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When I was 19 I used to hang out with a much older boy that I had met from school and he had befriended me. We used to hang out at his house or at my house and play video games, basketball and all sort of natural things kids ply.

One weekend I was told that I was going to stay alone and asked if my older friend could stay with me so that I would not be home alone, I obviously said yes, thrilled by the thought of having my friend stay the weekend.

My friend said yes immediately and I couldn’t wait for the weekend.

When the weekend came, my buddy got to my house with luggage in hand and we were left alone. We started watching TV and after a while my friend told me that it was time for a surprise. He quickly got up and popped in a VHS.

I thought it was going to be a movie of some sort. I was not that wrong. Suddenly I start seeing scenes of Transsexuals, I had never seen. I was a virgin and rarely had seen porn let alone these ladies. He came back to the couch where we were sitting and just started rubbing his crotch over his shorts.

I was impacted by what I was seeing and I asked him what this was and all he said was “just keep watching, don’t you like it?”

So I did, he was my friend and I looked up to this guy. I must say that seeing how these beautiful women with cocks getting fucked and fucking guys got me aroused and that’s when my buddy dropped his pants and I saw for the first time a cock that big and so close to me getting stoked. He could grab his meat with both of his hands and his head could still pop out. It was co thick and veins would pop out like the ones you see in porn films.

I couldn’t keep my eyes off of him but also this incredible porn film that had my tiny cock stiff. I guess it was all part of what he was hoping that the weekend would bring. He went at it for some time and noticed I was not stroking my own cock and asked if I was not hard and I said that I was but was too nervous to do it in front of him especially with his big dick. He smiled and said that it was ok because in this world there is two types of men, the ones who fuck and the ones that get fucked, unless you are a tranny then you could do both. I got confused but he reassured me that we could do a test.

Out from his luggage he was able to pull out a plastic black bag that had a knot in it. He pulled out clothing and threw it to me as he started pulling it out. As he was throwing the clothing I didn’t imagine what it was nor why he was giving it to me and then he finally threw a pair of heels.

These are my sister’s lingerie and clothing and I think that we are going to see what type of man you are. I bet that if you put it on I can get you hard and that will prove that you are a taker or just like a transsexual. My jaw was dropped. Why don’t you go into the restroom and come out when you are ready and don’t forget your heels.

I was paralyzed, I didn’t know if he was playing or testing me or something, he reassured me that this was something he went through and all boys go through. That gave me some reassurance and I grabbed the cloths and went into the restroom.

I first got undressed and now I was so nervous that my cock had gotten limp, I must also mention I at that time had no hair on my body only a bit in my crotch area. I slipped into the panties and then figured out how to put on the stockings which both felt amazing by the way I struggled with the bra and for some reason I stuffed it and then got into the dress and heels which he must have known that we wore the same size. I looked at myself in the mirror and was so impressed on how much of a girl I looked I was so into the whole dressing up that I even put on some lipstick and brushed my long hair as a girl would.

Once I was done I couldn’t believe how nice and sexy I looked. I could pass for a girl easily, but still couldn’t open the door since he was out there. “Are you ready” he asked. I unlocked the door and my heart pounded as I started to open the nob. As I walked out he was to my right under the door way to my room where we were watching the porn movie. He looked and without saying a word he walked towards me and got only an inch away from me that I could feel his body touching mine and his lips where close to mine, he grabbed my waist and told me I looked beautiful.

From then on, he treated me like a girl, grabbing my hands and the back of my neck. “Only one thing is missing. “he said as he lifted my dress and with his hands he reached into his sister’s underwear and told me to open my legs as he tucked my penis in between my legs with his warm hand. No one had ever touched me.

He told me to walk into the room, but that I needed to walk sexy and sit down and cross my legs as a girl would, I did as he asked. Now this experiment should show what type of man you are although I already think you make an excellent girl.

Look at the movie he said, As I did I could feel the nylon on my legs and the skirt raising from time to time and I could feel a bit exposed from my arms and chest area since I was wearing a dress. I could feel the panties riding up my ass, it felt really good for some reason. As I watched the movie and started to get hard again I felt his hand on my thigh, it was warm and it started to rise higher, he would squeeze my thigh just hard enough to show that he really was the man.

All of a sudden he came at me and kissed me and stuck his tongue in my mouth and as I started getting into it he got up and pulled me up onto my heels and took me over to my bed, he got in back of me and I heard as his shorts fell to the floor as he raised my dress. He slapped my ass and that shook my soul and my manhood. He told me to raise one knee on the bed as he grabbed my ass and just said, “let’s see!” he placed his hard rock warm cock in-between my ass cheeks while I had his sister’s G-string ridding up my ass, It felt sooooo good but I was confused and nervous I didn’t know what was really going on or what was about to happen. My tiny cock started feeling hard and wanted release from my thighs but he started pulling on the G-string and he didn’t allow it. He asked me if I liked it and I just nodded yes but didn’t say anything. He grabbed me and turned me to him and my arm hit his cock, it was now hitting my crotch trying to get through the panties. He pushed me down on my knees and demanded to put it in my mouth, It was in front of me, that huge cock and I grabbed it and opened my mouth and did my best to suck it and push it in as the girls in the movies.

He started to moan in pleasure and that made me get hard and finally free from my panties, He said that the last thing to do, I knew what it was. I got his dick out of my mouth and with my heart pounding so hard I crawled to my bed on all four and took of my dress and panties leaving my stockings and bra on. He was ready with Vaseline because I saw it drop next to my face and said that this was going to hurt a little at first but it had to be done. I hardly paid attention since I could only concentrate on his cock on my ass.

He smothered some Vaseline on my asshole and then I felt how his head touched me there followed by him grabbing a hold of my hips so I could not escape what was coming next. He started pushing and wow did it feel strange and it stated to hurt. As I started to scream a bit and move he slapped my ass and said that if I was going to scream it better be like a girl and that he would only push in faster.

He eventually got his head in and that gave me some relief and that’s when he told me I was no longer a boy and that I would never be one anymore since I was tilted over taking a cock. That just got me turned on more and he started to slide it in more, in and out he started to fuck me with that huge cock, it felt so tight and it hurt still so much but I held on tight. After a while it was not so bad and suddenly I felt his pubs on my ass and his balls hitting my ass and that got me so hot to think all of it was in me so at that moment I started pushing back into him.

He would grab my hair and fuck me like a whore for a while and that’s when I felt his hard dick swelling and twitching and he grabbed me even harder and fell on top of me as he came deep inside of me, and exclaimed that I was now his bitch. He would get off and tell me to get cleaned up. I went to the restroom and let his cum slide out.

I felt like a girl, I knew that there was no test needed anymore, I knew it and he did too, all weekend long he made me try different outfits and had me different ways.

That weekend is one of the most life changing memorable moments of my life.

I hope you enjoyed it although maybe not as much as I did.