Ch. 04 - Chastity Begins

Tasting my own cum and sucking on my own cock was similar to the puberty experience. A whole new world had just opened before my eyes and my rabbit hole was no longer a hole but a large vortex which I had been just sucked right into. Thus began a new chapter for me, no longer was it just a fascination with crossdressing and wearing sexy girls underwear, I was now immersed in sissy hypnosis videos which showed sissies worshiping and sucking on large black cocks while wearing chastity devices making them look very emasculated.

This new passion however came with a few challenges: the first one being that I managed to shave every bit of hair off below my neck (except for my arms and a nice girly landing strip right above my boy clitty) when my wife Bonnie was gone on a girl's weekend away. I was intoxicated when I did it and I was now struggling to figure out how to explain it to her without raising too much concern. After thinking about it for a bit, I decided to tell Bonnie that my socks were constantly pulling on my leg hair so I decided to shave that part of my leg. Then, once I had shaved the bottom half of my legs, it looked dumb so I decided to shave my legs entirely.

Bonnie seemed to be ok with my explanation and even offered me some nice lotion for my legs. As for the landing strip, I couldn't really explain that but seeing that we had our once-a-month sex just before her girls weekend, I was cautiously optimistic that I could hide the landing strip until it grew out -- also we usually have sex in the dark so I could probably get away with it if for some reason the world changed and we had sex sooner. Until my landing strip started to disappear, I carefully made sure to shower when Bonnie was either sleeping or when she wasn't around and, as for sex, this time around it was more like 8 weeks until we had sex again so there was no issue.

In addition to our very infrequent sex, Bonnie rarely looked at my cock, which is less than 5 inches fully erect, and Bonnie really only wanted sex for her own orgasm which meant that sometimes I would just play with her clit and once Bonnie orgasmed, she was done. Bonnie often complained when I put my cock in her; as a result, when I did use my cock on Bonnie, I had to be very careful and lube her up otherwise she said it was uncomfortable and would ask me if I was done yet when I was just getting started. As it turns out, our sex session was simply Bonnie laying on her tummy while I played with her clit with one hand until she orgasmed, while I put my index finger in my boi pussy with some lube to help me get to a climax. When I did climax on Bonnie's back, I graciously helped clean it up with tissue and, unseen to Bonnie, I managed to put most of it in my mouth.

As weeks passed and became months of sissy hypnosis, I found that I began to desire to have my own chastity device -- maybe it was the constant reinforcement of sissy hypnosis telling me that I needed one but, regardless of that, I needed a chastity device. Knowing that I didn't have the nerve to go into an adult shop and buy a chastity device and the local Walmart doesn't sell adult toys, my shopping experience was forced to evolve to online shopping. This presented two new challenges for me, how do I discreetly pay for my online purchases and how / where do they get delivered? If I could figure that out, the world would be my oyster -- so to speak.

My first thought for purchasing online was to apply for a new credit card account. I began my research and started the application process online only to rethink it all when they started asking for name, address, credit history and bank account information -- Bonnie would be sure to find out sooner or later if I provided all that information and how would I possibly intercept all the mail? Besides that, I wanted my purchases to be as anonymous as possible. So, after a little more looking I found that, with cash, I could buy a prepaid vanilla debit/credit card that I could use online for purchases. So, I began pulling a little bit extra spending money out at the ATM over the course of several weeks and bought my first $100 on a prepaid debit/credit card.

The second problem was how to get my online purchases delivered without my wife Bonnie finding out -- she is always buying online and is the first to open the mail and packages without paying attention to who they were for -- 90% of the time they are for her anyway. Bonnie was practically on a first name basis with every delivery person. As a matter of fact she often tips the drivers -- the regularly scheduled drivers always ring the doorbell when they deliver packages and wait for her. I questioned her about it once asking why she was tipping them and she said it was because it avoided the risk of someone stealing them from our doorstep -- with all the theft happening of deliveries.

I still am a little wary of Bonnie's tipping of the delivery drivers, so once in a while I snoop on her using the video doorbell app while I am at work. Most of the time the delivery driver waits for Bonnie to answer the door and being very friendly, she will often invite the driver in and then offer him a tip and a drink of water or use of the bathroom. I have noticed that Bonnie is a bit sexist though because she never offers women delivery drivers tips -- I haven't brought it up because the majority of the drivers are men and the only time I have seen women delivery drivers is when I am snooping on the video doorbell app so if I mentioned it Bonnie would clue in to the fact that I was snooping.

With home not being an option for deliveries, I researched getting a PO box at the store but I was back to the problem of how I would pay for it -- they don't accept cash debit cards for recurring billing and I also did not want to provide them with my home address for billing purposes. This left me with the idea of getting my purchases delivered to my work address, with my name on the label so that reception would direct it to me. With payment and delivery figured out, I went online and started shopping chastity cages.

My first search online for a chastity cage came back with over 50,000 different cages, I couldn't believe it! The options included different materials (plastic, silicone and metal), different colors, lengths and styles. As I browsed through many pages of chastity cages I couldn't believe how incredibly aroused I became from the excitement of shopping for a chastity cage -- my little clitty was leaking precum almost like a faucet. Just as I had seen sissies do so many times in the hypnosis videos, except this time it was me, I reached down into my panties and started using my fingers to wipe off the precum and put it in my mouth -- I even had enough precum to wet my lips just like I been told to do in the sissy hypnosis videos. I can honestly say that from the first day I tasted my precum I was hooked. For some reason, I seem to favor the taste of precum over cum but the texture of a big glob of cum is second to none when it is in my mouth.

With so many chastity cage options, I finally decided on a pink silicone style chastity cage with a single padlock in the center which I thought looked comfortable and pink was quickly becoming my favorite color. I must have sat on the computer screen for 20 minutes deciding whether or not to hit the pay button for my first chastity cage as it represented another milestone in my journey. In the back of my mind, this purchase was sort of a point of no return -- if this worked out I could foresee endless possibilities. With a final push of the pay button, it was done -- I had bought my first chastity cage (with many more to come).

Waiting for the delivery of my first chastity was painful (I wanted it so bad) and, of course, the order took a full week to arrive. I'm sure the receptionist at my work must have been annoyed with me when I checked in with her multiple times about a package I was waiting for. Finally, have asked four times and a day later than what the tracking information said, the receptionist handed me my package which, to my dismay, was not in a box but a cheap plastic shipping bag and, although you couldn't see the contents of the bag, you could easily feel the contents of the bag. So I left wondering if the receptionist had any clue about the contents of the package that she had just handed me. This also served as a good lesson for me to ensure that all my future purchases stated that they came in discreet packaging.

As I opened the package with the chastity cage, I felt like a little kid at Christmas time. I had never put on a chastity cage before so it must have taken me 20 minutes to figure out how to stuff my penis head into the appropriate part of the cage and how to get the ring around my balls. It seemed that there was no way that I could fit even my smaller-sized penis (or clitty) into this thing. As it turns out my excitement (sexual arousal) was a good part of the problem; once I settled down and my clitty shrank a bit, I found that using some hand soap on my clitty and inside the cage helped tremendously.

Finally, with my balls now locked in the ring and my clitty in its place, I managed to put the lock through the locking hole and I clicked the lock shut. Clicking that little lock was also a trigger for me, as my mind immediately began to wonder what it would be like not to have control of the lock or what would happen if I lost the lock. This birthed many new thought lines which played out as sexual fantasies in my mind -- I couldn't help wishing that Bonnie could somehow embrace this and join my journey. However, in my heart of hearts I knew this would never happen.

With my clitty now locked away in my pink chastity cage, tucked neatly in my panties, I thoroughly enjoyed the feeling and continued on with my work day. Being Friday, it wasn't long after I put on the chastity cage that I had to run to our mandatory all hands team meeting on the other side of our work campus. Our all hands meeting was an hour long and, being an all hands meeting, it was held in our largest meeting room. Due to my extra-curricular activities, related to my new chastity device, I arrived a touch late and, as a result, I had to sit near the front of the room in view of most everyone.

I think I was only about 15 or 20 minutes into the meeting when the pain started to hit me. I had used the smallest ring for my balls and once the pain started, it continued to grow until my balls were numb but even though my balls went numb, I still had a lot of pain from the ring. In fact, the pain was so intense that I started to sweat pretty intensely and finally when the hour was up I raced to the nearest men's room -- I don't think I would have been able to make it back to my office, which was on the other side of the office complex, without collapsing from the pain. The pain was almost crippling and so intense that I could not wait until the men's room was empty so I just raced into the first empty stall, pulled down my pants, my pantyhose and panties so that I could unlock the chastity device.

With sweat dripping off my forehead, I pulled the keys out of my pants pocket and fumbled to unlock the tiny padlock whereupon it fell on the floor and bounced toward the occupied stall next to me. As it fell I said "Oops" which in retrospect was really dumb but I definitely was nervous and in a ton of pain so the words just came out automatically. The tiny padlock landed close to the next stall but still on my side so I was able to reach down and get it but I think I recognized the shoes in the stall next to me as those of Phil -- a side effect of all my crossdressing and shopping was that I had begun paying very detailed attention what shoes people wear -- most sissies wear sexy high heels, not Vans like the shoes in the next stall. Phil, was a manager in our Quality Assurance department who I infrequently worked with but I noticed always wore a pair of black Vans.

Having successfully removed the chastity device, the pain started to subside fairly quickly; however, I was now worried about whether Phil saw the padlock and if he knew who it was in the stall next to him. To avoid letting him know who it was beside him, I immediately pulled up my panties, pantyhose and jeans, flushed the toilet and rushed out of the bathroom so he couldn't sneak a peek through the wall of the stall as he walked by. When I got back to my office, I couldn't help myself and I felt like I needed to put the chastity cage back on. The chastity cage came with 4 different sized rings so I moved up one size to the second smallest and tried again -- I'm not sure why I didn't go to the largest ring after that incident. The only logical reason is that my sissy mind was now of the opinion that my balls were useless and that restricting them as much as possible might reduce my testosterone production which seemed counter-productive to my sissy desires.

When Friday was done, I decided to leave the chastity cage at work for the weekend in my normal hiding spot with all my other goodies, which was in a bag sitting on top of the ceiling tiles in my office which I could get to by standing on my desk and lifting the adjacent ceiling tile. The weekend was pretty usual, I managed to wear my panties throughout the weekend and even to bed with my pj bottoms on -- a little risky but also somewhat exciting with Bonnie not knowing while she slept next to me. After I finished my Saturday chores of cleaning the toilets, vacuuming and taking out the garbage, Bonnie said I had done a good job but asked if I would change the sheets in the guest bedroom as she headed off the master bedroom to take a nap.

Figuring that would be my only opportunity to suck my own cock, I put on my earbuds and watched sissy hypnosis until I knew she was sleeping. After 45 minutes or so of sissy hypnosis, I checked and heard her quietly snoring in the bedroom so I quickly made my way to the guest bedroom for my personal cock sucking session. I proceeded to lay on the bed, put my legs up and bending my lower body towards the headboard, working my cock towards my mouth. To help my boi clitty grow a bit, I lubed up my middle finger and my boi pussy with saliva. I inserted my middle finger into my boi pussy and began working it in and out as I continued to bend and stretch until the head of my, now slightly larger cock, was against my mouth with precum oozing out onto my lips. Once I had stretched enough that my cock was touching my lips I again was able to use my feet on the headboard to create a motion where my cock head would enter and exit my mouth. When I came, I made sure my cock was out of my mouth and targeted my eyes and forehead for a nice selfie of my sissy face covered in cum. Once I took a picture I retrieved as much of the cum as I could using my fingers and sucking them clean with my mouth.

The next week, my suspicions of Phil knowing it was me in the stall next to him on Friday were pretty much confirmed. As it happened, I had no meetings scheduled Monday morning so, with my office door closed, I had taken my jeans completely off and I had put on my short burgundy skirt and black pantyhose with my jeans on the floor under my desk. I was in the middle of taking a selfie of myself from my waist down so I could see how the skirt and pantyhose looked (I was becoming addicted to taking pictures of myself) when I heard a knock on the door.

Needless to say I freaked out because I wasn't behind my desk as I usually am when I don't have pants on. Alarmed at the thought of being caught wearing a skirt at work, I didn't respond to the knock and raced to my desk. I was literally in the motion of sitting down just as Phil opened my office door after knocking. I'm sure it was a little suspicious that I was sitting down as he was coming in, rather than getting up to greet him. Phil proceeded to ask me if I was ok because he noticed that I didn't look well on Friday during our all hands meeting. As I started to respond to Phil to tell him that I had not been feeling well on Friday, I could feel my face turn beet red as the blood rushed to my ears and they literally became hot.

It was a little intimidating looking up to him and talking as I stayed seated to hide the fact that I was wearing a skirt -- I was pretty sure he could not see my skirt because the front of the desk was not open. While Phil was standing up on the other side of my desk looking down at me I saw Phil's eyes on my phone which was sitting face up with my waist-down selfie showing on it. In my rush to sit down before the door opened, I had left my phone sitting on my desk with my selfie showing. "Nice legs!", Phil uttered. I quickly grabbed the phone and hit the home button and said sorry, my wife sent me a picture. Phil smiled but didn't say a word about it as he turned and left my office, stopping at the door to say "I hope you feel better Joe! Sorry for barging in on you. Would you like me to close the door for you?" I didn't even think about the fact that the picture he saw was clearly taken from within my office given the white board in the background with the wording "May your coffee be strong and your Mondays be short." which I had written just that morning.

As a side note, I can honestly say that I could literally tell that my brain was beginning to function differently -- I was dumber now than I used to be, I would never have done anything like that before I had started embracing sissy hypnosis and acting on what I was watching. A normal person who was almost caught in a skirt at work by a co-worker would stop, I didn't.

My next chapter of sissydom was going to be dildos and sissygasms which I had already begun my research on.