My Boyfriend Was Nervous About Getting Pegged
By: Christine Stevens
Tags: Sex, Humor, Sexuality, Relationshps, Dating

My Boyfriend Was Nervous About Getting Pegged

How to introduce prostate play into your sex life

That’s me with my hair dyed blonde taking Aron to the pier and talking to him about his prostate. Photo by Tiko Giorgadze on Unsplash

We were out at a party, each of us mingling with other guests, when I went over to my boyfriend Aron and whispered in his ear, “Tonight’s the night.”

He looked at me nervously. I was pretty sure he knew what I meant, because we had been discussing it. But then I made it quite clear, by adding in a sexy whisper, “Your ass is getting fucked tonight, boy.”

Aron smiled weakly at me. I squeezed his hand and whispered really closely in his ear, “Don’t worry, I’ll be gentle with you.”

Then I breezed away and joined a conversation on the other side of the room.

We had ordered a special curved vibrator for men online that was supposed to stimulate the prostate. Aron was mostly excited by the prospect of multiple orgasms. He was jealous of me having five or six orgasms in a session, while he was limited to just one. I explained to him how a man can keep going while his prostate is being tickled. Also intriguing to Aron was the possibility of reaching an orgasm without his penis being touched. But he was nervous about the ass fucking part of prostate stimulation.

“What if I really like it?” he had asked me. “Will that mean that I’m gay?”

No, it does not mean that you’re gay

If God had not meant for us to play with the prostate during sex, why on earth did he make it feel so good?

I had to explain to Aron that sexual orientation has nothing to do with what feels good. It’s about which gender you are attracted to. So it was quite possible to enjoy having your ass fucked while still being attracted to women.

But it didn’t feel good when the doctor did it!

Every man has had their prostate examined by a doctor, usually a male. The MD will put a latex glove on, and tell the patient to turn around. Then he quickly shoves his finger in and pulls it out as soon as possible. He’s checking for an abnormal or swollen texture.

He’s not trying to arouse the male.

I explained to Aron that this was going to be a lot sexier than getting ass fucked by the doctor. And I promised him that if he wasn’t enjoying it we could stop at any time.

But he was still understandably nervous.

It is a change for the male to be the passive receiver of penetration

Some men might resist being so vulnerable with a woman. I mean, we’ve all heard about the “man box” where men are trained to be tough all the time, and heroic and the boss and so forth. But I explained to Aron that courageousness is one of the man box traits, and what takes more courage than to open your ass to a female? It is a risk to open your mind and explore the other side of things. But we only have one life — isn’t it worth exploring other options?

When a man becomes the passive partner in sex, and the woman takes charge, it’s a psychological transformation for both. I know I feel exhilarated and empowered by the, well, power that is granted me when a man exposes his butt to me. And men, too, feel excited by the loss of control. Life is suddenly less predictable when they aren’t dictating every second of it.

It leads to a more balanced relationship out of the bedroom as well, I have found. A man who is willing to let me fuck his ass is much more likely to stop and ask for directions when he gets us lost on that road trip. In fact, he is much more likely to let me sit in the driver’s seat (I know, even in 2020 some guys refuse to let the woman drive them!).

Why does prostate stimulation cause orgasm?

The prostate produces prostate fluid that is converted into semen. The prostate squeezes tight to releases that fluid during orgasm. This is the feeling a man gets when he is about to ejaculate. But when you cause this contraction by direct stimulation this feeling lasts much longer than the few seconds that it does during “regular” ejaculation. Under stimulation, the contractions can last for a minute or more.

How good can you stand it?

Can you stand to have an orgasm that lasts for a minute or more? I asked Aron. And not only that, how about the fact that if the penis is not involved in the orgasm, there will be no refractory period, and we can start again right away on giving you a second, third, or fourth long and incredibly intense orgasm?

How could a man say no to that?

The penis doesn’t even have to be erect to ejaculate

Men are shocked when during prostate stimulation, they have not achieved an erection, yet suddenly a ton of cum comes shooting out of their limp dicks.

I have found that multiple orgasms are much more likely to occur to a man who does not get erect before cumming. If he gets a hard-on, it’s more likely that he’s going to put his hand on it, and then the genitals are going to get involved.

A hybrid orgasm is also possible

With an erect penis and stimulation of both the penis and the prostate, the orgasm is a combination of prostate and genital induced. This one, unfortunately, is most likely to bring a refractory period, but it will be shorter than the normal one. If you can usually get hard again after an hour, say, you will be able to achieve another erection after half an hour.

But here’s the thing — even if you cum first in the hybrid orgasm, you can continue with the prostate stimulation and have a second, non-genital orgasm. The refractory period only prevents you from becoming hard again — it will not prevent you from ejaculating if your prostate is stimulated.

Where is the dang thing, anyway?

Push your dildo, vibrator or butt toy into the anus and then begin trying to angle it toward the front, where his penis is. Some toys are made with this angle built in — I would recommend starting with those.

You’ll know you’ve hit the sweet spot because he will begin to make sounds of great pleasure. Yes, it is quite a revelation. So then just apply up and down pressure on that spot with your finger or your toy, and soon you will bring him to his first ass-gasm.

Taking my boyfriend’s ass virginity

When we got home from the party I told Aron to take a shower, and I changed into the sexiest French bustier thingie I had, with fishnet stockings and a kind of burlesque dancer look. Aron came out of the bathroom with a towel around his waist.

“Oooh baby, you look nice,” I told him.

“You look nice too,” he said, eyeing me in my sexy outfit. I saw the towel begin to bulge.

“Why don’t you drop that towel and lie face down on that bed right there.”

The towel hit the floor. I was so excited. I was about to take my man’s ass virginity!

There’s a first time for everything

There’s something about first times. I love taking a female’s “lesbian virginity,” that is, being her first time in bed with the same gender. When I touch a woman between her legs who has never been touched by a female before, it’s like taking her to a completely new land, and I go there with her. I mean really, it is like going out the back of the wardrobe into lesbian Narnia. It a break from reality, I guess. I think I’m an escapist at heart. I used to love drugs for that reason. Now I just love sexual adventure. And also writing. Those are the only two escapes from reality for sober me, sob sob.

Anyhow, if you are a woman who is nervous about doing this with your guy, think of it like going through the back of his wardrobe (no pun intended) and into Prostate Narnia.

Prostate Narnia is a very magical place

I like to rub my own clit as I put the vibrator or dildo into my man’s ass. That’s why I don’t like to wear a strap-on — I find that gets in the way of my hand.

What I try to do is to time it so my orgasm comes at the same time as his first, earth-shattering, Narnia explosion.

He will be shocked to see that cum’s shooting out of his un-erect penis. And to see it continue shooting. The ejaculation is not like the ordinary one, in little dribbles. This is more like a fire hose that the fireman dropped and is shooting all over the place, out of control.

As the man begins cumming, I rub myself like mad and I find myself achieving vicariously the same long, intense climax. I sigh as loudly as he sighs — and believe me, you have never heard your man sigh like this. It is pure poetry.

After this intense journey into Narnia, you can just cuddle him and caress him, and listen to him talk about it. Men are very blabby after their first “passive” penetration — it’s like they finally discover the “chatty Cathy” that’s been hiding inside them.

Or you can go again through the wardrobe and go deeper into Narnia. After five or six climaxes things will get positively altered state-like, I assure you.

There’s a reason that C.S. Lewis gave that name to the talking lion who is Narnia’s guardian and savior.

Aslan.

Bet you didn’t know that whole children’s story was about getting fucked in the Aslan, did ya?

Well, now you know.

Use a dab of water-based lube

I put a dab on the vibrator and a dab on my boyfriend's butthole.

“This is gonna be so good, I said. “Are you ready, baby?”

I pushed it in. As my boyfriend started sighing sweetly, I saw the back of this wardrobe/prison/reality begin to open up like a door and we stepped into a magical world.

“My God!” cried Aron.

“That’s right, baby,” I said as the toy hit his gland and the pleasure flooded his brain. “Give me that sweet ass!”