Prison Made Me a Better Man Ch. 01

Chapter 1 - Going to Prison

I looked at my calendar to see that I had a doctor's appointment today. It was with some new doctor in the city. My wife, Linda, set it up for me a month ago under the pretense of a 'joint health checkup'. It turned out that this Dr. Fleming was a well-known female sex therapist who had a great reputation for helping couples improve their sex lives. While initially skeptical, I kept an open mind after reading glowing reviews from her patients, both women and men. During the first visit, she documented general information on our relationship and sex history. Dr. Fleming eventually won me over with her knowledge and trustworthiness, and managed to get me to share my interest in kinky fetishes including my secret desire for submission to women. Even as I revealed some things, I also kept others to myself. Linda encouraged me to share more openly. It felt like a safe environment, so I proceeded to go deeper, explaining my desire for getting spanked, which led to some follow up questions around the history and nature of it all. Then little by little, the doctor gently led me to reveal my other, more shameful and taboo desires as well, including my most intense and humiliating fetish of being turned into a sissy and ridiculed by my wife. Dr. Fleming was very professional, and did not judge us in any way.

The second visit involved some blood work and physical testing for me to measure if I had any medical issues. Happily, the reports came back negative, confirming that I was sexually healthy for my age. Linda and I were both relieved to know that I was functioning well. In the detailed reports, at the bottom of one page, there were two numbers noted under the acronyms LP and GP. It read LP 8 and GP 9. I asked Dr. Fleming for clarification on what those meant. She explained that LP stood for length of penis, and GP stood for girth or penis. When I asked for further clarification on the numbers, she hesitated, then explained to me in a softer voice that the numbers represented percentiles. My face turned red as I understood the implications. Fortunately, it looked like Linda did not hear it, and I quickly changed the subject. The doctor moved on to explain the rest of the report.

On the way home from that visit, things were mostly quiet. Then Linda asked me, "About those LP and GP numbers, what does it mean exactly? I didn't quite catch what Dr. Fleming said."

I stammered at first, but then answered half the question, "Oh, it's just a relative measurement of penis length and width, when erect." That much was true.

"And the 8 and 9? Is that centimeters?" she asked.

"No, it means my length and width are 8 out of 10, and 9 out of 10, not the very top end of the scale, but very good." I lied, to save face. She seemed satisfied, and we let the matter drop.

Then, on the 3rd visit, Dr. Fleming had us answer various questions to understand our desires, satisfaction, and barriers to achieving an ideal sex life. She met with us both individually and jointly. We ran out of time, and had a follow up 4th visit to continue the discussions.

After a month of these visits, the office scheduled a special, two-hour appointment to share Dr. Fleming's diagnosis and recommendations. I was a bit apprehensive, but figured we had to go through with it to get the benefits. "We may as well hear her out," I rationalized.

In the privacy of her office, the doctor walked us through the results to explain that I was suffering from three things that together were causing friction and dysfunction in our intimate life. The first diagnosis was that I suffered from a hyperactive sex drive and it was made worse by a habit of daily masturbation. At first, I thought this was not a bad thing necessarily. Then I was hopeful that the remedy would involve curtailing my masturbation while increasing sexual frequency. That would have been a great trade up in my mind. However, it did not turn out quite the way I imagined.

Dr. Fleming continued to explain the second diagnosis which was more critical of me. She was as kind and compassionate as was possible, but effectively said that I was being selfish about focusing only on my needs, that I was letting my male ego dominate our marital relationship, and that I had been setting up unrealistic expectations for far too long in our marriage.

I asked for the final diagnosis, figuring it could not get any worse. Dr. Fleming explained that although I was able to verbally admit my desires in a therapy session, I was still repressing myself and hence unable to accept my taboo desires more openly with Linda. She concluded, "You have certain deep-rooted, innate tendencies, but because of cultural conditioning and feelings of shame, you resist from accepting your true self, which makes it hard for Linda to engage fully and intimately with the real you. She's trying to reach out to you, but you're hiding."

After dropping all this on me, I felt woozy. I drank some water and walked around, taking some deep breaths. I went into a daze as she gave my wife a shorter and much milder assessment of needing to do self-care and make herself a priority in order to rekindle her own, latent sexual desires.

Next Dr. Fleming explained how we had great potential to achieve an epic relationship, that it was in our control, but it would take hard work to get there. She asked Linda, "Are you committed to doing what it will take?" She agreed. Then came the difficult part. The doctor asked me if I was also truly committed to making things right. I agreed, believing that I could make the changes myself by paying more attention, being more supportive, and channeling my expectations in healthier, more productive ways. I looked to Linda for confirmation, expecting her to reinforce her support. She did not look convinced, however.

Dr. Fleming leaned forward, looking at me. She asked Linda if she could have a private word with me. After Linda stepped out, Dr. Fleming explained that for my relationship with Linda to get better, I needed more help than I realized. She explained how my subconscious attitudinal and behavioral habits were so deeply ingrained that I would not be able to fix things on my own. Nor was it something that Linda could guide me through. I argued and dissented for a long time before she shared her analytically rigorous evidence which helped me come to terms that she was probably right. Upon reflection, I realized that I had a life history of trying or pretending to help myself, only to fail after a month or two, or sometimes even after a week or a few days. It was like being an alcoholic. I needed external help. She told me that this is not about the fees - she genuinely wanted to help us. Insurance was covering everything in any case, so it didn't matter to me.

I asked the doctor whether was hope. She answered, yes and no. After inviting Linda back in, Dr. Fleming explained that it was possible for our relationship to be blissful, but only if I were committed to following her treatment plan for 6 months. I asked her what it entailed. She said, "In consultation with Linda, I have developed a personalized treatment plan for you to consider." I looked at Linda to confirm if this was true. She nodded quietly. They had already discussed all this.

The doctor proceeded to explain that the program would involve having me wear a chastity belt. My penis would be fitted into a custom-made, professionally manufactured device designed for extended caging. It would prevent me from experiencing sexual stimulation, including pleasuring myself. It would start with one day on, one day off, then two days on, one day off, then three days on, one day off. After this, she said I would become very comfortable wearing it. At that point, I would be locked into the chastity belt prison for a minimum of one full month without any sexual pleasure.

"Wow, that sounds kind of intense. It would have been nice to consult me on this, don't you think?" I said to both of them.

Doctor Fleming reassured me, "I understand how you feel. This is something I developed and then consulted with your wife first, because I needed her to understand your psychology and accept the role that she has to play in helping you through this period."

"And what about me?" I asked.

The doctor explained, "Of course, it affects you much more directly. The reason I didn't consult you with it from the beginning is exactly because of the reaction you're showing right now. Resistance. This is normal. No one wants to go to prison. But sometimes it's necessary."

"So, I don't get consulted. You're not asking. You're telling. Is that right?" I asked.

Linda responded in a soothing and loving tone, "Honey, let's look at this another way. Forget about whether you were asked or told, and who's making decisions. That's not the point. We came to Dr. Fleming to get help, and to improve our intimacy and sex life. This is the route she's recommending we take. That's all. No one is forcing us to do this. We have to decide if it's right for us, and whether we want to try to fix things."

We all paused for a brief silence as I absorbed the implications. Dr. Fleming added, "V, I've seen many patients over 30 years in practice. Everything I've learned about you tells me in black and white terms that the diagnosis is right. I am very confident that prison will make you a better man when you come out of it. You will be happier."

"And I'll be released after one month?" I asked.

Dr. Fleming elaborated, "Yes, possibly. Release would be contingent upon satisfactory completion of various conditions. Sometimes we find that it takes longer, but you'll definitely be considered for release after the full month."

Linda consoled and pleaded with me to give it a chance. "V, I know this will be very difficult for you, but also so good for you and me both. Please trust the process, for us?"

My mind was reeling from all this. Dr. Fleming elaborated that during this time in prison, I would be under intensive training on how to please my wife inside the bedroom using my tongue and various vibrators, and as well as outside the bedroom with relationship exercises, helping with chores, and behaving more selflessly. She also scolded me for the little lie I had told earlier. "V, I corrected Linda's understanding of your penis size measurement results. You're a statistician. You should know what percentiles mean. Lying about it was not a respectful thing to do."

Linda admonished me as well, "V, I knew something was off about what you told me. Dr. Fleming explained to me that your 8th and 9th percentile rankings mean that your penis size is among the bottom 10% among men."

Dr. Fleming added, "While you're away in prison, Linda will be free to find sexual pleasure through her choice of vibrators and dildos. These will almost invariably be in the upper third percentiles in terms of size." Linda blushed as she imagined all this.

Next the doctor also mentioned, "V, you will be required to give up your male underwear during this time, to be replaced by women's panties and other lingerie to be worn at various times to help you control the ego and surrender yourself to Linda."

"Anything else?" I asked.

"Yes, thanks for asking. You will also be given periodic corporal punishments to assist in the attitudinal adjustments required to sustain behavioral modification." After another pause, she added that "V, these punishments will be 'memorably more painful' compared to what you have experienced from Linda to date, so it will be important for you to make a sincere effort in behaving well."

I was aghast at the severity of this plan. I needed some time to think about it. On the way home, my wife and I talked about it. She felt strongly that this was the right path. "It's easy for you to say," I complained. She told me to take my time. The doctor had given me references to speak with about their experiences. I spoke to three other men that week, and learned from each one that they had been in a similar situation as me, but come out of it much happier after the treatment. I heard repeatedly and sincerely from them sentiments along the lines of 'it changed my life immensely', it was a 'tough but fair experience', 'it gave me a new lease on life', 'it was the best thing to happen in my marriage,' and 'it was very difficult, but totally worth it.' I started to come around. I confided with Linda that I was scared but ready to do it. She held me and told me she loved me for my commitment, and that she would do everything in her power to support our journey. Linda promised how the end reward would lead to better, more fulfilling sex than ever before. I looked at her eyes and saw that she meant it. I agreed.

The next week, we went back to Dr. Fleming's office to sign the paperwork. The doctor explained one more condition to the two of us. "I find that many times, it can be difficult for one or both partners. There may be times when you want to give up. Resolves can weaken. But for this treatment to work, it needs to be just like prison - meaning that there's not changing your mind. It's not voluntary. You can't get out of it until it's over. I need both of you to sign the key-holding and release rights to me."

Linda asked, "But what if we both find it untenable and just want to quit it?"

Dr. Fleming agreed, "Obviously, this is a therapeutic treatment for consenting adults. Ultimately, we cannot legally hold V in chastity against his will. However, we don't want our patients to engage in this journey with doubts. For this reason, we've set it up so that there would be a very steep financial price to pay for early release, something intended to deter patients from quitting too easily. You need to go into this with full commitment, or not at all. I'd like you both to think this over for at least 48 hours, and then if you agree, we can move forward."

We took the contract home to review. We understood that we would lose a $25K deposit if we were to quit. We could not afford that, so it would effectively ensure that we had to be committed to seeing it through, come hell or high water. Linda left it to me to decide, but I could tell that her heart was in it. I considered that worst case scenario, I might have a miserable month of chastity time, maybe longer depending on the conditions imposed. But eventually we would move forward. Best case scenario, I would regain a stronger, happier relationship, with more sex. The pros outweighed the risks. I met one of the guys she had given references for just to be 100% sure. After two days, I decided to do it. Linda was overjoyed. We signed the papers, made the deposit. Only two weeks later, we got a call from the office that my custom-made chastity belt was ready.

At the office, a nurse helped strap me onto a table which allowed my legs to move apart. My arms were also restrained down to prevent any movement. A nurse showed Linda how the device would fit onto my penis. It felt like a glove, as the measurements were precisely designed for me. It felt weird, but comfortable. Dr. Fleming came in to examine everything. She gave Linda a small padlock. Linda smiled and put the lock on, clicking it shut. Then I was released and allowed to get dressed. It felt odd not to be able to touch my own penis. Dr. Fleming left the key with Linda, explaining the instructions for this initial period. "Remember, one day on, then tomorrow off. Then two days on. One day off. Then 3 days on. On day 8, you come back in here."

The first day required some adjusting. The night was the most difficult because I could feel my penis trying to get an erection. The next day, Linda unlocked me after 24 hours. I was able to masturbate with satisfaction. When the two-day session began, I found it harder, but after the release, I masturbated several times, this time in anticipation of being locked up for 3 entire days. As the chastity time grew longer, I started to feel more pressure and desire for release. I worked harder to please Linda. I found my this initial adjustment period tougher than I expected, especially the last 3 days. I was constantly crawling on the walls, with my penis raging at times, objecting to being imprisoned.

On day 8, we returned to Dr. Fleming's office. The nurse asked me how the belt was fitting, whether it needed any adjusting, and so on. I told her it fit well. She led me to the room where I was strapped onto the table where she examined everything to be sure everything was in proper working order. She removed the device for cleaning. I could not control myself. My cock grew to its full size. I was waiting eagerly to pleasure myself soon. However, she put an ice pack on my penis instead. I screamed out but I could not move, thanks to the restraints all over my body. She sounded surprised as she told me, "I thought Dr. Fleming explained to you that your chastity prison sentence begins now."

"Well, yes, but I thought there would be a day break before that begins, no?" I pleaded as she continued to hold the ice pack against my shrinking penis. The nurse shook her head and explained that according to her records, my one month in prison had officially begun, right now. I asked her to check with the doctor. She did not like this, but she stepped out of the office to ask.

Ten minutes later, the nurse returned with Dr. Fleming and Linda in two. Dr. Fleming straightaway explained, "V, I understand you had some confusion about the chastity timing. It works just like in a court of criminal law. When the jury finds you guilty and the judge decides on a sentence, you go straight to prison. You don't get a break before it begins!" she said flippantly, like it was some kind of game. I cringed as I realized that there was not going to be a break between my initiation and this very real prison sentence. Moreover, I came to understand that the 6 days I had spent so far in chastity would not count towards the month.

By this point, my poor penis had lost its erection. I felt Linda's sweet hands cupping my balls and the electrifying touch of her hands. Alas, it was only for the purpose of re-fitting the chastity belt on. She looked at me lovingly, kissed me. The nurse gave her a different kind of padlock. Linda showed it to me. It was a titanium lock, unbreakable. "I'm sorry V, but this is all for our future. Thank you for understanding." She clicked it shut, locking my penis up. I shuddered. Dr. Fleming took the key from Linda, explaining that it would be kept under lock and key in her office in a very secure location. After I was released, I was unable to find my clothes. Linda had packed them up into a bag. The nurse asked me to step into a thin cotton hospital robe which she tied behind me.

I was then led to another room where I was again restrained on a bench, this time face-down onto a padded bench, with my head slightly down and buttocks elevated. My hands, ankles, and body were securely fastened. The nurse pulled the string holding my robe together, causing the robe to part and fall away. My buttocks were now bared. Dr. Fleming opened a cabinet to retrieve a paddle. She handed it to Linda who paraded it out in front of me, tapping it in her hands as I looked helplessly at the fearsome looking wooden instrument of punishment. She lectured me sternly about the expectations in prison, and rattled off a series of behavioral changes she expected me to make in my life going forward. Then, under the guidance and encouragement of the doctor, Linda took her position to my left side and proceeded to paddle me quite hard, more than I had ever suffered from her before. I was howling in sweet pain after about 30 strokes. The doctor instructed her at various times on how to strike more firmly. I buckled and pulled at the restraints uselessly while my cock grew hard in its cage. After Linda finished with another 20 strokes, she caressed my bottom, soothing it. She came around to face me, embraced me, and whispered, "V, thank you for taking this first step in our journey together. Please understand that this is all for your own good. I love you."