Vanessa Cox
16 Followers
I told my boyfriend that I used to fuck my boss for money. It was back when I was with my ex-boyfriend. My ex treated me like shit and I was looking for a way out and needed money.

My boss saw his opportunity and offered me $200 to fuck him. I probably fucked him 70 times and he never lasted over 5 minutes, so it wasn't really that big of deal.

While I am telling all of this to my boyfriend, I start to get the feeling that he was turned on by it and possibly wanted me to do it again. I mean, I would TOTALLY do it again! My boss's cock is small but I honestly LOVE how his cum tastes.

I even hinted to my boyfriend saying how I LOVE to be told what to do hoping he would tell me to do it. Just thinking about it makes me want my boss's cock in my mouth!

I think I will try to bring it up when I'm at work and see where it goes.
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A little of my history - part 2

I fucked around with a lot of guys for the next couple of years. When I was 18, this 29 year old guy, came into a store I was working at and asked if I wanted to hang out when I got off work. I had a boyfriend at the time but he worked late and was a dickhead anyway, so I agreed to meet up with the 29 year old. We went to his apartment, had a few drinks and eventually started making out on his couch. I got on the floor and started to suck his dick. After a few minutes, he stands up and tells me to bend over the front of the couch. I love being fucked from behind and being told what to do so I willingly did it.

He yanked on my pants barely pulling them down. I remember thinking about how my pussy wasn't even exposed and wondering what he was trying to do. So, I reach back to pull my pants down further and he jams his dick all the way into my ass. I have never had anything in my ass before and he did not show any mercy. He literally pounded my ass for almost a half hour. He was telling me what a "good little slut" I was, and that now I am an "anal whore." He came inside me three times and would just keep fucking like crazy without stopping. I was in so much pain but that's a perfect example of me not being able to say no. By the time he was done I was pretty much in tears.

After he blew his third load of cum in my ass he pulled his dick out and walked down the hall. I was laying there bent over the couch not knowing what to do. I was thinking...Was he done? Should I get dressed? I was afraid to get up because I didn't know if he wanted to fuck my ass some more, plus I was worried about the three loads of cum that was going to start leaking out of my ass if I got up.

He comes back down the hall says, "Quit crying you slut." He got behind me like he was going to fuck my ass some more but instead, I feel him pulling my pants back up. He casually says that I have to leave and that we should hang out again.

Thole whole time I was driving home there was cum leaking out of my asshole. My ass was so stretched out that I really could not control it. I remember thinking how we barely hung out for two hours and he was fucking me in the ass for the last half hour. I felt extremely slutty and used, but part of me really liked it.

The next day at work, my boss at the time, who is 12 years older than me, says he can tell something is wrong with me and asks what the problem is. I end up telling him everything that happened. I told him how I have never done anal and how the guy just did it while calling me a slut. At one point, I see my boss "adjust" his dick through his pants. I could tell that me telling him about what happened the previous night was arousing him. He is married, 12 years older than me and has kids so I would never fool around with him but it didn't stop me from embellishing a little on the story. I did repeat several times that I just can't say no lol!

For example, I left out the part about crying and added how much being called a slut turned me on. I could tell he was really fighting to hide his hard on. He tried to pull his shirt over it, then stood up and tucked it in the waistband of his pants. I left it alone after that but it was funny to see him get all uncomfortable like that hahaha!

This is where things get even more interesting. Three or fours days later, my boss asks me to stay late for a short meeting after work. It wasn't uncommon so I didn't think anything of it.

Skipping ahead to the meeting, it was weird because we were the only two there. He sat there in his desk chair in silence almost like he didn't know what to say. I asked if everything was ok because his behavior was worrying me like I was about to lose my job lol!

He says, "So...the other day when we were talking..." He was clearly having a really hard time trying to say what he wanted to say so I kind of tried to help him spit it out.

I say, "...talking about...?" He says, "You know, what happened to you the other night after work." I feel like he wants me to talk about it and turn him on again, so I say, "You mean when that guy fucked me in the ass?"

My boss didn't say yes, he almost seemed afraid to respond. There was an awkward silence and I jokingly say, "My ass is fine if you are trying to tell me you want to fuck it. You know I can't say no."

I will never forget this. He opened his desk drawer and threw $200 down and said, "I will pay."

I thought to myself..."I would fuck you for free, but if you want to pay...GREAT!"
I didn't hesitate. I take my clothes off and bend over his desk dreading the ass pounding that I am about to take, although part of me wanted it lol!

He rubs my ass cheeks a little, then to my surprise, slides his dick into my pussy. I was relieved but still waiting for a cock to be shoved into my ass at any time.

For the record, his cock was small but I loved the way he fucked me. He really liked to fuck hard and pound against me. Two minutes later, he pulls out and cums on my ass. We continued to pay me for sex after work roughly 70 times over the next several months, so you can add whore to my resume as well lol! He never did fuck me in the ass and he never lasted more than 5 minutes, so it was easy money and my pleasure.

After that, I had even less of a problem cheating on my boyfriend at the time. There were days where I would fuck my boyfriend in the morning, then another guy on lunch break, my boss after work, then my boyfriend again when I got home. He never had a clue.
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