I met Tim in a chastity chat room about a year ago. He's a bit younger than me, and goes to school in California. He had little exposure to chastity beyond some cuckold* fantasies, and basically no exposure to BDSM. Even though he's straight, he took an immediate interest in me. I told him early on that we weren't a good fit for each other, but he never stopped flirting with me, and to be honest, I enjoyed shooting him down time and time again. In spite of this, we talked frequently over the following months while he struggled to understand the urges he was feeling.
A few months later he came to me extremely worked up. He had denied himself for four days as an experiment. I wasn't intending to play with him, but there was just something about his mood, and the way he started talking. . . I started by having him bring himself to the edge of orgasm and stop. Even though we were using a primitive text-based chat system, I could sense his desperation, and it drove me to press on.
He barely even resisted when I asked him to wait a day before masturbating, so I pushed harder. I told him he could choose to ask for permission, or just enjoy an orgasm. On a whim, I added one more thing. "Would you like to know what I will say if you ask me tomorrow?"
"I will tell you to edge for me, and then later, I will tell you no."
The next day he asked me to decide for him again. I pointed out that it would be silly since he knew I would deny him. The expected choice would be to have an orgasm and enjoy it, but his desire to be controlled was showing through. Even though he didn't understand why he was doing it, he asked me to decide for him, so I made him edge and denied him for the day, just as I said I would. Again, I told him that he could ask me the next day, and offered to share the answer he would get. "I will tell you to edge for me, and then later, I will tell you no."
On his sixth day without an orgasm, we had this conversation:**
me> so you want to let me choose for you again today?
tim> yes Sir, please
me> don't you want to know what the answer will be before you choose?
tim> i, i dont know anymore. whatever you think is best
me> well, I already decided I was going to let you have an orgasm today if you asked me. I wanted to see if you would ask.
me> I think I'd like you to choose if you'll take the orgasm, or if you'll try to go for a full week
me> just one more day :)
tim> can u just decide for me? i cant stand not knowing what you want
me> I want you to make a choice
tim> i wanna cum, im so horny i just gotta cum
me> it would give me a tiny bit of pleasure if you chose not to
me> not very much. . . I might smile a tiny bit more when I masturbate tonight. but it'd be something
tim> i wont then
tim> fuck
me> just to give me a tiny bit of pleasure? You'll put yourself through another day of hell?
tim> yes Sir
I had pushed him to the point of surrender using nothing but charm. I could have pushed him farther, had him doing pretty much anything I wanted, but it was a good amount of progress. It was a profound experience for him, and he needed a chance to cool down and think about what had happened. At the very least I had shown him how deep his submissive side runs. I let him have an orgasm shortly after our exchange.
The experience did change him. He has explored more of his fantasies since then, he bought a chastity device, and has played with a couple of key holders. I'm extremely proud to have been a part of his journey, and wish him all the best in his future.
---
* A cuckold is a person who is in a relationship where they are denied sex, but their partner is sexually active. From what I gather, there are often other humiliating / degrading elements to these relationships, but there are enough elements missing that you wouldn't consider it BDSM.
** The dialogue has been edited for readability. Some lines were combined, some typing errors were corrected. I removed some insignificant chat during the conversation, and edited out a pause that appeared in the middle. The conversation is reprinted with Tim's permission.
A few months later he came to me extremely worked up. He had denied himself for four days as an experiment. I wasn't intending to play with him, but there was just something about his mood, and the way he started talking. . . I started by having him bring himself to the edge of orgasm and stop. Even though we were using a primitive text-based chat system, I could sense his desperation, and it drove me to press on.
He barely even resisted when I asked him to wait a day before masturbating, so I pushed harder. I told him he could choose to ask for permission, or just enjoy an orgasm. On a whim, I added one more thing. "Would you like to know what I will say if you ask me tomorrow?"
"I will tell you to edge for me, and then later, I will tell you no."
The next day he asked me to decide for him again. I pointed out that it would be silly since he knew I would deny him. The expected choice would be to have an orgasm and enjoy it, but his desire to be controlled was showing through. Even though he didn't understand why he was doing it, he asked me to decide for him, so I made him edge and denied him for the day, just as I said I would. Again, I told him that he could ask me the next day, and offered to share the answer he would get. "I will tell you to edge for me, and then later, I will tell you no."
On his sixth day without an orgasm, we had this conversation:**
me> so you want to let me choose for you again today?
tim> yes Sir, please
me> don't you want to know what the answer will be before you choose?
tim> i, i dont know anymore. whatever you think is best
me> well, I already decided I was going to let you have an orgasm today if you asked me. I wanted to see if you would ask.
me> I think I'd like you to choose if you'll take the orgasm, or if you'll try to go for a full week
me> just one more day :)
tim> can u just decide for me? i cant stand not knowing what you want
me> I want you to make a choice
tim> i wanna cum, im so horny i just gotta cum
me> it would give me a tiny bit of pleasure if you chose not to
me> not very much. . . I might smile a tiny bit more when I masturbate tonight. but it'd be something
tim> i wont then
tim> fuck
me> just to give me a tiny bit of pleasure? You'll put yourself through another day of hell?
tim> yes Sir
I had pushed him to the point of surrender using nothing but charm. I could have pushed him farther, had him doing pretty much anything I wanted, but it was a good amount of progress. It was a profound experience for him, and he needed a chance to cool down and think about what had happened. At the very least I had shown him how deep his submissive side runs. I let him have an orgasm shortly after our exchange.
The experience did change him. He has explored more of his fantasies since then, he bought a chastity device, and has played with a couple of key holders. I'm extremely proud to have been a part of his journey, and wish him all the best in his future.
---
* A cuckold is a person who is in a relationship where they are denied sex, but their partner is sexually active. From what I gather, there are often other humiliating / degrading elements to these relationships, but there are enough elements missing that you wouldn't consider it BDSM.
** The dialogue has been edited for readability. Some lines were combined, some typing errors were corrected. I removed some insignificant chat during the conversation, and edited out a pause that appeared in the middle. The conversation is reprinted with Tim's permission.
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