Pleasuring Ms. E.

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Please note all characters in this story are fictitious and adults (over 18).

Story Summary:

Mike is an amateur erotic author. He has written over 50 stories and shared them online via several different cloud applications. Mike enjoys writing stories that closely parallel events he's experienced in real life. Obviously, Mike changes the story enough to protect his identity and those of his story protagonists.

Mike is particularly fascinated by oral sex. Careful readers have been able to deduce his interests and sometimes comment accordingly. Sometimes, a reader even engages Mike over email to share their thoughts on his writings. Most hint that they suspect that Mike's own experiences might be shaping his story lines.

One day, an email arrives that piques Mike interest. This is the story of that interaction.

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Mysterious Ms. E.

It was 2 p.m. on a non-descript workday. I had a lull in my schedule, so I decided to check on my personal emails to catch up. As I scanned through the subject lines of my unread emails one caught my eye instantly.

"You make me wet," was all the subject line said.

I quickly looked at the sender address and realized it was feedback from one of sights I use to publish my stories.

"Well, that's interesting," I whispered to myself and opened the email.

When I opened the email, I instantly realized there was a picture that was unsafe for work and closed it immediately, before anyone else saw it. I stood up and walked across my office to close the door. I walked back to my desk and re-opened the email. Inside the message body were a single image and some text.

The image was a woman standing in a pair of boots and nothing else. She was standing over her iPhone so that the camera was pointing up her legs with her bare ass and pussy centered in the field of view. Her thighs and hips were shapely but full, she looked to be in her mid-forties (about the same age as me). She was completely shaved which provided me with an unobstructed view of her womanhood.

Under the photo, there was a single sentence that read, "I think you and I both know you want to be underneath me."

"Jesus," I whispered to myself, as I looked at the photo over and over.

"This woman has discovered my fixation," I continued, "I didn't think I was being that obvious."

I was unsure how to respond.

"Is this a prank? Is she real?" I wondered to myself.

I looked at the sender's email address. It read, "Ms.E@popularfreemail.com".

(popularfreemail is used to protect the innocent).

I stared again at the picture. The mystery woman had a voluptuous body with an ample ass that made my mouth water. I loved women with full hips and curves that I could explore like winding roads in the countryside. My mind quickly propelled my thoughts to scenes of me burying my face in those curves and providing oral pleasure to the beautiful and assertive owner.

Crafting a Response

I had no appointments for the rest of the afternoon. This allowed me to focus on my response to the woman who had clearly been reading between the lines of my erotic stories. My hands were shaking as I started drafting my response.

"Hello Ms. E," I started, figuring I should respond to her using her email name.

Well, the easy part was done, now I needed to figure out a response that might cause our interaction to grow into something more. If I was too direct, I was worried she'd think me a pervert. However, if I was too aloof, I might not ever get a reply. I decided to keep it simple and go with my instincts.

"You are very clever to have discovered my oral fixation," I wrote, "I would very much enjoy being underneath you."

I re-read my response a half-dozen times. It was direct and honest. I hoped it would get a response. I thought long and hard about sending a photo in my reply, but I was worried that this could be a prank and I might be discovered if I disclosed a face picture. I knew that sending a cock picture would likely not get the response I wanted.

After a few more re-reads, I pressed send. The email closed and I was back looking at my inbox.

"Your move Ms. E," I said under my breath.

I closed my personal emails and tried to bring my mental focus back to work. Every 30 minutes, I found myself closing my office door to look at Ms. E's picture over and over. I even loaded it into Apple preview so I could zoom in. I was in trouble; this woman had gotten into my brain and triggered my deepest fixation. All I could think about was licking her from bottom to top.

The rest of the day at the office was uneventful. I drove home, ate dinner, finished up some emails and work. Around 8 p.m., I changed to comfortable clothes and opened a bottle of wine to relax for the evening.

Evenings are usually warm in spring in the south, but this evening was particularly warm and humid. I kicked off my flip flops and carried my iPad out to the pool to browse the internet while I sipped on my cabernet. I found my favorite chair and sprawled out, making myself comfortable in my swim trunks and t-shirt.

After a second glass of cab, my mind started to wander back to Ms. E's email. Even though I lived alone, I looked around the pool area and then opened her email from earlier today.

"Jesus," I said, under my breath, as I viewed her picture, "I could eat that all day long."

I fantasized about being on my back looking up with the same view her iPhone had. In my fantasy, I pictured Ms. E looking down at me with a mischievous grin as she waited to trap her prey between her beautiful ass cheeks. I reached down and stroked my throbbing cock through my swim trunks as I slipped away into my fantasy.

"Beg for it," Ms. E. said as she looked down at me lying on my back below her.

"Please Mistress, may I eat your pussy and ass," I begged, sounding desperate and pathetic.

I had never been with a dominant woman before. Nor had I ever called a woman "Mistress". But this was a fantasy, so I was letting myself imagine giving power away to this woman who sent me the erotic email. I was getting turned on thinking about the scenario. More turned on that I expected myself to be.

"Good boy," Ms. E. said, in her low sexy voice, "are you going to let your Mistress fuck your face until she cums in your mouth?"

"Please Mistress," I moaned, "I want to taste your juices."

I was so turned on that I forgave myself for the corny dialogue of my fantasy. I had no time to think like Earnest Hemingway, I just wanted to get off while fantasizing about having this woman face sit me to orgasm.

I pulled off my swim trunks to give myself unfettered access to my 7" cock. This stranger had triggered my libido more than it had been in years. I was jacking off in my back yard while staring at her photo. It was a good thing my yard was private.

Ms. E. lowered herself on to my willing face. I watched as her beautiful ass and pussy started to encompass my entire field of view. Soon she was just inches away from my face, my mouth was open ready to receive her and deliver the pleasure she deserved.

Her aroma was intoxicating, I couldn't wait to taste her pussy and ass. Ms. E. was facing my feet so I wondered if I she would feed me her ass or her pussy first. Either way, I was ready to serve.

"Time to pleasure your Mistress, boy," Ms. E. moaned, "I am so ready to ride your face."

Ms. E. landed on my face. My tongue went immediately for her wet pussy and my nose was buried between the two beautiful orbs of her ass. I was drowning in lust as this stranger was feeding my deepest fixation. I knew that this was going to be an epic face sitting that ended with Ms. E. ridding me hard until she came in my mouth.

"Oh, you are a good boy," Ms. E. growled as she started sliding back and forth across my face and tongue.

"Breathe when you can, baby," Ms. E. laughed, "You're here to deliver pleasure to your Mistress."

My cock was rock hard as Ms. E. slid herself back and forth across my helpless face. All I could do was keep my tongue extended and let her use it as she needed. I reached up to caress the ample globes of her ass, moaning as I lavished this hot woman with worship.

"Look how hard you are boy," Ms. E. hissed, "you love being underneath your Mistress don't you."

"Mmhmm," I moaned into her crotch from below.

Ms. E. slid forward on my face forcing my tongue into the crack of her ass. I felt my tongue sliding back and forth across her tight little pucker.

"That's it boy, Mistress loves your tongue in her crack," Ms. E. moaned, "put that tongue inside me where it belongs."

She stopped so I could work my tongue into her ass. I formed my tongue to a hard point and worked it into her tight hole. I felt a sudden tightness in my balls as I started blowing thick ropes of semen onto my t-shirt.

"Of fuck," I moaned as I unloaded onto my t-shirt.

Rope after rope of thick semen launched from my throbbing cock. As soon as I fantasized about eating Ms. E.'s ass, it pushed me over the edge. My legs and body trembled as my orgasm continued. At that moment, all I cared about was finishing myself off. My hand was covered in cum and it was making a wet sloshing sound as I continued to stroke myself in my back yard. After a few final spurts, I was done. Breathless and somewhat shocked at my behavior, I jumped up from my chair and went into the house to clean myself up.

"She's turning me into a pervert," I laughed to myself as I threw my t-shirt into the bathtub and jumped into the shower to wash myself off.

I dried myself off and used the towel to wrap myself, then I wandered back out to the pool to grab my wine and iPad. Once I was back inside, I sat down at my office desk and opened my emails to catch up before I turned in for the evening. After reading through all my work emails, I noticed I had 2 new emails in my personal account. I opened that account and saw another subject line that stood out.

"Suck on this," was the subject line.

It was another note from Ms. E., I couldn't wait to open it. I clicked on the link and up popped another image. This time it was a close-up of Ms. E.'s perfect pink pussy. She was holding her labia open to expose her clitoris. She had also pulled the skin on her clitoral shaft back to expose the naked head of her clit. Her fingers and pussy glistened with wetness. Her pubic bone was decorated with a thin landing strip of blonde hair.

"Holy fuck," I moaned in a guttural tone, as I pulled my towel off exposing my cock again.

Underneath the pic was a single sentence, "Don't stop until I pull you off."

Ms. E.'s legs were spread wide, and she was reclining in a chair so I could see all her womanhood including the little pink pucker of her ass. I imagined myself on my knees in front of my Mistress serving her submissively. I needed to pleasure her with my tongue and mouth. My brain was just wired that way, I had no choice in the matter.

My hard cock was again in my hand, and I was stroking it instinctively. Even though I had cum just 20 minutes earlier, I was so turned on that I needed to cum again. It was as if this woman, who I had never met, was inside my head sending me messages that reinforced the depraved fixation that I kept secret to most women I had a chance to sleep with.

Ms. E. knew that I needed to pleasure a woman with my mouth. I hadn't ever considered being submissive to an aggressive woman, but with Ms. E., I wasn't just open to the idea, I craved it. I felt my mouth hanging open as I pawed at my cock like a fiend. I was bringing myself to another orgasm while staring at a pussy picture of a woman I had never met.

My office was filled with the sound of my hand slapping up and down my throbbing cock. My office was dark except for the glow from my computer monitor. I wondered if the shades on my street-facing windows were closed, but I didn't stop to look. I was too deep into my own freakish lust to care. Certainly, I hoped that passing neighbors would look in and see a large image of a vagina illuminating my bobbing silhouette as I jacked myself into oblivion, but I didn't care, I just wanted to get off.

"Fuck, I have to meet this Mistress," I moaned, "I want to be her slave."

I imagined myself being kept naked by my mistress. I'd be at her beck and call do eat pussy and ass on-demand. I loved the idea of giving up control to this aggressive vixen, I didn't just want to meet her, I had to meet her.

"Oh Gawd!" I moaned as I started spraying semen all over my office floor.

My body rocked and spasm as I emptied what little semen was left in my balls. My cock was starting to chafe from my overzealous masturbation. I hadn't been this obsessed with my cock since I was a teenager. As my orgasm subsided, I sat in my office chair covered in semen, shaking, and breathing heavily. I continued to stare at the image on my large computer screen.

Once I was out of my trance, I headed back to the shower to clean myself up. I then returned to the office to clean up the mess I made on the chair and floor. After I cleaned up the mess, I looked up at the screen and realized I had left Ms. E.'s image up and enlarged on the screen.

Mike Requests a Meeting with Mistress E.

With the office cleaned of the evidence of my perversion, I sat down at my desk wrapped only in my towel and worked to craft a response to my new "Mistress". Even though I had jacked myself twice to her images, I was still super horny and filled with desire. I had to meet this woman and see what happened. I was unattached, it would be two consenting adults exploring each other's needs and fetishes.

I hit the reply button and watched the response page load in my browser. I needed to say something compelling without appearing desperate. I wanted to meet this assertive stranger and let her control me for her pleasure. I didn't just want it, I needed it.

I started out my email with an obsequious opening.

"Mistress E.", I started.

I needed earn my request to meet in person. I needed to explain to her the benefits of meeting with me. I also needed to ensure that she felt safe so the upside or meeting me outweighed the potential risk.

"I am a discreet professional who is respected in my community. Nobody would ever suspect that I have a fixation that you seem to have discovered," I continued.

I want to express how desirable she was and how much I needed to be of service to her. I thought for a while and then drafted a sentence.

"I have been so mesmerized by your photos and emails that I can't keep my hands off myself. I keep fantasizing about orally pleasing you in any way you can imagine. I'm finding it hard to be productive at work or concentrate on anything else," I typed.

After re-reading the sentence, I felt that it expressed my desire honestly without sounding like a perverted freak. Now I need to make my ask.

"I have no idea where you are, but I would travel at my expense to meet you so I could make my fantasies about you a reality. My zipcode is 38111, I'm in the Memphis area. If you are willing, I would love a chance to meet you and submit to you as my Mistress," I drafted.

I sat back to read the draft email as follows:

"Mistress E.,

I am a discreet professional who is respected in my community. Nobody would ever suspect that I have a fixation that you seem to have discovered.

I have been so mesmerized by your photos and emails that I can't keep my hands off myself. I keep fantasizing about orally pleasing you in any way you can imagine. I'm finding it hard to be productive at work or concentrate on anything else.

I have no idea where you are, but I would travel at my expense to meet you so I could make my fantasies about you a reality. My zip code is 38111, I'm in the Memphis area. If you are willing, I would love a chance to meet you and submit to you as my Mistress."

After reading the draft, I considered sending a cock pic. I wanted her to see how raw and red my cock was after I had pulverized myself in tribute to her photos. My better judgement prevailed, and I decided to let my words do the talking.

I re-read the body of the email one more time and then pressed send.

Never had I engaged a strange woman I never met over email. Never had I exposed my deepest desire. Never had I told her I would willingly submit to her and essentially make myself her sex slave willing to worship every part of her body. I was buzzing with excitement and lust. Now I just needed to wait for a response.

Waiting for Ms. E.'s Reply

The next day I was back at work. I had a full schedule that took me from 7 a.m. until nearly 3 p.m. Once back at my desk, I started digging through the pile of emails. Around 5:30 p.m. the office was quieting down, and I had nearly completed all my work for the day. After closing my office door, I opened my personal email account hoping to see a response from Ms. E.

"Don't forget these...", read the subject line of one of the emails.

The sender was once again Ms. E. I clicked on the link and watched as the email opened in front of me. There on my work screen was a nice pair of tits with light pink areolas and erect nipples. Between them was a deep cleavage with slightly tanned skin that looks like the color of a perfectly roasted marshmallow against the white breast skin that had been covered by her swimsuit.

Ms. E.'s nipples were at least a quarter inch long, probably more. Her breasts were full and pendulous, hanging nicely on her frame indicating that they were clearly natural. She was cupping each breast in her hand as if she was offering them up for worship. My lust was again triggered. I couldn't wait to suckle on those beautiful nipples and flick my tongue over the tip hoping to stimulate my Mistress.

Underneath the photo were a few paragraphs this time instead of a sentence.

"Slave,

I understand you are offering yourself to me to use for my pleasure. I am near Jonesboro which should be about 1 hour away from you by car. If you wish to serve me this weekend, I need you to be here Friday evening no later than 8 p.m. and you will stay until Sunday at 3 p.m.

Meet me at Cregeen's Irish Pub at 8 p.m. Friday. I will be in alone in a booth waiting for you. You will address Ms. E. in public, and Mistress in private. If I like what I see, I will take you back to my place for your audition.

In Dominance,

Mistress E."

I was breathing rapidly, and my cock was rock hard. Ms. E. had agreed to meet. Not only for a night, but for an entire weekend. I couldn't imagine how exciting it would be to be under her control for almost 48 wonderful hours. How incredible that she was only an hour away by car. I'd be in a town where nobody knew me with a woman I had never met. It was incredibly exciting.

I quickly hit reply and waited to enter my response.

"Mistress,

Thank you for your reply. I am anxious to meet you on Friday evening. I will be there at 8 p.m. sharp.

See you then,

Slave"

I couldn't believe I was referring to myself as slave in my response to this woman.

"What is she's crazy?" I thought.

"What if she isn't even a woman?" I wondered.

My lust overcame my inhibitions and I hit send.

I sat back in my chair and looked around through my office windows out into the rest of the office. I wondered if my face was flush with excitement. I was glad there were only a few folks remaining in the office. Friday night was must 24 hours away. At this time tomorrow, I'd be packing up to leave for the weekend.

"Bing," I heard my computer indicate a new email.

I looked down to see a reply from Ms. E. already. The subject was empty. I opened the email and found the following message: