Can't buy sweet lovin' from Monica (Femdom Route)

This is the main Femdom Route of the story. This is how I originally planned for the story to go and it currently has the most content prepared. For those interested I have also started a more vanilla route.

The story is now Moderated! So feel free to add your own content (after reading the Guidelines)!

It wasn't long before I heard the door open again.

"You in here?"

I opened the door to let her in and stepped back. Monica closed the door behind her and leaned against it. "So, you want me to go easy on you huh?"

"I just don't wanna screw it up, Lily is amazing."

Monica stepped up close to me and put her hand on my crotch. "Fine, I'll make you a deal. I won't make you cum too early, but I will challenge you in other ways." And her hand squeezed my balls just enough to hurt. "Don't think you are getting off easy, I would be surprised if you make it through the evening without begging me to stop."

"I'll take it I guess, thanks."

She laughed. "Don't thank me yet." She pulled down my zipper. "Now turn around and bent over."

"I guess we're starting right now..." I did as she told me to.

"Oh yes, I think you've had enough of a break. Can't let you stay soft for too long now can we?" She pulled down my pants. "Besides, I thought I would give you a taste while you can still back down." She gave my ass a hard slap, leaving a stinging sensation. "Now hold still, this might be a little cold."

"Cold?" I tried to look back to see what she was doing.

"I told you to hold still!" And I felt another smack. Monica had some surprising strength in her.

I looked in front of me again and steeled myself for whatever was about to happen.

I felt her spread my cheeks, holding them open with one hand. Then something cold touched my butthole, making me flinch.

"Do I need to spank you again, or are you going to take it like a good little slut?"

I retook my position, as I tried not to let her words get to me.

Again she pulled my cheeks apart, giving her access to my hole. I held my pose as the chilling sensation returned. She put a little more pressure and I now recognized it was her finger trying to enter me. Pushing just a little harder, her first digit slit in. "Ahhh" I couldn't help but moan.

She kept going, pulling back just a bit, before trying to **** her way deeper.

It hurt a bit, but the lube helped it go in smoother as she went back and forth a few times. Then she found what she was looking for. I felt a strange but pleasurable sensation as she touched a specific spot.

"Feel that? That's your prostate or p-spot. Thought I might as well teach you something while I'm in here." She emphasized her sentence with another deep push inside. "You might enjoy exploring that later. You're better suited for getting fucked, than fucking anyway."

Her finger left my ass and I started to turn around. Smack! "Back in your place slut."

"Fuck you"

"Yeah yeah, don't tell me you're not enjoying this. I can see how hard your dick just got."

I felt something else against my ass now. It was a little bigger but went in smoothly after all the preparation she did. After the widest part was inside, the rest got sucked in and was held in place by the round base. I couldn't help but groan at the new intrusion. "Get used to it, this plug isn't coming out for the rest of the night. Besides, the pink jewel suits you."

She pulled my pants back up and pushed on the plug before letting me stand upright. "This is your last chance to back out. After this point, if you give up I will tell Lily everything."

The plug didn't help to keep my resolve, but I wasn't gonna give up now. "No way, I have a date to get back to."