So I began my first month in lockup. Going for a week at a time without an orgasm had been rough, so I had no idea how I was going to survive a month! But I was intrigued by the idea, I have to admit. The first week was a breeze – much to my surprise. Before, a week seemed like an eternity, but now, facing an entire month in chastity, a mere week was child’s play.
My Fair Lady was pleased with my behaviour after a week and decided to reward me. Not with an orgasm, of course, but the Sunday evening of my eighth day in lockup she cuffed my hands behind my back and removed my device for a few hours of freedom. Relatively speaking, that is.
Even though I was in chastity, every night I spent about an hour pleasing MFL orally. At first, I thought this practice to be cruel and unusual. But I was starting to get a thrill from it. She was very impressed with my submission to her and we made it though the second week without incident.
That weekend, MFL announced that although my oral skills had drastically improved over the past few weeks, she needed to feel penetration. She didn’t think it was appropriate to give me another chance to penetrate her without cumming, so she took me to an adult toy store to find a suitable dildo. It was both humiliating and exciting to help her choose one. She told the clerk all about my situation. He didn’t seem too surprised. Must get a lot of couples like us in there.
We finally decided on one, made our purchase and then headed home. MFL could barely contain her excitement! She fondled her new toy all the way home, teasing me as she carressed and licked it, reminding me that I still had two more weeks to go.
That evening was quite a thrill for the both of us. MFL directed me on exactly how she wanted me to use her new toy on her. She had me alternate between pleasing her orally and using her new toy. She pointed out how much bigger it was than my own, pathetic, caged cock. As I licked and dildoed her to orgasm after exhilarating orgasm, she wondered aloud if she even needed my cock anymore.
This really did a number on my psyche, I have to admit.
Nevertheless, I eventually made it. One full month in chastity. No orgasms, only a weekly 2-3 hour release while my device was being cleaned (my hands stayed cuffed behind my back the entire time I was “free”). I tried to mentally prepare myself for what was going to be an orgasm like I’d never experienced before. I could only imagine!
That night, MFL brought out the cuffs and asked me if I was ready. “Yes Ma’am!” I enthusiastically responded. She dressed in her finest lingerie and cuffed me to our bed. The anticipation was about to kill me! She wore the key to my device around her neck, which she then took in her hands and began to fumble with the lock on my CB 3000. Then a puzzled look came across her face.
“Wait a minute,” she said. Her face wore the expression of someone doing math in their head. “Tell me,” she started, “What did I say would be your punishment for cumming during our last experiment?” Was this a trick question?
“One month in chastity, Mistress,” I polietly resonded. “Yes,” she replied. “And how long has it been since that failed experiment?” Again, the answer seemed obvious, but I treaded lightly. “It has been one month, 30 days to be exact,” I answered. “Yes,” she continued. “But didn’t you have a week left in chastity at the time? The one month sentence was IN ADDITION to the time you ALREADY had left in chastity. Isn’t that right?”
My heart sank. I proceeded cautiously, not wanting to be accused of arguing and getting more time added. “Well, I thought you meant one month total. We even marked it on the calendar, see?” I gestured with me head to the calendar on the wall with today’s date circled in red. “Yes, my dear. I see the calendar, but I’m afraid I’ve made a mistake. You will have to wait one more week and serve out your full sentence. We wouldn’t want to cut any corners in your training, now would we?”
“Of course not, Misstress,” I responded. If I had learned anything so far, it was to never question the judgement of the woman who is holding the key to your cock.
One more week to go…