It all started in Miami the night before I was to meet up with Goddess Jessica. Throughout the night I was not able to sleep because of the excitement of serving Goddess Jessica on vacation. The following morning I got in the car and went to the W Hotel in South Beach. Upon entering the lobby my heart skipped a beat as Goddess Jessica was sitting there looking irresistible in her romper and gorgeous black wedges. Once we both got into the car she looked over to me and asked “You have your cage right?” Nervously I instantly answered “Yes Goddess.” Trying to be as quiet as possible so that the driver did not hear me. It was followed by a “GOOD BOY.” Words that we all crave to receive from Goddess Jessica. (FYI an in person “Good Boy” is a euphoric feeling like no other.)
Upon Arriving at the Airport I immediately took the our luggage’s and carry-on’s scurrying like a little puppy behind its owner. Using her innocent smile that makes everyone weak and easy to manipulate Goddess Jessica got out of any issues with her overweight luggage.
Goddess Jessica and I arrived at the resort early and the rooms were not ready so Goddess went to get changed into a beautiful golden bikini. Seeing Goddess Jessica with her perfect tan and the bikini was jaw dropping. People left and right were staring at her and then gave me a puzzled glance. I am sure some thought that I was but her slave here only to make sure Goddess Jessica’s vacation is as enjoyable as possible. Of course that includes paying for everything Goddess wishes. After a few drinks Goddess Jessica tells me she wants to go to see the other side of the Island since it is still to early to check in. On that beach everyone instantly noticed and commented how good she looked (some even went on to make comments about her guns). Once we got into the rooms she ordered me to put my cage on and report back to her room. Hurrying as to not upset Goddess Jessica I went back to my room and put on my chastity cage and went over to hand Goddess Jessica the keys to my dick. She told me “MY KEY! MY DICK!” Those words were enough to give me a partial erection that was quickly restricted by the metal bars of my jail bird chastity cage. Goddess Jessica wanted to eat conch so we got into a taxi and headed out into town for some right away. On our way back Goddess Jessica was getting thirsty and told me to get her a drink at a beach side shack while she walked to the water and sat down on the pier. Back in our room I was blessed with the nightly task of rubbing lotion all over her toned smooth as silk legs. I’ve never felt something so glorious it was as if I died and went to heaven. Dangling the key from her golden necklace we went down to the sea side grill to eat supper. I felt privileged to sit next to her at the table. All I was thinking about was Goddess Jessica in the dress she was wearing and her heels. Goddess Jessica was dangling my key that hung between her perfect chest. She decided what we were having, it was fantastic she is a culinary genius. When we got back to her room Goddess Jessica took out a vial of poppers and ordered me to inhale. Not knowing what was going on (as poppers are illegal in my country) and the fact that I can not nor do I dare to disobey my Goddess Jessica, I obliged and took a big whiff. The rush of pure pleasure and lust that I felt was only matched by Goddess Jessica mentally ruining me as she teased and gave me the biggest blue balls of my life. My dick was trying desperately to explode from its cage but it was firmly locked in place with no chance to grow an inch. As she sat on my chest and game me another 2 hits from the poppers she had me totally powerless to resist and had me repeatedly say that my dick belongs will always belong to Goddess Jessica and that she owns me. Before I knew it I was alone in my bed lying there in agony thinking about what just happened.
The next day was the day that I paid for Goddess Jessica to swim with the dolphins. It was not the regular swim but she wanted the royal swim so the royal swim is what Goddess got. Before we left to catch the boat at the nearby marina we went and got breakfast and a few drinks for Goddess Jessica. Once we arrived to the island we went to the island bar and ordered a drink for Goddess and I was permitted to order one for myself for being Goddess’ good little bitch boy. When it came time to swim with the dolphins I watched from the dock as Goddess Jessica got into the water to start her slave paid swimming experience with the dolphins. Watching from the ledge I was able to see how much fun Goddess was having in the water. Goddess’ swim was a lot longer than I thought but I was having so much fun watching the joy in her beautiful face and fantasizing that I was one of those dolphins. After Goddess Jessica finished her swim she wanted to get another drink before boarding the last boat off the island again I was allowed to have another drink with Goddess Jessica’s permission. When we arrived back to the resort Goddess and I were sitting by the bar and 2 local cops that were on vacation started talking to us. Goddess Jessica and I were invited out for a party that they were going to and Goddess said we would love to go (I go where Goddess leads me.) Goddess had a blast and I was given the liberty to drink a little as to not raise suspicion of being her slave (Not that Goddess would mind. Goddess Jessica was doing another kind act not to publicly embarrass her slave) Later that night when we got back to the resort Goddess Jessica told me to come to her room. I was incredibly worried about being blue balled again. Last nights experience was not at all horrible actually it was quite the opposite the agony and suffering that Goddess Jessica caused me is and always will be embedded into my memory. When I entered the room Goddess was holding up the poppers again and with a sadistic grin ordered me to take off my pants and kneel down in front of her. Instantly after the first inhale my mind melted and Goddess Jessica started teasing my just like last night. This I was to get on the bed and as Goddess sat on my chest I was to take another 2 deep breaths and hold em in. At this point there was nothing to do but let Goddess Jessica’s voice totally take over and control my every movement and desire. After a few solid minutes of agony as Goddess teasing my caged dick she told me to get off the bed while she dangled the key to my manhood in front of my eyes. Like a trained dog I was made to beg for my key on the floor while she laughed at me from the bed. It was my only chance to have any form of release. Eventually Goddess tossed me my key and then ordered me to unlock myself. I did. She told me to hold out my hand and she spit into it. I thought she was going to let me relieve my swollen balls, it’s been almost a year since I last came. She gleefully told me to put her cock back in my cage! I couldn’t believe how cruel she could be! The next thing I knew was being kicked out back to my room until summoned in the morning. Goddess Jessica told me that I better be back in my cage when I get her morning cappuccino. This was my first daily task. I would wait in my room patiently until Goddess would send me the morning “Get me a cappuccino slavie” message
The next morning was a little different. Goddess Jessica wanted to go snorkeling. I woke up extremely early making sure to get ready to serve Goddess today and before presenting her with my key, proof of chastity and her morning cappuccino I was tasked with inquiring about going snorkeling. Again Goddess wants Goddess gets. We booked the snorkeling excursion that afternoon. ( Goddess Jessica was thinking that the following day would have been better but against her instincts we booked today). We arrived at the marina early so Goddess Jessica and I went for a bite to eat. Goddess Jessica choose our light lunch and it was terrific and healthy. It started raining on our ride and it was freezing cold. Goddess Jessica wanted something to warm her up so I ran to the bar on board the ship and got whatever she desired. When we arrived back at the resort we each got our separate rooms and later went to explore the hotel. Goddess was all dolled up with her hair in pigtails. Goddess Jessica ate Indian food and it was great. After supper it was time for drinks. This time I was allowed to drink with Goddess. At the bar Goddess Jessica leaned in and started mentally preparing me for receiving Goddess’ 12 inch strap-on. I was terrified and yet game to fully submit myself and my anal virginity to Goddess Jessica. What greater way to demonstrate dominance over a man than pounding him mercilessly. Throughout the evening Goddess Jessica kept tormenting my mind and planting the seed that will blossom into happening some day soon. Goddess Jessica was feasting on my fear and panic. I typically remove my glasses and rub my eyes when nervous or uncomfortable. Let’s say I was constantly rubbing them. I was getting mentally prepared for what was going to happen later tonight. Goddess Jessica suggested that I relax and stop drinking so I don’t tense up because that is when it hurts. I was in full panic mode after that. Worried shitless we left the bar. Goddess had a huge grin knowing what would come of me and I was white as a ghost for the same reason. Goddess Jessica followed me into my room and told me to kneel down. She went next door to her room to get ready and came in trough the connecting door. My heart was going crazy. I did not know what I was feeling. Was it fear or did I actually want this to happen. Maybe it was just Goddess’ smooth, calm, nice yet dominant voice penetrating and making me want to experience receiving Goddess Jessica’s giant cock. Goddess ordered me to take more poppers and then it became clear. I wanted to receive Goddess. She threw me over the bed, opened my legs and started running her hand up my thigh and whispered in my ear " just kidding I don’t have my strap-on with me.". I just collapsed and she laughed walking back to her room and said as she closed the door " goodnight my little anal slut.". There was no sleeping after that.
The following morning was a “regular” tanning day. Getting Goddess her morning cappuccino, all her drinks, and spraying Goddess with sunscreen with the fear of missing a spot and burning her body. The idea imbedded from last night never went away and I even told Goddess Jessica that I think I would really enjoy it. Goddess then said that if I was serious to look up a sex shop nearby. And I did just that. We got into a taxi and asked him to take us to the address. When we got there we found out that it has gone out of business… But we tried another and same outcome. “I guess it will have to wait until New York then” Goddess said. Upon arrival to the hotel Goddess Jessica went back to the beach with her hot black bikini and I was in awe to be able to see Goddess Jessica’s prefect tan body in the sun tanning as every single man that walked by had to slow down and take a mental picture of it. It was hard to remain focused but my cage solved that issue every time. Goddess Jessica would chuckle every time I put my hands down my pants to adjust it because she knew that I was trying to get hard and suffering greatly for it. There was a giant thunderstorm that night.
The following day was our last day on our adventure of agonizing torment and pleasure. It was the warmest day of the vacation and Goddess Jessica wanted to take advantage and tan one final time in the blazing sun. Keeping Goddess Jessica’s body from burning was especially important today since it was hot. When it was time to check out we made our way to the airport and flew back to Miami where Goddess Jessica boarded her flight to Denver and that was the end of the happiest 5 days of my life. Having the privilege and being able to serve a Goddess such as Goddess Jessica is the highest feeling of ecstasy a slave can achieve. I look forward to being Goddess Jessica’s vacation slave again.