The Question

This is a semi autobiographical piece with some fantasy fiction thrown in. Probably a slow build but hinting at how a slave is conditioned over time and how their experiences in life lead them to where they want to go.

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My name is Dave Matthews (yes like the band). I'm a nearly 40 year old finance professional. As the name suggest, in many ways I'm a rather plain, boring straight white male. I'm also currently facing a dilemma. Do I want my chastity device to be unlocked and receive an orgasm for the first time in... well I don't actually remember how long, or do I want to receive 10 strokes of Goddess Amber's new cane? I know what you're thinking, that's such an easy decision, only an idiot would choose the pain over the pleasure, especially one so long denied. This is particularly true since I'm no masochist, in fact I really hate pain. I have a really low pain threshold and Goddess Amber knows it. So why is it even a debate? Maybe I need to explain a little about how I got here...

I could go back to when I met Goddess Amber, but I think I need to go back even further, let's start at the beginning. I was a pretty smart kid, top of my class in a few subjects, in the top set for the others. I was used to getting praise. I got it with fair regularity and the three times I got in trouble in my childhood stand out as the worst three moments of my youth. Things continued that way in sixth form, I chose subjects that were my strengths and I was very good at them. There were a couple of "competitors", but it was friendly rivalry where we all excelled and were congratulated similarly.

It was in sixth-form I had my first serious girlfriend with regular sexual relationship. Looking back now I realise how this is how my conditioning started. She wasn't a Domme, or even dominant, but she did believe that when you were in a sexual relationship masturbating and watching porn was as bad as cheating - you should be saving your sexual energy for one another. We were having sex a couple of times a week, so even though I had a high teenage sex drive I didn't mind so much as sex is clearly masturbation. It did mean that I was a rare breed, an 18 year old not masturbating, but I was happy.

Eventually though University rolled round. Like most teenage relationships that didn't work out, we went to universities on different sides of the country and long distance (particularly long distance and not masturbating at 19) doesn't tend to work out! Overall I felt a little lost, I'd gone from being a big fish in a small pond to a small fish in a giant ocean. I was still smart - I was at a good university doing a course that had a low acceptance rate, but I was by no means the smartest. My marks were middling at best and deteriorated through the 3 years as I lost confidence. Looking back now I see the main thing that was missing was that constant praise, adulation etc from doing good work. Nobody congratulates you when you're getting 62% on a university assignment, that's the standard you should be getting.

At the same time, free from the restraint of my pornphobic ex, and struggling to find regular sexual partners to replace her I fell into a spiral of constant porn/jerking, at least once a day, twice a day most of the time. It was all very empty. I felt a bit lost. After a time the only porn I enjoyed was ones showing powerful women. My experience with my ex meant I had enjoyed the restrictions placed on me, and it seemed that was something I was looking to replicate. However in my personal life I couldn't find that, the women either just wanted a one night stand and to move on or were the passive kind that were looking for the man to take control. In all University was not the best time of my life.

After University I needed a change. I found a job quite quickly in a different city, and did quite well at it. Another guy who started the same time as me was asked to leave after a couple of months and I was given a promotion. It felt good, like I was getting back to me again, being told I was doing well. I also found another girlfriend. Initially I thought she was going to be exactly what I wanted, she was certainly kinky claiming to be a switch, had a small collection of toys and loved sex. We went along nicely for a year or so, handcuffs, blindfolds etc being used more often than not. The romantic looking into each other's eyes as you orgasm hardly ever happened for us as usually one of us couldn't see! We experimented what felt at the time like a lot, risky sex, how long we could keep a tied partner on the edge for. I once spent three hours restrained, blindfolded and almost constantly erect - that ended with an explosive orgasm - but disappointing 30 seconds sex for her!

The longer we went however, the more it became apparent that she was actually a sub pretending to be a switch to make me happy too. That of course made neither of us happy as I couldn't dominate her the way she wanted, and she couldn't do the same to me. Towards the end of our relationship I found out she'd been sleeping with someone else - someone who was dominant. It's hard to express the feelings I experienced working that out. Humiliation, shame, betrayal and intense arousal. That fact the person who claimed to want to be with me to my face also wanted to fuck someone else was something I found so insanely erotic which I totally hadn't expected. I think the day I found out (without telling her I knew) we had the best penetrative sex I've ever had, so intense and passionate.

Unfortunately though, she was by nature submissive. When we eventually did talk about the fact she was 'having an affair' and it didn't work out how I hoped. She had no interest in (what I found out was called) the cuckolding lifestyle. The excitement of doing it behind my back was essentially what had kept her with me - she ended up choosing the other guy over me.

With my new found singleness I made the decision then that I was going to explore the desires that had crept into my life over the past 5 years or so. I bought my first chastity device and started interacting with professional Dommes online. I loved it, the thrill of being told how long to lock up for and when I was allowed to orgasm. Obviously I paid for some of these interactions but it was always reasonable. I kept trying to meet a dominant person to try and have a normal (but kinky) relationship with but that didn't ever seem likely, there seemed to be a large number of men after that same thing and only the occasional woman. I was also doing fairly well in my career and didn't want anything to jeopardise that so I probably wasn't as open about my desires as I would have liked.

It would go in cycles though, I'd spend periods of a month or two perpetually locked, unlocking to tease and occasionally cum then locking back up. Then I'd go through other periods of shame, feeling embarrassed about the kinks. This usually came after spending time with family who'd spend most of the time talking about family and grandchildren etc. That shame would cause me to deny my kinks, hide away my device, and try and be normal.

One day something strange happened. I received a package, addressed to a woman I'd never met but my address. Since I had no way to know where the package should go, I opened it. Inside were two outfits from Anne Summers. One was a French maid's outfit, the other a Nun's outfit. Presumably two women were planning on a kinky night out... Curiosity got the better of me, I couldn't help but try them on. The nun's outfit was too small, but the maid fit perfectly.

I had never thought about feminisation before, it really didn't appeal. Now I actually had an outfit though I couldn't stop thinking of it sitting at the bottom of my draw. I found myself taking it out regularly and just looking at it. After a while it became my Sunday routine, don the maid's dress and do my cleaning. I found myself falling deeper into the submissive life, so much so that I finally decided to see a Dominatrix.

I bought the first session for myself as a treat for my 30th birthday (30 already? Where had the time gone?! I must have skipped a few uneventful years somewhere along the line!) In order to earn it this expensive treat for myself, I locked on my chastity cage for 100 days. I was so committed to this that I turned down a potential one night stand with a 19 year old about 80 nights in to the stint. I was looking forward to it so much, and so nervous, I booked an entire day off work for it. As it turned out, the Domme cancelled on me on the day of my appointment, rearranging for three days later. Those extra three days were agony - I hadn't mentally prepared for them. Although I wasn't expecting an orgasm during the session (I thought it could be possible but didn't want to count my chickens, I was expecting to orgasm thinking about it afterwards!) Speaking to her afterwards she had thought the 100 days denied was just talk and was feeling hungover so didn't fancy meeting a new client! Still, on day 103 I turned up to her place, so so so scared, shaking like a leaf! I may have mentioned, I was terrified of pain and I had no idea what was going to happen.

I still remember parts of the session as if it was yesterday. She was beautiful, wearing a short black leather dress and knee high boots. First she calmed me down and had me talk through again the things I liked and disliked, these had been covered in our messages but apparently she likes to hear her subs talk about them beforehand too. She asked pertinent questions and assured me that although she might test me she wouldn't hurt me more than I could handle. Then she had me step into a next door bathroom, remove my clothes and come back in naked. At that point I handed her a key to my device which she instructed me to keep on. Walking back into the room was so nerve-wracking. I'd not shown myself in my cage to anyone before (except anonymous online photos). Now I was completely exposed and vulnerable, I was amazed at just how much I liked that feeling - being so completely out of control and dependent on someone else.

The next hour saw me spend most of my time restrained, often in more physical pain than I have been any other point in my life, but never more than I could actually take. There was also a lot of teasing. Eventually the device came off, and more pain was applied to my genital area. The question was asked a few times wouldn't I rather be safe in my chastity device? At one point a combination of teasing towards orgasm and pain had me almost begging to be locked safely back away. The session ended though with the most explosive orgasm I'd ever had. My cum was literally half way up the wall of her studio, it was one of the best experiences of my life. What made it most special for me was that after being denied for so long I had finally been granted permission and the Domme made me feel like I had earned it.

The whole experience was addictive, the next time I saw her a month later I left both of my keys in her hands. The device I was wearing at the time was silicone so I knew that if I ever wanted to I could easily escape, however I'd never get it back on again so she would know. Basically we both knew that this made it in effect a game we were playing, but I was determined to play it properly. Over the next 6 months or so I had some of the best times of my life. She took me to a fetish night, had me strip naked and practice her paddles on me (she went easy on me but it was still a lot to take). The crazy part about it was I took my clothes off without realising there were about 20 fully clothed people watching me strip down to a chastity device. (There were a couple of other naked subs in the room).

She also pushed my femininity, regularly dressing me as her maid. I sessioned with her about once a month, mainly focusing on tease (she only granted me one release in those 6 months or so she had my key). The best part for me though was we became friends. She'd message me sometimes after finishing sessions asking if I wanted to go for dinner, and we'd talk about totally normal things. Of course I'd pick up the cheque and she'd call me a good boy, but other than that there were many interactions where we were just two people hanging out. She didn't live in the same town as me and once after dinner and drinks she even slept at my place, in my double bed, as I slept on the floor, locked in my chastity cage of course. Once she was under the covers she removed all of my clothes telling me I was forbidden to look. That was the only time she was naked in my presence when I wasn't restrained, it was torturous and I didn't sleep a wink! It was one of the happiest times in my life. I felt like I'd found myself and that the 30s were going to be my best years... then my Dad died.

At the funeral I was bombarded by the normal questions, girlfriends, when I'd get married etc. I couldn't take it anymore. I felt so ashamed that I wasn't living the life others wanted. At the same time I'd met a vanilla person who I was getting on really well with. When I returned from the funeral I sat down with my Dominatrix and had an honest conversation. Afterwards I left with my key and a sadness in my heart. As far as vanilla relationships go, I then started probably my best. I really tried hard to make it work, despite the flaws. There was one problem though, sex. She was so passive, never wanting to initiate, I was me. Then when we did attempt things, my cocklet wouldn't always work. I could be hard as a rock looking at FemDom porn in the bathroom, but a moment later faced with a nice girl who wanted sex I'd often be limp. In the last two years of our four year relationship we managed sex five times.

Despite a proposal and subsequent wedding planning (or maybe because of it) the relationship was doomed. It left me in my mid 30s and at the lowest point of my life. We had moved to a brand new city for her work, I was now in a job that was harder but paying less money than before and I knew hardly anyone. I felt empty and directionless. So I did the only thing that felt natural to me, I locked back up. I stayed that way for about 9 months. Unlocking occasionally for release, constantly trying to find a dynamic similar to the one I had before. I was struggling though. Although I came across some fantastic ladies, none were quite what I was looking for. That was when I found Goddess Amber.

If you've stuck with me this long thank you, we've finally reached my reason for living and my current dilemma! Like I said I was struggling to find a Domme that I clicked with. I tried almost every site. Somehow I ended up on a FinDom site. I was always aware that to meet a good Domme it was likely to cost me money, but I hadn't really planned on aiming for a specific FinDom. I loved the site though, every Domme was cam verified so you knew they were real - you didn't have to wade through a sea of fakes to figure out who was real. Another reason I liked the site, there was no nudity. This may seem at odds to what I've said earlier, but I much prefer my basic porn to have females clothed. I like them in positions of power and always having that upper hand leaving the men vulnerable.

Don't get me wrong, I love to see a powerful woman naked too - but only when they've chosen for me, specifically me to see it. That way it feels like a reward, a real treat that I'm only receiving because I've been dedicated to them, when it's out there for anyone to see if feels somehow less special. This probably stemmed from my first girlfriend, and how the few times I failed with the masturbating it wasn't to naked women but still slightly clothed women and then how abstaining from seeing other women naked was why I was able to see her when no one else could. I think it also fed in to my developing cuckold desires, knowing that other men would be seeing these women naked but not me, I'd only get to through parting with my money and them deciding that they wanted to tease me with it.

I had been active on the site for a few weeks, spoken to and tribute a couple of Dommes, but still not found exactly what I was looking for. Then Goddess Amber joined the site. I was hooked from her first profile picture, she looked perfect. Her deep brown eyes, full red lips and long brown hair captivated me - plus I've always loved seeing a facial piercing! My first interaction was the best I'd come across too. Normally I had found the Dommes far too eager to try to get you to part with your money. Goddess Amber however said she wanted me to want to give her money, not just take it.

At the time I had been without orgasm for around seventy days, just talking to her made my self-imposed denial significantly harder, I just wanted to impress her. Obviously I sent her an initial tribute. Following that she imposed a further 100 days of chastity on me and then over the coming years proceeded to take everything from me. On my first payday she took 20%, if I thought that was all for the month I was wrong. It took her just over a week to convince me that my keys were safer with her. By now I was wearing a nub sized resin cage - it was so small my cocklet might as well not exist! It was also far more secure, I couldn't pull out and I couldn't destroy it. For the first time in my life I was truly trapped and really had given all of my power to a women who I hadn't even met in person. At one point I mentioned my fear that wearing it for too long I might become impotent (building on the issues I'd had in my last relationship), at which point she told me that that was the ideal scenario.

Overall I just thought she was something else, she exuded confidence and natural dominance and pushed all of the right buttons with me. I was tasked with sissifying myself more and more, it wasn't long before I was wearing panties every day. She also spoke to me in exactly the right way, testing me but realising that what I needed most was that encouragement, to do better and to be congratulated. My whole world became consumed with wanting her to say "Well done pet", "Good girl" or some derivation thereof. Her decision to "own me" gave me more pride than any of my personal achievements over the years, my orgasms and money were such a small price to pay for that.

She was true to her word though. A few days before my initial 100 days were up I received a package in the mail with clear writing to not open before my release date. Three days I had to wait. You have no idea just how long three days is until you have to show self-restraint over something you want so much and now this was twice I'd really suffered through a three day period. When the hour arrived I felt like I couldn't wait any longer, I might burst out of my skin. I sent Goddess Amber my release fee ripped open the package and out fell a pair of the sexiest red lace panties I'd ever seen, a picture of my Goddess wearing them and a key to my device. I had worried she was going to tease me or torture me more and not give me the release long promised, but that was not the case. Finally after 6 years or so I finally recaptured that feeling I'd had when I first visited a Dominatrix. With my Goddess's scent in my nostrils I exploded like I'd never done before. Afterwards I was in such bliss that you'd think I'd just had a shot of heroin or something! As ordered however the key was back in the mail to my Goddess that same day. That afternoon she set me a long list of tasks to do to ensure I didn't suffer from the sub drop and remembered my place. That was my last scheduled orgasm. After that Goddess took to heart my belief that a sub's orgasms should follow the four Rs, they should be Rare (hence the chastity), Random (when they do happen they shouldn't be expecting them, otherwise they might develop expectation/entitlement) and when they do have an orgasm they should be Regularly Ruined (to make sure they never forget who is in charge and has that power over them - what can be given can easily be taken away again).