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Chapter 44
Is it heads or tails?
Carrie’s in charge
“Tails!” says Carrie, squealing with delight. She goes over to the wardrobe and picks through the bags, then comes back with a package. It’s the size of a small shoebox.
“I’d never seen one of these before and would never have known how to use it if Maud hadn’t explained it. As a treat I’m going to let you open it.”
You take the box from Carrie wondering what it can be. It’s been wrapped carefully in black tissue paper which you quickly tear off.
“A fleshlight?” you say. “Aren’t these for lonely single men to cuddle while they watch Pornhub?”
“That’s one use,” says Carrie. “But you are about to find out another way it can be used. Take off your shorts and lie on the bed while I unbox it”
You as you’re told and watch as Carrie opens the packaging, removing a long black cylinder, thicker at one end.
“Just a sec while I give it a rinse,” she says stepping into the bathroom. You hear the tap running, then she’s back through, shaking it to get rid of any excess water. She lies on the bed beside you.
“So it has two ends.” She unscrews the thicker end and uncovers what looks like a clear silicon doughnut. “Cock goes in here. It’s silicon all the way down with bumps and ridges to give extra stimulation.” Then she unscrews the other end. “This controls how much suction is applied. We can see how much suction you like.”
The matter of fact demo is making your cock harder and you’re intrigued about what is going to happen next.
“Now while this may feel like a pussy, it doesn’t get wet like a pussy, so we’re going to need some lube to get you started.”
She takes a bottle of lube from the nightstand and holding the fleshlight up like a glass tips some in.
“That should be enough. Now I’m not going to tie you, but I want you to hold onto the bedstead above your head as if you were tied up.”
You reach up and hold on, doing what you are told.
Carrie turns the fleshlight over and places the silicon doughnut on the end of your cock. Some of lube drips back out and down your cock. She makes a final adjustment.
“Let’s start with no suction and see how that is.”
With that she pushes it down hard and onto your cock until the silicon is touching your midriff.
“Oomph,” you gasp. That was quite a sensation, far more than you were expecting. It’s tight and slippery, and the ridges and bumps massaged your cock head as it slid in.
“That’s good isn’t it?” Carrie smiles at you.
She pulls it back up until just the tip of your cock is left in and then pushes it down again firmly.
You don’t know if it’s the fleshlight or the fact that Carrie is using it on you, but you are very quickly really turned on.
“Now let’s try it with the suction,” she says as she closes the valve on the top of the fleshlight.
This time when she pulls up it feels as though your cum is being sucked right out of your balls.
“Maud said that this would probably be the closest thing to being milked that you would ever experience not on a farm.”
Carrie pushes the fleshlight down again so your cock is once again buried deep inside it.
“That’s the demonstration over. Now on to business. Maud suggested I see whether I could ruin you on my own. She thought it was a key life skill for me to learn.”
With that she begins to stroke the fleshlight up and down steadily.
“We’re going to get all that nasty cum out of you. You know it’s making you too demanding and we don’t need that do we?” she whispers.
Your cock stiffens further at Carrie’s words. She’s right inside your head pulling your levers.
With each stroke she takes the fleshlight right to the tip and then pushes it down as far as it will go. It does feel like you’re being milked and the way Carrie is not showing any emotion or arousal herself feels very kinky.
You can see her watching you closely. You’re breathing harder now and your muscles are beginning to tense. You won’t last much longer. You might really cum you think.
“Is baby close?” Carrie asks. “Just a little more I think.”
She gives it three more sharp pumps up and down then on the third very slowly pulls it all the way off. You’re beyond controlling your orgasm, and feel and watch as your cock mechanically expels your cum. There’s a tiny spurt and then it just dribbles down the shaft.
“Gold star for me,” says Carrie. “Maud will be pleased, she likes a good student.”
You’re still hard and don’t know what’s going to happen next. Last time had finished with a proper orgasm.
“That’s us for now,” says Carrie. “I need to head to work. Get cleaned up, no masturbating and we can toss the coin again at lunchtime. If it’s heads you get to orgasm, if it’s tails it’s another ruin.”
There’s clearly no option to discuss and you nod your head then watch as Carrie peels off the CUMSLUT t-shirt and gets ready for work.
What happens after Carrie heads to work?
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The “Anything” Promise
The girlfriend who’ll do ANYTHING
Your new girlfriend says she’ll do “anything” and she means it
Updated on Jun 17, 2026
by Harst
Created on Oct 7, 2018
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