Evening With My Boss

I got a new job and I made my Boss a promise to go see him that night, so I did as I promised. My boyfriend didn't mind, he actually encouraged it. My outfit for the evening was a black skirt, fishnets and a green sweater. Wore dark eyeliner and makeup with red lipstick.

He text me his address and I drive out there. At red lights, thinking about what will happen. I know I'm there for sex, but I wonder how it will be. Can he get me off or will I just be getting him off? Will me being loose be an issue? He hasn't seen my holes yet, just my butt cheeks.

I pull up to his place and he lets me in his house, glass of wine ready for me, lights are dim and he's changed into swimming shorts and t shirt. I thank him, put my stuff down and take the wine. He shows me his place, it's not a bad place, just not really decorated. Anyway, by the time he shows me his room, I make the comment that 'this must be where all the action takes place'. I felt like a dork saying that but he laughed. When we get outside, he takes off his shirt to get in the hot tub. He tells me to join him but I don't have a swimsuit (well i don't own one). Eventually after some horrible pick up lines and compliments, I undress and get in tub with him.

He asks me if I know why I'm there and I say it's for sex. He kinda laughs and says I must have done this type of thing before. I smile and agree. He leans into me for a kiss and I kiss back. Then he grabs my hand, placing it on his dick telling me to jerk him while we kiss. I mutter 'yes sir' and lightly jerk him. After some kissing and touching he moves me to sit on his lap where he rubs his dick around my asshole. I ask him to give me anal. He says I'm a good slut and gives me anal in the tub, bouncing me up and down for a long time before he got off. I didn't get off :(

I move off of him and play with his penis some more telling him I'm still horny. He tells me to wait there. He comes back with a towel for me after some time and I dry off, then we go in his bedroom. He ask me since I said 'sir' earlier if I was a sub before and I told him it's what I love doing and I like it rough. I lay on my back on his bed and let him start playing with my pussy. He licks me for a little bit and then (what I thought were his fingers) starts using a dildo on me. He starts slow and then fast. When it starts making noises going in and out, he starts rubbing my clit. I start thanking him and eventually get off. I tell him I'm cumming and he shoves the dildo in my pussy and rubs my clit until I quit moaning. 

 

He cuddled with me afterwards asking about my sex life and things I've done. I admit to a lot of things but left out some details. Before I leave, he gets on top of me and we have sex one more time while making out.