Hello there, this is my first story I have really written for people to read and to understand what type of fantasies I have. Also there will be some spelling errors that I will have to work out. I am a crossdresser and I have not come out about it yet. But I have always wanted to entertain some guy and have him enjoy himself. SO for my first story about one of my fantasies here it goes....
So as I dressed up in my Halloween costume I looked very much like a chick. The only thing that gave it away was the facial hair and well the adams apple and the hair. I kept it short and never really planned on growing it out. But sadly I knew I was not passable and that Halloween had passed. So now here I was without
a purpose to wear this costume I had spent money on. If only I had a wig and maybe some shoes. The costume had come with a blue and white dress and some knee high stocking. I had a black bra that made it look like I had cleavage. Also I would wear any of the panties one of my roommates had. Well I stood there and the costume
just felt so good and I was horny. Well crap how am I going to deal with this. Is what I thought to myself. So I grabbed my cock and did what any horny person would do and played with myself. When I was close I stopped and remembered I had something to help me get off with. I went to my closet and pulled out a old bag I had.
Inside I found what I was looking for my old five inch vibrator. I stuck it in my mouth and sucked on it and that got me even horny. It also made me wish I had a real cock in front of me. Yes I had never sucked off a guy but I wanted to now. But after I sucked on it I grabbed my tube of lube I had in there and put some on two fingures and rubbed some on my ass and inserted them. Oh I was tight but I did not care. SO I fingured my ass then I grabbed the vibrator lubed it up and inserted it. Oh it felt good. But sadly it was not really what I want. So I kept fucking myself with it and after sometime I turned it on and it felt so good. Soon I was
cumming all over the place. After I had cummed I cleaned up realized I wanted more but I did not have anything else to really fuck. Then my mind wondered and I wanted a cock for real. So I went online and looked for men wanting crossdressers like myself. I did not find many men but I did find places to place ads to find friends or people that wanted to have fun. So I put a add up titled "CD looking for a daddy for first time". I explained I wanted a older gentlemen to have fun with. that I was new to crossdressing for someone else and that I was not passable. I also said what I wanted. I wanted a older man that I could dress for in private and discreetly.
Also that I was not ready to come out of the closet just yet about this. That we would have to talk for a week or two before I was comfortable meeting somewhere in public. That we would meet as guys and I would chose the place. Also explained that I worked and was usually available on weekends and that there was not way on getting around that for now. I also stated that I only had the one set of clothes which was the costume with knee high stockings but was looking to expand what I had. Also they had to host and send stats and a pic of their cock or face or both to be considered and to live twenenty mins away at the most. Also if they wanted to help increase what clothes I had. They would go to the front of the line. Also said that I had pics of my ass but nothing of me really dressed up and none of my face. You know this being discrete and everything. So I posted it and some guys sent me messages but none really clicked as being the guy that I wanted to do this the first time
with. Finally a guy did. He stated he would be my daddy and would be happy to talk and get to know each other and that we could meet when ever I was ready. He also said he was in no big rush at all. So we talked and I soon found out his name was John. (I know John is such a common name but hay this is a fantasy after all). Well I
introduced myself as V. That way he can call me a girl name when dressed and as a guys name when we meet. So we talked and he agreed that if he liked where this could lead he would help me get somethings to dress up in and he would keep them for me or I could keep them. So after a couple of weeks we finally decided to meet up at walmart.
I drove there in my truck and waited. Now I was nervous but I knew I was in control for now. Soon I saw his vehicle pull up right beside mine. I got out and we both exchanged greetings. Soon we where walking through walmart just talking. He asked what I liked to dress up in and what my stats where. So I told him that I was five foot eight and weighed only a hundred and thirty pounds. I also told him the bra I had was a 36 D and it gave me the look like I had cleavage. That I had a size eight in panties but they seemed a little big. Well we walked through the girl area and he pointed things out and I told him what I did and did not like. Well in the end he found out I liked
mini skirts, corsets, tights, thongs, and pantyhose. So you could say I like to look sexy and slutty. After we walked through walmart and went back to our vehicles. We parted ways. I got a message on yahoo soon after saying he wanted to meet again and that this time maybe I should bring my stuff with me and that he would have a surprise for
me. He also asked if I found a wig for my costume. I told him yes. He asked to see it so I sent him the link. He replied wow that is nice. I stated It is cheap as well but I do not have the money right now to get it. Well we talked more that week and agreed to meet again at the same place and same time that night. So the night arrived and
I had my things in a bag. He soon arrived and said well lets talk and if you want we can go back to my place or get a room for the first time. Well we walked through walmart and talked and he pointed out some stuff that he thought I would look great in. Soon we where at our vehicles and agreed to go to a hotel first. We soon arrived and he got the room. He led me to the room and opened it and told me here is something for you. He handed me a amazon box. He said I hope this makes you look good but do not open it here. Open it in the room. So we entered the room and I opened the lid. Inside was the wig I had looked at and wanted. It was a blonde alice wig with a black headband. I looked at him and said I will go get dressed and try this on. So I went to the bathroom and stripped and took my clothes out. I had shaved at home so there was no facial hair on my face. I put the bra and stocking and dress on and I took a deep breath. I then picked up the wig and put it on as straight as possible and looked in the mirror. I looked pretty dam good. All I would need now was makeup but I did not have any. I walked out and he looked me up and down and said "Dam you look pretty good in that dress. I might also have a problem here." I did a twirl and sat beside him on the bed. As I did I said "I do not know how to repay you." He said you can figure a way to my little princess. I then leaned in and kissed him on the lips and took a hand and ran it across his lap. Oh he was hard and I could tell. I looked at him after I broke the kiss and said "I think I know how to repay you." I then started kissing him again and undoing his pants. As I did this he grabbed my ass and played with it a little.
Soon his pants and underware where on the floor and out sprung his nice cock. I leaned over and started kissing it and he moaned. "So this is the first cock you have ever sucked?" he asked me. I looked up and said yes then went back to kissing his cock and licking the head. Soon I started putting it in my mouth and sucking it. The more I sucked it the farther I went down. I did not get it all that first time but soon he was moaning and saying "I am going to cum." I stopped sucking and got on my knees and jerked him off onto my face. It caught all over me. I then went back to his cock and started sucking him off even more. This time I was going to have him cum in my mouth. After a couple of mins I felt his cock twitch in my mouth. I knew he was close so I started playing with his balls. He soon yell "Oh shit here it comes!" and a big wave of cum erupted in my mouth. I tried to swallow but could not keep it all in. I looked at the clock and realized it was late and had to go. He gave me a tap on the ass and said "Ok, but next time I am playing with your ass." I looked and him and told him "Sounds like a good plan." I then changed back into a guy and we went our separate ways. He allowed me keep the wig. I dressed once I got home and sent him some pics. In one of his replies he stated "There is my cum Princess. Next time we need to have more fun". I replied "You treat me like this you can take my ass cherry and I will be your slut". He agreed and we talked some more. Sadly work got busy so we could not have a night of fucking like we wanted. But I did blow him from time to time. Soon we just meet at his place and when I walked in I would dress up and I would blow him and eat as much cum as I could. I would even do it after work when I could. Well the next time we had sometime came and well that is for another part of this fantasy you will have to wait for.

10087   1 9283    +7.13 [32]