So, You Want to Watch Your Partner Masturbate (But Are Afraid to Ask)

I was surprised to see not one but two comments on my last post asking how to ask a partner to masturbate during sex:

I want to watch my boyfriend masturbate but I am too embarrassed to ask. Any advice?”

– Raquel

How do I ask my partner to masturbate more often? I think she is embarrassed for me to catch her but the site of her using her vibrator completely turns me on. We have never done anything like that so I am unsure how to approach it the first time.”

– Andrew

It’s important to answer these in a detailed yet compassionate manner, because unfortunately many people either live in or were raised in sex-phobic society. At the same time, many also live in a sexually explicit society where sexualized images are everywhere. For an adult in 2021, this can be very confusing! We still seem to be afraid to talk openly about what sex means (vagina, prostate, and all,) but we all want good, loving sex (I think…)

Anyway, this confusion leads to a breakdown in communication between sexual partners, which is a shame. Many people feel terribly uncomfortable to show up in the bedroom with a Giant dildo and say, “surprise honey, I thought we’d try something new today!” But many people also feel uncomfortable in communicating even something relatively tame, like asking to see their partner pleasure himself or herself.

The breakdown in communication about sex can be especially painful between partners, because romantic partners are normally best friends and are highly intimate in other ways. Partners are normally happy to talk about everything and one might expect them to be safe, happy, and excited to talk about sex, too. Luckily, people can practice their compassion, and awareness, and get better at talking about what they want. By practicing a lifestyle of curiosity and compassion, people learn their own special sexy communication styles, and open the door to explore new ways of being erotic.

Here are some DO’s and DON’Ts for any sex-haver who would like to see their partner masturbate, but are afraid to ask:

DO remember that embarrassment, shyness, and general awkwardness is normal during sexual experiences.

DON’T try to avoid feeling shy or embarrassed. I hate to break it to you, buttercup, but having intimate, heart-to-heart, sexy, sex takes bravery and courage, and that’s because intimacy takes vulnerability. And vulnerability feels f*cking weird! Whether you are just beginning your personal sex-having journey, or if you are with a new partner, or you are learning how to communicate your desires: Guess what? You can only get to intimacy by battling a little of that funny-feeling discomfort.

Anxiety, fear, procrastination, embarrassment, shyness – those feelings come when you venture out of your comfort zone – and in this case, that’s a good thing! They are the neon lights that say “Intimacy, This Way!” Intimacy requires vulnerability, and vulnerability requires you to feel uncomfortable. So don’t be scared to feel uncomfortable, because the best part, though, is your partner will be right there with you, and that’s love 🙂

DON’T let feelings of embarrassment, shyness, or awkwardness control your sex life. In this moment, your goal should be to connect with your partner, to cherish your body and your partner’s body, and to build a relationship that has room for true vulnerability and trust. Those are some great intentions, but focusing on feelings like embarrassment is a huge distraction. Young people and even grown adults say things like, “Oh, I’m just awkward,” as if this excused them from not being able to communicate about something as important as a fulfilling row in the hay! If you think like this, I have one things to say: No, no, no – you’re ruining it!

DO be ready to let go of your old identity. Some folks forget that awkwardness is just a stage. As a human being, it is your job to recognize those emotions, feel them out and give them some compassion, and then re-focus on your goal.

Your goal is not to keep being that awkward high-schooler or young adult forever. Your goal is not to be a scared, shy prude forever. Your goal is not to be sexually frustrated forever. Unfortunately, there is a reason that you are that way. And it’s because you are comfortable with that old identity, and one which is now holding you back from your dream. It’s time to say good-bye to that person, if you really want to experience intimacy and a fulfilling sex life.

The bad news is giving up an old identity or lifestyle or way of being, can often rock the boat. It can have some less-than-glamorous consequences, and I won’t say it’s always easy to leave an old identity behind, even if you know it kinda sucks.

The good new is giving up an old identity guarantees that a better one will take its place. When have you ever updated to a higher-end device and regretted it? When have you ever gotten a luxury treatment and thought, “You know I wish I’d had a crappier experience…” Never! The answer is never, guys.

Soon, maybe not tomorrow or next month, but soon, a new identity will take shape – and it will still be you! You’re already good stuff. But it will be a better version of you, one who knows how to relax into the intimacy of being seen as a sexual being.

Enjoying sex and learning how to talk about it will enhance the rest of your life, too. It just becomes part of your existing identity (which I’m sure is awesome!) Goodbye to negativity, hello to a new way of seeing yourself!

Tip: Write positive, sexy affirmations daily in your phone Notes app or in a journal (Example: I am a sexual being and I feel safe and happy now; Why is it so easy for me to have great sex now?; My new erotic identity is good, curious, and fun.)

DO emphasize safe, respectful, voyeurism outside the bedroom. (A voyeur is someone who enjoys watching, by the way.) So many people seem to want a recipe that viola! makes you and your partner feel at ease, and makes y’all equally horny. If it was that simple, you would already be watching your partner masturbate right now. The truth is, getting to a place that is both exciting and safe, takes a good amount of practice outside the bedroom.

Are you surprised? This is why so many people fail to achieve intimacy: they falsely think that intimacy occurs only in the bedroom. If a serious opera singer, musician, painter, pianist, actor, politician, or any serious person whatsoever wanted to accomplish a special and important task, they rehearse the scenario many times before the event itself.

Now I’m not saying you should turn everything into sex – not at all. This is not about intercourse, or even sexual pleasure, but about creating a dynamic. The exchange between the watcher and the one being watched is an interesting one, and it can take many different forms. Most people don’t like being watched, because it makes them feel self-conscious. Therefore, extra care and attention must be shown to the dynamic of voyeurism. It must be cultivated with respect, admiration, and curiosity, and it must be free from any judgement, cruelty, mocking, or malicious intent. It can take time and practice to get the harmony of the voyeur dynamic down, which is why I say to try it outside the bedroom, and let it be about care (don’t focus on sex at this time).

Let me give you an example: you see your partner doing some thing such as arranging some flowers in a vase, or folding laundry, or brushing their hair after your shower. Don’t ask all at once. I think that taking it slow outside of the bedroom is a great way to bring more trust into the bedroom. Let me give you an example: you see your partner doing some thing such as arranging some flowers in a vase, and you gently touch your partner on the arms, and look them in the eye and say something like, “I just love watching you do your thing.”

Important: make sure, in your heart, that this is a moment when you are really seeing your partner as a divine human being, as more than your sexual partner, as more than your lover, but as a genuinely good person that is a gift to the world. Come to them with this generous love in your heart, and in time this will create a watching-and-being-watched dynamic that is safe, loving, and fulfilling. This is when your partner will feel the most safe to do something as vulnerable as masturbate in front of you. 🙂

DO focus on feeling safe. It is your right as a human being, and it is your partner’s right also, to explore sex, free from judgement, shame, or cruelty.

Please note that shame is very different from embarrassment. If you feel shame or ashamed around certain things involving sex, encourage you to examine it and maybe invest in two or three months of therapy just to work out any kinks (no pun intended.) Embarrassment is normal, but shame is unfortunately a common feeling, and can be soothed with feelings of safety and reassurances that both partners are supportive and supported.

To help fuel the knowledge that everyone is still safe, regardless of what happens in the bedroom, you can give your partner a hug and say, “I’m really glad I get to explore my sexuality with you.” Or you can write them a little note or bring them a cupcake and say, “Thanks for helping me explore my sexuality. You’re hot!”

In conclusion, thank you for your questions and keep them coming! I’ll try to answer more questions in a single post next time.



By justpearlythings

I am a writer, a lover, and a believer in the good things in life. I write about mental health and wellness, along with book reviews and fashion opinions. My blog caters to thoughtful, growth-minded women and men, and offers insights and personal challenges that provide a space for relevant, meaningful connection. The World Wide Web is vast, it contains multitudes, and so do we as people. I believe that through self-awareness and honesty, we create a more loving planet for everyone. Feel free to follow this page and share it with friends and family. Love, Pearl

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