Babysitter Bondage All Grown Up (M/F)

Post your story here to be critiqued and praised.
User avatar
icedteacool
Unfettered Newbie
Posts: 3
Joined: 19 Aug 2018, 17:34
Location: NC

Babysitter Bondage All Grown Up (M/F)

Unread post by icedteacool »

You always hear about that fantasy of tying up the babysitter... but what about the innocent girl you used to babysit?

--

It was a regular day, almost like any other. I was just happy to be visiting for the holidays around Easter time outside the city and seeing old family and friends. Almost fortunately, I had arrived on a day when no one was home - everyone was away for the next two days because of a cancelled flight from the Bahamas, so I would get some much needed time to relax and decompress before the family arrived home.

As I unpacked, I noticed that I had subconsciously brought a roll of microfoam tape and some rope - things I always pack just in case that good bondage opportunity arises and I get in the mood, so to speak. I chuckled to myself and began to watch TV as I unpack the remainder of my items. I put in a call for a pizza (nothing beats a NY pie, after all!) and kick pack and relax.

*Ring ring!* - the apartment doorbell sounds just a half hour into my relaxation time. "Hmm, must be the pizza!" I exclaim to myself and jump downstairs. As I tip the driver and smell my delicious goodness, I hear a voice calling, "Nate, is that you?!" It is dark in the stairwell and I cannot see all too clearly, but eventually I begin to make out the figure and shape of "Brittany", a girl who I had babysat a long, long time ago.

"Brittany, is that you!? Wow, all grown up, huh?" I say laughing. She's 5'4, brown hair, brown eyes... almost the way I remembered her but all grown up.

"You're not so bad looking yourself!" she smiles. "But hey, you're back?"

"Just temporarily, visiting the fam," I say, checking out her perky butt and her breasts, which has become to fill in. I almost smack myself in the head... *What are you doing Nate!? She's too young! Snap out of it!* "So Brit, how old are you now? 17? 18?"

"I just turned 18 last month!" she exclaimed, jumping up just enough for her sweater to slightly reveal the pink bra she was wearing. "It's great to see you back, Nate. Maybe we can hang out later and catch up?"

"Uh, sure... I'll see you later!" I say as I leave, not giving her my cell or contact info, hoping not to be tempted. Much to my surprise, Brittany slaps my butt as I walk past her, and she winks and smiles, and I do my best to ignore her.

It doesn't take much to get Brittany out of my mind. A few bites of my favourite pizza and I'm in heaven. She sure would look great all bound and gagged for me... but still, not worth it, even if she was coming on to me. And anyways, I hadn't tied anyone that young since I was in college! I erred on the side of not being a creeper and open my computer to watch some Hulu along with my meal, when all of a sudden I see a notification for a friend request from... who else... Brittany. Well... peeking at her photos and accepting a friend request isn't too terrible... I think to myself but again think better of it and simply accept and begin to watch my show. *DING!* a notification from Facebook again, this time some messages from Brittany.

I open them up to find Brittany sending me a selfie and saying hello and asking when we could hang out. I reply that I am busy at the moment and maybe later on the next day. Brittany responds with a sad emoji and I get back to my show. Sever minutes pass before another message arrives, this time with Brittany asking if I remembered how much fun it was to babysit her and hang out when we were younger. I replied with a simple thumbs up and "Yeah, those were the times!" and resume watching. *Ding!* This time, the message reads, "You know Nate, I've always had a crush on you..." but at this point, I resist and ignore the urge to respond.

At the end of my show a half hour later, I get another message. This time, Brittany is just in her pink bra and panties and I flip out, asking her if she wants her father to come around looking for me. Clearly, this tactic worked, because she did not respond, but I had to admit, the urge and my massive erection had me feeling quite some way. Hmmm... maybe she deserves to be punished in some way... all those times I watched bondage pics at her house as I waited for her parents to get home, maybe she saw me and knows something...

By the time evening sets in, I hear a knock at my door. Wondering if it's one of the neighbors, I open without looking and Brittany barges in. She's wearing a pink shirt now and just some denim shorts. "Brittany... what are you doing here!? I feel really uncomfortable right now. You should probably just leave."

"Nate... I'm sorry I sent you that pic... it was inappropriate of me, but... I have had a huge crush on you ever since you babysat me all those years ago... and I really just want to hang out. Don't worry, I'm not a virgin, and I won't jump on you, but I do want to hang out... please?"

At this point, I'm just like, Screw it, what's the worst that could happen? Better to entertain Brittany than to chance it that she's a psycho who'll get me in trouble if I don't appease her, so may as well. "Fine, want some pizza?"

An hour passes and I begin to clean up. As I lift one corner of the pizza box, I see that I had left the rope and microfoam tape out in the middle of the table in plain view. I try to quickly put them away before Brittany sees them, but alack and alas...

"Nate... what's that rope and tape for? I've never seen tape like that! Can I see?!"

"My my... you're quite inquisitive, huh?" I toss it over to her.

"Mhm, it's so soft and stretchy!" she exclaims. "What do you use it for?"

"It's actually medical tape, it's soft and stretchy and can be wound around wounds to bandage them and compress them, but it's not too sticky."

"Oh fun! Nate... what's the rope for then?"

"Oh, I don't know why that's there, just a tow rope probably..."

"Nate, tow ropes aren't white and made of silk... Why don't you tell me what's it's really for? I can keep a secret..." she winks.

At this point, all I can think of right now is, Are you kidding me?! I humor her and retort, "Well if you're so smart, what do YOU think it's for?"

"Hmm... well... I think this is bondage rope."

I nearly spit out the beer I was drinking. "Brittany... how do you know about that kind of stuff?"

"Oh Nate, I love bondage! I spied you after bed one time and have been curious about it for years. I've tied myself up a few times, but never been tied or gagged by a man... Maybe you could show me? Just for a few minutes? Please?!"

Again, weighing my options, I consider that A) Brittany would be off to college soon and if I kept her clothes on maybe things would not get too out of hand, and B) if I did not give in she might tell someone about how her male babysitter looked at naughty pictures while she was sleeping. I opted for A.

"Fine, but clothes stay on, ok?"

She smiles and put her wrists out in front. "Oh no, these are going behind your back," I say as I grab them and begin roping them together. "Ever been hogtied in your self bondage adventures?"

"Oh no, I've never been able to do it tight enough!"

"Well, here's a good opportunity for you to experience one... let's see just how flexible you are..." I say as I also rope together her elbows and cinch the rope tight. I then grab her feet and tie her ankles together over her socks, figuring that was the best way to avoid rope marks. I then grab more rope and complete the tight hogtie by tightening it and tying her ankles to her wrists. "How's that?"

Brittany kicks and struggles for a bit before realizing that this was quickly inescapable and that it was tighter than any self bondage she had experienced till now. "It's tight! Mhmm! Can't get loose at all or reach the knots!" "Beats self bondage by a mile, doesn't it?" I say as I grab her chin so that she and I lock eyes for a brief moment, and we both crack a smile.

"You know... Nate, I might start screaming... isn't there something you're forgetting?"

"Well, we wouldn't want that now would we? What kind of gags have you been practicing with?"

"Oh you know, cleave gags, duct tape, nothing crazy... it's not like I have access to a lot of bondage gear!"

"Well, let's give you a taste of this microfoam tape for starters. It's nice and sexy.. I'm sure you'll fall in love with it instantly," I say as I tear off two wide strips and cut them with scissors. "Lips together please!"

Brittany purses her lips together and with eager eyes wide open accepts her gag as I plaster on one strip, smoothing it over her pretty little lips, and apply one more for good measure. The gag shows off the outline of her lips and her mouth, and Brittany playfully mmphs to play along.

"Of course, you could probably work that gag off pretty easily, but we won't get too crazy tonite. Something else that we might want to do though.." I say as I eye her perky little breasts underneath her shirt. I untie her elbow rope, loosening her bonds a bit, and begin to instead tie her arms together above the elbows but below the shoulders. I wrap the rope around her chest, above and below her breasts in a criss-cross patter, and finish it off by cinching it off tight, creating a rudimentary but effective breast harness. Through her gag, Brittany pleads, "Mmmh! MMMh I eee?"

She nods over to her phone to take a picture. I refuse but hold up her phone in selfie mode so she can check her self out. Brittany begins struggling for herself, and I notice she begins to rub her crotch on the couch.

"Beginning to enjoy ourselves, are we? Well, I am going to grab a quick shower, but I think I'll leave you to struggle for a bit longer before bed, okay? Just don't enjoy yourself TOO much," I say as I playfully spank her butt on each cheer a couple of times. Brittany simply looks up at my and smiles underneath her tape gag as she watches me enter the restroom.

As I am in the shower, I can hear Brittany's playful mmphs through the lackluster tape gag, clearly egging me on to help her with her bondage experience. At this point in time, I begin to think to myself, Eh, what's the worst that can happen? I won't touch her, she can just play with herself and I will let her go. I would have killed to have a fantasy come true like this...

I exit the shower and put on just some shorts and grab Brittany's chin and look into her eyes. "So, you're enjoying this huh?" She nods and smiles beneath her tape gag. "I am going to take the tape off your mouth, but no screaming, ok?" Again, she smiles and nods in agreement. I peel the tape gently off her lips. "So, what else have you seen online that you would like to try? I think I have enough rope to give you a crotchrope and you can play with yourself that way..."

Immediately, Brittany gets excited. "Oh Nate of course please please please mmmph!" I clamp my hand over Brittany’s mouth. "What did I say about yelling and screaming? Clearly you cannot be trusted and we'll need to figure out a better gag for that young pretty mouth of yours. Typically I would yank off your panties, but for now this will have to do," I say as with my other hand I rummage through Brittany’s bag and find a thong. "Well, never mind! Looks like we'll be shoving undies in that mouth after all. Now say 'Ahh' and open wide!"

Brittany complies and opens her mouth, playfully licking her lips with her pink tongue as I insert the fabric into her willing mouth. I prod the thong all the way in, filling her small cheeks. I cup her chin, prompting her to close her mouth to be sealed by the microfoam tape. I expertly rip off several strips, and cover her entire lower jaw with shiny, stretchy tape. I can still see her pretty little lips through the gag, and playfully give her a little kiss through the gag. Brittany lets out an excited mewl, but the gag holds her moans in check.

I begin to undo Brittany's denim shorts and pull them down just enough to work the crotchrope snuggly into place on top of her undies. I cinch it off tight and attach a rope to her bound wrists, giving her no slack so any movement or struggling would prompt the crotchrope to do its work.

"There, now you can properly enjoy yourself," I say as I re-examine the bonds one more time. "You have half an hour to escape, although I very much doubt that you have any interest in escaping..." I say as I notice Brittany slowly begin to enjoy herself in her bondage. Her mmmphs begin to increase in their intensity, gradually growing as Brittany began to enjoy a wave of orgasms, followed by a sigh and a fluttering of the eyelids as she reached climax.

All the while I just watch, thinking to myself how great it was to be carefree at her age and how many girls I had tied up back then.

"Well, it's been over half an hour and you're still not loose! You're not a very good escape artist, are you?" I say as she rolls her eyes. I undo one of the knots to let her gradually get herself free from the ropes. I watch as she picks at the knots, one by one, until finally she is free from her crotchrope, then her breast harness, and then the rest of her bondage. She peels off her tape gag and spits her thong out on the floor. "Thanks Nate, I really appreciate it. Don't worry, I won't tell anyone... it can be our little secret. Maybe in a few years you'll make a real woman out of me yet!" she said as my eyes must have popped out of my head.

"One step at a time Brittany," I laugh. "Here, enjoy, you can keep the rope and tape," I say as I put the supplies into a bag and watch her exit the apartment. Wow... I think to myself, I am a complete enabler, and I turn on the TV and switch to baseball and wonder just where this experience will take Brittany on her future kinky endeavors.

My answer would be expeditiously forthcoming. I had only gotten through a couple innings when a message illuminates my phone. The screen indicates an image message from Brittany. I try to restrain myself from opening it, but given that it was an especially quiet night, I figured I could use the entertainment. I get rock-hard as I view the image of Brittany, who (now fully nude in the photo) had apparently plastered more tape over her lips and was winking with a smile as she held a large, glass clear ribbed dildo in her outstretched hand, with her index finger motioning as if inviting me to come over.

Then I read the message: "Mmmph! I'm home alone for the night. Door's unlocked ;)"

I could use some entertainment, but I could use some company, too, I smiled as I begun to gather additional supplies and planning my night.

I could barely contain my excitement at the prospects that my evening and night held in store for me. Not only did I now have a semi-legitimate excuse to skip out on being around the family, I also would have a very sexy, pretty girl who was all curious about bondage and I was the one who got to show her some of the ropes.

As I rummaged through the house for some additional materials (it seemed Brittany had already begun to amass a toy collection of her own, a considerable one for her age, but I was not planning on taking any risks of running out of binding materials), I became painfully aware of how inadequate my supplies were in contrast to my rather substantial collection at home, stemming from years of bondage addiction. I found some more rope, two rolls of silver duct tape, a few rolls of black electrical tape, and some saran wrap.

I placed all of the items in a backpack. It'll have to do for now, I thought to myself as I also grabbed my computer and locked the door behind me. Brittany's family apartment was on the first floor. I made my way down the stairs and, just as promised, found the door unlocked. I hear soft mewling and mmphing coming from one of the bedrooms. I lock the door behind me, and playfully knock on the door. As I push the door open, I see her - something that was off-limits and taboo not so long ago, ripe for the taking.

"MMph! Mmhm mhmm mhmm mmhph!" mewled Brittany through her tape gag. She had tied her legs spread wide, on full display, to the bedposts. She lay flat on her back, arching slightly while she worked the ribbed dildo through her now-very-glistening, clean-shaven pussy. She had managed to loosely tie her wrists together in front, as well. Well this won't do at all! I shrugged my shoulders at her inadequate self-bondage.

I grabbed her wrists, which must have caught her by surprise as she let go of the dildo jammed in her crotch, and kept them above her head. "If you're going to be bound, you're going to be bound propserly," I saw with a wry grin. Brittany nods attentively, and mmphs what must have been a, "Yes, master," through her light gag.

For the time being, I simply tied her wrists together much tighter than before, and then tied her bound wrists to the bedframe straight above her head. I check the remaining ropes and tighten them around her ankles. "There, that's better, don't you think? Now, let's have a chat and establish some ground rules," I say as I reach to peel off her tape gag.

"Mmmh--oouch!" Brittany exclaims as I rather ungingerly yank off the Microfoam. "Hey, I thought you said this stuff didn't hurt!"

"Everything hurts if you intend it to hurt," I say as I also yank the dildo out of her crotch, eliciting another yelp from her pretty mouth. "See?"

"So, what do you mean by 'ground rules,' Nate? I thought this was pretty simple - you just come here, and you fuck me. When I was a little girl, I always fantasized about how you.. mmmph!" Her sentence was cut off by my hand around her mouth.

"It's not that simple, Brit. Ground rule number 1, no screaming or interrupting, or else the gag goes back on, understand?" Brittany nods. I remove my hand. "Good girl, now contrary to popular belief, I am not here to simply 'fuck you.' I am here to make sure you behave like a good girl, and maybe, just maybe you'll get my cock at the end of the night." Brittany groans with an audible Awww, man, c'mon under her breath. Millennials... always seeking instant gratification... I thought to myself.

"Now, since we have all night, why blow it all at once?"

Brittany laughs at my unintentional pun. "Ok, I agree. So, what other ground rules do you have?"

"Well, for starters, do you have any limits? Anything that you are vehemently opposed to?"

"Lll... ll-limits?" Brittany stutters. "I don't think so... why don't you just surprise me?"

Of course you don't have any limits... you've barely begun exploring this delightful kink... "Now now, I don't think you want any of my surprises just yet. I had some... other fun in mind," I say as I set up my computer directly in front of her eyeline, with several bondage clips queued up for our viewing. "As you can see, I have amassed quite a backlog of bondage clips to watch. I was not planning on watching them until I returned from my trip, but since... this delightful opportunity has presented itself, why not?" I say as I light graze her wet crotch with the back of my hand, slowly working my way up to her breasts, lightly fondling each of her boobs, drawing an audible gasp from Brittany as she closes her eyes slightly.

"I'll put you in three different positions for tonight. You have already been hogtied, and now you're in a spreadeagle, and we will finish off with a fun position and see what you enjoy best," I say as I begin playing the first clip.

"Well, hey wait a minute, I have quite a collection, too!" Brittany exclaimed.

"That's nice, but tonight you are my slave, got it?" I say as I lean in, my face millimeters from hers, examining her playful-but-submissive countenance. Brittany's gaze shifts from my eyes to the video. I grab her chin. "I asked if you got it, slave."

"I got it, sir," Brittany replies, and winks at me and then looks back at the dildo laying between her legs.

"Don't worry, there will be plenty of time for that," I say as I pick it up and bring it to her pretty lips. "Suck on it."

"Oh! But... must I? Please no I... - arrgh!" I ignore her please and jam the wet dildo through her lips which she does not manage to shut nearly fast enough.

"See, this would have been a good time to mention that one of your limits is sucking on a dildo that has just been inside your pussy. Enjoy sucking on your own juices as a lesson about thinking ahead," I say, looking around her room for something suitable to gag her with. "Hold that dildo in your mouth - don't spit it out, or you'll be punished, understand?" Brittany's face, now suddenly slightly fearful, nods.

I go through some of Brittany's drawers and look for something to pack into her mouth. I find a set of full-bottom cotton panties that should fill her mouth completely. I grab the electrical tape and bring the panties to Brittany's mouth. "Open," I say. Brittany complies and the dildo falls onto her chest, resting in between her perky breasts. I wad up the cotton panties and begin to cram them into her mouth, gently prodding them to fill her cheeks. "Keep your mouth open - open wide," I command as I bring the electrical tape to her mouth, and begin winding it around her head five times, cleaving her lips but ensuring the packing was secure. I spank her pussy twice.

"Mmph! Mmph!" Brittany yelps. The gag works at muffling her sounds.

"There, now that you are securely bound and gagged, let's enjoy ourselves, shall we?" I place a pillow beneath her head so she can better watch the videos. I take the dildo and begin gently thrusting it into and out of Brittany's pussy, slowly working it through her labia, letting the ribs of the dildo bring every one of her senses to the forefront. I continue to tease her like this through four 5-minute clips, bringing Brittany to an agonizingly close edge of orgasm, but each time refuse to let her finish.

"MMMMMPH! MMHM MHMMMMM!" Brittany screams through her gag.

"Hey! Not so loud or we'll awake the neighbors. This is called 'edging' - be a good girl and you'll be allowed to release, soon," I say, winking at her but only drawing an angry, frustrated gaze from her face as she continue to scream into her gag. I ignore her pleas and simply continue toying with her pussy through two more videos before, just as she begins to settle and calm down, a video with rough bondage sex comes on. I see Brittany's eyes widen and stare intently at the screen, and on cue and without warning, I begin violently thrusting the dildo into and out of Brittany's pussy. Within moments, Brittany's eyelids flutter shut as her eyes get cross-eyed and her body loses all control: her hips buck wildly and I struggle to control her body as a huge orgasm drives Brittany to ecstasy. Struggling to catch her breath, her climax causes her to squirt a little as I yank the dildo out.

As Brittany begins to breathe normally again, I tilt her head up and point out her juices on the bedsheets. Her eyes widen in astonishment. "I bet nobody has ever made you do that before, huh?" I ask. Brittany is only able to mumble something incoherent into her gag.

"Alright, one orgasm means a water break. I am going to remove your gag, so just hold still..." I say as I begin unwinding the tape, taking care this time to ensure that her hair does not get caught up in it. I help her spit out her panty-wad, and leave momentarily to bring a glass of cold water to her lips. She drinks it willingly, gulping it down quickly. Her body is beading with sweat from her struggles in her bondage.

"Thank you, sir," she replies. Another video comes on of a woman ball-tied, sparking Brittany to ask, "Maybe, maybe you can tie me like her?" she nods over to the screen.

"Maybe," I ponder, "But I have an even better idea that will be sort of like a modified ball tie. Do you still do gymnastics?"

"I do, actually! I'm very flexible! If you let me free, I can show you!" Brittany smiled, wiggling her pretty little pink-painted toes at me. I smile and grab more rope.

"For this ball tie, you are actually going to have to bend your knees and your ankles will go straight behind your head. Your hands will be bound in front of you, but since all the knots will be behind your head and we'll crotchrope you, you won't be able to pick at any of them to get free. It's a pretty stressful position, but for the final position for the night before we finish I think it'll do. Any last questions before we begin?"

Brittany shakes her head. Excellent, I think to myself. I untie her legs and wrists from the bed, and let her perform some quick stretches before beginning her bondage. Once loose, I first apply the crotchrope, similarly to before, tying a coil of rope around her waist before cinching it off as I run it through her parted labia and up her cute butt. I leave a bit of slack so she can bend over and she begins getting into the position with ease. Brittany lifts both her legs up and over her head, locking them in place. I quickly grab more rope and tie her ankles together, and although she cannot get them back above her head without separating her ankles, I tie another length of rope behind her head and attach it to her now-taut crotchrope, so any wiggling will ensure the crotchrope will only dig further into her pussy, completely immobilizing Brittany in a ball.

To finish off her bondage, I take her wrists and bind them and rope them to the crotchrope now sitting just below her naval.

"How does that feel?" I ask as I tip her over to her side playfully. She struggles but cannot do anything more than move around on the bed.

"It's really tight! I can't get loose at all!"

"Good! Then we have one final step to add. Now I think you'll need a really big gag this time, because you've earned a little surprise for being a good girl tonight," I say as I walk behind her and pull off my pants. I take off my boxers, now stained with a mixture of sweat, pre-cum and cum, and then grab the roll of duct tape. I dangle the boxers in front of Brittany's face as they unfurl. Brittany's eyes widen and she tries to roll over to her other side to see my throbbing cock, but I keep her where she is.

"Oh come on, Nate, please let me see! I want your big cock, please? Please please please?"

"Well, since you said please, why don't you taste me first?" I say as I motion her to open up her mouth as I ball up the boxers as best as I can. They won't fit all the way in, but she opens compliantly and I do my best to jam them in, ensuring the crotch part rests on her tongue. With her mouth gaping and stretched open by the fabric, which not only fills her cheeks but also sticks out, I begin to deftly wrap the duct tape around her head six times, from top to bottom, ensuring that her entire lower jaw is now plastered with the shiny silver adhesive.

"There, that ought to hold your screaming for what's coming next... and yes, that pun was intentional," I smile at her. Brittany only manages a weak smile back, her rough gag completely cutting off any noise or mewling she attempts to make. I take the dildo and begin working her from behind so that she is still able to view the videos. Brittany at this point is so wet that it is almost impossible to contain her, and I happily let her cum three times within the span of ten minutes before I throw the dildo aside.

I move her over so she is balled up on her back, her pussy facing me on display and wide open. I tug the crotchrope aside so it sits outside her labia. I look into her eyes and ask, "Are you sure that this is what you want?"

Brittany nods excitedly.

"I can't quite hear you, speak up slave!" I laugh as Brittany moans wildly into her very thick and effective gag, pleading for me to finally enter her. I put on a condom and slowly lean in and begin to finally have the long-awaited, and long-dreamed of sex that she had been yearning for all this time. I take care to thrust gently at first, before speeding up and varying my thrusting and depth to which I go. I can see Brittany shutting her eyes as the first orgasm rocks her body. She yanks on her ropes, clenching her fists and screaming into her gag. I continue thrusting and keep on going, wondering myself how long I wanted to last, and how many orgasms she deserved from me.

Another two orgasms pass before I can see Brittany no longer fighting, no longer having the energy to struggle in her bondage. "Had enough yet, Brit?" I ask, but she is only able to moan softly. I grab her by her perky breasts, and grope and pinch her nipples as I only get deeper. As I can feel her pussy clinching, ready to cum one more time, I let myself release just as Brittany's final climax for the night hits her. She moans into her gag and opens her eyes as she feels me cumming inside her. I smile and once finished, exit her pussy and kiss her on her forehead and gagged lips.

"How was that? Still happy you sent me those picture messages?" I lay beside her and listen to her unintelligible groans. "I think you're ready to be released now, hmm?" Brittany nods her head.

I undo her crotch rope first, and then release her ankles and finally loosen her wrists so she can take off the remaining ropes and her gag. I pull up my shorts and gather all the materials from around the room into two piles, placing hers in a bag and putting all my belongings back into my backpack before helping her unwind the tape from around her head. Exhausted, she spits out the fabric that held her screams of pleasure in check before falling to her bed.

I get ready to exit the apartment and return to my home and give her a soft kiss on her butt, breasts, and finally her lips.

"Thank you, Nate. That was... amazing," she sighs. "Please tell me that you are visiting again, soon."

We shall see, Brittany. We shall see.

The End... ?
Attachments
BB.JPG

Post Reply