Journey Into Chastity, Book Three New Depths of Pain

Chapter Two-3

I clamped my jaw down again and the second glove was pulled on tight. I waited for the next scrape of the gimlet. But it didn’t come.

“All dressed now, sweetie,” she whispered.

I lay on the bed exhausted and sweating. Christine had unlocked my ankles and wrists, took the tape off my elbows, and allowed me to take out the gag. I drank three glasses of water from the tap.

Christine took off her gloves for the moment, and asked me to lay on the bed while she massaged my skin with baby oil. My hands were trembling.

“What a good boy you are!” she said softly. “Did you enjoy that?”

“It was really hard, Mistress, but did I please you?” I asked.

“Yes, you did, John,” she told me. “I really liked that game.”

“Then I’m happy, Mistress,” I mumbled from the depths of the pillow. “If I pleased you then that’s all that matters.”

Christine had me turn onto my back and I heard her take a sharp intake of breath.

“Oh f**k! I really made a mess of you!” she said, sounding concerned. “Laura’s going to be really pissed off at me if you’re all marked up for her next weekend, but I’m hoping these marks will fade in a few days. I filed down the point on that thing, so it’s not needle sharp.”

“Do you think they’re deeper than the heel marks?” I asked. “They normally take about a week to fade completely.”

“Hmmm,” she said. “Not sure. I think I’d better be careful about doing any more! Oh hell! This one looks like it’s bleeding under the skin! Oh, John, you really should have stopped me!”

“I…was sort of enjoying it.”

“The marks are getting worse. It’s like they’re still developing! Oh God, she’s going to kill me!”

I took Christine’s hand and drew her down towards me.

“Hey! I’m the one who f****d up,” I whispered.

She smiled uncertainly and kissed me; and then she snuggled into my arms. I was allowed to touch her bottom, and slide my hands over her stockings. I worshipped her boots for several minutes, but she didn’t use the heels on me this time. I understood why not, she didn’t want to make the marks any worse, but I was disappointed as it was one of my favorite punishments. Finally, I just lay next to her and we kissed.

“I’ve missed you so much, John,” she whispered.

“Me too, I hate that we have to be apart all week,” I answered. “Maybe you could both get jobs here in Loughborough?”

“We’ve actually thought about it,” she sighed, stroking my n*****s gently. “But if we change schools after only one year, that might be OK. But then what do we do when you graduate? We don’t know where you’ll get a job in two years’ time, do we?”

“I see your point,” I said. “So probably best to stick how we are then?”

“Oh poor baby!” Christine said, kissing me gently on the lips. “Are you all lonely in the week? Laura and I have got each other to keep each other warm, and give cuddles, but poor John is all alone.”

As she whispered to me she traced her fingers around my n*****s, and nibbled my ear lobes.

“Can Mistress make it better with a kiss?” she asked softly.

“You already made it better just by being here, Mistress,” I told her.

“I’m going to ask Angie and Louise to make sure you get your cuddles next term, John,” she told me. “And you’ll be with us most of the summer holiday, so you just need to stick it out for another few weeks, sweetie. Laura will be here next weekend to see you. And you know she’s such a softie about unlocking you; I think she wants to give you s*x because then you’ll prefer her to me, but you don’t do you, my love?”

“Of course not, Mistress, you know I love you! I love Laura too, but I’m totally, utterly and madly in love with you!” I told her.

“Hey, it’s OK, don’t get so excited, sweetheart,” she whispered, pinching my n*****s now. I grimaced with the pain from the gimlet marks earlier. “I know you love me. But we haven’t really talked this over with Laura, and I think we need to do that soon – maybe when you come for the summer. We’ll all sit down, have a grown-up chat, but for now you can screw her senseless next weekend, can’t you?”

“If you’ll permit me, Mistress,” I said. She seemed to have forgotten her conditions completely now!

Christine smiled. “Oh? If I’ll permit you? So you’re saying that if I forbid you to make love to Laura next weekend then you won’t?”

I groaned. “Please…please don’t,” I whispered.

“I’m sorry, I thought I asked you a question, slave,” she said firmly.

I took a deep breath. “Of course I’ll obey you, Mistress,” I said.

“Ooh. But you’re not happy about it, are you?” she asked. “That’s not good; that’s really not good. I thought you’d want to make me happy.”

“But, Mistress, Laura will be expecting…”

“She shouldn’t be expecting anything! We agreed you’d be locked up unless you get a First!”

She lifted her head up and looked me in the eyes.

“We did agree that, didn’t we, John?”

I swallowed hard. “Y-yes, Mistress.”

Christine held my gaze for a few seconds until I had to look away.

“Anyway…you’re a very clever boy, so I’m sure you’ll think of something to tell her if she comes on to you. You’ve got all week to think something up, haven’t you?”

“Yes, Mistress, I’m sure I’ll think of something.”

“That’s decided then,” she said brightly. “I’ll make sure I keep both keys to your padlock next weekend. What do you say?”

“Thank you, Mistress,” I said, carefully trying to hide my disappointment.

Christine was still wearing the tight, black leather gloves. She placed the first two fingers of her right hand on my lips. I opened my mouth and she slid the fingers in. I sucked on the soft leather gently, feeling the tension seep out of me.

“Good boy,” she whispered. “You really are well trained now.”

She lay there with me for several minutes. I almost felt sleepy, but I was looking forward to the next punishment with the gimlet. Christine had said she’d unlock me after that. Eventually she slid her fingers out of my mouth and kissed me.

“You’re my good boy, aren’t you?” she whispered.

“Yes, Mistress; thank you, Mistress,” I said sleepily.

“Now, I’m sure you’ll understand that you can’t continue with the gimlet, John,” she told me.

“Wh-what? Why, Mistress?” I asked.

“Your body can’t possibly take another set of scratches like that. Laura would be even more upset with me when she sees you. You really should have used your safe word in the first session.”

“I wanted to please you, Mistress,” I said softly.

“And you did, sweetie, but your skin is a mess.”

I waited to hear what she’d say next.

“So obviously that means you’re not going to come this evening,” she told me.

“But Mistress!” I cried miserably. “You promised!”

“Don’t blame me,” she pointed out. “You’re the one who can’t complete the game.”

“You promised,” I said sullenly.

“And you can stop with that tone right now,” she said firmly. “I was going to unlock you first thing tomorrow and surprise you with a blowjob. I know men seem to want that first thing in the morning. Well you can forget that now; that’s a disgusting attitude you’ve got.”

For some reason I was getting angry now. But I gritted my teeth, and forced out an apology. “Christine, I’m…I’m sorry!” I gasped. “It’s just that I was looking forward to it…”

“I realize that!” she told me. “Remember I was looking forward to it as well! If you’d used your safe word you could be making love to me now! I keep telling you, John, you need to learn!”

“I’m sorry,” I whispered.

“Well that’s a bit more like it,” Christine said patiently. Then she smiled. “Look, why don’t I do a nice, sexy striptease for you? Then I’ll let you make love to me with the strap-on again. I’m quite turned on again looking at those lovely marks on your body. And it would be selfish for you to deprive me of the pleasure I was expecting, wouldn’t it?”

I could feel tears dripping down my cheeks now. I couldn’t believe this. Christine had already ordered me not to make love to Laura next weekend. Now she was making me doubt that I’d be allowed any kind of s****l release with her this weekend! But I loved her so much; I was desperate to please her.

“Of…of course, Mistress,” I told her between the sobbing.

“Good boy,” she told me.

She stood up from the bed and, with her gloved hands, began to caress her breasts, kneading them gently – a look of sheer pleasure on her face.

“Do you know why I’m so turned on, John?” she asked me.

“N=no, Mistress,” I whispered.

She laughed softly. “Because I’ve just ordered you not to have s*x with Laura next weekend, and you’re going to obey me. Every time I push you a bit further I expect you to turn on me and disobey me. But I’ve broken you, haven’t I, John?”

She slid her hands down to her stocking tops and stroked her thighs gently. She looked like she was moving her body to some music in her own head. Gyrating and twisting her hips.

“Answer me, John,” she ordered.

“Yes, Mistress,” I said obediently.

“And I’m even taking away any pleasure you might have been expecting this weekend, aren’t I?”

“Yes, Mistress,” I told her.

She slid the gloves sensuously off her hands. Teasing the soft leather from her fingers and tossing them onto the table.

“God it feels amazing to have that kind of control over you,” she groaned, thrusting her hands under her breasts and squeezing them.

“Thank you, Mistress,” I said meekly.

She moved close to me so she was only inches from my face.

“The crazy thing is that you can just reach out for the key. It’s here, John, hanging right between my breasts. I’m just a weak, pathetic woman and I couldn’t stop you just taking it from me – I wouldn’t even want to stop you. It wouldn’t be rape, because I want you inside me desperately. I want to feel the hot come exploding out of your c**k!” Her hands were stroking her body, pausing over her crotch, and then moving up to cup her breasts.

“But it’s even more erotic for me to deny you any kind of pleasure. Much more of a turn on for me to know you can only screw me with that rubber dildo. It doesn’t feel as nice as your c**k, John. But it’s me knowing that you’ll not be getting any sort of pleasure that makes all the difference for me. That’s how you can make me happy, John.”

Now she looped her thumbs into her panties and began to ease them down. I could see the crotch of the panties glistening with her juices.

“Get off that bed now!” she ordered. I scrambled off the bed, careful not to touch her.

She lay down and stretched out sensuously. She looked amazing in the black underwear, the stockings, and those boots. God I wanted her so much! Would she allow me to have her tomorrow, or Sunday maybe?

“I’m absolutely soaking wet,” she whispered, fingering herself gently.

She closed her eyes and began to masturbate in front of me. Her left hand came up and began to massage her left breast through the silky bra. She reached an orgasm really quickly and it was absolutely beautiful to watch the joy on her face. She’d moved forward so her p***y was only inches from my face. Now she flopped back onto the bed and lay panting.

“Fetch the strap-on,” she gasped.

I sighed and walked over to the table; the strap-on was where I’d left it earlier. I walked back to the bed, where Christine had her eyes closed, and was gently fingering herself.

I lifted my leg and stepped into the harness.

“You’d actually do it, wouldn’t you?” she asked, laughing.

“What?” I said.

“I really have broken you,” she told me. “That’s amazing! You’d screw me with that dildo just because I just told you to. You’ll spend all next week making up an excuse to tell Laura you’re not going to make love to her. That’s just totally f*****g incredible!”

“W-well of course, Mistress,” I mumbled.

Christine slid the chain from around her neck and gestured with her finger for me to approach her. She unlocked the CB3000 and dismantled it from my groin.

“That could do with a soak, but let’s deal with it later,” she told me. “Give yourself a cleanup with a couple of those wipes, sweetie; I may want to give you a blowjob if you can rouse yourself again later.”

Suddenly I was sobbing again, but this time with tears of joy and relief. Almost like a robot I wiped myself clean and turned to the bed. Christine had turned out the overhead light and she lay there lit by the soft glow from the bedside light.

“I don’t understand,” I told her.

“Sweetheart, you don’t need to understand; you just need to obey me. If you do that then you can’t go wrong, can you?”

My c**k was already hard; it had exploded out of the CB3000 and had rather enjoyed the wiping I gave it. I moved over Christine, who was smiling kindly. I saw two of my tears plop onto her breasts.