Night of Debauchery Ch. 02

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Pushing the Envelope.
3.6k words
4.28
21.3k
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Part 2 of the 2 part series

Updated 09/22/2022
Created 06/03/2011
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hhorse
hhorse
16 Followers

Thanks to everybody for reading these stories. They were originally written for my entertainment, and to help various girlfriends cope with the lonely nights when I wasn't there to entertain them. There are more to come!

Also, thanks to my Literotica editor LissaSue, who is making my ramblings fit for human consumption.

Pushing the Envelope.

After their night of wild abandonment, the two lustful lovers had returned to their normal routine for a few days. One night, however, the conversation before bedtime turned to their recent adventure.

"So, you enjoyed our 'fun' the other night then?"

"Oh yes, I've been fantasizing about it a lot. In fact, I've been wanting to have another go!"

"Really? You do realize that what we did wasn't what you said you wanted to do? To explore your submissive side?"

"What do you mean? I was really submissive! The things we did were really kinky, erotic and a mega turn on!"

"Yes, but in all of that, you weren't submissive. You were dominated. You were tied up, blindfolded, gagged, and totally controlled. None of what happened involved you submitting and doing as I asked, without coercion. Each and every time you were tied up, you had no chance to resist. That isn't submission. That's being controlled, dominated, and forced. So which do you mean? Which one is it that really turns you on?"

"Well, you have a point, but I still meant what I said. I'm the submissive type. I want to be told what to do. The whole domination thing was great, but you are right - I want to try the other."

"Are you sure? It's a whole different thing; especially if we want to test how submissive you are, how far you'll go, and what you'll do. You've told me the things you won't do - and I wouldn't ask you to anyway, but are you still willing to skirt the edges of those limits? And to do it just because I ask you to; not because I've got you tied up and am just doing them to you?"

"Sounds good!"

"Okay then. Are you ready to find out for sure?"

"What? Now!? Well...yes, okay let's do it."

"Actually, you're the one who's going to do it. I suggest you start by stripping."

She slowly takes off her clothes, neatly folding them in a pile on the chair by the bed. Before long, she is naked, and asks, "What now?"

"Go in to the cupboard behind you. Pick out the nastiest, sluttiest clothing and put it on."

"What!? Why would I...oh...OK..." She turns and opens the cupboard to rifle through it, looking at each of the items inside; recognising them as most of the outfits he made her wear the last time they were in this room. Picking out a few items, she throws them on the bed. She looks at him, takes a deep breath, and puts them on bit by bit.

First, she slips on a pair of twin pearl-string knickers. She pulls them up tight until the strings disappear between her lips, eliciting a small moan. Then, she clips a pair of split nipple rings on to her nipples, making them instantly erect. Next, on goes a PVC half cup push-up bra, making her breasts stick up and beg for attention. After that, she wraps a corset around her middle, and hooks it up at the front. "Can you lace me up?" He goes and stands behind her, lacing the straps up from the bottom, and getting a grunt for each tightening pull on the straps.

A little breathless from the restricting corset, she sits down and runs a pair of fishnet hold-ups up her legs to halfway up her thighs. Then it's the footwear; she's chosen a pair of black ballet boots. She slips her left foot in to the first boot and starts to do it up. The first couple of holes tighten easily, but then she has to point her foot to start on the next ones. She does this slowly, getting higher and higher until she has them laced up to under her knee. Repeating the process with her right foot, she places her feet in bondage. The shoes have very long heels, and force her foot in to an arch so that her toes just a couple of inches from the point of the heel. She suspects they'll get uncomfortable before long, but they have the look she thinks is needed. For her arms, she picks up some long sleeved tube gloves, with just a loop for the middle finger. They reach up past her elbows to mid bicep. She pulls them on seductively and hooks the loops over each finger. She picks up the last item of clothing she took out of the cupboard. It's a ball gag. She stretches her mouth open, pushes the ball in between her teeth, then does up the straps under her chin and at the back of her head. Finally, she stands up and half teeters, half waddles over to her bag. Getting out the collar and leash she was given the other night, she puts it on around her neck. Having finished dressing, she staggers over to the four post bed and leans her back against one of the uprights, staring at him, and waiting his next demand.

"That's a good selection. I think you deserve a small reward!" He passes her a vibrator from the stash of toys, commanding "Rub your pussy with this." She rubs the nubby vibrator up and down her slit, the pearls of her panties proving no protection. Instead, they add to the effect, and she moans in pleasure. "Insert it up you, all the way until only the controls stick out." She does this, pushing it between the twin pearl strings, and closes her eyes in appreciation. "Turn it on to full." Although it's not the way she'd do things, she does as she is told. As she's starting to get turned on, her pussy is getting wetter, and going straight to full power like this was proving unexpectedly good. "Now push it in the rest of the way, so I can't see it. And keep it there." Pushing the toy in so deep it disappears from view, she realises that the only way she'll be able to keep it in is to squeeze her thighs together. She does so, concentrating hard on her unsteady feet and the sensations from within her.

"Bend over," he asks. She turns around and takes a few steps away from the bedpost; bending over and grabbing hold of it, she sticks her bottom out. "Wow! An opportunity not to miss." He walks up behind the girl and gives her left bum cheek a spank and then the right; then both together. He proceeds to spank her bottom until it has turned a delicious shade of pink, just visible below the material of her underwear. Her moans of pleasure show how turned on she's getting from the attention.

"Now squeeze the vibrator out of your pussy. I think you've had enough for now." Disappointed, she does as asked, bearing down on the vibrator in her depths and forcing it out of herself. He catches it, tossing it carelessly in to the toy stash.

"You know what – I think you've been doing a good job stretching out the entrance to your pussy, but I don't think you've been working on the depth or width of it. Lie down on the bed." With no idea of what was going to happen next, she turned around, sat on the bed, and scooted herself in to the middle of it. "Here, tie this tight around your waist."

She takes the satin tie he passes to her, tying one end of it around her waist, tight over the top of the also tightly cinched corset. "Move the knot around behind you, and pull the long bit out between your legs." Once again, she does as told, not entirely sure that being submissive in this way is what she had in mind. However, going ahead with his requests, she feels pleasure from them, from obeying his will.

"Here." He passes her a rubber dildo, a hose with a bulb coming from the bottom of it. Also, he gives her a bottle of slippery lubricant; with impeccable logic, she pours the gel on to the inflatable dildo, rubbing it thickly all over. Pulling her legs apart separates the pearl strings of her underwear, and she rubs the end of the toy up and down her slit a couple of times; then slides it in between the lip-rubbing pearl strings. After a couple of to and fros, the dildo is fully inserted in her, with only the hose sticking out. She looks at him, questioningly.

"Wrap the tie around the tube near the base of the dildo a couple of times." She does so. "Now, tie it to the front of the tie on your stomach." Having done this, the dildo is securely lodged in her. "Put your knees together, and tie them together with this." Another tie is presented to the sluttishly dressed submissive and she wraps it around her knees, tying it tight and further trapping the dildo in her pussy. He wipes her hands on a towel and places the bulb in her hand. "Give it ten full squeezes." The first eight squeezes barely register, but on the ninth and tenth she can feel the added size inside her pussy.

"Take the gag off, and then add another two squeezes." She performs her tasks, unbuckling and removing the gag; she then gives the bulb the two squeezes, feeling her pussy beginning to reach the largest limits she's ever taken it to. "Take my hand, and lick it." Taking the unusual request in stride, she licks his hand; paying attention to the whole of it, fingers, palm and thumb. "Now suck it." She sucks his fingers. "Now push my fingers to the back of your mouth and down your throat."

She baulks at this, exclaiming "What! Why should I do that?"

"I thought you were submissive and would do what I told you to?"

'Yeah, but that's not..."

"Well, do it anyway! I ask, you do – that's submission."

"Okay then..."

"Good then take my fingers and suck them down your throat until you gag." Pulling on his hand, she sucks his fingers deep in to her mouth until they go slightly down her throat and make her gag. She pulls them out. "Now, as punishment, three squeezes."

She shuts her eyes and grabs the pump, giving it one, two, and a third slow squeeze. "Oh my god, I can feel that. It's stretching me out! Oh, wow!"

"Good. Now be a good little slut, and take my dick out of my trousers."

Having unzipped his pants and taken his rock hard cock out, she gets her next instructions. "Suck the end." She rolls up his foreskin, licks the end of his penis, and then sucks the head of it in to her mouth, giving it suck after suck. "Good girl! Another squeeze."

Another squeeze causes another moan. "Oh, I feel full."

"Now, I want you to deep throat me. Pull me to you and down your throat until you have my whole dick down it."

With her lying down on the bed and him standing beside it, she finds it very easy. She grabs his bum and using it as leverage; she pushes and pulls him in and out of her mouth, then throat, until, eventually, she has him balls deep. She pushes him away, having completed her task. "Good. Now two more squeezes."

One squeeze - "Owwww, that aches."

"One more."

"Well, OK..." Squeeze. "Wooooooh, god, that's stretching me out."

"Mmmm. Good, that's exactly what we want. In fact, if you get one more squeeze out of it, we'll move on to your next test." She gives the bulb that last squeeze, shutting her eyes against the intensity of the stretching within her. "OK, you can release the valve." She does so, feeling her lower tummy deflate slightly as the monster dildo returns to a better size. "Untie the dildo, and then take it out." Having done as asked, she finds herself with an empty feeling, wondering what's next for her poor, tingly, demanding, and stretched vagina.

"I think we should up the ante a bit, don't you?"

"How do you mean?"

"Here." He hands her a small pile of clothes pegs. "I think you know what's coming next. Take off those rings and clip one to your right nipple."

"Mmmmm, that smarts! Ohhhhhh, more please!"

"Now, your left nipple."

"OK." She attaches the second peg to her left nipple. "Mmmmmmmmmmmm."

"Now, your left, and then your right pussy lip."

"But that'll hurt!"

"So what? Does it matter?"

"Well, no, but..."

"You know what; I think you're talking too much. Put the gag back on before the pegs." With a look of submission, she puts the gag back on, straps and all, and then pegs her left pussy lip, causing a gasp of indrawn breath round her gag. The right lip follows, with the same gasp. "Last peg, on your clit hood."

"Mmbbmblle."

"Do it!"

"MmmmMMmmMmmm." Clip. "MMMMmmMMMmmmmmmmMmmmMMMMMMMMM!"

He leans over and starts nibbling on his willing victim's neck, while groping the uncovered tops of her breasts. Grabbing the pegs on her nipples, he pulls them off, and then unpegs her lips and her clit hood. He then nibbles down her stomach to her pussy, where he gives her a good strong tongue bath. Fortunately, the gag in her mouth is keeping her from screaming out loud.

"Time for more I think. How are the boots?"

"Mmmbbl." She waves her hand to say so-so.

"Well, I think we need to take your mind off it! Let's not damage the PVC bed sheets. Stand on the floor, and we'll get on with it." She scoots off the bed, and stands by the side of it, looking incredibly horny. He pulls her pearl panties off, and holds her steady while she steps out of them. "Spread your legs a bit more...Yeah, there. Now, stay there while I get your next treat ready. Just keep your eyes ahead." The girl hears some scrambling behind her, then, "Look between your feet." Between her feet is a large, double stacked black pvc plug, glistening with lubricant and ready for fun. He reaches around her, groping her half cupped right breast with his left hand, and with his right hand he hooks three fingers in to her pussy and start to rub. She lets some of her weight fall on to his hands.

"So, ever had anything that large in you?" She shakes her head. "Kneel." She kneels down with her entrance hovering over the tip of the huge intruder. He reaches his hands under her bottom, and slipping three fingers from each hand in to her cavern, pulls her pussy lips apart. "Now, lower yourself on to it." The first two thirds slide in very easily, but his fingers get in the way. He pulls them out while stretching her lips outwards. She slides down all the way, right to the edge of the first mass.

"Want the rest?" Nod. "OK." He puts his hands on her shoulders and pushes down hard, popping the last part of the rim into her. She gasps deeply and starts to tremble. He reaches down and rubs her clit hard, as she starts to shimmy up and down, pushing the plug deeper in to herself, while moving her pussy on to the larger second lump. It doesn't take long before she orgasms hard, falling back into his arms, and letting the huge plug fall out of her on to the floor.

"I think you need a bit of time to recover before we go on." As she's kneeling there, he strokes his hands up and down her body, playing with her breasts, nibbling her neck, kissing her back and cuddling her.

Before long however, he asks, "Ready for more?"

"Mmbbble." Nod.

"Great! I think I've been ignoring your bum hole for waaay too long. It fit in your pussy, so, by the end of the evening, shall we see if we can get the plug in your ass?" A slight hesitation, then a nod. "Good. Kneel on the bed." The girl turns round and crawls onto the bed. She kneels in the middle of the PVC clad bed. "Put your head on the bed, stick your bum out, and spread your knees." She complies, sticking her bum out and wiggling it. "Hold your cheeks apart." She reaches back and pulls her ass wide. He lubes up another toy and presses it to her hole. "Push back." Getting excited again, she pushes back, feeling the toy start to invade her nether privates. "Push back harder. We're not going to get very far if you don't throw yourself into it!" She pulls forwards and pushes back hard, impaling herself on what turns out to be the first of several ripples on the toy he's using on her. She pulls away and pushes back again. And again. And again. Before long another, larger ripple pops in to her. He pulls it all out again in one motion. "Again." He puts the tip of the toy to her hole, and she pushes back onto the second ripple without a wince. "Well, well. That's it for width. How about some depth?"

A nod of the head is all the encouragement he needs. He gets another toy out of the toy box and lubes it up. Seconds later, it is at her butt hole, lubed and ready for her. "Push back." The head pops in past her ring, and half way in. "Do you know what it is you have in you now?" A shake of the head. "Well, you know how you said no animals?" - A sudden panicky squirm. "Don't worry! It's just a dildo, but it's a mold of a dog. The same shape but rubber." Acquiescence, and a push back, shows how kinky and what a turn on she finds the idea. The toy slides in up to the impediment at its base. "You know what's unique about a dog's willy?" Shake "It has a large lump at the base. Push back and you'll see what I mean." She pushes back, the lump touching her ring, stretching it. She pushes back harder and harder and then pulls forward. He pours more lube on the toy, and she pushes back again, swallowing the whole thing up her, despite its size and length. "Push it out again." She ejects it out of herself, giving a huge moan of pleasure, and then she pushes back again, taking it all back in. And out again. On the third time, she gives a huge shudder, cumming from the anal stimulation and falling on her side.

"Hey there, don't give up now; we have the big plug to go for next!" A faint nod is all the indication she gives. "Well, it's still on the floor, & lubed up, ready to go." She gets off the bed, really unsteadily now. The ballet boots are not allowing her much control at all. She almost falls to her knees, well aimed. The plug touches her anal ring, and she pauses. "Tell you what. I'm going to give you a choice. You either take the whole of the first plug, or we do something right outside your comfort zone." She thinks for a moment, and then tries to slide herself on to the toy. She gets about two thirds of the way on to it, then stalls. "Would you like me to help you?" A shake of the head. "You know what that means then, don't you?" A nod. "OK then, your choice. Get off there and sit on the edge of the bed."

Her head bowed at failing her task, she sits on the side of the bed, wondering what's in store for her, knowing it will be something she's never done or considered before. Also knowing she'll do it to herself, but under his instructions.

"Here. Wipe your nipples with these." He passes her a couple of wipes, which she uses to clean her hard nubs with. "Here, now hold these against your nipples." He passes her a couple of ice cubes, held in cloth. The girl rubs the cubes over her aureoles, and her nipples. Then, holding them against her breast tips they slowly turn numb. Her pussy starts to drip and flow on to the bed. "Are they numb?" A nod. He passes her a pair of piercing forceps. "Take these and choose a breast that we're going to play with." She glances at her left breast, then her right. She supports her half-cupped right breast with her right hand and clamps the metal device to her nipple. She doesn't feel a thing.

"Are you ready?" Looking straight in to his eyes, she takes she ultra-fine needle he is holding out to her; places it at one side of her nipple, she pushes it through. A gasp through the gag is all the reaction she gives, the ice having done the trick, and the fine needle meeting no resistance. She unclamps the forceps; at which point, he pushes her down on the bed, sticks his head between her legs, and eats out her shaven pussy. Mixed with the endorphins of her recent experience, the needle still in her, and the lips and tongue on her nether regions, he shoves her in to a wrenching orgasm.

More to follow!

hhorse
hhorse
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