What a Beginner Pegging Session With Me Is Actually Like
Lets jump straight in – Pegging is anal sex where the penetrating partner uses a strap-on dildo. Fucking people with my strap-on is something I do often, both personally and professionally, and something I enjoy quite a lot.
Some of my clients are very experienced at receiving anal stimulation and know exactly what they like.
But many more are beginners, who have experimented with fingers or toys but have never been pegged by another person. Or even people who have never tried anal play at all. Some have fantasised about it for years and finally worked up the courage to ask, others never considered it until they saw it on my service list and thought, well hey, I’ll try anything once!
It is genuinely a delight to be trusted with someone’s first experience of something new. I get excited when people want to explore their bodies, particularly when we’re venturing into territory they’ve previously thought was off-limits.
And butts are FUN to play with. They’re interesting, they’re responsive and I like ‘em. For the person receiving, it is a fantastic opportunity to get curious about sensation and see what feels good for them.
But for something that can be so much fun, pegging carries a surprising amount of emotional baggage.
Why are so many people scared to try pegging?
I recently asked people on my socials what stops them from pursuing pegging when they’re curious about it.
The most common answer was: I’m afraid to ask.
Particularly with current or previous partners.
They worried they would be judged. They worried their partner would look at them differently afterwards. They worried that wanting to be penetrated was too taboo, too feminine, too submissive, or somehow meant something about their sexuality.
So let’s get this out of the way:
Enjoying sensations in your body has nothing to do with your gender or sexual orientation.
Being a man who enjoys anal stimulation doesn’t make you less masculine. Being penetrated doesn’t make you gay. Wanting to occasionally give up control during sex doesn’t mean you secretly want to give up control everywhere else in your life.
Your body doesn’t know which sensations society has arbitrarily assigned to which identities.
Something can just feel good.
Of course, knowing that intellectually doesn’t magically erase decades of cultural baggage.
I understand why telling a partner I want you to fuck me can feel incredibly vulnerable.
Even if you’re not worried about your partner thinking you’re gay (not that there’s anything wrong with that), you might worry about them finding that part of your body repulsive, or worry about not looking as competent as you usually do because you’re trying something new. That’s a whole lot to worry about, and for many people it feels like its just not worth bringing up at all.
Asking a sex worker feels like a safer option for many people, particularly one that is experienced, such as myself.
Asking for pegging feels selfish
There’s another reason many people hesitate to ask for pegging that has nothing to do with embarrassment.
They don’t want to put their partner out.
I see this attitude towards pleasure in many of my clients more generally. They’re extremely comfortable giving someone else pleasure, but asking for something specifically because they want it can feel selfish.
If you’re imagining someone putting on a strap-on and doing something primarily focused on your pleasure, you might wonder:
What’s in it for them?
And the truth is, not everyone is going to be interested in pegging you.
That’s okay. Different people enjoy different things.
Some partners may not experience much direct physical pleasure from wearing a strap-on but enjoy seeing you experience pleasure. Making someone else squirm, moan and lose themselves can be incredibly arousing.
Your pleasure can be part of their pleasure.
It’s also okay for you to want something that is just for you – as long as the other person is willing and consent
But there are people who genuinely enjoy pegging in its own right (me).
I get delicious direct physical pleasure from fucking someone with my strap-on, whether I’m gifted to access to someone’s butt or someone’s pussy. It feels good for me physically, because I am receiving direct clitoral stimulation.
But there’s a catch: I only enjoy it if you do
My enthusiasm for pegging does not mean you should offer me your arse because you think I want it.
That’s a waste of both of our time.
I don’t want to do unenjoyable things to someone’s body.
If something is “for me”, I still want the person whose body I’m interacting with to enjoy what I’m doing.
With anal, this becomes particularly important.
I need information from you.
Your body is constantly giving us feedback about what feels good, what feels intense, whether you’re relaxing and whether we should continue.
If you’re disconnected from those signals, ignoring them, enduring something you dislike, or withholding that information because you’re trying to give me a good time, I lose the information I need to feel confident continuing.
Then instead of enjoying myself, I start thinking:
Are they okay?
Is this actually hurting?
Are they telling me if something doesn’t feel right?
Could I injure them if I continue?
And I’m no longer aroused. I’m worried.
On the other hand, when I know you’re loving what is happening, I can put that concern down.
I can trust your feedback.
I can relax into my own body and my own experience.
And then I can have fun too.
So if the fantasy you’re looking for is genuinely “use my arse for your pleasure even though I don’t enjoy it”, that’s not something I offer.
You can absolutely pretend you don’t enjoy it as part of an agreed BDSM fantasy.
But underneath the roleplay?
I want you to actually be having a good time.
I don’t want you to think I’m gross
Buttholes also come in all sorts of configurations.
Some people have skin tags, old haemorrhoids, extra folds of skin or little lumps and bumps around their anus. If you’ve been worrying that I’m going to inspect your butt and think it looks weird, I promise you I’m considerably less concerned about the aesthetics of your arse than you probably are.
I’m interested in whether everything feels healthy and comfortable enough to play with, not whether your butt looks like a perfectly smooth little peach.
If you have a new or unexplained lump, or something is painful, bleeding, inflamed or otherwise not behaving normally, get it checked by a healthcare professional before we play. But a harmless, familiar bit of extra skin isn’t something you need to be embarrassed about.
Sometimes the scary part isn’t actually the pegging
I often receive requests from people wanting to try pegging for the first time, asking for a 30-minute session.
My answer is always no, it’s just not possible within that timeframe. My minimum is an hour, but I recommend 2 hours, to have the freedom to explore comfortably.
I wonder whether there’s something psychologically reassuring about asking for only 30 minutes.
Maybe there’s an element of:
I’ll try the scary thing. And if it’s horrible, embarrassing, painful or emotionally overwhelming, at least I only have to survive half an hour.
I understand that instinct.
But booking an hour doesn’t mean I’m going to put on my strap-on at minute five and spend the rest of our booking pounding away.
Quite the opposite.
Having enough time means we don’t have to rush.
And not rushing is one of the most important ingredients in enjoyable anal play.
So what actually happens in a beginner pegging session?
One does not simply walk into my room, bend over and get pegged.
I don’t generally offer “just pegging”, except in the case of an ongoing dynamic where we have already gotten to know each other and I’ve become comfortable enough with your communication style. It’s not sexy for me to jump straight to the pegging, I need foreplay first.
Generally, pegging is something we incorporate into a broader experience together.
In an hour-long beginner session, we might spend the first half of our time simply connecting, getting comfortable with each other and enjoying whatever other forms of intimacy we’ve agreed upon, such as making out, sensual touch, oral sex and penetrative sex on me, or exploring various BDSM elements if you’ve booked a Domme session.
We need to get in the mood first.
Only then, can we begin exploring anal play.
And initially, nothing needs to go inside you at all.
We can spend time exploring external sensation and letting you become accustomed to how it feels.
I want to see how your body responds.
More importantly, I want you to notice how your body responds.
There’s no prize for progressing quickly.
If you’re enjoying yourself and want to continue, we can gradually explore penetration, beginning very small and only progressing when your body is comfortable with what we’re already doing.
Eventually, if you’re comfortable and actively want to continue, we can move on to the strap-on.
From there, you might decide a little is a lot, or you might beg me for more, or want a bigger toy. It’s all up to you. Once either of us decides we have had enough – that’s it, we stop engaging in pegging and we move onto something else.
A common preference is to use pegging closer to the end of the session, pegging you while stroking your cock until you cum.
My most common position is to have my lover on their back, with their legs in the air or around me. This tends to feel more intimate as you can see me and touch me as I fuck you. If I’m using a long enough toy, I can lean forward onto you and kiss you as well.
The second most popular position is doggy style, which can be a bit easier or harder logistically depending on your body type and height. Depending on your body type, it might be harder for me to reach your dick in this position, but a lot of people enjoy stroking their own dicks while I fuck them from behind and then cumming onto a towel below them that we prepared earlier.
All of the above are examples, not an itinerary. We might move faster, or slower. We might never get to the strap-on at all.
There is no test to pass.
You don’t have to succeed at pegging
I think this is particularly important for nervous first-timers: You aren’t booking an obligation to successfully get pegged.
You’re booking enough time for us to explore whether you enjoy it.
Maybe we discover you absolutely love it. Or maybe we explore for a while and you decide:
That was interesting. Glad I finally tried it. Probably not something I need to do again.
Maybe five minutes into exploring your butt you decide:
Actually, no. I don’t want this.
These are all successful pegging experiences in my view.
You learned something about yourself.
That’s the point.
You are 100% in control when you’re bottoming
It’s your body, and you are in control of what happens to it, even when I am doing something to it. Our experience progresses according to your desires, limits and boundaries.
This can sound counterintuitive, particularly when pegging is being incorporated into a domination session or a session that is supposed to be about my pleasure, like an Ember’s Choice.
I might be the person physically ‘Doing’, and you might even be specifically interested in a scenario where I am doing whatever I want to you.
But you are ultimately in charge of what I’m allowed to do to you.
You set the parameters.
If you want to experience surrender then let me do whatever I want to you, just tell me where your boundaries are. Within those boundaries, you can give me freedom and access to do what I want.
What if I change my mind halfway through?
Then we stop. That’s it.
You don’t need to provide an explanation.
You don’t need to apologise.
You don’t need to push through another five minutes because you asked for this and now you feel silly changing your mind.
And you definitely don’t need to keep going because you’re worried about disappointing me, or because you think I’m close to orgasm.
Remember: if you’re no longer enjoying it, I’m no longer getting what I enjoy about pegging either.
So you say you’ve had enough.
I stop.
If necessary, we clean up. I’ll quickly check that you’re physically okay.
And then we keep things flowing. I might pull you in for a kiss.
Maybe we move on to something else sexy.
Maybe you’ve had enough intensity and want a cuddle.
Maybe you want a shower.
Maybe you’re still horny as hell and simply want to continue our session without anything else going near your butt.
All great options.
If we’ve booked enough time, we can also take a break and potentially return to pegging later.
Changing your mind is not a problem and it will not harsh the vibe.
Okay, but what if I poop?
Ah.
The other great fear.
Let’s talk about shit.
Any time something goes inside an arse, there is a possibility of encountering poop.
I’m aware of this.
I am not going to suddenly discover midway through our booking that the human gastrointestinal tract exists and recoil from you in horror.
I’m a grown-up and a professional.
Would I prefer not to have a giant poopy mess?
Obviously.
But if we encounter a little bit of shit, I’m not going to shame you about it.
There is, however, an important difference between a little mess and having stool sitting there ready for a bowel movement.
When we begin exploring penetration, I’ll test the waters.
If it’s apparent that there’s poop immediately inside, we don’t continue deeper.
That’s not because I think you’re disgusting.
It’s because pushing stool further back into your body can be uncomfortable or painful, and that’s not the experience I’m trying to provide.
Receiving anal tends to be much more pleasurable when we have a clear runway.
Practicalities: preparing for pegging
The simplest preparation is also the most obvious:
Do a Number 2 beforehand. Like 1-3 hours beforehand, not immediately beforehand.
For many people, that’s enough. Your rectum isn’t full of poop 24/7, and arses are generally considerably cleaner than anxious first-timers imagine.
If you’ve recently had diarrhoea, significant constipation or your digestive system is otherwise unhappy, however, I’d recommend saving receptive anal for another day.
You can also douche beforehand if you’d like some additional reassurance. I usually douche before receiving anal myself.
You don’t need an enormous contraption. A small anal douche bulb is better.
The objective is to gently rinse the lower rectum rather than trying to flush your entire bowel. Use a modest amount of lukewarm water, expel it into the toilet and repeat if necessary until things are reasonably clear.
More douching is not necessarily better.
You don’t need to send large quantities of water high into your bowel. Apart from causing unnecessary irritation, water introduced further up can hang around and make a surprise reappearance later.
Which rather defeats the purpose.
We’re preparing for anal play, not a colonoscopy.
Douching isn’t mandatory.
If you’ve emptied your bowels, you’re feeling well and everything seems clear when we begin exploring, we can continue.
If you’ve never douched and you’d prefer someone to guide you through the process, I can do that too. Because it takes additional time, you’ll need to book at least two hours if you’d like help preparing.
Why I don’t offer 30-minute pegging sessions to new clients
Butts aren’t light switches.
Most need time to become comfortable with penetration, particularly if this is completely new to you. Pegging also involves more preparation, setup and cleanup than many other activities.
Trying to squeeze everything into 30 minutes creates exactly the environment I don’t want:
A reason to rush.
An hour is the minimum, unless we have an ongoing dynamic where I am comfortable with your ability to get fucked in the arse. Come see me for a longer session first and show me what you’re made of, and then if you want to have a regular shorter session with me, more of a wham bam situation, I’m open to discussing that.
If this is your very first time, I strongly recommend 90 minutes.
If you want plenty of time for other pleasures as well as a gradual introduction to pegging, 2+ hours gives us more breathing room.
I would much rather have plenty of time and discover your body was ready surprisingly quickly.
You’re booking an experience with me, and pegging is something we can explore within it.
Maybe that’s a sensual GFE-style session where pegging is simply one part of the sex we’re having.
Maybe it’s an Ember’s Choice experience where you give me room to explore different kinds of pleasure with you.
Maybe you’re under my control in a BDSM session.
Maybe you’re dressed in lingerie while I mercilessly tease you about what a pretty little bottom you’ve become.
Or maybe you thought you’d try pegging, changed your mind, and we ended up having a completely different kind of sex instead.
So fine, no skin off my bones.
Pegging doesn’t need to sit in isolation as this enormous, scary sexual event you have to somehow endure successfully.
It can just be another interesting thing two people explore together.
Can I put it in my mouth?
Yes you can absolutely suck my dick if you want to.
Curious doesn’t mean committed
You are allowed to be curious and nervous at the same time.
You are allowed to have fantasised about pegging for years and still become nervous when you’re finally lying there and it’s actually about to happen.
You’re allowed to have never considered it before reading this and suddenly think:
Actually…
You are allowed to find out if you like something. You’re equally allowed to discover that once was enough.
And you’re allowed to stop without explaining yourself, apologising to me or worrying that you’ve wasted my time.
I don’t need you to arrive already knowing the outcome, that’s what exploring is for.
Pegging is something I do regularly. You’re not strange for wanting it, and you certainly won’t be the first nervous beginner who has walked through my door wondering what on earth they’ve gotten themselves into.
For me, being trusted with someone’s curiosity is part of the joy.
We’ll take our time, we’ll listen to your body, and you remain in control.
And you don’t have to succeed at anything. So if you’ve spent the last five years thinking:
I wonder what that feels like…
You can stop wondering.
Come and find out.
Pegging, femininity, sissification and humiliation
Pegging also appears regularly in my femininity-focused, sissification and humiliation sessions.
Enjoying penetration doesn’t inherently make you feminine, gay, submissive or less of a man. Sexual acts don’t come with a universal meaning.
But they can have whatever meaning you give them. For some people, bottoming is genuinely femininity-affirming. It helps them connect with their femininity, feel softer or more receptive, or simply feel feminine. I think that’s beautiful.
For someone else, pegging might feel submissive, slutty, intimate, vulnerable, masculine, completely genderless, or just physically pleasurable.
Some people have a fantasy that specifically involves being “feminised” through penetration. In a sissification or humiliation session, we can play with that idea, including roleplaying that I’m “forcing” you into becoming my feminine little bottom.
The meaning belongs to you though, you have control of that narrative.
If femininity feels affirming, I’ll celebrate it with you. If it feels deliciously humiliating, we can play with that instead. And if you’re a masculine man who loves getting pegged and doesn’t find it remotely feminine, that’s really hot! Take it like a man!
To me, empowerment isn’t about whether you’re the person penetrating or being penetrated. It’s having enough agency over your own body to pursue what genuinely feels good to you without shame.
There is something deeply freeing about being able to say, this is my body, this is what I enjoy, and I get to choose what I do with it.
The meaning belongs to you.
Whatever story we’re playing with, consent remains real even when we’re roleplaying that it isn’t.
You can read more about my Sissy Humiliation & Power Play sessions, or explore femininity without humiliation through my Feminine Affirmation & Pretty Girl experiences.
Ready to explore?
I would love to hear from you if you would like to explore pegging with me.
Pegging requires a minimum one-hour booking, with 90 minutes recommended for first-timers and two hours recommended if you’d like a particularly unhurried experience or assistance with preparation.
You can add pegging to a Girlfriend Experience or Ember’s Choice session for $100. This fee covers the additional preparation required.
Pegging is also part of my Pornstar Experience (PSE) offering, which is $200 and includes a range of kinky extras.
I require notice, to ensure I have all of my required equipment ready for you.
You don’t need to promise me you’re going to go through with it.
You just need to be curious.