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Where to begin? Oh, my.
My wife is very willing to provide any kind of anal play on my bottom.
I begin on my back, knees up, sometimes with a pillow or wedge under my bottom/hips. My wife starts out by inserting the index finger of her right hand and then massages my prostate and reaches everywhere inside to touch the top, bottom, and sides of my rectum. Meanwhile, using her left hand, she fondles my cojones and my winkie, but most of the action is inside.
After a minute or two, she adds her middle finger alongside her index finger on her right hand and repeats her internal ministrations. Then she inserts a third finger, but this is only to stretch the anus and not to massage the prostate. She adds a fourth finger with all four fingers pointed together and her thumb folded in below the fingers. She gently twists and turns her hand and applies gentle, constant, increasing pressure until there is a slight "pop" and her hand/fist is completely and fully inside my rectum. With the knuckle on her thumb she can gently massage my prostate. I clamp down and release and push out a little and repeat this a few times. She doesn't withdraw, but pushes in a litlte and pulls out a little. Sometimes, I roll on my side with my knees together just for a different feel and sometimes I roll more to get on all fours, again, just for a different feel. Back on my back, I push and she pulls and her hand slips out of my rectum.
Now begins the march of the toys that, for the last 15 minutes, have been warmed up between two hot pads, for my rectal pleasure. Sometimes she asks which toy I want her to insert and sometimes she just surprises me. We have quite an assortment of toys in a variety of lengths, girths, sizes, shapes, and colors with a variety of lumps, bumps, bulging veins, twists, vibrations, thrusts, and more. She usually inserts one at a time and pushes and pulls for my enjoyment. Sometimes she inserts one of her old vibrating dildos that she no longer uses and with her fingers pushes it entirely up and inside so she can then partial insert an additional thrusting, vibrating dildo behind it. Mind you, the dildo that goes all the way inside has a ribbon attached so she can pull it out instead of having an ER doctor extract the dildo.
With all the different toys and her creativity, I don't think she has ever repeated the same procedure. I like variety and she definitely provides the variety.
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My playing with my wife's bottom is much more limited. I can insert a finger into her bottom and poke around to my heart's content. My wife is not into anal play for herself, but she knows that I love putting my finger in her bottom hole and it is often the button I need to push to get me over the top. And because she loves me and wants to pleasure me, she is happy to have me probe her rectum with my finger.
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