The Therapist Chapter 1 Sophie
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Miss Sophie, The Sissy Maker free porn video
I woke up on Sunday and I toke a coffee in my living room. I then remembered a past part of my life, 15 years ago.
I was 24. I had just finished my university and was freshly a worker. I had broken up with my GF 4 months ago so I was single, and I wanted it to keep it that way. I have been in couple since high school, so I wanted to enjoy a little bit of freedom.
One night, I was surfing on dating forums. And I saw Miss Sophie post. My life changed that night. Miss Sophie was a lady of 41 years old. She was looking for young men like me for special adventure. There was not a lot of description but it was enough to enlighten my curiosity.
I started to chat with her. We chatted together around 2 weeks. She wanted to meet me. To be honest, I always had that fantasy of an older woman. So I did accept her offer. She gave me her address and I met her at her house. I remember when I parked my car in front of her house. God, I was so nervous and excited in the same time. I knocked at her door. 10 seconds, an eternity to me, must have passed before she opened the door. When I first saw her, I could not believe that she was 41. She was so beautiful. Yes, Miss Sophie was a gorgeous woman. She invited me inside with a smile that I will always remember.
You are reading this and I know what you are thinking. It is another cougar story. Well, you are wrong. If only it was only that ….
We went in the living room. At first, I didn’t realize what I saw in the living room. I was just thinking that we would have sex. On the coffee table, they were different sexy kit, stockings, wigs, etc. Yes, it was a large coffee table. She asked me how my sexual life was so far. I told her nothing much. I was with the same girl since high school. She then explains me what was the special adventure that she was proposing on her post. She asked me if I knew what sissification meant. I told her that I didn’t know, which was true. Miss Sophie told me that she had that fantasy of her, to transform young boy into beautiful girly girl. I started to laugh because I thought it was a joke. She told me to wait 2 mins. She came back with a red binder that she gave to me. She asked to open it and to tell her what I was seeing. I opened the binder to find nothing special but girls in sexy dressing. Some were actually really cute ! So I asked her what I was seeing. Her answer makes me silent for the next minute. She told me that all those girls where actually boys that she transformed. I could not believe it. She said that her fantasy was to do sissification and then have some fun with those sissy, as she called them. I told her that I was not that kind of guy and I politely told her that I was leaving. She said that there was no problem and I that I would change my idea. I told her that I was pretty much sure of my decision.
Two weeks later, I could not stop thinking about that night. Miss Sophie was right. I contacted her again and we met again at her house. I told her that I was willing to try but I was nervous. She told me that it was normal and to relax. She told me that they were many step to achieve the transformation.
She asked me if I had already wearied girl panties. I told her no. She gave me 7 freshly new pink thongs. She told me I had to wear one each day during 1 week. The first day and the second one was weird. I was at my office and I thought that everybody knew what I was wearing. The other 5 days were actually good. I came back 1 week later with my task done. She was happy. Step 2 was the full dressing at her house. I chose a kit, a wig and she even put me makeup, eyeliner, gloss. I was looking like a girl. She told me that I was beautiful. I looked in the mirror and it was true, I was feeling beautiful. She said that because I had done step 2, I would have a present next week. She told me that I could leave with the cloth and the wig, so I could were them at home if I wanted… which I did 3 nights.
1 week had passed and I was excited to get my present. We sat on the sofa and I opened the present. I didn’t know what if was. She told me it was a chastity cage. She said that it was to lock my penis, preventing me to get hard, because sissy don’t get hard. She then explained me some term. She told me that the penis was the sissy clitoris and the ass was the sissy pussy. She called it ass-pussy. She proposed me to install it on me. I agreed. It was nice that a girl touch my penis for the first time since long time and the purpose of it was to cage me. The sensation was strange but exciting. She had the key on her neckless. There were other keys on it. I asked her why she had more keys to that neckless. She said that she had some sissy out there caged. She told me that I would have to keep it 1 week and that was step 3.
1 Week later, I went back at Miss Sophie house. Each time I was seeing her, she was more beautiful. She unlocked me and asked me to take and shower and then dress like last time. Once done, i put some makeup by myself and I was now looking like a girl, once again. I came back and she unlocked me once again She asked how I was feeling now. I told her that I was getting comfortable with it each time. She asked me if I was ready to do step 4. I said yes. She told me that tomorrow, I and she would go shopping at victory secret a new kit for me. But, I would have to do it dress up like a girl. And I needed to find a girl name. I chose Kendra.
We came back from shopping and everything went good. People actually believe I was a girl. I have a soft voice. I put on my new lingerie. Miss Sophie did the same and she was so dam sexy. I was just thinking to fuck her already, but I was caged. We went in the living room and she asked me if I knew what was a sissygasm. I said no. She then explained me that men had a G spot like women. And that G spot is their prostate. And to stimulate the prostate, I was done anally. She told me that a man could came without any stimulation to the penis. She told me that in some case, it happens that during the process, very small quantity of semen flows continually, from the penis. The same way as a woman vagina gets wetter during sex. She said that Step5 was to be fucked by her with a strapon, caged and dress up. I told her that it would hurt. My ass , I mean my ass-pussy was virgin after all. She said she had experience and everything would be fine. She told me to lay down and pull my legs up. She started to gently massage my anus with her finger and lube. It fell so good. It was new sensation for me. I wanted to get hard but the cage was forcing me to not. I then fell something so good. She was using her tongue. I could feel that something she was introducing just a little bit her tongue in my ass. She ate my ass for 20 mins before telling me that I was ready. She asked me to get on four and to not move and be submissive and follow her lead. She put the strap on on and when in front of me, she asked me to suck it. I was surprise that I could take it deep before gagging. I must admit it, it was exciting. I was exciting because it was Miss Sophie. After 10 mins of blowing her, she went behind me and she told me to relay and be ready to before a sissy. She put the tip on my anus and softly started to trust inside. I think that I was so relaxed and excited that I didn’t get any pain. I could feel every centimeter until it was all inside. She then started to move her hips and fuck me, like the sissy I was. I must admit, the doggystyle position is really good when you give it but also really good when you received it. During the fuck, I was curious and I looked at my penis. I could see a little of semen flowing out like Miss Sophie told me. And then, I felt it. I cannot describe it but it was like the sensation you have when you come, but ten times it. I then saw huge loads of cum dripping on the floor. I never came so much. Step 5 was done.
During the next month, she fucked me 4-5 times a week, always at her home. I was loving her, getting attach, even if I had never penetrated her. She was the one penetrating me and I was loving it! Sometimes, she was unlocking me and I was wearing a condom during the fuck so all the cum was gathered. And I was drinking it at the end. During that month, she gave me another present. It was plastic boobs so I can simulate a breast.
One evening, she asked me if I wanted to be a real sissy. I told her that I was one. She said that I was indeed a sissy but not a real one. To become a real sissy, you must taste and receive an alpha male dick. I told her that was way above me. It was something to get fucked in the ass with a strapon but at least it was a girl. But to suck and be fuck by a man was not in my interest, even after at I have done already. I rejected her idea and said that I, as a man, would not sleep with a man. She told me that I was not a man anymore but a sissy named Kendra. I told her that if she was letting me fuck her, she would know how manly I was. I then left and she did not contact each other for 3 months.
I then received an email from her. She asked me to come at her place and show her my alpha side. I knocked at her door, and she yelled that it was unlocked. I found her in her bedroom, with black stockings. She didn’t lose a minute and asked me to fuck her throat. Which I did. Generously. And after 10 mins of throat fucking, she went in doggystyle and asked me to directly fuck her ass. Only her ass. I put my condom and lubed it. I directly went all deep. She moaned. She was so wet that I could see her juice flows down her inner tight. I fucked her ass for at least 30 minutes before I pull out and come in her thoat. She told me that I was way better at an alpha then a sissy. She gave me again the red binder, the one with all her active sissies. She told me that she needed a man to make the final step to some and just fucks occasionally other real sissies. I was not comfortable to have sex with a man, but they were not man anymore, they were sissies. And I was going to fuck them all.
I was 24. I had just finished my university and was freshly a worker. I had broken up with my GF 4 months ago so I was single, and I wanted it to keep it that way. I have been in couple since high school, so I wanted to enjoy a little bit of freedom.
One night, I was surfing on dating forums. And I saw Miss Sophie post. My life changed that night. Miss Sophie was a lady of 41 years old. She was looking for young men like me for special adventure. There was not a lot of description but it was enough to enlighten my curiosity.
I started to chat with her. We chatted together around 2 weeks. She wanted to meet me. To be honest, I always had that fantasy of an older woman. So I did accept her offer. She gave me her address and I met her at her house. I remember when I parked my car in front of her house. God, I was so nervous and excited in the same time. I knocked at her door. 10 seconds, an eternity to me, must have passed before she opened the door. When I first saw her, I could not believe that she was 41. She was so beautiful. Yes, Miss Sophie was a gorgeous woman. She invited me inside with a smile that I will always remember.
You are reading this and I know what you are thinking. It is another cougar story. Well, you are wrong. If only it was only that ….
We went in the living room. At first, I didn’t realize what I saw in the living room. I was just thinking that we would have sex. On the coffee table, they were different sexy kit, stockings, wigs, etc. Yes, it was a large coffee table. She asked me how my sexual life was so far. I told her nothing much. I was with the same girl since high school. She then explains me what was the special adventure that she was proposing on her post. She asked me if I knew what sissification meant. I told her that I didn’t know, which was true. Miss Sophie told me that she had that fantasy of her, to transform young boy into beautiful girly girl. I started to laugh because I thought it was a joke. She told me to wait 2 mins. She came back with a red binder that she gave to me. She asked to open it and to tell her what I was seeing. I opened the binder to find nothing special but girls in sexy dressing. Some were actually really cute ! So I asked her what I was seeing. Her answer makes me silent for the next minute. She told me that all those girls where actually boys that she transformed. I could not believe it. She said that her fantasy was to do sissification and then have some fun with those sissy, as she called them. I told her that I was not that kind of guy and I politely told her that I was leaving. She said that there was no problem and I that I would change my idea. I told her that I was pretty much sure of my decision.
Two weeks later, I could not stop thinking about that night. Miss Sophie was right. I contacted her again and we met again at her house. I told her that I was willing to try but I was nervous. She told me that it was normal and to relax. She told me that they were many step to achieve the transformation.
She asked me if I had already wearied girl panties. I told her no. She gave me 7 freshly new pink thongs. She told me I had to wear one each day during 1 week. The first day and the second one was weird. I was at my office and I thought that everybody knew what I was wearing. The other 5 days were actually good. I came back 1 week later with my task done. She was happy. Step 2 was the full dressing at her house. I chose a kit, a wig and she even put me makeup, eyeliner, gloss. I was looking like a girl. She told me that I was beautiful. I looked in the mirror and it was true, I was feeling beautiful. She said that because I had done step 2, I would have a present next week. She told me that I could leave with the cloth and the wig, so I could were them at home if I wanted… which I did 3 nights.
1 week had passed and I was excited to get my present. We sat on the sofa and I opened the present. I didn’t know what if was. She told me it was a chastity cage. She said that it was to lock my penis, preventing me to get hard, because sissy don’t get hard. She then explained me some term. She told me that the penis was the sissy clitoris and the ass was the sissy pussy. She called it ass-pussy. She proposed me to install it on me. I agreed. It was nice that a girl touch my penis for the first time since long time and the purpose of it was to cage me. The sensation was strange but exciting. She had the key on her neckless. There were other keys on it. I asked her why she had more keys to that neckless. She said that she had some sissy out there caged. She told me that I would have to keep it 1 week and that was step 3.
1 Week later, I went back at Miss Sophie house. Each time I was seeing her, she was more beautiful. She unlocked me and asked me to take and shower and then dress like last time. Once done, i put some makeup by myself and I was now looking like a girl, once again. I came back and she unlocked me once again She asked how I was feeling now. I told her that I was getting comfortable with it each time. She asked me if I was ready to do step 4. I said yes. She told me that tomorrow, I and she would go shopping at victory secret a new kit for me. But, I would have to do it dress up like a girl. And I needed to find a girl name. I chose Kendra.
We came back from shopping and everything went good. People actually believe I was a girl. I have a soft voice. I put on my new lingerie. Miss Sophie did the same and she was so dam sexy. I was just thinking to fuck her already, but I was caged. We went in the living room and she asked me if I knew what was a sissygasm. I said no. She then explained me that men had a G spot like women. And that G spot is their prostate. And to stimulate the prostate, I was done anally. She told me that a man could came without any stimulation to the penis. She told me that in some case, it happens that during the process, very small quantity of semen flows continually, from the penis. The same way as a woman vagina gets wetter during sex. She said that Step5 was to be fucked by her with a strapon, caged and dress up. I told her that it would hurt. My ass , I mean my ass-pussy was virgin after all. She said she had experience and everything would be fine. She told me to lay down and pull my legs up. She started to gently massage my anus with her finger and lube. It fell so good. It was new sensation for me. I wanted to get hard but the cage was forcing me to not. I then fell something so good. She was using her tongue. I could feel that something she was introducing just a little bit her tongue in my ass. She ate my ass for 20 mins before telling me that I was ready. She asked me to get on four and to not move and be submissive and follow her lead. She put the strap on on and when in front of me, she asked me to suck it. I was surprise that I could take it deep before gagging. I must admit it, it was exciting. I was exciting because it was Miss Sophie. After 10 mins of blowing her, she went behind me and she told me to relay and be ready to before a sissy. She put the tip on my anus and softly started to trust inside. I think that I was so relaxed and excited that I didn’t get any pain. I could feel every centimeter until it was all inside. She then started to move her hips and fuck me, like the sissy I was. I must admit, the doggystyle position is really good when you give it but also really good when you received it. During the fuck, I was curious and I looked at my penis. I could see a little of semen flowing out like Miss Sophie told me. And then, I felt it. I cannot describe it but it was like the sensation you have when you come, but ten times it. I then saw huge loads of cum dripping on the floor. I never came so much. Step 5 was done.
During the next month, she fucked me 4-5 times a week, always at her home. I was loving her, getting attach, even if I had never penetrated her. She was the one penetrating me and I was loving it! Sometimes, she was unlocking me and I was wearing a condom during the fuck so all the cum was gathered. And I was drinking it at the end. During that month, she gave me another present. It was plastic boobs so I can simulate a breast.
One evening, she asked me if I wanted to be a real sissy. I told her that I was one. She said that I was indeed a sissy but not a real one. To become a real sissy, you must taste and receive an alpha male dick. I told her that was way above me. It was something to get fucked in the ass with a strapon but at least it was a girl. But to suck and be fuck by a man was not in my interest, even after at I have done already. I rejected her idea and said that I, as a man, would not sleep with a man. She told me that I was not a man anymore but a sissy named Kendra. I told her that if she was letting me fuck her, she would know how manly I was. I then left and she did not contact each other for 3 months.
I then received an email from her. She asked me to come at her place and show her my alpha side. I knocked at her door, and she yelled that it was unlocked. I found her in her bedroom, with black stockings. She didn’t lose a minute and asked me to fuck her throat. Which I did. Generously. And after 10 mins of throat fucking, she went in doggystyle and asked me to directly fuck her ass. Only her ass. I put my condom and lubed it. I directly went all deep. She moaned. She was so wet that I could see her juice flows down her inner tight. I fucked her ass for at least 30 minutes before I pull out and come in her thoat. She told me that I was way better at an alpha then a sissy. She gave me again the red binder, the one with all her active sissies. She told me that she needed a man to make the final step to some and just fucks occasionally other real sissies. I was not comfortable to have sex with a man, but they were not man anymore, they were sissies. And I was going to fuck them all.
Charlize
- 02.06.2021
- 23
- 0
