This story involves Cross Dressing and some sexually explicit material, if you are under the age to legally read this in your area please go no further. If you are old enough please enjoy. This story is totally fiction, any names or actions are totally coincidental.
Its been a while since I have written a story. I hope that this one will be of the same calibre as the others I have written. I hope you enjoy. If you want to contact me my email address is at the end of the story. Please no hate mail. Enjoy Cris.
A Strange Fall Day: First Meeting
I have been thinking about this day for a while. I cannot believe that it is really happening. My first date with a guy who really likes me for who I really am. Ok so you are probably wondering what this is all about well let me begin with a little of my past. At a young age I started dressing as a girl which would be all nice except that I am a male. Well over the years I have tried everything in my power to dress up and stay slim and grow my hair long much to my parents dislikes. So I started going to the store once I was old enough to drive and buying my own clothes that I could have for my very own and no one would miss. I started out with panties, bras, and then different outfits. I did this for several years buying a little at a time. When I got to college I wanted a place to myself whether is be a dorm room or my own apartment. Well I had to start off in a dorm room where this story really started to take place.
It was a warm day in the fall and I was walking around campus in a pair of shorts and shirt and under it I wore a pair of panties. Well a guy came up behind me and apparently saw what I was wearing. So he came up to me and started talking to me. He introduced himself as Paul. Then my heart sank as he said that he liked my panties. I couldn't believe it, at first I thought that he was going to do something to me and possibly hurt me but he didn't. He seemed caring as he put his arm around my shoulder as we were walking. He wanted to know more about me and what I am doing. And also if I had any thing else to wear. I said I did. I was curious as to why he was asking me all of these things which I would find out later and so will you.
He asked me if I had lunch yet and I hadn't so he invited me to a small restaurante on the edge of campus so that we could talk. He told me that he was gay and had wondered how he could be with a guy but look like he was with a girl. I had all the characteristics that if I were to go with him on a date I could pass as his girlfriend instead of his boyfriend. Although I didn't consider myself gay I did have a tendency to enjoy the male anatomy. Plus this also gave me an opportunity to dress and be with someone who knows what I am and would protect me. I thought it would be fun and also go out dressed. He was a little nervous to say the least. After eating I invited him back to my room to show off for him. To which he accepted.
When we got back to my room I sat him down on my bed and I sat next to him. I asked him what he thought about guys who dress as girls. He gave me the answer what I thought he would. He thought that even though that while dressed he would know what is under my clothes and he thought that he can kill two birds with one "girl". So he asked me about when I started dressing and what I feel like when I do dress. I told him that I started a long time ago and what I did to get the clothes that I now have. I also told him that I feel like another person when I am dressed up, that I actually feel like a girl getting dressed in the morning trying to look my best. He asked to see what else that I had in my closet. I told him that I could put on a small fashion show for him if he had the time. He did, so I told him I would be back in a few after I had changed. I first changed into a short denim dress that came down to just above my knees. With a red shirt with a red bra with matching panties. I also put in my false breasts that I had only gotten about a month before.
Paul seemed to enjoy this first outfit and said that it suited me. Although I wasn't wearing any make-up at the time I still looked like a natural woman. He asked if I had anything that I could go out on a casual dinner date and then dancing. I said that I did, but I wanted to save it for when he was ready to go out to give me time to get ready. Before he left I gave him my number so he could call when he was on his way to pick me up. On his way out the door I gave him a quick peck on the cheek and said that I would see him at Eight. And off he went to get himself ready. I went back and picked out a black skirt that came down to my knees with a white turtleneck blouse with short no sleeves. I also chose a matching pair of black bra and panties with garterbelt, hose and two inch black heels. Once I had everything ready I went to take a bath with only 4 hours until the date I had to work fairly fast but wanted to take my time. I then proceeded to shave my body while I was in the soft suds of my bubble bath.
After spending an hour in the tub I took a short shower to wash my hair to make it as soft and flowing as it can get. I got out and started to dry my hair and curl it. When I was back in my room I saw that I had only a couple of hours left to do my make-up and get dressed. So I glued on my false breast. Then I put on my bra which was over flowing with lace on it. Then on with the garter belt and stockings. Then my matching panties and then tucked my penis back between my legs to get me a smoth line. I sat down and started on my make-up. First put on some eye liner and mascara. Highlight my cheekbones and then paint my lips with red lipstick. I paint my nails a matching red. I finally had a little time to relax before I had to finish getting dressed so I took out a cigarette and lit it up and laid back went to my computer to check my mail. Only a couple of things from school of what was going on that week. I looked at the time and saw that I only had about half an hour before Paul would be back to pick me up. So I decided to put on my skirt and blouse. I went and got a purse and put some cash my ID(which I hope I wouldn't have to use) and my make-up. I sat down and had a cigarette while I waited. I always loved the way my lipstick looked on the tip of it.
When the time came Paul came to my room and knocked I opened the door and he seemed surprised at how good I looked. He led me out of the dorm and to his car that was parked nearby. He took me to a nice chain restaurant where he ordered for me(how sweet). He kept asking me how I became like I was. And I kept saying that I will tell him just not there. I think he understood and we just had a good conversation on classes and what we planned on doing with the rest of our lives. I think he wanted to live with me or something like that. But I know he wanted to know if we could really be boyfriend and "girlfriend". I could read it on his face. After finishing our dinner he ordered us a couple of drinks while I smoked a cigarette. He didn't like me smoking but he was OK with it. Once we were finished he took me to a cozy dance club. Not too many people were there and we just danced the night away. Slow or fast we were on the floor dancing. He was a wonderful dancer and lead me around and showed me off.
When we left there we went to the park and walked around and sat for a while. Once when we were sitting he leaned in close to me and gently kissed me on the lips. I liked that I had not been kissed like that for a long time. We sat there looking at each other in the eyes and one thing lead to another. To which we started kissing he offered me his tongue and I offered mine it was getting hot and that wasn't from the air. We went back to my place to sit and talk for a while I could see that he was getting hard and Paul could see that I noticed this and asked if I might want to go a bit further than just kissing. Did he just read my mind or was it a mutual feeling about this. Once he said that I got right on his lap and kissed him hard. I could feel his cock on my back side like it wanted to get out. I eventually slid off his lap and onto my knees. I helped him out of his pants and underwear when I saw the best cock in my life. It was 7 inches and thick!!! I leaned forward and kissed the head of it. I looked up at him and he was smiling with his eyes closed. He put his hand on my head in an affectionate way. I then proceeded to give him the best BJ that I could with my limited experience.
He seemed to be enjoying it, he was moaning and groaning as I continued to give him head. After about 5 minutes he said he was about to cum. I couldn't wait so I started sucking more just to make him cum. He then came in my mouth I am not sure how much, but it was more than I have ever done myself. After he was finished I went up to kiss him and he darted his tongue into my mouth to taste his own cum that was left. I really was enjoying myself. I wanted to feel him up my love canal. I got up and walked over to my dresser and pulled out my lube. I put a dab on my hole and then put some onto his cock. I had hiked my skirt up onto my hips and my panties were already off. I laid him back onto the bed and climbed onto his lap. He reached up to feel my breasts which I wish I could have felt but the thought of that was all it took. I started to lower myself onto his cock until the head was just touching my hole. I slowly lowered myself further onto his cock after a couple of minutes I had the head in me. After that I would slowly lower and pull off. After several minutes I had his whole cock in me I sat there and leaned down to kiss him.
While I was kissing him I raised myself up and started to fuck him slowly wanting this to last. And last it did we were going on like 30 minutes I never knew a guy could last that long but I was loving it. Although at one point I had to relube him so we could continue and I wouldn't be as sore and neither would he. I was loving this too much. When he came he came hard again. I wish that I could see him going in and out of me, but maybe another time I will somehow. We collapsed onto my bed and fell asleep. I wish I had cum that night but I can say that I had an emotional orgasm which was just as good.
The next morning he awoke and kissed me saying he would call to see if I wanted to do anything tonight. We said our goodbyes and he left giving me another kiss on his way out.
I hope you enjoyed this story I hope to be writing a sequeal to it. If you would like to contact me you can at southerndixiegurl@hotmail.com also I encourage you to read my other stories "The Times are Changing", "College Crossdressers weekend", "A trip To The Other Side", and "Thank you Master Jones". I hope you enjoy all of these.