Mistress Roiphe

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Day in the life of a hottie keyholder.
1k words
4.04
8.8k
5

Part 15 of the 24 part series

Updated 06/07/2023
Created 01/18/2016
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Roiphe smiled at Sport, her pretty little face beaming in the mass of dark curls. Roiphe's little fingers wandered up and down Sport's big cock as he tried to shift.

But he was tied spread eagled on the bed, and stark naked. His cock felt so good, now that it wasn't in the tube anymore.

Roiphe tittered, but she tried to look sympathetic. Sport was one of her favorite clients. As a key holder, and professional Teaser, she mostly dealt with old men.

Sad little balding banker-types. And one would come in, his little pee-pee so happy to be unlocked after a fortnight of suffering, waving around under a pot belly.

If not for the munificent hourly rate, Roiphe would certainly demur her duties there. It wasn't complicated. Give the man a long, teasing hand job and lock him up again, watching him cry in desperation.

Every six weeks or so, you let them jack off in absolute gratitude!

And most of her clients were sad little Beta males.

One guy, D.J., was a hapless, balding technocrat, who struck out at company softball and had pretty girls stroke his arm before going off with their boyfriends.

D.J. felt he was so obsessed with whacking off and Internet porn that it was affecting his work, but damn it, he was so lonely. His ex wouldn't let him see the kids anymore, that kind of thing.

Now he had a purpose. Roiphe required that D.J. come home at night, turn off the TV and the computer, and spend the evening, while locked in his tube, writing lines.

Five hundred lines a night after work, and two thousand on Saturdays and Sundays. D.J. sent them to Roiphe by messenger, and she'd record them.

If he hadn't quite finished his quota, about eleven thousand lines for the fortnight, when D. J. came to see Roiphe, he'd stay locked.

Not even a tease, and, while protesting, she'd tie him down and pee in his mouth and use her cane on his squirming body until it was very marked up.

If he did make the "numbers" it was a very different visit. Roiphe would greet D.J. with kisses and hugs, leaving her lipstick marks all over his face as she cuddled in his lap.

Roiphe would unlock D.J. while he was tied down, and she'd tickle his penis and Oooh, what a nice big orgasm he got to have!

On his birthday, Roiphe had ridden E.J.'s cock, pulling and pushing her tight twat up and down on him, and it was an experience!

Roiphe was ninety-nine pounds of hot surfer girl, and what a nice experience for a man who routinely was rejected by the girls at the office!

Another client, Crittenden, normally a high profile architect, liked dressing up like a girl. Crit was one ugly transvestite, but Roiphe had decreed that at least twice a week Crit had to become "Cathleen" and get all rigged up in a party dress and full makeup, and to get a little action.

If Cathleen couldn't convince the drunken pickup to take a shot with Cathleen sucking his dick with the cell phone, or a shot of his dick going into Cathleen's ass, then there was no proof.

And Cathy had sucked and been butt-slammed for nothing.

But, if Cathleen got the proof, and sent the shots to Roiphe, then every two weeks, with four humiliating hookups under his belt..

Roiphe would allow Cathleen/Crittenden to strip to garter belt and stockings, and rub his penis against a piece of furniture, like a dog, for a nice hot mess,.

This before being ordered to lick it up, getting re-locked and going home.

Nelson enjoyed laying naked and bound under a seatless chair after his two weeks of orgasm free living.

Roiphe would plop her pretty buns in the hole in the seat, shifting slightly so her vaj was just over Nelson's sweaty face.

Nelson had to lick Roiphe to three orgasms before she'd give him permission to rub his cock (as he was still bound under the chair) against one of the chair legs to cum.

And if Roiphe didn't cum--and she didn't orgasm easily--Nelson had to just get locked up and go home with no cumming himself.

But Sport was different. He was a regular guy, and he'd probably had his share of bedroom antics. Roiphe worried a bit that she might fall in love with him.

Sport had brought his own chastity device, and she'd locked him in. He'd told Roiphe that he'd never been in one for more than eight days at a time, and was a little scared.

"We'll take it slow" she'd said, rubbing his arm with a fuchsia nail.

First there had been weekly visits, and a weekly unlocking and orgasm, and then Roiphe had gently turned it into two weeks.

This meant, of course that he would be paying her less, but she was so hot for him that she was a little tempted to give Sport a discount.

"It was real hard on Tuesday night" Sport said now as he lay there, his arms spread out. Roiphe was slightly tempted to tickle him under his gorgeous armpits.

"Really, honey?" Roiphe asked, chuckling. "Did some girl come on to you or something?"

"Yeah, we were throwing darts and this barmaid, she and I hooked up last year in my car, you know, and she was excited that our team was winning against the visitors from the Hornet's Nest pub..."

Roiphe stroked Sport's dick, denied these fifteen days.

"And I threw the winning dart, and the girl--Monique her name is--she had me sit down and she began squirming all over me, and my dick felt like it might pop the tube, you know?"

"And you couldn't even go home and jerk off, right?" Roiphe tried to look sympathetic, but she was thrilled.

Roiphe traced a finger up and around Sport's chest and tickled and lightly pinched his nipples.

"I actually started thinking of you when I was at home, Roiphe." Sport said, looking up at her earnestly.

Roiphe tried to look a little bored, but she unbuttoned her blouse and threw it off, knowing her rack was resplendent in the little beige brassiere.

"I know I said I want to do a whole month without cumming one day, but I don't know if I can go through with it." Sport looked up at Roiphe imploringly.

Roiphe played with Sport's stiff penis and chuckled to herself. She couldn't believe she was paid to do this.

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zona_loserzona_loserover 4 years ago
loved it

i love all your stories especially the ones that have a crossdresser. lol. poor cathleen, has to rub one off on a table leg and lick it up. i simply must try that.

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