Yes

I slowly and very nervously reached for it. She smiled, not because she was degrading me to do this, at least I didn’t think so. She might, and I hope she was, imagining that I had what it took to do this or at least was willing to try.

I got to it with my right hand, right under her pussy. I realized to get to it, I would have to put my fingers between the end of the plug and her anus. I was going to touch Andrea’s anus and I had to appear confident enough to do so.

“You better appreciate this.” I said trying to sound flippant and lighten the mood.

She smiled and I wondered if the way I had phrased it might have sounded like a dominant person. Like the person she needed me to be. Like I was demanding her to appreciate what I was willing to do for her.

“I do… I promise that I do…” she said sounding choked up.

I gently placed my fingers around the end of the plug and she moaned and shivered as I grazed the skin around her asshole. I could feel sweat and maybe even vaginal secretions, and what I guess was lube. I can’t judge… I need to show I can do this.

I looked up, after the moan, I couldn’t help it, and she was crying. I wanted to rebuff her getting off on this, but I guess it was involuntary. Somehow I knew her tears were tears of joy. Maybe that’s all someone really needs: to be seen for who they really are and still be loved.

I lightly began to tug, and she looked slightly uncomfortable, as I guess one does when having something pulled out of their ass. I imagined this had to hurt, but I guess she may have wanted it to hurt. I watched her asshole stretch and her pussy seemed to leak a little, it took everything in my power to not run or act displeased at that moment. She moaned again and grunted, as it stretched more and more. I had to admit that this was certainly something I never imagined, and I was very much focused on her butthole and don’t think I could look away if I tried.

I very slowly pulled and it had stretched to about two inches wide and I had to imagine this would be awful if it was being done to me. She just kept grunting and didn’t show much pain, she might be used to it. I could tell it was finally coming out as it exited her asshole and started to taper off in width. Her pussy was even more wet than before. I couldn’t help but feel slightly used.

“Tell me you’re not doing this to **** me.”

She pulled her hands to her face and looked upset.

“No, Laura, no I promise. I’m the one who wants to be degraded. I would never **** my domme.”

I was having a full conversation pulling something out of her butt. Still if this was really as bad as it got, I might be able to handle it.

I said “okay.” As I wasn’t sure what else to say, I kept pulling and it finally came out. It went maybe 4 or 5 inches inside her rectum…. And that was something she liked. This is… not how I expected our hangout session to go.

Her asshole looked… open, I guess, under her slit. It was concerning, at least I thought it was.

“Is… is that how it’s supposed to look?”

Trying to sound natural in uncomfortable situations is not a strong suit of mine.

“Gaped? Yeah, it takes a little bit but it will go back to normal.”

I stared a little bit longer and had to ignore wanting to stick my finger there just to see what putting my finger in the emptiness of a “gaped” asshole was like. I didn’t even know they could do that. Fuck, was I supposed to gape her asshole in the future? Well I’ll worry about that later.

I stood and finally took off her collar. I guess that means we’re done. She finally stood and there she was, my very much naked best friend. I could tell what she wasn’t sure what to say or how to feel so I just gave her the biggest hug I could.

“You don’t hate me, right?” She asked nervously.

I rubbed her nude back. I think of all the things I just did, comforting her after was the the thing I enjoyed the most. The only thing I definitely enjoyed.

“I think I’ve made it very obvious I love you.” I said with maybe some light sarcasm.

She leaned into me and I held her for as long as she needed, which was a very long time. I wondered where this journey would take us, but for right now I was content and more importantly she felt accepted and was safe.