Anal August has shown us just how much prostate play can reshape pleasure. For chastity wearers, prostate milking is more than curiosity.
A focused prostate massage can unlock an orgasm that feels entirely different from the quick release most are used to. Instead of staying in one place, the orgasmic sensations build from deep inside and radiate outward, flooding the whole body with rolling waves of pleasure.
For chastity wearers, P-spot stimulation offers release without breaking lock, giving the mind and body a chance to reset while staying in a submissive headspace.
Done right, milking is equal parts technique, patience, and connection. If you are curious how to prostate massage effectively or just want new prostate orgasm tips to add to your routine, these five essentials will help you get started.
1. Build up before the session.
The prostate and seminal vesicles continue producing fluid during arousal. Without ejaculation, that buildup creates the fullness that makes a milking session more intense and effective. How long should you build up before prostate milking? Teasing for a few days before a milking makes the session more productive and the sensations more intense. Edging and denial are perfect preparation, especially while locked.
2. Keep arousal high, but don’t climax.
On the day of milking, cycle up the edge of climax and back down again a handful of times. The more responsive your body is, the easier it becomes to massage fluid out of the prostate. This approach fits naturally into chastity play where stimulation and frustration already go hand in hand.
3. Find the prostate and start slowly.
A well-lubricated finger or a curved sex toy will help you reach the P-spot, a walnut-sized bump just inside the anal canal. Gentle circles and light pressure are best to start. Aneros prostate massagers or smaller wearable plugs from the CB-X Kink Boutique are our top recommendations for P-Spot pleasure seekers. Remember to play safe and always use an anal-approved sex toy with a base.
4. Switch to firmer strokes when ready.
Once arousal is high (like, a 9/10), firmer strokes or steady pressure can trigger release. Just know that milking will not result in the traditional orgasm you’re familiar with, but many wearers find it just as satisfying, if not moreso. Tools like the Lovense Edge 2 and the nJoy Pfun Plug deliver targeted stimulation that makes the process easier and more consistent.
5. Aftercare, always!.
Prostate milking sessions can be draining (pun very intended), both physically and mentally. Afterward, be sure to check in with yourself or your partner. Discuss what felt great, what may have been uncomfortable, and what you want to try next. For some cooling relief post P-Spot play, apply a small amount of Dr. Tush’s After Butt Play to soothe the bum. Keep it in the fridge for added sensory stimulation. A consistent aftercare routine keeps relationship dynamics healthy and makes every session more rewarding.
Adding milking to your chastity routine expands pleasure without breaking out of a cock cage. With the right prep, technique, and prostate toys, it can become one of the most rewarding parts of locked life.
We are calling on the CB-X community to share their prostate play experiences with us.Take our CB-X Anal August Prostate Survey here before it closes at Midnight (PST) this Friday August 22. It takes under 2 minutes and you’ll be entered to win the Playboy Pleasures Bring it On Thrusting Anal Plug with Vibrating Ball Cradle, valued at $119!
Catch up on all Anal August 2025 content below:
CB-X Beginners Guide to Prostate Play
How to Unlock More Intense Chastity O’s
Best Prostate Toys for Chastity in 2025
Cheeky regards,
CB-X
