(This was originally filmed as a custom video) Your step-mother gets home from work and comes into your bedroom, chatting to you about her day at the hospital. She tells you about how she had to perform a sexual health check on a man and it reminded her that it's been quite a while since she last gave you a check over! She suggests that as you've got time before dinner, how about you do one together now? She begins quizzing you about your masturbation habits, getting you to tell her how often you masturbate, how much cum you produce, how long you stroke for etc. You're a little embarrassed ...

(This was originally filmed as a custom video) Your step-mother gets home from work and comes into your bedroom, chatting to you about her day at the hospital. She tells you about how she had to perform a sexual health check on a man and it reminded her that it's been quite a while since she last gave you a check over! She suggests that as you've got time before dinner, how about you do one together now? She begins quizzing you about your masturbation habits, getting you to tell her how often you masturbate, how much cum you produce, how long you stroke for etc. You're a little embarrassed but your step-mother is very sweet and caring, and insists you shouldn't feel awkward. She asks if you've experimented with anal play at all yet, and when you admit you don't know much about it, she offers to give you a walk through! She teaches you how to douche your ass, then gets you to start fingering your own asshole, before offering to do it to herself as well so you feel more comfortable. She walks you through using different butt plugs, showing you them in her own asshole as she gets you to put them into yourself as well, then says she wants you to start doing a stretching routine a few times a week, and gives you a large butt plug to work up to. She tells you to leave your plug in for the last part of the examination, as it will make your orgasm feel nicer, then she gives you some JOI, making you stroke yourself slower and then faster for her, and getting you to edge and hold off your orgasm to test your stamina. Then when she can see that you're dying to cum, she instructs you to orgasm for her, watching closely so she can see how much cum you produce!