We’re back! I haven’t written in the last few weeks as baby Tiffany and I went on the most fabulous vacation ever. It far exceeded my expectations and I’m sure Tiffany would say the same. We went to the Caribbean for seven days and it was heaven. I really pushed the boundaries with Tiffany on this trip which allowed me to have the time of my life. Before we left Tiffany was being fussy and obstinate as she was not too happy that she was not allowed to pack her own bags. What two year old is? I finally gave in a little and allowed her to pick three of her favorite toys and I placed them in her bag. I forgot how difficult it can be to travel with a two year old but I must say it was worth every second. First I had to get Tiffany dressed for the ride to the airport and make sure we had everything we need for a four hour flight. Tiffany was not behaving at all and begging me to allow her to wear some gross outfit that no baby would ever be caught in. This upset me and I warned Tiffany the more she whined the more trouble she was making for herself. I finally had it with her and stopped doing everything to focus on adjusting her attitude. After thirty minutes of caning she became more agreeable to my rules and capitulated to my authority. I was so upset with her I placed a butt plug inside of her so she could think about her actions the entire trip. I took off her “travel safe” chastity device and placed her in a device with a metal lock. I reminded her to be ready when we go through security as everyone will figure out she is locked. This actually put me in a good mood as her pathetic little face had the look of fear on it like I haven’t seen before. I was actually going to dress Tiffany fairly conservative for the flight but her attitude changed my mind. She went from a cute t-shirt and a pair of baggy shorts, baby socks and ballet slippers to a pink onesie with unicorns, her baby bra, short shorts that didn’t hide her diaper, pink ankle socks with lace and pink sandals with bows and jingle bells. What a site! As she dressed I reminded her that one more whiny outburst would be dealt with in the most serious way possible. As tears ran down her face I felt like I had just hit a new high of my dominance. The best part was we were just getting started. The ride in the taxi to the airport was pretty quiet as Tiffany definitely got my message that I was at the end of my rope with her. When we got to the airport there were crowds of people everywhere. I could see some people looking at Tiffany and reminded her she better be on her best behavior and not to embarrass me in front of anyone. We were standing in-line to check our bags and I could see Tiffany shaking. I ignored her for the most part but after a while I decided to give her a treat. I opened her diaper bag and handed her a baba and her binky. To her credit she didn’t say or do anything that would have created a scene for her. We eventually checked our bags in and headed for the gates. As we walked towards the gates I told Tiffany to look ahead as we were almost at the security stations. I reminded her that she was about to be humiliated and she only had herself to thank. I was feeling so much power at this point I thought I was going to explode. I could feel Tiffany’s subspace energy and it turned me on beyond belief. I went through security first with no problem. As I turned around it was Tiffany’s turn. I could see her take a deep breath and walk through the security scanner and heard a sound that was music to my ears. The agent instructed Tiffany to stand on a rubber pad and proceeded to wave his wand around and of course another loud sound emitted from the hand held device. As I stood and watched Tiffany’s dilemma I felt a sense of pride that I had achieved total ownership over her. Tiffany was escorted to an area where there was more privacy. I followed them but they would not allow me to go in with her. After about five minutes Tiffany emerged with tears running down her face. As a good Mommy I sat her down and wiped away her tears and told her everything would be okay. I reminded her little girls face humiliating circumstances in their lives and this was part of being a girl. After a few minutes we walked to our gate and boarded without any drama. Tiffany knew people were looking at her but after what she had just went through I think it seemed like a relief that being looked at wasn’t as big of a deal anymore. This byproduct of her experience was another way to condition Tiffany to accept her life. Lesson learned for me as well. I’m all about conditioning so this was a pleasant surprise. When we arrived at our destination it was a very hectic experience. The airport wasn’t as nice as those in the US and the vibe could best be described as chaotic. We looked for the shuttle area to find our ride to the hotel but on our way we were accosted by several drivers offering to give us a ride to the hotel. We made our way to the shuttle area and the line was a mile long and we waited for about thirty minutes before we found out our hotel shuttle had broken down and would have to wait an unspecified amount of time. It was hot and humid so I grabbed Tiffany and headed back to the taxi area and eventually ended up taking one of those unlicensed taxis as the lines for the legitimate taxis were insane. This is a time when I wish I had a real man to take charge of a situation like that but as a Mom I had to take control. Tiffany is useless for anything like this. Once we got into the taxi the driver seemed pleasant and his English was very good. He seemed to have a sense of humor as he asked how old is your baby. Once he said that I felt safe and more relaxed. I told him my baby is a two year old girl and her name is Tiffany. He played along quite well and suggested that I purchase a pair of water wings if my baby was going to go to the pool. I could feel Tiffany tensing up and loved that she was feeling uncomfortable. I decided to have some fun and ask the driver if he could take us to a store so we could get Tiffany her water wings. He smiled and said no problem. Tiffany knew better than to say a word or look at me so she sat there waiting for us to arrive at the store. We came upon a store on a street that had shops as far as the eye can see. Our driver took us into a store that had swimming accessories and I purchased a cute pair of water wings with a matching swimming cap that actually fit Tiffany. My vacation was starting off perfectly! Oh, I should mention the water wings and cap were pink. Once at the hotel the checkin was fairly easy. When the driver brought our bags to us he said he hoped we enjoy our time and if I needed a babysitter for Tiffany he had someone that he could recommend. We exchanged contact information and went to our room. The room was quite nice with a beautiful ocean view. As I unpacked I told Tiffany to get ready for her bath. I knew it was time for a diaper change too and boy was I right. I placed Tiffany in the tub with her little ducky and proceeded to finish unpacking. As we were going to our room I noticed a bar area on the beach outside and all the people who were there having fun. Although it had been a long day my adrenaline was running and I was ready to hop into my new bikini and have a drink. Tiffany finished her bath and I put on her diaper and her baby bra and put her down for a nap. She feel asleep by the time I got out of the shower with her baba hanging out of her mouth. So cute. I snapped a photo for this memory. I was surprised she had not complained about her bottom hurting after the caning I had given her. I think Tiffany advanced that day and became a better baby. Enough about that as it was now my time to grab a drink and relax. I went to the bar and ordered me some foo foo house drink and sat around enjoying the ocean breeze. Of course I looked around to see if there was any eye candy but for the most part it was just couples enjoying themselves. As I finished my drink I was just getting ready to go back to the room and take a nap when I noticed one of the workers who had the body of an Adonis. He was as black as a man can be, lean, toned and probably 25 years old. Since I’m in my 50’s I thought he was a fantasy for me but I still could enjoy looking at him. As I walked away he came up to me and said he noticed me looking his way and was there anything he could do for me. I was floored! He was super polite and eventually introduced himself to me. His name was Pierre and he was 23 years old. He said he is a college student and works at the hotel part time to help support his schooling and family. My head was beating as I didn’t know what to say. He asked me if I was here alone and I blurted out I’m here with my baby. He asked me if my husband was here with me and I told him I am a single mom. He asked me how old my baby is and I told him two. He said he loves children and hopes to meet my baby soon. At this point I wasn’t sure what to do so I said I have to go check on my baby and left. He followed me to the elevator and I went back to my room. Tiffany was still asleep and my heart was beating so fast I couldn’t fall asleep if my life depended on it. I ordered room service and decided to not think about what I just said. Tiffany was well rested so I let her watch cartoons while I eventually fell asleep. The next morning I decided to further Tiffany’s punishment for her behavior the day before. I beat her ass, plugged her and placed mittens on her hands to insure she could not play with her toys the way she liked. My head was in another place as I wanted to go back to the bar and see if Pierre was there. Tiffany had crossed the line with me and I as determined make her pay while I played. By the time I got ready it was getting close to lunch time so I decided to order room service for Tiffany, feed her then go back to the bar for some adult interaction. Tiffany didn’t dare complain but did ask when she could go outside to the beach. I had no intention of taking her outside other than for a splash in the kiddy pool at some point but I just said when mommy’s ready she will take you out. It seemed like forever for the room service to come but eventually I heard a knock on the door and opened the door. Tiffany was on the floor playing with her doll and as I opened the door I hesitated thinking maybe I should have Tiffany hide until the server left but I was charged and decided to humiliate her by having to server see her. I thought this is just what mommy needs. I opened the door quickly and almost had a heart attack. Pierre was the server for Tiffany’s breakfast. He looked as stunned as i probably did. Tiffany was actually the coolest person in the room. Once I composed myself I looked at Pierre and he said you don’t have to explain. I muttered something but Pierre went about his business as if nothing had happened. He told me he was off in an hour and we should meet off the premises. He suggested a place and I arranged for a taxi to take me there. It was another resort a short time away. Once there I noticed Pierre sitting in a cabana by the pool. As I approached he smiled at me and said I look beautiful. We ordered some drinks and I began telling Pierre all about my life with Tiffany. Eventually he said I sounded apologetic for my lifestyle and in his opinion he admired my strength. He said he thinks it’s unusual for a woman to be so powerful but even powerful women need to take a break once in a while. Was he saying what I hope he was saying? I could feel myself getting wet and there was no way for me to contain my feelings. I leaned over and kissed Pierre as hard as I have ever kissed anyone. Pierre took me by the hand and walked me through the lobby to a room he had arranged for. Once inside I dropped to my knees and worshipped his huge manhood. Before I knew it Pierre was inside of me taking me like a bull takes it’s mate. I didn’t even have time to remove my bikini. He just tossed me on my back pulled my bikini bottom to the side and took me. I came several times like never before. After he lost his nut inside of me we laid there kissing all the while he stayed inside of me. I was in heaven! As we separated I could only think of how much I wanted to do this again. I wasn’t sure what Pierre thought but it seemed that his acquaintance with Tiffany had no bearing whatsoever. Then as I was ready to go into the bathroom to clean up Pierre said something that sent a chill up my spine. He said don’t clean up in the bathroom. That’s my gift for Tiffany. Let Tiffany clean you up and make sure you tell me all about it. I couldn’t believe my ears. I said ok I will do that. He said the proper reply is thank you for taking control and making me your bitch. I said yes and repeated what he instructed me to say. He said that’s yes sir! Do you understand? I understood and loved it. We took a taxi back to my hotel. Pierre disappeared and I went back to my room and gave Tiffany the treat of her life. I came like a volcano all the while telling Tiffany I was Pierre’s slut and I love it! Tiffany was compliant and would only say yes mommy. I told Tiffany she should be ashamed that mommy has no choice but to be a slut to other men because Tiffany is such a pathetic sissy. I could see Tiffany’s eyes welling up and to my surprise she said sorry mommy. I know I am not a man and probably never was. I will clean you everyday if that’s what you want. With those words I almost cried. I realized that very moment that not only do I own Tiffany I also have the freedom to use her anyway I see fit with zero remorse. It was so beautiful. As the days went by I was serving Pierre as his slut. I was instructed by Pierre to inform him about Tiffany’s response each and every time. I had mentioned to Pierre that before our vacation was over I wanted to take Tiffany to the kiddy pool as she was confined to the hotel room the entire trip. I’m sure Tiffany preferred to stay in the room to avoid the humiliation so that made me want to take her outside even more. Then one day Pierre shows up at the room and announces he’s arranged for a birthday party for Tiffany at the kiddy pool. Tiffany had a look or horror on her face and said but it’s not my birthday. Pierre said it is one and instructed me to get Tiffany ready for her birthday party. It’s a good thing I packed a frilly pink dress with all the accessories for our trip. It was my intention to only use it to humiliate Tiffany if she misbehaved. Tiffany was in shock as I dressed her and I was on cloud nine. The phone rang and it was Pierre and said everyone was waiting for the birthday girl. As we were riding the elevator down I told Tiffany she better not embarrass me. As the door opened I could see balloons, a sign and some birthday decorations. Tiffany looked so cute. She even had he water wings on which added to the excitement. There really wasn’t any real guest just a few hotel employees but we did give cake to anyone that came over to wish Tiffany a happy birthday. Pierre was the perfect gentleman and eventually took Tiffany’s hand and led her to the steps of the pool and as Tiffany stood on the steps Pierre went into the water and held out his arms and told Tiffany to swim to him. Tiffany looked around and said but I have my dress on. Pierre said it’s ok now swim to me. Tiffany obeyed in away that I have never seen before. She acted like a sweet little girl as Pierre played with her in the water. She was smitten with Pierre. It was really cute and warmed my heart. After a while it was time for Tiffany to go back to the room and get ready for her nap. She held Pierre’s hand all the way to the room. Pierre told her to be a good girl and listen to mommy and get ready for her nap. As I started to pick out something for Tiffany to wear for her nap Pierre came over to me and hugged me from behind. I could feel his manhood and tried to act like I didn’t notice. But one thing I forgot is that Pierre is in charge and he said hurry up and get Tiffany to sleep so we can do our thing. I put Tiffany in a diaper, bra and cute socks. She told Pierre thank you for a good day and thank you for all the presents he’s been giving mommy. He said they taste yummy. With that Pierre looked at me and said I think Tiffany needs a bigger present. I said what do you mean and he said what if Tiffany gets a deposit directly from the source. OMG ! I couldn’t resist so I said whatever makes you happy. With that he proceeded to instruct Tiffany on what he liked. Tiffany was eager, willing and hungry. It was a sight to see. When he was ready he held the back of Tiffany’s head and exploded. Tiffany did her best to keep up but couldn’t. At that point Pierre instructed me to clean up what Tiffany could couldn’t. Needless to say this became a daily routine until we returned home. Our trip home was one of peace. Both Tiffany and myself were in a place we had not shared before. Once home I noticed Tiffany’s attitude had shifted. It seems she had finally found peace in being baby Tiffany. She is much more girly, more confident and more submissive than ever. As for me I feel a sense of peace also. I now feel like I have the best baby ever. I’m not sure what I will do next as I was thinking of maybe finding a steady boyfriend so Tiffany can clean me more often. I feel like a new mommy and am now looking forward to exposing baby Tiffany more and soak in the pleasure of owning a pathetic, degraded sissy baby.
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