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.

This entry was posted on Thursday, January 29th, 2009 at 10:44 am and is filed under Jill, Reality, smut. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.