Catherine and Me

By Clint

Part I - Dinner



As I look back on it now, it is a miracle that we even met. I can’t imagine what my life might be like now without her, or what kind of man I might be. I am so grateful that she came into my life and helped shape me into the man I am today. Here is the story of how it all began…..

I had been dating a woman named Lynn for a few months. She was younger, full of energy, and GREAT in bed! However, when it came to meaningful conversation, we didn’t have much in common. Lynn had a great body…tight little ass, perky breasts and a completely shaved pussy. I enjoyed sex with Lynn, but it was ordinary. I knew our relationship wasn’t going any further. Then, one day, she opened a drawer of my night stand and saw some unusual books. Exit to Eden, Please Ma’am, and Submission by Sara Wyatt.

“So what are these books you are reading?’ Lynn thumbed through them, reading a few passages here and there. Then she sighed.

“You are a lot of fun, Clint. I have really enjoyed spending time with you, but we both know fun is as far as it’s going to go.” She studied me. “I have a friend that you need to meet.”

Her words puzzled me. “You are going to set me up with one of your friends?” I couldn’t imagine why.

“Let’s just call it a friendly introduction and see what happens. Her name is Catherine and she is about your age.” Lynn smiled. “I just have a feeling you two would get along very well.”

I found out later that the feeling was much more than simple intuition. Lynn’s friend Catherine had confided intimate details of her specific needs. The need to be in charge. The little sadistic streak that made dishing out a dose of pain a huge turn-on. Catherine had told Lynn that the thought of a man submitting and turning himself over to her got her wet.

As one might expect, Catherine was a strong, independent woman, perfectly comfortable on her own. A career woman who made good money and didn’t need to depend on a man for her happiness or lifestyle. She had never settled down because she needed a man that would submit to her and respect her authority, and she was not willing to settle for less than all she wanted.

Unfortunately, the men she had met who wanted to submit to her were not much of a challenge. Wimpy or feminine, although submissive, did not excite her sexually or provide the challenge she craved. What she wanted was a big, strong, confident man who would submit to her whims AND satisfy her sexually. She wanted to be the authority figure in the relationship but for no one else to know it. But she had given up on finding such a man long ago.

Lynn called me a few days after our cryptic conversation.

“Be at Charlie's Steak House at seven-thirty tonight. There will be a reservation in your name,” she said, her voice excited but hushed. “Look for a TALL brunette woman with beautiful eyes and a voluptuous figure. You just show up, she’ll take it from there.”

“Charlie’s,” I repeated, wondering what Catherine might have in store for me. “Lynn, why are you doing this?” I still couldn’t quite understand her motives.

Again she smiled. “I like you, Clint, and I’d like to stay friends. But you and Catherine have so much more in common.”

When I walked into the restaurant the hostess seemed to be expecting me. “You must be Clint. Follow me, please.”

She led me to a private booth in the back of the restaurant. I turned the corner and, BAM, came face to face with Catherine. She was tall, almost as tall as me, and that’s saying something - I’m 6’5”. She had long legs, large and beautiful breasts… WOW! She wore a short black skirt with high black heels and a very elegant but low cut white blouse. If what she were wearing had been a Halloween costume, it would have been called “Sexy CFO.”

“Hello Clint,” she said as I hovered. “Please join me.” She slid into the booth, then indicated the seat across from her.

I eased down as she ordered wine from the hostess without any input from me. Once the girl disappeared, Catherine focused on me.

“I have been very anxious to meet you, Clint. Lynn tells me that you are a voracious reader, and that your taste in books is quite interesting.”

Stunned, I blushed. My taste in books as an opening line? What was Lynn setting me up for?

“Is this right?” Catherine prompted.

I couldn’t seem to say anything. I hadn’t been this nervous around a woman since I was in high school! I was in complete awe.

Catherine raised one eyebrow as she waited for a response. “A simple Yes Ma’am or No Ma’am will do for now.”

“Y-Y-Yes Ma’am,” I stuttered back to her.

A waitress brought the wine and poured us each a glass, then stood beside the table with her pen at the ready. “Would you like to order now?”

I had not given dinner a single thought. I was still reeling, trying to determine if I was awake or asleep. Was this a dream? Was this one of my fantasies spurred by the femdom material I’d read?

But Catherine has everything under control. “We will each have the 8 oz filet, both medium, baked potato and Caesar salad.” She didn’t hesitate or consult me.

This was unlike any blind date that I had ever been on before. ‘Who is this woman?’ I wondered.

Once the waitress had disappeared, Catherine turned to me. “I’m going to tell you why we’re here tonight Clint.” She began to explain without me ever asking a question.

“I have been searching for a VERY long time for a man willing to live the lifestyle that I require. I have tried out quite a few and just can’t seem to find the right one. I’ve shared these frustrations with Lynn over the past few years. When she came across the books in your night stand, she immediately thought of me.

“Lynn told me that you two had a lot of fun together and that the sex was good, but you really didn’t have much else in common. She described you as a handsome, sexy man.” Catherine leaned closer. “I’d have to agree.”

I blushed again.

“Clint, I need a big, strong man, an intellectual equal, but a man who is also willing to submit to me. But I want his submission to be mine and mine alone. I need a man who nobody else would ever suspect was submissive to me. An alpha male to the rest of the world, but a sex slave to me.

“I need my man to understand who is in charge, and that there will always be consequences for crossing me, disobeying me, or disappointing me. With that being said Clint, there are great rewards too. I know how to pleasure a man. I know many methods beyond simple, vanilla style sex. If you were to be with me, you will learn what an earth moving orgasm feels like and you will crave them often. What do you think so far Clint?”

“Sounds very interesting….Ma’am.” I finally got a few words out.

“Good. Let’s have a great meal tonight and get to know each other better. If the evening goes well, maybe I will take you home and see what I have to work with here. It will be something of a test for you.” She smiled.

I was so excited throughout dinner that I couldn’t think straight. We talked about a lot of things and really got to know each other. We had a great deal in common beyond kinky sexual proclivities. I shared with her my innermost fantasies. Things I have never shared with ANYONE EVER. I told her how ever since my pretty young 2nd grade teacher kept a large wooden paddle on her wall I had craved a firm hand from an authoritative female. I told her how even though I do not enjoy the pain of getting paddled or spanked, I crave the discipline.

Catherine listened, her eyes rarely leaving my face. Just before we ordered dessert, I felt her foot start touching my leg under the table. From across the booth she worked her way up to my crotch. When she found my hard and throbbing cock about to burst out of my pants, she winked. “You and I are going to get along VERY well.”

Part II - The First Night



Dinner went so well that Catherine asked me to follow her back to her place. When we arrived at her place, after we walked into the front door, she closed the door behind us pulled me to her and gave me the most passionate kiss I have ever received. She kissed me with hunger, with passion. I was so hard I thought I might cum right there in her living room. After kissing for a good 4-5 minutes, she whispered in my ear, “Go up the stairs to the 2nd room on the left. Enter the room, strip off all your clothes and get on your knees. I will be with you in a few minutes.”

I immediately turned toward the stair case to do as I was instructed.

“Stop!” she said abruptly. “You need to learn to always acknowledge me and that your instructions were clearly understood. I will never accept an excuse of not understanding my instructions clearly. Now, look me in the eyes, and if you understood my instructions clearly, say “Yes Ma’am.”

I looked into her beautiful eyes and said, “Yes Ma’am.” Then I was dismissed to the room upstairs.

I opened the door to the room and was shocked at what I saw. There was a padded table on one side of the room, a padded bench with an L-shape to it and an armless wooden chair in the center of the room. As I looked at the walls I saw various paddles, straps, leather cuffs, etc…hanging neatly on the walls. I didn’t want to spend too much time exploring and get caught still dressed.

I quickly undressed, folded my clothes neatly and placed them in the corner and got on my knees as instructed. I could hear the sound of Catherine’s high heeled shoes walking around her place on the hard wood floors. What was she doing? Had she forgotten about me? She kept me waiting for what seemed like hours but was really only minutes.

Finally, she opened the door. She was still wearing the same clothes, but from my position on my knees, I had a much different perspective. Her beautiful, long, bare legs in those high black heels and short black skirt were AMAZING! She walked closely to me and pulled my head into her low cut white blouse tightly.

“Are you ready for this?” she asked me softly.

I again was speechless.

“I asked you a question. Are you ready for this?”

“Yes Ma’am” I said with trepidation.

“Tonight I am going to introduce you to what a relationship with me might be like. I am going to introduce you to discipline and seduction. Pleasure and pain. Submission and ecstasy. We are going to spend a few hours here at my place tonight, and after, you are going to tell me if you are in our out. Once you are in, there is no turning back do you understand?”

“Yes Ma’am” I uttered.

If you are going to be with me, there will be discipline and punishment. But, there will be ecstasy like you have never experienced before. There will be unbridled, uninhibited passion….but on MY terms. Tonight, I am going to let you experience what might happen to you if and when you displease me. Then, I am going to make you cum harder than you have ever cum in your life. So let’s get started.”

She went and got the armless wooden chair, raised her already short skirt up slightly up on her legs and told me to lay across her lap. She told me that this was a position to which I should get accustomed.

I could feel the butterflies racing in my stomach. This beautiful woman was about to spank me. Suddenly I felt like I was in the second grade all over again. She raised her hand high and brought it down on my ass much harder than I anticipated. I wiggled a bit.

“Lie still,” she stated with a very serious and strict tone. She then began spanking me harder and faster and it REALLY hurt. She spanked me for a good 3-5 minutes without letting up. Then she stopped.

“I need you to get up off my lap, go over to that wall and bring me the small hairbrush paddle. Now.”

I quickly went to the wall and picked up the hairbrush and brought it back to her.

She looked up into my eyes and said, “Present it to me and ask me to paddle your ass with it. When you are being punished I am Miss Catherine or Ma’am. You are not to refer to me as anything else when you are being punished do you understand?”

“Yes, Ma’am” I uttered once again.

“Now say it. Miss Catherine, will you please paddle my ass with this paddle?”

I felt a rush of heat come over me and the butterflies continued to race in my stomach. If her hand had hurt me as badly as it did, what would this small wooden paddle feel like? I was very nervous, but knew any further delay would make it worse. “Miss Catherine, will you please paddle my ass with this paddle?”

“Why yes, Clint, I certainly will.” She then grabbed my wrist and pulled me back across her lap, locked her right leg across the back of my legs to prevent any kicking and started spanking me good with that little paddle. My ass was on fire quickly! She spanked me hard and fast and I couldn’t stand it. It really hurt me. Just as tears started to well up in my eyes, she stopped.

I really did not want to break and cry in front of her. She had me get on my knees in front of her and took my chin in her hand and looked me directly in the eyes. “This is what you can expect when you misbehave or disobey me. Do you understand?”

“Yes, Ma’am. I will not disappoint you.”

Very good, now put the paddle back on the wall and bring me the Astroglide lubricant from the shelf.”

I did as I was instructed. She poured some lube into her hand and a little on each thigh while still sitting on the armless chair. She then grabbed my already hard cock with her hand and began stroking it with the lubricant. I thought I was going to explode on the first stroke.

“Now get over my knee again and place your cock between my lubricated thighs. I am going to spank you some more. You may thrust up and down between my lubricated thighs but do NOT cum without my permission. Do you understand?”

“Yes Ma’am.” This was a real test of endurance. I had been hard since she first touched me under the table at dinner. How was I going to resist cumming now? She started to spank me again with her hand, but lighter this time and not as hard.

“Does that feel good?” she asked.

“Yes Ma’am” I replied.

“See how closely pleasure and pain can be to each other?”

“Yes Ma’am.”

“Remember…do NOT cum without my permission. If you do, I am going to beat your ass so hard you won’t sit down for a week do you understand?”

“Yes Ma’am. But I am getting very close and might lose control. Do I have your permission to cum?”

“No you do not. Stop thrusting and get off my lap.”

Catherine then moved over to the large padded table. I was on my knees in front of her and she slowly removed her black thong panties from under her short black skirt. She flipped them off to the other side of the room and sat up onto the table.

“Now it is time for you to give me some pleasure. Stay on your knees and come over her between my thighs and lick my pussy. See how wet disciplining your ass makes me?”

I dove into her sweet, shaved pussy. I licked her the best I could just wanting to please her. She moaned and rocked and held my head forcing me into her harder. Then, after about 10 minutes of worshipping her beautiful sex, she shuddered and came hard. She screamed out and shook all over. It was amazing. I thought I was going to cum just feeling her shudder and cry out. When she came back down again, she told me that I had done a good job.

Shen then instructed me to lie on the table on my back with my knees up and my feel flat on the table. She went over to the shelf again and grabbed more lubricant, a rubber glove, and a toy of some sort. She took off her blouse, skirt, and bra at this point only wearing those high black heels. She was beautiful. I wanted to be inside her so badly that I couldn’t stand it. I went to embrace her and she pushed me away.

“Not tonight,” she said. “I am going to pleasure you another way.”

Again I was excited…but still nervous. She put the rubber glove on her left hand and put more lubricant into her right hand. She began slowly rubbing my cock with the lubricant and her right hand. She then put lubricant onto her rubber glove. She slowly entered my ass with her left hand as she stroked with her right. I had never been harder in my life!

She was stroking and caressing me SO slowly as she entered me. She began rubbing my prostate while she stroked. She did this for a while, somehow controlling my cock and not allowing me to release. She then took off her rubber glove and grabbed the toy she had brought over. She slid the lubricated toy into my ass very slowly, still stroking my cock with her right hand. She pulled me closer to the edge of the table and placed my cock between her ample breasts. I began thrusting up and down between her tits. They were so beautiful. I was so hard. I just wanted to cum so badly.

“Remember, you must have my permission to cum.” She reminded me. Then, she pulled me out from between her breasts and took my cock into her mouth. She began to slowly lick up and down the shaft of my penis stroking me slowly with her right hand still holding the toy in my ass. I could feel a tingling sensation beginning to build in my lower legs and working their way up to my groin. She sucked hungrily at my cock, stroking me with her hand, sucking, still entering me with the toy…this was a sensation like no other. I was light headed, I couldn’t hold back any longer,

“PLEASE MISS CATHERINE MAY I CUM?” I pleaded to her.

She took her mouth off my cock looked into my eyes and said, “Yes Clint, you may cum…cum big for me.”

I then came harder than I have ever cum before. I almost hit the ceiling with the strong spurts that came out of me. She continued to stroke me and milk out every last drop. I was spent. I felt like I needed to be peeled off the ceiling.

She then laid down next to me, naked and I put my arms around her. She looked up at me and said, “So are you in or out?”

What had this woman done to me? Where has she been all my life? “I am all IN” I stated. And so it began.

Part III - The First Punishment



My relationship with Catherine had gotten off to a great start. I was eager for direction and female authority so it was very easy at first. We had continued to build on our first night together and I experienced more ecstasy and pleasure in our first couple of months together than I had in my entire life. She was a woman who knew things. I don’t know how she knew them, but I was glad she did. We had experienced great sex on many occasions in our first two months together and it seemed that as long as I obeyed her and pleased her, there was no end to the rewards that came with it. I longed for her pussy each and every day. Just the thought of her made me hard no matter where I was. I wanted her all the time, and I was happy for any attention that she was willing to give me. That was until the first time I disobeyed.

One of Catherine’s rules was that when I was on a business trip, I was to call between 8:00-8:30 PM every night without exception. If I had to step out of a business dinner, then I would do so. If I was back in my hotel room, then I called from there. No matter where I was or what I was doing, I was to call between 8-8:30 Eastern Time.

I was very good about this during my first few months. But then, we had a big company meeting in Las Vegas, four nights there total. I took careful note of the three hour time difference between Vegas and Florida, and on the first night, I called as required, no problem. But I hadn’t been to Vegas in a while, and the allure of Sin City got to me. I hadn’t experienced Catherine’s discipline for months now, and what that might mean had faded, so I conveniently forgot the rules.

The second night, I managed a call at six pm, but by then it was already nine pm in Florida. To me the difference felt minor, but Catherine made me well aware that I had broken the rule.

The third night, things really got away from me. I went to a topless bar (another rule of Catherine’s broken) with some of my work friends and by the time we got in, it was so late I decided not to call at all.

The last night, I got a little nervous about going home, so I made sure I called, offering up untrue excuses for the previous two failures. Catherine didn’t question me, or even scold me.

The next day I breezed to the airport, confident I was off the hook. I ate a bagel, sipped some coffee, and read the paper. After boarding I was just about to turn off my smart phone when a text came in from Catherine. A photo of her small wooden hairbrush accompanied the question: Before or After?

Just seeing the photo of that paddle brought butterflies back to my stomach. I don’t understand, before or after what? I texted back.

Do you want your punishment before or after you pleasure me with your tongue? I am concerned that you may not be able to perform after I get through with you this time.

Uh-oh. I typed out, Before. And then had to turn my phone off for a long flight.

When we landed in Florida, I had several texts from Catherine, sent over the course of the last four hours.

Prepare yourself.

Come to my place immediately from the airport.

Let yourself in, proceed to the punishment room, strip and get on your knees just like the night we met.


The regret began, fueled by fear. This beautiful woman, this sexual predator that I was now in so deep with is upset with me. What’s going to happen now? What’s wrong with me? Why did I go to that topless bar? She doesn’t even know about that! But why would I ever need anything more than what I now have?

I sped to her place, and I let myself in. I prepared as instructed. Naked, vulnerable, scared, excited - I found myself in the same state as I had been three months ago. I heard her high heels in the hallway, and when she entered, saw that she was dressed exactly the same as the night we met. Short black skirt, bare legs, high black heels and that low cut white blouse. This time no bra.

She took my chin between her fingers and thumb looked down into my eyes. “Do you remember what I told you on the night we met?”

“Yes Ma’am.”

“Now you have broken my rules, disobeyed me, and lied to me. Is that correct?”

“Um...No, Ma’am. I didn’t...lie.” I was lying about lying!

Catherine shook her head. “Don’t make it worse. I saw some of your colleagues photos online. I know you were at a strip club.”

Totally busted! I hung my head. “Yes Ma’am.”

“Now you are going to learn how serious I am about your obedience. I told you that the rewards and pleasures of being with me were vast, didn’t I?”

“Yes, Ma’am.”

“Have you not had more pleasure with me over the last three months than you’ve had the rest of your life?”

“Yes, Ma’am, I have.”

“Well, boys will be boys I guess. And boys need discipline. Go get the hairbrush paddle off the wall, bring it to me and ask me to punish you for disobeying me.”

I jumped up off my knees, fetched the paddle and brought it to her. “Please punish me Miss Catherine for disobeying to you.”

“And how do you think I should punish you, Clint?”

“Hard, Ma’am.”

“Very good then. Over my knee.”

There was no hand warm up this time. No easing into it. No, this was to send a message. She began paddling me with that little wooden paddle without mercy. Each lick sounded like a gun going off and my ass was on fire!

“Please, Ma’am, stop! I am so sorry,” I begged.

“We are just getting started young man, save your breath.” She wrapped her right leg over and across the back of my legs and spanked me hard. It hurt so bad that tears welled up in my eyes.

Five minutes later she paused. “Get up and go stick your nose in that corner until I call you out, do you understand me?”

“Yes, Ma’am.” I struggled upright and stumbled to the corner, again reduced to a child from the second grade.

As I trembled there, Catherine came up behind me and rubbed her breasts against my back. She reached around me and grabbed my cock and began to stroke it.

“Isn’t it a shame that we aren’t locked in an embrace in my bed with my legs wrapped around you right now?” she whispered.

More tears welled, only this time from more than pain. Had I ruined this amazing thing we had going together?

She pulled away and took her blouse off. Just her skirt and heels now. “Go lie face down on the padded table. I’m going to strap you now for going to a topless bar without my permission.”

Permission? It had never occurred to me she might have given me permission. If I had only asked!

Trying to show my compliance, I raced to the table and lie down. She took the belt out of my pants. “You’re getting fifty licks with this belt. Your own belt!” She held it out for emphasis. “If you move, or lift your ankles up off this bench even slightly, you’re getting three hard licks with the big school paddle. Do you understand?”

“Yes, Ma’am.”

With that, she doubled over the belt, drew it back far and brought it down hard on my ass.

CRACK! The sound echoed in the room.

CRACK! Each lick seemed harder than the last.

I lost count, but somewhere around thirty, a reaction pulled my ankles up off the table. She stopped swinging, laid the belt on the table next to me, then picked up the large wooden paddle, and smacked me hard hard three times. The paddle really hurt!

“Do NOT lift your legs off the table again,” She reminded, then resumed with the belt. I did not move for the remaining twenty. Each lick of that belt sent fire through my ass, but I took it.

“Get up.”

My knees were weak and my legs shaking as I watcher her take the large, wooden school paddle across the room. She placed it on the wall at about my eye level.

“Come hold this paddle in place. Look at it and think about all the fun we have had together so far. Think about the rules that you broke and decide whether or not it was worth it. You must understand that lying is the most severe offense. Do not ever lie to me again. I am going to go sit back on my chair and wait for you. When you are ready to be punished, come ask me to paddle you for lying to me. Do you understand?”

“Yes, Ma’am.” I pressed my hands against the paddle holding it to the wall. It was a scary looking .paddle, much like the one my second grade teacher had in her classroom. I thought about the rules I broke and how much I loved being with this woman. I knew I deserved to be punished. When I was ready to get it over with, I took the paddle from the wall and walked over to Miss Catherine.

She was sitting in that armless chair, topless, with those long, shaply legs crossed. She was so beautiful, yet so strict.

“Miss Catherine.” I offered her the paddle. “Will you please paddle my ass for lying to you?”

“Yes, I will Clint. Go place your hands flat against the wall. Bend over at the waist and stick your ass out. Push up on your toes. You are getting ten very hard licks. The next time you lie to me it will be twenty, and the third time we are finished. Do you understand me?”

Finished? My stomach flopped. No matter what, I couldn’t let that happen.

My delay made Catherine impatient. “Do you understand me?”

“Yes, Ma’am.”

“Up on your toes. Prepare yourself. Do not come down off your toes and do not remove your hands from the wall,” she commanded.

The first lick hit me and hit me hard.

TWHACK! I cringed.

THWACK! I groaned.

Ten hard licks came down on my ass and tears came out of my eyes. I couldn’t hold them back any longer. After the tenth and final blow, Catherine turned me around and hugged me.

“The reason I do this is so that all can be forgiven and not linger. You are now forgiven for your behavior and it is behind us,” she said. “Go to my bedroom and shower. Remain naked and get onto my bed lying on your stomach.”

My ass was on fire as I showered, the hot water even hotter as it washed over my punished skin. I toweled off carefully, then crawled onto the bed.

Catherine came in and sat beside me. “I’m sorry I had to punish you so harshly, but you brought it upon yourself.” She rubbed lotion into my throbbing ass, rubbing and kneading for a long while. Finally, she turned me over and got on top of me, completely naked.

“I must admit that punishing you and receiving your submission turned me on.” She gave me a passionate kiss then took my hand and placed my fingers between her legs. “Can you feel how hot and wet I am from it?”

“I can,” I breathed.

“So fuck me like you haven’t seen me all week…………..”

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