Lynn's Journey Pt. 01

1. Elegant Reds - I interpreted that as vintage Cartier box red and deeper. No Corvette red. No orange-reds (reminds me of old ladies in Boca Raton, pass). No pinks. No deeper than a cherry wood red. Am I close?

2. Nails - Are acrylic nails acceptable? I have a terrible habit of biting my nails and will try and stop for you, Sir. However, it's a 30-year habit, it will take time and I want to try to be the best looking I can be for you, Sir.

3. Lipstick - Since this is extremely important to you, and an area I have zero experience in, I will be making this a priority for my practice, Sir. Is there one brand you prefer over others, Sir?

4. Perfume - Again Sir, an area I have zero experience in, but I will try my best for you. Other than online vendors, is there a specific retail store that might have all three available for testing?

5. Money - Thank you for the generous offer to purchase items that might be out of my budget, Sir. More importantly to me is that you said you would never punish me for lack of money. I truly, wholeheartedly appreciate that statement, Sir. I will do a little research on everything this week and let you know what I might need help on. Thank you, Sir.

6. Pretty Little Pussy - No questions on this topic. I'm glad you liked it, Sir. I read this part about a dozen times and was grinning from ear to ear every time. Thank you, Sir. I much prefer waxing this area over shaving. To be honest Sir, I booked the waxing appointment the day I knew you were coming into town so that any irritation would be settled prior to your potential viewing. I have sensitive skin - irritation always happens. I figured that even if I did not have an opportunity to see you, at least I could have a sexy little secret around you, which I would have settled for. I'm very happy you ended up seeing the final product, Sir. Even just thinking about it makes me wet, Sir. Thank you, Sir.

7. Shoes - Thank you for an example of an accepted brand, Sir. With a billion different styles on the market and shoes being *heavily* referenced in my books, this topic had me a little nervous. The reference was wonderful and alleviated all concern for this topic. Thank you, Sir. I still might send you pics though. Would that be acceptable, Sir?

8. Ass Preparation - Talk about a concept I have ZERO experience in. How much of a requirement is this particular ritual? Like you told me before, you don't know it's a limit until you crossed it, so again, I'll try, Sir.

9. Ankle Jewelry - No questions on this topic. Want to only say thank you in advance for the sweet gift, Sir.

Normally I would apologize for the number of questions, but not today, Sir. There will be more. I'm excited for eventually receiving lesson 2. Now for some breakfast and (finally!) alone time with your short story.

On 5/29/18 at 5:13 PM, SIR wrote:

I wrote those on the plane while fighting off sleep and the prying eyes of my seatmate, so I also had the brightness turned down to almost totally dark so it may be illegible at times. See below for my responses

On 5/29/18, 2:30 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?

1. Elegant Reds - I interpreted that as vintage Cartier box red and deeper. No Corvette red. No orange-reds (reminds me of old ladies in Boca Raton, pass). No pinks. No deeper than a cherry wood red. Am I close?

Yes, but I'm also a fan of the Urban Decay palette, which is very dark. I also realize since I sent the original that with your fair skin it's highly likely that pink is a more suitable color for you. Pink is acceptable.

2. Nails - Are acrylic nails acceptable? I have a terrible habit of biting my nails and will try and stop for you, Sir. However, it's a 30-year habit, it will take time and I want to try to be the best looking I can be for you, Sir.

Acrylic nails, not too long, are a great way to force you to stop biting your nails. Now you have a reason for the sudden interest in them.

3. Lipstick - Since this is extremely important to you, and an area I have zero experience in, I will be making this a priority for my practice, Sir. Is there one brand you prefer over others, Sir?

I prefer basic lipstick like Covergirl, Maybelline, L'Oréal. They are all acceptable

4. Perfume - Again Sir, an area I have zero experience in, but I will try my best for you. Other than online vendors, is there a specific retail store that might have all three available for testing.

Try Fragrance Outlet or Walgreens.

5. Money - Thank you for the generous offer to purchase items that might be out of my budget, Sir. More importantly to me is that you said you would never punish me for lack of money. I truly, wholeheartedly appreciate that statement, Sir. I will do a little research on everything this week and let you know what I might need help on. Thank you, Sir.

You are welcome.

6. Pretty Little Pussy - No questions on this topic. I'm glad you liked it, Sir. I read this part about a dozen times and was grinning from ear to ear every time. Thank you, Sir. I much prefer waxing this area over shaving. To be honest Sir, I booked the waxing appointment the day I knew you were coming into town so that any irritation would be settled prior to your potential viewing. I have sensitive skin - irritation always happens. I figured that even if I did not have an opportunity to see you, at least I could have a sexy little secret around you, which I would have settled for. I'm very happy you ended up seeing the final product, Sir. Even just thinking about it makes me wet, Sir. Thank you, Sir.

You get wet a lot lately. I like that. A lot. You have a beautiful pussy.

7. Shoes - Thank you for an example of an accepted brand, Sir. With a billion different styles on the market and shoes being *heavily* referenced in my books, this topic had me a little nervous. The reference was wonderful and alleviated all concern for this topic. Thank you, Sir. I still might send you pics though. Would that be acceptable, Sir?

Yes, it is acceptable. Low cut, heeled boots are my favorite. Pumps and sandals are next favorite. No 'princess' heels or any other type of starter heel!. Oh, no mules and none of those shoes that look like the front was cut off and your toes are sticking out. What the fuck is that about?

The shoes you're reading about in your novels are for Dominatrices. It's part of the costume. You are a sub. You will never wear those kinds of shoes. While we're on the subject...

My goal is to turn you into a beautiful, desirable, confident woman. Not a slut. I find women who dress like sluts to be empty vessels. If you want to be a slut, go the bar, pick up a stranger(s) and get fucked. You will not dress like a slut. I don't want a slut. You will dress like the Mom you are. Respectably and with attention to detail. That's sexy and alluring.

Speaking of shoes referenced in books. You should also know that the novels you are reading are written by people who likely have never actually lived this lifestyle. It's their fantasized idea about how it works, and it's usually wrong, and sometimes dangerously so.

8. Ass Preparation - Talk about a concept I have ZERO experience in. How much of a requirement is this particular ritual? Like you told me before, you don't know it's a limit until you crossed it, so again, I'll try, Sir.

WTF. This is not a negotiation. You will do it. Period.

9. Ankle Jewelry - No questions on this topic. Want to only say thank you in advance for the sweet gift, Sir.

You're welcome.

On 5/29/18, 6:05 PM Lynn wrote:

I intended to eat breakfast, then read your story, but I was too excited and went straight to my room. My lox bagel could wait. I've waited enough.

Your note prior to the story implied that I would read the story prior to being alone so I made it a point, respectfully Sir, to prove you wrong. I didn't read the story before now - it killed me a bit (read: a lot) on the inside because I **REALLY** wanted to, but I waited.

Worth it, Sir.

I put the breakfast ingredients back in the fridge and hopped to my room. I wasn't quite sure how to prepare myself so I decided to take off all my clothes. Given that you asked me to tell you about how I felt/acted during the reading, I thought it would best to remove my old Grateful Dead shirt and duck panties. They were not on your preparations list after all - Ha.

I grumbled to myself a bit, mildly concerned that 'comfy clothes' would be a thing of the past and stripped down. Looking at myself in the mirror I realized, all of the preparations you talked about would add some (much needed) sexy refinement. You're a man who knows what he wants. I'm pretty sure you were wearing a modern cut tuxedo shirt (that white dress shirt, the fabric was divine...mmm). Finding, taming, and polishing my inner and outer sexpot is doable. Then I thought on how incredibly satisfied you would be seeing me with my matching nails and pouty red lips... where your lips would go... where your hands could wander... my hand moved to my nipple while the other ventured towards my (your) pretty little pussy...

Wet before I even opened the email. Damn.

I laid on my comfy old navy-blue couch, put my phone on the charger, and opened your email. I made the decision to keep the vibrator in my drawer because I was buzzing enough already and Sir likes to control when I cum. Having my vibe in the mix I was liable to cum a paragraph in at this point. Practicing control at any opportunity makes sense. While everything was loading, I was casually toying with my right nipple slowly moving my legs around, hyper aware of the growing sensitivity of my pussy... and entire body.

As I'm reading about getting into position, my hand slowly drifts down to my inner thigh and makes its way to my folds. I imagine feeling all those emotions you wrote and craved to hear you say I was a Good Girl. Your Good Girl. My middle finger starts to slowly play with my clit and my other fingers relax so I can feel the rest of my hot, swollen, and soaked self.

I kept reading and hung on every word. I'm not quite sure how to explain it, but it was like every word was a new touch, a new kiss. That feeling when you are so thirsty and have that first drink of water... that instant and intense satisfaction and desire for more. That feeling of being teased and Sir stops, then that powerful, electric current of equal parts gratification, desire, and need/want.

The whole time I was reading and feeling that, my hand was matching the pace on my (your) pretty little pussy. My middle finger went from light, lazy circles to deep, intense thrusts. As I read, I needed more. I want you in my pussy as described, so I slid my middle finger inside and relished pretending it's you. I know I gasped at this point, and I remember you telling me not to cum - I wanted to.

I keep reading and keep fingering myself. Using my index finger and thumb I start to massage my clit from side to side as I pump my middle and ring fingers in and out. In and out. I sit up a little to watch myself. To look at how wet I am. And in part to make sure this is really happening - I felt so damn good it's hard to believe. I glance back over at my phone and read about how you kiss me with my juices, and I come undone.

Admittedly, at this point I dropped the phone. I needed the other hand so I could grab my tits and use my arm as leverage to slide down the couch more so my fingers could go even deeper. I switched to using my thumb on my clit to deeply, but slowly apply rhythmic pressure. My index, middle, and ringer fingers... I was sliding them so deep, and hard... it was so warm, and wet and tight. I imagined you, how your hands felt on my ass...and that damn shirt, and hearing you breathe and feeling your breath as you whisper, "That's my Good Girl. Cum for me."

I whispered into my couch, "Oh God, I'm cumming for you, Sir." and with my left hand grabbing and toying with my left nipple, and my fingers now at a deliciously blistering pace, I thought of your cologne, and came. I felt my insides pulse and twitch and quiver. My body slightly damp with sweat felt like it was taking it's first breath. Waves of warmth, relief, pleasure, exhaustion... at some point in my writhing I grabbed a nearby by pillow, I moaned and smiled into it, wishing it was you instead. I rode the waves of aftershocks and snuggled into that pillow and dozed off remembering my Sir calling me his Good Girl.

After a couple of minutes, I was alerted by my very sensitive body (specifically nipples) that I had dozed off, in the buff, with my ceiling fan on. I also found my phone, scrolled through and realized I still had a significant amount to read. I'm excited that I did not cum after the second paragraph (as I thought), but still need to work on that stamina, Sir. At this time I would like to thank you for allowing me to masturbate freely during this read, Sir.

Since I cannot reach the ceiling fan controls without a chair or step ladder (short chains, short me... I gotta get to Home Depot) I grabbed my blanket and prepared for more. I was a bit fascinated with the vibrator part. I read those sections several times and slowly played with my (your) pretty little pussy. Achieved a slight tremor by rubbing and slightly tugging... specifically when thinking about how luxuriously torturous that whole part could be. THIS is what I was talking about earlier when explaining that feeling of being teased. This, this I am interested in, Sir.

I believe it was partially because of the build up from the vibrator (in the story), but the riding crop. That also did it for me. I was reading and enjoying that glowing feeling after cumming when I started again to hang on ever word. I started to read faster, breathe faster, slide my three fingers faster and faster while my thumb flicked at my swollen and aching pussy. The pretty little pussy that is yours. Everything intensified so quickly. You. The riding crop. That damn shirt. Your voice. That cologne.

I came again for you, Sir.

After my body stopped pulsing as frequently, I took one of the most satisfyingly relaxing deep breaths of my life. I felt like a feather. I felt like a woman. Thank you, Sir.

I took another few minutes to enjoy the inner calm, and continued reading - with the fan still on, and the blanket (and pillow) available. I felt spent. It was great. I felt like I was glowing enough to light a cave and my skin felt like the softest material in the universe. From this point forward, I slowly ran my finger up and down my arm, reveled in the softness of my cotton blanket, smiled, and sighed with ease more times than I could count.

The cane on the feet seemed like something that is necessary for punishment, and something I want to avoid. Mainly because you really nailed it when I miscounted. I gathered from Victoria that there is no laughing allowed during any of this, but I will confess, when I read that there were two number 4's, I giggled a little into my pillow. I can completely see myself doing that. I know you said this was slightly recycled material from subs past, but the fact that it was in there made me very happy, Sir. It seems to be a very 'green' mistake so the nod to my inexperience... I found that to be adorable and couldn't help but giggle out of an overabundance of joy that I just could not keep completely inside. Thank you, Sir, and I will work hard to keep the giggles on the inside.

I also read the part about finding a subspace over and over. I think I've been doing something along those lines for years. Not sexually, but well, for safety. I will savor the entire writing, but this part... it struck a deeper nerve. I assure you, it's a good thing, Sir. More to occupy this busy little mind of mine. Thank you for the self-reflection trigger, Sir.

As for the ending, do you really take care of subs when things are over? With the lotions and holding? I don't doubt it at all, Sir since you are a fantastic man, but that is generally new to me. I'd like it very much, Sir.

Thank you again for sharing the story, Sir. I loved it. I understand I am not in a position to tell you what to do, but if I was, I would firmly ask for more.

PS: Hope your trip is going well!

[PERSONAL EVENT DELETED]

On 5/31/18, 9:00 PM Lynn wrote:

I'm glad everything is going well and I miss you too, Sir. Is your family all in the area?

I fly out to LA tomorrow at 5am so I've been frantically packing, which has been difficult with my new nails. I treated myself to a full set of acrylics (and a manicure for Emily) Tuesday night. They are as short as they can be, but I still feel like Edward Scissorhands - it's a blast though. Much to Emily's embarrassment I did my best impression of the Price Is Right models while in the cereal aisle the grocery store. She did the same to me when we hit up the produce. We agreed: 1) We felt like ladies 2) We need to make 'nail time' a more frequent thing :)

Also during my shopping adventures, I picked up some lipstick. Three shades to be exact, Sir. A medium dark red, a more muted red, and a nearly nude pink. My thought process is: Dark for evening, muted red for day, and pink for practice. After talking to the clerk and attempting an application at the store the "pink for practice" is needed. I tried on this looking great cherry red, but it did not go with my skin tone and I applied it like a 4-year old. Yikes. While laughs were had by all, I'm glad you weren't there for it, Sir - talk about embarrassing.

I understand the tone of this might seem like I am making a game out of things, but I very much understand this is not a game. Trying all these new things for myself is... well, weird. Very weird. Doing a little at a time and having fun while I go seems to give me a little boost when I think about it. I think I've smiled more in the last few days than I have all year. And that's saying something: My sister was in town (always stressful) AND it was the kids' last week of school (always makes me feel like an old-ass sack of shit) AND I have to pack for travel (one of my top 5 least favorite things). Even though those things were still emotionally cumbersome, you helped make them a little better.

Thank you, Sir.

On 6/1/18, 5:16 AM SIR wrote:

Your note made me smile. It's OK to have fun. I'm very happy for you. Who is Emily?

On 6/1/18, 8:11 AM Lynn wrote:

Glad I could make you smile, Sir. Emily is my daughter - sorry for not clarifying that point.

Please excuse the timestamp. 5am flights are the pits.

On 6/2/18, 11:59 AM SIR wrote:

Your messages always make me smile.

Enjoy Malibu. Don't ruin that beautiful porcelain skin in the sun. You are my Barbie now.

On 6/4/18, 12:13 AM SIR wrote:

Here's the next segment in your training. I've chosen to deliver this as a story. You will want to be alone when you read it, but you must read it before Tuesday morning. You may cum only twice, so you must learn orgasm denial by learning to edge yourself (see 'edging'). You must play with your pussy and clit to the point of orgasm, right up to the point where you start to cum, but them you must stop and not cum. {Here I included a linked to 'video28976065' on xvideos.]

Lesson 2 - Arrival.

The elevator is her safe place. As the doors close, she hopes she made it through the lobby without being seen. There's a gnawing feeling that she may never know for sure. That feeling...is it the fear of being caught? Or is it the excitement about what is about to happen? As the doors close she feels her pulse quicken, her breath shorten, her insides alight with electricity. If her night ended right now, this feeling alone would have been worth the trip. Her finger caresses the button to the 10th floor. As the doors close, she appraises the woman staring back at her from the polished doors.