Trip to Florida
I was at work and they decided that some of us had to go to Florida to work on some problems so I was picked. I went home and packed and made sure to pack some of my sissy outfits also because I would be in a hotel for 7 days and have the room to myself it was perfect. The next morning me and the others met at the airport and we flew to the airport got a few cars and went and checked in to the hotel. It was a nice place with a pool so we all unpacked and decided to meet in the lobby and talk about what we had to do. I went down to the lobby and met the others and it was then I saw one of the girls that had come from another place to help us out. She was maybe 22 5’2” and around 110# and had a nice small set of tits from what I could see from her outfit. We all sat around in the conference room and figured out what we had to do and we then got into the cars and drove to the place we would be working. We started to get things figured out and organized and I noticed the girl paying close attention to me. I could see that she liked me so I figured cool I can have some fun on this trip. We decided to finish early because it was real hot and hit the pool so we all went back to the hotel and put on our suits and went down to the pool. I put on my suit and some water shoes because my toes were red like always. The hotel had free beer for guests for a few hours so we had some and cooled off and I then saw the girl come over to the pool and look around. I waved her over to my area and said have a seat so she sat down next to me in a chair and relaxed. She had on a nice bikini top but also had on shorts, so I figured damn it is that time of the month but figured oh well we have 7 days. I did notice she had very nice toes and they were red I love red toes. I got her a beer and we sat and talked and I found out her name was Sally and she was 22. She was from Ohio and lived with her parents still. We sat around for a while and then decided to go get some dinner so we all went up to our rooms and changed and met by the lobby. Some of the guys wanted to go into Orlando and get some sea food but I hate sea food and so did Sally, so we decided to just walk down the block to a little bar grill while the rest of the crew drove into Orlando. Sally and I went inside and found a nice little booth and sat down and ordered a few more drinks and then some dinner and talked some more. We talked about her job and her family and other stuff and then I asked her if she had a boyfriend? She smiled and said well I have had a few but nothing that has lasted long. I said well that is hard to believe as pretty as you are I would think they would be knocking down your door. She smiled and said well thanks and then she asked me about myself and I told her. We had a nice dinner and a few more drinks and I could tell she was getting drunk so I figured we had better quit drinking. She said I need some air so I paid the bill and we walked back to the hotel and as we walked she talked and finally she said can I tell you a secret? I looked at her and said sure what is it and she said well and she said well never mind lets go up to my room so I can get something and we can sit out by the pool for a while. I said okay and we went up to her room that was just a short distance from my room and she said have a seat be right back. She went into the bathroom and I had a seat on the chair. She soon opened the door and walked out into the room and stood in front of me in nothing but a smile. I looked at her and checked her out and it was then I noticed she had a hard cock between her legs. It was about 7” long and along with her nice 32 tits she looked beautiful. She said this is why I do not keep any boyfriends. I figured I better show you before we get to close, and I feel bad about losing another nice guy. I looked up at her and said well as long as we are being honest I want to show you something also. I stood up and said be right back and I went into the bedroom and took off my stuff. I had on a pair of nylons with garter belt under my cloths along with my red toes and I then walked out into the room so she could see me. She was sitting down on a chair so I went up to her and she smiled and said well I like it. I smiled and got down on my knees and took her hard cock into my mouth and started to suck her cock. I also started to play with her nice tits and nipples while i sucked her cock and I could tell she was loving it. She started to moan and stuff and said you better stop soon or I will explode so I took her deeper into my mouth and I could feel her cock swell up and then it exploded filling my mouth with a nice big load of hot sticky cum. I kept on sucking her and swallowed all of her cum and then got up and said now that was fun. She got up and pushed me onto the bed and took my cock into her mouth and started to suck my cock. As she did this she started to play with my nylon legs and finally my balls and then started to finger my ass. Well that was all it took and I soon exploded in a huge orgasm into her mouth that she swallowed down just like me. We both lay down on the bed and finally she said damn that was nice so you do not mind that I have a cock? I said you do not mind that I cross dress? We both smiled and laughed. I was getting horny again so I moved around and started to lick and suck on her nice tits and hard nipples and she said lets get into a 69 and play. We moved around and I took her cock into my mouth and she took mine and we sucked each other till we both exploded into each other’s mouth. We both lay down in the bed and talked and she finally got a look at my red toes and said damn I did not ever notice your red toes I really love them. I told her that I kept them red most of the time except for spring and summer because I love to walk around barefoot and people do not understand about a man with red toes. She laughed and said I bet kind of like a woman with a cock. We both had a good laugh and I put my arm around her and we both fell asleep. I woke up a few hours later with her sucking my cock again but I had other ideas so I said be right back. I went into the bathroom and grabbed the lotion and gave it to her. She looked at it and I bent over and put my ass into the air and she got the idea so she put some on my ass and got behind me and positioned her cock and slowly started to fuck me. I started to meet her thrusts and soon she was balls deep in my ass and I started to help her hammer my ass deep and hard. Soon she exploded deep in my ass filling me with a nice hot load of cum. She fell out and then bent over the bed so I used the lotion and started to fuck her ass deep and hard till I exploded in her nice soft ass. We both collapsed on the bed and fell asleep until morning and we had to rush to get to the work site on time. We kept looking at each other and smiling but I do not think anybody expected anything. We got done with work that day and went back to my room this time and we stripped and took a shower together and I sucked her cock in the shower till she filled my mouth with another nice load. she got up and put her foot on the wall and opened her ass so I stuck my cock in her ass and fucked her till I filled her ass with a nice load of cum. We both got dried off a she said she had to go get some stuff to wear in her room, so I said okay. She took off and said she would be back quickly, so I went and put on a new pair of nylons red this time along with a red and black garter belt and a pair of sheer panties. I also put on a nice open cup bra and a sheer baby doll nighty along with a pair of high heel sandals. I went into the bathroom and soon she was at the door and opened it and walked inside and I walked out into the room, so she could see my outfit. She stopped in her tracks and checked me from head to toe and smiled and said now that is a sexy outfit. She said be right back and she went into the bathroom and soon came out in a nice little outfit of her own with a pair of pantyhose nice bra and a baby doll nighty. We ended up playing all night and never had dinner but had fun. We spent the trip together and had a wonderful time. When we finally had to head home we got each other’s phone number and made plans to get together soon. She did not live that far away from me.