You, as my step-mom, observe me and my date before we leave for prom. It's my first prom and my first date.

You notice that I seem a little nervous, and tell me that maybe we should do my monthly release a little early.

(To my date) "Oh, he didn't tell you? We have to keep his little penis in a chastity device to keep him from playing with it. You don't know what a chastity device is? He's a chronic masturbator, he was just going at it all the time "fap fap fap". And without permission even! Honey, take off your pants and show her the device. Don't be so shy. ...

You, as my step-mom, observe me and my date before we leave for prom. It's my first prom and my first date.

You notice that I seem a little nervous, and tell me that maybe we should do my monthly release a little early.

(To my date) "Oh, he didn't tell you? We have to keep his little penis in a chastity device to keep him from playing with it. You don't know what a chastity device is? He's a chronic masturbator, he was just going at it all the time "fap fap fap". And without permission even! Honey, take off your pants and show her the device. Don't be so shy. Do it, unless you don't want ANY release this month, young man. There, see how adorable that is. It keeps him from touching his little penis without permission. Also, it makes him uncomfortable when he gets an erection, which makes him so much more obedient. His step-sisters and I tease him often. (show me a little something, breasts, pussy) If he's a good boy, does what step-mommy and his sisters ask, and keeps his grades up, he gets a supervised release once a month. Maybe if we get one of those out of the way right now, he'll be more relaxed."

Remove the device, have me jerk off. The commentary there I'll leave to you.

Have me finish in my hand and ask my date what I should do with the cum.

"Oh, that's a wonderful idea! You heard her, dear. Smear the cum all over the front of your shirt."

Have me put my device back on, leave my pants off, I'm going to prom just like that. No pants. Chastity. Cum smeared all over my shirt. Take a picture of us, and send us on our way.