The blow job challenge!

 My next major achievement all started with a caption. I use to send Mistress captions related to tease and denial and chastity to give her ideas or perk her interests. I found this one caption ( which I don’t have anymore and can’t seem to find again on the net) that had to do with a blow job, it was along the lines of “ if you can last 5 minutes you can cum in my mouth but if you cum before than you’re getting locked up for 3 month”!  This caption and idea caught my attention so I decided to forward it onto Mistress, nothing was really said right away but she also liked that idea. 

We were having a few adult beverages one night and playing darts when the caption got brought up. We are fairly competitive while playing games or sports and tend to make friendly wagers, our wagers are usually for house hold chores or sexual activities. This particular wager was for time, if Mistress won a minute got added to the clock and if I won a minute got taken off the clock. It was now official that there was going to be a blow job challenge. I was a bit in shock I didn’t think Mistress would go for that. At the time we were trying to conceive and I didn’t think she would be willing to lock me up and deny me since it would take away from our time to have sex. I had so many thoughts running through my head that I wasn’t playing my best game. Mistress took a strong lead right out of the gate but in the end I pulled it together and barely came back to win it. 

I don’t even know why I planted that seed in Mistresses head, she is very good at giving head and has only improved over the years. Since we started our adventure her blow jobs have turned into more of a sensual tease, but she still knows how to get down to business if she wants to get a job done. When she took on the power and control in the relationship the amount of blow jobs I got decreased, they were now reserved for special occasions or just as for play or a tease. 

I thought for sure Mistress was going to set me up to fail. If she really wanted she could have teased me right to the edge than finished me off in a minute or less with her mouth. But to my surprise she didn’t, there was only a few minutes of touching and than she reached for her phone and set the clock     . Once her lips made contact she hit the start button and placed the phone where I could see it. Only 4 minutes to go I should be able to handle that. Mistress wasn’t using her slow sensual tease speed but she wasn’t giving it her 100% either, I watched the clock tick down to less than 2 minutes and I started to think “I’ve got this” !  The clock is now down to a minute and Mistress has picked up her speed considerably, I was now at the point where I needed to start thinking unsexy thoughts. Mistress must of had a great sense of time because at about 40 seconds left she brought in her A game, full on deep throat as fast as she could go. I had went from nowhere near the edge to right over the edge in a matter of 20 seconds, I couldn’t hold out any longer and ended up coming in her mouth. She wasn’t even done swallowing by the time the alarm clock went off. I was still hard and leaking when she got up and said “ you were so close but go walk that off so we can get you all locked up”. 

 

As she was locking me up it hit me that 3 months is a long time and I had never done anything to that extent before. A few weeks past of teasing me and pleasure for her and I started pointing out that the caption never said anything about 3 months of denial just chastity. Mistress more less laughed and said they go hand in hand. It was another few weeks later so about a month of denial when Mistress got really horny and decided she couldn’t go 3 months with out her cock in her so she let me cum. From there on out I was still denied but not when it was her fertile time. 

I think it was almost 2 months into my sentence when we went out bar hopping for Halloween. Mistress was nice and let me out of the cage for the evening since I was going to be using a lot of public washrooms, but she made it clear that I would need to get locked back up before the night was over. We ended up shutting down the bars and it was late when we got back to the hotel room. I wanted to shower to rinse the temporary die out of my hair so I didn’t stain the pillows, by the time I was out of the shower Mistress was sound asleep. When she woke up in the morning she rolled over and grabbed her cock and said looks like someone’s 3 months are starting over from scratch. 

I ended up completing my 3 months with no other mishaps making 92 days of consecutive chastity my new and current record. During that time I was let out once or twice a week for proper cleaning and depending on Mistresses mood playtime. 

Holy Trainer arrival

My Holy Trainer showed up a few weeks after I completed the 60 day challenge. At the time I was out and free. We were making up for lost time after all those days spent at work and time locked up, just more less enjoying playtime when we wanted. But of course when it showed up I had to try it on.

I was instantly impressed with the difference between that and the CB 6000. The first thing was only 2 pieces so way more user friendly to put on, the ring style and size made for a more comfortable feel and the material it is made out of made for a way better sleep. Down side was it only came with one ring and the method they suggest to find the right ring size didn’t work for me. I ended up going with a 45mm ring since that’s what I used in the past and closest to what their sting method recommended. Well it was to big, it seemed like it was constantly moving around when I moved and ended up rubbing me raw. I had to fork over another 50+$ and wait another 2-3 weeks to get the new ring.

Spring was now here and life started getting busy for us so the adventure got put to the side. We did try out the new ring once it arrived but only for a week here, a week there kinda thing. The new 40mm ring was a better fit but still not as snug as the CB #3 ring. With the locking system on the Holy Trainer I couldn’t do my self lock ups, I’d be in deep crap if I touched Mistresses keys. Some times I’d go back to old faithful for a self lock up, if Mistress was happy with that she would let me switch over to the Holy Trainer and if not I’d be set free.

For the most part this is how things went for the next few years, no real challenges got set forward and no records broke. I quit working on the road and as a result Karma had Mistress working on the road more. Lock up would come into play than but at most maybe for 3 weeks, like I said no records broke so no real stories to tell. We did still play around with denial but not to any extremes some days Mistress would let me cum and some days not, it all depended on how she felt that day. As a result she became very skilled in the art of the tease. 

My next challenge

I had just taken a new job, still on the road but back to having set days off. Mistress was nice and still letting me be free after my last stretch of chastity, and we weren’t 100% sure of my accommodations. This new job was a camp job and I had been in camps before that didn’t have completely private bathrooms. I didn’t really want to be in the middle of washing my cage in a public bathroom when someone else could walk in at any minute.

This camp ended up being nicer than the ones I had been in before and had private washrooms just like you’d have at home or in a hotel. Knowing Mistress had something planned out I was a good boy and reported back to her that the accommodations would work out for me to be locked up. At the end of my days off we got me all fitted in my cage but this time Mistress wanted a plastic lock to go on and than sent the actual lock with me but no key.  I was to cut the plastic lock half way through my shift and get a good cleaning and than secure the actual lock for the remainder of my shift. Mistress required a picture after my shower to make sure I followed orders. I think the shift I was working at the time was 16 days on and than 5 days off.

This was something completely different for us. I had never been locked up before and that far away from the key, it was a whole new mental aspect of chastity for me. I don’t even know how to explain it, but it did get in my head for the first little bit.

When my days off rolled around Mistress would unlock me for a proper cleaning, sometimes she would let me be free for a tease and orgasms for her and sometimes she would lock me right back up again. The night before I had to go back to work I’d get another real cleaning and the plastic lock would go back on.

I always fish for hints of what Mistress is plotting but she is usually pretty secretive, but this time she gave me one little hint that she had a set number of days picked out for me and it would be longer than my last set. So all I really knew was it was going to be at least 30+ days. In the past Mistress was just gradually increasing things so I thought 40 maybe 45 days this time. Near the end of my second set of days off I was getting a bit excited, that was around the 40+ days and I thought for sure I would be set free and finally cured of my built up sexual frustration. But no just set free for a cleaning and and back into the cage with a plastic lock.

Being gone for 16 days at a time was fairly helpful in this situation, I didn’t get the amount of teasing I would of if I was at home. Mistress would make up for that on my days off and make sure she was building my frustration. Along with that she would sent naughty text messages and pictures while I was away to try her best to maintain that frustrations. The Holy Trainer version 2 had just hit the market around this time and it was getting great reviews so I thought it was finally time to upgrade from my old CB6000. I placed the order and the waiting game began again.

My next set of days were around the corner and the job was coming to an end, I padded the bank account pretty good on that job so I volunteered to take a lay off. I returned home 58 days locked and frustrated. The usual routine happened where I would get unlocked for a good cleaning but to my surprise it was right back in the cage for me. Not even a little free play time to stretch out. The teasing seemed to increase those first few days home compared to previous days off. On day 60 I was finally set free and granted permission to cum, it didn’t take too long. Once the cage was off and I knew it was time I was hard instantly and I don’t even think it took Mistress a minute of stroking before I erupted all over the place. This was one of my biggest orgasms volume wise but as far as strength wise I didn’t think so. I still greatly enjoyed it but I don’t think I fought it long enough to make it a great or the best orgasm. I later found out that Mistress had plans of giving teasing me and getting me to the edge several times before she was going to allow my orgasm, but she changed her mind due to the fact that I had already waited that long. This was now my longest stretch in both chastity and denial.

Getting back into things.

There has been several times over the years where life just gets busy and we fall out of the swing of things with our adventure. It is always difficult to try to get back to where we were, kind of like 2 steps forward one step back. We never really dove right into any of our new activities, more less dipped our toes in the water first than proceeded slowly.  This was a smart approach because neither of us got overwhelmed but it didn’t seem like we were making any headway.

I know it seems like we have been flying along but to give you a grasp of the time frame probably at least 2 years has past. Over that time when we were still using our browny points system I had purchased a few more devices. I bought a cheap full out chastity belt, I had to spend some time modifying it to get a good fit. I wanted a full belt for a deeper experience into chastity you could say and it did give me that, but it wasn’t very practical for everyday use. It limited my movements like bending over and I was always worried it was more noticeable. But it did make me feel more helpless about my situation. I also tried out the silicone device The Dick Cage. I wanted that because I thought  it would help with those pesky 4 a.m wake up calls. It did help with that and was more comfortable than the old CB 6000 but it too had its own flaws with rubbing and chafing. It also kept things warmer down there so I found it developing a smell faster.

It seemed like I was always defaulting back to old faithful my CB 6000. I had pretty good luck with it. I have read complaints about a lot of cages splitting but my never did. I noticed a crack one day but just super clued it up and gave it a light sand and it’s still holding in there. I did how ever break a ring on day, we were in the middle of a pretty good tease session when all of a sudden I got a good pinch. The ring broke where the pins go through the little holes on the side. This caused things to open up on one side but since the other 2 pins were still in place it didn’t open up enough to not cause pressure. Speaking of pressure , there must of been a lot of pressure in that cage at the time to make stuff break!

When ever I felt that our adventure was in a dry spell I will lock myself up. For the most part it gets us back on track but I later found out that Mistress kind of sees it as topping from the bottom. I see her point now but at the time I just thought I was being a good boy and doing it to avoid temptation. If she had other plans for her cock she could always unlock it and tell me to go wash up.  For the most part when ever I locked myself up it would last for a few days and than I would get released for play time and not have to go back in. Mistress noticed this pattern and taught me a lesson about assuming. She started throwing me curve balls and wouldn’t unlock me for play time or made sure I got locked back up again right after. One time she even made a comment on the regards of  “ Oh you just thought you’d lock yourself up and I’d let you out when I was horny”!

I’d usually do my self lock ups on my days off. The first few days I’m home after a long stretch of work on the road  we usually spend to ourselves catching up on play time.  So once I’ve had a few orgasms and Mistress goes to work I’d lock myself up. I’d have no problem being like that for the next few days and just servicing Mistress. Near the end of my days off  Mistress  would usually unlock me so we could have actual sex instead of the orgasms I was giving her in other ways the previous days.  It was time for me to get taught a lesson about assuming, Mistress didn’t unlock me this time and I had to go back to work locked and frustrated.

This particular job was only a few hours from home but it didn’t have set days off like usual, we were only getting Sundays off work. It had been a while since I had to go to work all locked up and with only one day off I didn’t know if it would be worth driving home for. At this point we were still letting me take a key on the road with me though, so I knew I would stay clean I just didn’t know when my next orgasm would be. Mistress came to visit me a few times on that job but if my memory is correct I don’t think she let me out to play.  In the end I think that was just over 30 days locked and denied. Mistress was proud of me but she had a new challenge for me coming up for me and as always she kept most of the details to herself.

Our system

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The next steps

As I stated earlier Mistress thought our new chastity cage was only going to be used as a toy. I think she was thinking she would put me in it and tease me and than take it off for play time. Well that has happened of course but it’s not like she was just locking me up for that purpose.

I was working on the road lots in those days so when I got days off they wouldn’t always be on Mistresses days off. She soon started to lock me up during the day while she was at work. She has made a point several times to make sure I knew it wasn’t a trust issue, she just likes having that extra assurance knowing I can’t touch or play with myself while she wasn’t around. I was usually unlocked in the evening once she got home from work and allowed to stay that way until the next morning. There was a few times in the beginning that I was a little stubborn to get out of bed to be locked up and one morning I just didn’t get out of bed before she left for work. That night she got home and went straight to the bedroom to get the cage. She made it clear that I was getting locked up for the night because I didn’t get out of bed that morning and I would still have to get up with her the next morning to make her coffee. Due to those rude 4 a.m wake up calls the cage likes to give me there was no problem getting out of bed the next morning.  She enjoyed the time we got to spend that morning and thinks coffee tastes better when I make it for her so it became a rule that I had to get out of bed with her in the morning. Along with that a bed time was set because I would usually stay up later than her on my days off and that is most likely why I was so stubborn to get out of bed some mornings. 

It now seemed that I was spending most of my days off in the cage. Some nights I would be let out and allowed  to stay free for the night if it was shower night or if Mistress wanted to play. Some nights I would get locked back up after my shower or play time. She had no consistency and that’s the way she likes it. To this day Mistress still loves the element of surprise and always keeps me guessing.  The one thing that wasn’t a surprise at that time was when she unlocked me for play time I always knew it would end in an orgasm for me. Denial was brought up since anything we researched about chastity usually had something to do with denial to go along with it. But Mistress didn’t show too much interest in denial at that point, she had always enjoyed giving me pleasure and was made to believe that giving blue balls was rude. 

I was the one to actually suggest we give denial a try.  I was still doing a lot of researching in those days to find answers for the problems one usually has when first getting into chastity, stuff like finding the right fit, how to avoid discomfort, ways to help stay clean. I had read a lot of information and most of it seemed to have chastity and orgasm denial go hand in hand.  Some people claim that chastity is pointless with out denial, that you need denial to properly train a submissive and other stuff like you have to keep them locked and denied for this certain amount of time. I had read so much information and some of it contradicts the other, I was overwhelmed by all this and didn’t know what to believe.

To me chastity is everyone’s own opinion. There is no right or wrong way to practice it, you don’t have to be wearing or even own a device to be chaste. In my own opinion it is all a mind set and the main reason I have and wear a device now is more of a symbol and a reminder than an actual tool to keep me chaste. But that’s just my opinion and everyone else is entitled to their own.

Any ways back to the story. I was overwhelmed with information and didn’t know what to believe so I took little bits of information from everything I had read and we made up our own system to make chastity and denial work for us and to build more on our female led relationship. We didn’t dive right into our system, we still had a few fine details to work out and most importantly we had to teach Mistress to say no.

We started off slow and took baby steps. On a weekend we would play in the morning, Mistress would get her pleasure and I would get attention too but no release. Later on that day or evening we would play again and we would both get pleasure. We would play again the next day and Mistress would tell me no again but this time make me wait a day before I got my release. We eventually worked our way up to me going a full week without an orgasm but playing almost every day , sometimes several times a day. Mistress was and is a very sexual female and has no problem having multiple orgasms so playing a few times a day was the normal for us on the weekends.  Mistress had learned that saying no was ok and blue balls really wasn’t as mean as what she was made to believe. I had got a taste of sexual frustration and also learned that blue balls really weren’t that bad. Now it was time to work out the last few details of our system. 

My first chastity device.

I guess my actual first chastity device was a pair of underwear that could be locked. They weren’t practical and I think they only got used a few times. We actually bought them before Mistress had even decided to lock up her cock, I say her cock because it no longer belongs to me even though it’s attached to me.

So we had the talk about getting a device now it’s time to pick one out.  We both sat down at the computer and looked at a website that had a selection of different styles to see what each other’s preferences were. Instantly Mistress pointed to one of those styles that not only goes on you but also in you, I was shocked instantly. Some how I managed to convince her to just finish looking at everything else before we make an actual decision on that one.  So many style to pick from, it didn’t take long to decide on a cage style vs belt style. Mainly due to cost and practicality. In the end we were overwhelmed by everything and Mistress just told me to pick one out since I was going to be the one wearing it, but she had the final say once I had it picked out.

The next day it was back to the computer for me to do some research and pick out a cage. It didn’t take long to learn that for a first time buyer you should pick something not to expensive and something that is adjustable. We had a good idea from the night before about price range so I knew what we were looking at spending, but I had no idea about custom devices and how much they can cost. Wow sky is the limit on the high end of the price range, but custom made isn’t adjustable so that was ruled out quickly.

In the end everything pointed to the CB lineup. The CB6000 was fairly fresh to the market and had good reviews at that time. I wrote down some notes on sizes and dimensions and waited until Mistress got home to show her what I had in mind and do some measuring.  She was happy with the device I picked out and we took some measurements, than double checked the measurements again and even triple checked them because we were getting variations due to excitement!  The measurements we got feel right in between the the regular and the small size so it was back to the drawing board. After more research I came to the conclusion that if it’s that close your better to be on the small side when deciding on cage length.  I would have to agree with that now after my years of experience, it may be more uncomfortable in times of excitement but it’s a lot easier to deal with when you’re trying to align things when your using the bathroom. My mind was made up and Mistress approved my decision, I placed my order and now the waiting game.

I was working away from home when the device arrived in the mail but Mistress wanted to look at it so she opening it up. When I came home for my days off I finally got to see my first real chastity device. We played around with the many pieces but didn’t actually try it out that night. Over the course of my week off I tried different combinations of rings and spacers to find the right fit. With in a few days I thought I had it figured it out so it was time to try my first overnighter. Mistress was nice and left the keys out in the open for the whole trial period in case I felt I needed to make adjustments or needed out. I’m not going to lie I went for the keys that very first night when I got my first rude awakening in the middle of the night. Over the next few days I got use to it ( well as use to it as possible) and Mistress took ownership of the keys. I had to go back to work a few days after that so Mistress unlocked me from my plastic prison and we tucked the cage back in its case nut Mistress made sure to put one of the keys on her necklace.

How it all started

It all started back when the wife (girl friend at the time) and I were young, I can’t even remember how many years ago it was but if I had to guess I’d say at least 8.  We lived in a really small town with no tv so to pass most of our time we spent a lot of time in the bedroom. We both had/have fairly open minds so we weren’t scared to try new and exciting things in bed.

It all started with light bondage, we would take turns being tied up or using fuzzy hand cuffs. It didn’t take long for me to realize I really enjoyed being the one to give up control. I would be restrained and she would have her way with me. It usually resulted in a long tease as fore play than end with an orgasm in some form.

From there I turned to the internet and soon found out about femdom/ FLR. I knew about dominatrix before but not femdom. Reading about that and the activities that came along with it really perked my interests. I figured hey I’ll give up more control outside the of the bedroom if it gives me more of what I like inside the bedroom.  I shared my new found knowledge with her and she agreed to become my mistress or Ma’am to me now.

A few simple small rules were made to start with like properly addressing her as Ma’am, helping out around the house more often, asking permission for certain thing  and her most important rule was no more taking care of my own sexual wants.  The last rule was a big change for me, I had been doing that since I was a teen so it was going to be a hard habit to kick.  Looking back now I did play with myself way too much and there was times it resulted in Mistress being robbed out of play time because I had already taken care of my wants earlier that day. She had now taken over my pleasures but chastity wasn’t into play yet.

As our adventure (that is what we called it) continued I would spend more time on the internet researching and that’s when I learned about chastity. I use the term learned  loosely, sure I knew what the meaning of chastity was but I thought chastity belts were a mid evil thing. I had noticed it mentioned in my previous internet searches of femdom but didn’t realize it was practiced  to that extent.  I soon discovered that chastity belts were still around, along with chastity cages in several different styles.

At first I was in shock that these devices were around and actually being used, I thought who in their right mind would agree to wear one of those. But the more I read and researched the more I became intrigued. Thoughts of giving up the control over my own manhood soon excited me. I was curious on what it would feel like to wear one of those devices.

Well Mistress already laid down the no playing with myself rule along with no touch it either if I wasn’t in the bathroom so I began to plant the seed in her head of chastity. I’d say stuff like “well you can’t physically stop me from touching it”. I know topping from the bottom right but I didn’t want her to know I wanted it at the time. The whole femdom thing was new to us and I didn’t want to seem like I was pushing to new boundaries too fast, she might of thought I was a total freak and gave up on the adventure. So after a week or two of dropping seeds into her head when the opportunities seemed right she finally said “yes I can, it’s called a chastity device”.  She had been doing some research too on femdom actives. We had a talk about it and both agreed that it wouldn’t hurt to try out and “ play” around with chastity and it would probably be for her best to help get her use to her new dominant role. Mistress figured it would be more of a toy that got played with from time to time, jokes on me it didn’t take long for her to realize it was actually tool for her not a toy!

Quick Intro

Hello future readers and welcome to my blog!

As the title says this blog will be about chastity mainly and other adventures that go along with it. I am a new blogger so please be patient with me!

I’ve been playing with chastity for several years now on and off again basis. The longest I’ve been in a device is 3 months with weekly releases for cleaning and play time during that stretch. The longest I’ve went in chastity and without orgasm is 60 days. I say “playing with chastity” because we go in stages of using/enforcing it and than it gets put in the drawer to collect dust for months. I am currently locked up and have been since November 12, and my last orgasm was November 19.

My loving wife likes the element of surprise so I have no clue how long I will stay this way, she likes to keep me on my toes that way. I usually plan for the worst, so in this case it would be record breaking which would be at least 2 months. I find it helps mentally if I plan for the worst and than it’s a nice treat when she lets me out before than.

I tend to treat chastity and denial as a challenge more than she does, I like to set new records and push to new limits.

In this blog I plan to cover my thoughts and views of chastity and denial and also track some of my future adventures. I will most likely go back and cover how this adventure all started and share some of my past experiences too.

Well that’s all I have time for right now but I look forward to writing again soon.