The First of the Month and a Possible Release

“How long have you been trapped in there?” she asked, stroking his caged genitals. The chastity device gathered up his balls and held them out so nicely that it was hard for her not to play with them. “How long did I say?” she pressed.

“Two months,” he replied, starting to breathe a bit heavily. She already knew the answer, of course, but wanted him to say it aloud.

“That’s right,” she said, acting as though she hadn’t actually known. “It is the first day of the month. What did we decide to call that special day?” She squeezed a little harder and he gasped.

“Maybe Day,” he answered. “Because maybe you’ll let me out.” The poor boy sounded hopeful.

“Yes, perhaps I will let you out on Maybe Day. But that is the only time it happens. Only on Maybe Day. Never on Second Day, Third Day, or any of the other thirty days in between. The first of the month is the sole chance for your release. And if I say ‘no’ today, you have to wait a whole another month for the next opportunity, don’t you?”

He groaned. “Yes.” His voice was barely more than a whisper.

“And you were so certain I would let you out last time, weren’t you?” He nodded as she continued to fondle his balls. “You’d never been locked up for longer than three weeks before that. When you agreed to the game, you were sure I’d release you on the first Maybe Day.” Her fingers moved across the tight sac, tracing the outlines of the tender and over-full sperm factories inside. His large frame, muscular and strong, leaned into her. His arms circled around her and his head sank down onto her shoulder. Gently he began to kiss and nibble the back of her neck, his hands holding the small of her back while his mass encircled her. His cock pulsed within its cage, lifting rhythmically, trying to expand but trapped by the unforgiving device.

“So I want to know,” she said, “are you sure you’ll be let out this time? Surely I wouldn’t make you go three months straight? Is that what you’re thinking about?” She felt his chest heave, his arms tighten around her, and his lips working frantically across her skin. She was breathing heavily now too.

“Or,” she continued, rasping the words just a little, “did last time teach you not to be so sure? Do you realize now that you truly don’t know when you’ll get out again?” She let go of his balls and ran her hands up his sides and over his shoulders. She pulled herself farther into his embrace. “Tell me,” she demanded. “Do you think you’ll get out tonight?”

He ran his lips up the side of her neck and nibbled beneath her ear. “I don’t know,” he whispered, continuing to caress the side of her face with his mouth.

“If I don’t let you out tonight,” she continued, “you have to wait until next Maybe Day. Another month of teasing and no release for you.” Her hands were back on his balls and her mouth found his lips. He groaned. “Could you make it that long?” she asked between deep kisses.

“If you make me,” he answered, squeezing her tight.

“I might,” she said in as cool a voice as she could muster while rhythmically squeezing his balls and tugging them up and down, back and forth. She was getting worked up, starting to get a little rough. “Or maybe I’ll let you out after all. We have something to celebrate tonight.”

“What’s that?” he asked grunting as she slapped his swollen balls.

“I’ll tell you later. Carry me to the bed.”

He picked her up and she felt the power of his body as he effortlessly carried her across the room and gently laid her down on the bed. She scooted to the center, pushed a pillow behind her head and spread her legs. “You know what position I want you in,” she ordered.

He climbed onto the bed and straddled her as if to do 69. With his caged cock and balls dangling above her face, he lowered his own face into her crotch and began licking. She idly stroked, pinched and slapped what she could reach of his privates while his tongue worked away.

“While you’re down there,” she said between small gasps, “I want you to think about something. I want you to consider what happens if I make you wait until next Maybe Day.” She felt the change in his rhythm, the increase in urgency as his mouth brought her steadily closer to orgasm. A stream of precum began to leak from his cage, the thin ribbon dropping like a spider’s silk thread to land on her chest. She felt the sticky slickness slowly run down her neck. “Do you want me to make you wait? Do you want me to say no tonight? To keep making you lick me like this every night until the next Maybe Day?”

He lifted his head ever so slightly and she heard him say “Yes, please yes” before his mouth dropped back to its work.

“Good,” she said, sinking into the pillow and feeling the first orgasm wash over her. “I… wanted you to… (gasp)…. say … say… ” she lost her words as the climax hit. His mouth worked hard through the release, then gradually eased up, continuing to gently kiss and lick her labia, avoiding her sensitive clit and waiting to see if she wanted more. He had gotten so very good at this. She sighed happily and told him to continue.

“You’ve earned it tonight,” she said. “You can lick me as long as you’d like. I’m not going to let you out tonight.” He groaned. “I’m glad you asked me not to.”

Much, much later, when his lips and tongue were finally too tired to keep going, he climbed off and gently pulled the covers over her. She was blissfully content. When he climbed into bed next to her, she reached up and felt the pool of precum he had spread over her chest. She wiped some of it on his chest as she rolled towards him and smelled her scent on his face. One hand slipped down to cup his balls. She felt his cock throbbing in its cage.

“You were very good tonight,” she told him. She began to get sleepy. As she started to doze off, she said “Oh, I almost forgot. The thing we have to celebrate. I got that promotion at work.”

“Congratulations.” he said, his overworked tongue slurring the word a bit.

“Mmmm,” she murmured. “But there is one little thing. It means I have to fly to New York for Corporate Training. I’ll be gone a whole week.”

“I’ll miss you,” he said thickly.

“I know,” she replied. “Especially since I leave on the 29th.” She smiled at the little gasp that caught in the back of his throat. “Happy Maybe Day darling,” she said and drifted off to sleep as a new torrent of precum began to pour out of him and over her wrist.