Hannahs Way

This is a work of fiction with a healthy amount of facts. Hannah is a real person, and is like no other person I have ever met. The people you will be introduce to along her journey are also real and most of these adventures actually happened. I am fortunate enough to be her mentor, guardian, her lover and her Mistress. This will run into many chapters as our journey is ongoing. Please enjoy the read and leave a comment, even if you don't like it. Everyone who has sex in this story is well over 18.

Part 1 - Meeting Hannah

It was late, almost midnight. I was tired and definitely unsociable. I had been in the chat rooms on Literotica for almost 6 hours, got into some discussions and disagreements and in no mood for much more. I was about to log off and was saying my good nights to few people online I happen to call friends.

Hannah interrupted my goodnight wishes with a very nervous, hello Mistress. How could I tell she was nervous, easy, she told me so. I was caught in two minds, did I just log off or do I reply.

Well being rude isn't part of my persona, so reply I did. I simply asked how I could help her. She said she had read my profile and she felt drawn to me. That she had never done anything like this before. Chat to strangers online. I asked the obvious questions, who she was and what was she looking for. She told me that she felt she was submissive.

No she then said "I'm very submissive."

That she was looking for someone to teach her, train her. As I said it was late, I was tired and in no mood to be messed around by some 'wanna be' sub who thought that being a sub was some kind of game and a bit of role playing fun. I told her, at this time I was assuming it was a female, to look me up tomorrow my time as it was late where I was and need to get to bed. Thinking that would be the last I would hear from her. I had to keep reminding her that even though it was six o'clock in the morning for her, it was after midnight for me in Australia.

To my surprise and somewhat delight, Hannah, returned on time. Called me Miss. All of this from one very brief late night chat. I spoke firmly to her, and laid it on the line. This was no online game for me. I took it very seriously, and she would have to do likewise. She assured me she would and was ready for anything.

I laid down the law, she will call me Mistress. When she greets me, whether it be in a chat room or in a private chat room she would do so in the same way every time. She would describe to me in detail what she was wearing, from her underwear, to her makeup. There would be punishment for failure and there would be rewards for achieving set targets.

It was at this time that I was having issues with Lit, trying to stay connected. I was on for two minutes and then booted off. It happened nearly every time we were online together. I was certain she must be feeling totally despondent and neglected. Fortunately I had other means of staying connected, apart from our emails.

Thank god for Trillian. We started chatting on Trill and it was so much better and easier to chat. Plus if I wanted to include others I could and a small group could chat at the same time.

It was obvious to me that she is very submissive, shy at times, and wanted a lot from our online relationship. She had never been with a woman before, not even in college. Yes she thought about it, she told me she thought about it a lot. She really wanted to experience that. We chatted on and off for several weeks getting to understand each other. I learnt she was a mother of 2 school age children, lived just outside of NYC was reasonably happily married.

Was sex starved, as hubby got his weekly quota of 3 minute sex. What's that old saying? Whip it in, whip it out and wipe it. Very unsatisfying for any woman. I reassured her that all I could do was to paint a picture with words, she would have to do everything else. We laughed over it.

Her first big test came soon after. She would have to send me a photo of herself. Nothing racy, just a photo, so I knew who I was dealing with. I didn't expect her to respond, or if she did it would be some random photo off of the net. I truly expected the online relationship to end there and then.

The following day it arrived in my email. A photo of a good looking woman, blonde, pretty, smiling, perky breasts. When she came online, she was sure that I would be disappointed in her appearance. Even though I reassured her, she was extremely good looking, her lack of self-confidence came to the fore.

She begged me, which thrilled me to my bones, to humiliate her, to have sex with her in every conceivable way. She craved my attention and wanted more and more of me.

I loved it.

I introduced her to the joys and pain of anal sex. She ordered and received a set of plain black butt plugs, silicone, smooth, sexy and in 3 sizes. We arranged to insert the smallest one, 3" in length and only 1/2" in Dia. She did exactly as she was instructed to do. And showed me so. I instructed that she take some sexy and very explicit photos. She did and duly sent them to me.

We masturbated together online.

I kept demanding more and more from her and she kept complying.

I reassured her that she was ready to wear my Collar.

She was thrilled, excited I could sense it in her words. The drama came when I asked for her street address. That proved to be a step too far.

End Part 1