Dress and DrivebyTrinni69©
I am twenty four years old and have been cross dressing for years now. I started when I was young and when my sister was not at home. Since then I have moved into a house of my own and I have built up a pretty large collection of clothes, shoes, make-up, and a few different pairs of fake breast. I don't have to worry about wigs because I have the kind of long wavy brown hair that most girls wish they had. Actually I get mistaken for a girl from behind all of the time. That also might have something to do with the fact I am only five seven and my weight is one hundred and thirty five pounds. I also have an advantage over some cross dressers because I naturally have a pretty face and very little hair grows on my face and body. The only thing I have had to work on is my voice.
I work out of my house on my computer so I get to spend a lot of my time dressed up which gives me plenty of time to practice my voice. Even though I have this opportunity, I'm not sure if I could pass because of my voice. That is the reason the only way I will go out dressed is when I dress and drive. I read about doing this on the internet and I decided to try it. Since my first time, I have done this fairly frequently. Sometimes I go out dressed down and other times I go out like I'm trying to get picked up at a club. I love it because my heart is pounding most of the time from the mixture of excitement and fear. I have never exited my car because I have never had enough guts to get out.
This all changed last month by a twist of fate. It was in the middle of the day and I was stopped at a light in a very nice neighborhood. All of a sudden I felt my car get hit from behind and I jolted forward. I completely forgot I was not only dressed up but I had one of my sexiest outfits on. I was wearing a tight black dress, fishnet stockings and black high heels. I had red lipstick on and looked like I was ready for action. After a second, I opened my door and started to step out to check out the damage to my car. Once my heel hit the ground, I remembered how I was dressed.
Before I could do anything, the guy who hit me ran up to see if I was okay and he had a worried look on his face. "I am so sorry. Are you okay?" He looked like he was very athletic and had the face of a model.
I tried to give my best female voice and replied, "I think so."
Then I noticed his face changed a little bit as he put out his hand to help me out of the car. I became very nervous and told him I didn't care about the accident and that I must be going. He advised me there was a good amount of damage and we should exchange information. I tried to get out of it but I think he could tell I was afraid to step out into the street. He looked at me with a calming smile and advised me he only lived a few blocks away so we could go there to exchange information in private. I agreed and followed him to his place.
After following him for a few blocks we pulled up to a fairly large brick house with a long driveway which curled behind his house. I parked behind him and as I opened my door he walked up and took my hand helping me out of my car. By the expression on his face I think he could tell I was a guy dressed like a girl. We looked at the damage to the cars which was not as bad as I expected. Then we walked to his back door and entered into a beautiful kitchen. While I looked around he offered me something to drink. He had a way about him which made me relax even though this was the first time I have ever been dressed up in front of anyone. I agreed to have a drink and he surprised me with two Tequila Sunrises. We sat and talked for a while about everything except the accident and that I'm a guy in women's clothes. I found out his name was Jake but he goes by the name of Bo. I told him I go by the name of Susan and didn't even mention my real name. He made me feel so comfortable and relaxed, I was really enjoying myself.
After a few more drinks, I had to use the bathroom. He told me the down stairs toilet was not working and I would have to use the one upstairs. Being a bit drunk, I missed the bathroom in the hall and went into the bathroom attached to his bedroom. It surprised me how neat both the bathroom and his bedroom were. I had to un-tuck my cock so I could use the toilet. I felt a bit wobbly so I sat down. Next to me on my left side of the toilet was a basket of magazines. On the top was a Sports Illustrated but underneath those were a bunch of bi-sexual porn magazines. I was surprised to see those magazines and the pictures got me horny as hell. When I finished going to the bathroom my cock was too hard for me to re-tuck. I was drunk enough at that point so I just stood up and pulled my panties up and pulled my dress back down which did not hide my hard cock. I stepped out of the bathroom and Bo surprised me by standing in his room with a smile. He looked at my crotch and asked if it was his reading material or himself that got me so excited. I blushed, lowered my head and I told him it was the pictures but if he wanted to show me what he looks like naked I wouldn't stop him.
As Bo started to undress he asked if I had ever been with another man. I told him no but I have sometimes fantasized about being treated like a lady and sometimes like a slut. Now he was completely naked and as he walked over to me he told me he could not only make me feel like a slut, he could make me feel like I died and came back as the porn star Vanity. I just stared at his cock which must have been almost eight inches long and was not fully hard yet. He looked very powerful with all of his muscles and tight abs.
He pushed me to my knees and said, "Wrap your luscious lips around my cock".
I kissed the head of his cock and I couldn't believe how soft it was. The head felt like a super soft sponge on the end of a semi-hard stick. I have sucked a lot of different kind of dildos but nothing felt like this. I couldn't believe for the first time I was cupping a real set of balls with my hand and starting to work my mouth down and up his hard shaft. Sucking on my first real cock made me extremely excited.
Each time I swallowed him it made me feel so much like a slut I took him a little deeper. I got to a point when his head got to the back of my mouth I thought I was going to gag. I slid my lips back to his head and swirled my tongue around it to tease him. I could tell he was enjoying what I was doing but I think I enjoyed it more. By the sounds he was making I started to understand the power a good blowjob can have over a guy. Then I took my time and worked my mouth back down his cock. I took him to the point where I gagged but this time I was able to handle it. Then I pushed past that point taking his head right into my throat. I continued to caress his balls with one hard and jerk the base of his cock with the other hand. I reached down with one hand a started to jerk myself off but he wouldn't let me. He told me he would make me cum harder than I ever had before but not until he said I could.
Then I grabbed his ass with my hands and squeezed tightly as I started guiding him in and out of my mouth and throat. I picked up the pace and as I pulled him into me, I slid my lips down his hard shaft. I then worked my lips back to him head and I continued taking him deeper and deeper until he was hitting the end of my throat. I knew from dildos with a little effort I could push his head past that point. I could tell he was tensing up and close to cumming. I then pulled him in a little harder so the head of his cock went past the end of my throat taking all of him in. When I did that he let out a big moan and started cumming. I held him in that position as he came. It was a very strange feeling having my mouth and throat full of cock as he exploded into me. I gagged a little as he pulled out and I couldn't believe how much I felt like a real girl at that moment.
He smiled and looked down saying, "You must have been practicing your whole life for this moment to be able to take all of me down your throat the first time. Now it is time to take you to the next level. Turn around so I can remove your dress and see what you look like under those clothes."
I turned around and moved my hair off my neck so he could get to the zipper. As he slid the zipper down my back he started kissing the back of my neck which always drives me wild. He continued this as he slid my dress off. Once my dress fell past my waist and onto the floor, he undid the clasp of my bra. As I removed my bra he gave my breast a good squeeze. Bo let go of my breast, slid his hand down to my panties and took them off. I turned back around so he could see what I looked like in just my stockings and heels. He looked me over and told me he liked what he saw and he could not wait to take my virginity. Then he had me walk to his bathroom and get on my knees so I could get cleaned out. I got on my knees and placed my shoulders and face on the floor. He told me he has his own enema mixture and it might fill me up more than I am use to but it will clean me out real good and make the sex that much better. I was told to meet him down stairs after I finished getting cleaned up. I found him standing in the living room with a shot in each hand and his cock hanging low. After I did my shot, he had me get on my knees and get him hard again using just my mouth. It didn't take long for Bo to get rock hard and I loved how it felt having his cock grow hard inside my mouth.
When he was ready he stood me up and turned me around bending me over the arm of his couch. As he was bending me over he grabbed my dick and guided it so it was pointing down between my legs. I was at the bent over at perfect height for my feet to just touch the floor when my legs were spread. As my face hit the couch I noticed I had just appeared on the TV screen in front of me. As I was looking at myself, the screen changed to a shot of my hard cock, legs and ass from behind. I stared at the screen and saw him start to lightly tease my cock and then apply some cold lube to my ass. I loved watching my ass as I felt him slowly ease his thick finger into me. I was glad he took his time and started easy only sliding one finger in and out. The screen faded back to my face and I gasped as he added a second finger. When the screen switched back to my ass again Bo took three fingers and began not only working them in and out of my ass, he started twisting his wrist to ream me out a bit. I loved what he was doing to me but I was afraid he was going to fist me. Then he pulled out and he told me to grab my ass cheeks and spread them for the camera.
After I held my cheeks apart for a few seconds, Bo slowly started to shove his cock into me and before I knew it he had worked his cock in my ass until it felt like I couldn't take anymore. I moaned from the pain and then he stopped and held that position. While I tried to let my ass relax around his cock, he started telling me how much of a hot slut I was. Hearing him call me a slut just turned me on even more. That's when he grabbed my hair with his left hand and pulled towards himself so my back was completely arched. If I had not pushed up off the couch with my hands and arms, it would have felt like my hair would get pulled right out of my head. Bo started sliding in and out making sure he never let his cock exit my ass. He went a little deeper each time and I watched my fake tits bounce on the screen with each forward thrust. As he picked up the pace he started to slap my ass with his right hand. He was slapping me hard and between the stinging on my ass and being penetrated deeper than ever before I was experiencing a strange mixture of pleasure and pain. I was shocked when I realized he was shoving all of his cock in my ass and his balls were slapping my balls with each trust. I was moaning each time he hit bottom and he kept right on pounding my ass until we were both pouring with sweat. Even with the sweat stinging my eyes, I couldn't stop watch myself getting fucked on the TV. I have had fantasies about being with a guy but it was not even close to how good the real thing was.
He told me since he didn't let me taste his cum the last time I sucked him off, he was going to cum in my mouth and all over my face. He then pulled out of my ass which made me feel empty and wish he was still fucking me. Before he walked around to my face I had to spread my ass cheeks again for the camera so I could see my gapping asshole. Then he surprised me by sliding a butt plug into my ass before he walked around the couch and started fucking my mouth just like he fucked my ass. He gave me a little time to get use to it but in no time his balls were slapping my chin as he slid in and out of my mouth and throat. After a few minutes he pulled back to where only the head of his cock sat inside my mouth. Just then he started to unload, and filled my mouth up before he pulled out and finished cumming on my face. I swallowed as much as I could but some spilled out and ran down my chin. I looked over at the TV screen to see cum dripping off my face and my make-up smeared from sweating so much. I looked like a whore who had just had the fucking of a life time. I rolled over the arm of the couch so I was now sitting with the plug still in my ass and facing the camera. I stroked my hard cock and asked him if I was finally going to get to cum. He grabbed my hand and while he removed it from my cock, he slid a cock ring all the way down my shaft to my balls. Then he smiled and told me the day was not over yet and I would just have to wait until I was truly ready.