothing out of the ordinary. Lulled into this routine state of normalcy, I was unprepared for the bomb she then dropped on me.

The night before, she’d met a POT for dinner, but they’d instead skipped dinner, headed upstairs to his hotel room, and had sex. Twice. You might ask, where’s the “bomb” in that? Sugar Babies and Sugar Daddies do that sort of thing all the time. But with this particular SB, it was a radical act. You see, she’d given up her V-card!

The Story

This is no 19-year-old college girl. She’s a late-20s, experienced woman, with a career, a degree, pets, and her own apartment. She’d explained to me previously that she had never met “the right man,” but for some reason, this married POT was suddenly attractive and kind enough for her to let down her guard and finally, at long last, give up being a virgin.

Again, you might think, so what? Lots of women do that. And you’d be right. But here’s the bigger bomb she dropped: there was no prior discussion of arrangement terms of any kind. She essentially gave up her V-card for a couple of drinks and a view of the city from his room. I’ll give you two guesses what happened after that. Here’s a hint: they’re not engaged. That’s right! He stopped communicating with her entirely.

Now, the story is still playing itself out as I write this, but suffice it to say that this man has not, in the last several days, made an attempt to reach out and set up date number 2. But whether he does or not, the Sugar 101 lesson here is: if you’re going to give Sugar, you must first GET SUGAR. 

It’s Called “Mutually Beneficial”

As a Sugar Daddy who’s had five significant, long-term arrangements, I’ve also had more than my share of POT Sugar Babies that didn’t work out, despite our getting intimate. Even when that happened, though, I always remembered that this is Sugar Dating.

I might be in the minority here, but I make sure to agree upon arrangement terms before anything sexual happens. I strive not to take you for granted. I’ve failed many times, and as a work in progress I’ll likely fail again, but who better to warn you against that kind of salt?

Having a sexual encounter before he’s shown you he’s worth it will only end with regret. As a rule of thumb, never agree to sex (especially on a first meet) unless it is something you truly want to do. Period. That’s why it’s called “mutually beneficial.” It requires you both to be upfront about what you need to get out of the arrangement. 

Accepting Advances

He might be one amazing dude who you’re really into. Say you carefully weigh the situation and decide it’s okay to sleep with a POT. Heed my warning that it might not turn out as you envisioned.

Perhaps he does realize you’re the girl of his dreams, and in his sudden burst of gratitude he asks you to move in with him. Cue the alarm bells and red flags! In any case, the following possibility is more likely.

He got what wanted and now he’s ghosting you, leaving you agonizing over what the hell you saw in that loser in the first place (wah wah waaaahhh). Either way, it’s best to accept the consequences, chalk it up as a lesson learned, and move on.

Maybe You Get Lucky

Maybe the next day, Mr. Freebie texts you and says, “Hey, hun, I realize that we never talked about the allowance stuff. How about I take you on a trip to Aruba this weekend and we can work all that out?”

The sun just rose in the west, but indulge me here. Would you suddenly forgive and forget? Maybe make him sweat for a few days thinking he’s blown it. Then, calmly accept his invite after he first shows you how sorry he is for “shoplifting the pootie” (Jerry Maguire reference, old but effective). Never forget why you’re in the Bowl.

Face the Facts

Even though we think we’re tough and wise enough to endure the never-ending series of letdowns in Sugar, don’t forget you have value. If you want to share intimate, sexual companionship with your Sugar Daddy, then he needs to be deserving of that affection.


You’re beautiful, and intimacy with you should be treated as such. Even though it can be fun to jump each others bones, it’s better to first insist he honors your value. That is something you will never regret.