The Step Sister Ch. 01



Okay…before I start this whirlwind story of my younger life, let me begin by describing myself today. My name is Matthew Wilson, I am married with 2 little boys, I am 29 years old, 6’4″ at 260 pounds with very little body fat, I am an avid bodybuilder since I was 15, I am an Accountant for a major Firm in Colorado and I also own my own personal training company with over 50 full time clients currently under my belt.

I graduated High School salutatorian of my class, graduated from my University in Colorado Summa Cum Laude with a dual bachelors in Accounting and Mathematics, I also earned my Master’s in Accounting and Management…needless to say my academic and fitness life through my college years was pretty arduous and chaotic. The only real “slow down” time was during my Summer Breaks when I would fly back home to my dad’s house in Arizona. I elaborate on this because the summer between my Sophomore and Junior year of my bachelors program when I was 21 is where my experiences with HER began.

When I was 10 my mother passed away and my father was just so devastated that he didn’t even begin dating again till I was about 16. After having met and dated a few women, he met Natalie, a gorgeous and sweetheart of a woman, and they hit it off great…and the summer when I was 18 about to go off to college, about 2 years into their relationship, he actually married her. Well…Natalie had a daughter from a horrible prior marriage named Mary.

Mary and I were both 18 and were already set to go off to our own separate colleges by the time the marriage took place. During the timeframe of our parents dating, we slowly developed our own friendship. We all lived together through that summer after the wedding and of course the following summers in between our freshman, sophomore, junior and senior years of college. This induced Mary and I to spend a lot of time together, and our friendship really grew into a best friendship that made us inseparable when we were home! Not many late teenage step siblings actually become good friends like that with each person having their own clique of friends and such…but we actually grew close!

Now Mary was extremely beautiful and I’d be lying if I said any different, she was 5’7″ with smooth sun tanned skin, tight abs, perfect curves, a full toned ass, a beautiful face with blue/green eyes and full lips with long blonde hair that stretched to the top of her ass, and a pair of very perky DD breasts that stood by all terms of the word perfectly, almost to the point that had I not known her for so long, I would have suspected they were very well done implants. Like I said, I would be lying if I said I didn’t find Mary extremely attractive and that I would have given anything to do anything with her.

She was gorgeous, smart as hell, sarcastically funny and such an all around sweet girl. But, naturally I never acted on any of those impulses because she was my step-sister and even though that was just a legal/social formality, it was morally wrong in the public’s eye. Also I was just happy that her and I grew to be as close of friends as we have. That would eventually change though, as you probably have already guessed it!

For those summers, Mary and I grew close as hell as step-brother and step-sister, we would go to movies, go out to eat, go hang out with our sets of friends, and we would play drinking video games (drunk Mario Kart and Smash Bros) all of the time and usually end up passed out over each other, leading to some nasty next day hangovers for the both of us. Though there was that sexual appeal I had for Mary, I really never acted on anything as I just enjoyed her company as my best friend for the summers since most of her friends as well as mine didn’t really come back home from college during those times.

While we were at our universities, we would usually text daily and see how each other is doing, talking shit, confessing funny hookup/ one night stand stories, or just bombarding memes to each other while we were in our classes. It was because of this fun relationship we had that I never thought of acting on my physical wants toward Mary. I had my trusted hookup partners at school and back at my home city, so I wouldn’t think to long about Mary in that light. I also never thought she found me attractive like that, I knew I was attractive, but I assumed she looked past that.

Now I wasn’t 260 pounds back in college like I am now…but having been bodybuilding for 5ish years by that summer…I was sitting at about 230 pounds with a cut waist and a lot of definition (I always would cut up and get striated for summer pool season, as most young bodybuilders do). I felt I looked really good to most women that would see me this summer, excluding Mary of course.

The day I got back from University, both Natalie and my dad were working when I landed and since Mary arrived ataşehir escort bayan the day before me, she was coming to pick me up at the Airport. After grabbing my bags and walking through the terminals to passenger pickup…I saw her. She was waiting for me in person, she must have parked the car and came to give me a proper long awaited ‘Hello’ greeting. All she doing was smiling at me the whole time I was making my way to her.

She was dressed overly nice to pick me up, wearing a skintight Crimson dress that seemed to cut just above mid-thigh. This dress showed every curve she had perfectly… Her ashy blonde hair had soft long curls and her makeup was very beautifully displayed, even though she really didn’t need any makeup to look gorgeous. As I was getting closer to her I noticed all of her wonderful features from her long toned and tanned legs to the V-cut of her dress making her breasts almost pop out for me to see, which I wouldn’t have complained if they did! I don’t know if it was just not having seen her for the months of that last semester, or my own hormone fuelled sex drive, but she look than I ever to me in that moment.

‘God damn she is so fine’ I thought, ‘everything about how she looks is fine from hair to heels! What I wouldn’t give to bury my co..’

Then I realized what I was thinking and shut that shit down quick! ‘What the fuck are you thinking’ I chastised myself, ‘she’s your fucking step-sister…no matter how hot, that shit isn’t going to happen. Besides she doesn’t see you that way, she’s probably going on a date or a girl’s night out tonight and you just haven’t seen her in person in 6 months…’ I had to relax my brain quickly as I felt a little extra weight hanging between my legs as some more blood started to flood down south.

As I got closer and closer to her, I could tell she was giving me an up/down inspection. Nothing crazy…just one of those head to toe and back to head with an approving smirk. It had me question what that was for…we had grown close as hell but she has never given me the ol’ “up down” with a sign of approval… Naturally I suppressed my second guessing on that as well, our parents were married to each other and it would be like throwing a brick in a dryer for our family if I tried to do anything with her. Plus she’d probably slap the shit out of me if I tried to make a move and I knew she was built just enough that it would fucking hurt like hell to get hit by her!

“Holy shit Matt!” She practically shouted at me as I walked up and stopped in front of her. ” You look amazing! Dude you’ve got even more buff this past semester!”

“Hey homie!” I laughed “Thanks! What can I say, iron addict for life!” I chuckled at her.

“With all your gym shit, how do you find time to study?” She giggled back at me.

I gave her my witty grin and replied “You know I don’t sleep…”

With an elongated eye roll, she wrapped her arms around me and gave me probably the biggest, tightest hug she ever has. I could feel her firm breasts pressing against me, and her floral perfume smelled nothing shy of heavenly, Rose and Jasmine. I started to feel myself grow more downstairs at the feeling of this sexy woman pressed against me.

‘Matt! Fucking stop!’ I whipped myself mentally ‘she’s still family and she’s definitely going to feel it against her stomach. Shut that shit down!’

“Let’s get to the car, I want to get home and relax.” I said as I broke the hug and grabbed my bags “What’s on your agenda for the rest of the day? Date night? Girls’ night?” I asked.

“Absolutely nothing honestly!” she said with a little chuckle “I figured I was going to chill with you for the day, catch back up on everything with you.”

We started walking to the car, I couldn’t help but think to myself, ‘Was she dressing like that solely for me then? Did she want me to see her in a lustful way? Why would she want me to see her like that? Why the hell am I more turned on by her than I should be? What the actual fuck is wrong in my head?’ I felt like I was my own Commanding Officer shutting down what my brain was thinking. I knew I either needed to rub one out at home or try to hook up with one of my old FWBs tonight. I didn’t need to have these thoughts already.

After walking some distance and asking each other the normal questions that you ask when catching back up with someone, we made it to the car. On our way home I kept looking at Mary in the corner of my eye as she drove, her skin was just as smooth as I can remember, and her cleavage was just spilling out of the top of that dress. The bottom of her dress shifted up when she sat down and I could see the starting tip to her black lace thong.

I couldn’t keep staring, and I couldn’t keep thinking that she dolled herself up solely for me. I had to say something to her in hopes of getting a sibling’s response to escort kadıöy ease my mind of this unneeded sexual tension, but the back of my head secretly wanted a sexual response. So it was a win/win situation I figured. I knew I just needed to be sly with it because, well, saying something just forward enough would make shit too damn awkward for us after that.

“Hey,” I stated “about your comment you made about how I looked back there,” I said as she looked at me periodically while she was driving “I’m sorry I didn’t return a compliment back to you. Truth be told…and as off putting as it may sound with you being my sister, I was honestly just shocked at how beautiful you looked in the dress that I really couldn’t find the words to say back with out making myself feel awkward. Like you captivated the room with your looks, there’s no denying that I, and every other man with a pulse saw it.” While being a smooth talker, I was waiting for some thankful, non-sexual style response…

‘Please say something sisterly…’ I thought.

“Step Sister.” She replied with a small smile.

‘Well Fuck.’ I thought. ‘That’s just maddening the unhelpful.’

“What?” I asked, knowing damn well what she meant by that.

“I’m your step sister dude, not your blood sister.” She said with an honest grin “If I were your blood sister, then fuck yeah that would sound a little off putting…but I’m your step sister, your step sister you met at 16…it’s okay, and kind of cool to know you with your looks and size think I look good!”

“Really?” I asked “You’re ok with me telling you that I think you look gorgeous? It’s not weird to hear that?” I made sure she saw my quizzical look on my face. Though I was getting an answer I was liking, I still was in disbelief she likes that I think she is hot…

“Yeah!” she replied “Hell I think you’re a very handsome guy, always have, and I’ve told you plenty of times! And your newer found muscle size you keep putting on makes you even more attractive! I don’t mind you seeing me with attraction, because I put a lot of work into trying to look good just as you do the same with your bodybuilding! It’s perfectly normal to see each other in the attractive sense. Also, you don’t compliment me like most guys our age…usually its ‘you have a fat ass’ or ‘you’re hot as fuck’…but you saying I look beautiful and gorgeous…I actually like it” she looked over at me with a smile, not a genuine happy smile, but not a wicked smile either…this smile was a mixture of both.

‘Holy shitballs!’ I was screaming in my head ‘She thinks you’re hot as well!?!? Maybe I should try..NO! Shut the fuck up Matt…she’s family and you’re not going to make a move on your own family!’ My internal monologue was fighting with me so hard by this point. I was starting to feel like I had a touch of crazy with how much I was talking to myself in my head.

As I was arguing with myself in my head looking out the window…the rest of my body slightly flushed from what I had just heard, and I didn’t take notice that I had grown rock fucking hard from her words. After I noticed the obvious bulge, I grabbed my backpack from where my feet were sitting and I brought it up to my lap.

I looked over and saw a little smirk in Mary’s face while she was watching the road.

‘Dammit…Did she see my bulge in my board shorts?’ I thought ‘Is that what she was smirking at? Jesus Christ I need to just rub one out when I get back to the house and clear my head…I don’t know if I’m going to survive this summer.’ I laughed to myself in silence as I thought of how hard it was going to be to maintain composure for all the times we were going to be in the pool together, seeing her in her bikinis…

Mary and I continued to make small talk catching back up about events these past two semesters, friends we’ve made and lost, and how schooling was going as the drive home was coming to an end.


After a couple hours of laundry and unpacking everything I brought home, I decided to give myself a little alone time in my room to go at it and drop the thoughts of Mary out of my head. I knew it was wrong to think about her while beating off since she is family technically…but I needed this release to happen…I mean come on, she was honestly smoking hot picking me up…and let’s face it, it wasn’t the first time I thought of her while doing it. With the excitement of this release that needed to happen, I completely forgot that Mary said she was just going to chill with me all day…and I forgot that I hadn’t locked the damn door. Rookie move.

After folding and hanging my clothes, I plopped down on my bed, unzipped my zipper, and began to do my thing. And my cock was as hard as a diamond, fully engulfed with more blood that I thought could fit in it. Part of me felt bad because this wasn’t the first time I have jacked off maltepe escort to my sister’s mental image…hell it probably wasn’t even the 50th time…but she is flawless in the most unbiased sense!

After a good while into my session…Mary came barging through my bedroom door asking me “Hey do you want to go out to eat or order somethAAAHHHHHH! Oh shit!” She jumped back exaggerated.

“Oh what the fuck!” I yelled at her as I reached for the edge of my comforter to throw over me. I felt like my heart just blew out of my damn chest like Chestburster from the Alien movies.

“Oh my god I’m so sorry!” she proclaimed as she was staring wide eyed straight at my dick before doing a complete 180 and bolting out of there.

She ran out of the room as I laid there shocked and stunned at what just happened. The scare of it all of course made my cock eventually go flaccid and I knew this pleasure session had come to an end for now.

‘Great’ I thought sarcastically to myself ‘I get to have an awkward situation with my stepsister and blue balls all at the same time…fucking great! Well…I’m getting out of here, fuck that!’

After zipping back up and collecting my composure…I texted my buddy Eric who was back from college for a couple days before going on a trip to Europe. He said I could come over and chill with him for the night once he got home in an hour. So I decided to play a little Call of Duty for about an hour before leaving. As I was making my quick way out of the house, I saw Mary sitting at the kitchen bar having a snack. Our eyes locked for a moment before we both made the awkward “look away” move. I walked passed her and said “I’m going to Eric’s for the night, tell Natalie and Dad I’ll see them after they get off work tomorrow.”

Mary tried to respond as I was bolting out the door “Okay, wait Matt I…” but the door closed behind me and I dipped out before I could make shit any more awkward. I needed to get away from her for the night, have a drink and calm my bullshit nerves before talking to her again. I was obviously way too turned on by her and it needed to stop.

Through the night at Eric’s house, we trained that night in his home gym as he was another bodybuilder, played way too much Call of Duty, drank about a fifth of Bourbon and smoked a sizeable amount of weed. It was honestly just what I needed because the next day around noon, when I woke up, my nerves were calm and my anxiousness with Mary was gone. I knew the conversation about what she caught me doing was going to be awkward, but I mellowed my nerves enough that night to get a grip on myself.

I got home around 3 that afternoon and though the nervousness of talking to her built up a little bit when I saw she was home, I knew we were still great friends and I made a mountain out of a molehill for nothing. I ventured back into the hallway and to the living room where Mary was watching TV acting like nothing happened. I walked over to her, sat down at the opposite end of the couch and knew I needed to talk to her…

“Mary can we talk?” I asked

Mary muted the TV and turned her body to me to give me her full attention. This didn’t help much because she had another tight summer style dress on, her tits eye level to me to look at…and a different black lace thong was facing directly at me. And I knew what was right behind the thin piece of fabric…that delicate shard of cloth keeping my eyes from seeing her beautiful core.

Did I know it was beautiful, no…but I imagined it was just like the rest of her body…perfect in every way. And my cock slowly started to grow again, creating yet another bulge…but I wasn’t as hard as I was in the car so the bulge wasn’t as pronounced. The nervousness built up more now that I had her attention and more so that she definitely had mine.

“Look Mary I am so sorry for that, what I was doing, what you saw…there’s no doubt that I do it or you do it…we both do, hell were adults, but I should have locked the door. I should have thought ahead and made sure you wouldn’t have had to see that and I apologize for that. Can we just drop it though and forget about the whole thing?” I pleaded with her.

“Dude I know you jack off, fuck we text each other our hookup stories all the time!” She laughed “I just felt bad that I didn’t knock first and probably fucked up your whole chi”

I began to relax at her nonchalant attitude. “Yeah” I chuckled “my chi was definitely broken from that!”

She laughed at my reply, but that quickly left her face as I could see she had a distinct firmness to her. It was like she had her thoughts on something and she was trying to think of how to express them.

“What were you thinking of?” she asked me curiously with a straight face.

‘Huh?’ I thought

“What do you mean?” I replied, giving her a quizzical look.

“What were you thinking of while you were masturbating, or beating off, or whatever you prefer to call it? There wasn’t any porn playing or any pictures you were looking at…so what were you thinking of?” She chuckled “I would have taken you for a POV fan or a VR fan with porn since you’re a tech lover!”

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