Note 1: This is a Christmas contest story…so please vote!!!
Note 2: A special thank you goes to the great people who read my story in advance and give me suggestions and point out errors (Julia…you will always be my pet and Greg…who has sparked a few new ideas for me).
Note 3: As always, a special thank you goes to Estragon for his copy editing. You are a blessing!!!
1. PROLOGUE: HOME FOR CHRISTMAS
My sister was a pain in the ass. She always had been and probably always would have been if she hadn’t become my personal slut. For my whole life, I have had to deal with the fact that my sister was incredibly hot. Now it wasn’t that I didn’t know she was pretty, but I didn’t see her that way for two reasons:
1. She was my sister and incest was morally wrong.
2. She was easily one of the most shallow and bitchiest girls I had ever known.
While she got the looks, I got the brains. I graduated high school at sixteen and at twenty was in my last year of my college degree. Unfortunately, being smart doesn’t get you the chicks and I was a twenty-year-old virgin. I wasn’t hideous looking; I was just the epitome of average. Yet, even though I could debate eloquently and with a vengeance, when I was face to face with a girl in a non-academic setting, my brain became mush and I became verbally impotent.
That brings me to Christmas 2011. I came home from Harvard as I usually did during my Christmas break. Also, as usual, my younger sister, who just turned eighteen a couple weeks ago, razzed me, the moment she saw me, “So has my big brother finally got his cane polished?”
My sister had been obsessed with my non-existent sex life for the past couple of years. She kept taunting me with uncomfortable questions like:
“Do college girls spit or swallow, Matthew?”
“Have you fucked some nerdy virgin yet, Matthew?”
“Hey stud. Any luck munching cunt, Matthew?”
Each question was dripping with sarcasm, as she already knew the answer.
Like every other time, I ignored her blunt question, my face red with embarrassment, and walked away.
I heard her call out, “Does big brother need some lessons?”
I kept walking, frustrated that I let my slutty bitch of a sister get to me. In my room, on my laptop, watching porn (a daily or twice daily routine), I closed my eyes and my mind wandered to teaching my sister a lesson; turning off her aggressive bitchiness and making her my little fuck slut. I came all over myself fantasizing about my sister sucking my cock. Once spent, I pondered, was there some way to make this kinky fantasy a reality.
2. BREASTFED BY SISTER
Next day, I had already been up for a few hours when Sandra finally staggered into the kitchen in a thin robe that barely contained her big breasts. She saw me staring at her and asked, shocking me, “Is big brother getting hard checking out his little sister?”
Rattled by the seductive tone and the undeniable evidence growing in my pants, I stammered, “S-S-Sandra, stop it.”
Her smile dripped with a perversion I often saw in porn, “Stop what, big brother?”
She walked towards me and I held my breath, nervous, like I get when any girl talks to me. My palms get sweaty and my mind muddled. I attempted to pretend I was not distracted by her body and the white flesh I saw peaking out of her thin robe. “Stop talking drivel.”
She laughed, her voice syrupy sweet, “I’ll take that as a yes, big brother.”
Her hands now on my legs, I stammered, “S-S-Sandra, don’t p-p-put words in my m-m-mouth.”
She leaned forward, her hot breath on my ear, her hand cupping her breast, “Oh, I have a good idea what you would like in your mouth, big brother.”
I let out an involuntary moan, brought on by her hot breath and naughty innuendo, and was paralyzed.
She stunned me again when she squeezed my fully erect cock and with her tongue now in my ear whispered, “Oh my, your cock is rock hard. Are you hard for your sister, big brother?”
My brain no longer functioning at its usual capacity, I responded incoherently with a bunch of grunts and half words.
She bit my ear, her hand rubbing my cock through my jeans, “Has your little sister made you so fucking horny that my Harvard brother can’t even articulate a complete sentence?”
Still paralyzed with pleasure and stunned by her inappropriateness, I was unable to answer.
Her breast hit my face and she asked, “Have you ever touched a breast, big brother?”
I shook my head yes, having once touched my chemistry partner’s breast by accident.
As if reading my mind, she added, “On purpose and with consent?”
I shook my head no, my humiliation burning.
“Do you want to touch your little sister’s big breasts?” she purred.
My conscience attempted to scream no, but was silenced by the little devil in my head.
She gave my cock a solid squeeze and whispered in my ear, “All you have to do big brother is ask and you can see and touch your baby sister’s tits.”
All the years of loneliness and fantasy had built up inside and instead of doing the right thing, I did the thing that felt right down below the belt and let out in a whisper of a plea, “Please.”
“Please what?” she asked, opening her robe a bit to allow me to see more of her white flesh.
I stammered, desperate to see and touch her big breasts that had been untouchable for so long, “M-m-may I touch your breasts, Sandra?”
“You want to touch your baby sister’s titties?” she questioned, pushing me even further to the brink of no return.
“Yes,” I replied, wanting nothing more.
She let the strap holding her robe together fall to her side, and her big right breast popped out in full view for me. Her nipple was erect, which meant she was getting turned on too from this little charade, and I instinctively leaned forward and took it into my mouth. I knew it was wrong, but it felt so right.
Her moan in my ear was all the approval I needed. I sucked it into my mouth and used my tongue to swirl around it, like I had read about on the internet. She whispered into my ear, “That feels so good big brother. Use your teeth a bit.”
Obeying her instructions, I bit her nipple gently and she moaned again in my ear, “That’s it big brother, you are such a bad, bad boy.”
Being called bad boy turned me on, as I had always been perceived as “Mr. Perfect” or “Mr. Good-Boy”. I bit her nipple a little harder and she let out a little yelp and gave a slight chuckle, “You really want to be a bad boy, don’t you big brother?”
I bobbed my head in the affirmative, refusing to let her luscious breast out of my mouth. She gave my cock another squeeze and said, “This is going to be your best Christmas ever, big brother.”
Suddenly, she pulled her breast away and kissed me on the lips shoving her tongue in my mouth. The sloppy but passionate kiss lasted only a second or two, but it was so intense I could feel my juices flowing like never before. Unfortunately, she broke it too soon and whispered, “All good things come to those who wait, big brother.” She pulled her robe back around her body and went back to her room. Just before she was about to disappear from view she turned and added, “And no jerking off big brother. I want you on the brink of pleasure at all times, understood?”
I nodded my head in reluctant agreement, my cock already near the point of no return.
She smiled, “Good boy,” and walked away.
I sat in my chair for minutes, waiting for my reaction to her sexual onslaught to calm down, as I reflected on what had just happened. I had just voluntarily attempted incest and wanted to finish the job. I tried to figure out what Sandra had in mind. She was a crazy girl and, I assumed, a pretty big slut, but seducing her own brother seemed unlikely. Yet, how else could you explain the past fifteen minutes? Unless she was setting me up to humiliate me completely. That scenario seemed just as likely, if not even more so than the scenario that ended with me fucking her. What was I thinking? Fucking my own sister was morally wrong on so many levels…yet, the only thing on my mind was making that absurdity a reality. I was even more determined to make my fantasy a reality, I was going to lose my virginity to my sister…one way or another.
3. MY FIRST BLOW JOB…A PLAN EMERGES
That evening, around 11:30, I was in my room doing research for my one of my papers when my phone vibrated.
I reached for it, wondering who would text me at this time of night. It was from Sandra.
Sister: Big brother, get your ass to Beth’s house now.
I stared at the phone for another minute when another text came.
I texted back: Fine, I’ll be there in fifteen or twenty.
I sighed as common sense had come to me after I had time to think about what had transpired between Sandra and me. Yes, my sister was incredibly hot and I desperately wanted to lose my virginity, but not to my sister. Still, I had decided she could be very helpful in teaching me how to talk to girls, and a party seemed like the perfect place to experiment with talking to girls. They would be younger, dumber, and I would not have to see them at school on Monday if I was rejected. I had also met a lot of her friends and they were all pretty hot and I assumed as slutty as she was. Maybe, she would set me up with one of her friends. Plus, the party was at Beth’s house and she was an incredibly hot British redhead friend of Sandra’s. On many occasions she had been the main attraction of my stroke fantasies. So I quickly got dressed and drove to Beth’s house. Quite a few cars were parked at the house and I quickly realized I was heading into a high school party as a college student. I had never been to a high school party, even when I was in high school, so trepidation quickly filled me. After reconsidering just turning around and going home, I figured fuck it, I am a twenty-year-old man, it was time to stop being a pussy. Suddenly feeling confident, I got out of my car and made my way to the party.
Once inside, there were wall-to-wall teenagers drinking, dancing and making out. I squeezed by the plethora of teenagers, looking for my sister. I was there for fifteen minutes, ignored completely by the masses, before Della, a chubby friend of my sister’s, saw me and grabbed my hand and said, while dragging me, “Come with me.”
She pulled me, through more throngs of people, downstairs into the basement and to a relatively secluded room in the back. She knocked twice and a few seconds later Beth opened it and walked away. I entered the room and Della closed it and locked it. Once in the room I glanced around and realized I was there with Della, Beth and Sandra. Beth and Sandra were playing some dancing game on the wii. Sandra was dressed in a short tight black skirt, a blue skimpy t-shirt and black pantyhose. She was shoeless; I could see her stocking-clad feet, a fetish of mine I could never truly explain. The sight of a girl’s feet in pantyhose was the ultimate turn-on, even though feet without stockings did nothing for me, just another bizarre quirk in my celibate life. Beside her was Beth, also in a black skirt, although not as short, and wearing beige pantyhose, with her stocking-clad feet also in full view. I watched, like a teenage boy, my cock erect, at the two girls moving their bodies to the beat of some song I didn’t recognize.
Della sat down on the floor beside the couch, which perplexed me, as the couch was completely empty. Although quite chubby, she was very pretty and had massive breasts that complimented her chubbiness. She was quite shy and seldom said much the few times she had been at our house. I didn’t move, but returned my gaze to Beth and her amazing legs. Every once and a while, my gaze would shift to my sister. As soon as my cock was erect, I began thinking with the wrong head and all logic faded away. My mind began to replay this morning’s events and I began to think dirty thoughts of my sister and me.
The song ended,Sandra turned, looked at me and smiled, “Hi, big brother.” She walked over and gave me a big hug, her large breasts squishing against my chest. The hug was definitely longer than any hug she had ever given me in the past, but not overtly sexual. However, after having her breast in my mouth a dozen hours earlier, the hug enhanced the sexual tension inside of me. When she let go, she kissed me on the cheek and walked to the couch, joining Beth who was already sitting down. Sitting down beside Della, her eyes never leaving mine, she surprised the shit out of me when she ordered, “Della, my feet are sore, please rub them like a good girl.”
I let out an audible gasp as Della, without a word, proceeded to take my sister’s stocking-clad left foot into her hands and began massaging it.
I continued to stare at the bizarre scene. I looked back to my sister. Her smile broad, confident and seductive, she asked Beth, “Are your feet sore too, Beth?”
Beth responded in a far too scripted way, “Actually, yes Sandra they are killing me.”
Sandra asked Beth, “Would you like my big brother to massage your feet for you?”
“That would be lovely,” she said, her British accent making my cock twitch.
Sandra looked back to me and said, ever-so-sweetly, “Would you be a dear, big brother, and massage Beth’s aching feet?”
I prayed this was all part of my sister’s plan to get me laid as foreshadowed this morning. If Beth was my first fuck that would be a legendary story. My cock leading the way, I walked over to the couch and knelt beside Beth. I eagerly took her sweaty left stocking-clad foot into my hands and began to massage her it. Her purple painted nails looked so sexy and enticing, covered by the beige coloured pantyhose.
My sister explained Della’s position to me as both beauty queens received foot massages. “So big brother, since you so obediently obeyed my request, I think I can explain what is expected of you. You are going to be my personal servant whenever you are home. This includes massages, getting me things, doing my homework and other, undisclosed, things.” Beth chuckled at the implication, as I assumed, of some things sexual.
“You see, at school, parties and cheerleading practices I have my own personal full service servant, Della here, isn’t that right Della?”
“Yes, Mistress,” she replied, never looking up from her current task.
My head spun with the power my sister had over this sweet chubby girl, and the power she assumed she had over me. It was the final straw. All the past two years of her condescending attitude over me had come to a breaking point and I decided it was time to turn the tides on my sister. My mind began racing at the opportunity of not just fucking my sister, but turning her into my personal full-service servant. She was like so many characters in the stories I read, dominant in theory, but really that was just a facade to her real sexual needs…to be controlled. I was suddenly determined and convinced I could make this happen, but I needed to set it up. So for the time being I would have to play along. Sandra continued, patting the chubby girl on the head, “Good girl. Now big brother, are you willing to be my unconditional full-service home-servant?”
Faking an eagerness to build her confidence and imply my weakness, “Yes, Sandra.”
“You will obey my every command?” she questioned.
“Yes,” I agreed, way too quickly to be considered anything more than eager to comply.
“Good boy,” she purred. “Do you want to fuck Beth?”
“Yes,” I replied, this time with no attempt at manipulation.
“If you earn your keep, you will get to do exactly that, fuck the tight cunt of my best friend,” Sandra bluntly announced, clearly showcasing her dominant power among her group.
I looked at Beth whose face was red, seemingly embarrassed by the offer my sister had presented to me, but she said nothing, showing the hierarchy of the group. Clearly Sandra was at the top of the cheerleader power play, with Beth beneath her and Della at the very bottom.
I briefly pondered if Beth too was a submissive to my sister. I switched feet and Beth let out a slight moan. Sandra asked Beth, “Does my brother give good foot massages?”
“Fucking amazing,” Beth moaned, her British accent making it sound even naughtier.
“Well, I better check it out for myself. Della go massage Beth’s feet while my big brother does mine,” she commanded.
Della and I switched places, making eye contact briefly. In her eyes I saw her embarrassment at how she was being treated, but also an excited eagerness to please, like so many subs I had read about. I took my sister’s stocking-clad foot into my hand and began massaging. I should note that I completely understood the science of a massage, and was pretty confident that I could get any women rather horny just by using the right amount of pressure and hitting the right spots…like I had been doing to Beth.
The room was silent as I attempted to trigger my sister’s erogenous zones in her foot that would bring spasms of pleasure throughout her whole body. A slight moan escaped her lips a couple of minutes into the foot massage and she eventually spoke, “Oh my, big brother, you are very good at this.”
I responded, pretending I had no clue what I was doing, “Oh really, I have never done this before.”
“Hmmmm,” she moaned, as I put pressure on a spot I was pretty sure would bring her tingles of teasing pleasure.
A couple of minutes later, Sandra talked to Beth as if I wasn’t there. “So, Beth, as I began to tell you earlier, my brother has a pretty big cock.”
Beth asked, “Have you seen it?”
“Not yet, but I got a solid feel while he was nursing on my breasts,” Sandra announced.
“What?” Beth gasped, clearly surprised by her best friend’s revelation.
My cock had been in an awkward erect position in my pants for a while now and I could no longer resist shifting its position. I tried to do it slyly, but my sister noticed. “Is giving your baby sister a foot massage getting you hard, big brother?”
Faking embarrassment, I stammered, putting my head down, “Y-y-y-yes.”
“Stand up, big brother,” she ordered.
I reluctantly let go off her stockinged foot, a touch I could hold onto forever.
“Show us your cock, big brother,” she demanded, her voice dripping with sexy sweetness.
Playing the game, pretending to be insecure, I responded with nervousness, “No, don’t be silly.” In reality, even though I was a virgin, and very nervous around women, I knew I had a pretty big cock. I had done a lot of research on normal size and so forth. I was a little over 8 inches long. And for some reason, maybe because I had turned this whole silliness into a challenge to defeat her and make her my sex slave, I was no longer nervous. I was determined.
“Now!” she demanded, her sexy sweetness gone. It was clear she was not used to having people say ‘no’ to her.
I shifted to fake pleading. “Please, Sandra, not here, not in front of other people.”
Her smile returned, “You have already agreed to be my personal servant.”
Again feigning innocence, I argued, “But that didn’t include showing my penis.”
“Your penis,” she cackled, “now that is funny. Don’t you mean your cock?”
I lowered my head again and pretended to be a prude. “I can’t say that word.”
“Say it!” she ordered, her smile gone, her tone demanding.
I whispered, so quiet no one could hear it, “Cock.”
I repeated the word loud enough to be heard, “Cock.”
“Show us your cock,” my sister demanded.
“Please don’t,” I pleaded one more time.
“Now, slave!” she ordered, pushing the envelope.
Deciding to look completely whipped, defeated and weak, I responded, making a very conscious word choice, “Yes, Mistress.”
As I began to unbuckle my pants, her smile returned and her tone implied complete triumph, “Mistress, I like that big brother. For now on when we are in private, you are to refer to me as Mistress Baby Sister, is that clear?”