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Journey Into Chastity Trilogy

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Journey Into Chastity Trilogy by Stanley Jeffries

John is a college student who is a classic under-achiever. He’s falling behind in his studies, letting his body get flabby, and most importantly allowing his relationship with the beautiful Laura to stagnate. Fortunately she isn’t t ready to quit on him and she’s convinced by her housemate, Christine, that John needs some tough love to help him get his life in order. In fact Christine suggests that imprisonment in a male chastity device is exactly the thing that will focus John’s attention while he is away from Laura at college during the week. When presented with an ultimatum by Laura, John reluctantly agrees. Of course, Laura has her needs, and it seems that the gorgeous and totally evil Christine is quite ready to satisfy them which only adds to John’s frustration as he’s forced to witness their nightly love making over a videoconferencing link from his dorm room, with his poor cock almost exploding from its plastic prison. And this is only the start of his Journey. As he struggles to meet Laura and Christine's goals for his life John submits to ever more cruel challenges, but along the way he discovers the joy of bringing pleasure to both of his Mistresses.


“I’m sorry Laura, but I need my hand to,” she cut me off.
“Then do it for fuck’s sake!” she said angrily, then more softly, “quickly John, pleeeease!”
I have this trick. Well I guess it’s pretty well known to a lot of other folks too, but I like to fool myself that it’s mine. It works like a charm on Laura. At some point as I feel her building up to a climax I insert two fingers into her pussy and curl them upwards to put pressure on a particular place on the upper wall of her vagina. I know some people call it the G-spot, and other people claim the G-spot doesn’t exist, but for Laura, when I do it just right, she goes off like a rocket. And this time was a good one. She was already well on the way, and literally the moment I applied gentle upward pressure she arched her back, thrust her hips towards me and grunted.
“Oh shit! Yeeeesssss!” she cried, and shuddered for a few seconds, gasping for breath.
But there’s more. I knew she’d just had a pretty good climax. If I can catch her just right it’s possible to bring her to a second, and even more climaxes almost right away. One time I think I managed five in a row until she begged me to stop. I ignored her stupid instructions about not touching her. I needed to grab the back of her hips and push hard into her with my face to get this to work. She was also grabbing the back of my head and pushing it as hard as she could. It throws me off my game a bit having my head dragged this way and that. Anyway I was determined to do this, and with a lot of quick tongue work I felt the tension in her body peaking again, and…
“Oh God! Fuck yes, that’s it! Ohhhhh!” she was screaming, but quietly.
I had to admit, this was a bit unusual for Laura, she almost never swore. I rather liked the dirty talk. What the heck, I went in for number three. It took a minute or so of work because Laura was getting tired now, and she tried to push me away rather weakly, but sure enough I caught her just right. The third climax wasn’t as strong as the first two, but it seemed more prolonged. Laura groaned and shuddered for about ten seconds and then her body just went limp and fell back into the chair.
My hands we still around her hips and I leaned forward and rested my head on her tummy. I could hear her heart thumping, and some gurgles from her tummy too!
Her hands were relaxed on my head now, stroking and caressing me.
She was out of breath, but managed to gasp, “How do you do that John? You’re a magician, you know that? You really need to show Christine!”
No fucking way, I thought. I will never show that bitch my party tricks. It occurred to me that my prowess in oral sex might be the only reason Laura hadn’t ditched me. I thought about that for a few seconds and I decided that was just fine by me. The longer I could stay around, the more chance I would have of winning back Laura and getting rid of Christine. Laura might be making up some weird new rules in this relationship, but if I just walked away from it I knew I’d never get Laura back.
After a few minutes of resting, Laura stood up in front of me and began to rearrange herself. She slid up her panties and tights and tugged up her boots.
“Ewww,” she said. “I’m soaking down here. Stay exactly where you are, I’ll be back in a sec,”
She sauntered out of the room leaving me kneeling in front of the empty chair. I was totally confused. What could I do to try and win Laura back? Christine had her all week, whereas I got an occasional weekend.
Laura came back into the room and flopped down in the chair. She crossed one long, shapely leg over the other, which left her left boot hovering inches in front of my face. She sat there in silence, idly twisting her ankles. I listened to the soft creak of the leather and stared, and stared.
“You like these boots, don’t you?” she asked softly. She reached forward and tapped the toe of her boot against my cheek. It felt rather humiliating.
“Yes Laura,” I replied, my mouth suddenly dry.
“I mean, you really like them. I’ll bet you think about me wearing them, don’t you?” She began to trace small circles on my left cheek.
“Don’t you?” she pressed, giving my face a tiny push with the boot as punctuation. I sat there passively.
“Yes Laura, I do actually,” I admitted.
There was a pause. She uncrossed her legs and placed one booted leg on each of my shoulders. The creak of leather was loud in each ear now. She squeezed her legs together and twisted my head, and then she resumed her legs crossed pose.
“Do you actually wank off while you’re thinking about me in these boots?” she asked with a mocking tone.
In fact she knew perfectly well that’s what I did. We sometimes had phone sex that ended up with her describing what she was wearing, and often emphasizing the boots. Until now I’d loved those phone calls.
“Yes Laura, you know I do,” I said quietly.
She giggled now. “That’s right! You wank off when we have our sexy phone calls,” she placed an emphasis on the last three words as though in her opinion they were anything but sexy to her.
“That’s so sad, so pathetic, wanking all on your own. Maybe you should wank off right now. After all you’re right here looking at me. It’s got to be a lot better than a phone call.”
“But I wanted to…” I stammered.
“John, you’re the one who says he’s fucking desperate! Well if you’re really that desperate get your dick out and start wanking. Now!” she ordered.
I was already hard as a rock at this point anyway. I kneeled upright and fumbled my jeans open.

Artist Credit

© Jeremiah Deasey – iStock.com

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