I watched Kate’s face anxiously as she contemplated my request. I was relieved as her familiar warm smile appeared and she sat down on the bed next to me and stroked her fingers through my hair.

“Of course I will Andy! I think that would be a good idea and a good learning experience for both of us. You need to empty your bowels first, so go off to the bathroom and I’ll wait here for you. Take a package of these towelettes to clean your bottom up afterwards.”

She handed me a small packet. I put my robe on and marched across the hall to the bathroom. I was thinking that the cleaning instructions she gave me indicated that she had plans to include my bottom. My BM was a quick evacuation because of all of the probing of my rectum. I cleaned myself extra carefully and realized I felt some excitement to be preparing myself for her like this.

When I got back to my room, Kate was still sitting on the edge of the bed waiting for me. She had a new large tube of lubricant with a purple cap on it that she must have fetched while I was in the bathroom.

“Take off your robe and lay down here. Lay on your back for me.”

“Here’s how we are going to go forward, Andy. I think it’s best for me to first put my finger up your bottom again and see how you respond. It’s going to be different this time: not quite so strictly medical. I’m going to do it in a way that I think will help you become aroused and make you feel nice. Then I’m going to have you go ahead and masturbate with my finger up your bottom. That’s going to be a new experience for you! Correct me if I’m wrong, but I bet you have never masturbated with a finger in your rectum, have you?”

I shook my head no.

“Now, lift your hips up so I can put this folded towel under your lower back. We need to raise you up a bit and get you more exposed so that I have good access to your anus. That’s it.”

I rested myself back down and could tell by the cool air around my bottom hole area that Kate’s trick accomplished what she wanted. She then had me spread my legs and draw up my heels so that my knees were up in the air. She spread another towel out on the bedsheet — “Things may get a little messy!” She smiled as she situated it between my splayed legs.

Next she leaned in close between my legs and squinted her eyes to indicate she was carefully inspecting me. “Good! You look nice and clean. Were you able to empty your bowels thoroughly for me?”

I nodded yes.

“Good. That will make things more comfortable physically and mentally for you. I know you tend to get anxious when you feel that “need to poop” rectal urgency. I think you can deal with that more easily if you are confident that your rectum is empty.”

It was unsettling how well Kate had come to know me. She was right. I did find it intensely embarrassing and anxiety provoking when her finger gave me those types of sensations. I wanted to be clean for her and to retain control of my body, but having her finger inside me and producing the sense that I was completely losing control and that she might cause me have a messy accident was overwhelming. And the fact that she knew exactly how this made me feel both physically and emotionally made it all the more so. I could have no secrets from her. No secret parts to my body that she could not access and no secret thoughts or feelings that she did not somehow sense and understand.

It also occurred to me at this point that although the current situation started as a suggestion that I masturbate, and that she might be there with me to watch, it immediately came to include her penetrating my bottom as a major focus. It was a tacit confirmation that Kate considered what she had been doing to me all summer was sexual. There was perhaps some medical and vague “health” goals, but much of that was clearly a pretext for her to get us to the point we were at now. We had become sexual partners.