THE NOVICE – mistress in training

It’s an old fantasy. I tweeted about it.

A beautiful, experienced Mistress. A pretty, young novice, eager to learn. A male sub, there for demonstration & practice. That would be hot, right?

I’ve no idea what’s behind it; a submissive’s fantasy of being used, perhaps, handing over my agency to two strong women. When Elita tweeted an introduction to Lilly, a beautiful friend wanting to learn about being a dominatrix, it was this old “Mistress In Training” fantasy that jumped into my mind.

And if this wasn’t a role play; if she really was learning how to ply the sub with pain & pleasure, fear & desire might that be even hotter?

I booked the session and, in a fetid corner of my imagination, allowed the fantasy to develop, tweeting each new evolution as it occurred to me. However, waiting at the pub near to Elita’s beautiful mews house I was nervous: nervous of Elita’s cane but also nervous about meeting someone young and pretty who might not be comfortable playing with a garrulous old bastard like me.

I guess we could safely say of the sub in that scene “this is a lucky sub” could we not?

Oh, My Goodness. She was beautiful; sitting in a robe in a corner of the room, looking a little nervous. Hers was a demure beauty, exuding an irresistible combination of sexiness and innocence. In terms of the classic ‘stock’ characters of literature and film hers was the look of the ingénue. (No student of these things, I looked the word up: “The ingénue stereotypically has a fawn-eyed innocence, but subtle sexual appeal as well”. I SO had the right word)

And, of course, if the novice had to experience each part of the lesson herself before trying it on the submissive… even hotter, right?

After more than a year of sessions I can tell when Elita is enjoying herself and she was definitely enjoying this. She had me kneel on the floor, my back to Lilly who immobilized my arms while Elita slapped my face. She taught Lilly how to tie rope tight round my balls, causing just the right amount of sensation and making my cock bulge. My nipples were squeezed, twisted and bitten, first by Elita then Lilly (who has a natural talent for this) until I was fighting hard to control my reactions. It was a perfect, exquisite torment.

Nipples, slapping, CBT, flogging, caning. The Mistress would demonstrate, then the novice would practice each on the poor helpless submissive.

We moved to the bedroom. They both wielded floggers, one from each side, Elita’s heavy and thuddy, Lilly’s lighter but with more bite. Elita swung with vicious intent, slamming the heavy flogger into my backside, as if to make up for Lilly’s softer, more tentative blows. I was starting to feel floaty as the sensations built.

A new challenge: Elita’s Victor Tella hand-made whip is a beautiful but serious implement, the very thought of which sends my pulse racing even now, when I’m safely 100 miles away. She hit me harder and harder with it, the whip biting into my backside as I fought to hold still. Lilly tried it, but she couldn’t control the nine waxed cord tails and hit me high, hit me low and missed altogether.

If she got it wrong, she’d have to be punished by the Mistress, spanked perhaps. By the sub also. Poor novice, so much to remember.

The bed; Lilly over Elita’s knee being spanked. The picture tells the story. It’s classic male porn fantasy fare, but I’m not above this at all. Such a beautiful scene. Elita let me spank Lilly also; my hand landing on each cheek in turn, her silk panties offering no protection, causing little yelps as each blow landed.

and if, after the punishment, the Mistress left them alone, the novice would take it out on him, lashing out inexpertly, wanting to hurt him

Told she could offer me pain or pleasure while Elita was out of the room, Lilly chose pain, practicing her swing. She started tentatively, again struggling to control the long whip. But after a while I sensed a transformation; Lilly’s focus narrowed, she adjusted her timing and was rewarded by my sharp intake of breath as the whip landed fast and true across my backside. Again, on the same spot. And again, but harder. It hurt, but I loved that I was witnessing her transformation from the wide eyed young woman who had just been spanked into a Dominatrix. I could tell she was relishing her control over the whip, relishing the intensely physical interaction, relishing the distress she was causing me. To look round and see this disturbingly beautiful woman bring the whip back, focus her attention on a particular spot and then swing it with such conviction was, for a sensual masochist, about the hottest thing imaginable.

Perhaps, if he’d been a good sub, he’d be allowed to play with the novice on the bed, the Mistress joining in. That would be hot…

Lilly slipped her panties off and lay back on the bed, letting me move over her. My kiss was returned with passion so, gaining confidence, I kissed her face, her lips, her beautiful neck. Elita hit me with a cane, forcing me to fight off the sharp sensations to focus my attention on the captivating creature beneath me. Pain. Pleasure. Pain. Pleasure. Pain. Pleasure. It was erotic, emotional, beautiful. She took my cock in her mouth, sucking and teasing while I slipped my fingers into her wetness, further heightening my arousal.

We changed position. I could not have been harder, balls still tied, my cock engorged. I was ready. And then Lilly did the most amazing, sexiest, hottest thing; something that no sex worker has ever done with me before. Not even once. Ever.

Some outrageously hot, filthy, sex act?

No

She fumbled with the condom. Failed to get it on.

I’m still quite emotional about this. This pretty, lovely, enchanting young woman was new to this and had just shown me how new. I haven’t often had sex with escorts but there is a special trick they must learn at escort school that has the condom perfectly in place before you realise it’s out of the packet.

Lilly had fumbled with the condom.

For me, this act and the knowledge it gave me, somehow made our sex more than just a brief coupling at the end of a corporal punishment session. I desperately wanted her to enjoy it, to be OK with having sex with this much older man who had paid to use her body in this way. It became vitally important to me that this experience be as good as possible for her. I turned her over and took her from behind, not so much because I find this hot (though I do) but because she wouldn’t have to look at me; could imagine some hot young stud instead. My absolute focus on Lilly and her responses, as I pushed deeper while stroking her back, her thighs, her bottom, wanting it to be good for her, created a tipping point, releasing old, ingrained inhibitions. I came inside her, while wearing a condom, something I haven’t achieved for years. It was wonderful. Truly wonderful. We drank champagne and relaxed, as I reveled in what had just happened.

If, as the sub relaxed, the Mistress said: “The Novice will now take her CP exam, giving a judicial caning of 24 strokes.” Hot or not?

Well, hot, obviously as I wouldn’t have asked for it otherwise, though the sudden change of pace was shocking! They alternated six strokes each, with me tied to the bed, though Lilly’s first strokes were more practice than punishment. Elita hit me hard; really, properly hard, the cane making a meaty thwack as it bit into my backside. This post orgasm caning wouldn’t work for most, but for me it brings a wonderful clarity; pain as an experience in itself rather than pain as foreplay. She stopped after 24, though I think both of us wanted more.

In twenty years of seeing escorts, submissives and dommes, I don’t think I have ever had a more beautifully erotic or emotionally affecting experience.

And Lilly? Well, apparently, she loved it. And I want to take that fact and wrap myself up in it like a rug for…ooh… maybe a month or two.

There’s another super hot image form the scene on my Sinful Sunday post.

having labelled Lilly the Ingénue in the scene I got to thinking what parts Elita and I might have been playing.  

This is not an escort review site and never will be. However Lilly was absolutely wonderful and will, I am sure do very well in this new career. I was so lucky to see her at the start of the long weekend she spent with Elita, learning about escorting and how to handle different clients and sessions. I hear she was super confident by the end of the weekend!