It's hard to believe it all started with some talk on a chat room. I was in college then, and always straight in real life, although not very successful with the ladies. But my dirty little secret was that I liked to go online and indulge my fantasy: being enslaved, feminized, and kept in chastity by a man.
At first, I'd wander through chat rooms and find a guy to be my Master for a night, and for an evening I'd be his little slut, giving my mind over to his pleasure, trying to be the girl he wanted. My fantasy was always being forced to serve while kept in some sort of chastity device: a belt or a cage, usually. In my mind, I'd be locked away, sucking my Master-for-a-day off, getting fucked hard in the ass, all the while my own little cock unable to stiffen or experience any pleasure at all.
But of course, in real life I'd be beating off like crazy. And then I'd cum, and the fantasy would be over, forgotten for a while. It was like that for a long time.
I've always been the monogamous type, though, so I guess it was natural I'd eventually find just one Master. And I did. Sean.
At first, it was just like any other time. But with Sean, even after I came, I felt strangely drawn back to him. There was something about him that drew the fantasy out of me: he probed me with his words, forcing me to bring up new wrinkles, new ideas, planting kinky new seeds in my imagination. Even now, I'm not sure how much of it was my idea and how much his: probably much more his.
Sean turned me on like no other. Instead of trolling around the chat rooms for new guys and new fantasies, I found myself drawn to him over and over. He was just so cool, so confident, and it seemed like his desires were the perfect complement to mine: he obviously wanted a feminized slavegirl as badly as I wanted to be one. It wasn't long before I was talking to him every night. Sometimes I'd find myself waiting up until 2 or 3 A.M. just to talk to him for a few moments. Soon after that, every time I masturbated, I was thinking of him (my mental picture of him, anyway) and my -- our -- fantasy. Over the weeks and months, it developed: me turned from a college boy into his slutty little housemaid slavegirl. My penis would be locked away in a chastity belt, and he would have the only key. If I ever wanted to come again, I'd have to serve him well with my mouth and my tight little asshole, working hard for one paltry orgasm a week. And meanwhile, he'd be mercilessly using me for his pleasure several times a day. My body would be transformed into that of a nubile little girl through a variety of fantastical means, whatever struck our fancy: surgery, drugs, magic.
Eventually we switched to phone sex. We always talked about this fantasy, always adding new episodes, new wrinkles. And I always came at the end, as did Sean. But gradually Sean began to probe me in questions about my real life (somehow he always dodged mine). I told him my problems: about how hard it was to make ends meet, about how I was failing out of school (mostly because I was talking to Sean and neglecting my work), about how I had no job, about how I was alone in a strange city.
And one day I was short on my rent. I told Sean. Sean said, "I can help you, my little slavegirl. But you'll have to do something for me."
I was nervous. "What do you want me to do, Master?"
"I want you to stop masturbating, slave. It's not proper for a slavegirl. And you are my slavegirl, right?"
I gulped, but said, "Yes, of course, Master."
"Then show me your faith, slavegirl. I want you to stop masturbating."
There was a pause while I considered this. "But-- but I don't think I can, Master."
"I know that you can't, slavegirl. You're weak. And that's what makes you such a good little slave. But I want you to try, really try. If you do this for me -- if you be my slave -- I'll take care of my slavegirl, like a good Master should. Do you understand?"
I considered it. Knowing I'd try, knowing I'd fail. I'd masturbated every day, more or less, since I was twelve. But Sean asking me to do this -- give up my orgasms for him, start making the fantasy a reality -- was just so hot. I was already rock hard, just thinking about it. And I did need the money -- my rent was already late. "I... yes. Yes, Master."
"Yes what, slave? I want to hear you say it. Promise me."
"I... I promise I'll stop... touching myself..." I stammered. "...stop masturbating, for you, Master Sean."
"Good! And I promise I'll take care of you as long as you remain true to me, slavegirl. Now go to bed."
And with that, he hung up. Leaving me alone, in my apartment, with my hard cock in my hand.
I thought about it. But I kept my word. I stopped touching myself and crossed my arms, gripping my forearms tightly. I went to bed like that, and laid there for a long time, trying not to think about how turned on I was, trying not to think about Sean and what I had agreed to.
Eventually I fell asleep. Without coming. The next day in the mail was an envelope, shipped express. Inside it were ten crisp new hundred dollar bills. And a note:
"I keep my word. Do you, slut? - Your Master"
I was instantly very, very turned on. It was mostly the note, but the money didn't hurt either. And being turned on by the money only made me feel sluttier. But I was good, all that day.
Inevitably, though, I cracked. Later that week, I jerked off, as I had known I would. And as my Master had known I would. But I did the right thing: I told him. He wasn't surprised.
It went on like this for a few months. Master was paying my bills, and I was servicing him at night on the phone. I'd talk dirty to him, hear him cum, and then go to bed quivering and horny but trying so hard to be good. And when I failed, I'd tell him. He seemed understanding.
But then things changed. I had failed out of school, and still had no job. I was just barely making ends meet on the $1000 a month Master was sending me. Eventually, the rent was late again.
"Master... your slavegirl humbly informs you that her rent is late."
"Is that so, slavegirl?"
"Yes, Master. I'm sorry."