Yes. Repeatedly.

Author's note: Slight edit to Jane and oldest stepsister ages in this and the prior chapter to avoid implying John's stepmom got married to a stockbroker and had a kid when she was 17.

His mother's favorite tale about her tail.

She told the story at least once a month in his presence, usually when hosting a party of some sort that she had to let him attend for the sake of appearances.
About 3/4ths of the way through these events, when the men of means were too drunk to notice or remember if they did, she would hold court among her "stud farm", sashaying among them to illustrate her tale.

"A few years ago when I was a hot young thing in my 20s (actually 20 years ago when she was 18 instead of 38, but no one called her on it), I was walking home from yoga class (in some renditions she'd demonstrate a pose or two at this point) wearing these hot pink yoga pants, basking in the wolf whistles and catcalls, when suddenly a tremendous crash from my left caused me to jump in surprise (more demonstration...and jiggling...). My tits weren't this big then (sometimes a gentle hefting of said tits was inserted here), but they still bounced around quite a bit, and when I turned around to check what had happened, another loud crunch sounded from behind me. As it turned out, the first noise was a wreck when some hunky construction workers crashed their work truck into a delivery van while mesmerized by my ass, and the second when a stock broker hoping my tits would pop out ran into a taxi."

"Shut down both streets for half a day, the firefighters still talk about it."

"Not as much as my thanks for their efforts of course, I do like a big strong fireman from time to time. (Here she would run a hand down the length of the most recent example of such through his pants.)"

"The construction workers were fun as well, but the stock broker was my first husband, and (or so he thought) father to my beautiful girls...without his help I would never have gotten so (heft tits again) big."

"Now, it's <insert fireman stud's name here>'s turn first tonight, the rest of you may play with anyone you can catch, I know quite a few horny wives are roaming around."
"If you want a chance at this ass (gentle slap of same) though, you'd better save up all the...stamina...you can, because I'll be staying up late to drain whoever can handle it dry."

Needless to say, few of her chosen would stray after such a display, and John rarely got any sleep those nights.
Unless he masturbated himself into unconsciousness, of course. But it took extra effort on those days.

With a gentle thud, John's erect dick ran into the side table before he did, giving him enough warning to avoid damaging himself or anything on the table, but sadly jolting him out of a fantasy where he had the equipment and sexual stamina to fuck his nympho stepmother into unconsciousness.

Jane giggled quietly at his expense, before pushing him none to gently towards the kitchen.
His stepmother and step-siblings never ate in the kitchen, that was for servants. But they filmed him eating there. It was about 65 degrees in the kitchen, his stepmother said it saved money on refrigeration in the winter, but he suspected it was just to make him as uncomfortable as she possibly could.

"Sit down and eat, you pervert (she'd noticed his erection, and was unimpressed), before the food gets cold. Barbi, make sure you film until he's done, then come to yoga practice, Robert is our trainer today and you DON'T want to miss a minute of his sessions."