The Way it is Now CH7
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Lisa's Sessions Ch.7 Hart Breaks My Ass free porn video
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7. Hart Breaks My Ass
I continued my story of the very first ‘special uncle’ session with the older man I knew as “Principal Hart.”
After only a few minutes ‘Principal’ Hart had me stand in front of him and remove the tattered remains of my clothes. This excited him. He began to harden. Looking back, I am sure he was a Viagra user, because he was hard only about twenty minutes after a pretty deep fuck.
I stood before Hart, naked, wet, and with a face of smeared makeup. My eyes were dark blobs, my lipstick was smeared outward from the dies and down over my chin. My hair was pulled in odd ways. My eye shadow, a mix of dark and light blues and my blush were still in place. Hart made no offer to have me clean up or fix my makeup.
As I stood there he began having me model my small girly body in different poses. He had me stretch like a gymnast and stand like a model. As I did, I began to notice my pussy was leaking a slick mess down my inner thighs. Hart had cum inside me. I was confident that I would not be pregnant, but I was still embarrassed by the humiliation of not being able to control my own body.
“There, my dear little school girl whore. That’s what I have been waiting for,” Hart said with a demonic grin. “I love to see your little pussy leak my cum out.” He paused and then said, “Lick it up. Use your hand and wipe it on your tongue.”
I hesitated, and he leaned forward and slapped my face, harder than Karl did, and I nearly began to ball. Then he touched my clit and smiled. It was a very fire and ice, warm and cold, pain and pleasure feeling that was intense. My clit quivered as my face burned the pain of the slap away.
“Now, you have been a good little whore so far, but don’t forget who is in charge. I am. When I tell you to do something, you better fucking do it, and immediately, without hesitation, I mean it. I will beat that into you if I have to. Do you hear me Lisa?”
I nodded and slid my hands from my ‘hands on my hips’ pose on my waist downward to my crotch and then to my inner thighs where they met my small young hairless vagina. I was amazed at how slick and wet I was. Hart seemed to cum more than Karl, it was everywhere and more was oozing out. I wiped my fingers in the carnal cocktail and then licked one hand and then the other.
Hart, still with an evil grin said in a low voice, “Yes, that’s it, lick me off you. Good little fuck toy. Good little whore.” I did that for a while and finally noticed that my pussy was now adding to the mix and that I was turned on. My face was no longer heated form the slap, but now was moving toward warm lusty heat. Hart saw it. He stood up and took off his clothes, folding them nicely while still instructing me to touch myself and lick the fluids.
Hart was naked and his body appeared aged, but not old. He was fit and made me think about those older men who ride bicycles on the weekend, fit, and well traveled. A few stretch marks and wrinkles, but not weak or flabby. He was almost as hairless as I was.
Hart reached out and told me to rub myself with one hand while he took my other. He had me touch his dick and stroke him. He had me hold and softly grip his balls. He took my hand and moved it all over his body, always watching the tiny adolescent hand as it moved.
He had me touch him for several minutes and then led me by my hand to my bedroom. I wondered how he knew where it was and then realized that he must have been here before, perhaps many times.
Once in my pretty girly bedroom, his demeanor changed. He looked me in a mean way. And began asking questions and accusing me of lying to him. “How much did you charge the physical education teacher for a blowjob?”
He caught me off guard and I said, “twenty dollars.”
“Liar!” and then he smacked my ass hard. I felt it begin to welt again.
I was accused of lie after lie until he shoved me to the floor. I turned around and looked up at him. He grabbed a large bottle of lubricant that looked like the bottle from my backpack and opened it. He up-ended it and told me to turn over. As I turned over the first glob landed on my left hip and then a trail went to my ass crack. He emptied the entire thing and then kneeled and straddled my small four-foot tall 85 pound frame. I felt his cock being aimed at my pussy and then pushing into me. He was different this time. He was rough and a bit violent. His cock rammed me deep and in a way that did not feel good to me, but still yielded an orgasm. I began to cum again and again. Then he pulled out and wiped his dick in the slick mess of the lubricant. He moved his cock and then I felt him wipe his hands in the slick mess. I peeked a look at him in one of the many mirrors positioned throughout the room to see the action, and saw him wiping the lube all over his naked torso. He then put one hand on the floor to lower himself onto me and as the other gripped his ample seven inch dick. The hand on the floor reached up and gripped my mouth, as he’d done in the earlier in the office, but not hard enough to cut off my breathing. He held only a small portion of his crushing body weight as he began to work his adult cock into my young ass.
“Aiiieeeeeee!!!” I screamed into his hand. His cock, although not huge, at the time felt like it was a telephone pole. He stretched me and nearly tore me in the very first thrust.
“Ahhh!! Ahiiieeeieie! Nnnoooooo!” I screamed. “Noooo! It’s too big!!!”
This intensified the experience and made him force himself into me deeper and harder. He may not have actually been larger than Karl, but I was unprepared for an ass-fuck. Then I realized that this was my first real ass-****. It hurt, but the realization was delightful on some level. Despite the revelation and demented pride and pleasure I felt, I was in real pain and wanted to stop.
Hart moved the hand that had guided his dick into my small frame to my small cunt and inserted a finger into my shallow vagina in such a manner that part of it was also pressing and rubbing my larger-than-average clitoris. He began forcing me to orgasm.
His other hand held my face with an iron grip and even pulled my head backward and into his chest. He loved me screaming into his hand. He loved inflicting the special humiliating pain of the ass****. Soon he increased his pace and fucked me deep, hard, and fast. I became concerned when I felt myself relax and begin to like it. I was worried that since I had not properly cleaned myself out with multiple ass-douched that I would make a mess, but it never happened.
Then Hart became even creepier. He let go of my mouth and face and allowed me to scream or moan the pain away and began saying things directly into my ear. As my yelps of genuine pain echoed in the room he started saying disturbing and taboo things to me. “Yess, that’s a good little whore-girl. Taking it in her ass like a good little girl is supposed to. Taking it like a good little boy…you like being fucked in your ass don’t you? Of course…you like being fucked like a little boy don’t you? Of course you do. Yesssss…you crave a man assr****g you…you dream of it…and you always will…you love being fucked like a dirty little boy…”
On one level he forced extremely taboo things to pass though my head as he fucked me. On another level, and since I had seen videos that Karl had made me watch, of younger boys taking older men, I was turned on. I was a massive orgasmic mess, but this took me new places. Hart’s pace slowed for a minute or two and then he could hold his orgasm back no longer. He crushed me with his weight and left me airless and unable to scream as he thrusted his cum deep into my ass.
Dr. Heard held his hand politely to ask, “So, he fucked you in your ass and on the floor and there were no marks or injuries?”
“Oh, no Doctor, he left me with a bunch if bruises and abrasions. He tore my ass open with a cut that I am told the scar is still visible today. My knees and hips and elbows were all bruised and I had a small cut on my ass cheek from his zipper and the first experience in the office. My throat was sore and I had a big bump on my head from my first orgasm of the day in the office, and during the last session, the last fuck from him before he left at about three in the morning, I bit my tongue by mistake.” I paused and then said, “Add to that the mouth to pussy to ass to mouth fuck Karl did with me after Hart left, and I was in pain. I was well used though. And I loved it.”
“Ok. That is amazing and your attitude about this is, well uncommonly wonderful… Just briefly, since we are nearly out of time for this session, what, or how was the last bit of your time with Hart spent?”
“Oh, he came in my ass, pulled out, made me lick his cum off his dick and then watched me take a shower and clean myself. He douched my little pussy and my little asshole and got hard again.
He had me dress in the Cinderella costume and jacked off on my face and then watched me wash off again.
He dressed me in a small white nightgown, you know like a bride might wear on her wedding night, and then we slept for a few hours. He woke up, got hard and I woke to him forcing his cock into me and then fucking me hard missionary style. He shot the first part of this load inside me and then jacked himself on my face and made me wipe my face and feed myself his cum as he slowly finished himself off.
Then he made me take a shower with him once more and finger fucked me to another few orgasms before he sent me to my bed and he got ready to leave. He gave me a peck on the cheek, told me I was very special and that he loved me, and then left.
“Did you ever see him again?”
“Yes, only once. We played out essentially the same bad school-girl scene as we had at Karl’s house, except the second time was in a real school somewhere in the LA basin, and really late at night during the summer. Actually, that was one of the few times Karl fucked me somewhere else too. It seems that Hart really was a school principal that liked little girls…and boys…a lot.”
“Oh my goodness. Did Karl and Hart ever play with you at the same time?”
“No. Actually, I’m not sure I could have handled that intense of a scene at that age.”
“I suppose not.” He paused and then said, “So, it seems that these things with your special uncles are some of the things you are concerned about regarding the law. You can be assured that I will be discreet.”
I laughed, and said, “Doctor, you are way off. This barely scratches the surface.”
As I left, Nancy, the receptionist, met me in the bathroom and gave me some incredible head that served as an appetizer. Two hours later I was swallowing a hard thick eight-incher during a long overdue hardcore reunion with Ken, a partner with the law firm that I worked and whored for. He’d been the first to discover my whoring while on trips with the firm. At the time he was a junior partner, now he was a senior partner and the director of the firm. Ken had been instrumental in converting my carnal moonlighting into the naughty-trick consulting that I had continued all my adult life. That night, Ken I pretty-much fucked like we had when I was a young intern with the firm for about a half hour – wearing a dark blue blazer and pencil skirt with a white blouse. After he came I was disheveled and looked exactly as I was- a Lawyer that had just been fucked by a colleague. I actually was not a lawyer, I had finished the degree, but never took the bar exam.
I left him on the hotel couch of his suite and got ready for the next part of our play. About twenty minutes later he got what he still really needed from me after all these years. Ken had discovered me, but later on I discovered him and his fetish. I walked out of the over-sized white ornate bathroom as a living contrast. Black shiny leather adorned my white skin. My red hair framed my gothic dark eyes. I held a collar and a crop in one hand and walked in my over-the-knee high stiletto boots. And with every movement a thick heavy chocolate-brown eight-inch cock strapped to my crotchless harness bounced side to side and up and down.
I leered at him sternly and struck his inner thigh with the crop hard enough to welt his tanned leg and said, “Get the fuck on your knees you fucking r****t and prepare to get fucked hard….”
I got in about midnight and Harold ate me out, as I told him first about Nancy and then all of the things I’d done to Ken. Harold enjoyed Ken’s cum as a bonus.
7. Hart Breaks My Ass
I continued my story of the very first ‘special uncle’ session with the older man I knew as “Principal Hart.”
After only a few minutes ‘Principal’ Hart had me stand in front of him and remove the tattered remains of my clothes. This excited him. He began to harden. Looking back, I am sure he was a Viagra user, because he was hard only about twenty minutes after a pretty deep fuck.
I stood before Hart, naked, wet, and with a face of smeared makeup. My eyes were dark blobs, my lipstick was smeared outward from the dies and down over my chin. My hair was pulled in odd ways. My eye shadow, a mix of dark and light blues and my blush were still in place. Hart made no offer to have me clean up or fix my makeup.
As I stood there he began having me model my small girly body in different poses. He had me stretch like a gymnast and stand like a model. As I did, I began to notice my pussy was leaking a slick mess down my inner thighs. Hart had cum inside me. I was confident that I would not be pregnant, but I was still embarrassed by the humiliation of not being able to control my own body.
“There, my dear little school girl whore. That’s what I have been waiting for,” Hart said with a demonic grin. “I love to see your little pussy leak my cum out.” He paused and then said, “Lick it up. Use your hand and wipe it on your tongue.”
I hesitated, and he leaned forward and slapped my face, harder than Karl did, and I nearly began to ball. Then he touched my clit and smiled. It was a very fire and ice, warm and cold, pain and pleasure feeling that was intense. My clit quivered as my face burned the pain of the slap away.
“Now, you have been a good little whore so far, but don’t forget who is in charge. I am. When I tell you to do something, you better fucking do it, and immediately, without hesitation, I mean it. I will beat that into you if I have to. Do you hear me Lisa?”
I nodded and slid my hands from my ‘hands on my hips’ pose on my waist downward to my crotch and then to my inner thighs where they met my small young hairless vagina. I was amazed at how slick and wet I was. Hart seemed to cum more than Karl, it was everywhere and more was oozing out. I wiped my fingers in the carnal cocktail and then licked one hand and then the other.
Hart, still with an evil grin said in a low voice, “Yes, that’s it, lick me off you. Good little fuck toy. Good little whore.” I did that for a while and finally noticed that my pussy was now adding to the mix and that I was turned on. My face was no longer heated form the slap, but now was moving toward warm lusty heat. Hart saw it. He stood up and took off his clothes, folding them nicely while still instructing me to touch myself and lick the fluids.
Hart was naked and his body appeared aged, but not old. He was fit and made me think about those older men who ride bicycles on the weekend, fit, and well traveled. A few stretch marks and wrinkles, but not weak or flabby. He was almost as hairless as I was.
Hart reached out and told me to rub myself with one hand while he took my other. He had me touch his dick and stroke him. He had me hold and softly grip his balls. He took my hand and moved it all over his body, always watching the tiny adolescent hand as it moved.
He had me touch him for several minutes and then led me by my hand to my bedroom. I wondered how he knew where it was and then realized that he must have been here before, perhaps many times.
Once in my pretty girly bedroom, his demeanor changed. He looked me in a mean way. And began asking questions and accusing me of lying to him. “How much did you charge the physical education teacher for a blowjob?”
He caught me off guard and I said, “twenty dollars.”
“Liar!” and then he smacked my ass hard. I felt it begin to welt again.
I was accused of lie after lie until he shoved me to the floor. I turned around and looked up at him. He grabbed a large bottle of lubricant that looked like the bottle from my backpack and opened it. He up-ended it and told me to turn over. As I turned over the first glob landed on my left hip and then a trail went to my ass crack. He emptied the entire thing and then kneeled and straddled my small four-foot tall 85 pound frame. I felt his cock being aimed at my pussy and then pushing into me. He was different this time. He was rough and a bit violent. His cock rammed me deep and in a way that did not feel good to me, but still yielded an orgasm. I began to cum again and again. Then he pulled out and wiped his dick in the slick mess of the lubricant. He moved his cock and then I felt him wipe his hands in the slick mess. I peeked a look at him in one of the many mirrors positioned throughout the room to see the action, and saw him wiping the lube all over his naked torso. He then put one hand on the floor to lower himself onto me and as the other gripped his ample seven inch dick. The hand on the floor reached up and gripped my mouth, as he’d done in the earlier in the office, but not hard enough to cut off my breathing. He held only a small portion of his crushing body weight as he began to work his adult cock into my young ass.
“Aiiieeeeeee!!!” I screamed into his hand. His cock, although not huge, at the time felt like it was a telephone pole. He stretched me and nearly tore me in the very first thrust.
“Ahhh!! Ahiiieeeieie! Nnnoooooo!” I screamed. “Noooo! It’s too big!!!”
This intensified the experience and made him force himself into me deeper and harder. He may not have actually been larger than Karl, but I was unprepared for an ass-fuck. Then I realized that this was my first real ass-****. It hurt, but the realization was delightful on some level. Despite the revelation and demented pride and pleasure I felt, I was in real pain and wanted to stop.
Hart moved the hand that had guided his dick into my small frame to my small cunt and inserted a finger into my shallow vagina in such a manner that part of it was also pressing and rubbing my larger-than-average clitoris. He began forcing me to orgasm.
His other hand held my face with an iron grip and even pulled my head backward and into his chest. He loved me screaming into his hand. He loved inflicting the special humiliating pain of the ass****. Soon he increased his pace and fucked me deep, hard, and fast. I became concerned when I felt myself relax and begin to like it. I was worried that since I had not properly cleaned myself out with multiple ass-douched that I would make a mess, but it never happened.
Then Hart became even creepier. He let go of my mouth and face and allowed me to scream or moan the pain away and began saying things directly into my ear. As my yelps of genuine pain echoed in the room he started saying disturbing and taboo things to me. “Yess, that’s a good little whore-girl. Taking it in her ass like a good little girl is supposed to. Taking it like a good little boy…you like being fucked in your ass don’t you? Of course…you like being fucked like a little boy don’t you? Of course you do. Yesssss…you crave a man assr****g you…you dream of it…and you always will…you love being fucked like a dirty little boy…”
On one level he forced extremely taboo things to pass though my head as he fucked me. On another level, and since I had seen videos that Karl had made me watch, of younger boys taking older men, I was turned on. I was a massive orgasmic mess, but this took me new places. Hart’s pace slowed for a minute or two and then he could hold his orgasm back no longer. He crushed me with his weight and left me airless and unable to scream as he thrusted his cum deep into my ass.
Dr. Heard held his hand politely to ask, “So, he fucked you in your ass and on the floor and there were no marks or injuries?”
“Oh, no Doctor, he left me with a bunch if bruises and abrasions. He tore my ass open with a cut that I am told the scar is still visible today. My knees and hips and elbows were all bruised and I had a small cut on my ass cheek from his zipper and the first experience in the office. My throat was sore and I had a big bump on my head from my first orgasm of the day in the office, and during the last session, the last fuck from him before he left at about three in the morning, I bit my tongue by mistake.” I paused and then said, “Add to that the mouth to pussy to ass to mouth fuck Karl did with me after Hart left, and I was in pain. I was well used though. And I loved it.”
“Ok. That is amazing and your attitude about this is, well uncommonly wonderful… Just briefly, since we are nearly out of time for this session, what, or how was the last bit of your time with Hart spent?”
“Oh, he came in my ass, pulled out, made me lick his cum off his dick and then watched me take a shower and clean myself. He douched my little pussy and my little asshole and got hard again.
He had me dress in the Cinderella costume and jacked off on my face and then watched me wash off again.
He dressed me in a small white nightgown, you know like a bride might wear on her wedding night, and then we slept for a few hours. He woke up, got hard and I woke to him forcing his cock into me and then fucking me hard missionary style. He shot the first part of this load inside me and then jacked himself on my face and made me wipe my face and feed myself his cum as he slowly finished himself off.
Then he made me take a shower with him once more and finger fucked me to another few orgasms before he sent me to my bed and he got ready to leave. He gave me a peck on the cheek, told me I was very special and that he loved me, and then left.
“Did you ever see him again?”
“Yes, only once. We played out essentially the same bad school-girl scene as we had at Karl’s house, except the second time was in a real school somewhere in the LA basin, and really late at night during the summer. Actually, that was one of the few times Karl fucked me somewhere else too. It seems that Hart really was a school principal that liked little girls…and boys…a lot.”
“Oh my goodness. Did Karl and Hart ever play with you at the same time?”
“No. Actually, I’m not sure I could have handled that intense of a scene at that age.”
“I suppose not.” He paused and then said, “So, it seems that these things with your special uncles are some of the things you are concerned about regarding the law. You can be assured that I will be discreet.”
I laughed, and said, “Doctor, you are way off. This barely scratches the surface.”
As I left, Nancy, the receptionist, met me in the bathroom and gave me some incredible head that served as an appetizer. Two hours later I was swallowing a hard thick eight-incher during a long overdue hardcore reunion with Ken, a partner with the law firm that I worked and whored for. He’d been the first to discover my whoring while on trips with the firm. At the time he was a junior partner, now he was a senior partner and the director of the firm. Ken had been instrumental in converting my carnal moonlighting into the naughty-trick consulting that I had continued all my adult life. That night, Ken I pretty-much fucked like we had when I was a young intern with the firm for about a half hour – wearing a dark blue blazer and pencil skirt with a white blouse. After he came I was disheveled and looked exactly as I was- a Lawyer that had just been fucked by a colleague. I actually was not a lawyer, I had finished the degree, but never took the bar exam.
I left him on the hotel couch of his suite and got ready for the next part of our play. About twenty minutes later he got what he still really needed from me after all these years. Ken had discovered me, but later on I discovered him and his fetish. I walked out of the over-sized white ornate bathroom as a living contrast. Black shiny leather adorned my white skin. My red hair framed my gothic dark eyes. I held a collar and a crop in one hand and walked in my over-the-knee high stiletto boots. And with every movement a thick heavy chocolate-brown eight-inch cock strapped to my crotchless harness bounced side to side and up and down.
I leered at him sternly and struck his inner thigh with the crop hard enough to welt his tanned leg and said, “Get the fuck on your knees you fucking r****t and prepare to get fucked hard….”
I got in about midnight and Harold ate me out, as I told him first about Nancy and then all of the things I’d done to Ken. Harold enjoyed Ken’s cum as a bonus.
Mikhaela
- 05.08.2021
- 41
- 0
