My path to chastity

She just let me play, there were edges involved though. Kind of hard not to edge when you've been locked for 20 days!

 

Today was a big step for me. After previously having begun to experiment with anal play I decided it was time to get some toys which were designed for it, today they arrived. So what did I get? Well I found a bundle that was in a sale that included a small and a medium butt plug, a small dildo and what looks like a training set of vibrating beads. (Thank you @Charlotte Starbuck for pointing out a good starting place).

Now when they arrived my girlfriend and I took a look at these items and she in particular found it quite comical. The small dildo was a sort of jelly material and the girlfriend looked at it and said "It looks like it has a suction end!" to which I said it did and then stuck it to the wall, this set off her first giggle fit. The next one came when she read the box for the same item that said now jelly wasn't just for breakfast. Several minutes later after recovering from that giggle fit she set herself off again by becoming a unicorn and putting one of the plugs on her forehead. After she calmed down we looked at them seriously and agreed; the larger plug simply looked too big. The gf then left so I could experiment on my own.

Now I started playing around and once I'd tried the small plug I realised it was really only good for training to larger things so I took the plunge and tried the larger plug (that is termed a medium). I tried and got most of the way with it but it just seemed too big. I had just given up on it when I got messaged by @Rachel Cash to whom I mentioned my problem and after a bit of advice from her I tried again and succeeded. I am so glad I did try again; after a bit of moving around I found that even small movements were rather pleasant. At this point I got out my wand and placed it against the plug and just WOW! I could have just lay there all day it was that good! There was just one little problem; I'm still locked up and so I discovered new levels of frustration. After that I finally tried the small dildo and simulated fucking myself with it; again very fun.

Having done my experimenting I went and talked to the girlfriend; I was a horny frustrated mess who was still breathing heavily. She proceeded to tease me by playing any number of appropriate songs about sex and reminding me it could be worse; she could be getting off in front of me now. At least when I said I wanted to get her a strapon in the future she now seemed much more amenable to the idea than she has in the past. So I am now as horny as I have ever been and am completely torn between wanting to get out and orgasm and wanting to get taken however, that's not a choice I get to make.

A parting thought that I had on this; lots of guys say they want to try anal and I have once done the taking, that was a pleasant experience. However, if they only new the joys of anal play and got past societal hang ups they'd be begging their girlfriends to strapon and take them instead.

 

Very generous of you Lady Jezerae. My journey with anal is only just beginning but I feel that I too will come to love it perhaps a bit too much.

 

Well it's been a while since I updated this journal so here goes. Unfortunately I've not hand any interesting session or experiences to document as I've been too busy moving house. However, I believe that I have become increasingly comfortable and used to the cage.

I know find my mind wandering to what I. Should do when I get unlocked which most likely will happen in the next few days. Unfortunately I'm moving away from my girlfriend at least for a few months and so I won't be doing another session in the cage with her and her friend. However, I'm enjoying being locked up and thinking about doing it over the Summer only I wouldn't self lock, one because I wouldn't be strict at controlling my release and two because there would be no teasing and without that frankly I find chastity play boring. So my first option (and I know a few KHs and other here who'd want me to choose it) is to get locked up again and explore my submissive side further.

Now the alternative is that I let my dominant side out and stay unlocked for a while. After all I have neglected that side of me over the last month and I know a few people who could use a good teasing and denying. I would very much like to be the one to do that to them. So that is my second option.

I'll find my path when the moment comes to choose but for now I am happy to hear advice and suggestion as to which path I should choose. And thank you @Lady Jezerae for your input so far.

 

Just got word that I'll be unlocked later today. Decision time is drawing nearer.

 

Did you mean do Lisa? If you're asking what I decide to dom it could be you

 

We all know it was a Freudian slip

 

So this morning was my first orgasm in 29 days! I'll start by saying that one of the reasons my girlfriend likes chastity play is that when I'm let loose I can be very aggressive and sexually dominant and that's what she enjoys. I think perhaps this time I'd been in the cage a bit too long to be as aggressive as she'd like but there's time for that later.

So what happened? Well in order to try and build up some stamina I had her blow me to 3 edges. (I'm sure many of you know how quickly you can go off after a month in the cage.) After that it was time for me to have a little fun, I got her on all fours and started spanking her. I then informed her that seeing as I couldn't spank my KH she would just have to take a spanking for 2 that left her cheeks a very nice shade of pink. After that I began to take her from behind, this culminated in what I can only describe as the longest orgasm of my life, not necessarily the best but certainly the longest.

So,I am free now and am going to enjoy that for a few days and then decide whether I want dom or sub next. Before the orgasm I was leaning to sub now I am leaning towards dom.

Ps. Sorry if I'm a bit of an arse in the next few days as I readjust to being able to orgasm again.

 

Well I'm enjoying being free at the moment and the idea of being dom I rather appealing, unles any strong woman manages to convince me that what I really need to do is put the cage back on.

 

Having far too much fun teasing you to be caged now Lisa!

 

You think I'm too dangerous for you uncaged?

 

So I've noticed I have become rather cheeky since being unlocked. Maybe I should get locked for my own good.

 

Have I been free too long? Have I had too many orgasms lately? These are the questions I've been asking myself the last two days. I want to explore my submission more and have a new KH lined up but just don't seem to be able to take the leap

So what now?