Mistress's Vacation Ch. 01

For over the past two years I have been in contact with Mistress R. I have been one on her most ardent followers to the point of speaking with her weekly if not daily. Mistress and I have come to an understanding and we both feel quite strongly about each other. Or more realistically, I worship her and crave her domination and voice, she in turn like to twist me into circles and make me do the most deviant acts for her pleasure.

After a five-year run of owning and slowly building my own business I sold it to a corporation. Getting my financial business in order, I made an invitation to Mistress for a vacation. I would pay for her travel and stay in the Caribbean with me for a week. Our main purpose would me for me to serve and service her in any way she sees fit. I set it up for a month later so that she could schedule time off and attend to her family needs. I am not certain she has a family, but I anticipated that she would need the time to plan and schedule the time away from her home. She was delighted to have a vacation and mentioned that I might regret my invitation. I could hear her immediately planning, and scheming to get the upper hand. She made a list of things that she felt I should do and would send them via email for me to complete.

The first thing on her list was to mail her all of my bathing suits. I am in my mid thirties and am in good shape. I run five miles every other day, and work out at the gym on the off days. I wear what I am comfortable in and always try and look my best. I have always though that women like a sharp dressed man. So I purchased three running shorts/bathing suits that I felt I would wear. I mailed them to her and she responded that I am not allowed to cum for the next three weeks, without her permission. She knows that I love to jerk off to her pictures and dirty panties.

The second thing on her list was to purchase a strap on dildo system and dildo that I might like. Her express instructions were to increase the size of my ass each and every day with various size butt plugs and vibrating toys so that I would not have any pain and could service her to my full potential. It seemed that she likes humiliating me, but secretly I loved it as well. I was not allowed to jerk off any time I wanted over the three remaining weeks, and had to alert her and gain her permission to cum.

After receiving another package from Mistress filled with her used panties and pantyhose that were all dirty, I was ordered to sleep with them each and every remaining night to fill my senses with her scent. I was to only wear her panties under my jeans and if possible purchase a cock collar and lead so that she might utilize it on our trip.

About two week from our departure date I became worried that I might not get thru customs with all of the sex toys I was bringing in, so I put together a package of goodies and mailed them down in advance of our arrival. Dildos, rope, thongs, her gift of two new strap on harnesses, and numerous butt plugs and gags. I also included three dildoes for her with different lubes I thought she might use. I mailed the riding crop that I know she loves and a huge selection of bathroom soaps and toiletries from one of those bath and body places at the mall. It came in a really feminine basket with bows and loufas and scented oils.

I felt truly ready and with two weeks remaining I mailed that package out. I felt prepared. I also called ahead and confirmed that the lingerie store I had seen on previous trips would be open. I had met and talked with the storeowner on previous trips and she was always open and helpful with me. She confirmed that she would be open and I booked a reservation for an afternoon that she would close her store and only open for Mistress and I. This way Mistress would gain all of the attention I wanted to adorn her with, and I would get the bill for all of her under things.

One week before our vacation Mistress emailed me a list of rules and regulations for the trip.

1.I am her slave to use and abuse. Her fuck toy to play with and her boy toy to show off and tease in any manner she sees fit. I am her ass slut to fuck and all of my holes are to be open to her cock.

2.My cock was to be clean-shaven every day.

3.Her pussy was to be licked and trimmed to perfection every morning.

4.I was responsible to make sure she did not get sunburned and be sure to have ample supply of sun tan lotion when every she was in the sun

5.She would dictate what I do and do not wear every day.

6.We would eat out every night at a nice restaurant.

7.My ass was to be cleaned and lubed every morning and kept full with a butt plug of her choosing.

8.I was responsible for cleaning all of her negligee and lingerie with her direct supervision.

9.I was to wear her collar that she would present to me on the day of our arrival. If I could not tolerate any of her rules and wanted to end the vacation and just go to dinner with her every night all I had to do was remove my collar and I would not be her slave.

10.Enjoy myself and let her enjoy herself. If either one needs a time out from the other, then the words Snow Showers were to be utilized and we each would have a six hour window of time to spent time away from each other.

I thought that these rules were great, they established some rules and opened the idea that this was more than just some guy taking some woman on a free trip and screwing around. I was to be Mistresses slave for the week and we were going to use that time to play and see how compatible we were.

Over the three weeks in preparation I had utilized three different butt plugs and felt more comfortable with my ass being cleaned and lubricated every morning. I made sure that all of my bags were packed and took some money out from the bank in cash. Credit cards are nice, but cash is king, better to be prepared and have opportunities in life, than to be restricted with credit cards.

The departure day had come and I was excited to be leaving. Early to the airport and a quick flight down placed me in front of Mistress in under three hours. We hugged and kissed at the airport and loaded our bags for the taxi ride to the apartment. I was very excited, as was she. I think we were both hot and tired from our flights, yet excited to be together. After the stop for the key to the apartment and carrying all of her bags to the third floor apartment, the manager gave us the grand tour. He was available 24/7 at a push of the button. We were the only renters and could feel free roam about without concerns of prying eyes. He left and drove off. As Mistress checked and locked the door, she ordered me to my knees... Strip slut and be quick about it... I removed my clothes in record time and kneeled at her feet. Lets go out to the deck she ordered. As I crawled I couldn't help but notice that Mistress had a pedicure and seemed to be dancing as if she had to go to the bathroom. Once on the veranda, she asked if I was ready to be her slave for the week. I replied yes and she drew me close and said good eat me and drink my juices. I proceeded to remove her wet and sticky panties and place my mouth over her pussy as she let go with an urgent stream of urine. Drink it all slut... I gulped and guzzled all of her urine as she placed a silver neck choker on my neck. Very nice slut now Present yourself to me and let me inspect my property. As I kneeled and felt her healing touch, I was asked to show my ass and start unpacking her bags, she wanted to shower and get into her swimsuit. As I placed all of her bags on the bed and began unpacking I noticed Mistress had over nine swimsuits and all of her dirty laundry. I was in heaven, I continued to unpack her heels and flip flops, her sheer bodice wraps, and her bras and two corsets. She also had a number of dildos and whips that she had packed as well.

I grabbed all of the toys and placed then on the counter in front of the mirror in the main bedroom. I organized all the butt plugs and dildos to the right and open my package that I mailed earlier. I took all of her dirty laundry and placed it in a bag near the bed, and placed her gifts on the bed and resumed my position on the floor outside of the door. Slut are you on your knees.... Yes Mistress I replied, good then crawl in here and watch me shower. You may stroke my cock but you are not allowed to cum. do you understand Slut? Yes Mistress I whispered. I watched as mistress washed her hair and lovingly played with her nipples and breasts, as I continued to stroke my cock and jerk off. Do you like my nipples slut? Yes mistress you are beautiful Mistress. As I watched Mistress continue to wash I was playing with her cock and bouncing with my butt plug. Mistress laughed and said Slut – is that butt plug not enough for you? Go and get the red silicone dildo and place it in your ass, and make sure my cock stays hard. As I was crawling back into the bathroom mistress was drying off and proceeded to sit at the mirror and comb her hair. Give the Dildo to me Slut.... Mistress proceeded to place it at her pussy and fuck herself with it a few time and gave it back. Lick it clean slut- Know my taste then remove your butt plug and place the dildo in your ass. As I was sitting on the red dildo mistress grabbed my hair and pulled me to her pussy. Okay slut, lick me to orgasm and I want to see your hands playing with my cock. Mistress proceeded to comb her hair and grab her victorias secret swimsuit and place the top on her lovely breasts. Keep licking slut... I want to cummm. That's right nibble on my clit and lick my lips. Mistress leaned back and grabbed my head to press to her pussy and clit as she orgasmed over my face. That was quite nice slut. Lets see what you have completed with the unpacking – place that butt plug back in your ass and I will see you on the veranda.

As Mistress placed her thong on and slipped her platform heel on for her walk to the veranda, she grabbed the leach and collar for her cock. Okay slut, bring the tanning lotion and prepare me to go outside as I strap this on to your cock. I opened the tanning lotion and proceeded to cover mistress from head to toe with number 30 tanning lotion. I had mistress remove her bathing suit and spend a little too much time on her breasts and pussy. Mistress also spanked me for playing with her ass for too long. I was punished for that with mistress sitting on my face with her ass right on my nose as she strapped her leaches and collar on her cock. There that is much better slut. We spent the rest of the afternoon in the sun placing suntan lotion on Mistress and her tugging at my cock leach. Our conversations touched on her quest for the right slave, and her frustrations with her phone domination service that was doing exceptionally well. She was still seeking more and felt unfulfilled from the phone domination. People calling and getting their ten minutes of phone sex, then hanging up on her and leaving her horny and cranky. We spoke of her plans for the week and how she was looking forward to fucking me and playing with me in public. I mentioned the appointment with the lingerie store and how I had the afternoon booked for her to pick out different outfits. Mistress asked if I had found her dirty underwear. I replied yes and she said that I would wear her dirty underwear every day and that she would pick out what she felt looked most humiliating on me for the day. My butt plug would stay in otherwise. I watched her go and grab my swimsuits that I had mailed to her over a month ago. She explained that she had removed all the liners in the swimsuits and wanted me to wear these swimsuits when we were in public with her dirty panties. She liked the idea that anyone might see her property as a cock and balls with a nice ass in a thong and the outline of her panties thru a wet bathing suit. She proceeded to explain that this evening, as we are at dinner I would be submissive to her and that I would be fucked later in the evening. So in preparation for that I would have the remote control butt plug in my ass that might or might not be vibrating at her whim.

As she released my cock from the leash after I had followed her into the shower, she explained that we would be dining early and off to bed early as we were both tired and to be prepared for a long day tomorrow. I licked her pussy and ass as she showered and tried to tongue fuck her ass as she moaned and pinched her nipples to a nice wet orgasm. I followed up with drying her off and she said shower slut and be sure to clean you ass. I will be watching. I showered and washed my hair is record time, My enema and rinse was clean and my ass was prepared my her with a nice dose of lube to make sure everything was nice and wet for her vibrating cock. We both dressed in Caribbean attire. Mistress in a flowing sundress of pink flowers and black bra that was noticeable from close up. Modest heels and an ankle bracelet. The remote control for the butt plug was placed in her purse. I was in her black dirty thongs that I kissed before placing on my body.

Reservations for dinner were made weeks in advance and we were seated at one of the more secluded tables with a very attractive waitress. Mistress complimented her on her heels and skirt. As they made small talk I felt my butt plug vibrate and my cock beginning to get hard. I was jumping around the table and trying to act nonchalant about it, and the waitress mentioned – Are you okay? Ohhh don't mind him – it's the vibrating butt plug in his little butt. The waitress smiled knowingly, I am going to enjoy waiting on your table this evening! Mistress asked if she had shocked her, and the waitress said, no – there are just so many vanilla folks here on the island that I don't get to play much. HHmmm murmured Mistress. We are here for a week and will be on the beach all week. Find us and perhaps you will find yourself in a similar position. The waitress leaned forward and whispered – I might like that.... Mistress. Does he lick good pussy? May my tongue turn black for saying so in front of him, but he is exceptional! Said Mistress. Let me get your food and leave you folks to it, I will see you on Tuesday, my day off.

Dinner was progressing fantastic, and I felt my red humiliated cheeks returning to normal after our brief dialogue with the waitress. Mistress proceeded to drop her fork and asked me to get it for her. And while I was on my knees to give her her appetizer. I quickly moved under the table and made sure that the tablecloth was pulled down in front so that no one could see me. I licked Mistresses toes and proceeded up her leg to her pussy. I could smell her sex, all moist and wet. Her panties were silky wet and just glistening with juice. I moved them over and started licking her juices up as I felt my butt plug vibrating on the highest setting. I heard Mistress laugh as I hit my head on the table and felt her grab my hair and pull my hair and face back to her hot nest of juice. Heels on the floor were heard clicking, as the waitress returned, Is everything all right? Asked the waitress, I heard a loud thump then what sounded like you laughing. Ohh everything is fine and getting better and better dear. Could I sit with you while your man is in the bathroom? Please help your self. As she is sitting in to sit down, and he is not at the bathroom dear. He is eating my pussy as an appetizer, and he is my Slut for the week. Mistress later told me that she blushed and smiled knowingly. I hope he is quick about it as your food will be ready in a few minutes. Mistress pulled on my hair once again, and said did you hear that Slut – keep licking me. The waitress had one hand under the table and was pinching my ass and I think she could feel the vibrating plug in my ass running on high. I was licking and nibbling on Mistress clit as she said excuse me one moment – she relaxed into a deep moan and slowly said "Lick me clean Slut" I licked and tongued Mistress's pussy of all her juices and even got a quick flick of my tongue in on her ass which she immediately chirped to. Get up Slut. I slowly came from under the table and move to sit between Mistress and the waitress. I hope you enjoyed your appetizer Slut. Yes Mistress I murmured. I readied my napkin to wipe my face off and mistress grabbed my hand and said Dear – could you help him clean up. The waitress blushed a very deep red and said I would love to. As she leaned over to kiss me and lick up my Mistresses juices I felt her hand on my cock slowly outlining my cock in my thong panties that were Mistresses. Very nice Dear – Make sure you are available Tuesday. We are on the south end of the beach near the red hut. The waitress nodded and said delicious – I know the spot.

As she got up she thanked Mistress for the opportunity to play with us and said that she would be looking forward to cleaning Mistress up again on a more personal level. Mistress smiled and nodded and said I look forward to it – perhaps I will even let you fuck my Slut. Bring some ice with you and make sure your pussy is clean-shaven and wearing a thong. Mistress smiled at the waitress and she replied – As you wish Mistress, and disappeared to get our dinners. I do believe that I will enjoy this vacation immensely Slut. As will you. Thank you for coming Mistress – no pun intended as we laughed and clinked glassed of water. The meal was fantastic as we spoke of current events and the newest fashions that Mistress might see at the store tomorrow. We finished out meal and as the Waitress returned to give us the dessert menu, Mistress shook here head, no thank you dear, just the check, We will be having dessert later.

After I had paid the check and escorted Mistress to the door, she asked if I gave the waitress a tip. I nodded and responded a very good tip Mistress with our phone number. Good she will be fun and it will be interesting to watch you get sandwiched by two strapons later in the week. I started to feel my cock twinge in response to her as my ass started vibrating again. Ohhh you are evil Mistress and I am so glad you accompanied me on this trip. Lets get you back to the room Slut, I want to see you naked. We walked back to the car hand in hand as my ass was vibrating and my cock was encased in Mistresses dirty panties. I would still smell her juices in my nose as we parked the car and slowly ascended the stairs. Like the true gentleman that I am I let Mistress go first. In reality I just wanted to watch her ass and legs pound out those stairs as we walked to the third floor. I unlocked the door and walked in to begin kneeling to receive her leash. You were naughty Slut staring as my ass and watching me. Weren't you? Yes Mistress I was. Good don't stop being bad slut, it gives me pleasure. Now strip from those clothes and keep my panties on, I will get you a bigger butt plug.

As I crawled to the bedroom Mistress was fondling her nipples and had her riding crop in her hand. I want to see your ass red slut. Watching my ass without my permission. Twenty-five swats later, I was feeling that warm glow of inflammation spread to my cock. Thank you Mistress. Make sure you screw up again; you have an ass made for spanking and fucking. Thank you Mistress!