Chapter 16

“You said that Dawn told you about her first time, why are you shocked?”

“I guess I didn’t really think about it, Master. I never even thought of my ass as an erogenous zone until you started playing with it,” Faith said. Hope added, “How would it even fit, we’re so small. I’m not even sure why you would want to. We don’t have sexy asses like Dawn or the other pets, ours are just flat.”

“First, Dawn thought it wouldn’t fit, or that it would be painful and she would hate it. Ask her how she felt after,” I told them. “Second, you both do have sexy little asses. If you want to have more of a bubble butt like Dawn has, you can talk to your trainer. He’ll set up your exercise regimen to include exercises to build up your asses, but your boots will help with that as well. The heels will help tone up your ass and legs.”

“As a final point, think about how much you enjoyed having your asses played with. If you don’t enjoy it you’ll never have to do it again, but I can almost guarantee you will both love anal sex. Try to incorporate some anal play when you’re having fun with each other, or ask any of the other pets when you are playing with them. I think you’ll open up to the idea fairly quickly.” I told them as I got them both into the cart.

“Faith, as for what I told you we would discuss later. I’ve noticed you tend to be more dominant with other females. I have no problems with you being the more dominant partner with the other pets. Most of them will be happy to let you dominate them. However, don’t try that with anyone other than the pets during sex games. I haven’t seen you do anything to worry about, but keep it in mind.”

We pulled in to the pens entrance and I kissed them both as I helped them out of the cart. “The rest of the pets are probably in the exercise yard or just finishing their lunches. You have your exercise session with the trainers, and then you can have some fun with the other pets for the rest of the afternoon. I will see you tomorrow as I’m not going to be back for dinner.”

They both kissed me and headed off to the exercise yard. I got back in my cart and headed off to the other end of the island. I stopped at the ski shack and checked the maintenance sheets to make sure the watercraft were checked yesterday. The maintenance crew was supposed to clean them and check for damage when they came to refill the tanks. The two hundred gallon tank here was good for keeping the skis topped off between casual rides, but I knew my pets. I’d be surprised if any of the skis had more than a quarter tank by the time they finished yesterday, so they would have needed the truck. After verifying that everything was taken care of, I headed over to the docks.

There was one maintenance task I did myself every week. I walked out to my boathouse and opened the outside door. After checking the gas and oil levels, I fired up the World Cat 320 and backed it out. This was my personal use boat and I preferred to do the maintenance checks on it myself, mostly so I could take it out for a couple hours of quiet time on Saturday afternoons. After I got back, I ran through my engine checks and fired up the electronics to make sure they were in working order and picking up. All eleven pings were active, just as expected, so I shut it down and locked up the boathouse.

Antonio told me I was being over cautious with the extra security and the electronics setup on the boat, but I prefered to keep all my bases covered. This and the fishing boats were the only ones capable of running over 400 miles without refueling. They were the only way a new acquisition could reasonably attempt an escape with any chance of success. Each boat’s keys were kept secure in their own safe at the dock master’s shack and only ones who knew the combinations were me, Antonio’s family, and the boat’s captain.

I finished my checks close to sundown, so I put the keys up and headed back to my cabin. I knew Kayla will be arriving soon and I had special plans for tonight. Kayla had come to us thirteen years ago after finishing her accounting degree at Berkeley. Father was looking for a CPA and she had almost two hundred thousand in student loans to pay off. The offer of a job managing our family fortune for fifty thousand a year, with the signing bonus of paying off her loans for a five-year contract was double what she could have expected anywhere else. Even the possible ethical concerns of our family business weren’t an issue for her. We found out this was because she had a submissive nature a couple months later, when she signed a contract with father to become his pet.

She still managed our accounts and drew her yearly salary, but her only expenditures were expensive gifts for the other pets at Christmas time. She still insisted that we not tell them where the gifts were coming from as most of them couldn’t afford to buy gifts for each other. We marked them as gifts from Santa for her every year because she didn’t want the others to feel bad they couldn’t get her something in return.

Kayla arrived around 6:30 to find a romantic candle lit dinner for two awaiting her. I had prepared fresh grilled marlin with grilled potatoes and vegetables for dinner and had a bottle of wine chilling in an ice bucket. I knew the romantic scene wasn’t necessary, but I enjoyed the way my pet’s eyes lit up when I did something special for them. She knew that she was joining me for dinner, but this was far beyond her expectations.

Her smile lit up the room as I led her inside and to her chair. Kayla was fully dressed up for our evening together and looked like a pale African goddess. At 5’11’’ bare-footed the three inch heels on her thigh high giraffe skin boots brought her up to my height. The shoulder length giraffe skin gloves, and giraffe skin corset that pushed her delectable f-cup breasts up while leaving them completely exposed completed the ensemble. Her long brown hair flowed in waves down her back, perfectly matching the darker spots on her corset.

I cupped her perfect ass as I pulled her chair out for her to sit, then poured us each a glass of wine. I walked over and turned on a CD of light classical music before sitting down to eat. We had a quiet meal, enjoying the music and each other’s company. After we finished eating, I topped off our wine glasses and led her over to the wing back chairs so we could relax and enjoy the music for a while longer.

She demurred taking her own chair, instead sitting down in my lap and snuggling close to me. We sat for a while, sipping our wine and listening to the music, before she sat back and looked into my eyes. She set her wine glass on the table and said, “Master, I want to thank you for tonight. This was so much more than what I expected when you told me it would just be us tonight. The fact you would do this for me just shows why I love you so much. I would like to try something tonight and I have a confession to make. I know you have files for all of your pets to track their likes and dislikes, and mine are not completely accurate.”

I raised my eyebrow in confusion as she looked down at her lap and continued. “When I asked to become your father’s pet thirteen years ago I asked him for one concession in my contract that was never written down. I was horribly afraid to try anal sex, and he promised me that he would never take me that way unless I asked him to try. He even put it in my files that I had tried it and did not like it out of respect for my wishes. The fear faded over the years but I wasn’t interested in trying it until Samantha joined us.” I nodded in understanding. Samantha was my most anally minded pet, to the point she preferred having anal sex over vaginal. She was just wired so she received far more pleasure that way.

“Hearing her rave about how good it was for her started to get me curious. I was afraid to ask you to try, because I didn’t want to disappoint you if I ended up not liking it after all. About six months ago, I just had to try something, so I asked Katherine for a favor. She is so gentle and understanding that I thought she would be the best person to try exploring anal play with, and she wouldn’t be upset if I didn’t want to continue. We usually get together every couple of weeks anyway, so she started slowly introducing me to anal play. After a couple session of her just using her fingers on the outside, I asked if we could go further next time. Our next few sessions she used her tongue and started probing inside. I loved it and on our fourth session of that, I finally asked her to finger my ass. I have been trying to work up the courage to take the next step, and when I heard we would be alone tonight I knew it was my chance.”

She looked back up into my eyes and asked, “Master, will you please take my anal virginity tonight? I know it will be painful at first, but if my reaction the Katherine’s fingers are any indication then I will love it. I’m just sorry I waited so long, especially after what you did for me tonight. I feel like I have been holding out on you,” she said as she buried her face in my shoulder and started crying.

I set my wine glass on the table and wrapped my arms around her. “Shh my pet, I’m not upset with you. I have known about your deal with father since I started running the Menagerie. I won’t say I haven’t lusted after your perfect ass on more than one occasion, but I’ve always respected your wishes. I would be delighted to take your anal virginity of you feel you’re ready.”

She pulled back to look at me again, “You knew? You have known all this time, and you never tried to pressure me. You insisted on taking your other pets that way, but you never mentioned it to me, why?”

I smiled as I rubbed her back and replied. “You’re not like my other pets love. You asked my father for that restriction and we respected it. With the rest of our new pets, it’s part of the training process that helps them accept their new lives. You knew what you were getting into when you asked my father to make you one of his pets, so it was a different situation. I already told you I would be delighted to be your first time. If you enjoy it we can fix your files and do it again in the future, if not, at least you’ll be sure.”

“Thank you for being so understanding, Master, but I’m sure you will be changing my files tomorrow. Katherine has been sending me into orbit when she plays with my ass, so I know I’ll love it. I’m mostly upset with myself for waiting this long because I was afraid of the pain,” she told me with tears still sliding down her cheeks.

I reached up and gently wiped away her tears. “I know you don’t like pain. It will hurt at the beginning, but I’ll be as gentle as I can. We have all night though, and as much as I’m looking forward to finally having your perfect ass, I want us to relax and finish our wine first. I enjoy holding my stacked giraffe in my arms.”

She smiled and snuggled back into me as we both reached for our wine glasses. “One more thing, if I do end up changing your chart, I expect you to visit Katherine first thing Monday morning. If your anal ban is over, I expect you to have a proper tail as soon as possible.”

She giggled as she squeezed closer to me. “I have one more little secret Master. I’ll start wearing my tail tomorrow either way. Katherine made it for me a couple weeks ago, and I was holding off wearing it until I was brave enough to ask you to take me. I have been wearing a beginner plug at night when Scarlett and I were alone in our cabin. She has been keeping my secret for weeks while I worked up the courage to do this.”