Open Minded

Part 1

I am a straight, married male who happens to be open minded and I discovered my love for ass and prostate play a long time ago.
I'm actually on my second marriage and between my marriages while I was single, I discovered my love of ass play and prostate stimulation.

About 14 years ago, I went to a massage therapist.
He was a cool guy. We were the same age. He was totally legit. Nothing crazy or sexual involved. Strictly massage therapy. I had been divorced for about six months when I started going to see him. I was experiencing a ton of tension in my lower back and it was probably brought on by the stress of the divorce and other shit that was going on with school and life in general.
So, I start going to this guy regularly to work on my lower back. We would make small talk during the sessions and as he tried to release my lower back of all its tension, he'd make suggestions of different ways I could help myself out between visits to ease the discomfort.
One day, about my 6th or 7th visit, this guy asks me in the middle of my session if I was having sex regularly. We had become pretty good friends and I trusted him. He wasn't weird or creepy. So I answered his question. I told him I hadn't had sex since the divorce, but I had no problem finding release time alone.

He asked me how often I would masturbate.
I proceeded to tell him I was a twice a day kind of guy. Once in the morning as soon as I woke up before I showered, and at the end of the day, usually right before bed. He asked if I was taking time to enjoy it or if I was rushing my way through to simply get off. I told him I always allowed enough time for a great session so that I could really make love to myself.
He asked if he could ask me a serious question. I said sure. He asked me if I had ever experienced prostate massage and stimulation, either with myself or a partner. I told him I hadn't.

He said, "You know, prostate stimulation would really help you out."
"It would really release a lot of tension you're holding. Does that freak you out?"
I told him I wasn't freaked out by the suggestion, but, that I hadn't really considered it. He told me to go online, do some research and think about it. So, naturally I did. This guy never made a move or tried anything with me. He never pushed.

I continued to go to him until he eventually moved and he referred me to another CMT.
The new guy was also really helpful. He had gotten notes from the first therapist and saw that he had recommended prostate massage. About 4 sessions into seeing this guy, he asked me if I had taken the other guys advice in regards to exploring prostate massage. I told him I had.
I told him I'd done research, but never acted on it alone because I found the idea of inserting my finger into my ass to be a bit awkward. I had tried a few times, but found the reaching to be a bit uncomfortable. He asked me if I had a partner I felt comfortable enough with to see if they'd be willing to explore with me. I told him I wasn't in a relationship with anyone and that I didn't really have anyone in my life that I could approach about it.

So, he asked me if I wanted to experience it in the session.