Bend Over Boyfriend: Pegging, Prostate Massage and Strap-on Play

The biggest myth about anal penetration is that it will hurt. The one thing I tell my submissives: I may make your bottom red and sting from flogging but your ass should never be in pain from pegging and anal penetration. If it does hurt, say your ‘safe word’ and have me back off or stop. You don’t want to risk getting a fissure or a tear up in there, this is why numbing cream is a terrible idea. If your partner or domme wants to fuck your ass so bad that s/he can’t take the time to warm you up, find someone else to play with.

The slippery slope: lube lube and more lube

Your anus is dry as the Sahara, it doesn’t get juicy like a ripe pussy when aroused.

Pulling and tearing is no fun, so you can’t overdo lube. I like Astroglide’s Diamond silicone lube as it’s really thick, stays put on toys and creates a cushion. I also like Swiss Navy silicone lube as it’s fun to drizzle it down an ass crack and mix it up with some spit. Water based lubes can be mixed with silicone but I don’t recommend water-based lube alone as it tends to dry out quickly. Coconut oil is great too (it’s healthy for your body inside and out) but it stains sheets and it’s harder to clean up.

I start with a gloved finger- I like black nitrile gloves as they are compatible for people with allergies to latex, they don’t smell like latex and black gloves looks fabulous with my black sheer stockings ; ) Play with the outside of the ring of the anus; there’s lot of nerve endings there. I like to make circles, then I bring two fingers inside half an inches and make a paddling motion. I push gently with one finger as if I was ringing a doorbell to be let in. Be patient, the door will open when it’s ready. I coach my submissives to take deep breaths (we tend to clench when we’re nervous and even when we’re turned on.) I keep gentle pressure and keep ringing the doorbell, eventually I'm let in. If my submissive is on his back, I bring my finger to curl downward to reach the prostate.

Strap Ons, Dildos and Vibrators, Oh My

My fingers are small so it's one of the reasons I love my little guy and he’s also my “warm up” act. I also like to use a smooth glass dildo with a curve to reach the prostate, and it’s a very different sensation from the soft silicone dildos. I warm it up in hot water before a session as glass tends to be cold and I don’t want Mr Asshole to close the door on me. If my sub feels warmed up and his ass feels ready for more, that’s when I strap on my harness and my big boy, the P-Spot dildo comes out to play. I love this toy as it’s curved for intense prostate play and it has a bullet vibrator inside that I can control the intensity. The vibrator sits in front of my clit as I thrust. Win/win!

If you buy your own toys, avoid the cheap knock offs found on Amazon. You’re putting this inside your body; make sure it’s body safe and not made with plastic phalates (many companies whose products are made in China have claimed their toys are safe but have found to have phthalates and other ingredients linked to cancer.) I like the toys from Tantus and Aneros and prefer their high-quality, 100% silicone (higher quality silicone can be used with silicone lube.) They are soft, non-porous and easy to clean— you can bleach and even boil the toys (no more than 10 minutes) to disinfect them. My friend Ruby Ryder puts her in the washing machine! Just be careful to not throw them in the dryer or you'll have some sad looking melted cocks. Glass is really easy to clean and I like to mix up the sensations (that’s what my Sensual Sensation Play sessions are all about.)

Read about how to prepare for anal play and a strap-on session.