Pegging 101: A Guide To Pegging Anal Sex For Beginner's

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Pegging 101. A guide for beginners

Imagine stepping into a world where the boundaries of bedroom play are pushed to thrilling new heights. Welcome to the exhilarating realm of pegging. A practice that's been whispering its way from under-the-radar to headline-making discussions in bedrooms. Pegging has evolved from a taboo to a celebrated form of sexual exploration.

Yet for many, embarking on this journey for the first time—or even those seasoned explorers seeking deeper understanding—looms a cloud of uncertainty: How does one navigate these uncharted waters? Is it as intimidating as it sounds? And most importantly, where do you start to unravel the complexities and truly make sense of everything? Fear not. By breaking down concepts into manageable pieces and taking things step by step, you'll find that what once seemed like a challenge is actually quite approachable.

    Did You Know?

    Surveys suggest that about 15% of women have used a strap-on dildo to penetrate their male partner, demonstrating that this practice is not uncommon among heterosexual couples​ (Roberts, 2021)​.

    Pegging 101

    Welcome to pegging 101 - class is in session. This guide will teach you what pegging means and how to peg someone (or get pegged). Most importantly, you will learn the tips, tricks, and positions you can use to make pegging a deeply satisfying experience every time.

    The textbook definition of pegging is when a woman wears a strap-on dildo and uses it to penetrate her man anally.

     However, many people don't see the definition of pegging as this specific and narrow:

    • Men and non-binary folks can also peg their partners with a strap-on.
    • We won't be mad if you use a strap-on to penetrate your partner's vagina and call it pegging.

    Of course, you can't really peg yourself. But you can always use a dildo or massage your own prostate with a dildo or other toy like a strap-on.

    A strap-on dildo is a sex toy that comes in two pieces: an insertable dildo and a harness. The harness is worn around the waist like a pair of panties and the dildo fits inside the harness. The dildo is then in the same position on the wearer's body as a penis would be on a man.

    Give him a back-arching orgasm!

    Simply put, many men & women have sensitive butts and enjoy getting anally penetrated. Men have an organ located inside their anus called the prostate, a walnut-sized gland located just below the bladder, which is incredibly sensitive. Anally stimulating their prostate is highly pleasurable for many men. Pegging your man can give him back-arching, toe-curling, screaming orgasms that will keep him sexually addicted to you.

    Diagram of prostate and perineum

    TooTimid Resource: How To Find & Stimulate The Prostate

    Now that you know what pegging means and why it can be a good way to please your man, it's time to learn how to peg your partner in a way that is enjoyable and fun for both of you.

    Did You Know?

    Approximately 10% of men have reported engaging in pegging at some point in their lives. This data highlights the growing openness and exploration of diverse sexual activities among men​ (NSSHB)​.

    First-Time Pegger? Here's What You Need To Know:

    First things first, talk about it (and make sure you have consent before engaging in any sexual activity).

    Introducing the idea of pegging into a relationship can feel like traversing uncharted territory—a mix of excitement and nervousness all rolled into one. 

    It's perfectly normal to feel a bit intimidated by the prospect of suggesting something outside the usual sexual repertoire. However, embracing this conversation is crucial for fostering deeper intimacy and trust between partners. It's about acknowledging mutual desires, curiosities, and being open to exploring new avenues of pleasure together. 

    While it may seem daunting at first, broaching the topic of pegging can ultimately lead to a stronger connection and a more fulfilling sex life, honest communication, and shared exploration.

    You may need to explain what pegging is sexually, why women like pegging, and discuss other aspects of pegging for beginners. If your partner is open to it, make it a fun and exciting experience by educating yourselves on the topic together.

     

    5 Conversation Starters For Introducing This Idea to Your Partner (Steal These!)

    1. "I value our relationship deeply and our open communication. I've been reflecting on our intimacy and wondering if there are any desires or fantasies you haven't shared with me yet that you would be comfortable discussing. Is there anything you'd like to explore together?"

    2. "I admire the trust and connection we share and think exploring new experiences together can strengthen our bond. I've come across the idea of trying different sexual activities, like pegging, and I wanted to gauge your thoughts and feelings on the matter."

    3. "Our relationship means the world to me, and I want us to feel completely comfortable discussing anything, even if it's unconventional. I recently learned about pegging and its potential for enhancing pleasure and intimacy. I'd love to hear your perspective on it."

    4. "I think it's important for me to be open and honest with you about my desires. I've come across the concept of pegging, and while it might seem unconventional, I think exploring it together could deepen our connection. Have you ever heard of it?"

    5. "I've been reflecting on our sexual journey together and thinking about ways we can continue to grow and explore. I've heard about pegging as a way to break free from traditional roles in the bedroom, and I'm curious about your thoughts on the idea. Would you be open to discussing it?"

    Lube Is Your Best Friend, Always

    Proper anal preparation is crucial for a pleasurable pegging experience. This means ensuring the receiving partner's anus is clean and relaxed. Taking a shower beforehand and maybe even using an anal douche can help with cleanliness and comfort.

    Lube is your best friend when it comes to pegging. Unlike the vagina, the anus does not self-lubricate. So using plenty of good quality, body-safe lube is essential to prevent discomfort or tearing. Water-based lubes are typically recommended as they are safe to use with all sex toy materials.

    If you're not utilizing a silicone toy, you may opt for a silicone-based lubricant. They're longer-lasting and provide a smooth, slick glide.

    Start With A Finger or Small Anal Toy

    If you or your partner are new to anal play, it's best to start with something small like a finger, an anal training set, or a smaller, slim butt plug before graduating to a strap-on dildo. This allows the muscles around the anus to get used to the sensation of being penetrated and helps you get comfortable with the sensation.

    Once you feel ready for a strap-on, choose a dildo that is slim and not too long. Work your way up later as you get more comfortable with the experience. Remember, pegging should never be painful - if it hurts, stop and reassess.

    Did You Know?

    Pegging has been named one of the top sexual trends of the year, signifying a cultural shift towards accepting and normalizing diverse sexual activities​ (NSSHB)​.

    Talk Dirty & Make The Experience 10x Hotter

    Role play and dirty talk can take your pegging experience to a whole new level of intimacy and pleasure. It's a great way to explore fantasies and get into the right headspace for an amazing session.

    Pretending you're in a different scenario or setting is a fun idea. Dirty talk is another powerful tool. Hearing your partner say dirty things can be such a turn-on. Describe what you want to do to them, how good they feel, and how much you love pegging them. Combine dirty talk with other techniques like reach-arounds, light BDSM, and changing up your strokes. It creates a multi-sensory experience that's off the charts.

    Finding The Perfect Dildo

    With so many strap-on dildos on the market, it can be overwhelming to pick the perfect one. But don't worry, we've got you covered.

    • If you're a beginner: Look for something around 1-1.25 inches in diameter and 5-6 inches in length. This will help you get used to the sensation without feeling overwhelmed.

    • If you're more experienced: Size up to larger dildos for a more filling sensation. Some people enjoy textured dildos with ridges or bumps for extra stimulation.

    Material Safety and Comfort - Your Booty Will Thank You!

    When it comes to choosing a strap-on dildo, material safety and comfort are key. You want a toy that feels good and won't cause any irritation or allergic reactions.

    Silicone is one of the best materials for dildos. It's non-porous, body-safe, and easy to clean. Plus, it has a smooth, silky texture that feels amazing.

    Avoid jelly rubber, PVC, or toys with phthalates. These materials are porous and can harbor bacteria.

    It's worth investing in a high-quality, body-safe dildo.

    Pegging Essentials: Harness or strap-on, dildo, lube, and sex toy cleaner.

    Mind-Blowing Orgasms Are On The Horizon

    The key to a great pegging session is making sure both the giver and receiver feel amazing. Communication is everything. Talk openly about your desires, fears, and boundaries.

    Start slow, use plenty of lube, and listen to your partner's cues. If they want you to go faster, slower, deeper, or change angles, trust that they know their body best.

    For the receiving partner, don't be afraid to touch yourself or use a vibrator during the session. This can help you relax and increase your pleasure.

    For the giving partner, you can use a double-ended dildo so you get some internal stimulation too. You can also try grinding against the strap-on base for clitoral pleasure.

    With open communication, trust, and a focus on mutual pleasure, you can overcome any pegging concerns and have mind-blowing, intimate experiences together.

    4 Advanced Techniques To Blow Them Away

    So you've mastered the basics of pegging and you're ready to take your sessions to the next level. Well, buckle up, because we're about to dive into some advanced techniques that will blow your mind (and your partner's).

    1. Get Handsy

    First up, let's talk about incorporating hand jobs into your pegging routine. While the strap-on is doing its thing, you can use your hands to stroke and caress your partner's penis, adding an extra layer of stimulation.

    2. Add A Cock Ring

    Play around with how you hold things, adjust the force you use, and switch up your pace until you hit upon what truly works for you. You can even use a vibrating cock ring or masturbation sleeve to kick things up a notch.

    3. Try A Prostate Massager

    Another advanced technique to try is targeting the prostate more directly. The prostate is a walnut-sized gland located about 2-3 inches inside the rectum, towards the belly button.

    When you get it going, expect to experience intense pleasure that can wash over your entire body. To find it, try curling your finger in a "come hither" motion or using a prostate massager specifically designed for the job.

    Once you've located the prostate, experiment with different strokes, pressures, and angles to see what feels best for your partner. Some men prefer a gentle, consistent pressure, while others like a more vigorous, pulsing sensation.

    4. Incorporate Oral Sex

    If you really want to blow your partner's mind, try incorporating oral sex into your pegging session. While they're being penetrated from behind, you can use your mouth to stimulate their penis, testicles, or other erogenous zones.

    The combination of sensations can be absolutely mind-blowing. Just be sure to communicate with your partner and establish a safe word in case things get too intense.

    Of course, no matter what advanced techniques you try, the most important thing is to prioritize safety, communication, and consent. Always use plenty of lube, go slowly, and check in with your partner regularly to make sure they're comfortable and enjoying themselves.

    With the right preparation and mindset, pegging should be a safe, healthy, and incredibly pleasurable activity for everyone involved.

    So go forth and peg - just remember to wash your hands (and your toys) when you're done.

    The Psychological Dynamics of Pegging

    Pegging isn't just a physical act. It's a deeply psychological experience that can have a profound impact on the power dynamics in a relationship.

    For many couples, the appeal of pegging lies in the way it flips traditional gender roles and expectations. The woman takes on a more dominant, traditionally "masculine" role as the penetrator, while the man assumes a more submissive, receptive position.

    This reversal of typical power dynamics can be incredibly erotic and liberating for both partners. It allows them to explore new aspects of their sexuality and experience pleasure in ways they may never have considered before.

    For guys, letting someone else be in charge during those moments can open you up, making things both incredibly personal and a bit nerve-wracking. It requires a great deal of trust and communication with their partner.

    Many men find that surrendering control and allowing themselves to be vulnerable in this way can be a deep bonding experience that brings them closer to their partner.

    Women, on the other hand, often report feeling empowered and confident when taking on the dominant role in pegging. It can be a thrilling experience to be the one in control, driving their partner's pleasure.

    Pegging opens up a new avenue for couples curious about BDSM and power dynamics, offering them a playground to safely and consensually explore these themes together. The act of penetration itself is a powerful symbol of dominance and submission.

    When couples dive into pegging, it opens up a whole new role reversal experience, switching up who's in charge and who lets go—all while discovering what lights their fire from every angle.

    Did You Know?

    Around 20% of men have expressed an interest in pegging, indicating a curiosity and potential openness to trying this form of sexual play​ (NSSHB)​.

    Breaking Anal Play Taboos

    One of the most significant psychological benefits of pegging is the way it can help break down taboos and stigmas around anal play.

    In our society, there's still a lot of shame and secrecy surrounding anal sex, especially for men.

    By exploring pegging together, couples can break down those outdated views and show that anal enjoyment is a perfectly normal and positive aspect of sexual exploration. They can learn to view the anus as just another erogenous zone, no different from the penis or clitoris.

    This shift in perspective can be incredibly freeing and empowering. It allows people to let go of shame and embrace their desires without judgment or fear.

    Pegging can also help men become more comfortable with their bodies and sexuality. By experiencing the pleasure of prostate stimulation, they may become more open to exploring other forms of anal play, either alone or with a partner.

    This can lead to a more satisfying and diverse sex life overall, as well as greater self-acceptance and confidence. In the end, the psychological power of pegging lies in its ability to challenge norms, break down barriers, and create deeper intimacy between partners.

    By exploring this taboo act together, couples can learn to communicate more openly, trust more deeply, and love more fearlessly, both in and out of the bedroom.

    4 Hot Positions For A Better Peg

    Once you get comfortable with pegging, there are many different positions you can try to enhance the experience. Some allow for deeper penetration, some are great for intimacy, and others provide amazing prostate stimulation. Here are a few pegging positions to explore:

    Pegging Position #1. Doggy Style (Best For Deep Penetration):

    The receiving partner is on their hands and knees while the giving partner kneels or stands behind them. 

    Image of cartoon figures in a pegging doggy position

     

    Pegging Position #2. Missionary (Best For Eye Contact & Intimacy):

    The receiving partner lies on their back with their legs up while the giver kneels between their legs.

    Image of cartoon figures in a missionary position

    Pegging Position #3. Cowgirl/Cowboy (Best For More Control - Depth, Speed, & Angle):

    The receiver straddles the giver and rides the strap-on dildo. 
    Image of cartoon figures in the cowgirl position

    Pegging Position #4. Spooning (Best For Slow, Sensual Pegging): 

    Both partners lie on their sides, the receiver in front.

      Image of cartoon figures in a spooning position

      Positions that allow the dildo to curve slightly towards the belly tend to be best for prostate stimulation. Slow, firm pressure and a rocking motion rather than rapid thrusting usually work best.

      If you and your partner have a significant height difference, some positions like doggy style may need to be modified for comfort. Using furniture like a bed or couch for support can help. Keep pillows close! Use them under the knees, hips, or stomach to adjust angles.

      The key is to communicate and experiment until you find what works best for your body. Encourage the receiver to give feedback on what feels good. And remember that many people require some form of penile stimulation as well to reach orgasm from pegging. Adding a hand job or a vibrating cock ring into the mix can take things to the next level.

      Conclusion - Creating Sex Magic Through Pegging

      So, we've danced around the edges of pegging, peeling back layers to reveal not just a sexual act but an exploration into intimacy, trust, and pleasure. It's far from the shadowy taboo it once was; instead, it emerges as a beacon for those daring enough to step out of conventional roles and redefine what connection means.

      Pegging isn't just about trying something new in the bedroom—it's about breaking down walls that confine our desires. It’s about speaking up for what feels good and finding joy in giving and receiving with openness. From selecting the right tools like body-safe strap-ons to mastering positions that hit all the right spots—every detail matters.

      And let’s not forget—the power dynamics at play can turn traditional norms on their head or simply add another layer of excitement. Whether you're whispering dirty talk or navigating psychological dynamics together, pegging offers a canvas broad enough for every stroke of creativity your relationship wishes to paint.

      The real magic? Discovering that fears like pain during anal penetration are but myths waiting to be busted wide open with patience, lube, and communication. The journey might start with curiosity but will lead you down paths lined with understanding.

      To Peg Or Not To Peg?

      Pegging Anal Sex FAQ's answered

      Pegging is a sexual practice where a person (typically a woman) uses a strap-on dildo to penetrate their partner (typically a man) anally. It can be a pleasurable and intimate experience for both partners.

      Yes, pegging can be safe when done correctly. It's important to use plenty of lubrication, go slowly, and communicate openly with your partner. Using a condom on the strap-on can also enhance safety and hygiene.

      Approach the conversation with openness and without pressure. Explain why you're interested and how you think it could benefit your relationship. Listen to your partner's feelings and concerns, and make sure both of you are comfortable with the idea. P.S. Check out our conversation starters above!

      Water-based or silicone-based lubricants are ideal for pegging. Silicone-based lube lasts longer and can be less sticky, but it should not be used with silicone toys. Always use plenty of lube to reduce friction and increase comfort.

      For beginners, a harness that fits comfortably and securely is crucial. Start with a smaller, slim dildo to ease into the experience. As you become more comfortable, you can explore different sizes and shapes.

      Pegging should not hurt if done correctly. It's important to go slow, use plenty of lubrication, and listen to your body. Any pain is a signal to stop and adjust. Discomfort is normal at first, but it should not be painful.

      Yes, pegging can be highly pleasurable for the person being penetrated. The anus has many nerve endings, and the prostate (in men) can be stimulated, which can lead to intense orgasms.

      Preparation includes both physical and mental aspects. Physically, cleaning the anal area is important, and this can be done with a shower or enema if desired. Mentally, both partners should be relaxed, comfortable, and ready to communicate throughout the experience.

      Pegging can bring couples closer by enhancing trust and communication. It can be an empowering experience and add variety to your sexual relationship. However, it's important to ensure both partners feel comfortable and respected throughout the process.

      References:

      Graveris, D. (2024, January 21). Pegging Facts & Statistics [2024]: How Common Is Pegging? SexualAlpha. Retrieved May 22, 2024, from https://sexualalpha.com/how-common-is-pegging/

      Iovine, A. (2022, December 19). Pegging named 2023's fetish of the year. Mashable. Retrieved May 22, 2024, from https://mashable.com/article/pegging-fetish-of-the-year

      NSSHB (n.d.). National Survey of Sexual Health and Behavior. Indiana University Bloomington. Retrieved May 22, 2024, from https://nationalsexstudy.indiana.edu/

      Roberts, H., Clark, A., Sherman, C., Heitzeg, M., & Hicks, B. (2021, August 6). Age, sex, and other demographic trends in sexual behavior in the United States: Initial findings of the sexual behaviors, internet use, and psychological adjustment survey. PLOS ONE. Retrieved May 22, 2024, from https://journals.plos.org/plosone/article?id=10.1371/journal.pone.0255371


        3 comments


        • Nellie

          When discussing lube for backdoor entry, why does no one ever discuss the potential downside of glycerin? It’s a stimulant for the area, and glycerin suppositories for constipation are (or were) widely available. Probably not anymore, because they work. In my experience using lube containing glycerin is an invitation to disaster, especially if used on butt plugs for extended wear. I understand the allure of silicone toys, but if the TPC/TPS/ABS/whatever it’s made out of bothers you there’s a condom for that.


        • Troy

          I love pegging. I also love being sissified with my heels on while being pegged.


        • David

          Ilove being pegged. My second wife thought it was bad tell she tried anal. Then she pegged me one night and after that anytime I wanted it she gave to me and it does feel so good. Use toys all the time.


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