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  1. #1

    Join Date
    Dec 2018
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    Anna James Valentines for Cherise . 3

    Anna James Valentines for Cherise

    Pre-plan

    Valentines Day was fast approaching, and I was looking to see what could be done. Cherise had been very nice, and I felt that maybe I could do something for her on a special day. There is something about doing something for others that makes an impact on me. Especially for some for who is struggling.

    Cherise as like a living train wreck and her stories would always break my heart. I knew she lived on her own with her dogs and she had challenges with her landlord. She had a young lady who she tried to help but that young lady saw Cherise as an easy mark and would steal from her.

    Cherise no matter how challenging her world was she always seem to find a way to come to my rescue as others attacked me and I was coming off a longer 18-month adventure and I had a hole in my Vancouver play ground. I did manager to fill the hole with my European providers and a few out east. But my west coast trips would bring back the addiction I had with a provider out west. So, there was Cherise as I got band from one board after another. Cherise took up my sword and defended me.
    I thought her kindness should not go unnoticed, so I decided I should try and do something for her. On one of our email exchanges Cherise indicated that she felt bad as she was like me. She had no friends to speak of and she often wished that she had a few girl friends to hang out with.

    I had an idea. What if I set up a day for Cherise? I could set up Anna James who worked as a stylist during the day and a SP at night. I would hire her to put on a special event for Cherise. The day would consist of meeting for lunch having a day out with the girls. Ms. James would bring her best buddy and they would treat Cherise like one of them. I would hire a car service to pick them up and take them out for a nice lunch together. Then they would stop and do some shopping for dresses, shoes, boots, and handbags then out to have a massage as well as a pedicure, manicure and then go get her hair done and her makeup done.

    Once done they would then bring her out to a special Steak house where I would have a private room set aside for us and in the room, it would be filled with flowers and candles as well as music and Cherise would tell me all about her day.

    I contacted Anna James and she loved the idea and she had a perfect friend to spend the day with. In addition, I would give her a budget for the salon services and for the clothes boots, shoes and accessories.

    I was all set and the day arrive.

    I could secure a car service to pick up Anna and her friend then meet Cherise. Once Cherise was picked up the ladies were whisked off to Giraffe Restaurant for a spectacular lunch together. They laughed and swapped stories about Dickson as well as a few other stories I am sure. I was told there were many jokes and sad stories shared with each other. I wish I could have seen it. As the goal was to bond. As the lunch came to an end I had flowers delivered to Cherise at her table. I was told that when she read the card she nearly cried.

    Now they were off to Guildford Town Centre and the ladies went on a hunt. The first store they hit was set awaiting Cherise and they had several dresses selected for her. She tried on dress after dress with Cherise’s new best friends giving commentary until a few dresses were selected. As Cherise was handed the bags for her dresses Anna gave her an envelope and in there was a Valentine’s card from me to her. She read it and smiled. Then they went next door to try on shoes and boots. A few pair of boots were selected to go with the dresses. Once again once Cherise got her bags Anna handed Cherise an envelope with a Valentine’s card from me only now it was accompanied by flowers.

    Now they were off to have a massage followed by a foot massage then a pedicure and manicure ending with Cherise having her hair done and her makeup completed. At the end of each service Anna handed Cherise a card with a special note from me with the hope that Cherise would be my Valentine. Now they were off and Anna informed Cherise that she was going to have dinner at a very nice steak house. The car service dropped off Ms. James and she came into the private dining room to share with me the day in her eyes. She dropped off the receipts and details for a verbal 360. It was Lovely to hear Cherise had an amazing day.

    Ms. James now left and went to get Cherise. Cherise was still in the car and Anna went back to tell her that her day was over, but her night was just beginning. Anna told Cherise that I was awaiting her arrival. Cherise was so excited and had the thought in the back of her mind, but she did not know for sure. She had hoped that I would be awaiting her at the end of the day but now it was happening.

    Two ladies from the restaurant greeted Cherise and assisted her with her gifts to bring into our private dining room. Before she entered she hugged Anna and her friend and thanked them for an amazing day. Cherise now turned and entered the private dining room carrying her flowers followed by two of the young ladies from the restaurant carrying all of Cherise’s treasures from the day. Upon her walking into the room filled with flowers and candles and Frank Sinatra’s “The way you look tonight” Cherise gave me such a kiss and such a hug. She held me so tight I never thought she was going to let me go. I was enjoying it. It was obvious that I had touched Cherise in a very special way.

    She looked so good and her smile was a mile wide. She was a bundle of energy and shared everything from the moment she was picked up until the moment she arrived. She then sat, and we ordered appetisers and the storied flowed like a Rocky Mountain avalanche. I loved how she pulled out outfit after outfit and the boots and how she just had to try on the boots. She would take a breath here and there and then give me a big kiss and a hug.

    We had the main course arrive and we ate, and she looked around the room and saw the flowers and the candles and cried. She told me no one ever did such a thing for her before. I was so happy that I could stimulate such emotion in her. I told her she looked so beautiful and she tried not to let her tears ruin her make up. We dance to “something stupid” and as the song came to an end she looked me in the eyes and told me she loved me. Those words gave me an instant hard-on. She could feel me stiffen up and when dessert arrived Cherise asked if we could go back to my place.

    I told her she did not need too. But I had hoped for this and I handed the last card of the night to her and she read it and hugged me and cried. She told me I did not need to pay her for the day and certainly not for the night. I told her that was not part of the deal.

    Cherise now needed to use the bathroom to clean up her makeup and I needed to settle things with the restaurant. My driver assisted with the packages going back to my Penthouse. I gave the restaurant a good tip and we were now off with all her gifts and her flowers as well as the candles and her in my arm.

    In the back of the limo Cherise held me and kissed me and told me she wanted me so bad. I was impressed with her approach to the whole event and I was pleased that it went better than expected. Cherise was not going to let me forget how much she appreciated my effort and I loved how she showed her appreciation. As we settled in the back-seat Cherise wanted me to know she was not wearing any panties and she had a special gift for me, as it was valentine’s day for me as well as her.
    As we cruised through Richmond on the way to the hotel, Cherise was caressing my body and our lips were locked on each other and our hands roamed over each other’s bodies until her hand stopped on my crotch. She massaged my manhood through my pants and I was responding as she had hoped. She purred in my ear as I got harder for her. I wanted her, and she knew it and my hands massaged her breasts and I wanted to rip the new dress and coat from her body. She smiled thinking of such action on my part.

    Thankful for that fact that my penthouse was not far as we reached my place we were both panting like wild animals in heat. Cherise knew that round two would take place in my penthouse. When we arrived we gathered her things together. As we awaited the driver to open the door I could see the idea of us making mad passionate love in the suite dancing around in her head, as my head was spinning with thoughts of her naked body next to mine.

    We escaped the limo and I gave the driver a nice tip after his day with Cherise. My driver smiled at her as we unloaded the limo. He helped us with the bags into the building and I thought he was looking for a kiss from Cherise as he put down the last bag, but he settled for a smile from Cherise as she turned her attention to me. She had a strange look on her face as we loaded all the gifts into the elevator and I push the button taking us to heaven. At least for the night.

    Cherise came to me to kiss me once more and I enjoyed her lips on mine. However, we had reached the 18th floor and it was time to haul out all her gifts into the hall way and then down the hall way to the suite. I opened the door and we drop bag after bag into the suite’s hall way.

    As I dropped the last bag I turned to see Cherise naked before me now only in a pair of black stay ups and her new boots. She nearly flew into my arms and she was quick to tell me she wanted me, and she tussled with my suit and my clothes but managed to get me more naked than her. We kissed, and we fondled each other, and she pulled out condoms out of her new handbag. I told her not here and took her by the hand to take her up stairs to the bedroom. We fell on the bed and we embraced. Kissing and holding each other. I was so hard now, and she was so wet. She took my cock in her mouth and began to give me a rough bbbj. I had a hard time enjoying it as my dick was manhandled by her teeth. Now I am not sure if it was because her mouth was too small, or my dick was too big, but it was not a pleasant experience and I think she knew something was not as it should be.

    We move to plan B as she ripped open the condom and fumbled to put in on me. It took a few tries and I needed to assist her. However, it was now on and she laid back giving herself to me. I was now on top, concentrating on her eyes, as I rubbed my thickness all over her wet slit. Up and down I went, and she seem to enjoy my using my dick as her dildo. She wanted me to go faster and faster so I stroked her using my dick until she came, and she grabbed me and pulled me closer. I could feel her breath on my neck. She whispered that she wanted me, but she wanted me to go slow.

    I took the tip of my dick and slowly slid it in her, but it seemed clumsy as I could not find the entrance to her love box. At one point she told me that was her ass. She told me it was ok but that was her ass. I pulled out and realigned and now I was in position. I could feel my tip now entering her and I could feel her tightening up. So, I pulled out and then pushed in again. She whimpered so I pulled out and then tried again. She commented in a hushed voice that I was so big. I could feel that her pussy was not able to take my girth. She tried, and she held her breath wanting me but as I slid in once more and penetrated her kitten she cried out into the night. It was a screech I hope I never hear again. I pulled out and told her that maybe it was not a good idea.

    Cherise then told me maybe doggie would work better as she liked it from behind. Personally, this was not my favorite as it is so impersonal, and I do not get to feel a rush from my partner. However, in this case maybe this might work. So, she kneeled on the bed and presented her ass and her pussy to me. I aligned up behind and brought my cock to her cunt. I tried to enter her, but her love box was not able to accept me. I pushed, and she tried to accept me but no such luck. When I finally found her hole my girth caused her a great deal of pain. I pulled out and we both realized that this was not going to work.

    Cherise offered to take me orally, but the memory of her teeth quickly reminded me that it was getting late and maybe we just needed some sleep. Cherise was disappointed and told me with time she could take me, and it would not be a problem. I asked her if she had a good day and she said it was the best day ever. So, then why spoil it by me putting my pleasure above hers. She agreed, and we used the washroom to brush our teeth and for us to get into bed together.

    We cuddled up and she told me she could learn to like me. I told her she was amazing in so many ways and she wanted to believe it, but other things were at work in her mind. In the morning we sorted her boxes and we consolidated the gifts so that she could get the packed gifts into a more manageable level.

    My driver arrived after breakfast and Cherise was on her way. She asked if we could continue to communicate and if I would see her again. She kissed me and with tears in her eyes she told me I was the most amazing man she ever met. I wanted to believe that but well my mind was working over time as well. It was time to go back to my real world and to make that world work for me.

 

 

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