Every night for the following three weeks had followed the same pattern. When I came home from work, she would be waiting for me. She led me upstairs and tied me to our bed, before unbuckling the belt and washing me. Freed from its confines, my penis would swell to full erection - a response which delighted her intensely. Each time, she would tell me that possibly this would be the night when all my patience would pay off - then she would suck me and masturbate me right to the edge of climax, she would sit over my face and make me taste her while she would have orgasm after orgasm and play with my cock like it was merely her own personal toy and finally, she would pour icy cold water over it to make it shrivel down to the point where she could put that damn belt back on it, sympathise with me insincerely and tell me that perhaps tomorrow night would be more fulfilling for me.
In the mornings, she would make me wear a collar that she could cuff my wrists to, then lead me into the bathroom where she would take care of my personal hygiene. Again I would swell to full erection and would luxuriate for an all too brief period in the sensual pleasures of feeling my cock hard and throbbing, before that cold water would make a reappearance and signify that I was once more nicely cleaned up - and the belt would go on again.
And now, I just had to wonder⦠had she been doing exactly the same thing to Jennifer every day of the past three weeks too? And even as the question occurred to me, she answered it.
"I locked you both up on the same day," she said. "For three weeks, neither of you have been able to do a single thing about your sexual frustration. Alan couldn't even get a hard-on without my allowing it - could you, Alan?"
I blushed and mumbled something.
"Every day for the past three weeks, you've both relied on me to keep you clean. Every day, you 've both tasted me. I've never been satisfied so completely in my entire life. It's amazing. And you just both get better and better at it. But I've promised you both that it's going to be worth it in the long term, and tonight it will be worth it for one of you. But just one. Jim, take your trousers off."
I hastened to comply, and while I did so, she got on her knees in front of Jennifer and undid the padlock on her belt. It fell away and I saw Jennifer's fingers twitch. For a moment I wondered if she longed to plunge her fingers inside her pussy and start playing with herself right there and then, not caring that Anne and I were here to offer her no privacy. Anne undid my padlock too and removed my belt and my cock reared up, strong and proud. I think my question was answered then, for I suddenly burned to just grab it and start pumping. I didn't care who was watching. Then I looked at Jennifer and saw the heat burning in her eyes more strongly than ever as she stared at my cock and I knew that having a wank was just not going to be enough. I wanted to grab this woman and drag her into the bedroom with me.
"Sit down, both of you." Anne said. "One last game. Winner gets to cum as many times as he or she wants to, tonight. Loser has to do the honours. I get to watch. At the end of the night, the loser puts his or her belt back on. Winner gets to remain free for a week before being belted again, while loser has to be a slave to myself and the winner until the next game night. And on the first day of every month from now on, we meet here for another game. "
If you ask me why it is that we both agreed to this, I won't be able to tell you. We could both have simply refused to play Jennifer's game any more - she had effectively removed all the shackles she had placed on both of us. But there must have been some part of us both that enjoyed our situation, 'cos we both agreed.
My first word was "freedom". A great word - with another 50 point bonus - but I had no time to bask in pride at coming up with it, before Jennifer used my "r" to come up with "released". I scowled at that, lowered my head and knuckled under.
It was a close-run game. The stakes were high and we were both determined to win - but for some reason, it went on for a very, very long time. I gasped out loud when I first felt Jennifer's foot playing against my inner thigh, when I was stuck on a set of tricky letters and I realised that she was trying to distract me. Anne smirked and looked under the table, then walked over to my side and leaned against me from behind. I felt her breasts against the back of my head and her hand slid down my stomach, to nestle in my pubic hair. Eventually, I gave up and changed my letters, but then I dragged my seat round so that I could sit next to Jennifer.
I lowered my head against her shoulder and bit her gently. She gasped, but did otherwise did not respond, so I slid my right hand round her body and laid it against her stomach. I stroked her gently, up to the underside of her right breast and back down again to the edge of her neatly trimmed pubic hair, over and over. Eventually, she set down "pussy" and it was my turn again.
Her hand settled on my thigh this time and she laid her head against my shoulder, where she could look down and see what she was doing. I felt her fingertips brush against the underside of my scrotum and my whole cock twitched at the contact. Her hand moved and her fingertips closed gently round my cock and softly drew back my foreskin, then the tip of her thumb dipped into my precum and smeared it round my glans. I was breathing much heavier now, but otherwise managed to ignore her completely.
I put down "tease".
I lowered my head to her breast, then licked one of her nipples, just as my hand found her pussy and slid insideβ¦
I don't know how we managed to get through that game, but it was the closest one yet. When the scores were finally totalled up and I had managed to beat her by one point, I was initially elated and then terrified that Anne would order a rematch in order to produce a more decisive victory. But a result was a result, apparently and we were both led through to the bedroom.
My memory of the rest of the evening is hazy, to say the least. I have a series of jumbled up memories, in which Jennifer was teased mercilessly and brought to the brink of orgasm over and over again, while I came repeatedly. Anne made me lie on my back on the bed, in much the same position as she had made me adopt every night for the past three weeks, but for the first time she didn't strap me down to prevent me from masturbating or otherwise pursuing my own pleasures. Then, Jennifer got down on her knees by the side of the bed, took my cock in her hand and started playing with it gently. She sucked me off, she masturbated me, she endured every moment of her "punishment" without a single complaint. Finally, just before Anne put the chastity belt back onto her, so that we could all fall asleep in a tangled mass of legs and arms, she sat on my knee. She took my cock in her hand once more, then twisted her body so that her breasts were pressed against my chest, wrapped her other hand round my head and pulled me forward to kiss her, deeply. I came one final time, splashing my seed over her hand and, looking me in the eye, she raised that hand to her mouth and licked her hand clean.
"Enjoy this week," she said. "But you won't always win. And next time it might be me who gets to have all the fun." She smiled, wickedly and gave my cock a quick squeeze. "Mmm, I wonder how it's going to feel to have this monster being kept hard all night, but never letting it erupt." She slipped off my knee and dropped to the floor in front of me, without letting it go, then lowered her head and kissed it. "I'm going to enjoy finding out."
Anne smiled at us both. "You know something?" she said. "So am I."