Lynn's Journey Pt. 01

I met Lynn at work and was immediately struck by her lean, brunette, eye-glassed, nerdy sexiness. The first time we talked was at a bar, where we both stayed too long and got too drunk. We had a genuinely fun time together and I knew she had potential.

Over the course of two years and intermittently running into each other at work-related bar binges, our conversations got more and more intimate with less and less innuendo. We are both married with children and work for the same company (in different locations), so secrecy and trust were of the utmost importance. Our situation was perfect - mutually assured destruction if one of us let out our secrets.

Ultimately the stars aligned, and we were in the same city at the same time. I spent an hour preparing the suite...dozens of candles, some scented, but no two the same - musk, vanilla, oak, magnolia, patchouli, lavender. Enough candlelight so that no lighting was needed. Vodka chilling on ice. A white comforter on the bed, turned down. Music from my ethereal playlist in the background, but barely noticeable.

Lynn came to my room on her own. Alone. Lynn was seduced that night and she came like she had never cum before. She talked on the phone with another sub while I made Lynn cum for me. Lynn listened on the phone and played with her pussy and made herself cum while I talked my sub through a fast and furious phone session right there.

Lynn discovered that some pain increased her pleasure. But most importantly, Lynn became my sub that night.

This is a true story that covers a year-and-a-half long-distance Dom/sub relationship. There will be many chapters. The writing is exactly as it was, cut-and-paste from the emails, and has not been edited. This may not lend to readability, and sometimes the responses to some emails are not chronologically in time with each other. Most writing was done quickly and urgently, since we are in different time zones and have families to attend to, so it may be less than perfect grammar.

The names have been changed, and any personally identifiable details have been removed, but the rest is exactly as it was.

This is my first submission and I look forward to your feedback.

Moths To Flames

On 5/27/18 at 8:43 PM, Lynn wrote:

Thank you for your email address as well as the feedback, Sir. I have disabled both notifications (per your instruction) as well as automatic error reporting.

I kindly recommend you turn off that setting as well, Sir. I have some personal experience, and friends, who have been able to commandeer this data from other services - respectfully, I'd rather error on the side of caution, Sir.

I've read a good amount of my novels, and the only question I have right now is: When the time comes for spanking, could you please start with just a hand, Sir? Floggers seem a little advanced for me at this time.

On 5/27/18 at 8:24 PM, SIR wrote:

I am happy that you want to be spanked. When, how much and with what is up to me. It will give me great pleasure when you offer your ass to me, but you can know that I don't use whips.

I don't know what novels you're reading, but I realize that you and I may not be on the same page yet. You have to work your way up to being spanked. You have to earn it. I see great potential and willingness, but you are not there yet. This is a process. It is not a game.

And don't forget...if you are to be spanked for punishment or disobedience it will be swift and extremely unpleasant. It's a requirement that you not enjoy it.

You mentioned that you would like to spank yourself. Would you like to spank yourself Lynn?

On 5/18/18 at 4:54 AM Lynn wrote:

I would love to spank myself, Sir. However, I want your expertise at least once more before I start the path of self-exploration, Sir - simply out of respect for your art. That was the first time that has been introduced to me, so I was too enraptured to retain the specific details on how-to. Sir, it was damn good - sorry, not sorry - I was rather... enthralled.

I understand this is not a game, Sir. I apologize if my tone (word choice) implies otherwise. I am learning and trying very hard - this is not my natural disposition, Sir.

My novels are 110% not factored into any of this. Historically, I have had very, _very_, negative sexual encounters. I use the books as a way to at least understand the nomenclature, Sir. I don't like surprises, but I make an exception for you. Sir.

On the subject of punishment, I adore being called your 'Good Girl'. I will do all that I can, and that is recommended, to retain that. However, I know I am far from perfect and punishment is on the table.

[Personal paragraphs deleted]

Sir, thank you for reading this long message. To be honest, I imagined you reading it to yourself and me kissing those delectable lips as you mouthed the words. I apologize if feelings like this are not allowed but Sir, I felt you should know - you are the expert after all.

On 5/18/18 at 12:13 PM SIR wrote:

There is so much for me to learn about you. I'm concerned about your use of "was/is". You must tell me more when you are ready to. And you are predisposed to be submissive. Embrace it. It takes a strong, self-assured and confident person to be a sub.

I used to write session-based erotic stories for my subs. I don't anymore because it takes a lot of time and I haven't been inspired. Maybe that is changing.

Here is one from a while ago that I changed to be just for you. It's short and sudden. Read it slowly. Unfortunately, it's the first I came across and it's about punishment. Trust me, I am all about pleasure and having you be my Good Girl. I am not obsessed with punishing you. In fact, I hope I never have to.

This story assumes a lot of our learning and rituals have already taken place...undressing, cleansing, makeup, commands, positions. More on that later.

You may masturbate freely and cum as often as you like as you read it, but more importantly, you must remember everything and respond to tell me how the story made you FEEL. You must also tell me in vivid detail how you touched yourself as you read it.

I enjoy reading long emails. Take your time. I need to know what is going on inside you. Once you start to open up it will flow. It's only me. Trust me. You need this.

Lastly, you should stop here until you can be alone and enjoy yourself as you read it. Fat chance that will happen though, and I won't set you up to disobey me.

- - - - - -

Lynn's Punishment

"What's the safe word, Lynn?"

"Red"

"Let's begin, then"

"Present your pussy"

You do as you've been trained and, lying on your back, you place your arms under your knees, pull back and spread. The motion lifts your ass off the bed and spreads your pretty little pussy open. It glistens. You feel vulnerable and slutty. And scared.

You look over your stomach at your pussy as I lean down and kiss it. I suck on it, you feel the pressure inside you as I suck your juices from inside your pussy, from deep within your center. Your hot, sweet juices.

I move up, over you, I lean down, drawn to your red lips. Your eyes lock onto mine. My face lowers. Slowly your lips part. My mouth attaches to yours. My tongue pushes your juices from my mouth to yours. You relish the taste of yourself on my tongue. Your taste...my taste...so sweet...

Off the bed, over to my bag. The vibrator, the big, wand vibrator, a stick with a smooth ball the size of your fist on the end.

It's on. You can feel the vibrations through the air. Your pussy tingles. The ball comes down on your clit. The sensations are overpowering. Pussy pulls away then bucks forward against it. It hurts. No, you need it. You are helpless to do anything. I press the ball onto your pussy. Hard. On your clit. On your pussy lips. Against your cunt hole. Minutes go by. Just you and your pussy on my vibrator. I see your stomach twitch. Just a few more seconds then...nothing. No vibrator. You pussy is starting to spasm.

"Don't cum!"

"Please Sir, may I cum!?"

"DO...NOT...CUM!"

"Oh Sir! Pleeeaaase! I can't! I'm going to cum"

"Ask me if you may cum"

You're pleading with me now. "Please Sir, may I cum? May I cum? May I cum?...Please let me cum Sir..."

"You may NOT cum!"

A slap with my riding crop on your exposed pussy. Pain. Pleasure. No control. The explosion of the crop on your pussy almost sends you over the edge. You fight it with all your will. Slap...slap...slap...right on your cunt...pain...wetness...The riding crop slides up along your thigh to your knee. It leaves your skin...prepare for the...slap! Inside your knee. Exquisite pain. Straight to your pussy. Oh god. You hope for more.

Slap! Your inner thigh. Slap! Sting! Slap! Sting! Slap! Sting! So close to your pussy. You're wet and dripping and on fire. My pretty little pussy is throbbing.

Slap! on my pretty little pussy. Slap! Sting! Slap, slap, slap! But you aren't allowed to cum. You're so frustrated...sobbing...tears...mascara running down your cheeks. So beautiful.

Come back to me Lynn...don't leave me yet. My hand caresses my pretty little pussy, gently rubbing the sting away.

Then I stand back. You feel alone.

The smooth cane slides along the bottom of your foot. Oh God, you hate this, you prepare yourself. You're helpless. Nothing to do but submit.

"Put your feet together"

You contort and stretch to bring them together above you. Your abdomen is restricted, it's hard to breathe...You're staring at the space between your legs, at your pussy.

"Count"

The cane slides along the bottom of your foot in small circles, teasing, almost tickling, then lifts. Then that sound. Swoosh! The sudden pain in your feet is like a thousand bee stings. Its an explosion of pain. Straight through your cramping legs to your core, to your soul...

"one" "ow ow ow"

It lifts, you hear the swish as it cuts through the air, then another explosion on your feet.

"two" through gritted teeth "fucker!"

small soothing circles on the bottoms of your stinging feet. Swoosh!

"three" "fuck!!"

a light touch...nothing...the sound...the sting!

"four" "please, please, please, no more, please, please"

immediately another...Swoosh!

"four"

"No Lynn, that was five. We will have to start over again."

You are almost broken. "No! Sir! Please..."

The cane is once again rubbing gentle circles on your feet. Soon it will start. The pain like no other. Your pussy is wet, dripping down your ass, on fire.

Someone touch my pussy! The confusion sets in...you feel it coming on... subspace...your brain is screaming

"I'm afraid...I'm so weak...so degraded..."

'Red! Red! just say it out loud and it will stop..."

"No, I need this..."

"I hate this!...I hate him!...

"I want this...I want this for him..."

"I need this...I can take this and more...fuck him!"

The tears begin, the sobbing, the flat-out chest heaving, mouth drooling sobbing. This is when you let go. That's it. Let it all out. Let it all out Lynn. Go to your subspace. Give yourself to me. I will set you free.

It begins again.

"one..."

"two..."

Your body is not yours. You feel inside out, so sensitive, as if a single touch can set you off.

The voice is yours, but its detached from you... then finally

"five"

Firm hands separate your feet, spread your legs wide, stretching them. I rub my hand up and down your pussy lips, then slowly slide two fingers in, so long and so slow..."Now you may cum"

Your orgasm starts immediately...humping and bouncing and yelling...squirting and twisting as I hold my fingers deep inside you, I slowly pull back and slide them in again...my pretty little pussy spasms around them, squeezes and pulls them in...still coming and coming...babbling incoherently...pushing them deeper...

"Thank you, Sir!. "I'm coming for you Sir, I'm coming for you Sir, I'm coming for you Sir, I'm coming...I'm coming..."

Taking you, making you mine. Finally, your orgasm subsides, you're staring into space at nothing in particular, your eyes are glazed, your breathing is hard and fast, you try to talk, but only gibberish comes out. I step back and roll you onto your side.

Large warm hands covered in cool lotion rub the bottoms of your feet. It's immediately soothing, sensual, fingers rubbing the pain away, the strong lotioned fingers slowly slipping between your toes, so erotic. It's all you can feel, the warm loving hands bringing you back, reassuring you that everything is OK, that it's over.

I lay behind you and wrap myself around you, warming you. "It's over Lynn. You're a very Good Girl and you've made me very happy." "I'm very proud of you, Lynn." I pull you even closer to me.

You feel safe and protected.

"Thank you, Sir"

On 5/28/18 at 4:31 PM, Lynn wrote:

First, thank you for the erotic story, Sir. My #1 favorite thing on Earth is reading so I will savor this gift on multiple levels. Additionally, in order to maintain my Good Girl status, it will be read, and thoroughly enjoyed, when I have alone time, Sir. Just reading that something was written for me had me wet so thank you in advance, Sir.

Next, thank you for expressing concern about [deleted]. I appreciate you listening and respecting this limit more than I might be able to express.

[Paragraph deleted]

We've been together 14 years and there was a stage early on where he felt physical punishment was an option, so it was a surprise - I thought that was over. He once slapped me in front of Emily over missing a credit card payment. I snapped and broke his nose. That shit should never be done in front of kids. I thought that ended it, so to try that shit again 3 years after having his nose broken was a bit of a mindfuck. I wish I could say it would never happen again, but I just don't know.

Sir, thank you for reading and thank you for letting me share. Not many people know these details but I feel I can try to trust you, Sir. I understand that punishment is part of this - I am prepared and I consent. I feel that you will use this authority wisely and not recklessly like people have in my past... which means a lot. Thank you, Sir.

On 5/28/18 at 1:59 PM, SIR wrote:

Thanks for sharing your story. What a horrible life for a child and mother. I promise I will make you a stronger person than you already are. What we are going to do is not for the weak or confused.

A lot of what we will do in the near future will be through email. I will seduce you with my words and train you. If you like to read, it's perfect. And besides, it's all we have at the moment. Continue to ask questions.

I look forward to your emails as much as, or more than, you do mine.

On 5/28/18, 3:58 PM Lynn wrote:

Thank you again, Sir. What will be my first lesson?

To be honest Sir, I am rather nervous about all of it, but illogically, the more... 'feminine arts' ideals like make-up, or any specific beauty routines have me petrified. I have limited experience and they will require significant practice on my part. I also find the application frustrating, but I will do it for you, Sir. Please share what you would like to see and I will make it so (after undoubtedly a few embarrassing misfires), Sir.

Also, is there a specific color that you would like me to wear? I will be shopping for new clothes in the coming weeks and I will have you in mind the entire time, Sir.

On 5/28/18 at 5:28 PM, SIR wrote:

Been running like crazy. Plane is taxiing. Land in London in 7 hours. You have the right idea. Details will be filled in. I like dresses and skirts and summer dresses. Just above the knee. In my presence you may wear an ivory camisole if anything at all.

More to come.

On 5/28/18 at 11:08 PM, Lynn wrote:

Thank you, Sir. Looking forward to more details and I can definitely comply with dresses. Will skip the camisole for now - seems like it would just get in the way ;) Safe travels, Sir.

On 5/28/18 at 8:08 PM, SIR wrote:

Since we're doing this in sessions when we rarely meet and not 24/7 it's very important that we make the best use of our time.

Before you arrive you will have painted your nails, on hands and feet. If you arrive and they are not painted, you will be punished. Hands and feet must always match. If they do not, you will be punished. Any shade of red will do. An elegant red, not hooker red. The wrong color will disappoint me, but you will not be punished.

You will wear mascara and eyeliner in my presence. I do not require that you wear makeup on your face and eyes, but you may do so if you choose to. I require mascara and eyeliner in my presence, or you will be punished.

Lipstick is critical for me. I find it highly erotic...the smell...the taste...the feel. Not lip gloss, not some other lip covering. Lipstick. Any shade of red will do, but again, you must choose an elegant red. You must always have lipstick on your lips in my presence. You must learn to apply it quickly and properly. If I have to point out that your lipstick has worn off, you will be punished. You may use a mirror, or your fingers, or some other method to determine if you need lipstick, but you may never ask me if you need lipstick. You may apply lipstick as often as required to meet this requirement. I never tire from watching a woman apply lipstick.

You may choose from one of the following perfumes to wear: Poison by Christian Dior, Giorgio Beverly Hills (yellow and white stripes), or Design by Paul Sebastian. They are from the 80s. I'll tell you more about that sometime. Poison can be expensive...it is not mandatory, but you must choose from these three, else wear nothing. If you wear another perfume, and it pleases me, all the better. If it does not you will be punished.

I do not require that you spend a lot of money on these items. Spend what you can afford. If you cannot afford something that I require, say so, and I will pay for it. Do not be ashamed or proud about this. Be truthful. I do not want to punish you for lack of money. That must never happen.

You must keep your pretty little pussy pretty. This means you must maintain it. I prefer waxing to shaving, but shaving is acceptable. I love that you have such downy hair on your pussy, it was perfect. I loved your pussy as it was. That is your goal. If there is ever shaving stubble on MY pussy, you will be punished.

Regardless of what you are wearing, you must never wear underwear in my presence, unless for sanitary purposes. You must never, ever wear underwear with a dress or skirt, whether in my presence or not. If you are found wearing underwear when you should not be, you will be punished.

You must not wear sensible shoes in my presence. You do not have to wear 6-inch heels, but no flats unless they are sandals. Check out Nine West shoes. Pretty much any style they have is acceptable. You don't have to buy Nine West, it's just a reference. If you're not sure about a pair of shoes, send me a pic and I will approve or disapprove. There is no punishment for shoes at this time.

Lastly, you must prepare your ass for me before each encounter since we never know when it's going to be time to explore. Two hours before we meet you must cleanse yourself with an enema. The proper way is to buy Fleet enema, empty the fluid that comes in the container, and replace it with 1/4 teaspoon salt and distilled water. Give yourself the enema and hold it as long as possible. Do it twice.

I will be giving you an inexpensive simple piece of jewelry to wear on your ankle. It is the only jewelry you are required to wear. You must wear it at all times, not just in my presence.

Next. Lesson 2. Arrival.

On 5/29/18 at 1:30 PM, Lynn wrote:

Thank you for the detailed instructions, Sir. Your note has me equal parts terrified and turned on - but that's not a bad thing. I took the evening to read this over multiple times, so I have a number of questions. Would you please review them at your leisure, Sir?