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Sheila’s Training Ch. 01

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Big Tits

Not for nothing are “Ghost World” and “The Doom Generation” my favorite films. I was made for a stark black bob long before I ever got one, before I saw those movies and even before I discovered black hair dye. Without it I might have ended up looking something like Lotte Lenya in “From Russia With Love.” Goddess bless Manic Panic!!

It’s more than the hair, it’s the attitude. “Girl, you are the snarkiest bitch I know,” said my Best Fag Forever Matthew to me only the other week.

“I won’t be referred to as ‘girl’, not by a twee little sissy like you,” I replied campily. “I have enough with bourgeois clichés to deal with, I don’t need those of Queendom too.”

I was hip to the bourgeoisie thanks to my erstwhile boyfriend Ted, the philosophy major. ‘Philosopher,’ he would have it. That’s a crock. Not that I mind his warmed-over Hegelianism. He’s cute, Ted is. Actually smart too. Fuck, I’m such a softie. Why must I fall so easily?

Matthew is part of my ongoing therapy for the dark heart of sentimentality that lurks within. I wanted to cultivate fierceness. Be more Enid.

I didn’t grow up in some So Cal hellonearth, that’s part of the problem. I had a convivial suburban childhood, a responsible adolescence. I entered college studious, quiet, though I had at least acquired my Enid hair and goth-lite wardrobe. How embarrassing it would be to embark upon a freshman orientation-week life makeover! I wasn’t ready to fake out that bad. But by the onset of sophomore year it was high time to start taking things up a notch.

My liberal arts campus isn’t particularly arty, let alone experimental in any gender or queer direction. Still, it’s basically a tolerant place, and Matt stood out as one of our more experimental denizens.

Maybe it was being surrounded by so few openly gay people that made Matt a kind of Queer-of-all-trades. As far as his social persona went, he had a lot of the stereotypically effeminate Disco Fag traits; he understood girlie kitsch and all that, but he could take care of himself, and I always thought there was a lot of traditionally masculine energy radiating off him too. The proof, I suppose, is that so many girls didn’t just like him, they like-liked him. He could be some kind of Rupert Everett, the gay guy with the straight-appeal to be a Hollywood hunk or something.

I’d like to see him as James Bond someday. Damn.

But that wasn’t how he played it, at least around me. I was a mean little snarl of a black-bobbed Bitchie McBitch, or so I comforted myself, and I wanted Matthew to diversify my portfolio. I let him coax me into wearing vinyl leggings, take me clubbing. He really taught me how to dance, be social. He lightened my wardrobe, steered me towards neon-hued Chuck Taylors, fitted out my iPod with Eurodance songs. Around him I could be cheery, experimental. By the end of freshman year I was more sociable than I had dreamed of. I actually may have become something of a fun person, without losing my core edge of moroseness. Make that fake-moroseness. Well, I’ve gotta keep my edge, haven’t I?

“Girl,” I said to Matt over coffee and buttered rolls, “I am wilting away like some virginal Wharton heroine.”

“Sheila dear, why is it with the ‘girl’ this, ‘girl’ that to me but I can never call you ‘girl’?”

“Because you need to be told you’re a girl and I don’t. What I need affirmation on is being a slut and a whore.”

“So listen slut, isn’t Ted taking care of your business?”

“Oh, as far as the store front’s concerned better and better all the time.” I was getting well on with my Kegels, they made missionary sex exciting all over again. Ted’s not bad, mind you, but I felt like if one of us was going to start pulling more weight sexually, it was going to have to be me. Ted’s way too deep into his Feuerbach to take any hints about reading Tantric sex manuals. Fortunately for us both I’m still quite the studious girl.

“But I’d like to open up shop out back,” I continued wryly.

“Oh girl,” said Matthew, forgetting his manners, “you could be opening up a world of grief.”

“Oh god, you hypocrite!” I cried out. “Why the devil shouldn’t I expand my horizons?” I lowered my voice to a conspiratorial whisper. “You of all people ought to be ashamed, poo-pooing on anal like this!”

He gave me an appraising look. “Seriously, Sheila, no disrespect but I don’t know how straight girls can ever hope to love anal as long as they’re doing it with straight boys. I know Ted’s a nice guy and everything . . .”

“You don’t think he can be sensitive enough not to hurt me?”

“It’s more about knowledge, I guess. Experience. I mean–” he said, his eyebrows lifting up in that way they do when he’s feeling exuberant, I love the way it lifts his eyes so wide open– “all of my queenie take-it-in-the-ass bona fides notwithstanding, it’s a crap shoot out there.” I matched his eyebrow-arching, with as much irony as mirth. “Pun acknowledged, but not intended–“

“Bullshit. Pun totally intended,” I shot back.



“Sheila, don’t be a dork. I’m saying–“

“Why kaçak iddaa not ‘don’t be an asshole’?”

“Oh ha-ha-ha,” he said, getting tired of me.

“Why not, we have a theme going here!” I said poutily.

“Honey, I would want you to experience how great it can be–“

“Fucking in the ass?” I cued.

“Yes darling, how great getting fucked in the ass can be. But you need a knowledgeable partner for that. You need to be prepared, mentally, physically–“

“Oh Jesus, spare me Matthew. You just want to make sodomy another piece of arcana that gay boys can have a monopoly on. You taught me how to shop American Apparel,” I said appreciatively. “You could teach me how to do anal.”

He was quiet for a moment or two, then said, “Hey look, I mean, what do I look like here?” Meaning, who knows what?

“Are you seriously telling me,” I went on, “that here I am, your bestest Fag Hag and Straight Girl In Need of Guidance, and I’m inviting you to help makeover my life so that I can become a certifiable Anal Slut, and you are not willing to help me out? You should be jumping on this!– I mean this opportunity,” I added, when his eyes met mine in a curious way.

“Stop it,” he replied. “My dear, we’re not talking about you becoming an Anal Slut, we’re talking about you trying something out with Ted that’s going to be, like, a one-time variation in your lovemaking, one-time because probably neither of you will want it a second time.”

I was rather bothered by his attitude. Anything else he’d be all gung-ho for debauchery. Well, I figured, if he wasn’t fag enough for me, I’d have to be fag enough for the both of us.

“Listen bitch,” I said, “you are going to help me with this. I am on an anal project and you will share your expertise with me. You will draw upon your wealth of anal adventures, your craving for hard cock in your backdoor, and you will transmit all that lore and all that passion straight into me. Right, right here,” I said, theatrically snaking my hand back onto my tailbone, my middle finger parking in the top of my ass cleavage, “right into my tight little backdoor rosebud.”

He was grinning enthusiastically now. Really, I know how to be insistent when I need to be.

“This is Ass Training Week for Sheila,” I said. “And you, dear Matthew, are now my Anal Trainer.”


Once I made myself clear how serious I was, Matt quickly reverted to form just like I had hoped. That afternoon he dragged me off to a sex shop.

I was grateful I hadn’t been wearing any kind of Nu-Rave ensemble that day, I didn’t want to come off to any needy patrons like an Amsterdam whore. My pleated plaid skirt was of fairly modest length; today the safety pins sufficed for edginess. Or that was the plan when I rolled out of bed anyway. I hadn’t expected to go trolling for kinky implements. Oh well: carpe diem!

“Bitch, it’s time to enter the world of butt plugs. Or rather,” he added, cocking an eyebrow, “it is time for the world of butt plugs to enter you.”

Shit God, I thought to myself, once I got a good encyclopedic view of all the ass toys on the market. I began to wonder what I was really getting myself into. Into me. How far could this go? Matt, bless his heart, had been half-right at first after all.

“How would our little ass-tourist feel if her voyages were to wash this up into her shores?” he asked, wielding a monstrous rubber dildo in the shape of a forearm with its hand closed in a fist.

The look of affrighted astonishment I wore must have been something, for he suddenly looked all paternal and said reassuringly, “Oh sweetheart, most people would never insert this thing beyond the wrist.”

That hardly changed matters. I figured from below the wrist to the elbow was for show anyway. Hopefully.

I had diverted myself into admiring a row of glittery smooth dildos each about the length of a ballpoint pen when Matthew came up behind me and cleared his throat.

“We’ll use these,” he said decisively, holding up a set of butt plugs encased in clear plastic. ‘Anal Training Kit’ read the label.

“Uhmmm,” I began, as though trying to make a decision. But Matthew clarified that there was no decision to be made. “These will be perfect for you.”

“That big one looks a little–“

“Who wants to be an Anal Slut?” he demanded.

“Uhm, I do,” I said. Why the hell was I suddenly feeling so meek? The look of those black rubber toys and the look on Matthew’s chiseled brow made me feel so– I dunno, overpowered?

“And who needs to be an ass slut?” he added.

“Erm, I do.”

“You’re sure now?” he asked rhetorically. “We’re talking ‘need’ here. Stupid little girls,” he slowly added, “can get away with confusing ‘I need’ with ‘I wanna.’ But big girl ass sluts need to be clear about ‘want’ and ‘need.'”

Shit, I thought, what the hell smut book has he been reading? Goddamn, this was getting to me between my thighs in the old storefront. Was Matthew talking his sexy-talk to me?

I screwed up my courage and said as firmly as I could, “I kaçak bahis need to be a hot horny big girl ass slut. I need to open up my ass, yes sir!”

He grinned. “Right then. Come on.”

When he grabbed up the biggest squirt-dispenser bottle of lube I’d ever seen I got even wetter with my own natural lubricant. Christ, that thing was almost as big as the fist dildo. Was I really going to need all that?

As if reading my mind, Matthew said, “It never hurts to have too much.” A moment later he added, “And with too much, it never hurts!”


I kinda thought our little excursion was over when he paid the bill but he tagged back to my dorm with me and followed me into my room. Thoughtfully he had stashed the goodies into the canvas shopping bag he uses in the local organic grocery store.

I have a single with a neat little wash basin. After I used it Matt to my surprise starting giving it a scrub-out with some Bon Ami.

“What are you doing?”

“I’m making sure your sink is clean so I can give your toys a nice soaking,” he explained. “Good vigorous soaping up, then let them soak a bit in hot water, then rinse them off.”

“Goodness, you’re kinda anal about anal, ain’tcha?” I said, ridiculously.

He turned to me with an oddly warm but serious look. “Oh, yes. And I take your anus very seriously too, remember.”

I plopped down on my bed, feeling a bit weak-kneed. Matthew and I had always been plenty frank with each other, or so I thought. But maybe I hadn’t thought through how open I could stand to be with someone. I mean, Ted and I never spoke like this. I’d never quite had such sustained intimate talk with anyone about anything so– well, intimate. I mean, touching so intimately upon me.

“Now then,” Matthew began, “we need a schedule. We start with the little plug of course. Your ass training should begin tonight.”

“Oh, but today’s been so busy–” I began.

“Busy with what?” he asked. “Shopping for butt toys? Aren’t you eager to get started on your training?”

“Well, I–“

He laughed merrily. “No ‘buts’ young lady! Now then, I suggest after dinner you take a good dump, and then you’re going to lube up the smallest plug and wear it for one hour.”

“One hour?” I said. That seemed like a long time. Especially for an anal virgin.

“I could pretend to take your qualms seriously, and say ’15 minutes’ or some bullshit like that. But really, this thing is the width of a finger. A lady’s finger, at most.”

“Well,” I replied, feeling not at all intrepid about the prospect, “that’s easy for you to say, but I’ve never had a lady’s finger in my bottom before. Nor you for that matter, I imagine.”

He made a little ‘hmm’ noise meaning, who knows what? Then he went on, “All the same, it’s not going to hurt you at all. You’ll grow used to it very quickly. Really, if you were my slave or something I wouldn’t mickey-mouse around with this smallest plug at all.”

“Really?” I asked, genuinely curious. “Well what would you do?” I said, somewhat short of breath for some reason.

He looked thoughtful. “Well, really I’d– seriously?” I nodded. He grinned. “I guess I’d just lube up a couple of fingers, work one in and out for a bit, then insert two fingers, and I’d– then I’d lube up this middle plug and fit it in.”

“Shit! You think some beginner can get that thing in? On their first go?”

“Oh really now sweetie,” he said, reverting a bit to his Queer Eye mode. “That’s not such a major-sized toy. It’s average.”

“Average?” I exclaimed. “I figured that’s where we’d top this project out at.”

“What do you mean?” he challenged me, looking put out. “You think the biggest plug in the set is for show or something?”

I swallowed hard and said doubtfully, “Uhm, yeah.”

But he just burst out laughing. “Actually, no. As your Ass Coach I can assure you that in a week’s time you WILL be wearing the largest plug– and with pleasure too.”

I trotted out a couple of feeble, theatrical laughs.

He gave me a steely-eyed look. “What’s so funny?” he demanded quietly, not at all Queer Eye-like.

I blushed furiously, already feeling like an moron trying to squirm out of this with sophomoric humor. “Erm, ‘assure’ has the word, uh, ‘ass’ in it.” Idiot.

He nodded his head slowly from side to side. “We have our work cut out. Get up.”

“What, why–?”

“Get up Sheila.” I stood up. “Sheila, are you for real about this? You invited me to be your Ass Trainer and now–“


He studied me with a hard look. “We have to do something, to be real here.”

“What?” I squealed, not understanding.

“Hold out your hand. Your hand, Sheila dear, give me your–!”

I held out my left hand for him. I looked up at him, in the eyes, meekly. I’d be serious, I’d do as he said, I told myself. I willed my eyes to tell him the same, silently.

He held my look for a few seconds, then he reached for the bottle of lube. He took my offered hand by the wrist, lifted it up and squirted lube onto my fingers. “Work it around your illegal bahis first two fingers,” he said.

I did, my breathing hard and anxious. I willed my breathing to come quieter.

“You need to not be afraid about this, and you have to take your training– your ass training, seriously. If this isn’t a joke for us–for you– we have to be without shyness here,” he explained. “I want you to pull down your panties around your knees and rub that lube onto your anus.”

My mouth dropped open, ready to signal defiance, but I willed it closed. He was making sense. He was my best friend. This was my project, his project too. I had wanted him to be excited about it, to take it seriously. Now I needed to get real. I so wanted him to be pleased with me.

So I nodded my head ‘yes.’ I reached with my free hand and tugged my boy shorts down, crooking the wet fingers on my left hand so I could tug on that side too. Then I reached behind me, under my skirt, and rubbed the lube onto my butt hole. It felt crinkly at first, a dry little furrow. There were soft hairs there I had never acknowledged before. My face grimaced in thoughtless shame, but Matt smiled at me, warmly, without embarrassment. He was like a doctor or something. I rubbed around my rosebud, feeling it become slippy and suddenly not at all crinkly-like.

“Feels nice,” Matthew said, not as a question. “You haven’t really touched it before, have you?”

I only nodded my head, smiled, sniffed back a bit of snot in my nose, felt the hot on my cheeks. I kept rubbing my crack. It felt very natural to be doing this, somehow. Natural to be watched too.

Matthew continued to smile, beaming kindly. “Good,” he said, “now let’s give you some more lube.” I reached out my hand again, wondering if it would smell offensive or something; but I thought to myself, ‘get a grip, he knows all about this stuff, he likes it.’

He squirted more lube, generously. “Work that all around, make your finger slick. You know where it’s going.”

He put the bottle up and waited for me. Okay, I thought to myself, this is it. You’re gonna get used to this. I kept rubbing my thumb and first two fingers together. I hadn’t decided which would go in. I reached back again, this time holding the back of my skirt bunched up in my other hand. I wasn’t trying to flaunt my whole hinder but it didn’t seem like I should leave the skirt in my way either. Matthew could probably see some of the bottom curves from the side. What the heck, he doesn’t care right?

So I started rubbing again, just a bit more. My anus felt very relaxed, very smooth, inviting. Matthew looked on steadily, patient, his lips creased in a quiet smile. How charming he is, I thought to myself, as I eased my middle finger into my tail.

I went very slowly. From the kinds of things I read sometimes, I feared the slightest entry might make me scream with agony. But there was nothing like that. How silly! No, my virginal backdoor took my finger in to the first knuckle very patiently–welcoming it, in fact. It felt warm inside. Soft and hot, like my snatch. Tighter though. Nothing frightful or alien about it at all.

“Good?” he asked.

“It’s–nice,” I said.

“How far are you in?”

“Uhm, just at the first joint. Just the tip, you know?”

“That’s fine,” he said, very quietly. “Now go ahead and slide your finger in to the next joint.”

I did as he suggested. It went in so smooth. Like it was being sucked inside by this hot puckered mouth. A mouth I’d never opened before, till now. Damn. I felt like I was really accomplishing something. I started to giggle uncontrollably. It was so strange, like I felt so naughty but also like I was showing off an A+ report card or something. I’m afraid I was beaming rather goofily at Matthew, but he was such a sport. Our eyes were locked, basking together in this pleasurable moment that was really too odd for rational reflection.

“You okay?” he asked, and I made some emphatic “uhm hmm!” noise like I had my mouth full of a warm delicious brownie or something. “Slide it back out slowly, till just the very tip is inside, and slide it back in. Slowly now,” he intoned hypnotically as I did what he said, “and back in, back out, back in . . .”

Jesus, it felt so warm, so good. Unfamiliar tingles radiated out from my asshole through my body. There was nothing painful about it, only, a kind of convulsive edge to the sensation, not like I had to go to the toilet or something, just– this edge to the feeling. Once you’ve been touched back there you’ll know.

My finger and my ass were feeling such good friends. It was like my finger wasn’t the one doing the work, oddly. That tight little hole was like a vacuum, just sucking my finger inside, not wanting to let go as the digit slid out, still clasping it in its lubed-up embrace. Would it act the same with a cock?, I wondered. Would it suck in my butt plug like this? I would soon find out, I remembered edgily. I could feel my slickness in front, heavy now. I really felt like cupping my other hand over my snatch, squeezing my thighs down over it. But I was being watched. Shit. I couldn’t make myself think about it, only– he was there, watching me. Breathe quiet, I told myself. My asshole felt so nice and wet but my throat was so very dry.

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