Sometimes you have to try something totally different.
Introducing Anal Massage to a Couple
Then I asked them if they had ever considered anal sex. They said no, but they were open to it.
I had her flip over to her stomach and began massaging her glutes and sit bones. I explained to him all that I was doing.
Exploring External Anal Stimulation
Using lots of lube, I began to massage the crack of her ass. Very slowly. I told her before every change in stimulation I made.
I went from that to direct pressure onto her anus. Using my three fingers together, I placed them broadly against her anus and pressed them into her body.
Slowly, I increased the pressure until it was firm. I checked with her all the time to make sure it was feeling good. She enjoyed all the external stimulation.
I moved on, slowly, using one fingertip to massage her external sphincter. Just dipping the tip of my finger into her anus, I gently applied pressure. Up, to the right, down, and to the left.
At each point, I checked to see if she felt pain. I also explained to her boyfriend what I was doing.
Learning About Internal Sensations
Since everything was feeling good, I sunk my finger in a bit deeper so I was penetrating her inner sphincter. I repeated the pressure in four different directions.
At this point, she wasn’t feeling pleasure, just pressure. I explained that was fine. It could take some time to become used to this type of stimulation and allow it to become erotic.
I slowly began sliding my finger in and out of her anus. I kept my finger straight and didn’t apply pressure in any direction.
Eventually, she was able to take my entire finger into her anus without discomfort of any kind.
I told them they would most likely be having anal sex before vaginal sex since she wasn’t feeling pain in this area.
I gently bent my finger, aiming my fingertip toward her pubic bone. For the first time, she felt the pleasure of pressure against her G-spot.
At the same time, she felt like she might have to have a bowel movement.
I reassured her that there was no fecal matter in her rectum. I explained that she associated pressure in this area with needing to go to the bathroom. With practice, that physical signal might change.
Helping Her Partner Learn
Her boyfriend wanted to try, so I moved, and he sat where I had been between her knees.
I coached him to go slower and slower. He did and was so pleased when he was able to penetrate his girlfriend without bringing her pain.
He began sliding his finger in and out of her anus. As he got more excited, he began to speed up, and she asked him to stop.
He did, and I explained that the tissue is very sensitive and this was a new type of stimulation.
Over time, he might be able to “finger fuck” her and even add a second finger, depending on her comfort and desire.
I told him that one sign she might be ready for anal sex would be when he could smoothly slide two fingers in and out of her anus without causing discomfort.
Communication, Comfort, and Consent
We mutually decided she felt done, and it was his turn to work with me.
A note about anal massage: Anal exploration should always involve ongoing consent, plenty of appropriate lubricant, and communication about comfort. Stop if there is pain or burning. Being comfortable with one or two fingers does not automatically mean someone is ready for penetrative anal sex. Readiness depends on each person’s comfort, desire, and consent.
For more information about exploring different sensations, read my article on sensation play for beginners.
You can also explore my guide on how to give a prostate massage for another perspective on anal massage and stimulation.
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