Jilling Off

I once had a friend who did sex work who always told me that I would make a fantastic dominatrix. The idea intrigued me, and I had some extra time over Auckland Anniversary Weekend, so I decided to plan out a treat for a gentleman caller.

Half the fun for me (well, maybe a 20th of it at least) was in the preparation. Knowing that he’d mentioned having his cock tied up, I discovered that CBT is not just Computer-Based Training, or indeed Cognitive Behaviour Therapy – it can all be Cock & Ball Torture. You learn something new every day! I managed to find this extremely NSFW step-by-step pictorial guide though, which came in handy (almost literally) before I had a chance to do the full routine on an earlier occasion when I was squeezing someone’s balls and was a little alarmed about how separate and jumpy-aparty each ball in its sack is. And the ballholder didn’t seem to have any problems with it either. Anatomy is strange.

Another area that I had to prepare myself in was my outfit. Obviously a corset, a riding crop and ridiculous platform heels would all be in order, but because I felt like I was playing a role, I added in a wig and a mask.

I laid out all the tools that I would be working with – scarves around the bed posts, a coil of cord for the CBT (and a pair of nail scissors in case it all went horribly wrong and needed to be cut off in a hurry), a blindfold, feathers, an ice bucket, a pot of hot tea, some feathers, my vibrator, some lube and there would have been a box of latex gloves if I hadn’t decided that that would just be creepy.

Then I put on my serious face, and set up a playlist to reflect my sternness. The gentleman caller arrived late, in need of punishment already, obviously, to find me angrily thwacking my riding crop across my gloved palms. He said “I’m going to like this” and I told him to shut his fucking mouth, stepped away from his kiss and ordered him to take off his clothes.

As soon as he was naked, already half hard, with me loving that I was still fully if somewhat ridiculously dressed, reinforcing my power, I smacked him really lightly on the ass, sat down on my bed, spread my legs and told him to eat my fucking pussy. He dived right in gleefully, and as I was pushed back on the bed, I realised the problem with the wig and the mask, because I constantly had to readjust them. Meanwhile his tongue curling around my clit, slipping around my cunt was starting to make me feel like I was losing control of the situation, even though I was holding his head fast in place, so I declared that he was enjoying it too much, and pulled him to his feet, then pushed him onto the bed.

He didn’t even pretend to struggle as I spread his arms to tie them apart, but he was intrigued when I looped the cord around his cock and balls, doubled it back around the ball base and then separated the two out. I licked his balls lightly in lieu of tying proper knots, and then decided that he was enjoying the sight of me working on his cock a little bit too much so it was on with the blindfold.

By this stage since he couldn’t see anymore, I figured it’d be more comfortable (and no doubt a fuck of a lot more safe) if I took off my shoes, so he got to hear the traumatic thuds of the platforms hitting the carpet below the bed. I was absolutely loving having him under my control. A couple of quick flicks of the crop – first to my own hand to get the good cracking sound, and then the lightest whisper of it across his legs had him tremble a little bit, so I upped the game.

I had never realised that an ice cube could be so entertaining, but as I dragged it up and down his legs and across his chest, he twitched and twitched, almost squealing. It was fantastic and I couldn’t help but start to giggle. To make it up to him a little bit, I took the ice cub in my mouth to cool it down, and then wrapped my lips around his shaft, giving his whole cock a quick suck, before I took a mouthful of warm tea and repeated the exercise.

I did a couple more passes around his body, alternating hands with lube on his cock, feathers and ice across his skin, before I knelt over him and allowed him to take my nipple in his mouth. He sucked as if his life depended on it, so I took my breast away, and turned my vibrator on, holding it to his balls, moving it along his cock and down t press on the perineum. By that stage, his blindfold was coming off, so when I declared that I may as well just use the vibe on myself instead of him, he could pin open my legs so he could watch everything I did to make myself come. In fact I came twice, loving that he was loving the show but was frustrated in his lack of ability to take part in it.

After I got my breath back, I noticed that his hand up against the headboard was turning purple. Oh fuck! I scrambled to untie it, and figured I might as well untie the other hand as well. I was having a hell of a time maintaining Fierce Face anyway, because really, I just wanted to be kissing him and having him finger-fuck me and eat me out half a dozen times.

Naturally, it turns out that he didn’t even see the wig which I abandoned halfway through the session. To quote “when I came in the door, I saw breasts, the mask and the riding crop and that’s all, I was so excited”. He didn’t notice the playlist either until we were cuddling and ‘Closer’ by NIN came up. Mogwai was my more subtle way of setting a scary mood.

I had fun trying out being a Dominatrix-Lite, and he had fun, so now I’m wondering when it’s going to be my time to receive someone else’s roleplay.

• Me as a hardcore sub
• Photographs or records other than hurried pxts from the bathrooms of our work
• The toilets in a bar
• Bringing in an anonymous third party
• Spankings delivered sharply to me
• Anal play
• Waking up with you

I know this is by no means a exhaustive list. And I know I’ll have to complete it with someone who isn’t you. Sigh.

I’ve started blogging for The Aucklandista! It’s tremendously exciting, as this means that I’m practically in the Wellingtonista, except that they make me do stories on Dogging.

Recently, Giant wrote that he was surprised that I have tendencies towards being dominated. I can get where he’s coming from – outwardly I’m a bossy, in control woman (I do PR for a living) but seriously, if you’re ordering minions, printers, caterers and stupid clients around all day, don’t you think that you’d want to come home and be able to switch off totally too?

That is of course the superficial level of domination/sublimation, but unfortunately anything to do with sex has to go deeper. I like to think that I am amongst strong feminist women, so the idea that I want to be dominated and degraded does really not sit well with me as a feminist. I know there’s a difference between fantasy and reality though, and this is where I’m especially grateful to Dan Savage for explaining it so clearly:

Like many fetishes, his cuckold thing is most likely a subconscious erotic response to a sexually charged fear. While most of us learn to live with and occasionally conquer our fears without eroticizing them, a number of us respond to sexual fears or traumas by incorporating them into our erotic imaginations. Think of women—hip, together, progressive, feminist women—who act out rape fantasies; think of the homos—hip, together, out homos—who dress up like soldiers, cops, firemen and other stereotypically violent homophobic types.

So women fear rape, yet some develop a fetish for it. Gay men fear violent homophobes, yet some dress up like violent homophobes. And what do many straight men fear? Being cheated on, of course, and dealing with that particular brand of sexual humiliation.

So yeah, I think if I was imagining people grabbing me the way they did when I was 12, if I was fantasizing about leather jerkins and tattoos on bare chests,then that would be really troublesome. If I want someone to pull my hair, call me a dirty slut and maybe spank me a little, I’m okay with that.

When he asks me lights on or lights off, I don’t get it at first, and then I realise my mistake as the fluorescent lights flood the room with their harsh reality. But yet – this isn’t reality. How could this be real? I’m 19 stories up in an empty office building with him. I would like to be looking out the window at the Auckland by night, but it appears he has other ideas, as he comes up behind me, grabbing my ass, and kissing my neck. He guides me over to where his workspace is, and I know exactly what he’s after right here. I’ve sent him enough text messages about it, after all, and received enough to know how hard I make him when he’s sitting at his desk, trying to work, so this is my time to make up for all that.

I sink to my knees on the rough commercial carpet, and pull him closer. I struggle with his belt buckle, so he laughs at me, but just enough so that our eyes meet. He likes the show, so I take my time unbuttoning his fly, coy face on. He is hard already, a product of waiting for me outside the building, I’m sure, waiting for me to wrap my lips around his cock, but I don’t want to make it quite that easy for him. I pull his cock out of his underwear and put my mouth up to it, but I pause before licking around the tip, smiling as his eyes roll back in pleasure. Now I have a taste for his precum though, so I open my mouth wider, and try to take the whole shaft in at once, holding the base so I can retain control and not push beyond my gag reflex. I can tell he likes this a lot, although he is almost silent, because of the way his hand grabbing my head and the other reaching down to my breast.

“You saw the security card parked outside, right?” he laughs, as I reach further into his jeans to squeeze his balls.
“Do you think they’re watching us, right now?” I slide back from his cock, but take the time to bathe it, lapping my tongue all over every inch.
“Oh, no doubt,” he says, laughing. “Cameras everywhere”.
“I might as well give them a real show then,” I say, and pull off my tshirt. He takes the initiative, pulling down the cups of my bra to take a nipple into his mouth. His right hand travels up my thigh under my skirt.
“I’m surprised you’re wearing these” he says, running a finger along the crotch of my panties. I am set to protest my ignorance about this night’s expedition, but find myself merely gasping instead, as he starts to kiss my neck and my ear, as he slides his hand into my panties.

I’m still kneeling, and my jandals are scrabbling to hold my position on the course carpet as I spread my legs further to accommodate his fingers. He slides one finger up and down my labia, which I imagine are parting like the red sea to his Moses, but I stifle that image as he kisses me ferociously, pinning my mouth in place, as his finger trails up my wet opening to my clitoris. He’s the one laughing now as he circles it, and I gasp and lean forward onto his hands, I start to imagine how we would appear on security monitors, and think about how much trouble we could be in. That combines with the ache in my knee to want this to be over quickly, so I lean in more, and rub myself back and forth on his hand, clutching his shoulder for support. We kiss, and he sucks on my nipple and I feel all the sensations all over me – the cool-air awareness of all that bare skin in the office, the subservient position that I am, his mouth on mine and the piano chords his finger are dishing out across my pussy combine, and I am about to explode.

From the way I grab at him harder, and that my breath is coming in gasps, he knows that I am about to come, so he pulls me in tighter, and buries my face into his neck, so that when I cry out in orgasm I am not too loud. We grin at each other for a second, and kiss again as he tucks his cock back inside his jeans to be finished later. The security car is still parked outside when we exit the building, so I walk out all nonchalant, as if nothing happened, but the dampness of my panties would tell a whole different story.