Dirty sex with my boss and how he made me cum from anal [f]

I've posted on here before about the complicated relationship I have with my boss, I'll call him Luke. Essentially, I have been fucking him since November, shortly after I started my employment at my work. We're into some weird, kinky shit. My boss is 8 years older than me (he is 30 and I'm 22) and very handsome. Not only is he my fuck buddy, he's also one of my best friends. We see other people and don't consider what we do a romantic relationship. We are very good friends who happen to be extremely sexually compatible.

Onto the dirty story.

Last night, we had been texting each other. He was at a bar after work and I was at home having a couple drinks myself. A couple hours passed and he asked if I wanted to come over to watch Netflix, but I knew that meant, "Hey, I'm home from the bar now, there weren't any hot chicks. Come over and let me fuck your brains out." And, because I'm a little bit of a whore, I did. He was eating when I got there but shortly after we stripped down to our underwear and snuggled up in bed together (we do this often, even if we don't fool around. Best cuddle bud ever). He laughed and said, "Come over to watch Netflix… hahaha" I looked at him and said, "Yeah, I read into that one… definitely you just ringing your little whore bell." We laughed and were pretty drunk and tired. He said, "Do you want to masturbate together?" And, of course, I said yes.

He was laying sideways facing me and I was on my back with one leg draped over him, the other spread wide. We pushed our underwear out of our way and we began stroking our respective selves. We took our time.

Then he asked if it would be better with porn. I said absolutely. I had never watched porn with someone before, but it was so erotic. He put on this really goofy Gilligan's Island themed porn. At first I couldn't stop laughing because it was just such a weird porn to choose, but eventually the Gilligan's Island thing was dropped and they were just fucking (two girls and a guy). We touched more. He held one of my legs up with his arm while he watched me touch myself and he kept jacking off. He whispered in my ear if I'd get off better if I sucked his dick (because I do very much get turned on my sucking cock). I nodded and I went down to work my magic. I kept touching myself while I blew him and worked him with my hands. I do this twisting technique that he absolutely adores. He says it feels so good that sometimes it's almost too much, but not quite. After going on for a couple minutes, I came on my hand. Like a leg shaking, biting, grabbing the sheets type of orgasm. This turned him on and he grabbed the back of my head and started fucking me in the mouth. I hadn't finished cumming so I was moaning on his dick, which I think felt good for him.

But he wasn't done. He's into foot jobs a bit, and I had never given one. So, he suggested we try it, and that it was the perfect night for it. He put me on my back and had me spread my legs. He ordered me to touch myself as he poured lube on his dick and my feet. Then he grabbed my feet and started fucking them. It was wayyyyy hotter than I thought it was going to be. He just used my body for his own pleasure and I find that so fucking hot (I like being used and abused).

Then he proposed I ass ride his dick while I finger myself. So I got on top of him and spread my legs facing him. I sunk my ass down on his cock (I loooove anal) and rode him while I rubbed my clit and fingered myself. I'm a bit of a squirter, and he told me to cum and squirt on him; however, I didn't get the opportunity to. I was ass riding him so hard and his hips moved in just the right way that I came. HARD. From just the anal. It was like nothing I had felt before. My eyes rolled back and I was convulsing. I fell backward onto the bed, my head and shoulders hanging off the end as I came back from this crazy orgasm.

My legs were still spread to him but my ass was resting just in between his legs on his bed now. He took my feet, again, and fucked them while I watched the porn and finger fucked my pussy .

Then he demanded I suck his dick some more. I did, and he moaned and called me a dirty little bitch for going ass to foot to mouth, but that it was so fucking hot to him. I worked him with my mouth, going faster and deeper. He rolled me onto my side and twisted my body so my head was turned to the right, my tits (hanging out of my little bralette) were facing left, and my ass was facing up and slightly to the right. He put his dick in my mouth and told me to finger my ass. He fucked my face and watched me finger my asshole, first with one finger and then with two. He was about to cum. He went down to my ass and spread my cheeks some more, lightly stroking my pussy with one finger a couple times, I think to see how wet I was (very), while he jacked off. Then I added another finger for a total of three. I saw him go faster, his stare not breaking from my ass. He moaned more and I moaned more. It felt fucking good. Then, he came all over my ass and my pussy. He spread his cum around on me a little and I dipped my finger in and tasted it before I moaned and swallowed.

It was one of the dirtier nights we have had together, and it was one of the best.

Source: reddit.com/r/gonewildstories/comments/37c20g/dirty_sex_with_my_boss_and_how_he_made_me_cum

17 comments

  1. Aflac! Aflac! Ohhhh Aaaaafffffflllaaaaac! Oh wait that’s a duck.

  2. Between your story and your pics, I’m very worked up over here ;)

  3. Ass-to-foot-to-mouth — I think you invented a new genre. Trademark that and sell the rights to Brazzers :)

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