Today

What have you done so far today Akalashi?

I woke up to a picture of my cock locked up in chastity once again. Due to arrangements made before I even met the boy, Devin had a couple of weeks where he was to play with another Domme who was going to be in town. Though I’m not positive his newly found predicament would have gone against their arrangements, I thought it would be nice to allow her the freedom to perform CBT on my  cock. If she desired. Because I’m a Sadist who enjoys pain being inflicted. Although if I’m performing CBT on my cock…I think that makes me a masochist. Food for thought. Regardless, this was a weekend where he wouldn’t be seeing her, so I swooped right in and locked him up again.

I had a boy scope the closest Victoria Secrets to my house, in hopes of allowing me to witness him shopping while cross dressed in a french maid’s uniform. This is one of the men that I found on CollarMe who, unfortunately, doesn’t match a whole lot of what I’m looking for in a relationship, but has plenty to offer in way of cross dressing for the masculine figured male and just general life stories. When I found out he went into public dressed like this, I hoped he would eventually make his way to my edge of town so I could witness him shopping. I would love to take a few pictures of him and even choose some new panties for him to buy and wear to work.

I received text after text from an eager pup discussing our plans for the evening. I put it nicely, but I can sum up an entire day’s worth of texts in three words: anal, do want.

I again reminded Devin that in signing over his cock to me, he gave up so much more than just his orgasms. Seeing his cock outside of plastic or steel was a given. Orgasms were a given. Ejaculating was a given. Sex? Absolutely, yes please! But all of those things were taken when he gave me his key. Now we’ve moved into the realm of milking. He had no idea that went with chastity. He had no idea that I could strip him of his semen without ever allowing him an orgasm. Just more to add to the list of things he unknowingly handed over to me that I am not about to hand back. There are a few more that he hasn’t quite thought of, but I figure I’ll let these sink in before acknowledging them with him.

I fit a strap-on harness to wear over my jeans, like a bad comic book hero…or villain. In a recent conversation with Joey, I admitted that part of the reason why I didn’t like to do strap-on play was because I hated being naked while I was in a scene. So, being astute, he said ‘Don’t be naked’. Simple as that. In those three words my biggest complaints about the play, about the gender confusion, about hating that my female body doesn’t match the act I so longingly wish to make come true without the use of plastic and silicone were eradicated. He didn’t think I’d look stupid if I wanted to fuck with my pants on. So I’ve taken to making that happen.

I found a way to fuck with my pants on. No really, I think this is pretty amazing, especially given my stance on sex.

I’ve had my stance on sex questioned so many times I’m beginning to wonder if I really hate sex at all. Not that I’m weak-minded, or have no idea what I want, but the more I talk about why I hate it, the more I realize that maybe the reasons weren’t why I hated it as much as I didn’t have the right partners to try things with. I’m not saying I like sex, I’m just saying that I might want it. A lot. More often than I let on.

I encouraged my bottom to pay tribute for his future ass pounding. And by tribute, I really mean he ought to donate a pack of beer to my fridge to help me cope with the long weekend ahead of him not being here to beat and fuck. I hate people messing up my schedules. Family? Who needs family when there are floggers and strap-ons to be had?!

I worked out a few ideas in my head for a future journal post. But if I write it here, no one will come read it later, so that’s all you get.

This has been my Friday in a nutshell.

 

Fluid

One of the requirements that I had on my profile when I was listed with CollarMe.com was that anyone that wanted to be mine would have to be fluid, they’d have to be able to move between pet and boy, submissive and servant, friend and slave. They’d have to know when to slip into each of these roles and be comfortable with having so many roles and I acknowledged that it could be difficult to do, but it was necessary.

My family (for the most part) knows about me. They know about my relationships. My friends of the family do not. To them, j is a friend that comes to have dinner with us once a week. They’re all very nice to him and I’m sure to keep my physical affection for him very low when we’re in that particular place, simply because everyone there knows my family. When the three of us are going out together somewhere new though, I can hold hands with either of them, walk alongside either of them, put j behind us or in front of us, and receive kisses from either of them. It might seem weird to anyone else, but to us, we know what’s going on and that’s just how this relationship works for us.

Last night, the three of us went to dinner together usually reserved for couples. Having an odd number of people probably stuck quite a few people as strange, but it was very natural for us. After that, j drove us to our house and he asked if he could stay for just a bit. I took him into the bedroom and curled up around him, snugging him as has become some kind of ritual before he leaves for the evening. My husband came in and joined us, putting me in the middle. Towards the end of that, he put his arm over me and over j as well, and j turned into the cute little wigglebum that I know him to be, where if he had a tail, he’d surely be wagging it.

I didn’t want to end the weekend there though. My boy has reached some new heights emotionally, finally being able to cry in front of me, which seems to have brought us closer together. He’s been very close to me, physically and emotionally, and just absolutely gushy since we first got together Thursday night. Since I still have two days of vacation, I figured I might as well spend them with him, and so decided to go back home with him last night.

Already exhausted from a three hour dinner with my favorite people in the whole wide world and a very cozy hour of snuggling at home, I wasn’t expecting for much to happen when we got to his place. I just wanted to curl up in bed, curl up around him, and doze off.

Except. Except that for some reason I couldn’t keep my hands off him. He needed to make the bed so I could get in it and just about every time he rounded the corner, I was either touching him or pushing him over the foot of the bed, mimicking the very pose I use when I want to fuck him in the ass. It went so far as to push him onto the bed, climb on top of him, and kiss down his neck, knowing it would melt him.

Once in bed, I was far too tired for sex. I was probably too tired for orgasm, or so I thought. I wasn’t too tired to watch him entertain himself though. I had him strip down to his tight orange panties and rainbow socks and then had him climb in next to me and masturbate. Just a few moments later, I invited him to sit up on my lap so I had a better view of his cock, the way he was teasing himself.

For the most part, I was good. I didn’t touch, which allowed him to masturbate for longer. I didn’t talk either, because I know the things I say arouse him. I did let the word ‘slut’ slip and I was afraid he might orgasm so I decided to remain quiet. The only thing I couldn’t stop myself from doing was pushing up against his ass. I could rub my clit against him and I didn’t want to give up the meager stimulation I was getting. I wished I’d put something on before we started playing because he was so dangerously close to orgasm that I couldn’t hardly even touch his cock.

I asked him what kept pushing him so close to the edge when he wasn’t even stroking and he admitted it was the feel of me pushing up against his ass, and he said how badly he wanted to feel my cock inside of him. I told him that probably wouldn’t happen tonight, but he could go fetch my cock for me anyhow.

The Feel-Doe is really not a bad toy at all. I really cannot stand penetration of any kind (because I find it painful) and so it doesn’t get used very often. When I do use it though, I love it. I love the weight of the thick cock resting against my clit when I’m on my back, which is the position I’m most often in when I’m wearing it. If I’m really, really aroused I don’t have any trouble sliding it in and holding it there, but I hadn’t reached that point of arousal physically. I had him wait with his nose against the wall and his wrists crossed at the small of his back as I situated myself, and then I had him climb on top of me again.

He was already so aroused that he didn’t even need to stroke. Instead, he just rubbed his ass against the bulge I’d created in my pants and the lust in his eyes was evident. I was thoroughly enjoying myself as well. Tonight, learning from past mistakes, I told him to put on a condom. About fifteen seconds later, with my permission of course, the two of us were enjoying some fantastic orgasm, his second for the weekend and my fourth for the day.

While it didn’t go as flawlessly as I would have hoped, it went well enough. I need to figure out how to slip that sucker into me without needing five minutes to adjust. I could have used the harness to ensure it didn’t slip out, but it feels so unnatural to me that I didn’t want to bother. As a result, when he first sat on me, he pushed it out a bit because he immediately pushed back against it. Closing my legs tight and having him sit further down on the shaft made that much easier to handle. The best part was that when I was finished, I could just pop the sticky part into his mouth for clean up and roll over for sleep.

Eventually I’m hoping to get to a point where I can just slide my cock into place and engage in anal play the way I want to. Right now, I don’t think he can handle the sheer girth of my cock, but it won’t be much longer before he can. I want to see if I can ever use it without the harness in the way that I want to. I like the idea of me being on top, fucking him like my pretty little girl, my little princess. That’s what I fantasize about. When I fantasize about just fucking his ass as hard as I can, I can use the harness. It works in that fantasy. Right now though, it would seem I’m trying to fulfill some of the gender confusion that we both suffer from, that we suffer from happily. I’m sure this will have a great ending. It’s all about the journey anyhow.

Gender Fuckery

This is actually one of my favorite topics. I’ve been dealing with gender issues for as long as I can remember. It started innocently enough, making a male character in a game instead of a female. Often times, my personality seems to fit the stereotypical male more than the stereotypical female so I figured I could pull it off convincingly enough. I found when doing this that a lot of what I said, or how I thought, or the way that I did things went over so much better when people thought I was a man than when I was a woman that I never went back. Not until about two years ago when I got introduced to Second Life. I wanted to stop roleplaying for a while and just be me, and in order to do that, I’d have to make a female avatar and be myself. A scary concept after existing online only as fictional characters.

After that huge step foward, I came to realize that I like a lot of what I do from the male perspective better than the female. A lot of this is just the things I’d been taught or what I’d witnessed along the way and most of it isn’t factual. For instance, I was convinced for many years that women certainly couldn’t be in control. Their emotions would get in the way every single time. To some degree I still believe that, but I don’t think it’s such a terrible-bad thing anymore. So what. We’re emotional. Sometimes we’re more compassionate, or could be, anyhow. Our genders don’t really determine a whole lot socially. This was a conversation that j and I got into when we decided to go have breakfast at half past midnight in a cute little diner.

When I step back and look at it, I know it has nothing to do with gender. A lot of everything has to do with how we were raised, the values instilled within us when we were young. Even now I can look back and see the negative reactions from family members and friends alike when they realized that I was the one in charge of my relationships. I’m sure that’s where a lot of it stems from. Another factor is just hanging around the wrong people or gleening the wrong information from people. I wasn’t looking at the big picture.

What brought all of this to mind though was one really hot comment that came from j when I had him pinned face-down on the bed the following morning, after our gender talk in the diner full of crazies. It was a really hot comment to me now, but when it was said, it brought a whole lot of thoughts that I’d had over the past couple of years right to the surface of my brain and I almost, almost, couldn’t move past it to keep enjoying myself. But I did. Which, to me, shows growth in that area. So huzzah for me!

I came back from the bathroom and crawled over him, as I usually do. He sleeps nearer to the bathroom and I don’t want to walk around the bed. I usually get right up on him and start biting, because that’s what I like to do. Then I’ll rub myself against him and typically he’ll just turn himself right over, happy to offer his ass to me. I can have an entire orgasm from this, actually, and most often do. This time he actually spoke. He told me that he wanted to feel me inside of him. As I type it now, even, it’s hot to me. At the precise moment that he said it, I had to turn it over in my head. I had to make sure he’d said what he said. For a split second, I thought he was confused. Then I realized what he was wanting. I might have even put forth the extra effort to do just that, except the little voice in my head prevented me from doing it.

What very nearly came out of my mouth was that he’d never actually feel me inside of him. He’d only feel some silicone toy inside of him. He’d only feel the false representation of what he really wanted to feel inside of him. My boy’s a smart creature though and he surely would have retorted that it absolutely is me because we say it’s me, because we say it’s an extention of me, and that’s what he wants. He didn’t have to though because my good sense kicked in! (For once.) I kept my mouth shut, but I kept those words at the forefront of my mind.

What really got me about it was the fact that I’ve been struggling with the issue myself. In my fantasies I can always push him up against  a wall and take him. Bend him over the couch and take him. Smack him around and then penetrate him. Penetration is a huge part of what I fantasize about. In my fantasies, it happens just like that though. There’s no ‘Oh, hold on one second while I pull out this harness and finaggle a fake cock into it and then line it up just right so that maybe I’ll get some stimulation from it as well and then we’ll get to slowly warming you up so that it’s enjoyable for you and so we don’t have health issues later on down the road. I’ll be right back. Don’t lose that arousal.’ None of that. It’s just bam, bam, done. That’s hot. What I really have to go through to get it? Not so much.

So I took this super intimate problem to the only person that I’d trust with such a super intimate problem and we discussed ways to make it a little better. Maybe start play with it already under my clothes. Like, are you happy to see me or is that a fake dong in your jeans, eh? Right. But it’s plausible. I mean, it sure could happen. Maybe try incorporating it into some of our gender play. Those times when j’s crawling around in just panties and painted toenails and the such. Eventually something will click and it won’t seem so…fake to me, or so I like to think.

Fast foward two days to when we have a date (yes, yes, a for reals kind of date because over the weekend he was all kinds of cute and asked me if I’d go to the movies with him and I said yes, constituting a date) and he says something else that’s all different kinds of hot to me. As I’ve got my arm around his shoulders and we’re waiting for the theater to be cleaned he whispers to me how he likes that he always feels like the girl when we’re out. Zing! I love that. I love that because that’s the feeling I like to create. Because I like to take on the traditionally masculine role, except somehow I don’t ever get to pay, which is not traditional, but I don’t think I’m going to argue it either. When I plan the dates, I get to pay, so it’s all good.

So emotionally, I’m totally the guy. If only I could pull it all together so it could be done sexually as well, because I get this feeling that we both totally want it. Really bad. Me more than him probably, which is why it’s so frustrating for me. I’m sure I’ll get there.