He started running his hands over my ass, squeezing here and there. Then he spread my cheeks, as I felt the air against my ass hole. “Please, don’t fuck in my ass, I have never done anal,” I said. “Never done anal huh, well there always a first time isn't there.” I then felt his thumb pressing against my anus. “MMM you are tight. I think I will fuck it, never broke a girl’s anal cherry before.” I then felt his thumb press harder, as it slowly started to slide. I tried clenching my ass, but he just pushed harder, making it hurt. Then his thumb pushed down and went past his knuckle as I cried out in pain. “Ohhh fuck, you are so hot slut.” He started wiggling his thumb around, which brought strange sensation through my body. I could actually feel my pussy getting wet. He then pulled his thumb out, which left my anus opened a little. I gasped out, as it felt I might shit. I clenched down. I then felt his finger touching my pussy lips, as he explored my bare mound. “Shit. “I got so excited about wearing my sexy new trousers that I forgot to put any underwear on.” For most women, this would be no big deal, but Annie often wore a bra to bed. We were in unchartered sexual territory. We finished our dinner, skipped dessert and rushed back to the hotel. I could not believe it when Annie began pulling her jumper off in the hallway before we reached our room. Once I unlocked the door, she knelt before me, unzipped my trousers and began slurping on my cock, dressed only in her leather trousers and high heels. She finally stopped, removed the trousers, pushed me on my back, planted her pussy firmly on my mouth and commanded: “Eat me!” We sucked and licked each other to initial orgasms, and then fucked in every position we knew (which was not very many) and then discovered a few more. We overslept the next morning and missed our flight, which just fine with us. We went out for lunch (she wore the trousers again) and managed to begin making love early, so we.
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