“Finish off the wine,” I tell her, pouring the remains of the bottle into her glass.
I need to keep my wits about me, maintain control, whereas she … Well, a little hazy warmth from the wine mixed with the fear I know she’s feeling should ease her submission. Emily’s a nice girl, prim and proper, or was until she met me. But she’s learning fast.
I glance across at her as she takes little sips from her wineglass. She’s apprehensive, too upright in her seat, her wary gaze following my every move. I know she’s been thinking about the evening ahead all day, wondering if I really mean to do it, what it will feel like, whether she’ll be able to stand it. Giving her two days grace to contemplate her punishment was a masterstroke.
She’s made a special effort to please me tonight, maybe hoping to escape her punishment altogether. She’s wearing her “fuck me” dress, form fitting to the waist but with a loose, flowing skirt that ends mid-thigh. It exposes her wonderful long, brown legs and accentuates the glorious shape of her tits while still managing to look perfectly demure. It’s always worn without panties so I can just toss the skirt up round her waist and take her anytime I like.
A row of tiny buttons fastens the bodice. I feast my eyes on her nipples, erect already, pressing insistently against the silky fabric. She’s watching me watching her, twirling a thick strand of her long blonde hair in one hand, clutching the stem of her wineglass in the other. My waiting game has aroused her – her cheeks are flushed, her breathing slightly stilted. I bet her cunt lips are already wet, pouting open as she watches me and wonders what it’s going to feel like. Will it be mostly pleasure and some pain, or mostly pain and only a little pleasure?
A mixture, I hope. This is supposed to be a punishment, after all. I want her to struggle and beg me to stop. I’ve never asked her to submit to it before, just hinted that the time will come, that it’s something I intend to do. And two nights ago I got my chance. She stayed out late with her girlfriends. Came home two hours later than we agreed and unsuitably drunk for a nice young lady. Dangerously relaxed, she failed to notice my displeasure and worsened her crime by giggling about the fun they’d had and what a hunk the new barman was.
She almost fell over trying to undress, and littered her clothes all over the floor. Roused from sleep, I watched her until she finished in the bathroom and came to bed.
“You’ve been a bad girl tonight, Emily.”
She reached out to embrace me, but I grasped her hands in mine and held them above her head, looking down into her glittering eyes. “You’ll have to be punished.”
She giggled. “Now?”
“Not tonight Emily. I want to go back to sleep. But you’ve been a very bad girl. I’ll need to think of a more severe punishment than usual.” Her gaze flickered uncertainly over my face. “What? Please tell me, Rob. I’m sorry if I’ve annoyed you.”
“Good. You’ll be even sorrier on Sunday night.”
“What are you going to do?”
“Punish you. Properly.”
I could see her mind working as she digested this. I knew where her imagination would be taking her. Probably a beating, spread-eagled across the bed with her arms and legs tied, or possibly stretched out on the kitchen table, her pink and delectable bottom exposed over the edge, feet wide apart on the floor.
“No, not that,” I said after a moment.
Her eyes widened and she gave a little giggle. “What then?” I watched her run through the other punishments I’ve introduced her to. “Anal then, with the big dildo in my pussy?” she suggested. “What Rob. And why wait till Sunday?”
“So you can savour your punishment properly, my love. Anticipate it thoroughly. This is going to be something new, Emily. Different.” I heard her breathing hitch. My cock was rock hard just thinking about her sweet submission, the cries of shock and discomfort I knew she’d make. “Much more challenging,” I whispered. “A proper punishment for a very bad girl.”
“What? Please tell me Rob.”
I reached beneath the bedcovers. Of course she knew better than to come to bed with anything on. When I trailed my fingertips down her thighs, she obediently spread them, turned on by thought of her punishment, no doubt. I opened her pussy lips and probed her wetness. She relaxed her legs, opening herself fully. I trailed my fingertips across her clit and then lifted them away, wringing a little groan from her lips.
“You’ll be groaning like that all the time on Sunday,” I told her. “And moaning, begging me to stop, to go slowly. I expect I’ll get a few screams too, for all the good they do you. Can you guess what I’m going to do, Emily?”
She shook her head back and forth on the pillow.
“I’m going to fist you. You’re going to take my whole hand inside your dripping wet, hungry little pussy.”
For a moment there was silence. Then her voice broke. “No, Rob. Please, you can’t. You’ll never fit.”
“Oh, I’ll fit. Eventually.”
“You won’t! You’ll hurt me.”
“A little, I expect. It’s meant as a punishment, after all. And it would be unreasonable not to expect it to hurt a little, being stretched wide open like that. But it’ll turn you on as well, knowing that tight little hole of yours is wrapped around my wrist. You’ll get hot and wet and slick until you beg me to make you come.”
“I won’t.”
“I promise you, you will. I’ve done it before, so you’ll be in the hands of an expert, or rather the hands of an expert will be in you.”
“I’m begging you Rob. Please don’t. I’ll do anything else.”
“Be careful Emily. You know your punishment will be worse if you beg me to stop. Go to sleep before I get really angry. And make sure you’re ready for me on Sunday night.”
So here we are. Almost time to begin. My cock is getting harder with every passing moment, my trousers damp and sticky with pre-come. Fisting sweet little Emily is going to be so hot. It’s a while since I’ve had a girl impaled on my hand, but it’s a sight I can remember as though it was yesterday. My wrist, sticking out of her pussy, her pink lips stretched like a tight seal around it, my fingers moving around inside her hot, wet tunnel. And her moans, her entreaties to stop, to end her torment. Her sweet cries of pain and pleasure as my hand forced its way excruciatingly slowly inside her. And she was a real slut, not a nice young lady like Emily.
Suddenly impatient, I get to my feet. “Time to get ready for me baby. Up you go.”
Huge, pleading blue eyes scan my face. She’s wondering if I will relent, but arousal is making my expression hard and forbidding. Her gaze drifts away.
“Where do you want me.”
“In the armchair, I think. You can keep your dress on.” When I follow her upstairs a few minutes later, she’s sprawled there already, like a good, well trained girl, ready for her punishment. It’s a big, old-fashioned, tub-style armchair and she knows how to sit in it. Bottom forward, right on the edge, cunt and asshole accessible. She’s draped a thigh across each arm, spreading herself wide open the way I taught her. Her dress is scrunched up around her waist. No panties, of course – she knows that coyness always attracts a far worse punishment. And what’s to come is bad enough, although the dread I know she’s feeling hasn’t obliterated her excitement. Her pussy lips are wet already, slightly parted and glistening with arousal. She watches me carefully as I stand before her, examining her exposed body with a lazy smile.
“Tell me, Emily. Am I going to need to restrain you?”
“No,” she whimpers. “I’ll try to be good.”
“Excellent.” I focus my gaze intently between her widespread thighs. “I see you’re looking forward to your punishment.”
“No!” she exclaims. “I don’t want you to do this, Rob. I’m frightened.”
“You’re meant to be frightened.”
I go to the bedside table and remove the bottle of lubricant from the drawer. Emily’s wide eyes follow my every move. She’s burning up with anticipation and fear, her body tense but her pussy lips pouting out towards me as I kneel down between her legs.
“Ready, Emily? Pleasure first, while I get you really wet and start to open you up. I suggest you try to enjoy this bit.”
A little moan escapes her lips as I run my fingers down her slit. Wetness is gathering behind her lips. It spills out when I part them, pulling them wide and spreading the warm wetness around them, down the baby-soft skin of her inner thighs and across her tightly puckered anus.
“This is going to be good, Emily. You’re so hot.”
It turns her on, spreading that wetness all over her thighs and vulva, so I use all four fingers of my right hand to do that while my left one plays with her clit. I coax it out of its hood and then suck it hard into my mouth until her groans are coming thick and fast.
More and more wetness is sliding out of her. I just know she’s going to take my whole hand like the obedient little slut she is. It only takes a few minutes until she’s nearly coming. She’s thrusting her hips upwards to keep my mouth in contact with her clit and throwing her head from side to side, moaning in ecstasy.
“Ready to begin, Emily? I’m going to start stretching that sweet little pussy hole open, a bit at a time.”
“Please don’t hurt me,” she begs.
I insert two fingers of my right hand deep inside her, pushing them in until they slide behind her cervix and then thrusting them in and out, harder and harder. With my left hand I stroke her clit, enough to keep her close to coming, but never quite able to get there.
“Nice?”
“Yes. More.”
“More fingers? You can’t have more clit or you’ll come, and you’re not allowed to do that until my whole hand is inside you.”
She groans. “Please … ”
“Please what? A third finger?”
“Yes!” she shouts as I pull my fingers out slowly, spreading the sticky mess that comes with them around the entrance to her tight pink hole. I remove my other hand too – no more playing with her clit until she really needs it, when I’m pushing in deep, stretching her wide.
She screams with pleasure when I shove three fingers hard and deep inside her pussy. Her head falls back, her eyes close.
“God, that’s so good. Don’t stop.”
“I won’t. I intend to carry on until all of this hand is buried deep inside you. Time for four fingers now, I think. And look at me, Emily. I want to watch your face while I stretch you.”
I slowly insert my little finger into her dripping pussy alongside the three already holding it open. She gives a little gasp at the invasion, but soon settles down, her hips mirroring every movement of my hand as I stab my four fingers up inside her repeatedly. When she’s pouring wetness across my hand, I start stroking her throbbing clit again, wanting her to feel delicious pleasure mixed in with the pain that’s about to begin.
She’s moaning with pleasure and on the verge of coming when I ease my four fingers deeper, pressing into her depths and forcing her tight little fuckhole wider for my knuckles. Her excitement recedes with the increased pressure inside her, her soft moans turning into gasps and little cries as I open her wider than she’s ever been before.
When four fingers are in to the knuckle, I coat the rest of my hand with lubricant and slip my thumb inside her, feeling my way into her tight little hole until it slides in alongside my fingers. I begin to push inwards, and pain and fear abruptly break though the haze of Emily’s pleasure. She’s starting to struggle when I pull my hand back out again, easing the juices from her pussy to lubricate her even more. When I push back in earnest, twisting my fingers and thumb in her tight entrance, she can’t hold back.
“I don’t like this Rob. It hurts.”
I give her a stinging slap on the inner thigh. “You’re going to take my fist, Emily, like it or not. If you can’t lie still, I’ll tie you down.”
She quietens, sucking her bottom lip between her small white teeth as I step up the stroking of her clit and ease my hand gently in and out of her sopping cunt.
“Nearly there, Emily. Open wide.”
“Aaaah,” she gasps, as I ease deeper still, pushing further into her straining entrance. Only the widest part, the base of my thumb is still outside her. My knuckles are stretching her entrance. I stop pushing, giving her a moment to adjust.
I slowly twist my fist around inside her entrance, stroking her clit all the time. Emily’s groans and cries are coming thick and fast now, an almost inhuman sound. This must be hurting, for she’s not coming despite almost constant stroking of her clit. Her knuckles are white where she’s clutching the arms of the chair.
“Watch me while I’m doing this, Emily.”
She’s so lost in pleasure/pain that I have to shout to get her attention. “I want you to watch my hand as it opens you wide.”
“I don’t like this, Rob.”
“Yes you do. You’re so wet, Emily, I think you’re almost enjoying your punishment.”
“No! It hurts, Rob. Please stop! Aaaagh”
“Keep watching, and tell me what you feel, Emily.”
She tries to obey and look between her legs, where most of my hand is embedded between her widespread lips, but she can’t. “It feels … I can feel you stretching me. It burns. I don’t like it – ” she finishes on a little scream.
“Nearly there, Emily.” I twist my hand round and round, then ease it in and out, in and out, torturing her wide-open hole. Her head is thrown back, mouth open, her legs rigid around each chair arm. I squirt a little more lubricant onto the rest of my hand where it protrudes from her cunt.
“Nearly there, Emily. Open wide for me, baby.”
Holding her clitoris firmly between thumb and forefinger, I ease out of her one last time and then push back firmly, twisting and easing my right hand deep inside her. Emily’s long moan of terror rings in my ears as my fist slides slowly inwards, pushing further and further.
The moan turn to a scream as the base of my thumb passes through her desperately stretched opening and the rest of my hand slides in behind it. She’s wide open, throbbing around my wrist, her cunt a velvet vice about my hand. Her internal muscles grip me so tight I don’t think I could get my hand out if I tried.
“Emily? I want to know how it feels.”
Tears of pain and frustration glitter in her eyes when she opens them to look at me. The sight of my wrist protruding from her tight little cunt is so amazing.
She glances down between her legs for a second. Then her head falls back.
“Oh God … ”
“Tell me what you feel, Emily.”
“Stretched so wide, so tight. It hurts, Rob.”
I stroke her clit very, very gently. “You sure?”
She thinks about it for a moment. “It hurt horribly to begin with, when you were twisting and pushing, but now… now … it’s just uncomfortable. I feel uncomfortably stretched.”
“Good. That’s how it should feel. This is a punishment, remember.”
“Are you going to take it out now?” she says. It’s a struggle not to laugh at the hope and desperation in her tone.
“No, or at least not all the way out.”
“What, then? What happens now?”
Her eyes are huge with shock, her voice a rising wail. Poor little Emily thought it was all over, her punishment complete.
“I start to fist you.” I twist my fist a little to give her a taste of what’s to come.
Her eyes widen even further. “You start to fist … what have you been doing up to now?”
“Just opening you wide, making you take me. The fisting proper starts now, my good little slut.” I return my left hand to her swollen clitoris, dragging each fingertip in turn across the throbbing flesh. Her internal muscles squeeze me even harder. She’s clinging to my hand, oh so wet and oh so tight.
“The best is yet to come, Emily. First, I’m going to give you a long, slow, thorough fisting, like this … ”
I pull the fist partway out, and before she can draw breath to express her relief, plunge it back in again. Her soft scream is music to my ears. I stroke her clitoris again until she starts to moan.
“And in between fisting you in and out, like that, I’ll move my hand around, like this … ”
I wriggle my fingers deep inside her, pushing against the slimy walls of her cunt and easing my fingers apart, opening her even wider. A low groan is torn from her throat.
“Or like this, maybe … ”
I twist my hand round inside her, very slowly, first to the left and then to the right.
Her breath catches on a sudden cry. “I can’t take this, Rob!”
“You can Emily. You will. And then I’ll make you come. Come around my fist, come with it buried deep inside you. And you’ll love it Emily. I’ll feel you squeezing my hand tight, and you’ll feel your muscles cramp around me, huge inside you. And you’ll know it’s the best, most intense orgasm you’ve ever had.”
“And then you’ll stop?”
I shake my head, delighted at the ridiculous hope I see in her expression.
“Oh no, Emily. Then I’ll start. Start to take it out.”
I can see her trying to work out what I mean. “Start? How?”
I give a little tug on my hand and watch her eyes widen. “You feel how tightly I’m held inside you? The widest part of my hand and all my fingers have to come out through your tight little hole again. Just think, Emily. If I hold my fingers apart and pull out, very, very slowly, an inch at a time – what might that do to you?”
I wait for this to sink in and then gently twist my fist inside her again. “I might make you come again as I hold my fingers wide apart and ease my hand slowly out, stroking that swollen little clit of yours at the same time. I think that might hurt. Would you like that, Emily?”
A low cry is my only answer as I slowly start to work my fist in and out of her straining pussy. That’s the secret with Emily. Just when you’ve made her believe that the worst is over and she’s got nothing left to fear, you expand her horizons a little further.
— end —