I was a normal 16 year old. I had a pretty feminine body and personality, i had a nice round ass. I could have been the perfect sissy boy if i dressed up. I was straight up till a life changing thing. My family was filthy rich and we also had our security team. I had a personal guard with me, his name was Tim. Tim was a 35 year old buff guy with a hairy body and a moustache. Tim and I were best friends, i had known him for 5 years now, i spent most of my days living alone, my family bought me a penthouse apartment and i lived with my guard and a personal cook.
I had an average cock. I didnt jerk off because up till now i still had not discovered it. Everything changed one day. Now Tim and I spent alot of time together since he was like my best friend although he was much older than me. He was a great person and quite loving. We were one day hanging out in my room, we were alone at home. I had just returned from my tution class. I was laying on my bed, in my underwear and Tim was sitting next to me. He suddenly said "You wanna see something cool?" I said yes. He made me promise i couldnt tell anyone about it and after i agreed he got on the bed and spread his legs. He then asked me to close my eyes, i did and when i opened my eyes i saw his huge cock standing straight up. My eyes were locked on to his huge 9 inch cock. I stared at his hard cock for minutes. When i got into my senses i turned my face and he asked me not to be shy. He got up and came close to me and pulled my underwear down exposing my cock. I was shocked to see i was hard too. I was going to stop him but suddenly he grabbed my cock and started sucking it.
His mouth felt so good, i couldnt move at all. A few minutes later i felt like i was going to shoot and i did. He ended up swallowing every bit of it. I fell down on the bed, i never felt this much pleasure. The only time i ejaculated was during wet dreams about a girl i liked. I laid on the bed, Tim got up and got completely naked. It was the first time i saw his body. He came close to my face and said "Did you enjoy that?" I nodded. He smiled and got on the bed. He spread my legs and lifted them. He buried his face in my ass and started licking my hole. It felt so good, he was shoving his tongue inside my hole. He must have rimmed me for 10 mins then he spit on my hole and rubbed it with his finger. He then slowly inserted his finger, i jumped in pain but he asked me to calm down. Slowly he was able to insert his finger completely inside, then he started moving it. This whole feeling was so good. After some time i was hard again, and enjoying it all. Tim entered another finger then another. In no time i was being fingered by three of his fingers. His cock was big but not thick, you could say it was about the same thickness of three fingers.
Once my hole was loose enough he pulled his fingers out. He spit on my hole again and also on his cock. He placed his cock on my hole and slowly pushed it, the tip was big and it hurt but i managed to bear the pain. After he inserted half his cock i asked him to stop it was too big for me. He started fucking me with half his cock and after some time i was enjoying it, the pain was decreasing. After some pounding he started pushing further with every thrust, and i was in so much pleasure that i didnt realize he was now balls deep inside me. He then turned me around and said "The real fun starts now" He then started pounding me and gradually speeding up. I got fucked for 20 mins, i was hard and leaking cum too. I soon felt his warm cum in my hole, and that feeling was enough to make me shoot my cum on the bed. He fell on top of me, his cock was still inside. After some time, he got off and laid next to me, the pleasure was gone now and i was started to feel my hole in pain. I stayed there frozen and eventually fell asleep due to tiredness.
I woke up hours later, Tim was behind me and fucking my ass. He grabbed my face and kissed me. He moved his hands to my nipples and pinched them. My ass was red from spanking. Tim and i had sex for hours, i was completely drained. My ass was filled with cum, Tim even made me swallow his last load. After that day, i was fucked every night by Tim. I enjoyed it alot, i never thought i was gay. I was in love with Tim and i had accepted him as my lover.
Everything was going good, i thought Tim was my only one and that we would have a long lasting relationship. I was wrong, i was nothing more than a hole for Tim and he proved it. One night he came to my room, i ran to him and kissed him. I thought we were going to have sex. He had other things planned. He gave me a bag and asked me to wear the clothes inside. I looked inside and there were all female clothes. I joked that he bought the wrong clothes and laughed. He slapped me across my face. The slap was so hard that i ended up crying. He kicked me and asked me to get up and wear the clothes. I was sobbing and stripped down. I wore a bra and panties, then i wore a shirt and a short skirt. He even brought knee high socks, i even wore them. He made me stand and took a picture. He said "You look good". He asked me to wait for him.
After an hour he came back but he was not alone. He had 4 guys with him. I was scared and embarrassed. One guy said "So this is the famous rich brat you always talked about?" I asked Tim who were they. Tim grabbed my chin and said "These are my friends and they will use you with me". I felt a shiver down my body. Tim started kissing me and after 5 mins i felt other hands on my legs and chest. I broke the kiss to see all of his friends were naked and they all had huge cocks. This one guy had the smallest but the thickest cock. Tim made me get on my knees and asked me to suck their cocks. I nodded no and he slapped me. Then one guy grabbed my hair and shoved his cock in my mouth. I was gagging on his hole and i also puked a bit. Tim was holding his phone and recording me. I realized i had no other choice but to comply. I sucked them one by one. That one guy with the thickest cock was the only one i couldnt suck, it just wasnt fitting in my tiny mouth. This definitely pissed him off because he picked me up and threw me on the bed. He grabbed my panties and tore them off. He turned me around and placed his cock on my hole. I was scared that it would hurt. He soon pushed his tip inside and gave the biggest scream i could. Another guy came and shoved his cock in my mouth. He kept shoving his cock down my hole and was soon all the way inside. My hole was in so much pain, i felt his cock tear up my insides. After that he mercilessly fucked me for 20 mins, he soon pulled his cock out and another took his place. They kept switching places, i laid on my stomach helpless in extreme pain. I was fucked for hours, after some time even Tim joined in. All of his friends were done, each made me swallow their cum. It was only Tim left, he fucked me for another 30 mins and then came in my mouth. I swallowed his cum and then they all left. I stayed there frozen, i was unable to move, my whole body was in pain.
The next day i woke up and barely walked to the shower. I cleaned myself, and went to my room. Tim was already waiting for me, he told me to dress up and that other people will be coming over. I begged him not to let this happen, he laughed and asked me to lick his boot. I went over and licked his boot clean, he unzipped his pants and shoved his flaccid cock in my mouth. He fucked my mouth until he was hard, then he started fucking me. He fucked me until he was about to cum, he shoved his cock back in my mouth and sprayed his cum over my face. He rubbed all the cum on my face with his cock. After that i licked his cock clean.
Later 3 men came and fucked me. After that 6 more came at night and fucked me all night. Over the next few months i was fucked by countless men, i was tied up, fisted and pissed on. I was fucked senseless by monster cocks. I was also subjected to BDSM. Tim pimped me out to alot of guys, each of my sessions were recorded. After getting fucked so much, i pretty much became a nympho. I enjoyed getting dominated by men and fucked senseless. I accepted this as my life.
