Pegged by the MILF Read online

  Contents

  CHAPTER ONE Peeking is Naughty...

  CHAPTER TWO Alone in her House

  CHAPTER THREE Punished by her Massive Strap-on

  CHAPTER ONE

  Peeking is Naughty...

  Pegged by the MILF

  Copyright 2015 Brooke Dubois

  Please note that this is an explicit work of femdom erotica which contains graphic descriptions of a young man losing his virginity... just not the way he expected! He tries desperately to resist his deepest, darkest desires, but the older, dominating woman of his dreams forces him to confront his true nature and slutty, submissive side as he takes every last inch of her brutal, massive strap-on. All characters are consenting adults. Enjoy ;)

  The professor drones on in his monotone, dry voice, and even those with the time on their smart-phones and laptops are not too subtly glancing up at the clock, trying to get him to take the hint. The girl in front of me sighs and starts to put on her jacket, and it is only then that the white haired Mr. Worth pauses mid sentence.

  "Well, looks like that's all for today class. Don't forget, your essays are due at the end of the week."

  An essay that I have barely started on. Just two more years of this and I can apply for law school - as long as I keep my gpa up. When people hear that I am majoring in philosophy, they always ask why. I always answer that I find it the absolute easiest way to make the straight A's I am going to need to get into any halfway decent law school. Not that I do not enjoy Socrates and Kant, I do, truly - it's just that people want to hear that you have a plan rather than a passion.

  The class is funneling out quickly, and I am about to join the flow of people out of the stuffy classroom and into freedom when my phone buzzes in my pocket.

  "Hello?"

  "Hi Nathan," comes a low, sensual voice, a voice I will never forget. It is a voice that has kept me up at night, invading my mind with images of her perfection.

  "Miss Avila?"

  "Oh, I wasn't expecting you to recognize my voice. Please Nathan, call me Janeen."

  I have had a crush on Miss Avila for as long as I can remember. She moved to the neighborhood four years ago, when I was fifteen years old and still in high school. She was so much different than other women. So much more distinguished and confident than my classmates, so much younger in spirit and more vital than most women her age. A divorcee and career woman, I was always fascinated with her. I always had trouble waking up in the morning until she started to jog, passing my house at 6:33 sharp in the morning and I would look out my bedroom window at her in her short shorts, watching her hips move with her graceful gait, her long black hair tied up in a ponytail. I cannot remember the last time I saw her more than just in passing but I would eavesdrop on her when she came for coffee with my mother, if only to hear the perfect, almost musical tones of her voice. One of the things I miss the most about living on campus is the random sightings of her as I looked out my window. God, I'd love to lose my virginity to a woman like her.

  "What can I do for you, Janeen?"

  "Well Nathan, you've heard about the recent burglaries in the neighborhood, haven't you?"

  "Yes, I think Miss Olsen got robbed just two weeks ago. Really terrible, I heard she lost some really valuable jewelry."

  "Horrible, isn't it? Imagining some strangers in your house, your sanctuary. The thing is, I have to leave for a business trip tonight for a few days, and I don't feel comfortable leaving an empty house. Your mother gave me your number and said you might be able to help out? I would feel so much safer about my home if you were there."

  "I'd love to help out, Janeen."

  "That's perfect. Are you able to come over sometime for me to give you the tour? I am leaving at 7:00, so if you can't I could just leave a key outside..."

  "I just finished class for today, how about I head over now? I should be there by 5:30, the busses run nearby."

  "That's perfect. You're a lifesaver. I'll see you soon."

  "Goodbye."

  I put my phone back in my pocket and smile. Every time I passed her in the street, or saw her at the grocery store, she always had a smile for me that lit up my day. Sometimes, I find thoughts of her randomly popping into my head. She just seems so much classier than the girls in my college classes, so much more worldly and intelligent, so well-read and learned. I sometimes feel like every opinion my classmates have is just being parroted from an article they skimmed or something someone else told them, but when Miss Avila speaks - even though she wants me to call her Janeen, she will always be Miss Avila to me - I can tell she is speaking her own mind and opinions. For some reason I feel nervous as I bus to her house, and when I ding the stop I realize my heart is beating quickly.

  Her house is only a few minutes walk from the one I grew up in, but the houses get noticeably nicer. While I do not know exactly what she does, I know she is pretty high up working for a marketing firm of some sort. She must be high up to afford a place like she has. It is one story and modern, hidden behind a yard with tall evergreens. I open the gate and walk up the driveway, where a beautiful black Porsche rests, with windows so tinted they must be illegal. Even if a cop stopped her, she could talk her way out of any ticket. I reach the door and knock, feeling my heart pounding with anticipation, my palms embarrassingly sweaty. I take a deep breath to calm myself, and the door opens.

  "Welcome Nathan! My, you've filled out since I last saw you. Thank you so much for coming on such short notice." Her voice is warm and inviting, with the hint of sensuality that always lies beneath it. The complement that I have filled out brings color to my cheeks, and I hope that she does not notice. It is not hard to see how she was able to rise so high in a marketing firm. The way she speaks, she could have asked me to do anything and I would have agreed without thought. She is just as tall as me, standing at 5'10 and our eyes meet, hers blue and intense, with a hint of eyeshadow defining them. She must be close to forty but looks better than most of the twenty somethings in my classes, her age giving her a distinguished, mature beauty and laugh lines that speak of a mirth honed over years of good living. She radiates effortless beauty, her long, wavy hair falling gracefully to her bosom. She is wearing a white button up shirt and a tight, dark blue skirt, her feet bare except for tiny, thin socks that must be made to be invisible in high heels. I feel under-dressed in my jeans and t-shirt.

  "Not a problem." I am trying my best not to stare at her. She is feminine beauty and elegant professionalism embodied. I want her more than I ever have before, and I try to push thoughts of her out of my head, try not to imagine unbuttoning her white shirt one at a time until her perfect breasts fall out and her nipples are naked, eager for my touch. I swallow, trying to get control of myself and walk in, awkwardly undoing my shoes while she waits, unable to stop myself from letting my eyes quickly wander to her thighs. I am standing in the house of the woman of my dreams, the woman who I have wanted for years, unable to keep my mind from straying to her at the most inopportune times. I feel heat coming to my cheeks as I look at her smiling face. If she knew the thoughts I had had about her, the things I thought while pleasuring myself, she would kick me out, yell at me, never be able to look at me again and I feel guilt and shame.

  "I'm sorry I don't have more time to chat! I need to head to the airport as soon as possible. All I need is someone to stay here overnight, maybe leave a different light on every night so burglars know the house is occupied. There's a few plants around the place, but if you forget to water them they will survive until I am back. Here's a key - I have to jet! Feel free to eat or drink anything in the fridge, I think there are some beer lying around if you like. The couch pulls out in the living room, you can sleep there if you like. Thank you so much for doing this for me.
"

  She hands me a key to her house and puts on high heels, grabbing her small wheeled luggage and heading out the door.

  "You're welcome," I say, unable to stop myself from staring at the swaying of her hips, her tight dress hugging the curves of her perfect behind.

  CHAPTER TWO

  Alone in her House

  As soon as the door shuts behind her, I look around at the house. It feels surreal to be in the home of the woman of my dreams, a woman that has invaded my thoughts from a young age. A shiver runs through my body as I look around Miss Avila's residence, and I explore the house, walking through the modern kitchen, all black marble and ultra modern style. I find myself in her bedroom next, and I look at her king sized bed, much larger than I would have expected for such a slim woman. The lucky, lucky men who were allowed to share this bed with her! If only I could count myself in their numbers, I would die happy. Maybe if I was a rich lawyer or a businessman, she would look at me as a man. My eyes fix on the dresser drawers, and I bite my lip, trying to fight the urge to look in them. What panties does she wear? What beautiful, sexy undergarments have been touching her pussy and ass? Fuck, this is so wrong. I need to get out of here!

  I leave the bedroom, my heart pounding from the strength it took to resist looking, walking quickly into the kitchen and checking out what is in the fridge. For one woman, it is way huger than the mini fridge I have in my tiny dorm room. It feels incredible to have so much living space around me! Someday, I hope that I can have all of this for myself. There's a twelve pack of Stella Artois beer in the fridge, and when I see the awesome Stella pint chalice, I cannot resist looking around for a bottle opener, prying off the cap with a satisfying hiss and pouring myself a tall glass. The entire house is like something out of a magazine or movie, and I sit down on a barstool with my imported beer, taking the first foamy sip and sighing with pleasure. What a perfect, beautiful house. Of course a woman like Miss Avila would have a sophisticated, modern place to live and think of ideas for the ad agency that she works at. I can see why she wants to keep it safe from burglars.

  I cannot help but imagine her again. The tight, dark blue skirt wrapped around her curves and full, round ass so enticingly that all I can think about is pulling it up, seeing the cheeks of her ass and the thong disappearing between them. Would she wear a thong? All I would have to do is take a look in her drawers and I would know... I take another sip of my beer, trying to push the thought out of my head. God, her perfect, perky tits - I want to rip that button up top right off her body and take her hard. Before I can stop myself, I've put the chalice of beer down hard and am walking to her bedroom, opening the door, and with my heart pounding like it is about to fly out of my chest, I open up the top drawer of her dresser.

  What I see makes me gasp and my eyes widen. I was expecting lacy underwear, maybe a skimpy thong at the most. Instead, there is a long, purple strap-on dildo, at least ten inches in length and thick enough that I could not imagine it ever fitting into someone's behind. Handcuffs, a short multi lashed whip and a strange looking metal device still in a plastic case, obviously brand new rest in the drawer as well. There is also skimpy underwear, and some sort of leather outfit that looks straight out of a kinky porno. Guilt and shame for snooping fills me, but I cannot resist pulling out first the strap-on, staring at it with wide eyes. It is so thick and long, with a cruel looking wide head that would stretch whoever was unlucky enough to be forced to take it. Was Miss Avila a lesbian? Does she fuck other women with this? I put it down on the dresser and look at the strange device still in a plastic case, and gasp as I see that it is labelled as a "chastity device". It is shaped like a flaccid cock, completely metal and must be used to be put around some man's cock. I cannot imagine ever letting anyone use one on me. It must be painful if you ever get hard. It comes with a key, which must be used to unlock. What is the point of it? To make it so someone has no control over their orgasms? I masturbate at least once a day or else I start to get distractingly horny - what would it be like to be unable to? What would it be like to have my orgasms in Miss Avila's control?

  I put the strap-on back in the drawer and quickly shut it, looking around the room guiltily, imagining if she had missed her flight and came back to find me looking through her most private of places. Shit shit shit! What the hell did I just do! I leave the room, breathing quickly and sit at the bar again, downing half of my beer in a single, nervous gulp. I cannot believe what I just found. Miss Avila likes to use that... rubber thing on men? What does she get out of it? Why would any man let themselves be fucked by a woman like that? Wouldn't it hurt? I finish my beer and pour myself another, trying to wrap my head around it.

  What would it feel like, to be handcuffed by her, lying in her bed and looking up at her perfect body, her full tits and perky nipples, her beautiful smiling face as she stood there wearing her huge, thick strap-on, knowing you are powerless to resist? What would it be like to submit to her, to let her do whatever she wanted? Would she be turned on by me if she had me like that, helpless and afraid? I feel blood surging into my cock and embarrassment and shame fills me, a horrible guilt that it turns me on that she dominates men. I've never thought about letting a woman do anything like that to me, but Miss Avila is like no woman I have ever met before. I cannot help it. I return to her room, open the drawer again and take out the strap-on, looking at the massive rubber cock. It is so much bigger than mine! Oh God, my cock is throbbing, hard as rock and begging to be touched as I look through the drawer again, at the handcuffs and whip, imagining being on all fours, my wrists handcuffed behind me and Miss Avila using the whip on me, making me beg her to stop. I bite my lip, unable to resist my lust and unzip my jeans, pulling out my cock and stroking fast, it feels so fucking good as I stare at the huge strap-on, imagining her slowly pushing it against my virgin asshole, sliding it in as I moan in pain and whipping me hard as I am completely and utterly helpless. I can't stop myself from stroking harder and faster and I can feel my orgasm building up and I try to stop myself but I cannot and I cum harder than I ever have in my life, shooting streams of hot white cum all over her open drawer and wall. Oh fuck! Panic fills me as my orgasm subsides and I realize I just came all over the strap-on, the chastity device, the whip, and worst of all, her skimpy, lacy underwear. I pull them out and see that the worst of it landed on three thongs, and I grab them and the sex toys and rush to the kitchen where I put them all in the sink with hot water and soap, hoping beyond hope that they do not leave a stain.

  What the fuck did I just do! I feel horrific and guilty. The woman of my dreams hired me to protect her house from burglars rummaging through her most precious things and I did so much worse. Even more troubling is the fact that I just... I just... fuck, I can't even think about it. I feel so horrified by the perverted thoughts I just came to. What kind of a man am I, to cum thinking about being fucked by a woman like that? On autopilot, I scrub the thongs, washing them over and over again before putting them on a chair to dry. Next I wash the handcuffs and whip, and finally the strap-on, and as I scrub it with my soapy hand I shiver as I imagine Miss Avila enjoying the site of me sliding my sud covered hand up and down the massive strap-on. My spent cock twitches again from the thought, and I do everything I can to push it out of my head. I put the toys back in her drawer and leave the room, shaking my head in frustration at how weak I was. If only I could have resisted looking in her drawer, wanting to imagine her wearing her panties... if only I could have been stronger! What kind of a filthy pervert am I, to fantasize first about undressing her and fucking her, then to look in her drawers and imagine something so much filthier... I hate myself! I hate myself so much!

  CHAPTER THREE

  Punished by her Massive Strap-on

  The next few days I am able to resist, never going near the drawer again no matter how badly I want to. On Friday she returns while I am at class, and I barely slept the night before, worry filling my mind. What if she somehow finds out? What if she knows what I did? While
I am at class I receive a text, and check my phone surreptitiously while the professor touches on the finer points of Aristotle's Ethics and the importance of leading a moral life. The irony is not lost on me.

  Hey Nathan. Thanks so much for watching my house while I was gone. Come by sometime later today so I can pay you and you can return the key? You have no idea how much peace of mind I got knowing you were there for me!

  Guilt, horrible, gnawing guilt fills me as I text back under the my desk.

  Sure, I will come by. Not a problem Miss Avila.

  For the first time in my life, I wish a class would last forever. It goes faster than any class ever has before. The bus is not late, I do not miss it, and way too quick I am at Miss Avila's house, trudging up the driveway like a dog with it's tail between it's legs. I feel like a disgusting, horrible pervert, and the fact that she is so grateful that I housesitted for her makes it so much worse. She should be yelling at me, or ever calling the cops on me, not thanking me for a job well done! Even scarier is the thought of looking at her now that I know what she does to men. Before I had been imagining bending her over and fucking her hard, but I am worried that now all I will be able to think about is her using that filthy, disgusting toy on me.

  I ring the door bell hesitantly, steeling myself.