Engaged in Chastity

Charles was sitting at his desk, in his small office, staring out the window into the busy traffic outside. His mind was full of thoughts of happy frustration as he realized he had been given everything he had asked for from his new fiancé. Rose was amazing and open minded about life. They had dated for a year and a half before he had proposed to her. Now the wedding was just a few months away and he wondered if he would be able to make it. They had met in their late 20’s and now neared the beginning of their 30’s together.

Charles sat there at his desk, to the casual observer, everything was normal. He wore a pair of dress slacks, a nice button up shirt, and a pair of trendy leather shoes. It was what he was wearing underneath his business casual apparel that had his mind drifting. Charles was wearing a cock cage and Rose was the keeper of the keys.

It had started around 6 months ago when he brought it up in a conversation with her. They had finished dinner at their favorite local pub and where on a night walk on the beach. As the waves calmed the stresses of the day, they found themselves in a continuation of a conversation that had started a few weeks prior. They had been talking about sexual interest, their sexual histories, and some fantasies of how they saw their relationship in a more sexual light. It was an exciting conversation for them to have, since it was also helping them discover what they really wanted from each other sexually.

One important thing to note, Charles and Rose to this point had not had sex together. In fact, they were virgins. It was a part of their belief system, saving themselves until marriage. They had not even seen each other naked or really done much physically affectionate things together. The first or second date had them both confessing their virginity to each other and also the desire to remain as such until marriage.

Then she asked a really important question to him as they discussed their sexual history. “So, Charles, do you masturbate?” Rose asked in her normal sweet casual tone.

Charles took a few seconds to ponder the implications of how he should answer this question. Masturbation wasn’t something he had ever talked about with anyone, let alone the woman he was falling in love with. It was a taboo subject, an embarrassing habit, and something that he was unsure about himself. Of course, he masturbated, it was something that he had done long before he even knew that the word masturbation existed. He had done it out of pure innocent curiosity as he lay in bed one night as he had discovered that his penis would become rigid just from being rubbed. Then the sudden pleasure and eruption that came after several minutes of such activity. The discovery phase of his new hobby led him down a rabbit hole of curiosity and wonder as he began to establish many interest and turn-ons. He saw the world differently from that point on. This led to a daily masturbation habit that had become normal for him. While he knew enough to keep it secret and private, he often wondered why it was so taboo in modern culture.

“Well, I um,” Charles stammered as he began to answer Rose’s question, “I do actually!” he responded to her making a confession to her that left him feeling more vulnerable than he had ever felt before.

There was a pause between them, as the ocean waves crashed and submerged there bare feet in the warm waters of the Florida coast. She was clearly considering his answer before responding to him. This was one of the things he loved about her, she always carefully thought about things before just responding. He felt a wave of anxiety fill his body as his face turned beat red as mild drops of sweat formed.

A good 60 seconds later, she responded to his confession. “I assumed that you did, but I wasn’t really sure, thanks for being honest with me.” Rose said just audibly enough so he could hear her over the crashing waves of the ocean.

“Do you?” he asked, but felt weird for asking, she had always been so proper.

Was a man supposed to ask a woman a question like this? He wondered, but they had grown so close and the fact that they could possibly spend their entire life together, he wanted to know.

“No, I don’t,” she responded to him rather quickly. “I have before, but it wasn’t something I ever felt comfortable doing or wanted to do.”

“I gotcha,” he responded, feeling a little disappointed in her response.

“It’s not something I feel is wrong or whatever, just never had the desire to do.” She remarked.

This was the conversation that had begun their discussions on the subject of their individual sexuality. As a few more talks happen over the course of a few date nights, they began to discuss what their sexuality would look like if they did get married one day. It was around a month later that they had finished eating in their favorite local pub and had begun their evening walk along the beach as the sun was setting.

He asked her a question as he attempted to navigate the conversation to a point that he could bring up the potential of chastity. “So, can I ask you something that I have been thinking about since we have started talking about sexual stuff?”

“Sure,” she responded.

“Do you mind, like as my girlfriend, that I masturbate?” he asked in a rather insecure manner.

“As your girlfriend, no, not really!” she commented. “I mean, I would rather you didn’t, but at the same time, I get it, men think about sex more than most women.”

“So, you don’t care?” he asked her.

“I mean, sure, I care, but I mean, I guess it depends on what you are doing it for,” she said. “I would hope you’re not looking at porn and stuff.”

He chuckled, “no, no porn I guess, I mean I do read sexy erotic stories and imagine stuff, but not like looking at pictures or videos on a porn site.” He said.

“What kind of stories?” she asked.

“Just stuff we have talked about, like of people discovering their fetishes or kinks,” he said as he wondered how deep into his sexual rabbit hole, he should reveal to her.

“Like how you told me you like my feet and stuff?” she mentioned.

He had admitted to her he found her feet to be sexy a month or so ago as he massaged them one day. It was something she believed easy enough as the loose-fitting pair of shorts he was wearing had shown his fetish by a visible tent.

“Yes, that has been a growing interest and actually something that many people find alluring about women.” He responded.

“And you masturbate to those stories?” she asked in a blunt manner.

“Sometimes, yes, among other stories, not just feet stuff!” he said, surprising himself with his confident admission.

“Are you thinking about me in those stories, or like, someone else?” she asked in a curious but casual tone.

“100 percent of the time, yes, it is you and me!” he answered her question.

“Do any of the stories involve like us having sex together?” she asked.

“Yes, I think I have imagined it all.” He commented.

“Like what sort of stuff?” she asked, clearly interested in hearing what the man she was in love with was telling her.

She had never had anyone tell her such things, her curiosity was peaked, and she felt a rush of excitement knowing that Charles was sexually attracted to her.

“Well, I mean, sex yes, even stuff like oral sex that we could do hopefully one day, and maybe trying out some different kinks and ideas that I have read about.” He said as they walked along the sandy shore.

“I know we said we want to wait till marriage for sex, but I had no idea you would already be imagining it in such a manner.” She said.

“Are you upset?” he asked, even though her responses had been positive and not unenthusiastic.

“No, I mean, like I said, I figured you would, but I never really thought about what you would think about,” she said. “I mean, I am glad you’re not thinking about other women.”

“I am happy your so understanding of this,” he said softly. “I was thinking you would want me to stop.”

“Well, I am trying to be understanding, but it is your body and all,” she said and then followed up with this question. “Do you think you could stop if you wanted to?”

“Wow, I don’t know.” He said. “It would be really difficult to stop.”

“Okay,” she said.

“I would like to stop, but I don’t think it would be easy.” He said.

“I understand!” she commented.

“I mean, honestly, I have been reading about something that some couples use to control the urges of men masturbating and such, but I don’t know if it would really work or not.” He said.

“What is it?” she asked.

“It’s called a chastity cage,” he said. “It fits over the male genitals and prevents him from being able to touch himself in a sexual way.”

She giggled at him and said, “I didn’t know they made those for guys, but I read about one in a medieval history textbook once, but I never knew it was a real thing.”

“Well, they make them for men now, and it is more common than you would think.” He said.

“Well, that is a thought.” She said.

And that was that. The conversation was started, but long from over. Over the next few months, they talked about it a few more times, even looking at them on the internet. He had even ordered a few secretly to try them out and find a good fit and style. By the time he was also shopping for an engagement ring, he had somewhat found the cage that he thought would fit him best. The cage was pricier than he was able to spend at the moment, seeing how he had just spent a large amount for her engagement ring and all.

The night he proposed to her was special, a nice romantic dinner at his apartment. Popping the question to her just before eating dessert. As she gave an emotional yes, he slid the ring on her beautiful finger, and they kissed. The next few weeks had been a blur to him, as it was filled with hearty celebration and joyful excitement as the news spread among their families and friends. It was truly a blissful moment and as they set the wedding date and started making all the arrangements, the future seemed bright.

As they lay in bed one night, he in his apartment and her in her own, they had a text conversation that had been months in the making.