Tough Decisions
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A Tough Decision free porn video
My name is Claire born mike. I’m writing my story while I can I don’t know how much longer I have. If you are squeamish you may want to stop reading now. This is the story of my life. It’s dark, brutal and disgusting at times. I’m 43 now but it all started when I was in my late teens.
I was born a boy, but never felt like I should have been. In my teens my friends were all dating girls, but I wanted to be the girls, not date them. In my early years I would wear my sisters clothes that’s how it all started. Then I started shoving stuff in my ass, from there I found myself in public bathrooms sucking strangers cocks. I loved the feeling of the powerful muscle in my mouth, I loved when they came, the sperm splashing against my tonsils. The unique taste, the smell I loved cock and cum. There was one older man who I sucked daily he would give me twenty dollars each session. His cum was thick and bitter. He was my favorite. One day I found myself holding onto the rim of the toilet, the stranger behind me fucking my ass raw, his big cock pounding away, his balls slapping mine. I was in heaven. My cock flopping around slapping my stomach with each thrust. Cum dripping from it. He was my first of many things, my first suck my first fuck and the first person to shoot his cum in me. The entire feeling was excellent. He paid me $75 each time. From there I would suck and be fucked multiple times a day. I was making lots of cash. I used the cash to transform myself into Claire. Buying clothes, taking estrogen pills. Anything to present myself as a female. I only stood 5’6” I was thin but had a great ass, my cock soft was about 2” hard 6.5. When being fuck or sucking I was always rock hard. But I wanted to be soft. I didn’t want the strangers to get turned off by it. Although some liked holding it and jerking it. I was never really interested in that. I started tucking it up inside me and covering it with tape before going out. If it was to try and get hard it would be painful. I really enjoyed the pain. Some guys would get rough with me, usually after they came. They would slap me around and call me a faggot. I liked it I loved the pain.
My parents caught me dressing one day and kicked me out. I had enough money to get a motel room and started working out of there. Men would come and fuck me and leave $75 a pop. I lived there for free cause the owner was a client. I spent 2 years getting fucked in that bed. I saved every penny I could. Finally able to go on hormones. My body changed pretty quickly, I had small A cup tits, my hair was thick and long, my hips and thighs wider and my face more feminine. My cock didn’t get so hard so often and I loved that. I’ve never used my dick so I was a virgin in that time. On the street I looked like a girl.
In my twenties I continued to be a whore. I loved the money and attention, the cock and the cum. I met another prostitute named Destiny. She was female and stayed in the same motel, a beautiful woman. She took me under her wing and taught me how to be a better hooker. Up until this time all my clients were using me raw and squirting in me. She changed that and my prices. We ended up working together and were basically in a relationship. We lived, slept together. She was the first pussy I ever ate or fucked. I wasn’t really interested in fucking her but I loved her so I did when I could get hard. We were together for 4 years until one day she went on a outcall and never returned. I was devastated. A wreck. But my holes still provided a service. I remember laying on my stomach crying for my lost girlfriend while a big black cock was pounding me thick ass. I wasn’t even there with him. Just zoned out. For weeks it was the same. Just a zombie being used.
I had to move there was too many memories of my lost love. I headed to California. I got a place and set up shop. Word of mouth caught on and I raised my prices. One Saturday there was a paying customer at my door every 45 minutes. From 6am to midnight. My mouth and ass was so sore. One guy would pound me when he was walking out another coming in. I never got off the bed, my hole still gaped from the last guy. I took a lot of cock that day from 4” - 11”. Swallowed so much cum I wasn’t hungry. Saturday’s were my best days. Always a steady flow of cash and cock. During the week mornings were best. I would wake up at 4am for my first clients. Blue collar men who wanted to cum before work. Some lunch dates and some evenings. It wasn’t long before I got my DD tits. Dyed my hair blonde, got some lip filler. I was a total tranny bimbo slut. Men loved fucking me. I also had lots of me want to date me. But I just wanted to earn.
By the time I was 30 I had a very large bank account. Been fucked thousands of times. And remained diseased free. On my 30th birthday I wanted it to be special. I had a few clients interested in a gangbang no condoms. After they were all tested I set it up. 4 big dick men, gorgeous men. Came to my room and had their way with me for 6 hours. I told them to make it nasty. They choked me spit on me slapping and spanking. I remember one guy Buck pulled me in the tub they stood around pissing in my face in my mouth all over me it was so warm it was my first golden shower. I ended up swallowing some of the piss. Rubbing it all in my body I loved it. It was also the first time for double anal. It hurt so good. We tried for 3 but the large stature of the men the 3rd barely got in. They used and abused me for 6 straight hours and I never felt so sexy. Buck ended up staying the night at my request. He was always a gentleman and I wanted to feel a man the entire night. I remember vividly he was on his back smiling as my ass rode his huge cock, my soft cock slapping his stomach. He held my hips my tits bouncing he felt perfect inside me. The only client I ever kissed. He made me feel complete. I came all over him from his cock hitting my prostate. He scooped it in his fingers and ate my seed. I was never so turned on. He came inside me and I laid on his chest holding his cock inside. After a bit I rolled to my side, his hand grabbed my soft cock and started jerking me. Usually I would stop that but I didn’t mind with him. We made out while he jerked my hard cock, he started kissing and licking down my body. His warm mouth encapsulated my hard dick. He sucked my cock. I grabbed his head controlling his movement. Arching my back and moaning as he sucked me. It wasn’t long and I came in his mouth. It was amazingly beautiful. We fell asleep together. In the morning I woke up to get ready for clients, we showered together and he asked me for a favor. For the first time in my life I found myself with my cock inside a man. I wanted to make him happy, I really liked him, so I did what he wanted. It didn’t take long before I came. He loved it.
I returned to business as usual. But I found myself talking to Buck every day. He would come over after hours to spend the night. He was not a client anymore but a lover. Fucking him in the shower every morning was great cause my cock would stay limp throughout the day. He really loved pissing on me . That was his fetish and to be honest I loved it, the smell and the taste.
Buck ended up wanting more than I was willing. He wanted me all for himself and I refused one night he came in drunk and enraged he ended up beating the hell out of me. The cops were called and he went to jail. A few days later I ended up in the hospital. Apparently flushing my ass clean every morning for the last 15 years wasn’t a good idea. Something about removing the good bacteria. I was hospitalized for a week. At a crossroads my ass made me money but nobody wants a dirty dick. I could get fucked by average cocks no worries but the 11-12” cock went deep and let’s face it I loved the long thick better. I took off a month to recoup and think of my plan.
One day I was in my room watching tv when a knock at my door. A older good looking well dressed gentleman was standing there with a bag. He was a doctor from the hospital checking in on me. He had a offer for me. He wanted me to himself, a live in paid sexual entertainment type. The salary was $75,000 a year. He wanted me to be his shemale lover. He lived in Beverly Hills. He told me he would take care of me so I wouldn’t get sick ever again. I agreed to live with him so I moved in leaving everything I knew behind. The first night there we sat on the couch just talking. He was so nice. Weeks went by and he never touched me. Finally one day he pulls out his cock, it was the biggest cock I ever seen. 13” and really thick, big veins big balls I was amazed and terrified. He laughed this is why I need you most women are terrified of it.
I dropped to my knees and the corners of my mouth felt like they were ripping as I sucked him. He came so much I was gagging trying to swallow it all. He says I’ll only use you every three days or so for two reasons. One for you to recoup and two so my semen builds back up.
I’m used to getting fucked multiple times a day everyday but he was paying me so I was game. 3 days later I woke up in the morning he was holding me tightly sleeping his hand on my bare tit his hard cock pressed against my asshole. Mmmmm I moaned pushing my ass back on his cock. He whispered good morning baby. Good morning sir I moaned.
Please not sir call me daddy
Yes daddy I moaned. In all honesty he was old enough to be my dad. Nicer than my dad. He was now my daddy.
He reached in the side drawer pulling out lube and coating my tight hole. Oh daddy I have to enema !
Baby that’s what makes you sick.
But it’s morning and your huge it’s definitely going to get messy.
I feel him pushing harder I lift my leg and relax. His cock spreads me open and his shaft pushes deep. He so huge my eyes tear. Halfway in and meets resistance. Slowly he fucks my ass. Fuck me daddy I beg. He does just that. Rolling my back to his chest his hands gripping my tits I spread my legs wide and he jackhammers my ass. My cock cums on my belly. My ass never feeling so full. Daddy biting and sucking my neck, he pushed my body down and drives balls deep inside me. As he fucks me there is a distinct smell in the air. It didn’t bother him. He just kept fucking. Rolling me over to my stomach he pounded away. I knew it I could feel the clamming of it, the smell. He continued to slam his chocolate covered cock in and out until he exploded inside me. His seed gives me a enema and I have to rush to the bathroom daddy comes in and starts the shower. His cock still hard and stained. We get in the shower and his cock pushes back in. I hold the bar on the wall. That’s my good little girl he moans. Where his stamina came from I have no idea but he drove his massive cock in and out of my ass like a porn star. My cock dripping the entire time. It wasn’t just the pounding but it was the passion. I’ve never felt so good. I was definitely cleaned out now as his cock pushed the warm clean water in and out. We showered until the hot water ran out. He never came. We returned to the bed pulling the sheets off. I rode him for 2 hours. He never came. We spent the day with his cock inside me. Hours of endless fucking. I had multiple full body orgasms. He was amazing. He told me he had a rare condition after he cums once he just can’t again but can stay hard for hours. I ended up exhausted and very satisfied. Every 3 days went the same way. He fucked the shit out of me literally, go to the shower then the bed. We destroyed lots of sheets. He was great at passionately making love to me. It always started rough and nasty but ended up being beautiful. Me and daddy fell in love quickly. It was my perfect life. Was...
The love lasted 4 years. One day my daddy changed. Something snapped inside his mind he went from loving dad to brutal slave owner. It wasn’t gradual it was instant. We were drinking one night and I had too much to drink I blacked out. I woke up the next morning naked and afraid. I was locked in a iron cage. It was 8’ long 5’ wide and only 5’ tall. I couldn’t fully stand up . In the corner was a large tub full of cat litter. There was a sink faucet I could drink from and some of the dirty ruined sheets and blankets covered the floor. It smelled of musk. I was humiliated as I hovered over the litter pan going to the bathroom. No toilet paper no wipes I had to use the sheets. I spent the day wondering what happened. I had no idea what time it was, there was no windows in the dungeon. In the far corner from the cage was a wall less shower. A toilet. Torture devices every where . Shackles on the walls. It was a dungeon.
I heard the door open. Daddy stood the smiling. Asking how I was.
What the fuck is going on I asked.
Two options he said as he unlocked the cage. He led me to the center of the room shackles my ankles to the floor my wrists to the ceiling. My body trembling in fear. Daddy grabbed a whip from the wall. The whip flew at me wrapping around my waist stinging my tummy. I cried out from the pain. Over and over he whipped me. My back, ass and stomach covered in deep red marks. After he was satisfied he pulled his cock out spits on it and rams it in my ass hard. No lube I was in tears. He loved it. He fucked me hard and long standing. I was in terrible pain but my cock dripped excessively . He fucked me for hours without orgasm. He pulled my hair pinched my nipples, spanking my entire body hard including my face. It was brutal and terrible but still I had full body orgasms over and over. My mind hated it but my body craved it. I never been in so much pain in my life. After he finally came he unshackled my wrist and I dropped to the floor. He presented his stained cock. Suck it!
It wasn’t covered like before but it was disgusting and I would do anything to stop the torture. The beating and fucking lasted forever. When he was finally finished he sat down next to me. Do you still love daddy he asked
Yes daddy I still love you I cried
Good girl so you have 2 options.
1. This is your life now living in a cage with only a litter pan and daily torture.
2. Volunteer to be my first surgery to change your gender permanently. Removing your testicles and cock making you a pussy. You will be my lover for the rest of our lives upstairs and this dungeon will be dismantled.
You have till tomorrow to decide. Here’s a journal for you to write in. Now I sit here writing hoping if I’m no longer someone will find this. I have to decide now. He’s not a surgeon .
What should I do?
I was born a boy, but never felt like I should have been. In my teens my friends were all dating girls, but I wanted to be the girls, not date them. In my early years I would wear my sisters clothes that’s how it all started. Then I started shoving stuff in my ass, from there I found myself in public bathrooms sucking strangers cocks. I loved the feeling of the powerful muscle in my mouth, I loved when they came, the sperm splashing against my tonsils. The unique taste, the smell I loved cock and cum. There was one older man who I sucked daily he would give me twenty dollars each session. His cum was thick and bitter. He was my favorite. One day I found myself holding onto the rim of the toilet, the stranger behind me fucking my ass raw, his big cock pounding away, his balls slapping mine. I was in heaven. My cock flopping around slapping my stomach with each thrust. Cum dripping from it. He was my first of many things, my first suck my first fuck and the first person to shoot his cum in me. The entire feeling was excellent. He paid me $75 each time. From there I would suck and be fucked multiple times a day. I was making lots of cash. I used the cash to transform myself into Claire. Buying clothes, taking estrogen pills. Anything to present myself as a female. I only stood 5’6” I was thin but had a great ass, my cock soft was about 2” hard 6.5. When being fuck or sucking I was always rock hard. But I wanted to be soft. I didn’t want the strangers to get turned off by it. Although some liked holding it and jerking it. I was never really interested in that. I started tucking it up inside me and covering it with tape before going out. If it was to try and get hard it would be painful. I really enjoyed the pain. Some guys would get rough with me, usually after they came. They would slap me around and call me a faggot. I liked it I loved the pain.
My parents caught me dressing one day and kicked me out. I had enough money to get a motel room and started working out of there. Men would come and fuck me and leave $75 a pop. I lived there for free cause the owner was a client. I spent 2 years getting fucked in that bed. I saved every penny I could. Finally able to go on hormones. My body changed pretty quickly, I had small A cup tits, my hair was thick and long, my hips and thighs wider and my face more feminine. My cock didn’t get so hard so often and I loved that. I’ve never used my dick so I was a virgin in that time. On the street I looked like a girl.
In my twenties I continued to be a whore. I loved the money and attention, the cock and the cum. I met another prostitute named Destiny. She was female and stayed in the same motel, a beautiful woman. She took me under her wing and taught me how to be a better hooker. Up until this time all my clients were using me raw and squirting in me. She changed that and my prices. We ended up working together and were basically in a relationship. We lived, slept together. She was the first pussy I ever ate or fucked. I wasn’t really interested in fucking her but I loved her so I did when I could get hard. We were together for 4 years until one day she went on a outcall and never returned. I was devastated. A wreck. But my holes still provided a service. I remember laying on my stomach crying for my lost girlfriend while a big black cock was pounding me thick ass. I wasn’t even there with him. Just zoned out. For weeks it was the same. Just a zombie being used.
I had to move there was too many memories of my lost love. I headed to California. I got a place and set up shop. Word of mouth caught on and I raised my prices. One Saturday there was a paying customer at my door every 45 minutes. From 6am to midnight. My mouth and ass was so sore. One guy would pound me when he was walking out another coming in. I never got off the bed, my hole still gaped from the last guy. I took a lot of cock that day from 4” - 11”. Swallowed so much cum I wasn’t hungry. Saturday’s were my best days. Always a steady flow of cash and cock. During the week mornings were best. I would wake up at 4am for my first clients. Blue collar men who wanted to cum before work. Some lunch dates and some evenings. It wasn’t long before I got my DD tits. Dyed my hair blonde, got some lip filler. I was a total tranny bimbo slut. Men loved fucking me. I also had lots of me want to date me. But I just wanted to earn.
By the time I was 30 I had a very large bank account. Been fucked thousands of times. And remained diseased free. On my 30th birthday I wanted it to be special. I had a few clients interested in a gangbang no condoms. After they were all tested I set it up. 4 big dick men, gorgeous men. Came to my room and had their way with me for 6 hours. I told them to make it nasty. They choked me spit on me slapping and spanking. I remember one guy Buck pulled me in the tub they stood around pissing in my face in my mouth all over me it was so warm it was my first golden shower. I ended up swallowing some of the piss. Rubbing it all in my body I loved it. It was also the first time for double anal. It hurt so good. We tried for 3 but the large stature of the men the 3rd barely got in. They used and abused me for 6 straight hours and I never felt so sexy. Buck ended up staying the night at my request. He was always a gentleman and I wanted to feel a man the entire night. I remember vividly he was on his back smiling as my ass rode his huge cock, my soft cock slapping his stomach. He held my hips my tits bouncing he felt perfect inside me. The only client I ever kissed. He made me feel complete. I came all over him from his cock hitting my prostate. He scooped it in his fingers and ate my seed. I was never so turned on. He came inside me and I laid on his chest holding his cock inside. After a bit I rolled to my side, his hand grabbed my soft cock and started jerking me. Usually I would stop that but I didn’t mind with him. We made out while he jerked my hard cock, he started kissing and licking down my body. His warm mouth encapsulated my hard dick. He sucked my cock. I grabbed his head controlling his movement. Arching my back and moaning as he sucked me. It wasn’t long and I came in his mouth. It was amazingly beautiful. We fell asleep together. In the morning I woke up to get ready for clients, we showered together and he asked me for a favor. For the first time in my life I found myself with my cock inside a man. I wanted to make him happy, I really liked him, so I did what he wanted. It didn’t take long before I came. He loved it.
I returned to business as usual. But I found myself talking to Buck every day. He would come over after hours to spend the night. He was not a client anymore but a lover. Fucking him in the shower every morning was great cause my cock would stay limp throughout the day. He really loved pissing on me . That was his fetish and to be honest I loved it, the smell and the taste.
Buck ended up wanting more than I was willing. He wanted me all for himself and I refused one night he came in drunk and enraged he ended up beating the hell out of me. The cops were called and he went to jail. A few days later I ended up in the hospital. Apparently flushing my ass clean every morning for the last 15 years wasn’t a good idea. Something about removing the good bacteria. I was hospitalized for a week. At a crossroads my ass made me money but nobody wants a dirty dick. I could get fucked by average cocks no worries but the 11-12” cock went deep and let’s face it I loved the long thick better. I took off a month to recoup and think of my plan.
One day I was in my room watching tv when a knock at my door. A older good looking well dressed gentleman was standing there with a bag. He was a doctor from the hospital checking in on me. He had a offer for me. He wanted me to himself, a live in paid sexual entertainment type. The salary was $75,000 a year. He wanted me to be his shemale lover. He lived in Beverly Hills. He told me he would take care of me so I wouldn’t get sick ever again. I agreed to live with him so I moved in leaving everything I knew behind. The first night there we sat on the couch just talking. He was so nice. Weeks went by and he never touched me. Finally one day he pulls out his cock, it was the biggest cock I ever seen. 13” and really thick, big veins big balls I was amazed and terrified. He laughed this is why I need you most women are terrified of it.
I dropped to my knees and the corners of my mouth felt like they were ripping as I sucked him. He came so much I was gagging trying to swallow it all. He says I’ll only use you every three days or so for two reasons. One for you to recoup and two so my semen builds back up.
I’m used to getting fucked multiple times a day everyday but he was paying me so I was game. 3 days later I woke up in the morning he was holding me tightly sleeping his hand on my bare tit his hard cock pressed against my asshole. Mmmmm I moaned pushing my ass back on his cock. He whispered good morning baby. Good morning sir I moaned.
Please not sir call me daddy
Yes daddy I moaned. In all honesty he was old enough to be my dad. Nicer than my dad. He was now my daddy.
He reached in the side drawer pulling out lube and coating my tight hole. Oh daddy I have to enema !
Baby that’s what makes you sick.
But it’s morning and your huge it’s definitely going to get messy.
I feel him pushing harder I lift my leg and relax. His cock spreads me open and his shaft pushes deep. He so huge my eyes tear. Halfway in and meets resistance. Slowly he fucks my ass. Fuck me daddy I beg. He does just that. Rolling my back to his chest his hands gripping my tits I spread my legs wide and he jackhammers my ass. My cock cums on my belly. My ass never feeling so full. Daddy biting and sucking my neck, he pushed my body down and drives balls deep inside me. As he fucks me there is a distinct smell in the air. It didn’t bother him. He just kept fucking. Rolling me over to my stomach he pounded away. I knew it I could feel the clamming of it, the smell. He continued to slam his chocolate covered cock in and out until he exploded inside me. His seed gives me a enema and I have to rush to the bathroom daddy comes in and starts the shower. His cock still hard and stained. We get in the shower and his cock pushes back in. I hold the bar on the wall. That’s my good little girl he moans. Where his stamina came from I have no idea but he drove his massive cock in and out of my ass like a porn star. My cock dripping the entire time. It wasn’t just the pounding but it was the passion. I’ve never felt so good. I was definitely cleaned out now as his cock pushed the warm clean water in and out. We showered until the hot water ran out. He never came. We returned to the bed pulling the sheets off. I rode him for 2 hours. He never came. We spent the day with his cock inside me. Hours of endless fucking. I had multiple full body orgasms. He was amazing. He told me he had a rare condition after he cums once he just can’t again but can stay hard for hours. I ended up exhausted and very satisfied. Every 3 days went the same way. He fucked the shit out of me literally, go to the shower then the bed. We destroyed lots of sheets. He was great at passionately making love to me. It always started rough and nasty but ended up being beautiful. Me and daddy fell in love quickly. It was my perfect life. Was...
The love lasted 4 years. One day my daddy changed. Something snapped inside his mind he went from loving dad to brutal slave owner. It wasn’t gradual it was instant. We were drinking one night and I had too much to drink I blacked out. I woke up the next morning naked and afraid. I was locked in a iron cage. It was 8’ long 5’ wide and only 5’ tall. I couldn’t fully stand up . In the corner was a large tub full of cat litter. There was a sink faucet I could drink from and some of the dirty ruined sheets and blankets covered the floor. It smelled of musk. I was humiliated as I hovered over the litter pan going to the bathroom. No toilet paper no wipes I had to use the sheets. I spent the day wondering what happened. I had no idea what time it was, there was no windows in the dungeon. In the far corner from the cage was a wall less shower. A toilet. Torture devices every where . Shackles on the walls. It was a dungeon.
I heard the door open. Daddy stood the smiling. Asking how I was.
What the fuck is going on I asked.
Two options he said as he unlocked the cage. He led me to the center of the room shackles my ankles to the floor my wrists to the ceiling. My body trembling in fear. Daddy grabbed a whip from the wall. The whip flew at me wrapping around my waist stinging my tummy. I cried out from the pain. Over and over he whipped me. My back, ass and stomach covered in deep red marks. After he was satisfied he pulled his cock out spits on it and rams it in my ass hard. No lube I was in tears. He loved it. He fucked me hard and long standing. I was in terrible pain but my cock dripped excessively . He fucked me for hours without orgasm. He pulled my hair pinched my nipples, spanking my entire body hard including my face. It was brutal and terrible but still I had full body orgasms over and over. My mind hated it but my body craved it. I never been in so much pain in my life. After he finally came he unshackled my wrist and I dropped to the floor. He presented his stained cock. Suck it!
It wasn’t covered like before but it was disgusting and I would do anything to stop the torture. The beating and fucking lasted forever. When he was finally finished he sat down next to me. Do you still love daddy he asked
Yes daddy I still love you I cried
Good girl so you have 2 options.
1. This is your life now living in a cage with only a litter pan and daily torture.
2. Volunteer to be my first surgery to change your gender permanently. Removing your testicles and cock making you a pussy. You will be my lover for the rest of our lives upstairs and this dungeon will be dismantled.
You have till tomorrow to decide. Here’s a journal for you to write in. Now I sit here writing hoping if I’m no longer someone will find this. I have to decide now. He’s not a surgeon .
What should I do?
Nova
- 08.07.2021
- 16
- 0
