Tessa’s boy friend wanted anal sex. Tessa had never done it before and was real uncomfortable with the idea so who else to ask, Uncle Jack. Tessa, dressed in her usual slinky, sexy outfit came to Uncle Jack and told him about her dilemma. Uncle Jack was more than happy to help her out, practice, practice, practice, you can’t have too much practice. Uncle Jack wanted Tessa’s first anal to be a good experience so he went real slow and easy. Jack needed to get ready so Tessa sucked on his cock for a little while then, when he was good and hard she rode his dick, Tessa loves to fuck ...

Tessa’s boy friend wanted anal sex. Tessa had never done it before and was real uncomfortable with the idea so who else to ask, Uncle Jack. Tessa, dressed in her usual slinky, sexy outfit came to Uncle Jack and told him about her dilemma. Uncle Jack was more than happy to help her out, practice, practice, practice, you can’t have too much practice. Uncle Jack wanted Tessa’s first anal to be a good experience so he went real slow and easy. Jack needed to get ready so Tessa sucked on his cock for a little while then, when he was good and hard she rode his dick, Tessa loves to fuck so having Jack’s dick in her pussy was a great ice breaker. Jack suggested they do some doggystyle thinking that would be an easy transition to Tessa’s first anal. Oh, that pussy is so good but Jack had to keep in mind his job was Tessa’s butt. When Tessa was nice and comfortable with her doggystyle, Jack put a bunch of lube on his dick and her butt then gently probed her butt hole with his finger. Tessa didn’t pull back so she was waiting for the experience. Jack pushed his finger in her butt very gently, just a little making sure her butt was good and lubed up then Jack pushed his finger in a little farther, gently, pushing in just a little deeper. Jack could feel her butt tightening on his finger, she was getting the feel for it. It was time. Uncle Jack put some more lube on her butt and ever so gently started probing her butt with his dick. I’m going in. Uncle Jack gently pushed but it wouldn’t go in so he massaged her butt hole with his dick, relaxing her, getting her comfortable with the idea and when he felt her relax a little more he slipped it in, just a little at first and as she got more comfortable he pushed a little harder, she was taking it like a champ. That sexy little darlin took it and kept taking it, she’s amazing and then it was time for Uncle Jack to cum. He turned her around and came in her mouth then had her clean up his dick. Her first time ever anal was a tremendous success, bet her boyfriend will be happy.