Never Have I Ever: Given Someone Multiple Orgasms

Here’s What It’s Like to Make Someone Climax Multiple Times in a Row

Here’s What It’s Like to Make Someone Climax Multiple Times in a Row

Have you ever played “Never Have I Ever” before? Here are the rules: Everyone puts up ten fingers, and you go around in a circle and one by one share something sexy or scandalous that you’ve never done before. When someone else shares something you have done, you have to put one finger down — and of course, drink. The first person to put all 10 fingers down loses (or wins, depending on how you look at it).

Well, AskMen is still playing Never Have I Ever, and the rules are simple: In each edition of this column, we speak to someone about doing something new in bed, whether it’s a long-time fantasy, something that just happened, or even something they regret. They tell us everything so you get an inside look at what some sexual experiences are actually like.

Why make someone cum once when you can make them cum, cum and cum again? 

Sure, it’s great to orgasm, but in the spirit of giving, let’s talk about giving someone else multiple orgasms. Daniel Saynt, the founder and “Chief Conspirator” of NSFW, New York City’s infamous sex and cannabis club, recalls the first time he gave someone multiple orgasms. 

To get the facts straight (which Saynt is not), the bisexual and polyamorous man has given all genders multiple orgasms, something we don’t hear about as often. 

Why? When we talk about multiple orgasms, the reference is usually directed towards women. People with vaginas don’t have the same recovery period as those with penises do. Keep on licking that clit or pressing down on that vibrator, and you can make a woman cum over and over. 

Saynt’s first time offering up multiple orgasms was with a woman, but since then, he’s enjoyed the multi-course menu with men just as well. 

AskMen spoke with Saynt about his first time, how genders differ in their ability to keep on comin’, and milking (the act of massaging the prostate until fluid releases).

AskMen: Have you given all genders multiple orgasms?

Daniel Saynt: Yes, I have actually.

Well, let’s start with the first time. Tell us about it.

I was around 24 when it first happened. I remember thinking that it was very cool. It felt very special to be able to do that. I think a lot of men have that mentality of wanting to please and make a partner happy, and I am one of those. When it finally happened, it was a badge of honor.

What gender was this person?

A female-identifying person. What was great about it was that she had already known how to, so it was more her guiding it around. There was mobilization on her part which helped. Back then, I was having long sessions of sex, but it was more penetrative. 

You’re focused on other things. Maybe oral is incorporated, but you’re not doing it as much; at that age, you’re just excited about sex in general. This person did guide me through “this is how I want to be pleased,” and that was very helpful at the time.

Give us the dirty details. How’d you make it happen?

For her, it was a combination of toys and oral. She was stimulating her clitoris while I was in her labia and really focused on it. I’d put a finger in to pull forward and on the back of her vagina, stimulating it at the same time. It was a dual-pressure stimulation that really helped her get there. 

There are many ways, but I would say the one thing in particular with women, and men as well, is that there are just so many different ways in which they get off. There are so many different ways to achieve orgasms, depending on the individual. It does not just focus on the clit, it can be penetration [of varying types], or it can be stimulating certain parts of the vagina. Just because you gave one partner multiple orgasms doesn’t mean you can provide another partner multiple orgasms the same way.

Let’s hear about giving men multiple orgasms. What was that experience like?

There are two types of orgasms that happen with male partners. There’s orgasming through ejaculation and penile stimulation, which is great, and there are people who have a shorter refractory period so they’re able to cum over and over.

If I really want to, I can cum four or five times and keep going. Obviously, it takes a long time. That is just the experience of dating someone who [loves semen] and says, “I need all of your cum.” The last few are just little puffs of dust coming out of your dick — the complete draining.

That’s fun when you have someone who can cum and cum again, and get through those refractory periods. I’ve had partners who cum four or five times a night, and that’s great. I love that experience.

The other way is just through anal stimulation through the prostate. I find for men when there’s more anal stimulation, you can get into the orgasm a lot faster, and you can extend the orgasm. It won’t end until you end it, it will keep going like a constant flow orgasm. 

And to be able to get someone into an orgasm for a couple of minutes to finally have that full release, it’s amazing.

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What the Male Orgasm Is Like & How to Intensify It

Source: AskMen