Sissy Starr Is the Prison Bitch
I have been in and out jails, and prison until my last release in 2001. The first time I was 18 when I went to prison I am not sure what led me down that road… it was a different time, and the world was very different. I never really fit in. I never really found a way to fit in either. The struggles led to alot of bad decisions. Confused thinking… probably a familiar story now.
I was young, very slim, hairless, feminine when I was sent to prison. It was the 80s big hair, rock n roll, d**gs and sex. I was far from helpless. lol I was in fact, a very violent person even then. However, prison was a world full of tough guys. It was a world that I would eventually learn to survive in.
I was moved from Quarantine to a Prison Psych Hospital within 60 days of my arrival. For further observation and testing. My mind was a mess…it was scary as the decisions I made at this time would follow me everywhere in prison. There really are no secrets in prison, and everyone is some type of predator looking for weakness. Even the inmates at the hospital knew that I had arrived at the prison dressed like a girl.
I received countless kites (notes) from inmates from day one. The short version, some promised protection in lou of sexual favors, others offered money for the same, and some promised violent ****. Everyone waited to see how I would respond. Deep in my heart I knew, and I knew before I was sent here that I would not survive my entire sentence without someone fucking me. The only real question was did I decide or would someone else decide for me…. who would be in control.
Sissy Starr Is the Prison Bitch, Sissy Photo Stories
It was alot to think about. I was not interested in being ****d… some died from it and the beatings associated with **** were brutal. Further, if I was ****d I did not want the r****t to have the power of seeing me weak, screaming or crying… I had to take that power away from him… silently I knew that I would have to be “broke in” I began to evaluate guys trying to figure out who would be discreet and gentle.
Shortly after I had decided this course, I was moved to a five man dorm setting but there was only three of us there. Terry a black guy much older then myself was already my friend and in the dorm the other guy was heavily medicated.
I decided that I would ask my friend to break me in… It was a risk, I had no idea if he would, he never led me to think this way,… I wrote a note. That stupid note changed everything. I was no longer a friend… I was a prize. Negotiations between us followed. In the end we struck a deal… he would be very gentle with me and break me in, and discreet but I would shave like a girl, dress up for him, he would break me in then I’d submit to him the rest of the night. I had to write a note declaring that this was not **** and I asked him to do it. Sign it. I knew that everything was changing…
It was like watching my life from from outside myself. I could not believe that I was in this position. I was sinking into depression as I stared down at my life unfolding. He was very eager and I was nervous. He watched with lusting eyes as I prepared myself that evening. Shaving, showering, douche, make up and finally just panties and a t shirt. I laid there in my bed thinking as we waited… waited for lights out… waited for our roommates d**gs to kick in and hed be asleep… waited for the guard to make his round.
I was a man of my word, and as the guard passed, I got out of my bed… placed a blanket on the floor between the beds out of sight… Terry was already touching himself… I couldn’t help myself I had cut my eyes and seen him. It was dark (lights out) but there was a slim beam of light from the small window in the steel door that allowed me to see non detailed shapes across the room.
Sissy Starr Is the Prison Bitch, Sissy Photo Stories
I was very nervous…. There was no turning back and everything could change. I was torn…I wanted to back out before it happened and part of me just wanted to be done with it. ” No, I had to back out” I turned to say something and was caught off guard as Terry was standing next to me already. Before I could tell him that I had changed my mind he had wrapped his arms around me and pulled me tightly against him pressing his lips to mine… My small frame seemed to melt in his embrace… I was not expecting that!
He was treating me like he would a girl… his hands gripped my butt tightly and pulled me against him. I could feel his excitement against my belly through my shirt. In that moment my mind said that I was a girl… I felt like a girl. he was a foot taller then i was…. stronger. My slim 5 ft 5 frame at 119 lbs was over come with a sense of femininity as it melted against him.
He broke from my lips and without a word I knew that it was time.
He was already lowering his pants as I turned away and pulled my panties down, slowly got on the floor before him…. Laid down on the carefully spread blanket face down…. i placed a pillow under my mid section to raise nak** butt in the air slightly offering myself to him as he stood over me.
One last look back at him towering there naked… now I was scared again he was much larger then i was. I was sure that this was going to hurt. As he gently kicked my feet apart spreading my legs , and lowered himself down onto my back… my mind screamed ” You’re a damm fool. No one asked to be turned out. Now you’re going to spend your life as a fuck boy, a sissy prison bitch”
My self critical thoughts were interrupted by his weight on me. I felt the coarse hair of his legs against my smooth shaved legs…. closing my eyes I felt everything as if in slow motion…. the hard dick pressed against my ass pulsating, all of his weight crushing me covering me…. the hair on his chest against my back even through the shirts thin material…. i seemed so small beneath him. His hand brushing the long hair from my neck and his lips … the hot breath on my shoulder as he kissed my neck and shoulder before whispering in my ear, ” are you ready?”
Sissy Starr Is the Prison Bitch, Sissy Photo Stories
No need to answer that and he didn’t wait for me to respond. His weight lifted and his hands trailed down my back as he knelt between my spread legs. his strong hands pushed the bottom of my shirt up over my nak** butt to my waist, as if it was a skirt. they gripped my cheeks and pushed them apart exposing my near virgin hole to his lustful gaze. I just lay there as he poured Baby Oil down the crack of my ass, his hand working in being sure that i was “wet” He lubed his rock hard with desire dick, as I reached back like a wanton whore grasping it pulling it toward me. He lowered himself back down on my back and I guided him home.
Its tip pressed against me… suddenly he was in me. I gasped at the suddenness of it. I held my breath to keep from crying out. As I struggled to take it in and adjust to its size. I wanted to scream… to stop… OMG what had I gotten myself into… My entire body was tense even my toes were curled up and my hands gripped the blanket… he pressed forward, and I realized that he barely in me. Tears welled in my eyes as he slowly pushed his way in… all the way in. He whispered, “relax” I tried but it was still several minutes before I adjusted to his size and the overwhelming pain began to ease allowing to breath.
He must have sensed that, as he began to pull out… then back in. My mind raced with thoughts now that i could breath. I was seeing it as if I was floating above us… my small feminine form beneath him, legs spread… him pumping away and holding me… I felt him sliding in and out of me. Felt his desire and needs for release… muscles tensing… pelvic thrusting against my ass… hot breath on my neck… sweat dripping on me from his labors… I rolled my ankles out opening myself wider for him inviting him deeper.
Sissy Starr Is the Prison Bitch, Sissy Photo Stories
There was no turning back now… I was a bitch. He was pounding away grinding … there was no more pain. His breathing was labored, and I could feel his dick starting to pulsate… I knew that he was getting ready to cum… totally shocking myself, I blurted out, ” cum in me” and he did. then collapsed on my back exhausted from turning me into a bitch.
When he had composed himself, he pulled out of me… i suddenly felt empty, his spent juice oozing out slightly in the cool evening air. As I stood I could feel it dripping running down my inner thigh and walked over to toilet area to wipe. When I turned around I saw him staring at me… It was almost time for the guard to make another round, and I pulled my panties back on. It was done… I had been broke in and it wasn’t so bad… i returned to my bed where I laid thinking.
I laid there knowing that I had changed everything… i was cussing myself out for being weak. Now I had become the sissy prison bitch. Judging myself harshly. Hating that I was willing. telling myself over and over how stupid I was… but excited by the idea of a life here in prison as a girl. I couldn’t handle being seen as a bitch… I had liked it and it was too late now anyways, I had dressed like a girl and basically begged a grown man to cum in my ass… My self judgement was interrupted by the guards flashlight in the window checking on us…
As the guard passed,I got up and went to the sink to better clean up, turned the water on and wet the wash clothe before pulling my panties down to clean up. As I wondered if Terry was still awake, I was startled by his hands around my waist. I felt his hard cock slide between my cheeks across my tenderness… he was clearly awake…. he bent me over the sink right there ready to collect his end of the bargain… “… I’d submit to him the rest of the night”
With my panties around my knees, he pushed my feet apart and I remained bent over the sink submitting to him as agreed. He easily entered me this time and wasted no time… it was his reward. Without a word he took what was his… it was all I could do to just brace myself as he pounded away at his treasure…
Truly, I didn’t not feel like a guy… i felt like a bitch… he was pounding my pussy for what seemed like an eternity before a deep thrust… he was quivering as i felt the now familiar pulse of him cumming followed by the wetness of my hole… his hands grasped my naked, stretched ass cheeks… pulling them apart so he could view himself buried spent deep inside me. I can only imagine what it may have looked like… he seemed happy to be there…
prison bitch
He slid his cock in and out of my gaping, wet cunt for a while as his cock started to shrink and then I felt him pull out…. the spent juice again dripping down my thighs…I tried to wipe but it was just kept oozing out. Knowing I was full of cum and my pussy was not tightening back up as before… I stepped out of my panties and went over to the toilet to try and push his cum out of me. He followed me … my mind screamed, ” Damm you’re not done”
As I sat down, he walked right up to me…his softening dick glistened in the window light… he smelt of sex. Heavy musky scent combined with baby oil. I felt so submissive… so feminine. He pushed his mid section toward me until the tip of his dick touched my lips… I hadnt thought about this occurring. I just assumed fucking me was the thing… his hands caressed my long hair as I parted my lips slightly and he pushed himself past them into my mouth. the smell was repulsive… I wanted to pull away. He must of sensed it as he gripped my head tighter… almost like I knew what to do my hands went to his thighs and I began to relax… my nose against his belly my tongue caressed the bottom of his dick. It jumped in my mouth and began to harden. As I started to apply sucking and his grip lessened on my head. I looked up in the darkness as if seeking his approval. I began to instinctive do what was being asked of me. my hand grasped his member, my tongue feverishly licked and caressed it as my lips held it firmly sliding up and down its shaft… eagerly sucking it back to life…my eyes searching begging for a sign that I was being a good girl seeking his approval.
It didn’t take long for him to be rock hard in my warm loving mouth, then throbbing , jumping and pulsating as he exploded. it tasted salty and thick and smelt heavy… tears ran down my cheeks as i choked gagged but swallowed his spent cum…. I had never knelt before a man, much less had dick in my mouth…
Sissy Starr Is the Prison Bitch, Sissy Photo Stories
What a pathetic man I had chose to be… even now I imagine the scene… 18 yr old k**, 119 lbs, 5 5 slim feminine long hair, white shirt smooth soft legs escaping beneath it. seated on a toilet, cum dripping from his ass, mid thirties hairy black man, standing before him, hard dick shoved in the tear streaked face… cum dribbling across the red lips… it was not a vision that I would see for long as he was not done… lifting me up from my submissive position I turned away… tired but willing i spread my legs wide and bent over the toilet so he could take me again… he did.
That is how my first time in prison went. That one night changed my life forever. It did not take long for those events to be known… I could not hide the fact that my legs were shaved and with group showers it was quickly noticed. Within a matter of days, even outside of the hospital, in the general population of Riverside correctional facility everyone was talking about the “fine ass sissy” in the psych ward…
I was young, very slim, hairless, feminine when I was sent to prison. It was the 80s big hair, rock n roll, d**gs and sex. I was far from helpless. lol I was in fact, a very violent person even then. However, prison was a world full of tough guys. It was a world that I would eventually learn to survive in.
I was moved from Quarantine to a Prison Psych Hospital within 60 days of my arrival. For further observation and testing. My mind was a mess…it was scary as the decisions I made at this time would follow me everywhere in prison. There really are no secrets in prison, and everyone is some type of predator looking for weakness. Even the inmates at the hospital knew that I had arrived at the prison dressed like a girl.
I received countless kites (notes) from inmates from day one. The short version, some promised protection in lou of sexual favors, others offered money for the same, and some promised violent ****. Everyone waited to see how I would respond. Deep in my heart I knew, and I knew before I was sent here that I would not survive my entire sentence without someone fucking me. The only real question was did I decide or would someone else decide for me…. who would be in control.
Sissy Starr Is the Prison Bitch, Sissy Photo Stories
It was alot to think about. I was not interested in being ****d… some died from it and the beatings associated with **** were brutal. Further, if I was ****d I did not want the r****t to have the power of seeing me weak, screaming or crying… I had to take that power away from him… silently I knew that I would have to be “broke in” I began to evaluate guys trying to figure out who would be discreet and gentle.
Shortly after I had decided this course, I was moved to a five man dorm setting but there was only three of us there. Terry a black guy much older then myself was already my friend and in the dorm the other guy was heavily medicated.
I decided that I would ask my friend to break me in… It was a risk, I had no idea if he would, he never led me to think this way,… I wrote a note. That stupid note changed everything. I was no longer a friend… I was a prize. Negotiations between us followed. In the end we struck a deal… he would be very gentle with me and break me in, and discreet but I would shave like a girl, dress up for him, he would break me in then I’d submit to him the rest of the night. I had to write a note declaring that this was not **** and I asked him to do it. Sign it. I knew that everything was changing…
It was like watching my life from from outside myself. I could not believe that I was in this position. I was sinking into depression as I stared down at my life unfolding. He was very eager and I was nervous. He watched with lusting eyes as I prepared myself that evening. Shaving, showering, douche, make up and finally just panties and a t shirt. I laid there in my bed thinking as we waited… waited for lights out… waited for our roommates d**gs to kick in and hed be asleep… waited for the guard to make his round.
I was a man of my word, and as the guard passed, I got out of my bed… placed a blanket on the floor between the beds out of sight… Terry was already touching himself… I couldn’t help myself I had cut my eyes and seen him. It was dark (lights out) but there was a slim beam of light from the small window in the steel door that allowed me to see non detailed shapes across the room.
Sissy Starr Is the Prison Bitch, Sissy Photo Stories
I was very nervous…. There was no turning back and everything could change. I was torn…I wanted to back out before it happened and part of me just wanted to be done with it. ” No, I had to back out” I turned to say something and was caught off guard as Terry was standing next to me already. Before I could tell him that I had changed my mind he had wrapped his arms around me and pulled me tightly against him pressing his lips to mine… My small frame seemed to melt in his embrace… I was not expecting that!
He was treating me like he would a girl… his hands gripped my butt tightly and pulled me against him. I could feel his excitement against my belly through my shirt. In that moment my mind said that I was a girl… I felt like a girl. he was a foot taller then i was…. stronger. My slim 5 ft 5 frame at 119 lbs was over come with a sense of femininity as it melted against him.
He broke from my lips and without a word I knew that it was time.
He was already lowering his pants as I turned away and pulled my panties down, slowly got on the floor before him…. Laid down on the carefully spread blanket face down…. i placed a pillow under my mid section to raise nak** butt in the air slightly offering myself to him as he stood over me.
One last look back at him towering there naked… now I was scared again he was much larger then i was. I was sure that this was going to hurt. As he gently kicked my feet apart spreading my legs , and lowered himself down onto my back… my mind screamed ” You’re a damm fool. No one asked to be turned out. Now you’re going to spend your life as a fuck boy, a sissy prison bitch”
My self critical thoughts were interrupted by his weight on me. I felt the coarse hair of his legs against my smooth shaved legs…. closing my eyes I felt everything as if in slow motion…. the hard dick pressed against my ass pulsating, all of his weight crushing me covering me…. the hair on his chest against my back even through the shirts thin material…. i seemed so small beneath him. His hand brushing the long hair from my neck and his lips … the hot breath on my shoulder as he kissed my neck and shoulder before whispering in my ear, ” are you ready?”
Sissy Starr Is the Prison Bitch, Sissy Photo Stories
No need to answer that and he didn’t wait for me to respond. His weight lifted and his hands trailed down my back as he knelt between my spread legs. his strong hands pushed the bottom of my shirt up over my nak** butt to my waist, as if it was a skirt. they gripped my cheeks and pushed them apart exposing my near virgin hole to his lustful gaze. I just lay there as he poured Baby Oil down the crack of my ass, his hand working in being sure that i was “wet” He lubed his rock hard with desire dick, as I reached back like a wanton whore grasping it pulling it toward me. He lowered himself back down on my back and I guided him home.
Its tip pressed against me… suddenly he was in me. I gasped at the suddenness of it. I held my breath to keep from crying out. As I struggled to take it in and adjust to its size. I wanted to scream… to stop… OMG what had I gotten myself into… My entire body was tense even my toes were curled up and my hands gripped the blanket… he pressed forward, and I realized that he barely in me. Tears welled in my eyes as he slowly pushed his way in… all the way in. He whispered, “relax” I tried but it was still several minutes before I adjusted to his size and the overwhelming pain began to ease allowing to breath.
He must have sensed that, as he began to pull out… then back in. My mind raced with thoughts now that i could breath. I was seeing it as if I was floating above us… my small feminine form beneath him, legs spread… him pumping away and holding me… I felt him sliding in and out of me. Felt his desire and needs for release… muscles tensing… pelvic thrusting against my ass… hot breath on my neck… sweat dripping on me from his labors… I rolled my ankles out opening myself wider for him inviting him deeper.
Sissy Starr Is the Prison Bitch, Sissy Photo Stories
There was no turning back now… I was a bitch. He was pounding away grinding … there was no more pain. His breathing was labored, and I could feel his dick starting to pulsate… I knew that he was getting ready to cum… totally shocking myself, I blurted out, ” cum in me” and he did. then collapsed on my back exhausted from turning me into a bitch.
When he had composed himself, he pulled out of me… i suddenly felt empty, his spent juice oozing out slightly in the cool evening air. As I stood I could feel it dripping running down my inner thigh and walked over to toilet area to wipe. When I turned around I saw him staring at me… It was almost time for the guard to make another round, and I pulled my panties back on. It was done… I had been broke in and it wasn’t so bad… i returned to my bed where I laid thinking.
I laid there knowing that I had changed everything… i was cussing myself out for being weak. Now I had become the sissy prison bitch. Judging myself harshly. Hating that I was willing. telling myself over and over how stupid I was… but excited by the idea of a life here in prison as a girl. I couldn’t handle being seen as a bitch… I had liked it and it was too late now anyways, I had dressed like a girl and basically begged a grown man to cum in my ass… My self judgement was interrupted by the guards flashlight in the window checking on us…
As the guard passed,I got up and went to the sink to better clean up, turned the water on and wet the wash clothe before pulling my panties down to clean up. As I wondered if Terry was still awake, I was startled by his hands around my waist. I felt his hard cock slide between my cheeks across my tenderness… he was clearly awake…. he bent me over the sink right there ready to collect his end of the bargain… “… I’d submit to him the rest of the night”
With my panties around my knees, he pushed my feet apart and I remained bent over the sink submitting to him as agreed. He easily entered me this time and wasted no time… it was his reward. Without a word he took what was his… it was all I could do to just brace myself as he pounded away at his treasure…
Truly, I didn’t not feel like a guy… i felt like a bitch… he was pounding my pussy for what seemed like an eternity before a deep thrust… he was quivering as i felt the now familiar pulse of him cumming followed by the wetness of my hole… his hands grasped my naked, stretched ass cheeks… pulling them apart so he could view himself buried spent deep inside me. I can only imagine what it may have looked like… he seemed happy to be there…
prison bitch
He slid his cock in and out of my gaping, wet cunt for a while as his cock started to shrink and then I felt him pull out…. the spent juice again dripping down my thighs…I tried to wipe but it was just kept oozing out. Knowing I was full of cum and my pussy was not tightening back up as before… I stepped out of my panties and went over to the toilet to try and push his cum out of me. He followed me … my mind screamed, ” Damm you’re not done”
As I sat down, he walked right up to me…his softening dick glistened in the window light… he smelt of sex. Heavy musky scent combined with baby oil. I felt so submissive… so feminine. He pushed his mid section toward me until the tip of his dick touched my lips… I hadnt thought about this occurring. I just assumed fucking me was the thing… his hands caressed my long hair as I parted my lips slightly and he pushed himself past them into my mouth. the smell was repulsive… I wanted to pull away. He must of sensed it as he gripped my head tighter… almost like I knew what to do my hands went to his thighs and I began to relax… my nose against his belly my tongue caressed the bottom of his dick. It jumped in my mouth and began to harden. As I started to apply sucking and his grip lessened on my head. I looked up in the darkness as if seeking his approval. I began to instinctive do what was being asked of me. my hand grasped his member, my tongue feverishly licked and caressed it as my lips held it firmly sliding up and down its shaft… eagerly sucking it back to life…my eyes searching begging for a sign that I was being a good girl seeking his approval.
It didn’t take long for him to be rock hard in my warm loving mouth, then throbbing , jumping and pulsating as he exploded. it tasted salty and thick and smelt heavy… tears ran down my cheeks as i choked gagged but swallowed his spent cum…. I had never knelt before a man, much less had dick in my mouth…
Sissy Starr Is the Prison Bitch, Sissy Photo Stories
What a pathetic man I had chose to be… even now I imagine the scene… 18 yr old k**, 119 lbs, 5 5 slim feminine long hair, white shirt smooth soft legs escaping beneath it. seated on a toilet, cum dripping from his ass, mid thirties hairy black man, standing before him, hard dick shoved in the tear streaked face… cum dribbling across the red lips… it was not a vision that I would see for long as he was not done… lifting me up from my submissive position I turned away… tired but willing i spread my legs wide and bent over the toilet so he could take me again… he did.
That is how my first time in prison went. That one night changed my life forever. It did not take long for those events to be known… I could not hide the fact that my legs were shaved and with group showers it was quickly noticed. Within a matter of days, even outside of the hospital, in the general population of Riverside correctional facility everyone was talking about the “fine ass sissy” in the psych ward…
2 tahun lalu
