Cuckold from Day One - Part 3



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Please read Part 1 here


Not long after Emily accepted me as her cuckold, I moved in with her permanently. She had a large house a little out of town, on a hill, with several acres around her to give her privacy. The house had a large beautiful pool and a great view. Emily occasionally hosted a swinger party at her house with several couples spending the weekend naked and enjoying good food, good drink and lots of kinky uninhibited sex. But that is a story for another time.

Before meeting Emily, I had retired early with plenty of money of my own. With Emily working and me having plenty of time on my hands, I took over the responsibility for cleaning and maintaining the house, as well as doing all the cooking. I spent all my time at her house naked. Emily had gone through my clothes and thrown out all but a few outfits that I used when we went out or when I did the shopping.

The problem with my being naked all the time was that I had a somewhat hairy body and Emily did not like that. While I was shaving her about every other day to keep her smooth all over, she was not about to shave me. She finally decided that we would both have laser hair removal treatments to permanently get rid of all our hair. It took many treatments over several months, but soon our bodies were both completely hairless and smooth all over.

In the beginning, Emily only had me in chastity when her young boys came over to fuck her, usually every night when she came home from work, and at various times each weekend. When they left, she would take me out and let me slide my cock into her stretched-out, cum-filled pussy. It was the best feeling I had ever experienced, and I was in heaven every time. We soon realized, however, that, at my age, I didn't have the stamina to fuck her every day. She soon determined that I would not get to fuck her most nights but would still take me out of the chastity before bed. She loved letting me cuddle and spoon with her naked. When she did let me fuck her, a couple of times a week, the waiting and anticipation allowed me to perform more up to her expectations.

One night, Emily had two of her boyfriends over at the same time. It was the first time I saw her with two men in a threesome. As I watched silently from my chair in the corner, these young men ravished her for a couple of hours. They took turns fucking her while she sucked the other one. They fucked her in all her holes and came several times. They would stop occasionally to allow me to lick the cum off her body and suck it from her pussy and ass. As a final act they double penetrated her, one in her pussy and one in her ass. Since they had both cum multiple times, it took quite a while for them to orgasm one last time. After they left, she let me know that she was too sore and exhausted for me that night. She did take the chastity cage off before we climbed in bed and we cuddled like usual as she fell quickly asleep.

In the middle of the night Emily woke me up yelling at me. Apparently, during the night as we were spooning, my cock had hardened and woke her up as it bumped into her ass. She was furious that I would wake her up to fuck her when she had made it very clear she didn't want me that night. I tried to explain that it wasn't on purpose, it had just happened, but she retrieved the cage and locked it onto my cock. She said that from then on, if I wanted to sleep with her, I had to have the cage on every night, all night long. I quickly agreed to calm her down and end the argument.

Emily would still let me out of the cage when she left for work in the morning. One day I found myself with the dinner cooking and the house spotless. With nothing to do, I opened my laptop and started reading some cuckold stories. Soon my cock was hard, and I started slowly pumping it as I read. Suddenly, with a start, I heard Emily screaming at me. She had come home early and caught me masturbating. She continued yelling at me, accusing me of masturbating every day and saying that's why I couldn't perform with her when she wanted. At the same time, she went to the bedroom, gathered up my meager wardrobe and threw it by the front door screaming, "Leave now. You have betrayed me, and you don't deserve to be here."

I was on my knees, crying and begging her to forgive me. I explained that it was the only time it had happened. I begged again and said I would do anything to stay. With that she started to calm down. I saw her thinking and then she explained that if I wanted to stay, I would have to be in chastity full-time from then on. I would only be allowed out when she allowed it, maybe once a week for a quick jerk to cum on her tits, and that for punishment, I would not be allowed to fuck her for at least 6 months, maybe longer. The thought of being in chastity forever sent a chill to my very core, but I could not envision my life without her, and I thought she might reconsider when she had calmed down, so I agreed. She pulled from a drawer a new chastity cage and locked me in it. Unlike the one I had been wearing with metal bars, this was a solid stainless-steel tube and it was a little too small for me so that unless I was very soft it was uncomfortable. It pointed my cock down between my balls and completely covered my shaft and head. Emily had effectively cut me off from stimulating my cock. With that, Emily instructed me to put my clothes away and join her in the shower because Chuck, one of her boys, was coming in a few minutes and that she really, really needed to be fucked.

As we cuddled in bed that night, she could see that I had been crying. She hugged me close and said that I should not worry, that I would soon get used to being in chastity full-time. She then said that seeing me in my new cage was getting her turned on. She opened her legs, pulled me to her and told me to eat her pussy. She said I needed to make her cum really good or I might not get out to jack off for a month or so. I ate her with a gusto I seldom expressed and made her cum several times. She seemed to be satisfied.

It was 10 days before she let me out for 10 minutes to cum on her tits. With the long delay I came in about 2 minutes and squirted more cum on her tits that I ever had before. After I had licked it all up, she commented that she liked my new large load and that maybe once every 2 weeks would be enough to keep my pipes clean. As we cuddled that night in bed, I felt a love and devotion to her that I can't explain.

Emily: I never told Jerry about the secret security cameras I had installed in the house when I built it. I often checked on him as he cooked and cleaned to make sure he was not secretly playing with himself. When I saw him, by chance one day, open his laptop and start to jack off, I immediately told my staff I had an emergency at home and left. I used all my acting ability to convince him I was furious and wanted him gone. It was my dream to have Jerry in chastity full time. When he quickly agreed to it so that he could stay, I felt an orgasm flow through my body. It was a huge rush to realize that Jerry would give me complete power over his sexual pleasure. I loved teasing and torturing him by denying his orgasms. The power he had given me over him was exhilarating and erotic for me. Sex with my boys even became more pleasurable. When I felt an orgasm coming on, I would look at Jerry, sitting silently in the corner, watching and knowing he would not have any orgasms in the foreseeable future and might never feel his cock inside me again. These thoughts increased the intensity of my orgasms greatly.

I printed out a revised list of rules and had Jerry sign the list as a sex-slave contract. He did not resist at all and seemed very happy to agree to the simplified, but more restrictive rules than those he originally agreed to. Here is the revised list of rules.

Rule #1: I will be immediately obedient to Emily at all times and will always refer to her as "Mistress" (i.e., "Yes, Mistress., "Thank you, Mistress.),
Rule #2: My cock will be in chastity unless Mistress decides to let me out.
Rule #3: I will be completely naked unless Mistress allows me to wear clothes in public.
Rule #4: I will be completely silent unless Mistress gives me permission to talk.

I decided to let Jerry out of chastity to cum on me about once every 2 weeks. He would count down the days and hours every time. When I let him out, he would spring to totally hard almost immediately. He would be so worked up from the anticipation that he would usually cum very quickly. I never touched him, just watched as he stroked his cock a few times before he came. His cum loads were also much bigger. Even though I would tell him he had 10 minutes to cum on me, he was generally back in the tube and licking my pussy in 5 minutes or less.


Soon after Emily had put me in permanent chastity, she told me a new boy would be coming over that night. Our preparation routine at the time consisted first of cleaning both of us inside and out. She said that if she was going to get a deep cleaning enema, I was too. Next, we got in the shower, where I washed her everywhere while she gave me instructions and talked about how horny she was. Next, I would use the soapy foam brush to clean inside her pussy and ass. Again, she insisted that if she got the foam brush up her ass, so did I. Finally, I would dry her off, do her hair and apply her makeup. I had been sufficiently trained and became quite expert at it. If we had time after preparing her, I would be allowed to eat her pussy until her boyfriend showed up.

We heard the knock on the door, and I went to my chair in the corner while Emily went to get him. When she led him into the bedroom, dragging him by his cock, I quickly recognized him as the 17-year old swimming sensation that went to the local high school. He was expected to lead the USA swimming team in the up-coming Olympics. He had a swimmer's body, with broad shoulders, a narrow waste and powerful, muscular legs. His body was completely hairless. He also had a long, thin cock.

Emily waived me over so that Jeff could get a good look at my hairless body. Jeff rubbed his hands over my body in various places, which made me feel a little uncomfortable, but it also felt good. He said that he agreed with her that the laser hair removal was a good idea, that currently the swim team got together a few times a week to shave each other all over, but that it usually turned into a suck and fuck fest, making the process take hours. They both got a laugh out of that. Emily explained that since his 18th birthday was the day before it was time that he experienced a woman's body for the first time. From the look of his cock which was hard as a rock as she slowly pumped it, he agreed with her. His cock very long with a nice mushroom head, but it was only as thick as an average cock. There was a ring protruding from the head through a Prince Albert piercing, which made it look even longer.

I was staring at Jeff's cock with a quizzical look on my face, which Emily noticed. She said that if I had a question, I could ask it. I thanked my Mistress then told Jeff that I had watched him swim on TV with only a small swimsuit and wondered how he hid that huge cock. He lifted his balls and showed me another ring. He explained that during a meet he would connect the Prince Albert ring to the small one under his balls. Connecting the rings pulled his cock down out of sight and prevented him from getting hard during a meet while looking at all the other sexy guys in their speedos.

Emily said she didn't want the Prince Albert ring in when they fucked and to have me remove it. He explained how to do it while I was fondling the head of his cock to get it out. Once out he wasted no time in laying Emily on the bed and inserting his cock all the way into her. She moaned, in what I interpreted as extreme pleasure, and said I could kneel by the bed and watch up close. He was a strong athletic boy experiencing Emily's warm, soft pussy for the first time and playing with her bouncing boobs. He fucked her in a variety of positions. When he was about to cum, he pulled out and shot a huge load around her pussy and on her stomach.

I quickly dove in and while licking it all up I heard Emily say not to swallow. I thought it was so that she could share it, but when I lifted my head with a mouthful of cum, Jeff grabbed the back of my head and pulled me into an intense kiss. His tongue explored my mouth trying to get all the cum. I was caught up in the moment and returned his kiss and pushed all the cum and my tongue into his mouth. As he broke off the kiss, I heard Emily tell me that there was cum still leaking from his cock and that I should suck on it to get it all. When I had first met Emily, I had told her that I had never done anything with another guy and wasn't interested in it. I was in shock that she would ask me to do that, but when I glanced at her she had a look of "Do it. Or else."

He had softened a little after his orgasm, so I moved over and sucked him into my mouth. I could only get a few inches in, even at his softened state, and it was true that he was still leaking quite a bit of cum. I licked and sucked to get it all, and as I did, I felt him getting hard again. That made me feel good, like I must be doing something right. I found that I didn't mind sucking his cock. The warm, smooth, hardness, and softness, felt good in my mouth. It was very erotic. I think it was just the idea of it that bothered me the most.

When he was hard again, Emily pulled my head off his cock and asked him if he wanted to take her cuckold's anal virginity. He answered that of course he would and wondered if it was true that it would be my first time. Emily replied, "Yes. Your first woman, his first man. It's a night of firsts for both of you."

Emily got me on my knees on the bed, lubed up his cock and lined him up to enter me. It was quite painful as he pushed inside me, but after his head popped in, there was less pain and more a feeling of being full. It felt good. He continued to push inside me until I thought he must be up to my stomach before he finally said he was all the way in and started to pump. The pain soon disappeared completely, and I began to experience a great deal of pleasure. He was hitting something inside me that was very pleasurable. Emily later told me it must have been my prostate. He fucked me hard and fast, then slowed to catch his breath before picking up the pace again. He must have fucked me for half an hour before he suddenly pulled out, spun me around, stuck his cock in my mouth, and squirted a huge load, which I shared with him again with a deep kiss. I indeed was not a virgin with guys anymore.

With Jeff's cock out of me I felt a sense of emptiness, but also a sense of sexual gratification that I had not felt in months. I knew that I wanted to do that again, and often. Over the next few months Jeff came over 4 to 5 times a week, usually before Emily's other boyfriends came over. From that first day, he always came in my mouth, whether he was fucking me or Emily, and he always wanted it back so he could swallow it. By the time he left for the Olympic trials, I heard him tell Emily that I had become an excellent cock sucker and had a very nice ass for an old guy. I gave him a passionate kiss and told him I would miss him a lot. After that we only met when he was home to visit. We also watched him on TV during the Olympics, or Emily watched while I ate her pussy.

That night as we cuddled in bed, Emily told me she was proud of me for doing what she wanted and that I could now have sex with a few of her other boyfriends. I thanked her for letting me suck Jeff's cock and for letting Jeff fuck me. Emily told me she loved me very much. I started to cry and told her that I loved her more than anything in this world.

Then we drifted off to sleep.

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