Chapter 12

I met Cindy and Madison in the entryway, before they could see anything else in the suite.

“Cindy, welcome. I’ll lead you in as soon as we’ve gone over some ground rules. Do you agree?”

Cindy looked both flustered and anxious, but she settled down and said, “I agree.”

“Tilly is here of her own free will, as are you. You are her friend and watching out for her, so I’m going to put you in a seat near the door. The other ladies and I have a special trusting relationship and I will have them tell you they are here because they want to be. I just met both you and Tilly, as you know. So, a few ground rules which I will record you saying. If everything goes well, we’ll delete it at the end together. I need you to acknowledge each point on camera.” I pulled out my camera to start recording.

“Cindy, are you here of your own free will to watch over your friend Tilly?”

“Yes.”

“Have you ever done anything like this before?”

“Yes.”

“You can stop everything by saying “Red Light”, but if you do, Tilly and you will need to leave immediately. Be careful using that phrase, because Tilly clearly wants to be here. If you’re concerned, you can say the word “Yellow Light”, which will cause me to take a quick break and see how everyone is doing. If you use that phrase too often, you both will have to leave.”

“I understand.”

“Say the phrases please.”

“Red Light stops everything immediately, Yellow Light causes you to take a break. If I use them too often, Tilly and I have to leave.”

“Red Light causes you to leave immediately, Yellow Light too often does as well.”

“I understand.”

“You will refer to me as Sir, if you need to address me. But I mostly want you to sit quietly and watch over your friend.”

“I understand.”

“Cindy, that’s not correct.”

“I understand, Sir.”

“Good. I’ll stop recording now. Follow me.”

I pointed at the chair I wanted her to sit in. As she sat down, her head was zipping around the room inspecting all the ladies, especially her friend Tilly.

“Cindy, one last thing,” I held up the video camera again, “please unbutton your blouse and remove your bra, I want a picture of you exposed with a smile as insurance until the end of this.”

She kept looking at Tilly completely naked and kneeling before finally unbuttoning her blouse and removing her bra. I took a few pictures and she dutifully smiled. I think she was a bit surprised when I told her to put everything back on. I explained, “In case you need to leave suddenly to get help, there’s nothing stopping you.” She looked thoughtful at that and nodded.

I put my hand on Ashley’s ass and said, “Please tell everyone why you are here and whether you want to be.”

“Sir, I was rude to Tilly today and you offered to let Tilly punish me if she liked. Yes, I want to be with you, wherever you go.”

I walked over to Jessica, “And you?”

“Sir, I’m here because you are here. I want to be here.”

I approached Madison, who had started to undress. “What about you? Do you know how Tilly feels?”

“Sir, I was just like Tilly a few weeks ago, wanting something I didn’t understand and being scared of that not knowing. I want to be here now with everything that I am. I hope Tilly can figure it out and join us.”

“We’ll see, I’m not sure we need anyone else joining us, but let’s see what fun we can have today.”

I turned to Tilly and Cindy. “These ladies and I have a very special and trusting relationship, far beyond anything you believe possible. I will not allow either of you to actually hurt them either physically or otherwise. You can leave at any time, but if you do, do your best to forget us and never talk about us with anyone. I would be most upset if I had to figure out how to deal with the consequences of trusting the two of you.”

“Ladies, am I speaking the truth as you know it?”

Ashley, Madison and Jessica all replied quickly and loudly. “Yes Sir!” Ashley added, “Don’t cross him.”

“Ok, so now, as the wronged party Tilly, what sort of punishment were you thinking of?” As I said this, I slipped the gag back into Ashley’s mouth. I pulled gently on her leash necklace, causing her restrained, yet limber body to go through such contortions to move further up the bed.

“Sir, you mentioned that I could have her lick me and that is exciting to think about. But I’d like to spank her once or twice before I lick her as she’s tied up. I haven’t been able to take my eyes off of her privates.”

“Privates? Is that the best you can do? If you want to play with it, you have to say the words that show you are serious.” I put my hand around the back of her head with my fingers lacing into her hair. “Come on, let’s get you into a better position.”

Tilly tried to stand up, but my hand kept her down. “No Tilly, stay on your knees.” As I said this, I started pulling her head towards where I wanted her and she quickly knee walked to follow my guidance.

“Yes Sir.”

“Good girl Tilly. Now, what do you call this?” My timing was perfect, I aimed her face right at Ashley’s pussy, but stopped her half an inch short. I’m sure it’s the only thing she could see as she gently tried to pull back. “Tilly? What do you call this?”

Tilly was making a noise, but it wasn’t really a word. I’m guessing this is the first time she’s been up close and personal with one. Ashley knew me perfectly, she started squeezing muscles and wriggling slightly, causing her pussy to flower open right in front of Tilly. She was rhythmically using her body to create a show for Tilly, and I loved it. I placed my hand back on Ashley’s ass and said “You’re doing great girl.” That got Ashley to start making some noises in her gag, but as usual, we couldn’t understand.

I leaned over and smacked Tilly’s ass lightly, but it caused her to jump, pushing her face right into Ashley’s pussy. Cindy leaned forward and looked like she as going to say something but when I looked at her, she settled back into the chair. In the meantime, Tilly had pulled her face out of Ashley’s groin and sat back in the kneeling position. I still had a grip on her head, but let her move as she liked.

“Tilly, I’m going to ask you again, what did you just push your face into?” Ashley was arching her back to show Tilly all different angles.

“Sir! My face was in her cunt!” Tilly was trembling after that confession.

“Good girl, let’s try putting your face back into her cunt.” With that, I pushed her face back into Ashley’s cunt. Not a word I use very often, but it seems it has special meaning for Tilly.

Tilly’s head was moving around, but I don’t think she actually knew what to do.

So I pulled her up to a standing position. “Since you’re not ready for that yet, let’s get the spanking out of the way. Is this a good position for you? Or do you want her over your lap?” I knew that offering choices when her head was overloading would get the right reaction out of her over time.

“Sir? I don’t understand.”

“Hmm, I guess you need to see for yourself before you can make that decision. I led her over to an armless chair I had positioned earlier and sat down. I pulled her over my lap with her ass sticking up. She was wriggling something fierce, but I had a firm grip. “I’ll demonstrate on you first this way and then the way she is now. That way you can decide for yourself. Ok?”

“Sir?”

“Count each stroke and thank me for it.”

“What?”

I smiled at Cindy who was staring at us with her mouth open. I smacked Tilly’s butt firmly, but not too hard. The cracking sound it made was probably more shocking than the actual stroke. Tilly grunted but didn’t make any other noise. I waited a few seconds before saying, “I guess that one doesn’t count. Also, you forgot to say Sir, so that’s two extra strokes. Let’s start over again.”

“Sir?”

I paused with my hand in the air. “Yes Tilly?”

“Sir, I’m sorry I messed that up, thank you for showing me how to do this.”

“My pleasure Tilly. So, after the stroke, count it out and say thank you.”

I smacked her harder this time on the same cheek. The sound was even louder and Tilly made a yipping noise rather than the grunt before.

“One Sir, and thank you.”

“Good girl Tilly. You’re doing fine.”

I continued for four more strokes. Tilly kept a clear voice for each stroke. I rested my hand on her blazing hot ass. I could smell how excited she was as well. In fact, I think I could feel her seeping through my pants.

“Very good Tilly, now lets demonstrate the position she’s in now. Then you can compare. Please get up next to her and grab your ankles. We could restrain you, but you’ve already done so well, I don’t think we need to. Do you agree?”

“Sir, I will hold my position without being restrained.” She crawled onto the bed next to Ashley and assumed the same position, just using her hands rather than the straps on Ashley.

“Good Girl, same rules as before, starting at one.”

CRACK

Tilly almost fell off the bed before pulling back and somewhat wincingly saying, “One Sir, and thank you.”

CRACK

Tilly was sobbing gently now, but she kept her voice clear, “Two Sir, thank you.”

This was the last stroke I planned for her, so I wanted to try something different. I grabbed one of the local glossy tourist magazines you find in higher end hotels and rolled it up. I looked at Cindy and she nodded at me.

“Tilly, this is going to feel different, please don’t make me do it twice.”

“Um, yes Sir?”

SMACK

Tilly yowled at this one, it went across both cheeks and left a wide white band that quickly filled in with red as the blood rushed back.

“Sssssiirr, threee and thank you.”

I could hear her pull herself together while she was trying to say that. I rested my hand on her ass and felt the heat coming off of her. It was time, so I slid my fingers down and found her cunt to be gushing with juice. My curled up fingers started to go right into her which caused her to groan loudly and push back onto my fingers. I cuffed her ass slightly and said “No, you’ll move when I tell you to.”

“Yes Sir, sorry Sir.”

I rubbed around her pussy lips causing a high pitched squeal to come out of her. I pulled back up to her hot ass cheek to deprive her of the pleasure she was clearly seeking.

“So Tilly, you said you wanted to spank her, but which way were you thinking? Was this your first time being spanked?”

Tilly collected her thoughts for a second. “Sir, My parents never spanked me, but when my Uncle and Aunt watched me as a kid, they would usually find a reason to do so. I just realized I never told my parents because I was so ashamed I had done something wrong. But looking back, I don’t think I actually did, it was just something they wanted to do to me. This is the first time I’ve been spanked as an adult and I had no idea I’d react that way to it.”

“So, what do you want to do to her now? You realize that these were very light strokes and although you might be sensitive sitting for an hour, there is no real damage.”

“Thank you Sir for explaining that. I don’t actually want to spank her now. I enjoyed what we did, Sir.”

“No, you need to see what it’s like on the other side, so stand up Tilly.”

Tilly complied and I showed a bit of weakness, I pulled her into my side and cuddled with her. She threw her arms around me and clung tightly. I was still fully clothed but she felt great under my arms. I pulled her around to be perpendicular to Ashley and said, “You should give her three strokes, just to see the other side. She’s gagged so she won’t be able to count out loud, but I promise, she’s counting on the inside. Isn’t that right?” I rubbed Ashley’s ass as I said that and she wriggled it as if she was nodding her head. She was really flexible.

“Go ahead Tilly.”

crack - Tilly swung and hit Ashley’s ass, but it didn’t make very much noise or even look like Ashley felt it.

“That’s pitiful Tilly, give it your all.”

“Sorry Sir, I’ll do better this time.”

Crack - Tilly wound up more and it made more noise, but I don’t think it was actually that much harder.