Sex with My Boss's Sister | 2016

I'm not going to give a code to this story. But I will give you a hint. His sister is involved and he isn't. And I am the only other guy in this story. You can figure the rest out.

That is my dickish attempt at being funny. I have a deadpan sense of humor 90% of the time. Onto this story, this takes place about two months after The CoWorker Chronicles ends. I won't give spoilers, but the rest of that series, with the exception of the last part of the last part, ends about two months before this. I was still hurting over that, and that no doubt influenced this story, but I was more over it than if it were to have happened the day before.

Also, I was 20 at this point. I turned 20 in June, and we are currently in the end of April in that story. A little older and a little wiser. I give you this information because this was my first sexual encounter (well, second, but like I said, no spoilers) after Julia. And it was hot.

Now, without further Adieu...

I had just left a job I held for freaking ever to get into personal sales. I won't give the name of the company, because I really don't want my old boss to read this.

I told him in the interview that I would be the best rep he ever trained. He normally doesn't hire people without cars. He hired me on the spot because of that.

I was there for about two months before I met any of his receptionists. But I ended up hitting it off with one of them, and we eventually became really good friends.

I was fresh off a bad romantic situation when I started with this company, but eventually, I ended up getting for the most part over it, the whole series of the Buffy spin-off Angel and a LOT of sad writing later.

I visited my friend at work one day. She was with two other people, her other work friend (side note, my friend, her other friend, who will be called Dyke since she is one, myself and one other person all got hired together) and another really cute girl I didn't pay too much attention to.

I had a huge crush on my friend, but she was in a committed relationship, so I didn't push the issue. I went there, hugged her, bullshitted and proceeded to get piss-bad drunk with my Marine friend that night.

The next day, my boss calls me and asks if I can help run a training. I have an extensive communications background and I was quickly becoming an office leader, so I thought it would be a good opportunity to assert myself.

I ended up getting there an hour early and called him. He didn't tell me he was going on drill (he was a Marine Reserve) and his assistant manager was running the training, so after I told him I was at the office, he called his sister and had her come get me inside the building. (Another side note, he is an early riser and his AM is the type of person who shows up like five minutes before everything she does.)

About fifteen minutes passed, and finally, the person I had to assume was his sister showed up. She was the same cute receptionist from before! And it was just me and her in the office. I muttered "Penthouse!" to myself, and walked up to her car. After thanking her a billion times, she finally let me in. We were there by ourselves for what would eventually be two hours, so she just logged in to her phone and we sat and talked.

I found out she had just graduated, she was taking a year off, she loved working for her brother, and she just ended a year's relationship. We really bonded over that. After Julia, I was pretty torn up, and I was past it, but I didn't really talk to anybody about it.

I told her in detail about what happened. Not quite as much detail as I've shared on here, but enough to know that we fucked quite a bit and that she was someone I cared about.

She gave me her number, and told me to text her sometime. Eventually, the AM came in and I went to greet her. As soon as I left, I took my phone out and texted her "Has sometime arrived yet? ;)"

She replied "Only if you want it to be, cutie ;)"

In this moment, from the conversation where she was constantly touching me, laughing at all my bad jokes and how eager she was to give me her number, I realized my boss's sister had a crush on me.

My boss's sister.

My Marine boss's sister.

My cagefighting boss's sister.

The same guy who could break my neck in two seconds flat.

Now, I'm a decently strong guy. I'm a greenbelt in Taekwondo, I'm a brown belt in jujitzu, I'm a trained boxer and I'm a trained mat wrestler, but this guy would kill me. He's half my size, way more in shape and has the added incentive of (what was fastly becoming a friendship) a new buddy putting it to his baby sister.

I rolled with it. We flirted that whole day, and she found reasons to come out and mess with me. Finally, there was a part in the training group that AM did where she needed me to go sit in the other room, since I was already a sales rep, and I would skewer the exercise. I decided to go do some dishes while this was going on.

My boss's sister came up behind me. Scared the moose piss out of me.

"That wasn't nice!"

"I'm not nice!"

"I can see this!"

She looked me right in the eyes with a really sexy look on her face, and said "why don't you do something about it."

This happened in three seconds, but I knew what would happen as soon as I looked at her. She was biting her lip in a really cute way, and I was really attracted to her. I kissed her. She returned it.

I kissed her, and she was an amazing kisser. But she's a pack-a-day smoker and you could taste it on her tongue. That turned me off a little bit. But I still had the smoking gun in my pants, and she definitely felt it when I pushed her up against the wall.

I was at least 3 times her size. She is a blonde, has amazing C cup tits, an incredibly nice ass and is country through and through. She is still probably one of the top 5 most attractive people I've ever met. And she knows how to use that cute little butt.

We broke apart and AM called for me. She started walking away, dropped something and bent over in front of me, and hiked her skirt up a bit.

I saw her ass in a really tiny thong, and I knew at that point that there was no way that I wasn't going to fuck this girl. However, doing it in an office full of people (this was a former dentist's office converted into a personal sales office. Wasn't happening this time) was not the best idea. We'd definitely get caught. But I put my dick (covered in jeans) right up against her ass, and she grinded back.

She moaned a bit. "Oh my god, that feels so nice. I want it so bad."

I stood her up and kissed her again, fixed my boner (giving her a good view of my dick in the process) and walked into the training room.

The rest of that day and the next one went by without too much fanfare, just work flirting and A LOT of making out. I was so into this girl. I just wanted to bury my dick into her. Plus, I won't lie, at this point, I didn't even care that her brother would kill me. I just wanted it, and I would give it to her like I would never fuck again.

We kept texting over those two days. After the second day, we were texting late at night and she asked me if she could see my dick.

"You already got a good view of it at work ;)"

"I wanna see all of it."

I snapped a picture and sent it to her.

"Oh my god, I'm so wet now!"

I stress that I was joking when I said this. Now, the training the company puts on is unpaid, and they do it on Thursday, Friday and Sunday. I won't explain why, but that's the reason I said this: "The office is gonna be empty tomorrow (which was a Saturday). I'm sure my schedule will be completely filled, but I'm sure I can squeeze some time in to completely fill you up ;)."

Ten minutes, no reply. I was terrified. I thought she may have told her brother, that maybe I was being set up and he was going to kill me. I texted her back saying I was only joking, that I respect the interoffice boundaries.

She texted me back five minutes later. "Shut up, you're fucking me in the office tomorrow."

I proceeded to rub out what felt like a mountain in between my legs.

Saturday came. I didn't even try to stay soft. I texted her and told her I was on my way. She told me to come in through the back. "I hope that's not the only time I hear that today ;)." "Lmao just wait and see ;)."

I got there. And we made small talk for about twenty minutes. She had ordered pizza and she was waiting for it. When it got here, she was on a call, so I bought it for her, using my money even (chivalrous, I know. I do try.)

I gave him a ten dollar tip, and I told him that was good karma for what was hopefully about to come. He laughed (he was a regular) and said if he knows what I mean, then I'm an incredibly lucky dude. And he knew it was just me and her in this building, so he wasn't dumb. He knew what I meant.

He left and as soon as I got back into the reception area (the main lobby, her office is in the back), she grabbed the pizza, put it on the desk and pulled me into the nearest office.

We made out for at least five minutes. I wanted this girl so bad, and my hands were all over her. I was grabbing her ass, playing with her tits through her t-shirt ("mmm yes") and finally, my pants came off. My dick was sitting there fully at attention.

Now this is where it gets interesting. On the desk I'm sitting on, I'm standing at attention and this girl told me she doesn't give head. It's gross, and she prefers to just have it shoved in her.

She pounced on that shit and gave me an amazing blowjob. She slurped, she sucked and she licked. I wasn't paying too much attention to my surroundings, but I thought the room looked familiar, yet I was too into what was going on.

After ten minutes of this amazing blowjob, I warned her that I was gonna bust. She said on my tits. I took my dick out of her mouth and this is still one of the most amazing things that has ever happened to me.

She ripped her shirt in half, exposing her bare breasts to my throbbing hard dick.

In half.

Yes.

Hulk Hogan style.

That got me even more excited, with it being the sluttiest thing she could possibly do. I busted everywhere. On her face, On her tits. Some went in her hair. She used her now-useless T-shirt to clean it up.

Another quick side note, to keep believability in this story at a high. The office was locked up, which was the norm on Saturdays. She was the only one there, the office is in the middle of nowhere and nobody ever came in the office on Saturdays (except me, ba-ZING!). This was an extremely low pressure situation.

Until I noticed where we were. I looked up on the wall, and that's when I saw my boss's Marines picture looking back at me. I just came on his baby sister in his office! I started freaking out on the inside, but before I could think about it, his sister got up, got in between me and his desk, took off her jean shorts (I still find this weird. She had a skirt on before, yet she knew she was getting fucked and she wore jean shorts. WTF lol), spun me around and put my dick right up against her pussy.

She looked me in her eyes. "Tell me how bad you want it." "I want it so bad (trying to push it in as I said it)." She let go of my dick. "Not until you stop freaking out about my brother." I knew that wasn't going to happen, but hey, I'm a good actor. "Don't get me wrong, I'm certainly not going to bring this up to him over a beer and wings anytime soon (I was underage so this was purely sarcastic), but I'm a lot more worried about burying my dick into that tight pussy than-"

She cut me off by pulling me by my dick towards the desk, got up on it, and I thrusted forward right as she pushed against me. Half of my dick was shoved in. She was wet, not as wet as Julia was, and she was tighter than Julia. I almost blew my load right there again. But I didn't. I did start fucking her with so much force that the desk cracked a bit.

I wasn't even trying to be quiet. "Damn girl, this pussy is out of this world, oh my god!" "MMM, [silverbackjp] give me that dick!" I have to stress that she was still being quiet.

I pulled her hair while I was fucking her brains out and I told her to scream my name. She moaned. "The people next door will hear us, and my ex works over there. MMM shit baby, don't stop!" I thrusted even harder, and said without hesitation "I want them to hear, holy shit, I want them to know just how hard I'm fucking this pussy. I want them to know just how tight this pussy is!"

"MMM HOLY FUCKING SHIT [SILVERBACKJP} I'M FUCKING SQUIRTING!" She bellowed that. Her brother may have heard that where he was. And she squirted. All on my dick. I stopped just long enough to feel her squirt. As soon as i felt it end, I picked up the pace again.

I started fucking her even harder. She came on my dick again.

"Shit [boss's sister} I wanna hit that tight pussy from the back."

"MMM take it out and make it quick then!"

In one motion, I took my dick out and turned her around, and she put my dick in her from the back again. She shook her ass a little bit and she was grinding on my dick while it was in her. In this moment, I looked down, saw what heaven probably looks like with my dick shoved into her tight snatch from the back and realized how lucky I was. I didn't even know this girl's name until a few days ago, I completely ignored her (albeit unintentionally) the first time I met her, and I liked someone else at the office, yet here I was, with all of my dick inside her, and her fucking me in her brother's office like her life depended on it.

We fucked in that position a good twenty minutes. Finally, with my dick still inside her, I spun her around, got her on her stomach and I started fucking her from the back missionary style, grinding my dick into her pussy.

"You like that, baby?" "Mmm, fuck yes baby, give me that big dick." I swear to you, she told me she wasn't a slut, and in the conversations I've had with her exes, they told me she wasn't either. She just wanted me that badly (which doesn't nothing for my inflated ego from this). I kept whispering nasty things in her ear while I was shoving my dick into her. I felt myself getting ready to blast and I told her.

"Not yet, I want you to fuck me up against the wall!"

I assumed at this point she was so horny that she wanted to just rub it in the cotenants' faces that we were having such amazing sex in this office on a Saturday, so I didn't think about it. She wrapped herself around me and my dick, and we fucked like that for a few more minutes. I felt myself get ready to bust again (Awe shit baby, I'm about to fucking cum). Another side note. I am not usually this loud during sex. Something about this situation just made me this way.

She said take it out, she wants it on her face. I took it out, she spun us around so that she was the one with her back towards her brother's desk, and she started jacking it. As soon as my balls tightened up, she ducked. My whole load hit her brother's desk...

I realized what happened and I started freaking out again. She told me to relax, she'd clean it up. Later. She giggled and we kissed. Again.

About her clothes. She really prepared for this. She had a spare set in her office. She put a hoody and some leggings on (which were taken off about an hour later in her office as I plowed her from the back against her desk, with my load going squarely in her birth-control having vagina) and we went back into the lobby and ate the pizza, laughing and basking in what just happened.

We never dated. I don't think either of us really wanted to. And we never hooked up again after this. We never really had the opportunity and I was terrified of her brother finding out. I stayed there for a year and a half, just leaving this August. She's still a really good friend, and her brother is one of my best friends to this day. I still pray he never finds out, but I did find out she hooked up with another rep after I left and he wasn't too mad about it. Maybe I didn't have too much to worry about.

I have a hard time believing he'd be cool with me jizzing on his desk though.