Jack's Permanent Chastity Adventure: Part 1

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Jack's Permanent Chastity Adventure: Part 1

Postby wishful4 » Mon Jun 05, 2017 3:16 pm

This story was inspired by one of Lady M's blog posts about one of her chaste boys. With her permission, one of the main characters of this story is named "Lady M". Enjoy!


Jack’s Permanent Chastity Adventure
Part 1
It was a snowy, cold evening in the Midwest. Jack was online exploring the FetLife website, as he did most evenings, when he came across a posting in the male chastity area by a person known as Lady M. He started reading the posting and couldn’t believe what he was reading. Jack’s “hot button” fantasy had always been male chastity. To be specific, long term or permanent male chastity. He had always been captivated by the idea of his sexuality being under the control of a dominant woman. He had accumulated quite a collection of male chastity devices and regularly self-locked for varying lengths of time but ultimately couldn’t resist the urge to masturbate. His ultimate fantasy was for someone to take the keys to his chastity device and keep him locked permanently. He looked away from his PC deep in thought, then came back and read Lady M’s post again. It read;

“I am Lady M, a lifestyle dominant Keyholder. I currently have a husband and several boys for which I hold the keys to their chastity devices. This is both exciting and very satisfying for me.
I am in search of a very special young man willing to provide me with the ultimate Keyholding experience of locking a young male permanently. Those who wish to apply must meet the following requirements:
1. Have some male chastity experience and an intense desire to be locked in chastity long term.
2. Must be at least 21 years of age and be a virgin, never having had sexual intercourse with a female.
3. Must not be in a current romantic relationship.
4. Must be in good general health and currently employed
In case you think this may be your chance to have a fantasy fling with someone, it is not. I will be your remote Keyholder, although we may have some personal interaction from time to time. It is likely that I will come to exercise some control over other facets of your life, as well. But you will remain locked in a chastity device of my choosing until I see fit to release you, which could be many years, or never.
If you wish to apply for this position, you are to write a short essay to me on why you intensely desire permanent chastity and why you are the boy I am seeking. Send it to LadyM@director.net. I will be communicating with the very few that make the final cut by email before arranging a personal meeting. Think very hard about what this means before you apply. This is the real thing and not a fantasy. Don’t waste your time and mine if you aren’t serious. Lady M.

The next day, Jack thought about Lady M’s posting all day. He even masturbated in the men’s room stall at work thinking about it and looked at the posting again after getting home. He couldn’t get it off his mind as if he was being drawn to it. This went on for about a week when, finally, Jack could stand it no longer. Over the weekend, he sat down at his PC and wrote the most sincere, heartfelt essay he had ever written. Jack was certain he was the boy Lady M was looking for. It was as if she was calling to him. After much soul-searching, he took a deep breath and hit the send key.

After a week, then two, went by with Jack checking his email several times a day, he had just about given up. Finally, late on Sunday night, he decide to check his email once again and there it was, an email from who other than Lady M. Jack was afraid to open it. What if it was a rejection? He took a deep breath, closed his eyes and clicked on the email. It read:

Dear Jack,
I had quite a response to my posting on FetLife, much more than I expected. For the most part, the essays, if you can call them that, were sheer rubbish. Many others were derogatory in nature. Then I came across your essay. It was beautifully written and you are to be commended for your effort. Given the tone of most of the others, yours was quite refreshing. I just wanted to let you know that you have been chosen for additional consideration for my permanent chastity candidate. I would suggest the following as we start this vetting process. I require my chaste boys to be completely hairless in the genital area so you should start shaving right away in order to get accustomed to it. Additionally, start wearing the smallest chastity device you now have on a regular basis. It so happens we live fairly close, so I will be arranging for further in-person interviews and will also measure you for a custom stainless steel device which will be locked on if I decide on your final selection. Finally, Jack, you really need to think about the reality of the journey we are about to embark on and be sure it is what you want. Once the lock clicks, there can be no turning back. It will be a life changing event for you, not a fantasy. In closing, thanks again for your sincere essay. Please provide your cell number for texting and I look for to meeting you.
Lady M.

Jack’s heart was beating so fast, he thought it was coming out of his chest. He simply couldn’t believe it and reread the email again. It was true, Lady M wanted him. He thought about what she had written for a long while. He finally decided, what’s the worst that could happen? All locks can be picked. If I don’t like it I can simply back out. After a hasty reply thanking her and providing his cell number, he smiled at the thought of how hot it would be to meet Lady M in-person. Jack had never had sex with a real woman. Maybe she will want to have sex with me, he mused. Not wanting to disappoint Lady M, he immediately went to the shower, shaved his genitals, and locked his chastity device on, but not before masturbating to one of the most intense orgasms he had ever felt.

A couple of days later, Jack’s cell phone beeped with a text. It was from Lady M saying she would be in his area on Sat and would like to begin the in-person interviewing. Would he be available to meet after Lunch? He answered that he would be available. She replied that she would advise a time and place Sat morning. Jack was beyond excited at the prospect of meeting his future Keyholder, Lady M in person. What would she be like? He knew she would be devastatingly sexy. He would make sure and dress nicely and look his best. Who knows what could happen?

Lady M’s instructions for their Saturday interview arrived via text on Friday evening. Jack was to show up at a small business suite at the strip mall on 24th Ave at 1pm sharp. The door to vacant suite 245 will be unlocked and he was to enter and lock the door behind him. He was to wear his chastity device and leave the key at home. His instructions were to sit down in the chair provided and await Lady M. DON’T BE LATE was at the end of the text. Jack was a little bummed. How could we have sex if I’m locked up, he thought. But, it is our first meeting so she is just being careful. He decided he would follow her instructions to the letter.

Saturday morning arrived and Jack was sitting outside the address given by Lady M. He was early. The suite was vacant and had blacked out windows and door. He waited until a few minutes before the time Lady M had specified, then got out of his car to enter the suite. This was a safe part of town so Jack wasn’t worried for his safety but he was very nervous about the interview. He pulled on the entrance door handle and the door was unlocked. He entered, locked the door behind him, and sat down as instructed. The front part of the vacant suite looked to be a waiting area. About ten minutes had passed when Jack heard noises coming from the back of the suite. Shortly afterwards, a door opened and a woman stepped through. She was a tall lady with dark hair and was dressed in a white blouse accented by a tightly laced black bodice that supported her beautifully large breasts. It was complemented by a medium length black leather skirt. She was obviously older than Jack and she was hot!

“Hello Jack, I’m glad you came!” she said in a reassuring voice. Jack was so mesmerized, he was unable to speak. “Uh, Uh, hello”, Jack said. Lady M held her arms out to her side and twirled around in a circle. “You like?” she said. “Uh, Uh, well, yes, you are beautiful” he said. “Well, thank you, Jack”, Lady M said, “I don’t normally dress this way, but I did today just for your benefit. I trust you are appreciative?” Uh, Uh, Ye.., ye.., Yes, thank you, Jack stammered. There was a few moments of silence before she continued. “Come into the back office with me and we will get the interview started”. As Jack entered, she closed the door behind him.

“Now”, Lady M stated, “this is an opportune time to acquaint you with the first rule for my chaste boys. If you are in my presence, you will be naked except for your chastity device. So, I want you to take off all your clothing right now, then we will continue”. Jack was shocked and did nothing for several seconds, then slowly started the process of undressing. Once he was completely naked, he was blushing with embarrassment and didn’t know what to do with his hands so he put them in front of his crotch. “Hands behind your back and clasp your fingers”, Lady M said. “Let me have a look at you”. She put her hands on his shoulders, rubbed them up and down his sides, then walked around and held his face in her hands. Jack’s arousal was so high he could barely breathe. “You are a beautiful boy”. “Sit down in the chair. I have placed a towel in it for you” she said. “Now I want to know everything about you that you didn’t tell me in your essay”.

As they talked and time went on, Jack was starting to become a little more comfortable despite his naked state and the two of them talked about everything from Jack’s family to subjects like his masturbation and other habits and hobbies at home. He loved being near Lady M. He could smell the leather in her garments. That, and her sexy voice was making him quite uncomfortable in his cage. After nearly an hour of conversation, Lady M was reasonably sure Jack met the criteria she had come up with that would fit someone she could permanently lock in chastity and manage without interference from others on the outside like family and friends. Jack had no siblings and his parents had passed on. He didn’t have a girlfriend or other friends he regularly hung out with. She expected it would become necessary for him to eventually become completely dependent on her to manage things even outside the realm of chastity, but Lady M had lots of experience at this and felt she was up to the task plus this would be her supreme challenge, to keep a young virgin male locked in chastity permanently. She had fantasized and even dreamed about it. Now, it was about to become a reality and she wanted to do it properly.

“Jack, I think you have passed all my initial tests as far as a candidate for my permanently chaste male position, but I want to be assured that you really want this, too. Are you absolutely sure this is what you desire? “Asked Lady M. Jack replied, “Yes, I have thought about it and I feel sure I want to do this. I’ve even dreamt about it. I haven’t been able to get it off my mind since reading your FetLife posting. I know I’ll regret it if I let this opportunity pass”. After a short silence, Lady M continued, “Very well, there is someone else I want you to meet. She will play a very big part in this, too”. She picked up her phone, dialed a number and said, “Ms. Pat, can you come in, please”. A few seconds later, another door opened and an older lady entered. Jack didn’t know what to make of this. Lady M sensed his discomfort and said, “Don’t be alarmed. This is Ms. Pat. She provides my custom made chastity devices and will be measuring you”. Jack looked at Ms. Pat with a confused look. “Standup please, hands behind your back” Ms. Pat said firmly. Jack obeyed instantly, looking at Lady M as he did so. “Good boy” said Lady M. Fortunately, Jack’s embarrassment had shrunk his small penis and Ms. Pat was able to get all the measurements she needed in short order. “Okay, M, looks like a slightly smaller and shorter cage than the one he is wearing, and a little smaller cuff ring, too” “I think I have everything I need”, Ms. Pat said. “Very good” Lady M said, “I have some additional requirements for this device but I’ll let you know about them later”. Ms. Pat stepped back towards the door, crossed her arms and looked at Jack. Jack was puzzled and looked at Lady M. She said, “Jack, you should always thank Ms. Pat when she does something for you. She will be very involved in managing your permanently chaste condition, training you, and providing other services for us”. Jack lower his eyes as he turned towards Ms. Pat and said. “I’m so sorry. Thank you, Ms. Pat. Please forgive me.” “You are new and have a lot to learn, but we’ll help you get there”, Ms. Pat said as she turned and walked out the door.

After exchanging goodbyes with Ms. Pat, Lady M turned to Jack and said, “We are about done for today. I will text you when your device is ready. We will, again, meet here and please remember your protocols in our presence. You and I will review a Chastity Contract that will cover what is expected from both of us and go over some other matters. Once you sign the contract, Ms. Pat will fit your chastity device, lock it, and give me the keys. I will also have instructions for you to follow in the days to follow. We will have you report back here at certain intervals to assess your progress and take care of other issues. Do you have any questions for me before we leave?” Jack thought for a minute. “Will I get to see you again, Lady M?” Jack asked. Lady M got up from her chair and embraced Jack, holding his head firmly to her chest just above her beautiful breasts. Jack was in heaven and thought he might cum then and there. “Yes, for your next visit, both Ms. Pat and I will be here” said Lady M. She gave Jack a peck on the cheek and told him to get dressed and leave via the front door.

At the risk of a speeding ticket, Jack drove home as fast as possible. He could think of nothing else than getting his chastity device off and masturbating. He was so excited. Lady M had hugged and kissed him all while he was naked. He was so close to her beautiful breasts when she hugged him and could smell her leather and her perfume. After stroking to a fast and furious climax, Jack dreamed of his Lady M all night long.

The following day, Lady M was downtown at Lunch when her phone signaled a text message. It was from Ms. Pat.

Pat: Well, your ladyship, what did you think of Jack? Is he going to be the one?
LM: Yes, I think so. He’s obedient, submissive, and has the intense desire for what I have in mind. What did you think?
Pat: I agree, but I can see some risks. Surely you noticed how smitten he was with you. He is very young and very pretty. Are you going to be able to maintain your persona when he batts those puppy dog eyes at you and begs for attention?
LM: Yes, I know. But that affection will be useful in helping him get through the first couple of months in chastity. With regard to that, if you can, I would like for you to supervise his first couple of milkings so he can develop a bond with you without me present. Be firm and strict with him. Discipline him for the least little infraction. He needs to know what the discipline part of our contract will involve.
Pat: Oh, I see! You just want poor Pat to be the one to go home with sopping wet panties from playing with him. Well, I may just throw this pretty boy down and teach him how to properly service a lady, then take my rattan cane and soften up his pretty bottom. I could turn his brain into mush inside of an hour, then put a leash on him and take him home.
LM: Lol! Pat, you are terrible!!
Pat: Haha! Just food for thought if you ever tire of him. I’ll txt you when his device is ready. Shouldn’t be too long. Take care!
LM: OK, BTW, Thank your friend Jackie for the use of her vacant property.


Jack checked his email before leaving for work and there was a surprise email from Lady M. It read:
“I suspect you were naughty when you arrived home after our session together. I want you to lock your chastity device back on and text a picture of it installed to me right away. I would also like a similar picture every day. You will be required to do this when you are permanently locked so you might as well get used to it now.” Jack immediately did as she requested without a second thought.

As one week went into two, wearing a chastity device continuously began to feel normal to Jack. It made him wonder what it was going to be like to be permanently locked. Sometimes, when he thought about it at night, he couldn’t help himself. He would get up, unlock, and masturbate, then feel guilt afterwards. He knew Lady M would not approve, but what she didn’t know wouldn’t hurt. Right?

Jack was just finishing up at work when his phone beeped. It was Lady M.

LM: Hi Jack! Your device is almost ready. Are you ready for me to take control? Are you ready to belong to me and only me?
JACK: Yes, I’m ready! I want so much to see you again. I’ve been thinking of you since we last met.
LM: Well, I’m flattered. Meet me this Sat at Suite 245 again, 10am. Make sure your device is locked on and bring your key. DON”T be late or forget the protocols we discussed before. I’ll wear something special just for you!! Look forward to seeing you.
JACK: Ok, See you there! Thank you so much!


Saturday morning Jack was, again, early, sitting in his car outside the suite trying to calm his nervousness. Lady M said she wanted him, that she wanted him to belong to her. What did that mean? Just before the allotted time, Jack entered, locked the door, and began undressing without a second thought. Within a few minutes, the door to the back room was opened slightly and Jack heard a female voice telling him to come. He stood up and, holding his clothes in hand, walked into the back room. It was dimly lit, but he saw Lady M sitting at the table with Ms. Pat standing behind her. He blinked his eyes and tried to focus. Lady M’s black blouse was very sheer and he was sure he could see her nipples through it. When she stood up, her hardened nipples poked into the fabric and he could see her beautiful breasts held up by a black quarter cup bra exposing the nipples.

She held her hands out to the side and said, “You like?”.” Gosh, yes, you look fabulous. I can’t believe I’m here with you” Jack said. Lady M continued, “Well, I wore this just for you. I’m glad you like it. Put your clothes on the chair, give me your key, and we’ll get started.” Jack did as she directed and stood in front of the table, hands clasped behind his back as he thought she would want. “Good boy”, Lady M said.
She placed some sheets of paper on the table. “Jack, This is our chastity contract” Lady M began. “ It is very simple and says that you agree to remained locked in a male chastity device with me as you Keyholder until I decide to unlock you and you understand there are no limits on the length of time I may decide to keep you locked. I want you to read it over careful with special emphasis on the Discipline section. If you choose to violate our contract in any way, this section will apply. Take as long as you like to read it over and feel free to ask any questions you may have”.

Although Jack was distracted by Lady M’s sexy attire, he tried to read the contract, but couldn’t resist looking up at her breasts every few seconds. “When you are satisfied with the contract, sign at the bottom and we’ll move on to bigger and better things” she said. “It looks fine,” Jack said, then picked up the pen and signed. “No questions?” said Lady M. Jack shook his head no. “Very well”, she continued, “Ms. Pat, would you install Jack’s new device please”. Ms. Pat opened up a box on the table and pulled out Jack’s new chastity device. It looked quite a bit smaller than the one he was currently wearing. Instead of one hole for the lock, it had an additional small hole in the locking post.

Ms. Pat unlocked Jack’s device and pulled it off. Following that she quickly removed the cuff ring. Almost as quickly, she installed his new cuff ring that goes behind the scrotum. Jack winced a bit as she worked his balls through the new slightly smaller ring. Next, she held up a round plastic ring with what looked like petals of a flower that all pointed in towards the center of the ring. Jack was puzzled at what it was. “This is a new anti-pullout device I have designed, Jack. It is completely comfortable to wear but effectively prevents you from pulling out the back of the device. Normally, trapped ball devices like this can be defeated by pulling out the back, but this will make doing that very uncomfortable, so don’t try it.” Ms. Pat said. She slid the flower petal looking ring onto his penis followed quickly by the new cage. “This new cage is a bit smaller than the one you are used to, and it won’t allow any erecting at all. In time, you will find it to be more comfortable.” Ms. Pat added. “Now, we are ready for the locking. Lady M, would you like to do the honors?” Lady M walked around the table and put her arms around Jack and hugged him close. “Thank you so much for doing this for me, Jack. I promise to be a good Keyholder for you. Welcome to your new life of chastity” said Lady M. Jack didn’t hear a thing she said. He was so close to her almost exposed nipple he could have touched it with his tongue. With that, she bent down and clicked the lock on his device. Then, she took out a smaller plastic, numbered, security tag and secured it through the smaller hole in the locking post. In addition, she placed a small circular adhesive sticker in the key hole in the lock.

“Now, Jack, pay attention” Lady M said. “This numbered security seal will let me know if the cage has been removed from the locking post. The small round sticker in the key hole will alert me if you try and jimmy the lock so don’t try. The anti-pullout device will cause pain if you try and pull out the back. That’s as secure as we can get without a piercing and you are not ready for that, at least not yet”.” Don’t forget your requirement to send a pic of your locked device every day. Failure to do so will invoke the Discipline aspect of our contract”.

Jack was a bit overwhelmed by all of this activity. He looked down at his genitals and, locked in his new device, they were smaller than he had ever seen them. He looked over at the smiling Lady M and said “Lady M, it’s so small and so tight”. “Yes it is, Jack”, Lady M said. “I’m glad you mentioned that, because I need to advise you on some things with regard to coping with your new device. It keeps your penis very small and it should stay that way. That’s the way a chaste penis should be. A properly fitted device should stop any erection attempt in short order. It’s possible that you may have some moderate discomfort at certain times of the day or night. I would suggest you deal with these issues early on before things get too painful. Sit in a hot tub of water. Use a little dab of lubricant if needed, that sort of thing. Just be aware that unlocking is not an option anymore so be proactive, so to speak”. Lady M continued, “We are about done for today. Plan on coming back here in two weeks for a gauge of your progress and maybe some relief if you have been a good boy”.

As Jack was getting dressed under the watchful eye of Lady M and Ms. Pat, he remembered his protocols. Jack turned to them and said, “Thank you Lady M and Ms. Pat. I’m honored to belong to you, Lady M.” “Good Boy” said Lady M and Ms. Pat nodded her head in approval. “Lady M, will I get to see you again soon?” asked Jack. Lady M replied “Jack, I’m very pleased to have you as my very special chastity boy. Like all of my boys, I will be there for you if you need me. One thing that being in chastity is about is putting someone else’s needs above yours. You should always be thinking about how to please your Keyholder”.
After Jack left, Lady M and Pat were finishing up and chatting about the day’s events. “Your thoughts?” asked Lady M. Ms. Pat said, “I had my doubts, but it went very well, I think. He has tremendous potential as a submissive. In his case, it’s a need you or someone is going to have to address at some point because his chaste condition is going to increase his submissive need. I’ve seen it before.” Lady M thought for a minute and replied, “I’m trying not to think this too far ahead. Poor Jack is going to have a rough couple of months getting used to being locked in that small device. We have to help him through that. If he can stayed locked for 2 months, he’s good forever. I still would like you to handle his first couple of milkings, as we discussed earlier. I’ll have hubby bring the milking bench over next week. Make sure he gets a taste of your cane, as well. If we do this right, we’ll have a permanently chaste submissive for life. We are pushing new boundaries. I’m excited about the future”.

Stay tuned for Part 2.
Wishful4
Current Device: MM Jailbird
Previous devices: CB 6000s, CB 6000, MM Queen's Keep (2)
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