First Time Out

I am a 21 year old straight male and have had fantacies about wearing womens clothing. I have never acted on them and surpressed my desires to dress as a woman.

One day I was one the internet and came across a website with crossdressres on it and my desires came back. Well as I kept looking through the website I noticed a place to buy clothing. As I was looking I decided I would buy something, it was black corset, with a black bra, black panties, black garter belt, and black stockings. 

When the package arrived I went to the bathroom to take a shower. After the shower I shaved all of my body hair including public. I then put the clothing on and immediatly got an erection so I got back on the internet and chatted with other crossdressers. After the first night of wearing the clothes I thoght I would go out in public as a woman for the first time. 

I then got back on and got a black dress that came down to knees, a wig, makup, false breast that had adhesive, and tips from others on the site on how to do makeup and make myself look more like a woman. Well when the package arrived I waited until saturday to go out.

Saturday was the day so put on my panties, bra, garter belt, stockings,and dress. I then did my makeup and put my wig on it was a blonde wig with long straight hair and came with adhesive so it would not come off. 

I then got in the car and drove to a mall where no one would recognize me. As I went inside I immediatly noticed guys looking my way. I went to womens clothing store's to get more clothes. I picked up some more panties so I could start to wear them all the time, bras that matched the panties, more stockings, a couple dresses, skirts, and shirts. Before I left the mall I decided to get a cd and while I was in the store a guy started to hit on me but I've never been interested in guys so I blew him off.

I then left the mall and went back to my car and stopped on the passenger side to put my clothes in the car. I walked around to the drivers side but dropped my keys as I was about to get in the car and bent down to get them, but when I lifted back up someone grabbed me from behind and threw me in a van. 

The next thing I know I hear the driver say to one of the guys in the bback to occupy me so I don't where we are going. All of a sudden one of them tells me to come to him on my knees. I make my way to him and he tells me to unzip his pants. At this point I start to get nervous because I know where this going. He then grabs me by the hair and lowers my head to his lap and tells me to suck his cock. I didn't know what to do because I have never seen another persons cock other than on porno's. The first thing I notice is his is bigger than mine, it was about 5" (as you can tell I have a small penis). He then gets upset because I am taking so long so he yells at me to suck his cock and slaps me in the back of the head. So I open my mouth and slowly to suck. Moving my head up and down trying to do it right I hear him to start making sounds. When he started to moan I noticed my penis getting hard and realize I like it. I start to go faster as he moans and I feel him start to tense up. He thens grabs the back of my head and holds it there until he cums in my mouth. I felt his warm cum shot into my mouth and it doesn't taste that bad. He told me to swallow it all but some of it came out the side of my mouth and he told me to lick it off of my chin.

As he came the van came to a stop and the driver told him to put the bag over the slut's head. They then put the bag over my head and lead me out of the van and into a house. The bag then comes off and they all sit down. I then recognize one of the guys as the one that was hitting on me in the store. He then motions to me to come over to him. He then unzips his pants and looks at me and says you know what to do you slut. At that point I once again drop to my knees and start to suck his cock. He then starts to cum in my mouth but once again some dribbles out so as I come up out of his lap he tells me to turn around and look into the camera. They then tell me to lick it off of my chin again. The third guy then says he needs a whore to suck his cock and motions to me to come to him. He then asks me if I am a whore and I say no, then he slaps me and tells me that was the wrong answer and asks the question again but this time I say yes so he doesn't slap me again. He then looks at me then his cock so I 
then drop to my knees and start to suck again. At this point my penis is getting really hard. This time when he cums in my mouth I catch it all and swallow.

After he cums he then says he thinks they deserve a show and tells me to take my dress off. I then start to protest because I don't know what they will do when they find out I'm a male. One of them then hits me and tells to shut up and do as told. The guy with the camera walks around in front of me as I start to take my dress off. As the dress falls to the floor he notices my penis. The first thing that is said is if he want to dress like a girl he will treated like one. Then they ask me how many men I have been with and I answer with the truth zero. "I don't believe that because only whores give that good of a blow job" the one in charge says. He then tells me to take off all of my clothes so I do then they immediatly start to laugh at my penis becaus even with a hard on I am at most 3 1/2". 

They then lead me to a bedroom and tell me to lie face down. They then start to tie my arms and legs to the bedpost. With the camera on me again I hear one of them to take his clothes off. I then hear sense you are a virgin I can't help myself and I feel the bed move as he climbs on. I then feel him start to rub his cock along my arse. The one with the camera ask him if he wants any lubrication and he says "no this whore doesn't need it". He then starts to put pressure on my ass and as it slids in they tell me to look at the camera. I'm in so much pain I can't help but let out a scream. He then starts going in and out raping my virgin ass. After awhile it doesn't hurt as much and starts to feel pleasurable as he starts to speed up he starts really pounding my ass. I then can feel him start to cum in my ass. He then gets off of me walks over to where my face is and tells me to clean it. I start to lick the cum off of his cock then he says give me the camera its your turn. Now the other guy takes 
clothes off and starts to fuck my ass. This time it feels better because of the cum that is lubricating my hole. After he comes he gets off and I can feel the third guy get on the bed and he slids his cock in while I clean the second guys cum off his cock. The third guy didn't last that long and I also cleaned his cock off to. 

They all then leave the room with me still tied to the bed. I can know feel the cum draining down to my cock. It is then that I realize I wish the third would have lasted longer because I could have gotten off from getting fucked in the ass.

I was probably laying there for thirty minutes when I heard the door open. I then hear someone taking there clothes off but I cannot see him because he is out sight. He then walks over to where I can see him and for the first time I am turned on by the sight of a man. He was a black man about 6 feet 5 inches very muscular and only wearing briefs only. Encased in those briefs is what looked like a huge cock. He then tells me he knows I am excited because all the white whores want black cock. He the pulls his briefs down, his cock has to be at least 9", and starts to jerk off in front of me. He then starts to shoot his cum all over my face and tells me he did that so he would last longer. He then lowers himself onto the bed and push his cock into my cum soaked ass. He then ask me if I like having his black cock in my ass and I answer yes. He then tells me to beg for his black cock. The next thing I know I am begging for him "to fuck my ass" "harder harder" and moans as he start to bang my ass. As he starts to cum in my ass I can't help myself and cum for the first time with a guy. 

He then brings my clothes into the room and tells me to get dressed. I ask him if I can clean myself up but he says no that I will be going home with there cum in my ass. They then put the bag back on my head and lead me back to van. Next thing I know I am back at my car. I then drive home to meet one of my female friends who tells me she set the whole thing up because she knew I would like it.