Caught Off Guard

I was walking home with some friends when a long old white car passed by very slowly next to us and hinted at me to get close. When I realized he was hinting at me I got close to the car window while my friends just kept on walking.

He was an older gentleman with white hair and fairly built body from just at a glance. He directly told me, "I saw you, I think you look very pretty when you were girl's clothes." I froze. I couldn't breathe, and I felt like my heart stopped breathing. The reason I felt that way is that I occasionally I used to were women clothing at home. He must have been a neighbor that spotted me somehow, I couldn't think of anything else.

I was breathless and it felt like an eternity before he started with his demands. He said "You are going to dress for me and you are going to look pretty when ever I call you. I have your number."

He handed me a plastic bag with what looked like undergarments and shoes. "If you don't comply I will show your friends and family pictures of you all nice and pretty."

I took the bag and said nothing. I didn't even look inside, except for what was visible from the top and I just quickly stuffed it into my backpack. I quickly went home and didn't say a word just went straight to my room. Didn't look into the bag until the next day and found that he had given me thigh high stockings a garden belt a corset and a pair of black pumps. I kind of got excited to imagine me wearing them but my nerves got the best of me and I just stuffed them in the bag and hid it in my closet.

Days passed and one day I didn't even remember all day about the incident when everyone left the house and I was watching T.V. in my bedroom and then the phone rang, I assumed it was some family member then I said, "Hello."

Another voice said. "Start getting ready I will give you 15 minutes and you will hear a knock at the door, if you don't comply I will distribute your pictures."

I just hung up and didn't say a word. I decided to do what he asked. I started shaking. I didn't know what he wanted or what would happen. I quickly got nude and since I had shaved recently I had no trouble putting on the stockings and I already had some panties, I bet he already knew that.

I don't know the reason why till this day but I not only put on what he gave me but I slipped into some nice silk panties, I tucked in my penis and I put on everything he gave me. Surprisingly the high heels fit perfectly and after all that I slipped into a house dress that I used to wear.

That was not enough I actually had time to put on makeup and do my eyes and lips. Till this day I don't know why I wanted to look pretty for this stranger. Maybe I didn't want to be recognized and I think I did a great job. I had long hair and I just brushed it the right way and suddenly...

A knock at the door. My heart sank. I peeked out the window and it was him. I walked quickly towards the front door while I heard the sound of my heels with every step I took, that made my small prick start to move between my legs.

The silk of the panties and stalking felt so good, the trail of the perfume and scent of my lipstick just felt so right and started to ease my nerves, but when I unlocked the door, I couldn't even open it I just quickly turned back to hide in my room,

I heard the door open and when I reached my room I felt him grab me by the hips and suddenly I stopped at the corner of my bed and then I felt a hard dick pressing behind me while his hands explored my legs and ass, my inner thighs and where my dick was tucked. He wedged my panties high into my ass.

He said. "You look prettier than I thought you would my little whore. I am going to make you my bitch tonight and if you scream it better sound like a girl. The more you scream the harder I will fuck you so be warned."

Without another word he held my hips with one hand and with the other strong manly hand he pushed my back towards the bed, I had no option but to put my hands and knees on the bed as I was going to get softly fucked doggy style. Mind you I was a virgin and did not know what was going to happen.

As I crawled on all fours to the bed he grabbed me by one wrist and twisted it back and that only made me go face towards the bed and then I felt his other hand exploring my body and ended up on my ass cheeks. He slapped them pulled the wedge out from my ass, and suddenly I heard him squeezing something, I know now that it was Lub, He was at least nice enough to do that.

He seemed to smear it all over his dick because I had a chance to glance back and see that he not only tripled mine in size but it looked like a monster dick, with veins and huge head and very thick. He certainly was at least 8 inches cut.

I got scared and tried to get out of that position and when I tried he grabbed my hips pushed them down I then tried to turn around but he twisted my arm once again and then with the other one he positioned his penis head directly in my ass hole and I said "Wait Wait don't!!"

He just said "I told you to talk like my bitch" and said that he started to ram his penis deep inside me, I resisted and felt the pain as I had never before felt since I had never had a man before. I screamed in pain into the pillow and suddenly, reason hit me and I knew I was being raped.

I tried to get away but he definitely overpowered me and it just went in the more I struggled. I finally felt his pubes hitting my ass and his big balls slapping my tiny hairless balls and I knew he had made it all the way in. The tight grip on my hips and him holding me down and tugging at my hair, the feeling of his hairy legs rubbing against my girly legs. Knowing he was using me for his bitch , for his pleasure, started making me get all turned on and thats when I started humming in pleasure and screaming like a girl.

Thats when he stopped forcing himself and he laid off me and I positioned myself doggy style and started pumping back, all I wanted was more. I was being torn up inside by this strong older man and I loved being his bitch to make me enjoy dick that way. I thought it would last longer and I wish in retrospect that I would have had the chance at that moment to have stuck his penis inside my mouth but since he was a stranger fucking me in a house where others could come back he was quick about it.

I could see my self from my mirror getting fucked my ass cheeks bouncing off of every push and my heels still on like a good bitch. He grabbed me hard from my hips and started to pump my ass harder, pulling it almost all the way out and thrusting it all the way in, that started to hurt again when all off a sudden he opened my ass cheeks with his hands and thighs and slammed on me one last time and pushed it all the way in and thats when he screamed in pleasure

By this time my small dick was just flapping all over the place with pre cum spurting all over the place. He had just came deep inside me, I started feeling the cum oozing out from my ass when he pulled his dick out and pulled his pants up and left without shutting the door or saying anything. The cum still coming out from my ass and I was still dressed as a hussy little whore with smeared lipstick and all fucked,

I just stroked my penis face down grabbing my balls and all and I started to cum like I had never done before.

I then quickly ran to the door closed it still dresses as a girl that had gotten her brains fucked, ran into the bathroom and sat on the toilet and let the rest of his cum drip out. I felt he had inseminated me. Like I was never the same, from there on I need it. I had been turned into a sissy for ever just like that.

I never saw him nor knew how he knew or whether he really had those pictures of me or not but now I thank him for doing me in the ass that way and making me his fuck bitch that day.