Last month I (33M) traveled to North Carolina for work and while I was there an old colleague of mine (34F) and I met for dinner at the restaurant below my hotel, for the sake of the story we will call her Jessie. Jessie's been a work friend for a long time but only ever just a work friend. She has huge breasts and a gorgeous smile. While we were catching up the wine started flowing and Jessie was looking better and better every minute. She explained to me that her and her husband are living in separate rooms and starting to go through the steps of a separation and that she hasn't been fucked in over a year. I told her I would be happy to help her out and we got the tab. We were teasing each other and making out before we even got to the elevator. Once we got to my room I pulled her hair and threw her against my bed and lifted her dress to start eating her out from behind. Jessie moaned so loud and was so wet then demanded that I lick her ass and of course I did. She then rolled over onto her back and her tits were out of her dress so I started sucking and playing with them to drive her crazy. I went to slide my dick into her pussy and Jessie stopped me and asked if I had condoms because she wasn't on birth control. I didn't have condoms but she said to fuck her anyway but I was not allowed to cum in her pussy. I stroked in and out of her while we made out and I pulled her hair. She seemed to be into the rougher stuff. The next thing caught me by surprise as Jessie pushed me back and told me she wants my cum in her asshole. She then rolled over and put her ass in the air. I immediately started eating and fingering her ass then slowly pushed my throbbing hard dick into her. Her ass was beyond tight and I couldn't hold my load very long. I started thrusting harder and told her I was going to cum. She screamed yes and I pumped my load in her ass as deep as I could. That was only round one of the night.