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.

Sister: NOW!

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."

"Louder!"

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?"

"Yes, Mistress Baby Sister," I replied, like a brainwashed sub, as I allowed my pants to drop to the floor.

She pulled up her skirt a bit, opened her legs and tore her pantyhose at the crotch. I got a quick glimpse of her pink pussy as she was apparently commando. She demanded, "Slut, get to work."

I watched as Della quickly crawled between my sister's legs and dove into my sister's pussy.

Sandra continued talking to me as if it was normal to have someone between her legs while talking to her brother, "Now your underwear, big brother."

I discarded my underwear and released my fully erect cock to my sister and her beautiful redheaded friend. "Oh my," Beth said, the impressed look on her face sending a chill up my back, and building me with much needed confidence.

"Oh my, indeed," my sister concurred, staring at my stiff cock.

"Do you want to fuck it, Beth?" my sister asked, thoroughly matter-of-fact.

"Five minutes ago I would have politely declined, but now I may have to reconsider," she said, standing up and walking over to me.

My sister offered, "Well, you better go and inspect the merchandise."

Beth laughed, but surprised me by dropping to her knees. Her British accent was so sexy as she complimented me again, "I shouldn't, but fuck, it looks so damn tasty."

She took my cock in her hand and slightly stroked it. A spasm quaked my body and I was worried I might come.

Sandra, leading her on, teased, "Go ahead Beth, suck it. You know you want to."

Beth looked back at Sandra and challenged back, "You want me to suck his cock, don't you?"

Sandra shrugged, acting all innocent, "Maaaaaaybe."

Beth turned back to me, looked up from her subservient position, "So Matthew, do you want me to suck your big cock?"

"Desperately," I responded, no longer playing a game with my sister.

Beth looked back at Sandra and said, "Last chance to stop me. I know you want to suck it too, Sandra."

Sandra shrugged, "Maybe, maybe not. But for now I will be content watching my big brother get his first blow job."

Beth smiled up at me, "Matthew, you would get a lot more pussy if girls knew what you had hidden behind your geeky exterior."

Before I could respond, Beth opened her pretty little mouth and leaned forward. Her warm mouth felt more amazing then anything I had ever felt before. My body melted and my mind went to mush. She began slowly moving up and down on my cock, taking about half of it in her mouth. In less than a minute, I could feel the undeniable boiling in my balls and knew I was going to come soon. Deciding to throw a slight amount of doubt into Sandra's master plan of sibling dominance, I grabbed Beth's head and held it in place as I quickly face-fucked the gorgeous red-headed cocksucker. She let out a surprised sound, but after only a couple of pumps between her sweet lips I was shooting my cum down her throat. When I was done coming, I let go of her head and quickly apologized, stammering for full-effect, "I-I-I am so sorry B-B-Beth, I don't know what came over me."

I looked up at Sandra who seemed surprised by my aggressive action, but seemed just as quickly to fall for my blithering idiot apology. Beth looked up at me surprised as well, but instead of being angry, responded, yanking on my cock one last time, "No problem, Tiger. I like a man who knows what he wants." Standing up, she turned to my sister and added, "Your brother's cum is yummy."

Sandra moaned, as Della between her legs was clearly getting her horny as well, I assume, she was also getting horny from my little show with Beth. Sandra trying to re-establish her power in the room over the rest of us, demanded, "Get me off, my sub, now."

Della's head began to move back and forth a bit and I saw her right hand disappear between my sister's wide spread legs. I watched intently while pulling my underwear and pants back up.

I announced, "Well I should get going."

"Don't you want to watch your little sister come?" she pouted dramatically.

"If you wish, Mistress Baby Sister," I responded, attempting to manipulate her by giving her a deceiving amount of confidence.

"I wish, big brother," she moaned, grabbing Della's head and pushing it deeper into her pussy. "I'm so close, big brother. Watching Beth suck your big cock was so fucking hot. Be a good sub for me and you can fuck Beth. You can also fuck Della, she loves it up her plump fat ass. Ummmm, yes, I'm coming big brother, yes, yes, yeeeeeees!"

The thought of fucking Beth was enticing, as was the thought of getting in Della's back door, but I was now more determined than ever to lose my virginity to the hottest girl I knew ... my sister. I watched my sister collapse back on the coach as an orgasm exploded through her. Deciding now was the perfect time to leave, I looked at Beth and said, with sincerity and befuddled innocence, "T-t-thanks Beth, that w-w-was awesome."

Beth chuckled, "No problem, Matthew, the pleasure was all mine."

I had a witty comment back, but decided not to make it and said, "I hope to s-s-see you again, Beth."

Beth responded, "You never know."

"Oh, I know," Sandra said, adding her two cents' worth.

I gave a half wave and left the room and the party and drove home, my mind spinning deviously. Tomorrow I would start my plan to make my sister, my slut.

4. A PLAN IN ACTION

Sandra didn't come home that night doing who knows what with who knows who, and didn't arrive back home till the evening of the 23rd. I had a variety of ideas to turn my sister, but they all required being alone. Now that was no longer an option. Mom and dad were home and we were watching the news when my little sister dropped on the couch beside me.

Mom asked, her tone implying the answer better be no, "You are not going out again, are you?"

"No, Mom," she replied, "the 23rd is tradition."

"Good," Mom responded, clearly relieved.

The 23rd was always Christmas movie night, a tradition since as long as I can remember. Sandra picks the first movie and I get second choice.

Sandra squeezed my leg subtly as she used it to push herself up. She stretched, her tight jeans leaving nothing to the imagination, and said, "I am going to get in my jammies, then it is time to watch Home Alone."

Mom stood up also. "Well, I will go make popcorn and hot chocolate while everyone else gets comfortable."

I too got up and went and changed into my evening wear. My parents' house is quite chilly in the evenings, so it usually includes flannel pyjamas. In my room, I took off my jeans and, on the spur of the moment, with a potential plan popping into my head, I also discarded my underwear. I threw on my flannel pyjamas and returned to the couch. I grabbed a blanket, one big enough for Sandra and me, and waited. The genius of the plan spinning in my head was that the way the living room was set up, both Mom and Dad sat on their favourite chairs, and neither could see us without turning back, which they seldom did. My plan relied on oblivious parents and my blanket. Sis returned in what could in no one's definition be called pyjamas. She wore a halter top that barely held in her big tits and Lulu Lemon short shorts. It was the exact outfit I imagined when I fantasized about an all-girls' slumber party. She smiled at me and joined me on the couch, slithering under the warm blanket before either parent saw her whore-wear. I wondered if she was thinking of toying with me in the same manner I was planning on toying with her. It was a game of sexual chess, and I was a whiz at chess.

Mom returned with popcorn and hot chocolate and like the 1950s June Cleaver Mother she was, she made sure we were both comfortable before the movie started. As the movie began, my head spun with how and when I should initiate the plan. Knowing we were watching two movies, I played it cool throughout the first movie. Sandra attempted to distract me by putting her hand on my leg a few minutes into the movie, but she was clearly not as confident and brazen, with our parents in the same room, as she had been in the kitchen just yesterday. I decided to make my move when the bad guys in movie were finally inside Kevin's house. It was now my turn to be brazen. I grabbed her hand, and in one quick lightning strike, led it inside my pyjama bottoms to my semi-erect cock.

She let out a surprised yelp and both my parents turned around. My Mom asked, "Anything wrong, Sandra?"

Her face flushed, her hand wrapped around my cock, my parents completely oblivious to the incestuous act currently happening right behind them, and she covered well. "Oh nothing Mom. I just always jump when Kevin almost gets caught."

My dad chuckled, "Oh Sandra, you never change."

I thought to myself, 'If you only knew the half of it, dad.' The movie continued and I looked at my sister, my timidity now gone, my confidence now growing along with my hard-on. I reached under the blanket and, using my hand, made it clear what was expected ... a hand job.

She smiled, seemingly impressed by my aggressive out-of-character action, and began slowly stroking my no- erect cock.

The rest of the movie flew by as my hot sister slowly stroked my cock. The movie ended, and when dad stood up, Sandra went to pull her hand out of my pyjamas. I grabbed her hand, startling her, and held it in place. My dad turned to me and asked, still oblivious to the power struggle happening right in front of him, "So what movie next, Matthew? Let me guess, Jingle All the Way."

Every year since I was eight, I had picked Jingle All the Way, an Arnold Schwarzengger Christmas movie that was just so bad, yet I loved it. I wanted to be the Turbo Man when I was a kid. I let go of my sister's hand and, as I expected, she didn't move it off my cock, and said, "Of course, Dad."

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