The Education of Cassie

This is a work of fiction. Names, characters, businesses, places, merchandise, companies, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental. All characters in sexual situations are 18 years or older.

This story contains watersports and anal sex.

This is a follow-on to "The Diary of Mistress X." Thank you for your comments to that story. It would be helpful to read first, but this story can also be read by itself.

Mistress SWP

A colorful striped wind sock fluttered in the humid breeze coming off the Gulf of Mexico. There were ocean freighters parked far offshore on still waters under sun drenched skies and wispy clouds. I stepped off the boardwalk from Mistress Gwen's five acre oceanfront estate onto Longboat Key's wide expanse of beach. The hot, powdery white sand covered my flip flops as I stepped into it. There were four chaise lounges with thick cushions, light grey with navy blue piping, already set up by Rita about ten yards from the water, low rise tables set up between them.

I took off my sheer cover-up and laid it across one of the unoccupied chairs and started rubbing in sunscreen, starting with my arms and legs. I spread the cool, thick lotion across my legs with broad strokes of my hand, feeling virtually no stubble left over from the shave I did during my morning shower. I extended my legs out onto the end of the chaise and wiggled my toes, rubbing off some of the sand that was wedged between them. I made sure to get the sunscreen under my white bikini bottom so I wouldn't burn on the bare skin bordering the fabric.

There wasn't anybody else nearby so I untied the back of my bikini top and rubbed sunscreen on my back as best as I could, then my breasts. It felt sensual to massage the lotion into my breasts, the soft tissue yielding to my touch. I worked sunscreen into the base of my nipples, soothing the tender flesh that was so recently ravaged by Mistress Gwen's alligator clips. I shuddered at the memory of her fastening the clips on my nipples while I was blindfolded, a searing heat far beyond that of the midday sun. I refastened my bikini top, reclined on the chaise, and put on my sunglasses to cut the reflected glare coming off the water. I picked up the trashy novel that I brought, but after two paragraphs I lost interest. Nothing in fiction could replicate what I had experienced the last two days.

The last two days here had redefined my life. My second career as a fledgling newspaper reporter for an underground newspaper in New Orleans brought me here, pursuing a story on Mistress X, a Domme who was famous in the Big Easy in the 80's and had retired here in Florida.

Mistress X was a part of the urban legend of New Orleans. She was reputed to have an almost magical way with women; beautiful, alluring, controlling being the most common adjectives used to describe her. I'd just finished a piece on a homeless encampment near our office that caught the eye of my editor. He was hot for another gritty account and thought pursing a legendary Domme would make for a great second act. I went to Longboat key in search of Mistress X, with the trail ending at the home of Guinevere ("Gwen") Bouchaine.

Here's what I didn't count on - falling under her spell. I fell hard. I had all of the warning signs (single, impressionable, sensual, at times deferential, almost submissive), though I didn't realize it, so I turned out to be the hapless fly and she was the cunning spider. I had spent five days in her web - so fine, almost invisible, yet strong enough to bind me. After I submitted to her, she admitted she was Mistress X.

I hadn't seen much of the world, truth be told I was naïve, and mixing a woman with her considerable talents and experience with my naivete made it more than easy for her to ensnare me. I learned what it was like to surrender control to a woman who was an expert at manipulating human emotions. The heights and depths she took me to were breathtaking and the transitions were abrupt, feeling extreme pleasure one moment and plummeting to searing pain the next. For me, the pleasure was the experience of feeling everything so vibrantly in the skilled hands of a beautiful woman.

Gwen had debunked my preconceived notions about domination and submission. I thought it was all about the sex. I couldn't have been more wrong. The titillating part about domination and submission was the transfer of control, the clash of human ego, and the exploitation of the desire to please. The sex was simply an outfall of this mental tug of war, though truth be told the sex was hot and nasty.

I laughed at myself, and the grand designs I had to be a world famous investigative reporter. On only my second project, I was already ensnared by the person I was investigating, and was seriously contemplating giving everything up so I could be with her.

Could I see myself living here with Gwen, Soo and Rita the rest of my life? To live in a five acre estate on the Gulf under the control of a woman of immense power and uncompromising beauty? Was that a trick question?

I could see myself living here, but I wouldn't leave New Orleans, my friends and my jobs just for a comfortable lifestyle. I was young, and there was so much of the world to be explored and understood. I wasn't sure I was ready to dial back my lifestyle to the free and easy environment here. My God, I was sitting on a white sand beach staring out onto the Gulf of Mexico on a chaise lounge that was worth more than my car.

But I always told myself that I would leave New Orleans for love. I said it to myself a million times when I was at college at Northwestern, dating women from all over the country. But a sixty-three year old woman? At thirty, I was less than half her age. Did I love her? I'd only known her for five days. Five of the most amazing days of my life, but only five days. Was it love at first sight?

I had to answer that question in the affirmative. I took myself back to the little car "accident" I had in front of her gate when Gwen intervened to save me from causing much worse damage. She pushed me back in the driver's seat and slammed my car into "Park." After doing so, she looked into my eyes for an instant, and in that instant I remember seeing her piercing emerald green eyes peering into the inner recesses of my soul. Over the next few days she demonstrated an uncanny sense of knowing what I was thinking, sometimes before I thought of it myself.

My thoughts wandered to how Gwen had already changed my life. I had never been with a woman with such a force of will. Through the vehicle of submission she was able to take me past the outer boundaries of my experience, physically and emotionally. I wept, I screamed with pleasure and experienced the full spectrum of emotions in between. The sex was breathtaking, insane, erotic, depraved and memorable. I will never forget what I learned about how to please another woman. Gwen was the master and I was the student.

So did I love her? Yes, I did. She understood me and completed me physically and emotionally. I had never wanted a person as much.

But the real question was if she loved me. I wasn't certain, because she hadn't declared her love for me. Now granted, I never told her whether I loved her, but I knew in my heart that I did.

She lived in a comfortable cocoon on her estate, with its high walls and its impressive gate. Emotionally, she had spent decades building a wall between her and the rest of the world. She let very few people into her world, and I apparently was one of the chosen few. But being let in wasn't enough for me. If I was to give up the life I'd built in New Orleans, it would have to be for love.

More basic questions haunted me. Could I accept love, but not in the traditional monogamistic sense? Rita had been living with Gwen for over twenty years, and Soo had been her submissive for two years. I would be the newcomer to a four-way relationship. I hadn't yet managed a successful relationship with one woman. Could I manage it with three? Did Gwen love Rita and Soo? Then a bit of panic entered my mind. I'd never asked her if she was married, and she never said one way of the other. Was she?

I was pondering my questions while drifting off to sleep under the hot sun, and didn't realize that Gwen had taken a seat in the chaise next to mine. Through a dreamy haze I suddenly smelled roses. It was Gwen's natural scent, at least when it came to me. Freshly cut, ruby red roses. The color of Judy Garland's lips.

Her voice rang out above the soothing sound of the gentle surf. "What's troubling you Cassie?"

Her question interrupted my reverie, and jarred me into the present.

"Gwen ... I didn't realize you were here." She was wearing a one piece bathing suit with a floral design, cut high on the hips with a plunging neckline. Her hair was up and she wasn't wearing any make-up. She looked stunning, nevertheless.

"I had the sense that something was on your mind. I'm one to address issues right away and head on. Tell me what's on your mind."

I lowered my sunglasses. "Are you married? I don't see a wedding ring on your finger." I blurted it out without thinking. I felt like an insensitive dolt. I was glad she took my question in stride.

"Gracious no. I've never married. What would give you that idea?"

"Rita's been with you forever, and Soo gave up her medical career to live with you."

"As I told you before, I have an unusual relationship with Rita. She's my companion, but she's not my lover."

"So do you love her?"

She had a serious look on her face. She probably already knew where this conversation was going.

"I do, but more as a sister than as a wife. Rita and I aren't intimate. She's more like my companion. On occasion I may invite her to watch, but Rita has had her own relationships over the years. At this time, she doesn't have a girlfriend. Does that answer your question?"

"I think it does. Now what about ..."

"Soo? I do love Soo, and in the straight world, the vanilla world, our love is more like the love between spouses. We have a deep affection and mutual respect for one another. It's just in a different context. You've been able to experience a part of that kind of relationship. Do you think a dominant and submissive can love each other as deeply as a married couple?"

I wasn't prepared for Gwen to turn the tables on me. I thought about the last few days and the interactions I witnessed between Gwen and Soo. Yes, they treated each other with as much love and respect as I'd seen in any married couple. She was making her point.

"Yes, Gwen, I believe there can be love in a dominant/submissive relationship. I think you and Soo are proof of that."

"Then I think you've answered your own question. The question you're really meaning to ask is whether I love you."

As always, Gwen knew what was on my mind. "It is. I know that you want me to stay, but I've got a whole life I'd be leaving behind in New Orleans."

"Cassie, it's been less than a week. I have the same feelings towards you that I have for Soo. But is it love? I'm not sure yet. We've had so little time together, and in that time we've made such an instant and profound connection. I think I know you. But what you're struggling with is your decision. I can tell you that I already have a deep affection for you that I'm sure will turn into a lasting love, but it would be unfair for me to tell you that I'm already in love with you."

"Can you be in love with more than one person?"

"I know I can. I've been in this situation before." She leaned over and took my hands in hers. She made sure there was eye contact. "You're here for a couple more days. Let me show you more about my lifestyle. It'll help you make your decision."

Then she kissed me. I closed my eyes. I smelled the salt air and her indelible fragrance of roses. I felt her hand, cradling my head, as her lips moved in concert with mine. It was going to be a difficult decision.

* * *

After Gwen and I returned from the beach, we went into the kitchen and saw Soo busy preparing lunch, wearing a sheer black cover-up and black teeny bikini underneath. Soo was Gwen's submissive, a medical doctor by training, with a charming British accent that reflected her upbringing in Hong Kong. Soo was only a bit more than five foot tall, but her diminutive frame packed firm, pert breasts, a narrow waist and flaring hips. She turned away from the stove when we entered.

"Have fun on the beach?" she asked. I had a full view of her sexy body.

"Oh, we discussed a few things," replied Gwen.

"Oh." Soo must have realized that it was a serious conversation. "So Cassie, will you be staying with us?"

No one in the household seemed to mince words. I was sure Gwen was hanging on my answer as well. "I haven't decided yet."

"Well, if it counts for anything, I would love it if you stayed."

It was so kind, and from the heart. "Why thank you Soo. That means a lot to me."

I sat on a bar stool and watched Soo prepare a Croque Madame, a sandwich of French origins made with sourdough bread, ham, gruyere cheese and bechamel sauce. Soo had already assembled the sandwiches and was frying them in a cast iron skillet, having already topped them with more bechamel sauce and cheese. They smelled delicious.

Rita came into the kitchen and peered over Soo's shoulder at the grilled sandwiches. "Those smell great. Can't wait to eat them." Rita set the counter with plates, napkins, silverware and glasses. She retrieved a large bottle of sparkling water from the refrigerator.

I watched Rita maneuver her stocky body around the expansive kitchen with practiced efficiency. The kitchen was well-organized and well-stocked. There was no mistaking Rita's sexual orientation. She had close cropped black hair and was wearing a muscle shirt and cargo shorts. Her arms were heavily tatted, with iridescent green serpents circling her arms. Rita was highly protective of Gwen, but with me having been accepted by Gwen, Rita was nothing but a sweetheart with me.

Soo started serving the sandwiches, hot and steaming, with a garden salad on the side. One thing I could say for certain, and that is that they ate well here. Gwen appeared and sat on the empty stool. She was holding a leather bound book, much like the diary she had shared with me a few days back. Gwen had been keeping a daily handwritten diary for as long as she could remember, and each year was memorialized in a leather bound book. She handed me the book, which like her other volumes, bore a leather strap and a lock. This volume was locked.

Gwen was now wearing a gold chain around her neck with a small key as the pendant. She cradled the key in her hand. "I'll give you the key at the right time. In the meantime, hang on to the book."

My suspicion was that we would re-enact another page in her diary, much like we did before, where Gwen had orchestrated my submission to her by replicating her diary entry from twenty years ago, with a submissive named Arlene. This volume seemed much newer than the one containing Arlene's entry. I put the diary aside and started in on my sandwich. It was as good as it looked.

* * *

After lunch was over Gwen asked me if I wanted to experience what it was like to go to a store in my role as her submissive. I of course said yes. She was holding something that looked like a leather dog collar.

When I said yes she handed me the collar. "I'd like to wear this."

Of course since I tend to talk before I think I blurted out, "It looks like a dog ..."

She gave me a stare that stopped me mid-sentence. "Did you want to go with me to the store?"

Her question told me that she was not presenting me with a choice, but with a demand. I backed down.

"Yes, Mistress."

"Good. Then put this on." She started to leave the kitchen and then stopped. "Be at the front door at four. Wear the clothes I've picked out for you."

I checked my phone. It was a little past two so making it on time at four wasn't going to be a problem. Did she say she picked out my clothes? What did she mean by that? Did she really go through my suitcase and pick out the clothes she wanted me to wear?

It turns out I was only half right.

I went up the stairs to my room, the room closest to the top of the stairs. I opened the door and was welcomed with a view of the Gulf from my bedroom window. Sunshine and maybe a chance of a late afternoon shower with the dark clouds looming on the horizon. The room was relatively small, accommodating a double bed, dresser, desk and an upholstered reading chair. Lying on my bed was a stack of cardboard boxes, the largest being from Sarasota's best boutique department store, the middle from a dress shop I was sure I couldn't afford, and the smallest from a high end shoe store located downtown. She picked out my clothes and shoes except they weren't mine.

I opened the top box. It was a pair of Christian Louboutin classic black pumps, red soles and four inch heels. I held up one of the shoes and admired the quality of the leather and the workmanship on the shoe. I would fuck anyone wearing a shoe like this. I couldn't wait to open the second box. It was a black skirt, very short. I held it up. I thought it was for someone two sizes smaller than me. It was beautiful but by my (questionable) fashion standards, tiny. I put it down and held up the largest box. It was feather light. I pulled off the cardboard lid and pulled back the tissue paper. It was a gorgeous form fitting silk top, white and opaque, pulled over a plastic form. I would look like quite the tart in an outfit like that.

I wasn't the best in walking in those kind of heels and decided to do a few calf raise exercises before I took a long, very hot shower. I shaved everywhere again, at Mistress Gwen's direction, and made sure I didn't leave any stubble behind. The hot water felt good. I started to think about the previous evening, when Gwen was teaching me some of the pleasures of anal sex. I started to get excited. I knew it was wrong to masturbate in the shower. Mistress Gwen forbade me from having an orgasm without her permission. But she didn't forbid me touching myself, and I couldn't help but touch myself with the hot water spilling over me. My fingers played with my slippery folds as I imagined being given permission to lick Mistress Gwen's pussy, to feast on her, to make her call my name.

My bathroom was a "Jack and Jill" type that I shared with Soo, who occupied the room next to mine. Soo was Gwen's submissive, a medical doctor of Chinese descent who trained in Hong Kong. I must have forgotten to lock the door leading to Soo's room. She walked in on me, naked, but for an oversized bath towel draped over her arm

"Oh, sorry!" she said, in her disarming British accent. I pulled my hand away from my crotch, reflexively embarrassed at being caught in the act. She made no move to leave, and stood there studying me through the steamy glass. Soo had already seen me naked twice, first when I had a little traffic mishap in front of Gwen's estate and fainted after I cut open my head. She cleaned up the wound and tended to me until I regained consciousness. The profusely bleeding wound coated my clothes in blood. Soo helped Gwen undress me and put on clothes of hers that she was going to donate. The second time was after Gwen had me submit to her in the kitchen, naked and blindfolded. Soo tended to me, rubbing salve into my sore nipples and my meticulously and thoroughly spanked bottom.

I looked at her through the wet, foggy glass. She was probably a smidge over five foot tall, long straight hair, jet black and glossy. She had pert breasts, unlike the full ones that I had, and though she was petite, she still had a desirable, curvy body.