The ULTIMATE Beginner’s Guide To First Time Pegging

So you want to properly prepare for your first time pegging and avoid the most common mistakes? Let’s get started then…

first time pegging

Here are quick pegging for beginners steps:

  1. Get used to anal penetration – try butt plugs, fingers, small dildos.
  2. Get to know male anatomy and how to find that P-spot – trial and error the same as with G-spot.
  3. Get a good lube, comfortable harness and modestly sized strap on dildo – simpler and smaller is better in beginning.
  4. Learn what you enjoy and test drive toys by yourself.
  5. Talk it out – any potential pitfalls, positions you would want to try, how you would like the pegging to go.
  6. Warm up with smaller toys, spend plenty of time in arousal and be prepared that the first time will be awkward no matter what.
  7. Rinse and repeat. Practices makes comfortable.

This is TL;DR version, but as always the devil is in the details, here are the best tips for beginners mixed with stories from real life:


#1 – Find the Right Pegging toys For You

There is no shortcutting this step – it will take time to find the toys you like.

best strapon for pegging sizes and angles

For him – it’s all about the dildo.

The size, curve, looks of it. Prostate location is little different for each man so just getting several affordable dildos and butt plugs is a way to go.

Get simple non realistic little curved Tantus dildo & harness kit if you’re new.

It’s a combo of vibrations, dildo, and harness for a good price but it’s not the best quality harness.

It will give you a lot better idea of what you like, don’t like so you can make better choice the next time.

Spareparts Joque Harness

For her – it’s about the harness and how comfortable it is. Spareparts Joque is the most comfortable.

As for her pleasure, know that double or strapless strapons are advanced toys that are not advisable for beginners.

Yes, you can add a bullet vibrator, but start with a simple dildo and harness at first.

Read the full guide: Best Pegging Strap On Sex Toys That Actually Work


#2 – Find & Use The Right Lube

sliquid sassy lube

It’s that important. Bad lube will mess up the whole experience. A great lube will make everything better.

Astroglide is awful for most people.

Sliquid Sassy is the most loved water-based lube for pegging enthusiasts.

Many people like to use unrefined coconut oil (just warm it up) as it stays on for a long time and doesn’t dry as fast as water based lube.


#3 – Talk It all Out: Explain How You Want It To Go Down

It’s important to align his and her expectations.

He knows better what he might like – how deep, how hard to go.

Also discuss if you want to go full on power play – dominant / submissive play, or you just want to experience pegging and not mix other things in.

If he doesn’t know what he wants – expect to talk a lot during the first times.

When you’re doing things – ask him:

  • Is this good?
  • Faster? Slower?
  • Deeper?

The key is to ask simple questions that he can answer with yes or no to avoid breaking the groove.

You don’t want to be thinking much during the pegging process, you want to experience it.


#4 – Put Down A Towel To Prevent Anything From Staining The Sheets

While you should take a shower ( with soapy finger) and clean the ass ahead of time (enemas are an option too) , it’s a good idea to prepare for any potential excrements or liquids.

You could either use towel or throwaway baby pads (no need to wash).

Also, Liberator makes a great machine-washable blanket that has a thin plastic sheet inside that will help with any mess from spreading.

It’s not cheap, but a great investment that will ensure that you never need to worry about mess ever again.


#5 – Stop Fantasizing and Just Do It

In the end, you just have to do it. Better prepare that first time will suck and it will be better than expected.

It’s gonna feel weird – for him and her. It’s easier if one of you have done it before.

But thrusting for her won’t feel natural – it’s a new skill!

And exposing his butt to receive a dildo in his ass won’t feel natural to him – it’s a new world.

You can start things slow. Just have a butt plug and ask him to fuck himself in front of you.

See if you can get him to admit that he’s horny (for best results he should abstain for ejaculation for a week).

Prostate is so much more sensitive and easier to find when it’s full.

Then just get strapped up (or ask him to strap you up for extra arousal).

Fuck him first with a butt plug and when time is right ask him if he’s ready to be fucked with a dildo.

Go to town!

If whatever doesn’t work out, take a timeout, talk about it, and try again.

Maybe right away. Maybe week later. It’s all about journey.


To sum it up here are some more first time pegging tips that didn’t justify a separate section:

  • Start with a soft silicone dildo – If you’re going to start with dildos by hand and he isn’t quite used to them yet, stick with a soft silicone rather than a hard plastic. Afterward, let him work out which he likes, it is really just a personal preference. This will prevent the risk of getting pains in spots you never thought you would. If he decides he likes the hard plastic better then so be it, but most men will like softer.
  • Start slow and spend time in warmup – Have him face you so you can see what he likes and doesn’t like. Start with a small dildo first and increase in size as he becomes more comfortable. Communicate, communicate, communicate! It’s like all sex – good foreplay will make it all the better. On penetration, lots of lube and stroke him as you enter. Allow him to adjust to the sensation before progressing. Start with gloved fingers first.
  • Start with him riding you to give him control over the depth of penetration, angle, and speed.
  • Wait for at least 2 hours after the last bowel movement to do any pegging.
  • Locate the prostate by yourself first to know how deep you like it.

And here’s a quick story from 34 old female, let’s call her Kristy on her first time pegging successful experience (to get you winded up):

“I had never been wetter in my entire life. It felt like when you’re a teenager and making out with your crush and you get super wet and swollen? I hadn’t felt that in a while, especially since we have struggled with a DB off and on since we’ve had our two kids.

I casually mentioned prostate play a few months back. He seemed a little leery of anal play but one night during a blow job he lifted his leg up a little bit and things haven’t been the same since.

I was surprised when he showed me the strap and dildo but SO fucking turned on. I got the strap-on on, we were on our knees on the bed making out while our cocks rubbed against each other. Pretty sure I was already dripping at that point.

I keep getting flashbacks this week of his ass, his moaning, the way he looked with his legs on my shoulders as he stroked himself. I’M HOOKED. I want to see him use a stroker or a Fleshlight on himself next time I fuck him this way.

So, guys.. I’m so excited this is a part of our sexual routine now.

P.S. my quads are sore ever since. I give you guys more credit for thrusting than I ever thought, lol. But, every time I get up and feel that ache I think about it!”

Source: Reddit

Why Pegging Feels Amazing For Men & Women (Pegging Story)

For some reason people are still not convinced that pegging feels amazing.

But ask yourself – would people do it otherwise? Hell no!

But here are few reasons why people do it:

  • it’s an opportunity for man to reach prostate orgasm, more intense penile orgasm or even the mythical Super-O (similar to woman’s full body orgasm)
  • role reversal is hot
  • you’re connecting more with your partner especially if you’re telling her to fuck you the way she would want to be fucked
  • for women it’s fun, but then there are also double dildos that can give her pleasure while pegging him at the same time.

And here’s an honest pegging story from 26 year old man, let’s call him Matt:

I’m a mid 20’s male who’s had his fair share along the road of the anal adventure. It all started in college where I live in my fraternity house for 3 years. I did have my fair share of hookups from those days and most encounters were bland sexual experiences. Drunk, sloppy sex with usually nothing remotely interesting in hindsight.

However, Bridget… girl you open my eyes to what prostate play could entail. I had met her a few times and she wasn’t the hottest girl on the planet, but she was flirtatious in ways most women aren’t. Somehow she always knew how to reel me into wanting to fuck her. I lived in a room (yes, a room) with 3 other guys and we spent a handful of very fun nights. She was kinkier than most girls I’d ever been with. Well one night after a house party we went upstairs and she was giving me head and started licking my taint. Noticing I have feeling very aroused from that, suddenly she grabbed my legs, pushed them in the ear, whispered to me “I want you to relax baby”, and started licking my ass. Holy crap it was so hard to prevent myself from moaning audibly loud with my other roommates in the room.

Since then, I’ve ventured down the anal path steadily. I had developed a strong desire to do pegging (taking a strap on as a man) and later after graduation found a craigslist that was seeking a sub to get pegged from two women. I ended up getting in contact with this guy who ultimately directed his subs to peg me in a BDSM encounter. I had always played a “dominant” role in sex, but as someone who lives life with an open mind and doesn’t I was interested in exploring my submissive side. To make a short story short, it was an interesting experience that even though it was quite painful, the feeling of feeling “full” was pretty exhilarating.

Fast forward to more present day and I’ve been with my girlfriend for a few years now. About a year into dating we started doing pegging. I brought it up to her and she was relatively open to the idea. Well now we probably have done it 30-50 times. We still have great amazing normal sex as anything else would, but pegging has opened up an entirely new avenue of sexual pleasure.

Source: Reddit

Yes pegging can hurt and it can feel amazing – it depends from you and your partner.

What I like most about pegging is that you don’t need to be submissive to peg (all that power play).

But the feeling when someone you love gently enters your butt with her dildo is so fucking hot.

It goes from feeling “omg, this is uncomfortable…too big” to “holy shit, i love it”.

Then she can take your penis, lube it up and stroke it while she’s still fucking you.

You’ll experience the strongest orgasms of your life this way. It’s an explosion and if you haven’t tried it – you’re missing out.

And if your woman is anything like mine, she will be super pleased with herself about how good she was at fucking me. Who knows soon you’ll be ready for round #2.


Bringing It All Together

I hope this pegging for beginners guide cleared your confusion and fear around pegging.

Little obstacles you see in your way are nothing compared to the pleasures, fun, and joy you’ll gain.

Try it, there’s nothing to lose.

…and then come here to share your story!

Cheers!

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