Chastity Lifestyle Blog By Experienced Sex Educators

Our second blog installment for Anal August 2025 focuses on the best wearable anal plugs designed for extended wear during chastity play. Our in-house Certified Sex Educator intentionally selected each prostate toy on this list to achieve the trifecta of comfort, safety, and that sweet spot stimulation for a next-level chastity experience.  These plugs are expertly contoured and designed to target the prostate from inside, offering a completely different dimension of pleasure than traditional penis-focused stimulation. Why Combine Prostate Play with Chastity? The Mind-Body Connection. Adding anal play to your chastity routine opens up an entirely new physical and mental dimension unlike familiar penis pleasure. Instead of focusing on what you can't touch, anal play shifts your attention to your anal canal and prostate, creating a powerful psychological shift. Many chastity players find that wearing a butt plug while caged creates the perfect mental conditioning. Your brain becomes accustomed to seeking pleasure from your prostate instead of expecting traditional stimulation like ejaculatory orgasms. Prostate orgasms, often called "Super O's," are full-body experiences that differ completely from ejaculatory orgasms. The angled tips of quality prostate massagers allows for hands-free orgasms because they hit the P-spot precisely. Simple movements like rocking or shifting while wearing them can trigger intense prostate climax without any manual stimulation. The best part? After experiencing prostate-only orgasms while caged, you won't lose your horniness. Unlike traditional ejaculatory orgasms that result in a refractory period, prostate orgasms can maintain the sublime arousal state that makes chastity play so psychologically compelling to begin with.  Without further adieu… Top 5 Wearable Prostate Toys for Chastity  #5 - For the Beginner/Minimalist B-Swish Bfilled Basic Prostate Massager  Perfect for P-spot play newcomers, this beginner-friendly prostate plug features a comfortable size and ergonomic design specifically shaped to target the P-spot. The simple, effective design focuses on comfort and ease of use without overwhelming features. Its smooth silicone construction and manageable dimensions make it ideal for extended wear during chastity sessions, or throughout the day no matter where you are. #4 - The Heavyweight Champion nJoy Pfun Stainless Steel Prostate Plug Crafted from premium stainless steel, this 11-ounce beauty delivers firm, controlled massage directly to the prostate through sheer weight and nJoy’s precision engineering. The substantial heft creates incredible sensations during movement, especially in positions like doggystyle where gravity enhances the experience. The Pfun Plug prods the P-spot with surgical precision that metal enthusiasts absolutely crave, whether manually controlled or activated with your own sphincter muscle contractions #3 - Size Queen Supreme Honey Play Box Pineapple Man Rolling Beads Prostate Massager The Pineapple Man delivers girth and innovative features in one massive package. This extra-large prostate vibrator features rolling beads in the neck that stimulate the sphincter with textured, moving sensations while the curved head hits your P-spot upon entry. Its substantial size ensures you feel super stuffed while the remote control lets you (or your Keyholder) adjust intensity without interruption. The flared base and slender neck keep everything secure during extended sessions, making it perfect for serious size enthusiasts who want hands-free prostate stimulation with serious presence. #2 -  The Ultimate Mmmmultitasker Playboy Pleasures Bring it On Thrusting Anal Plug with Vibrating Ball Cradle This isn't your average prostate toy - it's a multi-tasking marvel that combines thrusting anal vibration with a vibrating ball cradle that wraps around your sack like a gentle hammock. The beaded, multi-speed design delivers targeted prostate stimulation while the "winged" cradle treats your balls (and probably your taint) to synchronized vibrations. This premium toy easily accommodates cock cages, making it perfect for chastity play where you want maximum stimulation without any penis involvement. #1 - The Shape Shifter Aneros PSY Adjustable Prostate Massager Named after the Greek word for butterfly, the Aneros Psy offers completely customizable prostate pleasure through its unique adjustable design. This innovative massager features bendable arms that let you fine-tune insertable length, angle of prostate engagement, and external pressure to create your perfect custom fit. The multi-contoured ribbed body provides stronger stimulation while the flexible tabs enhance responsiveness to your body's movements. For chastity play, this customization means you can dial in the exact sensations that work with your cage and body positioning, creating hands-free Super O's that feel perfectly tailored to your anatomy. Now - we want to state up front that this design IS wearable - however, it is not intended for grinding. Be sure to read the product details for detailed usage instructions. Honorable Mention - Fan Favorite Lovense Edge 2 Vibrating Prostate Massager Adored by the chastity community, the Edge 2 unlocks new dimensions of prostate stimulation with dual motors targeting the internal P-spot and external perineum simultaneously. This hands-free powerhouse is Bluetooth enabled, connecting to the Lovense App for close-range or long-distance control. The adjustable design ensures perfect positioning while powerful vibrations deliver mind-blowing prostate orgasms that the chastity community can't stop raving about. Here is just one glowing user review:  "I'm looking forward to that very thing on my trip next week. Cage(s), two Lovense (Edge and Edge 2), several nights in a hotel alone. Mmmm. 2 weeks edged and built up already so I'll be begging for it." The Ultimate Chastity Experience Awaits The beauty of combining prostate play with chastity goes far beyond the physical sensations (though those are incredible). While your cock cage keeps one pleasure center off-limits, these plugs unlock an entirely different kind of experience. Fair warning: once you experience hands-free Super Orgasms while locked, you might find yourself questioning everything you thought you knew about pleasure.  Your move.

We get tons of questions about prostate play, especially from chastity wearers who've discovered that locked-up pleasure requires some creative problem-solving. This Anal August, we're breaking down everything you need to know about prostate pleasure. Your regular equipment might be out of commission, but your P-spot is ready to step up as the A-player. If you'd rather skip the pep talk and get straight to the butt stuff, browse our curated Anal August 2025 Product Guides to find exactly what you're looking for.  Best Vibrating Prostate Toys for Men Best Non-Vibrating Prostate Toys for Men Pegging Sex Toys for Couples Best Anal Play Toys for Beginners Anal Sex Toys for Sissies Fun and Unique Anal Toys to Putt in Your Butt 1. The Prostate is a Second Pleasure Center (And It’s Way More Powerful Than You Think) Here's something that might blow your mind: the penis glans has around 4,000 highly concentrated nerve endings, making it incredibly sensitive to direct touch. However, the prostate connects to entirely different nerve pathways that can create full-body sensations. What that means: the prostate's connection to the pelvic nerve and hypogastric nerve means it's deeply wired into your body's arousal and orgasm systems in a different way. This creates a fundamentally different type of pleasure. Let that sink in. While penile stimulation is intense and localized, prostate stimulation taps into nerve pathways that can trigger whole-body responses and multiple types of orgasmic sensations. For chastity wearers, this is particularly revolutionary. While traditional penis stimulation might be off-limits, prostate orgasms offer a completely different type of release. Unlike orgasms that typically result in that familiar post-climax crash, prostate orgasms can be multiple, longer-lasting, and won't kill your arousal or submissive energy. Many chastity couples report that prostate play actually enhances their dynamic rather than disrupting it. The locked partner stays engaged, attentive, and eager to please while still experiencing incredible pleasure. It's the best of both worlds: intense satisfaction without losing that focused, submissive headspace that makes chastity play so psychologically compelling. 2. Prostate Orgasms Are Wildly Different Than Traditional Orgasms Here’s the truth that you might not be ready to hear yet: Many men report that once they perfect prostate stimulation, it becomes their preferred method of climax. Male orgasms are often described as more intense, more satisfying, and infinitely more interesting than what they experienced before. If you're expecting prostate orgasms to feel like regular orgasms, prepare to have your expectations completely shattered. Some men describe prostate orgasms as a full-body experience that starts deep in your core and radiates outward. Instead of the quick, intense spike of a traditional orgasm, prostate pleasure builds in waves that can last significantly longer. For couples exploring chastity dynamics, this discovery can be relationship-changing. The locked partner gets to experience incredible pleasure while maintaining that psychological state that makes them attentive and focused on their partner's needs. And – no refractory period means the fun doesn't have to stop. That heightened arousal can continue for hours, or even days. 3. No, You Don’t Need to Be "Into Anal" to Enjoy Prostate Play Here's where we bust the biggest myth about prostate stimulation: you don't need to identify as someone who's "into anal play" to unleash your prostate's pleasure potential. Many men who never considered themselves interested in anal stimulation find that targeted P-Spot massage feels completely different from what they expected. The key difference is intention and technique. Prostate play isn't about penetration for its own sake. It's about accessing a specific area that responds to pressure, vibration, and targeted stimulation. Many prostate toys are designed specifically for this purpose, with ergonomically-curved shapes and targeted vibration patterns that focus on pleasure rather than just penetration. For beginners, focus on external massage before moving to internal stimulation. The prostate can actually be stimulated externally by applying pressure to the perineum (the area between your testicles and anus). This can be a great way to explore these sensations without any penetration at all. Essential Best Practices for Prostate Play Always, always, always mind rule number 1: Invest in proper anal toys. Prostate-specific massagers are designed with the right curves and safety features. Look for toys with flared bases to prevent any unwanted disappearing acts, like the fist-shaped dildon't pictured in an unfortunate X-ray image (photo credit unknown). Try a set of anal beads and work your way up over time.  Never go without lube again! The anal area doesn't self-lubricate, so quality lubricant isn't optional. Silicone-based lubes tend to last longer and provide better cushioning for extended play. However, silicone lube isn't compatible with silicone sex toys, so be sure to use a hybrid lube (water-based + silicone or aloe) if you want the thicker, longer-lasting texture that silicone is known for.  Start slow and communicate constantly. Whether you're flying solo or with a partner, pay attention to your body's responses. What feels good? What doesn't? This type of play requires patience and self-awareness. Don't hold your breath. Seriously - exhale through your mouth for a count of 4-5 during each thrust. Deep exhales help the body relax and loosen up, so focus on your breathing during anal sex to maintain comfort.  Hygiene matters, but don't overthink it. A simple shower and basic cleanliness are usually sufficient. Enemas aren't necessary for most prostate play, especially with smaller toys.  The Bottom Line Do you hear that? Listen closer. It's your prostate, and it's saying "put me in, coach!"  Your prostate has been patiently waiting for an introduction, and Anal August is the perfect reason to finally make its acquaintance. Remember: good things come to those who go deeper. 

Color has been a long-standing language among kinksters for decades. Sometimes subliminal, sometimes more obvious, wearing specific colors in the kink community can speak directly to aspects of one's sexual preferences, desires, and even nuanced power dynamics.

Here are ten ways to cum in a chastity device, straight from the chastity community!