My Boss Didn't Know How to Ask

She told me she wanted me to fuck her pussy for a bit before trying anything else. She told me that she wanted to stay my boss and not my baby's mother and tossed a condom to me. I slid it on and then slid inside of her. Her pussy was quite wet I could tell even with the condom on. I slid in easily but I tried to take my time so that I didn't get to the finish line before I had really started to enjoy the race. I realized quite quickly that she loved it when I was all of the way inside, so I stayed up inside quite deeply and then pushed a little more over and over. She moaned and groaned and writhed and it was perfect for me because it felt really great but there was not nearly enough friction to drive me over the edge.

After a good amount of this she told me it was time, and to pull out, lube up and to fuck her ass. Just hearing her say those words made me shudder in excitement. I applied a lot of lube to myself and watched as she rubbed some into herself. I told her to try getting on top just like how I had done because it was really easy to control. She agreed and we flipped around so that I was below her. She lowered down and down and I watched her close her eyes at the moment I felt my cock pressing into her. She pulsed with very small strokes and realized somewhat belatedly that she was working the head of my cock inside. To me it didn't feel like I was getting anyway but suddenly I felt the pressure drop off significantly on the head of my cock and I realized that she had got me inside.

She stayed like that with very feint motions and then she started to pick up the pace. She was a very loud lover anyway but the sounds she made while I was stretching her previously untouched ass were almost alarming. Her tone was much deeper, more guttural and so sexy. After a few moments she got up off of me and walked over to the couch. Bending over it, exposing those sexy long legs in those hot thigh highs and the ass that belonged to a 20-year old and not a 40-year old, she invited me to come and fuck her.

I practically jumped off the bed and got in behind her. I took a grip of my cock and started to guide it towards her opening in the rear. She reached back and spread herself open giving me a good view of where to go. When she felt my cock getting close she surprised me by pulling off the condom and telling me I wasn't going to be making babies were I was going. I couldn't believe what I was about to do, the dragon I was about to slay, and had she not the words she did, I might not have believed she really wanted what I was planning on giving her. She told me she needed me to fuck her ass as hard and as deep as I wanted, and let me tell you by the time I was inside and we were both comfortable I did exactly that. I fucked my boss in her ass as hard as I had ever gone in any person.

It was my third time having anal sex in my life but I'd never been given permission to do what I did. The sound of my abdomen slapping into her firm curvy ass shocked me, but the grunts and moans that I made my boss utter blew me away. I grabbed a couch pillow and covered her mouth with it while my cock used every one of its inches to completely stretch and fill her. By the time I knew I was about to cum I barely was able to mutter the words and hear her tell me to just cum in her ass before my balls released their thick white fluid and I flooded the inside of my boss' ass. I pushed deeply into her with slowing strokes and made sure every drop was deposited into her before pulling back out. She turned and looked at me with a sexy almost confused gaze. I had literally just fucked my boss' brains out and we both got off on it.

She kissed me deeply after that, her tongue was wild and aggressive and I loved it. By the time we were done kissing she told me she had to go drop her daughter off at her ex-husband's house from daycare but that I had just given her the best sex of her life. Of course the feeling was completely mutual and I told her that she was by far the sexiest woman I'd ever been with. I started to get my clothes on while she started to pick up the room. She pulled the panties out of the envelope and slid them up her body thanking me for returning them to her. Then she told me that she had the room booked for the full weekend and told me to give her a call if I wanted to come back for a little more fun. I did, and decided that I wouldn't be telling my co-workers about the panties in the envelope after all. I noticed my boss was a lot nicer to me after that day for some reason...