How to Ask for Pegging or Prostate Massage

Do you like the idea of pegging or prostate massages but feel shy to ask your partner?

It can be tough to ask for what we want. You’re not alone in the booty desires struggle! There’s so much stigma that blocks people asking from asking for anal play and pleasure, like:

Society’s ideas about who is the giver and who is the receiver during sex
Internal and external homophobia, e.g. ‘does enjoying pegging make me gay’?
Beliefs about masculinity and how sexuality and masculinity happen, e.g. being penetrated might feel ‘un-masculine’
The bootyhole is also a shithole, so we might feel deviant if we enjoy sexualizing a ‘dirty’ area of our bodies
Fearing being perceived differently by your partner because of your sexual desires
Lack of confidence and communication skills in talking about your fantasies with your partner
Sexual shame from your faith, family or friends

The only thing that these stories are doing is blocking you from the pleasure and intimacy you deserve to have with your own body and with your partners. Anal sex, prostate massage, and pegging are all wildly sexy ways to satisfy your desires, and create a special intimate bond with your partner.

HERE'S WHY PEGGING IS HOT:

Pegging and prostate pleasure engage the erogenous areas in and around the anus - the anus is heavily innervated and designed to feel pleasure (otherwise it wouldn’t feel so good).

Exploring bottoming can be a special way to play with power in your partnership, as well as relax the stressful expectations to always ‘be in control’ during sex.

Prostate massage and pegging creates different experiences of pleasure in the body, and, for some people, can result in different types of orgasm.

Studies have shown that prostate massage can benefit prostate health by promoting blood flow. It’s also been shown to help some folks with ED, pelvic pain, and other challenges.

Pegging and prostate play can add more variety and fun to your sex life!

Engaging in pleasure you enjoy is empowering!

HERE'S HOW TO CONFIDENTLY ASK FOR PEGGING OR PROSTATE MASSAGE IN A NEW RELATIONSHIP:

1. Fantasize about what turns you on about pegging or prostate play

Fantasies are usually not solely about sexual activity. There is a story or a mood that is created by your specific fantasy. Think about how you want to feel during pegging or prostate play. Do you have fantasies of dominance and submission? Do you like the idea of being the receiver and being penetrated?

Be able to talk about your fantasy beyond the sexual activity. Tell your partner what makes you curious about it, why it turns you on and what experience you have with it.

2. Explore your own shame or insecurity about pegging or prostate play

What are you nervous about? Are you concerned about potential mess, pain, discomfort? Do you worry how your partner might perceive you? Do you have thoughts about what pegging or prostate play says about your identity or gender expression?

Getting honest with yourself about any insecurities can help you become more self-aware about your desires and any shame. This will be valuable when communicating with your partner, whether you choose to share what you’re nervous about or not.

3. Play with your own butt first.

You can feel more confident in knowing your own body and anal pleasure if you explore your own body first. Knowing your own body and being able to give feedback to your partner can help them feel more confident too. Want to get started with your own butt play?

Explore in a nice hot relaxing shower, using a well soaped up finger to massage and play with the sensations in your butt
Include some butt play during a masturbation session - lay down a towel, get nice and aroused first, and be sure to use lots of lube
Start externally. Most of the nerve endings in butts are at the opening. Take your time playing here, and, don’t rush yourself into internal play

This is Bubbles, the pegging dildo of my dreams! I co-created the Bubbles Dildo with the wonderful team at Freely Toys. Check out Bubbles pegging-centered design.

4. Ask your partner if they’d be open to talking about sexual fantasies and desires.

It’s ok to be direct and say, “I have a sexy fantasy that turns me on, would you like to hear about it sometime?” You can try communicating over text, during a non-sexy time or a relaxing time.

Having a date night to do sex toy shopping in person or online can be a fun activity to get you both talking about prostate sex toys, dildos and harnesses.

5. Talk about your fantasies without expectation.

While your goal might be to get your partner interested in pegging you or playing with your prostate, talking about your fantasy is also an opportunity to learn about your partner’s likes and dislikes. You might discover another way to turn each other on with or without butt stuff.

6. Do some learning about pegging and prostate massage together.

Learn about pegging skills and prostate pleasure and harness play as well as how to seduce the butt to improve this kind of sex with your partner. Check out my Prostate Pleasure Skills Webinar - it has a body demo and comes with my Prostate Play Guide!

New sexy activities are a skill - they can take time to feel super sexy because you might be in your head about technique. Getting information can help you anticipate challenges, navigate shame and share in the preparation together.

7. Have fun and be playful!

Enjoy the rewards of sexual exploration! Feel more relaxed, more playful, more curious and less performance focused. Exploring a new sexual activity together can deepen intimacy and build excitement between a couple.