“Women’s Prison II: Night of the Warden”: a searing indictment of today’s prison conditions and recidivism rates.

That became our new life. On some weekends we played Naughty schoolgirl and strict teacher. There were other games, of which Women’s Prison II: Night of the Warden was best. (There was no Women’s Prison I.) 

The thing with role-playing was to keep the format stupid, so there could be nothing of interest in the game itself. We didn’t want to develop a storyline or care about characters. The games freed us to explore darker bdsm territory while maintaining normal life the rest of the time.

Serious play was for the weekends. On weeknights Chloe got spanked or I’d take my belt to her as  for the sensuality of it, before and during sex.

Chloe encouraged me to experiment. I became better at keeping our sexual plays moving, and at seeming to control what happened while making sure that Chloe’s pleasures and preferences were well indulged.

I learned to give commands with apparent conviction, and – within these games – without embarrassment or political guilt. I learned to pause impressively, rather than dithering, when I couldn’t think of what to say or do next. It was acting from the William Shatner school but – like Shatner’s acting – it worked well enough.

Libertines at the altar. (Illustration from “Therese Philosophe”, 1748.)

I sometimes tried earnest conversation with Chloe about how our play could be defended politically, but she thought that my worries about it were my problem. She was merciless when she encountered sexist men, but she had no interest in ideology or activism. Chloe loathed authoritarianism, irrationalism, hypocrisy, stupidity and wilful ignorance, which meant she was not ideally placed to take much interest in political campaigns, except where they touched on science and got in its way.

I suspect that she mildly enjoyed the idea that her choice of pleasure might annoy the more puritanical kind of feminist, in something of the spirit in which eighteenth century libertines might sneak into a local church and have sex on the altar. In any case she played and helped plan our games with the kind of glee that suggested she was subverting something.

It’s not a game I’ve played for years. I don’t do any role playing any more. But it was worth doing at the time. There’s a hell of lot to be learned from it. 

Naughty schoolgirl and strict teacher is one of the tackiest scenarios in all pornography. It’s silly, clichéd, and politically suspect. But it had just introduced me to pleasures that I intended to explore and repeat.

I’d liked Chloe’s obedience, playful though it had been. I’d liked giving orders. Chloe’s show of respectful surrender, sir, and the way I’d asserted myself in response: that was exciting.

I hadn’t used a real instrument before. I hadn’t made a woman raise her voice in pain before. Both had overjoyed me. I wasn’t quite comfortable with the fact that Chloe’s cries of pain had turned me on, but I couldn’t deny it.

There was a hairbrush and a ruler in that drawer, and I knew that I’d use both on Chloe, hard, before this weekend was over. I wanted to hear her song of pain again and again, and to hurt and fuck and comfort the girl who sang it.

The game might be silly, but it took me to darker and more truthful places than I’d ever been before.

Till then I’d always tried to maintain and emphasise equality between my partners and me, even during bdsm sex. I’d get permission before I hurt her or tied her, not only before any session, but before proceeding with any action during a session. Consent had to be continuously asserted.

But Chloe had simply given me her submission and put me in control. Submission turned out to be more exciting than permission.

I wanted more of it. Within that game I could have it, and Chloe could have her pleasures, while – outside the game – we maintained the equality that we both believed in.

At a signal from Chloe – she said, “Are you going to fuck me”, with slight impatience, rather than, “Please fuck me, sir”, which told me that the game was over and we were back in propriae personae – I helped her up, embraced and praised her, and helped get that uniform off, undoing buttons and tugging with clumsy impatience, then shed my own clothes and pulled her to bed.

Chloe wouldn’t let her strapped skin touch the sheet, let alone lie on her back. I wanted to fuck her from behind, sinking my cock between her glowing buttocks, but she ruled that out too. She wanted nothing harder than air to touch her bottom. So I lay on my back and let her straddle me.

She leaned down to kiss me and didn’t break the kiss while she lowered herself onto my cock, filling herself.

Then she sat up to ride, her nipples drawing pink spirals in the air as she bounced above me.

One last surge of cruelty took me as she was close to coming, and I reached back and smacked her burning skin while she grunted and galloped; and for the first time in months she made her crying and hiccoughing noise, as she came and fell forward onto me.

But this time there was laughter in the mix.

Chloe rested on me and I held her until she snored gently, her nose healthily cold against my neck. I lay awake and considered my new experiences. 

Chloe turned her head away when my arm moved, fixing her gaze on the chair seat. The strap landed with an astonishingly loud crack, wrapping itself round the lower slopes of Chloe’s buttocks.

The effect was dramatic. Chloe’s head shot up, and she sang out “heee-uuu”. On one hearing, that soprano cry became one of my sexual tastes. I wanted to hear it again.

I also liked the shockwave in Chloe’s flesh, as the heavy strap impacted, though because she was fit it lasted only a second. I watched the miracle of her skin changing colour, a brilliant pink stripe emerging, blooming like a stop-motion flower, about three inches across, with sharply defined edges.

It bobbed and weaved, that stripe, as Chloe’s hips bucked in the seconds after that impact, throwing off the pain like a horse trying to throw a rider.

I waited until she’d settled and arched her bottom up again. I aimed to leave the next stripe just above the first, neither overlapping nor leaving a gap. That was misplaced confidence; no-one should expect to land a strap accurately without practice. The strap landed high, leaving a sloping welt across the top of Chloe’s left buttock and wrapping painfully high across her right hip. Chloe’s cry was higher in pitch and volume. It was the wrong sort of pain.

But I swallowed the apology I wanted to speak, because it would break the mood and make things worse. I said, in the harshest, angriest voice I could manage, “Get that bottom up, girl. You’re getting strapped. And keep still!”

That was kinder.

For the third stroke, and all those subsequent, I aimed for the fleshiest part of her buttocks, reasoning that since my aim was lousy I’d achieve a reasonable spread of strokes just by accident, and that at least the strokes would land somewhere well padded.

“Lift up your skirt, Chloe, right up above your waist. Good girl. That’s a very pretty cunt, isn’t it?” I placed my palm against her, fingertips just inside, and stroked wetly. I held her to me with my other arm. We were almost ourselves.

Chloe said, eventually, “I don’t know, sir.”

I squeezed her lips, enough to hurt. “Isn’t it?”

“Uhh. Yes, my cunt is very pretty, sir. Would you like to fuck me, sir?”

“Chloe, I want you more than anything in the world. Or the world.” I said that. Mr Mortimer said, “But you’ve still been a naughty girl. You’ve got a pretty little bottom, too, haven’t you?”

Chloe had to think about that. Eventually she said, “Um. You might be nice enough to think so, sir.”