Cuckold Sissy s First Meet Fantasy
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My Cuckold Fantasy Part Four free porn video
Part Four: The Next Step
After a few weeks of exploring the cuckold lifestyle my wife decided it was time to take the next step.
While I was working I received a text from her telling me she had a surprise waiting for me when I got home. This made the rest of the day drag by as I wondered and tried to guess what it might be.
When 5 o'clock hit I wasted no time getting home. When I walked in the door she was there waiting. I received instructions to go in the bathroom, take a bath and shave everything, legs, chest, arms and my face. Once I was done I dried off and walked into the bedroom. Laid out on the bed was a French maid dress, a chastity cage and a large strap-on dildo. As I was looking at all this she walked into the bedroom and told me to have a seat at her makeup vanity. She spent the next 30 minutes or so doing my makeup. I think we both a little amazed at the results. Next she did my finger nails and toes with a pretty bright pink nail polish, the I put on a garter belt and thigh highs. After I stepped into the dress and she zipped it up she gave me a pair of high heels. Lastly she put a wig cap on me followed by a long blond wig. I stepped back and admired myself in the mirror. Before I could say anything she said there was one more thing I needed to put on. In her hand was a chastity cage. As she locked it on my cock she explained to me that it would remain there unless she decided to remove it, and she would keep the keys.
I looked at the bed and the only thing left was the strap-on, she noticed me looking at it and picked it up and explained that this was for training me how to take a large cock in my ass. With that she put it on and grabbed some lube. Once it was lubed up she instructed me to get on the bed in the doggy style position then she applied more lube to my ass. She slowly worked in a finger, then another. As she applied yet more lube she worked her fingers around the ring of my sphincter getting it to relax more and more. After a few minutes I was ready for a third finger. I was now ready for the dildo. She slowly worked it into my ass until the whole thing was inside me. Then she grabbed my hips and started to fuck me. Slowly and deliberately at first. As it slid in and out of me the feeling of it pressing against my prostate was driving me crazy. She noticed that I was really enjoying it since I had started to back into it as she started each new thrust. She called me a little cock slut as she sped up driving the fake cock into me. I told her I was going to cum and with that she smacked me on the ass and explained that I better not. I was to ask for permission before I would be allowed to cum or the punishment would be severe.
I begged and pleaded with her that I be allowed to cum and she resumed fucking me. She informed me that I could cum but I was not allowed to touch my cock or the cage. A few minutes later and I could feel the orgasm hit. My legs where shaking as it started to wash over me. My limp dick began to twitch as cum started dripping from the cage. It was more intense than any orgasm I have ever felt before. I thanked her for allowing me to cum and she said I was welcome but now I had to clean up the mess and draw her a bath.
I did as she said. While she was in the tub she explained that she had a date with one of her regular friends and they would be going out without me. She said there was a list of chores on the refrigerator and if I had them done to her satisfaction she would have a reward for me when she returned. As she continued to get ready I went to the kitchen to have a look at the list. It was a list of cleaning chores to busy me while she was out.
Just then the doorbell rang. I walked to the door, answered it and invited him in. Once inside he looked at me and told me I looked very pretty. He asked me if my wife was ready and I told him she would be out in a few minutes. He accepted my offer to make him a drink in the mean time. As he was finishing up his drink she walked into the room. She looked amazing in her little black dress and high heels. She walked over to me and told me she expected to see the list completed when she got home then she walked over to him and gave him a big kiss. She looked back and said she would be back in a few hours and I better get busy. With that they were out the door.
I busied myself completing the chores one by one. Just as I sat down after finishing the last one I heard a car pull up and a door close. I got up to greet them at the door and was a little surprised she was alone when she came in. I asked her if they had a good time and she smiled and said they had a great time. She looked around to see if I had completed the list, seeing that I had she complemented me and asked if I was ready for my reward. I explained that I was and she told me to go and lay down on our bed and wait for her.
As she walked in the room she stepped out of her dress and pulled down her panties. Once she took them off she put them over my face. They were wet with both of their juices mixed together. She rubbed them all over my face and asked me if I liked it, I smiled and said I did. Next she took the panties and dropped them on the floor as she climbed up on the bed straddling me. As she started to ride my face I cleaned the cum from her pussy, I don't know who loved it more. As she rode my face to orgasm I took all she had to give me. Once she came she got up and gave me a kiss and told me she loved me and asked if I was ready for my reward? I said I thought this was the reward. She laughed and said no that cleaning her pussy is my job. My reward would be here in a few minutes. Then she said we should get me ready for it. With that she got out the lube and applied some to her fingers and my hole. I was in heaven as she slowly worked her fingers in and out. Just then I heard the doorbell ring again as was instructed to remain in this position until she returned. I heard her open the door and I heard a mans voice. After a few minutes I heard them walk into the room and my wife explain to him that I was the sissy she had been telling him about. He said that I looked like I was ready to take his cock. Just then I felt the tip of it push against my hole. As he started to push his cock into me I pushed back against it taking the whole thing. It felt amazing as he started to fuck my ass. I was taken to a whole new place and began to moan with delight as his cock pushed against my prostate over and over. My wife moved around and laid down in front of me looking me in the eyes and asked if I was enjoying her reward. The look on my face gave her the answer and she leaned in and kissed me. Just then he announced that he was about to cum as he quickened his pace. Then I felt his cock start to throb and he pushed it all the way in, I could feel his cum shooting inside me, at the same time I was cumming as well. Once he pulled out I collapsed on the bed dizzy from what I had just experienced. My wife got up and saw him out and returned to the bedroom. I thanked her for the reward and told her how amazing it felt. She asked if I liked being her sissy maid. I told her it was a dream come true. She said good because she wanted to see me dressed and ready to serve whenever I wasn't at work.
I got up to clean up and remove my makeup before bed while she explained what all would be expected from me from now on. Then she gave me a nightgown to wear to bed. As I drifted off to sleep I couldn't help but reflect on the recent events and where it has taken us. I wouldn't change a thing.
After a few weeks of exploring the cuckold lifestyle my wife decided it was time to take the next step.
While I was working I received a text from her telling me she had a surprise waiting for me when I got home. This made the rest of the day drag by as I wondered and tried to guess what it might be.
When 5 o'clock hit I wasted no time getting home. When I walked in the door she was there waiting. I received instructions to go in the bathroom, take a bath and shave everything, legs, chest, arms and my face. Once I was done I dried off and walked into the bedroom. Laid out on the bed was a French maid dress, a chastity cage and a large strap-on dildo. As I was looking at all this she walked into the bedroom and told me to have a seat at her makeup vanity. She spent the next 30 minutes or so doing my makeup. I think we both a little amazed at the results. Next she did my finger nails and toes with a pretty bright pink nail polish, the I put on a garter belt and thigh highs. After I stepped into the dress and she zipped it up she gave me a pair of high heels. Lastly she put a wig cap on me followed by a long blond wig. I stepped back and admired myself in the mirror. Before I could say anything she said there was one more thing I needed to put on. In her hand was a chastity cage. As she locked it on my cock she explained to me that it would remain there unless she decided to remove it, and she would keep the keys.
I looked at the bed and the only thing left was the strap-on, she noticed me looking at it and picked it up and explained that this was for training me how to take a large cock in my ass. With that she put it on and grabbed some lube. Once it was lubed up she instructed me to get on the bed in the doggy style position then she applied more lube to my ass. She slowly worked in a finger, then another. As she applied yet more lube she worked her fingers around the ring of my sphincter getting it to relax more and more. After a few minutes I was ready for a third finger. I was now ready for the dildo. She slowly worked it into my ass until the whole thing was inside me. Then she grabbed my hips and started to fuck me. Slowly and deliberately at first. As it slid in and out of me the feeling of it pressing against my prostate was driving me crazy. She noticed that I was really enjoying it since I had started to back into it as she started each new thrust. She called me a little cock slut as she sped up driving the fake cock into me. I told her I was going to cum and with that she smacked me on the ass and explained that I better not. I was to ask for permission before I would be allowed to cum or the punishment would be severe.
I begged and pleaded with her that I be allowed to cum and she resumed fucking me. She informed me that I could cum but I was not allowed to touch my cock or the cage. A few minutes later and I could feel the orgasm hit. My legs where shaking as it started to wash over me. My limp dick began to twitch as cum started dripping from the cage. It was more intense than any orgasm I have ever felt before. I thanked her for allowing me to cum and she said I was welcome but now I had to clean up the mess and draw her a bath.
I did as she said. While she was in the tub she explained that she had a date with one of her regular friends and they would be going out without me. She said there was a list of chores on the refrigerator and if I had them done to her satisfaction she would have a reward for me when she returned. As she continued to get ready I went to the kitchen to have a look at the list. It was a list of cleaning chores to busy me while she was out.
Just then the doorbell rang. I walked to the door, answered it and invited him in. Once inside he looked at me and told me I looked very pretty. He asked me if my wife was ready and I told him she would be out in a few minutes. He accepted my offer to make him a drink in the mean time. As he was finishing up his drink she walked into the room. She looked amazing in her little black dress and high heels. She walked over to me and told me she expected to see the list completed when she got home then she walked over to him and gave him a big kiss. She looked back and said she would be back in a few hours and I better get busy. With that they were out the door.
I busied myself completing the chores one by one. Just as I sat down after finishing the last one I heard a car pull up and a door close. I got up to greet them at the door and was a little surprised she was alone when she came in. I asked her if they had a good time and she smiled and said they had a great time. She looked around to see if I had completed the list, seeing that I had she complemented me and asked if I was ready for my reward. I explained that I was and she told me to go and lay down on our bed and wait for her.
As she walked in the room she stepped out of her dress and pulled down her panties. Once she took them off she put them over my face. They were wet with both of their juices mixed together. She rubbed them all over my face and asked me if I liked it, I smiled and said I did. Next she took the panties and dropped them on the floor as she climbed up on the bed straddling me. As she started to ride my face I cleaned the cum from her pussy, I don't know who loved it more. As she rode my face to orgasm I took all she had to give me. Once she came she got up and gave me a kiss and told me she loved me and asked if I was ready for my reward? I said I thought this was the reward. She laughed and said no that cleaning her pussy is my job. My reward would be here in a few minutes. Then she said we should get me ready for it. With that she got out the lube and applied some to her fingers and my hole. I was in heaven as she slowly worked her fingers in and out. Just then I heard the doorbell ring again as was instructed to remain in this position until she returned. I heard her open the door and I heard a mans voice. After a few minutes I heard them walk into the room and my wife explain to him that I was the sissy she had been telling him about. He said that I looked like I was ready to take his cock. Just then I felt the tip of it push against my hole. As he started to push his cock into me I pushed back against it taking the whole thing. It felt amazing as he started to fuck my ass. I was taken to a whole new place and began to moan with delight as his cock pushed against my prostate over and over. My wife moved around and laid down in front of me looking me in the eyes and asked if I was enjoying her reward. The look on my face gave her the answer and she leaned in and kissed me. Just then he announced that he was about to cum as he quickened his pace. Then I felt his cock start to throb and he pushed it all the way in, I could feel his cum shooting inside me, at the same time I was cumming as well. Once he pulled out I collapsed on the bed dizzy from what I had just experienced. My wife got up and saw him out and returned to the bedroom. I thanked her for the reward and told her how amazing it felt. She asked if I liked being her sissy maid. I told her it was a dream come true. She said good because she wanted to see me dressed and ready to serve whenever I wasn't at work.
I got up to clean up and remove my makeup before bed while she explained what all would be expected from me from now on. Then she gave me a nightgown to wear to bed. As I drifted off to sleep I couldn't help but reflect on the recent events and where it has taken us. I wouldn't change a thing.
Libbie
- 25.12.2022
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