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First Time, First Fuck, New Porn Star

A story I wrote while on a short break from my Missy series. Don't worry, I just need inspiration.


I am just a normal guy however I have what some would call an abnormal fetish. I am a 23 year old guy and I like to wear and dress up as womanly as possible. I am 5’9, a little chubby but can still pass as a woman, with brown hair, brown eyes and a 5 inch cock.

One night I had gone out with one of my friends and had gone drinking to a few bars. As we went from place to place we started to get more and more people with us until we had a fairly large group. At about 2am, the friend I had originally came to hang out with decided that it was time to call it a night and I went with him. When we got to his place he crawled into his bed and closed the door and I slept on the couch. I didn’t get to sleep very much because I kept on thinking that the roommate could be home any second and would wake me up anyway, however she never came home that night.

8am came around and I was awake and by the look of it my friend wasn’t going to wake up even if a car honked it’s horn inches away from his bedroom window. I sat up and let myself wake up a little and to see if I was sober enough to drive home. As I did, I looked around and found some of her girly stuff. First thing I found was purple glittering nail polish. Being a horny little cd slut, I took off my socks and painted my toe nails then my finger nails without thinking that my toes would be the only thing that would not be noticed. Once they dried I decided to walk around a little and get some water. As I passed the roommates room, I saw she had mountains of clothes piled up in her room. I went in and found that she had literally tons of sexy lingerie and other clothing and even duplicates of the same kind. I looked for a little while and found a set of very sexy clothing.

I took it and went to the bathroom to try it on knowing that there was no way in hell that I was going to be caught anyway and the roommate was a fairly big girl and her clothes would fit me easily. When I got to the bathroom I locked the door and looked at what I had collected. I had found a black thong with some glitter on it with a matching bra and garter belt. I had also taken a pair of black nylon stockings with lace on the top that went up to my thighs. I removed all my clothes and first put on the bra and garter belt followed by the stockings. By then I was hard and looked very sexy as I was, however I had to finish the outfit with the thong and slipped it overtop of the garter belt like I had seen in some porn movies. As it slipped perfectly between my cheeks, the fabric felt electric as it rubbed against my now winking hole and precum oozing cock.

I looked myself up and down in the mirror then decided that since she had at least 3 other complete sets exactly the same as what I was wearing; I was going to keep it and wear it home under my normal clothes. I quickly put on my normal clothes with the exception of my boxers. I had to leave them off because with the garter belt it was too much to have under my jeans therefore I left them off and just threw them in my car when I got outside. As I got in my car it was still fairly early and remembered hearing about a new porn store that had opened in the city and decided to go check it out.

While driving down the roads and streets, I could feel the thong doing its job and clenching tightly inside the crack of my sexy bum. I couldn’t help but think to myself of how much of a slut I was to dress like I was and go to a porn store to look at dvds and dildos.

When I got there, I parked right in front of the door which didn’t matter since there were other places beside the adult store and no one would be able to tell which vehicles went to where anyway. I got out and felt my jeans falling down and revealing my thong and my shirt starting to stick to my body. I was afraid of being discovered but I really wanted to see what was there and buy something I could have fun with later.

I walked into the porn store to find that it was more then just things for sex, it also had a lot of drug related objects such as pipes and insense like what you would see in a cheech and chong movie. I looked at the register to find a man sitting there, he was tall with glasses and dark hair and a slim build and he welcomed me in and asked if I was looking for anything in particular. I told him no and I was just looking around and he went about his business and went into the back room leaving me alone in his store. I went straight to the porn part of the store and began with the inflatable sex dolls and kept going. At one point I saw a fist sex toy that made my face blush as I thought about a man’s hand being completely inside my ass. However, I continued looking because I knew I may not have a lot of time to look at the dildos before the man came back.

The sight of so many sexy toys drove me crazy and I even forgot that I was wearing lingerie or maybe even it was the lingerie that made me this crazy horny for dildos, either way I wanted a closer look. Then I looked down at the bottom row and saw a particular dildo that had caught my eye. I looked around to see if the man had come back yet and did not see him so I decided to take a closer look. I got down as low as I could while I bent at both my waist and my knees so it was like I was in the fetal position but still standing and be able to get up fast if he suddenly came back.

The dildo I saw was white, with a tapered head and about 7 inches long with a nice pair of balls and a suction cup base. It looked so erotic that I needed to pick it up and get a better look. I picked it up with both hands and held it up as I felt along the shaft with my fingers then flipped it over to read everything on the back. However as I was reading I didn’t notice that the man had come back and was now checking me out. He gave a whistle and looked at me with a smile on his face. I dropped the dildo and jumped up on my feet as my face blushed bright red but it was too late. The man approached me then bent down to pick up the dildo. He handed it to me and told me a lot of people actually come in and buy that particular product but never a girl as pretty as me. I lowered my head and smiled and he placed the dildo back on the shelf before he got really close to me and started rubbing his hands all over my body.

It was a strange new feeling but felt good whenever he got close to my ass, but before I could melt he pushed me away then walked to the door and locked it before turning back to me.

“Show me please, and I promise you will not regret it.” He said to me.

At first I wasn’t sure as of what to do but being as horny as I was I could not resist such a prime opportunity. I took off my t-shirt revealing my bra and his eyebrows raised but he kept his smile. Next were my jeans as they dropped revealing the rest of me and lastly the socks and shoes which concealed the stockings part of my feet. Then the man looked me up and down and said that I looked very sexy and told me I was good enough to fuck. I told him thank you and smiled. The eroticism must have given me a high because I put one hand on my hip and another on my butt as I started to strut back and forth like a model or a stripper for victoria’s secret.

I turned to face away from him and got down as low as I did before but this time I spread my legs wide and swayed my ass back and forth a little as I looked back at him. Then I looked ahead again as I fell forward on my hands and knees and arched my back showing to him the best part of any woman wearing a thong which I think he really liked. He gave me a few hoots and whistles but then came up behind me and dry humped me a little and caressed my ass. I decided to play along and moaned a little but fairly loudly like he was fucking me deep and hard. He gave my ass a couple little smacks but then stopped and got me up on my feet.

“We have more in the back if you are interested in seeing.” He said with a playful grin as he took me by my hand and led me to the back room where he was previously.

When we got to the back room I got a quick look at everything that was around including some of the dildos they had on display with condoms by each one as if they were set there for test drives before people bought them. I did not get to look long as he opened a door and pushed me inside and told me to wait for a second. I did as I was told and it wasn’t long before a see through dildo with a pee hole opening on the tip came through one of the holes in the wall. I knew exactly what to do as I started sucking on the dildo and lapping up and down the shaft and swirling my head around it like a good little slut. At one point I even got onto my knees and stuck out my ass as I took the dildo as deep as I could down my throat but I gagged and my mouth, chest and the dildo were covered in saliva.

Then suddenly without warning I saw a quick color change from inside the dildo and pulled my mouth off just in time to get a face full of fake cum blanketing me and filling my mouth with its white cream.

“Oh my god! That was so amazing I did not expect something like that to happen.” I said in a loud but happy tone.

Suddenly the door flung open and there was the man with a camera filming me covered in the fake cum. At first I was shocked but was still on my horny high and started to crawl on my hands and knees towards him. He backed up and then I continued to crawl towards a curtain then I stood up in front of it and bent over, showing him my ass. When he got close, I swayed slowly back and forth and grinded against his growing cock. The man got in close for a very good shot of my ass then stood up right behind me again before thrusting hard against me, making me fall through the curtain to what I now discovered was another room. I looked up to find a bed with cameras getting different angles of it.

“How would you like to become a real woman right here in front of all these cameras?” He asked me with a hopeful look in his eye.

Not being one to disappoint, I hopped on the bed and spread my ass wide and started giving a good booty shake show just for my cock in waiting.

“What do you think big sexy man?” I giggled and moaned.

He turned on the cameras then hopped on the bed right behind me. He gave my ass a few hard slaps before pulling down my panties to around my thighs. Then he started to pour lube all over my ass until it shined in a sleek glow. He took out his cock and pressed it against my hole. At first I was surprised and having second thoughts but before I could think for too long he pushed his cock right into my ass. The slippery feeling took over my body as I could feel it twitch in every part of my body.

He started to thrust, hard but slowly until he got a good rhythm going. He fucked me on my knees and on the bed for only about 5 minutes before he flipped me over onto my back then plowed back into me but this time faster. The sloppy wet slapping noise he was making as he fucked me was so amazing I couldn’t help but start to moan.

Louder and louder my moans become until I’m screaming in pleasure from his cock hitting my P spot over and over again. My toes started to curl and I threw my head back against the head board as his cock plunged into my little hole over and over again, popping my black cherry for good.

I still had the fake cum on my face and chest so I let go of the man taking my anal virginity and started rubbing it all over me. I pulled down the shoulder straps of the bra I was wearing and rubbed the fake cum into my mouth then down to my small tits as I started to rub my nipples until they were hard. During this time, the man kept pounding my man pussy harder and harder and when my nipples were hard, I pinched them hard making them solid and sensitive.

When the man saw this he grabbed my wrists then used hand cuffs on me then braced them to the head board, making me helpless to what was coming next. He grabbed my nipples hard and started to roll them between his fingers while grinding his cock inside me. Then the man pulled his cock out and went out of the room for a second leaving me horny and begging for more. I squirmed and tried to get loose as I felt my clothing just hang off my body.

Eventually he came back but with some sex toys to add to the fun. He took off my panties and stuffed them in my mouth till it was all past my teeth. Then he put in a ball gag in my mouth to keep me from spitting them out. I could taste all my juices from my ass and cock on the panties as I couldn’t even make a moan with them in my mouth. Then he grabbed nipple clamps and put them tightly on each of my nipples. At the first moment that they were on it was a shooting pain and I wanted to just pull them off as quick as I could. That soon faded as now I was becoming very aroused by it and I was finally able to muster a moan.

My body began to shake and squirm as I felt the man watch me. Without notice he plunged his cock right back into me balls deep. He continued to fuck me for what seemed like an hour, changing positions and fucking me like a wild animal. It wasn’t long before our urge to cum had finally arrive. He gave a few last thrusts before squirting a huge load into my ass, filling me like a flood of hot goo to my stomach. At the same time I had my overwhelming orgasm as well, it shot straight up into the air and landed all over my body making me all sticky and smell very strong of cum.

The man pulled out of my ass and released my hands from the cuffs. I kept the nipple clamps on as well as the gag as he walked over to the cameras to shut them off one by one. Once he was done I got up to fix my clothing and take off the gag so I could put my panties back on but he stopped me.

“I have a deal for you. If you let me sell your video in my store, you may have 80% off everything in here and you can go home with the nipple clamps and the gag for free.” He said to me with a happy look on his face.

I took off the gag and removed my panties from my mouth so I could talk.

“Sure.” I said with a smile then removed the nipple clamps as well so I could put all my clothes back on.

I left the store soon after with my rewards for my “mornings work” and drove home. The entire way my nipples were aching and I couldn’t help but play with them a little since they were so sensitive until I got home.

It was a few weeks later when I got and e-mail. I opened it to find it was from the man at the porn shop. He wrote that there has been quite a lot of good responses to my video and customers couldn’t wait for more and some have even asked about more kinky videos with the same person.

I smiled and replied to his e-mail saying simply:

“Give me the time and place big boy.”

The end.

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