Lisa s Confession Sessions Prelude
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Lisa’s Confession Sessions
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Prelude
I was still numb, tasted cum, and was still a bit fuzzy in the head. I could hardly believe I had just blown the cock of a top Las Vegas Psychologist in his office...during a session. A lot had happened and I was still trying to understand.
The psychologist, Dr. Heard, had been asked to both present the full offer from my ‘benefactor’, more of a sugar-daddy-cuckhold, and record the story of my life, a confession really. “You are making me tell everything that has happened to me? Why? Does this give him some perverse insight or closure? What if I refuse?”
“I am not making you do anything. If you refuse he will not hold to his benefactor agreement with you. You will remain his guest, if you like, but you will not, in his words, earn his assets.”
“So, like you said earlier, tell all and get it all or…”
“Not my words, but essentially yes. But there is another side to this. This will liberate you in other ways. You can keep holding the burden of your story, and it sounds like a remarkable story I must say, and that burden will continue to hold you down, oh, excuse me. What a horrible thing to say considering…I mean…what I am trying to say is that you will never be fully released by the things you have experienced.”
I considered the offer again as he paused.
“I must say, I would really love to hear your story. I know he has told me he loved the parts he knows, and just wants to be able to know your background to the fullest possible extent.”
“So the old perv wants to hear what? How I was taken so young? How I was conditioned to want sex all the time? How I was a whore? Or maybe how I screwed up my marriages?”
“I agree that his interest is suggestive and illuminates his unusual tendencies, but he and I theorize, that some of your personal burden over these events could be significantly eased and I submit that you could enjoy your life more fully.”
“If it doesn’t do any of that? Then what? You have a record of what a damaged freak I am? Why? So you can hold that over me?”
“Oh- no, not at all. Is that what is troubling you? Heaven’s no. He just wants to provide all he can for you, and we both think this would be a big step.”
I considered his point. “I don’t know why this is a big deal for him. I meet all the needs of our arrangement. I never asked for him to be a financial slave to me or to have this kind of control.”
I watched as Dr. Heard shifted in his leather chair and then looked at me with an expression that he knew what I was about to propose. Then he said, “If you are concerned about your privacy, I will assure you, in whatever way you wish, Lisa, that everything will remain completely confidential. No one will be able to learn your story unless you and he both concur. My record will be stored on a device that is encrypted and secure and will never go to the internet.
I stood up and stepped to the window and looked at the office plaza’s fountain below.
“Lisa, this story, what little I do know is amazing and should not be turned away from. I believe that there are others like you, those who experienced forbidden relations and grew to be so much more, and that your story is important.”
“No, Dr. Heard, you know so little, and you want to know if the good parts you know are the best parts. You want to see how far I have gone.”
“Well, I confess, yes I am curious, but you should see this as an opportunity to unburden you and to personally benefit. I am told that the benefactor plan is totally binding and that you receive an immediate transfer of assets upon completion of the whole story, an impressive deal. Should you survive him the entire estate, except for modest portions for his blood relatives, becomes yours. As I said, this is a very discreet arrangement the only you, him, and his attorney will ever know about.”
I felt a flash of excitement at the mention of the attorney. That had been a long day a few weeks ago. “I am not sure I remember every detail. How will I know if our session will be enough?”
“That is a difficult question. Once session will not be sufficient, if what I have heard is correct. He will listen to the record and ask me questions for any portions that require illumination.”
“What about the things that have crossed the line? Won’t that make you an accessory?”
“No, I am still bound by my oaths and I can tell you that any crimes you could have committed would never receive my notes. I doubt those participants even think of them as crimes, including yourself. Am I mistaken?
“No, I was sacred at first, but then enjoyed nearly everything.”
“Good. That is an important first step. Now, tell me, what other assurance can I give you that your secrets will remain safe?”
“Let me suck your dick while you record me. Give me the recording and we can proceed.”
I turned to face him to see his reaction. He blushed a little and shifted in his chair again before looking at me and saying, “Yes, well I expected something like that. Of course he let me know you would demand some insurance of this kind. He also, ah, convinced me to accept this departure from the practice. So, if that will allow us to proceed, then yes, you shall have you shall have your way.”
I smiled. I knew this would work. There was no way I would pass up this kind of offer. I exhaled and strutted over to him. “Is the device recording already?”
“Yes, of course Lisa.”
“Good. Before we start, describe me.”
Describe you? Yes, of course. You are Lisa Merchant. A client has been referred to me. You are 39 years old, look much younger, divorced twice, currently unmarried, no c***dren, and a resident of…well many places.”
I said, “Don’t worry about that. What do I look like?”
“You are beautiful. You are just over five and-a-half feet and weigh about a hundred and thirty-five pounds. You have auburn, no red, yes, a deep red-orange hair that passes your shoulders, but is up right now.”
“Good, remarkably good. Five foot six and holding at one-thirty-five. What am I wearing? Be detailed.”
“Aw, yes, ok, you are dressed in a cream silk blouse that is tight enough to see you have a white camisole on and a black bra underneath that. You have a dark grey, almost black tight skirt that stops above your knees and reveals that you are wearing a garter belt and stockings. You have high heels, high heels with, oh, about six-inch thin shiny stiletto heels. You wear your makeup dark around the eyes and have dark shiny lips. You have only two pieces of jewelry, a silver chain around your neck and another heavier chain around your right wrist. Good enough?”
I smiled and was impressed. “Excellent. Bonus question- what color is the garter belt?
“Well since the stockings are black your bra is obviously black, I can safely guess it too is black.”
“Excellent. And any thoughts on my panties?”
“Well, yes. You left them at home.”
I smiled wider. “Actually doctor, they are in the car. I always get wet in psychoanalyst offices. So, now lets get started.” I let that hang in mid-air for a moment.
I changed my smile to a more serious, yet mischievous grin and said, “Stand up and place your hands at your belt line and don’t move.”
Dr. Heard cleared his throat and stood with his hands on his hips.
I looked him in the eye and said, “So you want to know more about me. Let’s start here. I am going to suck your cock until you cum in my mouth and then I am going to swallow your load right after I show you your cum. I am going to do it all without my hands.”
I knelt and opened his pleated trousers and let them fall to the floor. I pulled his underwear away form his crotch and looked up him as I opened my mouth and let his semi rigid dick pass my lips to reach my throat. I licked it inside my mouth and then closed my lips around his shaft. In about ten or twelve suck-strokes I had him hard. I concentrated on his shaft and let my mouth caress his cockhead. In about four minutes I felt him tighten and heard his breathing become labored. He neared his orgasm and I began twisting my head around his cock and took him over the edge. I took my mouth away from his cock long enough to say- “are you going to cum in my mouth Dr. Heard?”
“Yes! Oh yes, you incredible woman!”
I leaned in and finished him off. His load covered my tongue. I withdrew and looked up at him. Before he looked down at me I took a finger and swabbed a small portion and wiped it inside my left bra cup and against my tit. When he peered down through his nearly shut eyes I showed him his cumload and then swallowed it, finishing off by licking my lips.”
A few minutes later he was dressed and sat in his chair. He looked at me and started to stand and stammered, “can I offer you a moment in the restroom, or a glass of water or anything?”
I smiled and coolly said, “No, I am used to the taste of an older man in my mouth…I kinda like it actually.”
“Uhm, ok, well given what I little I do know about your personal history, I guess that should not shock me. How about we start with an overview of your remarkable life? Is that ok?”
I looked out the window, and then at my shiny high heels and the floor. Then I made my decision and looked at him and said, “Ok, let’s begin.”
“The overview of my life is shocking to some, disgusting to some, and exhilarating to others…”
I grew up in the Los Angeles area. My mom was a nurse, and still is probably, and dad worked for a petroleum company as an engineer. His company is not important, but that he was associated with the oil industry is what led to him being gone so often and put me on this course. My virginity was taken early by a friend of my parents, after she fell asleep drunk. He fucked me instead of her after catching me watching them fucking several times while my dad was in Alaska for work. That man coerced me to become his private sex toy and then shared me with other dirty old men. Then he got me a job as a stripper, where I avoided d**gs, but enjoyed many things, including anal, group sex, and other women, but I was too young and they found out. Along the way my mom and dad split up because of her fucking around on him. Shortly after being fired from the strip club in a rather cruel way I became an escort for those who could afford such a rare age-related commodity. About a year later my mom found out about my escort profession and kicked me out having no real idea that I already had a nice place to live. When I completed school I had earned more than enough to pay for college and tried to deny my sexual needs and become a normal person. My second foray in a relationship ended with an initially non-consensual gangbang by a North Carolina university football specialty squad, yes lots of black men, and a realization that I loved and needed more sex than any one person could provide. I graduated early and went to work as a paralegal as I began work on my law degree. I tried to go straight again, but found myself escorting for the fun of it and picking up strangers on business trips. I completed a law degree, but made no attempt to pass the bar or become anything more than a legal advisor to a law firm and eventually became a manager within the firm, reporting only to the partners. I hated the job that much of the time, but kept working because it provided business travel which in turn allowed me to escort or causally date many strangers in different cities. In my late 20’s I met a nice guy and initially tried to become normal, but then learned that he wanted to be “a freak” with me. I then told him all that I had done – almost every detail. He asked to see me get fucked by a group of men and after he bugged me enough I set up a date with a single man instead. After I was fucked I had him go down on me and our relationship was forever changed. Over the next ten months he became a cuckhold and our marriage was ended. I left him and he became bisexual and then totally gay. I continued to work and escort occasionally. Then I was found out by one of the partners. After they quietly provided a very nice ‘promotion’ package I fucked the partners and was often hired as a special consultant to assist with matters that needed my expertise, such as new clients, assisting with divorce settlements, and protecting the firm in other ways. While I was on a retainer with the firm, I was also enjoying myself as an escort and began traveling. I met my second husband while he was a pilot on the LAX-Las Vegas route and began fucking him. I told him very little of sexual my past and we were married. He hung in there for several years, but we parted when he was home caring for his aging parents and re-kindled his teenage love. Of course my needs were such that I was screwing men and women the whole time we were married. He never suspected or found out. He often remarked at how talented I was and even confessed that he felt bad he couldn’t keep up. He tried hard, but knew he wasn’t up to totally satisfying me. That took me to the age of 35. I still looked great and began playing with a wide variety of guys and girls as a young ‘cougar’ or a MILF, or whatever their fantasy was. I became a dominatrix in my own right and continued to travel to see new clients and do naughty things. I also developed a personal love of cuckholding guys who were older than me.
“That is what led me to where I was when these ‘confession sessions’ are supposed to start.”
Dr. Heard lowered his glasses and rubbed his Freud-like thin beard and smiled. “That is an excellent start. Now, how would you like to proceed? Beginning to end? With the good parts? End to beginning? The choice is yours.”
I smiled and said, “Well, I know myself pretty well. Let’s start at the beginning, but understand that I will probably jump around a bit…So, I was a strawberry blonde, about 65 pounds and four feet tall when I caught my babysitter masturbating…”
Please send me feedback.
Prelude
I was still numb, tasted cum, and was still a bit fuzzy in the head. I could hardly believe I had just blown the cock of a top Las Vegas Psychologist in his office...during a session. A lot had happened and I was still trying to understand.
The psychologist, Dr. Heard, had been asked to both present the full offer from my ‘benefactor’, more of a sugar-daddy-cuckhold, and record the story of my life, a confession really. “You are making me tell everything that has happened to me? Why? Does this give him some perverse insight or closure? What if I refuse?”
“I am not making you do anything. If you refuse he will not hold to his benefactor agreement with you. You will remain his guest, if you like, but you will not, in his words, earn his assets.”
“So, like you said earlier, tell all and get it all or…”
“Not my words, but essentially yes. But there is another side to this. This will liberate you in other ways. You can keep holding the burden of your story, and it sounds like a remarkable story I must say, and that burden will continue to hold you down, oh, excuse me. What a horrible thing to say considering…I mean…what I am trying to say is that you will never be fully released by the things you have experienced.”
I considered the offer again as he paused.
“I must say, I would really love to hear your story. I know he has told me he loved the parts he knows, and just wants to be able to know your background to the fullest possible extent.”
“So the old perv wants to hear what? How I was taken so young? How I was conditioned to want sex all the time? How I was a whore? Or maybe how I screwed up my marriages?”
“I agree that his interest is suggestive and illuminates his unusual tendencies, but he and I theorize, that some of your personal burden over these events could be significantly eased and I submit that you could enjoy your life more fully.”
“If it doesn’t do any of that? Then what? You have a record of what a damaged freak I am? Why? So you can hold that over me?”
“Oh- no, not at all. Is that what is troubling you? Heaven’s no. He just wants to provide all he can for you, and we both think this would be a big step.”
I considered his point. “I don’t know why this is a big deal for him. I meet all the needs of our arrangement. I never asked for him to be a financial slave to me or to have this kind of control.”
I watched as Dr. Heard shifted in his leather chair and then looked at me with an expression that he knew what I was about to propose. Then he said, “If you are concerned about your privacy, I will assure you, in whatever way you wish, Lisa, that everything will remain completely confidential. No one will be able to learn your story unless you and he both concur. My record will be stored on a device that is encrypted and secure and will never go to the internet.
I stood up and stepped to the window and looked at the office plaza’s fountain below.
“Lisa, this story, what little I do know is amazing and should not be turned away from. I believe that there are others like you, those who experienced forbidden relations and grew to be so much more, and that your story is important.”
“No, Dr. Heard, you know so little, and you want to know if the good parts you know are the best parts. You want to see how far I have gone.”
“Well, I confess, yes I am curious, but you should see this as an opportunity to unburden you and to personally benefit. I am told that the benefactor plan is totally binding and that you receive an immediate transfer of assets upon completion of the whole story, an impressive deal. Should you survive him the entire estate, except for modest portions for his blood relatives, becomes yours. As I said, this is a very discreet arrangement the only you, him, and his attorney will ever know about.”
I felt a flash of excitement at the mention of the attorney. That had been a long day a few weeks ago. “I am not sure I remember every detail. How will I know if our session will be enough?”
“That is a difficult question. Once session will not be sufficient, if what I have heard is correct. He will listen to the record and ask me questions for any portions that require illumination.”
“What about the things that have crossed the line? Won’t that make you an accessory?”
“No, I am still bound by my oaths and I can tell you that any crimes you could have committed would never receive my notes. I doubt those participants even think of them as crimes, including yourself. Am I mistaken?
“No, I was sacred at first, but then enjoyed nearly everything.”
“Good. That is an important first step. Now, tell me, what other assurance can I give you that your secrets will remain safe?”
“Let me suck your dick while you record me. Give me the recording and we can proceed.”
I turned to face him to see his reaction. He blushed a little and shifted in his chair again before looking at me and saying, “Yes, well I expected something like that. Of course he let me know you would demand some insurance of this kind. He also, ah, convinced me to accept this departure from the practice. So, if that will allow us to proceed, then yes, you shall have you shall have your way.”
I smiled. I knew this would work. There was no way I would pass up this kind of offer. I exhaled and strutted over to him. “Is the device recording already?”
“Yes, of course Lisa.”
“Good. Before we start, describe me.”
Describe you? Yes, of course. You are Lisa Merchant. A client has been referred to me. You are 39 years old, look much younger, divorced twice, currently unmarried, no c***dren, and a resident of…well many places.”
I said, “Don’t worry about that. What do I look like?”
“You are beautiful. You are just over five and-a-half feet and weigh about a hundred and thirty-five pounds. You have auburn, no red, yes, a deep red-orange hair that passes your shoulders, but is up right now.”
“Good, remarkably good. Five foot six and holding at one-thirty-five. What am I wearing? Be detailed.”
“Aw, yes, ok, you are dressed in a cream silk blouse that is tight enough to see you have a white camisole on and a black bra underneath that. You have a dark grey, almost black tight skirt that stops above your knees and reveals that you are wearing a garter belt and stockings. You have high heels, high heels with, oh, about six-inch thin shiny stiletto heels. You wear your makeup dark around the eyes and have dark shiny lips. You have only two pieces of jewelry, a silver chain around your neck and another heavier chain around your right wrist. Good enough?”
I smiled and was impressed. “Excellent. Bonus question- what color is the garter belt?
“Well since the stockings are black your bra is obviously black, I can safely guess it too is black.”
“Excellent. And any thoughts on my panties?”
“Well, yes. You left them at home.”
I smiled wider. “Actually doctor, they are in the car. I always get wet in psychoanalyst offices. So, now lets get started.” I let that hang in mid-air for a moment.
I changed my smile to a more serious, yet mischievous grin and said, “Stand up and place your hands at your belt line and don’t move.”
Dr. Heard cleared his throat and stood with his hands on his hips.
I looked him in the eye and said, “So you want to know more about me. Let’s start here. I am going to suck your cock until you cum in my mouth and then I am going to swallow your load right after I show you your cum. I am going to do it all without my hands.”
I knelt and opened his pleated trousers and let them fall to the floor. I pulled his underwear away form his crotch and looked up him as I opened my mouth and let his semi rigid dick pass my lips to reach my throat. I licked it inside my mouth and then closed my lips around his shaft. In about ten or twelve suck-strokes I had him hard. I concentrated on his shaft and let my mouth caress his cockhead. In about four minutes I felt him tighten and heard his breathing become labored. He neared his orgasm and I began twisting my head around his cock and took him over the edge. I took my mouth away from his cock long enough to say- “are you going to cum in my mouth Dr. Heard?”
“Yes! Oh yes, you incredible woman!”
I leaned in and finished him off. His load covered my tongue. I withdrew and looked up at him. Before he looked down at me I took a finger and swabbed a small portion and wiped it inside my left bra cup and against my tit. When he peered down through his nearly shut eyes I showed him his cumload and then swallowed it, finishing off by licking my lips.”
A few minutes later he was dressed and sat in his chair. He looked at me and started to stand and stammered, “can I offer you a moment in the restroom, or a glass of water or anything?”
I smiled and coolly said, “No, I am used to the taste of an older man in my mouth…I kinda like it actually.”
“Uhm, ok, well given what I little I do know about your personal history, I guess that should not shock me. How about we start with an overview of your remarkable life? Is that ok?”
I looked out the window, and then at my shiny high heels and the floor. Then I made my decision and looked at him and said, “Ok, let’s begin.”
“The overview of my life is shocking to some, disgusting to some, and exhilarating to others…”
I grew up in the Los Angeles area. My mom was a nurse, and still is probably, and dad worked for a petroleum company as an engineer. His company is not important, but that he was associated with the oil industry is what led to him being gone so often and put me on this course. My virginity was taken early by a friend of my parents, after she fell asleep drunk. He fucked me instead of her after catching me watching them fucking several times while my dad was in Alaska for work. That man coerced me to become his private sex toy and then shared me with other dirty old men. Then he got me a job as a stripper, where I avoided d**gs, but enjoyed many things, including anal, group sex, and other women, but I was too young and they found out. Along the way my mom and dad split up because of her fucking around on him. Shortly after being fired from the strip club in a rather cruel way I became an escort for those who could afford such a rare age-related commodity. About a year later my mom found out about my escort profession and kicked me out having no real idea that I already had a nice place to live. When I completed school I had earned more than enough to pay for college and tried to deny my sexual needs and become a normal person. My second foray in a relationship ended with an initially non-consensual gangbang by a North Carolina university football specialty squad, yes lots of black men, and a realization that I loved and needed more sex than any one person could provide. I graduated early and went to work as a paralegal as I began work on my law degree. I tried to go straight again, but found myself escorting for the fun of it and picking up strangers on business trips. I completed a law degree, but made no attempt to pass the bar or become anything more than a legal advisor to a law firm and eventually became a manager within the firm, reporting only to the partners. I hated the job that much of the time, but kept working because it provided business travel which in turn allowed me to escort or causally date many strangers in different cities. In my late 20’s I met a nice guy and initially tried to become normal, but then learned that he wanted to be “a freak” with me. I then told him all that I had done – almost every detail. He asked to see me get fucked by a group of men and after he bugged me enough I set up a date with a single man instead. After I was fucked I had him go down on me and our relationship was forever changed. Over the next ten months he became a cuckhold and our marriage was ended. I left him and he became bisexual and then totally gay. I continued to work and escort occasionally. Then I was found out by one of the partners. After they quietly provided a very nice ‘promotion’ package I fucked the partners and was often hired as a special consultant to assist with matters that needed my expertise, such as new clients, assisting with divorce settlements, and protecting the firm in other ways. While I was on a retainer with the firm, I was also enjoying myself as an escort and began traveling. I met my second husband while he was a pilot on the LAX-Las Vegas route and began fucking him. I told him very little of sexual my past and we were married. He hung in there for several years, but we parted when he was home caring for his aging parents and re-kindled his teenage love. Of course my needs were such that I was screwing men and women the whole time we were married. He never suspected or found out. He often remarked at how talented I was and even confessed that he felt bad he couldn’t keep up. He tried hard, but knew he wasn’t up to totally satisfying me. That took me to the age of 35. I still looked great and began playing with a wide variety of guys and girls as a young ‘cougar’ or a MILF, or whatever their fantasy was. I became a dominatrix in my own right and continued to travel to see new clients and do naughty things. I also developed a personal love of cuckholding guys who were older than me.
“That is what led me to where I was when these ‘confession sessions’ are supposed to start.”
Dr. Heard lowered his glasses and rubbed his Freud-like thin beard and smiled. “That is an excellent start. Now, how would you like to proceed? Beginning to end? With the good parts? End to beginning? The choice is yours.”
I smiled and said, “Well, I know myself pretty well. Let’s start at the beginning, but understand that I will probably jump around a bit…So, I was a strawberry blonde, about 65 pounds and four feet tall when I caught my babysitter masturbating…”
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