Sheila's Training Ch. 01

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I was shocked, suddenly, to realize my finger was going in all the way to the end. God, I'm really in deep! I told myself. I felt like I was running with the wolves now!

"Okay, that's good, you're doing real good," he said, very very quietly. "You can stop now, if you--" he paused, and it took me a second to realize that he was wondering if I was going to go on, like some automaton, fucking my asshole with my finger while he stood there and watched all afternoon. Damn, I was still fucking myself in the ass with my finger. Mmm, one more time. I let my finger slide out. It felt so wrong to stop.

Matthew turned on the hot and cold taps and reached for me. To my amazement, he clasped my dirty hand, the one that had been fingering my bottom, and walked me over with it to the sink. He used his other hand to squirt some soap and worked a lather over top of mine. Our hands separated and we washed up, me breaking the eye contact for a few moments as I got myself clean, all ladylike, as he rubbed his hands together, rinsing off after I did. As he moved past me to take my place at the sink, I thought I noticed a bulge in his pants. Well, public displays have a weird effect on all, I figure. It's meaningless, beyond our control.

I cleared my throat, which was getting kind of unworkable for the purposes of conversation, and fixed my panties and sat back down all demure-like while Matthew scrubbed up my new sex toys and poured them a bath. For a couple of minutes while he was intent at his task we neither spoke nor looked at each other. Eventually he was satisfied and, turning to me, said, "Just let 'em float around in the hot water for ten minutes or so and you can rinse them off. Then set them out in a row so you can contemplate your destiny!"

I nodded my head silently, trying to take everything in.

"Now remember, don't go transferring a finger that's been in your bottom to your-- into your snatch or anything. Wash it first."

"Oh, right--"

"Or just, you know, use a different finger." He was trying to be serious, but then a little irrepressible grin broke free. A shy grin, as he lowered his eyes until he could suppress it. Oh, sweet sweet boy.

But then: "What did we say about after dinner?"

"Oh, ahm, take a dump and put the small butt plug in for-- one hour."

"That's right. You can handle this, you know," he said, in a 'don't let the team down' kind of voice.

"Yes, I'm not afraid now that I've--"

"After it's been in for one hour, I think you should go ahead and masturbate with it in."

I blushed furiously at the mention of the word 'masturbate', hardly able to think rationally of the fact that what I had just been doing in front of him was my very first act of anal masturbation. "You're telling me to play with myself?" I asked, as though I should be shocked by the suggestion.

Matthew looked at me as though I were a genial lunatic. "Don't be coy Sheila. This is a training regimen after all, and I am the trainer. Don't fiddle with the plug itself. I just want you to leave it in after your hour is over and play with yourself with your fingers, think whatever kind of sexy thoughts turn you on, and make yourself come. Just plain, hands-on masturbation, but with the butt plug inside your ass. Just keep it simple, like that."

"Okay. Aye-aye, Ass Coach!"

"Later on, assignments will get more . . . complicated, naturally."

"Oh of course," I said, trying to sound nonchalant. Shit, what 'complicated'? But then I thought of my largest plug, and what that could be like inside my tight little hole. Damn, what have I gotten myself in for?

Matthew was looking at me as though, yet again, he could read my mind. "You're on your way to becoming a true Ass Slut, Sheila." He walked over to me, and, to my great surprise, bent himself to my head and planted a little kiss on my forehead. Still close, so that I could feel his breath on my face, he intoned the words again: "Ass slut."

He straightened himself, looking like the canary that ate the cat and, still watching me, let himself out.

I lay back, hiked up my skirt and palmed my hand over my crotch where my boy shorts were sticky with all my accumulated secretions. I rolled onto my side, worked my panties down, and reached with my finger back into the furrow between my buttocks, just letting it rub the outside of my little rosebud, shyly, tentatively, while in front I crooked two fingers inside my cunt and started rubbing them purposively against my sweet spot.

My thumb had just begun to pad the slick side of my very popped-out clitty when I came, hard, just thinking about the slim straight plug that was to be inside my ass this evening.

Minutes later I lay down again, looking out at the top of my dresser where the formidable row of black probes now rested.

Hope of a peaceful nap was dashed as the enormity of my day's proceedings began to crash away at my consciousness, like an ever-surging storm tide breaking against a cliff.

"Oh my god," I whispered to myself guiltily, with my stomach in a heave, "I'm an ass trainee . . . ."

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5 Comments
AnonymousAnonymousover 6 years ago
Hot start

What a hot start to a story. Nice characterization and grassy dialogue.

BluegrayBluegrayabout 12 years ago
Fun story

What an enjoyable read. You tell it well and make the characters feel very real.

Thanks

PacoFearPacoFearover 13 years ago
Double-thumbs up!

I picked you up when you earned your green 'E' for "Emily, Disaffected" (congrats on it!) then wandered here next. I'm really enjoying your clever, snarky, literate style. Your stuff reads both smart _and_ dirty, my absolute favorite. I'll be tacking you onto my favorites list in about ten seconds.

Cheers,

-PF

AnonymousAnonymousalmost 14 years ago
I hope you finish this one

It's a promising, rather erotic start..

AnonymousAnonymousalmost 14 years ago
Anal Sex is Tops, in our view!

A most thoughtful entrance into the dark world of Anal pleasure, taking her readers where the sun never shines, as a rule. Your fans look forward to further BDSM/Anal type adventures, as a trainee experiences masochistic pleasure beyond her expectations, leading to gay sex with queer boyfriends and 'vanilla' lovers alike?

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