Working as Hostess Part II

I got a call from Amber, my ex girlfriend who got me into crossdressing, a couple of days before New Years saying Caroline was looking again for some help hosting for New Years eve. With New Years eve being a Saturday night she was expecting a huge crowd. Amber and I had already made plans to go out bar hopping that night, dressed of course.. Amber and I had been going out once or twice a month for the last couple of months. Our relationship is a strange one. We sometimes go months without seeing each other then other times we do a lot together. Its probably I'm her go to when she is not seeing someone else. I guess that's fine with me because when we do get together we usually have a blast and the sex is great. We talked about would we rather go out or go help a friend. I had just bought a new outfit to go out New Years eve. Its a black skirt and black and a silver and black blouse and some silver hi heels. I will have to say I look really good in it. I have been training for a half marathon recently and have really toned up. With all that being said we decided to go help Caroline.

Amber and I decided that since we would be working New Years Eve that we would go out the night before and have a little fun. I went over to her place Friday after work to get ready. I took several outfits not knowing what she was wearing or where were going. Once I got there I needed to go for a training run for my half marathon. I told Amber to go ahead and jump in the shower and I would be back. I did a quick 6 miles and got back all hot and sweaty as she was getting her makeup on. I jumped in the shower. I started to shave my legs and other areas. Its a weird feeling that I get knowing I'm about to go into my feminine mode. I have just start feeling feminine and my voice and mannerisms change. Its really hard to explain. I get out of the shower and slip on pair of panties put my silk robe on and it feels so good. I sit down to let Amber apply my makeup. She does such a good job and she should being a cosmetologist. As always I am really getting aroused as my transformation is taking place. Once the makeup is done and the wig is on its like I'm a totally different person. Generally at this point she knows I'm all worked up and give me some relief. She told me took me into the bedroom and gave me my new silver heels to put on and she said would be right back.

I stood there in front of the mirror checking out how the heels looked and really getting worked up. She cam back in with a smile on her face that I recognized. She opened her robe and she had on her strap on. She told me to come over and get on my knees and suck it. I sucked it and started to rub myself. She told me I couldn't do that so I stopped. After a few minutes she told me to lay on my back on the bed. She pulled my thong to the side lubed me and started to put it in. It didn't take long before she was all the way in and pounding me good. It felt so good with my legs up in the air with the heels on. My cock had never been that stimulated. It felt so swollen I was leaking precum like never before. I went to rub it but she slapped my hand away. She stood me up and bent me over and starting fucking me again. My sissy cock was swaying in the wind as she thrust. She finally layed me back down and pulled my panties down. She told me that if I wanted her to let me cum I would have to be her sissy all weekend. I was thinking we have never done that but it could be fun plus I was about to explode. Of course I said yes. She smiled and reached to stroke my cock and on the first stroke a shot a load that about hit the ceiling. I have never cum as hard or as much as I did then. I laid there for ten minutes in just a euphoria. I finally got up and cleaned up. She came up and hugged me and I whispered to me that she was serious about being her sissy that weekend. I told her sounds like fun if its anything like we just had. More to come...........