The ongoing story of my relationship with chastity and kink.

The idea of this thread is two fold: if I'm going to post here then people will have an idea of my story and we're I'm coming from, and, simply writing out my story will probably be therapeutic for me. That's always a good thing.

I won't go through everything at once, not that there's a whole lot, but I'll let it out in phases so I can reflect on things as best as I can and remember what they mean for who I am today.

Like pretty much everyone who's into alternative sexual lifestyles, everything dates back to my childhood. I came of age in the 90s, and was the most proficient computer user in my house when the Internet was becoming a regular thing. I knew things were different for me in the 5th or 6th grade when I discovered Internet porn and then discovered that I got the most response from the FemDom themed pages. Like I said, I'm sure that's a true story for anyone my age with my kinks.

But it was all just jerk off fantasy for me until about 2006 when I was turning 21. I didn't get to dive head first into anything, but I met someone online at a completely non sexual web forum that I fell in love with. We hit it off and it became clear that she was into things that were a little different as well. In the end it wasn't what I was looking for, but it certainly opened my mind to what the possibilities could be if I was simply more honest with myself.

More to come about her in my next post.

 

If anyone is reading this and has any questions as I go along feel free to ask.

In the fall of 2006 I had just turned 21. I was posting a lot on a very active web forum. There was a thread that acted like a chat room. It was thousands of pages long and dozens were added each day. It was a tight knit community that encouraged wise assery and clever conversation. I was new and introducing myself on a nightly basis, becoming a regular. I posted a picture of myself and a girl replied "I'd like to put make up on you".

Now, I don't consider myself a sissy. I never really have, but if if you only knew my kinks on the surface with knowing nothing about me you might erroneously put me into that box. Androgyny is a huge turn on for me, and I have a fetish for lingerie and heels, and if a dominant woman wants to dress me in femme I'm more than happy to oblige. But the label sissy seems to carry a lot more with it, in that it's a label that seems to dominate all others. IF you're a sissy you have a need to always be feminine, to adopt that role and keep it. To me, pushing the gender roles is just another part of the power exchange.

When she said that to me it started moving my gears. Was this something she said to be funny, or was it a glimpse into something more? Either way she had my attention. We started talking provately, more and more every day. We didn't divulge our kinks specifically, but through our talks it became clear that both of us were open to the idea of being very adventurous with our sexuality. We clicked on a lot of levels, and soon fell in love. The main problem was she lived as far away as anyone could. I mean that literally. There are very few points on the globe that are further away from me as where she was.

But I was young and naive, and she, though a few years older than me, was the same. So despite the relationship being star crossed from the start, we kept it up. We fell in love, though a face to face meeting would require some commitment and a lot of work and money. But we kept at it, talking all the time. She would tease me sexually, expressing her hunger to be dominant in the bedroom (though always equal out of it, she would remind me). But from the start I knew she wasn't purely dominant. We would have phone sex, and cyber sex, and maybe 20% of the time she'd want me to take a dominant role. That was fine, we were exploring. I wanted nothing more than to just submit, but I still felt it good to just explore all sorts of different things. I was a virgin at the time, and was finding out who I was.

We were exchanging pictures of each other, in all sorts of compromising poses. And one weekend she went away for a shopping holiday. When she came back she told me she bought me a present, and was sending it to me in the mail. She said when it came she couldn't wait for me to send back pictures of me wearing it. About a week later it came, it was a set of panties and a camisole, and I immediately obliged her request for pictures.

 

I'll probably post more tonight.

 

Drank last night, hung over today, concert tonight. No time for writing any of this until at least tomorrow night.

 

We'll get there.

 

So here I am, in the fall of 2006, falling in love with someone half a world away. Someone with whom for the first time I felt somewhat comfortable being honest with myself sexually. The only real problem, besides the distance, was that she was in a relationship with another woman. One day her girlfriend, who was also a member of the same Internet community where we met, found some pictures of me on her laptop. Things got really ugly, really fast. But in the end, they broke up and I maintained a long distance relationship with this girl. We were most definitely in love, and couldn't bring ourselves to face reality that this whole thing was doomed to fail.

In early spring of 2007 she flew half way across the planet to spend two weeks with me in a hotel room. Up until that point we had talked a lot about fantasies and kink, bringing them into the fray when having phone sex or skyping or whatever. But orgasm control wasn't really on the radar much. At the time, chastity and orgasm control was just another kink for me, and it hadn't yet occurred to me that it's actually the root policy of femdom (at least in my opinion). At this point, I wouldn't really feel like I was being dominated if I was free to jerk off when I got home at night and have an orgasm pretty much whenever I wanted. But we're not there yet.

Most of what we talked about was dominance in general terms, with her setting the tone, initiating things, me giving oral sex on command, blurring gender roles, etc. One that she brought to the table was anal play. She loved the idea of using a vibrator on me, and I must admit, I loved the idea too.

But when she got here, it became very vanilla. I lsot my virginity to her, and though she was a lot more sexually experienced than I, I don't think she was when it came to kink. So instead we did things that came more naturally, and despite putting fantasies on the back burner, those two weeks were some of the best times of my life. We were passionately in love, having sex at least three times a day, and having the time of our lives. It became clear to me that she wasn't 100% sexually dominant, which was fine really, and we had a lot of fun with me as the aggressor as well.

About halfway through her stay here we visited a sex shop and bought a few small vibrators to try on me. For the rest of her time here most of my blow jobs occurred with something buzzing in my ass. The power dynamic became very blurry, she was both accommodating and dominating when she did that. She never asked my permission, but was tender. I came every time. She suggested I wear her panties in bed too, which once again didn't really push the power dynamic too heavily towards her, but just left the roles very blurry, which in itself was something worth exploring. I learned a lot about myself, and a lot about her, and I wouldn't trade those two weeks for anything in the world.

After she went home was the first time orgasm control really came up in our relationship. I don't remember which of us suggested it, but it's something we started toying with in a VERY low key way while we maintained a long distance relationship over the next few months. I wasn't 100% forbidden from cumming without her say so, but I was strongly encouraged not to. It made the phone sex a lot better if I hadn't jerked off since the last time. But after a few months of that we kind of just stopped doing it. I don't think she was the biggest fan of it, and since it was done in such a low key way it wasn't the best for me either.

The final part of my relationship with this girl will come in the next installment.

I noticed this thread nnow has over 200 views. I'm not proofreading these posts, so if anything is unclear or whatever feel free to ask me to clarify.

 

Yes Mistress, I will resume posting here soon.