I'm a big fan of anal play as an enhancement for masturbation pleasure. Both my partner and I enjoy anal play and use it quite often when we masturbate.
My partner favors toys, rather than her fingers, when she masturbates. She uses a cock-size (6' long, 1.5' diameter) soft jelly dildo as her masturbation play toy, and uses it to simulate being fucked. Her favorite position is lying on her stomach with the dildo in her pussy. She reaches under her tummy to manipulate the dildo in and out. The speed of her thrusts increases as she approaches orgasm.
Her next favorite masturbation position is to kneel in a nearly sitting position and insert the dildo into her pussy. One hand holds the dildo in place while she rides it up and down.
She enjoys having me spank her while she's getting off. She prefers my hand rather than a paddle. I let her get started and then begin spanking her some time afterwards. She knows I'm going to spank her but she doesn't know when I'll begin, so the 'surprise' element adds to her enjoyment. I start with soft pats and then let her guide me with regards to the intensity and speed of spanking. Her moans and body movements are reliable guides.
Spanking her when she's in her favorite lying on her stomach position is easy. She's prone and her bottom is an ready target. She will stop thrusting a few times to fully experience her bottom being paddled. She is humping pretty rapidly by the time she reaches orgasm and her bottom is getting red at the same time. Her body becomes rigid as she begins to cum and her moans turn to a loud, sustained growl. At this point, she wants me to stop spanking her and to keep my hand touching her bottom until her orgasm is over.
Spanking her when she's riding her dildo is more of a challenge. She's thrusting up and down and is a moving target. I give her bottom a whack when she's in the 'down' position. She will stop thrusting for a while, and sit on the dildo, while I give her bottom a good working over. Her moans turn to groans during this time, and after this, she renews her thrusting with vigor. Like with the stomach position, she wants me to increase my spanking until she begins to cum and then to hold my hand against her bottom until her orgasm is over.
While I enjoy anal play on myself, spanking doesn't do much for me. Instead, when I'm masturbating, I like her to fuck my ass using her dildo (covered with a condom). When we are doing 'anal play', I will either stand or kneel so she has free access to my ass. Just before I begin masturbating, she lubes the dildo, inserts it into my ass in a slow and sensuous way, and starts to fuck me using slow and deep strokes. This brings on a roaring erection, and I begin stroking my cock, timed with her strokes.
The simultaneous feeling of my hand stroking my cock and her 'cock' fucking my ass is incredibly erotic. We both stroke slowly so that the experience is maintained as long as possible. As I get closer to cumming, my moans turn to loud gasps and we both increase our stroking speed. I am so turned on at this point that loads of juice spurt out of my cock. She continues pumping me while I'm ejaculating, and then slows down and holds the cock deep inside of me until I stop spasming.
Anal play is a definite enhancement to masturbation.