Of course, it was my first time having sex with a trans woman not my first time fucking an asshole. My ex-girlfriend loved anal and I know lubrication...is needed from experience. Also, I know the fact that I'm raw dogging a total stranger up the ass is a questionable decision. Came out of that unharmed so bam. Once I felt her asshole relaxing I went porno status on that ass. She had to keep telling me to keep it down cause we didn't want to wake grandma up. Had her on the couch, doggy style,. She said, “Don’t get puzzled. The loser will perform the task the winner asks him to do. It can be any task. Do you agree, just try.If still you are bored, we quit.” I agreed, we drew the curtains and cards were shuffled and distributed. Moreover, as expected, I lost. She smiled and got on her knees, “Come here, young man give me a kiss.” I froze hearing this. I bent forward to kiss her cheeks, she turned at the last second, and I ended up kissing her lips. A current ran through my spine. I was. More

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