I had sex with my boss’ daughter.. and her friend. [mff]

So…one night I had sex with my boss’ 21 yr old daughter and her 19 year old friend. Which was pretty awesome but if he finds out my life is likely to change drastically. I’m 38, a single dad and work as a professional photographer. Couple years ago I went through a gnarly divorce and had to sell my house and pay $25,000 cash on lawyers. During this time my boss supported me by loaning me money and allowing me to live in his studio rental for a really good price. He continues to support me by paying my salary, and I still live in his studio. Actually, when I think of it there’s probably no one else has done more for me in recent years as he has. Without this job I would be in a tight financial bind as I’m still recovering from my divorce and have very minimal savings. Not to mention I have an 8 year old so this puts an extra strain on the situation as I have to care for him as well.

I never planned to sleep with his daughter. I’ve known her since she was 12 and never had looked at her in a sexual way until recently. One night I ran into her at a local bar. I was there with a group of friends and she was with this hot redhead I’ve near met before. I chatted them up and she told me about some guy that had poured a drink on her. Long story short, I ended up getting in the guy’s face, which made me look like a bit of a hero which definitely scored me points for later. 

After a while I got a little too drunk so I left the bar and drove home. I barely recall texting them to come over but when my memory fully came back they were both at my place. Let’s call them Vivian and Anna. Vivian is my boss’ daughter and Anna is her hot friend. As we were cruising on my patio smoking weed Anna asked me if I thought Vivian was hot. I said, “hell ya,” and asked Anna if she thought Vivian was hot. She said yes. I asked them if they’ve ever kissed before and they hadn’t, so I said, “why not? You should.” So they started kissing and I moved in close and started kissing them both. Then Anna and I started stripping Vivian down until she was naked. She had rad petite body with pierced nipples. Then Vivian asked why Anna wasn’t naked yet, so we started stripping her down. She was gorgeous. A true ginger babe. She had a slender body, long legs and a nice ass. The girls started fingering each other and I was getting a hard on as I stripped down to nothing. Then Anna went down on Vivian and started eating her out. I got behind Anna and started licking her pussy and ass. Then I got up and started fucking her doggystyle. She was super tight. A few minutes later we all went inside and to my bed. 

The girls were going at it with each other so I started filming with my iPhone. Vivian saw me doing it and got up and grabbed my phone. I thought she was going to be mad but she threw me down on top of Anna and started taking photos of us making out. Then she jumped on us both and we all started kissing again. I laid back and pulled Vivian on top of my and she started riding me. Then Anna jumped on my face and I ate her pussy while she and Vivian kissed on top of me.

After quite a while I started going soft. I didn’t climax that night. Sometimes this happens when I drink too much.. I just can’t cum so I just fuck until I get too tired.  The girls got off of me and continued making out. I grabbed my phone and took a few photos. After we were done we smoked again and Anna started feeling sick so Vivian drove her home. I sent Viv a text saying, “I fucking love you,” then I passed out. 

I woke up the next morning with Vivian next to me. It was a nice surprise. I also had morning wood, so we fucked again. This time I came. But now I was beginning to worry about the consequences. I mentioned I rent my boss’ studio which is located below where he lives. Luckily he was on vacation but still, I was tripping and kept thinking the neighbors might see her and say something. I felt like I had to get her out of my place quick.

She left and later that day I found Anna on instagram and messaged her. She was a little shocked at what happened and told me she has a boyfriend. I told her not to feel bad and that it’s ok to live a little. She asked about the pics that were taken and wanted to see so I sent her a few. She said, “that’s hot.” I know she had fun.

I told a couple close friends about this as well as my therapist. Not in as much detail of course. I started thinking that even if my boss found out that he may not be too mad. I mean at first maybe, but he’s actually pretty open minded and not super protective of his daughter. And this being a “heat of the moment” situation and not premeditated, I think he may understand. Plus he know his daughter is a bit of a “bad girl.”

But.. since this night Vivian and I have hung out a couple times. She also had a boyfriend at the time, but they broke up soon after and we started hanging out again. One night she snuck over and we had sex twice and once again the next morning…this time with her dad upstairs. So in the end I feel a bit guilty for “returning to the scene of the crime” so to speak. And she and I will probably hang out again, which I’m conflicted about. I should probably cut it off. But there’s just something about her being off limits that thrills me.

…Thoughts? 

Source: reddit.com/r/gonewildstories/comments/6yjxbj/i_had_sex_with_my_boss_daughter_and_her_friend_mff

41 comments

  3. Is cool what happened. She’s of legal age to make own choices.

    But as said is your bosses daughter and has the chance of blowing up in your face.

    Time will tell if your a champ or a chump……

  4. if this story is real you’re the biggest idiot I’ve ever seen on this website. jesus christ

  5. Dude how old are you again? You damn well know you could easily lose your job and the place he’s renting out to you. I sure hope that pussy is worth it.

  6. Told a couple of friends…. Amateur! Now it’s out in the open. Never kiss and tell!

  9. See you on r/tifu. tl;dr had a threesome with boss’ daughter and her friend. Her father and I don’t talk anymore. Worth it

  11. Bunch of bitter people hating on this guy. I say keep doing even crazier shit! Get some coke and try and bang her and more of her friends.

  36. I’ve got sympathy as I’ve done stupid things when in the moment myself but as others have said, don’t shit where you eat. Could it end well? Sure. Could it end so horribly that it fucks up your life. Yep. Is the risk of the later worth getting laid? In my book, no, no it isn’t. There are plenty of good lays out there your boss won’t get pissed at you for and throwing you out of your home for hooking up with.

  39. your the man! nice story I would have done the same..i got one like it, but too lazy to write it out on here..i will someday

  40. Goddamn, dude, you sound **cartoonishly** sleazy. I’m imagining Pepe LePew wearing really fitted Ed Hardy jeans and some kind of MMA t-shirt.

    ****

    > I’m 38, a single dad and work as a professional photographer.

    Everything has to be considered in context, right? If this were a biography of some kind, nobody would bat an eye. If this were a single’s ad or Tinder profile, everyone would just politely pass it over. On a subreddit that is – by definition – dedicated to tales of penetration, it’s … surprisingly off-putting.

    Also, can we do a little math here? The girls are 21 and 19, yes? So you’re roughly 1.8x older than the first one. You’re exactly 2x older than the second one.

    > Couple years ago I went through a gnarly divorce and had to sell my house and pay $25,000 cash on lawyers.

    I believe this part immediately.

    > During this time my boss supported me by loaning me money and allowing me to live in his studio rental for a really good price. He continues to support me by paying my salary, and I am still live in his studio.

    I know this isn’t the point you’re driving at, but I feel like all of these things could have been consolidated into one payment, right? Lots of leftover +’s and -‘s on the ol’ balance sheet.

    > I never planned to sleep with his daughter.

    For what it’s worth (drunk driving, banging your bosses daughter and then telling lots of people about it, etc.), planning doesn’t seem like your strong suit.

    > Long story short, I ended up getting in the guy’s face, which made me look like a bit of a hero which definitely scored me points for later.

    “Bit of a hero?” Bro, you *are* Captain America.

    (I will grant you, these are the sorts of dumb-dick shenanigans that might impress a 21 year – particularly if she’s really into horoscopes, or not – you know – the strongest reader.)

    > After a while I got a little too drunk so I left the bar and drove home.

    I nod my head, as if having expected this. *”Drunk driving, of course. Please, continue,”* the placid expression on my face seems to say.

    > I barely recall texting them to come over but when my memory fully came back they were both at my place.

    Time-jump!

    > As we were cruising on my patio

    Is your patio… mobile? Because if so, I take all of this back.

    > So they started kissing and I moved in close and started kissing them both. Then Anna and I started stripping Vivian down until she was naked. She had rad petite body with pierced nipples.

    This accelerated quickly, I feel. Also, “rad” made me laugh out loud.

    > Then Vivian asked why Anna wasn’t naked yet

    Relevant question.

    > A few minutes later we all went inside and to my bed.

    Holy shit, *all of this was on your patio*. Did that surprise anyone else??

    > I sent Viv a text saying, “I fucking love you,” then I passed out.

    I lost it when I read this. What in the fuck?! This sentence marks the point exact where I lost self-control and just started sharing this with all my friends, so we could laugh together.

    > I woke up the next morning with Vivian next to me. It was a nice surprise. I also had morning wood, so we fucked again. This time I came.

    I feel like this was written by a horny, teenage Cormac McCarthy.

    > She was a little shocked at what happened

    I don’t see why, it was all so matter of fact. “Is she hot?” “hell ya.” Patio fucking. I mean, 1+1 still equals 2, right?

    > I told her not to feel bad and that it’s ok to live a little.

    Sage advice from a man nearing his 40’s.

    > I told a couple close friends about this as well as my therapist.

    I know therapy is considered a process and all, but… think about switching it up. This one may not be getting it done.

    Also, are reddit posts considered discoverable evidence?? Hi, jury!

    > I started thinking that even if my boss found out that he may not be too mad.

    Oh, I’m sure not. He’ll probably laugh it off and reduce your rent some more.

    > Thoughts?

    A wise, middle-aged man once said “Don’t feel bad. It’s ok to live a little.” I like to think that applies here.

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