A couple months passed. They were hell. There didn't seem to be a moment I wasn't aware of my clit. I leaked practically all the time. I never saw the results with my eyes, but the pumping left me overly sensitive and swollen. I knew it probably wasn't the case, but my clit felt three times bigger. When something actually turned me on, it had its own pulse. The deadline still felt a lifetime away.
Worst of all, my poor Michael was suffering too. He assured me he was fine, but no matter how well he handled it, I still didn't want him to have to. There wasn't much fun we could have while both locked up, but we made out, and he suckled my nipples. I stroked his balls, but he said it quickly turned to pain. It was difficult to keep my hands off them though. They were so big and swollen, full of the delicious cum that would put his baby in me. I wanted it so bad. I wanted him, his seed, and his baby. Our family.
With six weeks left, we walked into Tyler and Vanessa's apartment, as ready as we could be for whatever new torments they'd cooked up.
"Good news! We have a special session today," Tyler said. My face must have been very skeptical, because he laughed and continued: "I know, you think I'm being ironic, and it's actually going to be worse than ever. However, I have the cruelest torture possible in store for you: hope."
At that moment, I really couldn't hold my expression neutral.
"You see, one of our members paid the big bucks for a VIP session, which comes with two main benefits: he gets to join us in person, and he controls your orgasms during it. That's right, there's a chance of you cumming today. If the VIP feels like it."
I instantly started leaking, and my stomach did a weird flop. I couldn't believe what I was hearing.
I let myself be stripped and hooded.
"Gabriel will of course be supervising, but I don't think the VIP has much in mind for him."
I'm led to their bedroom, but not to the bed. In fact, it seems to have been moved. I'm guided to kneel, then go on all fours. I feel leather straps under my ankles, and then hands are fastening them around me. There are two more for my hands, and finally one goes around my neck and then is connected to a rigid pole. I'm on my hands and knees in some kind of frame. I have some wiggle room, but can't leave that position. I think they want me to be able to squirm, and my breathing quickens.
The latest lock is cut, and the chastity belt comes off. I feel a warm, wet towel scrape across my labia and more importantly, my clit. I suppress my moan, humiliated that this almost clinical contact is turning me on. Once I am clean, I hear the door open and softly close.
"Welcome! Chastity, say hello to... well, just call him 'Sir' unless he says differently."
"Hello, Sir," I say, probably much too quietly.
"She is very shy, no? I am enchanted."
His voice is pleasant, subtly accented in a way I'm not familiar with. European, most likely.
"I have submissives of my own, of course, but when I found your web site, and watched and read of your... predicament... I had to experience your exquisite suffering for myself."
A hand ran from my shoulder to my back, and then towards my ass, stopping briefly to squeeze.
"I have brought something special. I had to pay someone very clever to create my vision. You are lucky! My own submissives will soon be familiar with it, but you are the first. Let us hope my money was not wasted, eh?"
I feel a drop of something cool and slippery on the crack of my ass.
"You are no stranger to play of this kind, no?"
"Yes, Sir. You're right, Sir," I said, aware that the question was phrased ambiguously.
"And do you want to be penetrated there?"
I did. Of course my pussy wept for attention, usually literally seeping in frustration and arousal. However, despite my ass being a poor substitute, the familiar feeling of fullness that it brought had also been denied me for months. I wiggled my sadly empty holes at him, and spoke.
"Yes, Sir."
"Good girl. You are not so shy as I thought, perhaps."
I felt a smooth, rubbery blunt object begin to press into my ass, agonizingly close to where I wanted to be filled. It widened, stretching me, and I groaned, then it popped in and nestled between my cheeks. It had me shivering and winding my hips, but I recognized its shape as a buttplug. Did he really come here and pay exorbitant fees for that?
"Yes, feel it. Become familiar with it. But the magic has not started yet."
I didn't know what to make of this. I obeyed though. I concentrated on the feeling, relished it.
"You have a lovely pussy, my dear. The clit, so plump and ripe with need. The folds, so wet with desire. I also collect art; it is the same drive, I think, to see and be near things of such beauty."
I felt his breath, cooling the dampness that was exposed to his gaze. The toy in my ass shifted as he put his hand to it, and I squirmed, wanting a hard pounding, not a light prodding.
"Such a wonderful sight. Those who know my... proclivities... perhaps think that I do not like pussies because I do not touch or taste them... it is the opposite, ha! I could not take the risk of ruining such perfection with release. I adore them! Especially those that ache and suffer so beautifully as yours."
Soon I felt hands cup my hanging breasts, and slowly stroke them. I felt I was being measured more than caressed. A moment later, I felt something strangely familiar: a tube encircling my nipple, similar to the pump used on my clit. I sucked in a breath as a quiet electric motor came to life and confirmed my suspicions as my nipple was sucked into the tube. However, once it was in far enough, I felt it touch something soft, like the bristles of a paintbrush. A moment later, the suction steadied, and the device hung from my breast, pulling slightly. Another moment, and it buzzed to life again, but instead of more suction, the bristles began to spin. I gasped. It was intense but light as a feather. A second later, it cut off.
"You begin to see, no?"
My other breast received the same treatment, pulled into a cuplike tube until it reached the bristles, then a second of that maddening tickling to test it was in place. I rocked in my restraints.
"There is one more, the best for last."
Oh no.
Sure enough, I felt a third tube cupping my clit, pulling it in until it was nestled in the bristles. I gritted my teeth, nearly shrieking as the same tickling buzz hit me at the core of my sexuality.
"Ha, we are ready to begin! You have now felt what I paid for, but those cups, they are not what is special. Would you like to feel them all?"
I took a shaky breath before I answered.
"Yes, Sir."
"Then squeeze!"
I didn't understand. At first. Tentatively, I flexed my asshole around the plug, clamping down. The three cups sprang to life, tickling my most sensitive parts. It was almost unbearable, but it was driving me towards orgasm. Two seconds later, far too soon, it stopped. I panted. I squeezed again, and the same happened. I sped towards ecstasy for two seconds, then it was jerked away.
"I call it the anal tutor. It teaches the submissive to milk cocks. A simple task and a simple reward, but difficult to arrange. Keep trying! We will see if climax is in your reach."
