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Printed from https://shop.writing.com/main/view_item/item_id/1945979-My-Plus-Sized-Mistress
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by B-E-B Author IconMail Icon
Rated: GC · Short Story · Adult · #1945979
A story about how a boy meets his rather large mistress and the night she claims to him.
         Rubbing my eyes, I push my seat back from the table, a book laying open upon its surface.  Needing to get my blood flowing, I rise up and stretch, several audible cracks sounding as I slowly swing my head from shoulder to shoulder whilst bringing my hands around to my lower back to further stretch.  Strewn about on the table are several tomes similar to the one that I had been reading from.  Dry as sand and littered with more citations than zits on a teenager’s face, I never could keep focused on reading scientific literature, but the notes etched all over several leafs of paper were testimony to my current need of it.  Turning my attention back to the isles, I search for yet another journal that I need to follow a chain of citations.



         My eyes settle upon a rather large woman in the same isle that my search has brought me to.  From my best estimation, she was roughly five foot eight and likely weighed somewhere in the lower 300’s, give or take a few pounds.  She was also dressed in jean shorts and a red shirt, which complemented her dyed green hair nicely, but that’s not what caught my attention.  I found my eyes drawn to the shape of her body; a deliciously large, round, ass, an equally large belly, and atop of it rested two marvelous breasts. 



         On a normal day, I would come up with an excuse to avoid talking to this woman, not out of disgust, but out of my timid nature around women I found attractive.  I made an exception this time, since I had been trying to step out of my comfort zone and talk with more women.  It helped that she appeared flustered, crouching down, flipping through the various books and journals, muttering under her breath slight curses.



         “Having trouble finding something?”  Hoping my voice did not come out as shaky as I felt it sounded, I crouched down next to her to peer at the section she was perusing.



         Only taking a quick glance before turning her face away, the voice that came in the form of her reply was sweet honey to my ears.  “I’m just having a little trouble finding a particular book.  I’ve been looking for hours but I just can’t find it anywhere.”  Curious, I asked what she was looking for exactly.  Pulling out a sheet of printer paper, she showed me the title and author of a book she was looking for: “Lycanthropy: New Evidence of Its Origin” by Moselhy H. F. 



         Looking a bit more closely at the online print out of the university library website, I stand up and say, “I think I know where I can find this for you.”



         She shot up like a flash of light, “Really? Where?”



         Taking a deep breath, I decided to take a huge step out of my usual comfort zone, “Well…. Um… if I show you… will you go out on a…um… d-date with me?”  I felt like I just jumped out of an airplane.  Through out high school and college, I was never able to work up the spine to ask such a simple question; I could already feel my face heating up from what had to be a blush.



         Much to my surprise and relief she smiled and blushed as well, “If you can find it for me… sure.”  My heart nearly skipped a beat.  “By the way, my name is Keira.”



         “M-my name is Tyler.”  Swallowing hard, I felt wide-awake now.  Surely, I reasoned, my research project could withstand a small detour to help Keira.  After checking a map of the library’s layout, I explained to Keira that what she was looking for was a scholarly journal, not a book.  Pointing to a section on the printout, I show her the journal’s name and how the article she was looking for was just a set of pages within it.



         “Oh, I see now… You must think I’m a complete idiot.”  She looked away from me as we waited for one of the elevators to arrive so that we could go to the next floor up.



         “What?  Not at all; it took me a while to get the hang of finding out about scholarly journals myself… are you new to the university?”  As we conversed, I gradually became a bit more comfortable with Keira.



         “Oh, I’m not enrolled, I’m just trying to learn more about… well… this is going to sound silly.”  After a little encouragement and promising I wouldn’t laugh, I got Keira to explain that she was here to learn more about werewolves and lycanthropy.  I just had to ask if this was a Twilight thing for her, to which she laughed, “I liked werewolves before Twilight made its version of them.”  It made me smile a bit at that.  I read several stories about people’s encounters with Twilight fangirls and I did not need my very first date to be about comparing me to a sparkly vampire or a “werewolf” that can’t seem to keep his shirt on.



         I was so lost in the conversation that I almost missed the row of bookshelves we were looking for.  “Ah, here we are… let’s see…”  I check back to the printout, “Here we go… the journal of Psychopathology… issue 32, year 1999.”  Pulling the journal from the shelf and flip through the pages, “Page one… Seventy…. Three.  Here we go.”  I hand the opened journal to Keira so that she can see for herself.  “I believe that means you owe me one date.”  I blush a bit, realizing what I just said.  “I-I mean… if you still want to that is….”



         Keira giggles a little bit and looks away, “Well, I did promise a date if you a date if you helped me.”  I could hardly believe my luck that she’d still want to go out with me even though I almost called her a twilight fan.  Not wanting to look a gift horse in the mouth, I asked if she wanted to go out to dinner or to see a movie or something like that.  “Hmmmm…. Well… we could have a little picnic… the campus does have a beautiful grassy field… if you bring the blanket, I’ll take care of the food, sound fair?”  Never having had a date before, I only knew the general aspects, such as men pay for the food/tickets/etc, so I tried to insist that I could afford buying the food, but she would have none of it, adamant about being the one to bring the food and everything.  I tried to argue, but something about her… I don’t know, just made me want to give in to what she wants.  “Wonderful.  I’ll see you on Friday then.”  I asked how I’d find her again, after thinking a moment; Keira grabbed my wrist and told me to open up my hand.  Doing as she told me, I watch as she whips out a pen and starts writing on my palm.  “There, now you have my number.”



         I just stand there dumbfounded as she goes off with the journal to check it out or print out the pages she wanted, brain running at a thousand miles a second, trying to rationalize if all that really happened; if that very beautiful, very large woman really just flirted about with me and agreed to date me.  My heart was beating as though to keep up with my thoughts, thu-thumping every half-second.  It takes me about a minute before I realize that I still had a desk full of papers just a few floors below that were waiting for me to come back… with my bag and wallet still on the table!



         Panicking for a whole other reason, I dash to the stairs, able to zip down them far faster than an elevator could move.  ‘Let it still be there, let it still be there.’  I repeated in my head, my silent prayer that there wasn’t anyone with sticky fingers in the library today.  Making a final dash to my desk, I breathe a sigh of relief, as everything seems to be where I left it.  Picking up my wallet, something seems to be a bit off about the feel of it.  Upon inspection, I found that all of my money and my credit cards are missing.  Unable to contain my frustration, I was soon kicked out of the library for the expletive that echoed throughout the library.



* * *



         After meeting Keira on Monday, I seemed to have had nothing but bad luck strike me.  By the time I managed to get my credit cards cancelled, the thief had already used the max credit limit, and then some.  Since it was all used online, it took even longer to convince the bank that the transactions were made by a thief and by the time THAT was taken care of, my credit rating took a huge hit.  However, even with all of this misfortune befalling me, a glance at the phone number on my palm made me smile, remembering the date to come this Friday.



         As the day of the picnic arrived, I felt butterflies in my stomach.  From the moment I woke up, showering, grooming, and preparing for the lunch on the green, I was grateful that I didn’t have my usual early morning classes.  Rather than waking up at seven, as I’d normally have to, I got to sleep in until ten, but I didn’t intend to as it robbed me of the time I wanted to use to spruce up.  By the time I finished showering and shaving, I only had ten minutes left to get myself dressed and run out to the greens.  Cursing under my breath the whole time as I threw on my jeans and a good polo shirt, I grabbed my bike and shot down the stairs, leaping onto the seat before the wheels even touch the ground, pumping as hard and fast as I can.  Pulling out my cell phone, I try to tell Keira that I’m going to be a few minutes late, but just my luck, the battery is dead since I forgot to charge it last night.  “OH COME ON!!”



         Tapping my foot impatiently at the crosswalk light separating the dorms from the main campus, I glare at the traffic lights, trying to will them to change so I may cross.  “Come on… come on… Finally!”  Using my full weight to press down on the pedals to pick up speed, glancing at my watch to see I’m nearly ten minutes late.  “Please be there, please…” My heart skips a beat when I see her.  Given her size, Keira isn’t hard to spot out in a crowd, especially since the greens are relatively empty on a Friday.  Something wasn’t right though; she was packing up the picnic!  When I finally reach her on the greens, I nearly fall off my bike trying to stop.  “Keira, I am sooooooo sorry I’m late.  I slept past my alarm clock and I wanted to look nice, but my cell phone died and… I’m here.”



         She was smiling, but it just didn’t seem to reach her eyes, almost as if she didn’t believe me, “I’m glad you made it, I was starting to think that you were too good to be true.”  Feeling a bit unnerved by the look of sadness in her eyes, I offered to help set the picnic back up.  I insisted on it when Keira started to do it for me.



         As we started to eat, I looked up at Keira and asked, “What did you mean by I was ‘too good to be true’?”  Looking away, some sadness returning to her eyes, she said that she’s had a lot of disappointments in the past and wanted to leave it at that.  Considering myself lucky to have gotten this far with her, I decided not to risk a future date by pressing the issue.  After finishing my share of the picnic, I laid back on the quilt, feeling the tickle of grass pressing up against me through it.  The sky was so clear and blue; I wondered why I didn’t come out for something like this more often.  In the middle of that thought, I felt something press up against my hand.  A quick glance revealed that it was Keira’s hand, smiling, I took it and laid there with her, staring up into the sky as clouds and birds crossed overhead, conversing about various topics, ideas, events old and current.



         The topic somehow drifted over to sexuality and people’s sexual preferences, “I’m just saying, everyone has their kink, but come on, you have to keep in mind that there are other people in the world too, and I don’t care how hot you find them, jerking off in Wal-Mart in the Hot Wheels section is just plain wrong.”



         The both of us laughing at the story and groaning a bit at just how awful it was, Keira bit her lip as if trying to figure out how to ask her question, “Speaking of kinks…” I could see where she was going with this and the idea of sharing such information started to make me blush.  Hoping to turn it around, I suggest the idea that I’ll tell her mine if she tells me hers.  That really turned the tables to get Keira blushing, which looks incredibly cute, I realize, given how rosy her cheeks were to start with.  Much to my chagrin, she turned away and started to mumble her response, just barely loud enough for me to hear.  “Well… I like shy guys… and, um… well… when you were blushing on Monday; it just really got me aroused… I wanted to just take you off to a broom closet somewhere in the library and take you.”  Just hearing a girl say such things, much less this beautiful woman, made my face go beat red.  I comment that she sounds like a very dominant woman in the bedroom and I kinda like it.  I could have sworn I heard a gasp come from her lips after hearing me say that.  “Alright, I told you mine, s-so what are yours?” Feeling embarrassed, I divulged my desire to be owned by a mistress; to be her puppy to play with and reward with whatever she felt was suitable.  When she didn’t shoot me down right away, I continued on about my fascination with the idea of being made to dress up and look like a girl, and not just a super-girly sissy, but like an actual girl.  Much of what I was into seemed to make Keira more fidgety, like the idea was turning her on.



         I was just about to say something, but then Keira was right on me, pressing her lips to mine.  I would have gasped had it not been for the seal her lips formed around mine.  I could hardly believe it, my first kiss and it was initiated by the girl, after learning that it was supposed to be the guy that made the big advance, it made me blush to think that she set the tone of her being the “male” in the relationship, which made me whimper a little.  Especially when her hand found its way onto my inner thigh.  Having never been touched like this, I could feel my face lighting up like a Christmas tree.



         When she finally pulled away, I was left stuttering, unable to think of anything to say.  It seemed to only make her giggle though, as if my inability to talk was funny.  “You’re so cute, you know that?” With nothing to respond with, I could only look away, a natural reaction when I get this embarrassed.  That’s when Keira took hold of my chin and turned me back around to face her.  “Don’t look away from me, I want to see your face… aww, you’re blushing, aren’t you?”



         Just from the sound of her voice and the way she handled herself with me, I knew Keira was just the sort of woman I was looking for.  I looked around on fetlife and met a few people that taught me a few things and helped me realized what I really wanted, but it took the chance encounter in the library for me to meet the woman I truly felt I wanted to be submissive to.  It was only a second meeting, but I knew deep in my heart that it was right, and just imagining the possibilities was making my pants particularly tight.



* * *          One Month Later          * * *



         Keira and I went on many dates since that first picnic on the greens.  Many people gave odd looks to see a couple like us, but we ignored them each time, knowing they didn’t matter so long as we had each other.  We spent much time kissing and caressing each other, but it never went beyond that.  After such times, I’d have to relieve myself afterwards.  Tonight though, I got a message on my cell that she wanted to spend the night at her place and that she had something special planned.  The wink emote and the heart symbol she included in the text got my imagination going in particular directions.  Surely after a month, we’d move on to the next stage, right?



         Nonetheless, arriving at the address I had grown familiar with, after driving Keira home after many a date, I forced myself to lower my expectations to something more realistic.  She probably just fixed a special dinner or something, she did seem to like to spoil me on our dates, I almost had to fight her to pay my fair share for anything, even the gas for my car.  Taking one last second to fix my hair, hoping the beads of sweat from my car’s broken air conditioning wont be too distracting, before knocking on the door.  After a few seconds, my cell phone buzzes with a text message, curious who it could be, I see it’s from Keira, reading: “Key is under the welcome mat.  Meet me upstairs.”  This was very unusual, but I wasn’t going to question it.  Finding the key, I open the front door to a dark house.  Anxiety rising, I close and lock the door behind me, pocketing the key before going up the stairs, using the handrail as a guide.  The path was as dark as the night outside, but I left the lights off, always seeking to conserve energy when I can I had grown used to seeing in the dark.  Reaching the top, the second floor was just as dark as downstairs, with the sole exception of the third door down on the right, from which light spilled out from a cracked open door.



         Grinning, I began to grow hard, imagining what I’d see behind the door.  Maybe Keira was laying there in lingerie waiting for me, maybe she wasn’t wearing anything at all.  She said to meet her up here, so I peeked into the room to see if I should announce myself first… but the room was empty.  Thoroughly confused, I entered, looking about for any sign of my girlfriend, but all I could see that was out of place was a thick brown package on the bed with a folded piece of paper on top with my name written on it in bold, handwritten letters.  Picking up the letter, I opened it and read the simple message: “This gift is for you, put it on and come down to the kitchen, boy.”  I blushed a little bit, Keira saved calling me ‘boy’ only when she is being particularly controlling of me, and she knew how much I liked it.  Pulling the Swiss army knife I always kept with me, I cut the tape sealing the package and blushed even harder when I realized its contents: a frilly black-and-white maid’s outfit with black stockings, black high heels, white elbow gloves, a studded black collar with a blue trim and a D-ring, and to top it all off, a pair of pure white panties.  ‘She wants me to wear THIS?’  I think to myself, ‘How does she even have my size?  Wait, that’s not what’s important…’ I end up blushing at my own thoughts, heart skipping a few beats as it picks up its pace, pumping blood even faster.



         Some time later, after struggling to get some of the pieces of the outfit on, I hobble back down the stairs in the heels.  My heart is beating so hard that I can’t even hear my own thoughts, all I can think of is the command that was left written for me: to go to the kitchen.  I’ve never worn heels before, so I was heavily relying on the stairwell railing to keep myself from falling down the stairs.  Hobbling over to the kitchen, I start to get my bearings with the heels after flicking on the lights, I find yet another folded note with my name on it secured with a magnet to the refrigerator.  “Oh lord, what now?” I whine as I take the note out from under the magnet and open it, wondering where the heck Keira is.  “I am in the living room, fix me dinner, boy, and bring it in on a platter.”  It was at this point that I realized it; this was one of my fantasies.  She didn’t even have to lift a finger and Keira made me her sissy maid slave.  Realizing this made my panties become much, much tighter than they already were.  Opening the fridge, I begin to look to see what is available to make for her.



         Coming into the living room, carrying a heavy platter of food, I continue to hobble about on the heels, careful not to trip or spill the food.  Hearing the sound of hands clapping, the lights all come on, revealing my Keira lounging on the couch, garbed only in her onyx-black and emerald-green corset and a black skirt.  “It’s about time you got here boy,” she almost purred from her position on the couch, “I do hope you don’t waste so much time next time.  Now get your sissy ass over here and feed me… then we’ll deal with your punishment for making me wait.”  Carrying the platter over, I take the dome off with a flourish to reveal the meal of fruits and meat I prepared for her.  Turkey, grilled chicken, peaches, pears, grapes, and other assorted foods, taking a fork, I begin to feed her little by little.  “Alright boy, that’s enough for feeding me, time for you to eat.”  I gulp, plucking a grape to put into my mouth, but Keira stops me, “Ah-ah-ah, that’s not what I meant, boy…” Following her eyes, I find where she was talking about… she wanted me to eat her out… I don’t know how I didn’t notice her missing panties sooner as her free hand slowly pulls up her skirt, revealing her glistening, shaved mound.  It was only then that the smell of her arousal reached my nose, making me bite my lip.  Without saying a word, I reposition myself betwixt her legs, breathing in her aroma, my exhaled breaths bathing her nethers with heat.  Hearing just the slightest whimper, I wait for her to resume eating before allowing my tongue to taste my delightfully dominant girlfriend’s flavor, wondering if these lips might bear the same taste as the other pair I have sampled.



         If anything, these lips were much sweeter, intoxicating even.  Taking my time, enjoying the taste, I drag the full breadth of my tongue over her folds from the bottom, all the way up to her sensitive button, which I flick with the tip of my tongue.  Opening my mouth wide, I wrap my lips around the entirety of Keira’s pussy as I let out a loud, long moan, my voice working as a vibrator on her flesh.  Eyes cast upward at her, I moan even louder at the sight of my wonderfully fat love stuff her face with the food I fixed for her.  So turned on, I reach down with my hand and start to touch myself through the panties, the contrasting feel of the cool silk against my hard, hot cock makes me moan even louder.  She catches sight of this and puts and end to it right away, “Oh no you don’t, boy.  That cock is my property, you don’t get to touch it without my permission, understand?”  I could almost feel my face getting redder as she claims further ownership of me.  Deciding to push my limit, I continue to touch.  “Boy, I said no.”  I keep on touching in defiance to see what she’ll do.  I find myself regretting my actions as she grabs me by my hair and pulls me right up.  “I said no boy!  You just earned yourself a night of punishment.  Here I was trying to give you a treat, but you decided to defy me.”



         Getting up from the couch, Keira drags me by my hair to the stairs.  I hobble on my heels, trying to keep up without breaking anything.  Knowing I messed up, I whimper apologies as she drags me along, begging for forgiveness, that I won’t do it anymore.  “Too late boy, I gave you your warning and you chose to ignore me.”  Pulling me into her bedroom, Keira tosses me onto the bed and whilst still imposing her will on me, she commands me to take my panties off.  Shaken by her aggressive treatment, I felt incapable of anything but obedience, slowly taking them off, exposing my manhood.  I ask what she’s going to do, but she slaps me, shutting me up.  While rubbing where she hit me, she forces my cock into something cold and hard.  Looking down when she pulls away, I see she’s locked my cock into a cock cage.  “Until you learn your place, slave, you will only get to cum when I give you permission, understand?”  I slowly nod, feeling so… dominated… and it feels good.



         “Now then… I’m going to have to punish you… I was going to save this, but you leave me no choice.”  Moving my attention from the stainless steel case around my cock back to Keira, I feel the blood drain from my face upon seeing the huge strap on she is wearing.



         I stutter and whimper something along the lines of, “Wh-wh-what is that th-thing for?”  She answers that it’s what she’s going to use to fuck me with, to which I reply, once again stuttering, that there’s no way it could possibly fit.  As if expecting that, she threw a bottle of lube onto the bed next to me.



         “Use that to prepare yourself while you use that tongue of yours to lube ‘me’ up.”  The evil smile on her face makes me bite my lip so hard, I fear I might draw blood.  Getting onto my knees, I start to lick at the strap on while my hands got to work behind me, applying lubricant to my tight hole.  Feeling the size of the fake cock in my mouth didn’t help me relax at all, mental images of it entering me invading my mind as I apply lubricant to my ass.  Meanwhile, hearing Keira’s whimpers and moans at the sight of me sucking “her” off keeps my cock hard and ready for her.



         “Mmmmm that’s enough, boy I think you’ve soaked it enough for that sweet little ass of yours.”  Taking a step back, Keira pulls her strap on from my mouth.  I whimper for her to be merciful to me, but she just bites her lip and smiles.  “On your hands and knees, boy.”  Gulping, the cage feels particularly hard around my swelling cock as I present my lubricated ass for my girlfriend… no, my Mistress, and I made sure to address her as such when acknowledging her command.  The sound of me submitting and calling her by the title “Mistress” sent shivers down her spine.  If I had seen her shiver like that, my cage would be even tighter.



         The moment the saliva soaked dildo pressed against my ass, I gasped.  The lubricant she had me put on was cold, so the temperature contrast between it and my saliva on the strap on made it feel as though a real cock were pressing against me.  I tensed up a moment, and thankfully she knew to wait a few moments to let me loosen up, rather than force her way in and risk tearing me.  Even with all of the preparation and lubrication, it felt so big.  ‘Does it really feel this big for women when they get fucked?’ I wonder to myself as my Mistress slowly eases her phallus deeper into me.  It felt so strange, I had tested myself before with a finger or two, but it felt nothing like this, to have something so big, so solid, so lubricated and so deep inside of me, I could feel it rubbing against every part of me inside.  Being dressed in such a soft, silky maid uniform only added to the sensation, humiliating and exciting me at the same time.  “P-p-please, fuck me harder Mistress,” I find myself whimpering.  If I could see behind me, I would have seen Keira bite her lip and whine before obliging, thrusting a little faster, the lubrication helping her strap on to glide in and out of me faster as my ass became more relaxed around it.



         Leaning over me, pressing her body against my back, I feel her hands reach around to pinch at my nipples through the top of my maid’s uniform.  Slipping her fingers under the silken fabric, I moan like the little bitch I’ve been made into as she once again pinches and starts to twist my nipples, harder and harder with each twist as she nibbles at my ear.



         One of her hands leaves my nipple, but just when I think I’m about to get some relief, but the hand went straight to my cock’s steel prison.  I moan and whimper, wanting so hard to get hard and cum, but the confines of the cage keeps my cock from swelling at all, even as I feel my orgasm getting closer and closer.  “Don’t cum before I give you permission, boy… or you’ll be stuck in that cage for the next two months as punishment.”



         TWO MONTHS!  “Please Mistress! I, I can’t possibly hold on.  Please, let me cum now Mistress.”  It was getting so hard to focus, her touch, the feel of her skin, the cold, unyielding metal of the device around my cock.  Before I could even get a reply, my body betrays me, achieving climax, cum seeping through the tiny hole at the end of the cock cage, with her hand right on it, Keira noticed the instant it happened.



         “Such a bad boy… once again you disobey me,” she whispers into my ear, “you know what this means, don’t you, boy?”  Whimpering in shame and humiliation, I nod.  “Good, I have the key to that cage of yours… and you’ll wear it for the next two months… and I’ll tack on extra days if you orgasm like you did just now when I play with you.  Do you understand, boy?”  I gulp and nod as she moves me aside to lay on her back, commanding me to resume licking her… that I owed her an orgasm since I took the orgasm I didn’t deserve.



         That night took our relationship to a new level… that was the night Keira claimed ownership of me as my dominant.  Whenever we were out of her house, she made me wear a necklace as an “everyday collar,” but the moment we returned to her home, I was to immediately dress in my maid uniform with the more prominent dog collar.  I’d get spankings and even a few fuckings from her strap on, but I had never been happier.

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