The Education of Cassie

I regained my composure. There were no secrets in this house. How could there be when the three women living with Gwen, including myself, were sexually beholden to the madame of the estate? I looked at her expectantly, not knowing what she would do next. One of the choices was getting in with me, and that's what she did. She folded her towel and put it on the toilet seat and then opened the shower door and got in.

Her body rubbed against my soapy skin. If I were to describe it in ice cream terms, her skin was a creamy French vanilla. I wanted to lick the trail of water that was running down her shiny, wet skin.

"Florida is having a drought. Saving water ... right?" she asked me, trying to be serious, but trying not to laugh.

"Right ... right," I answered, making room for her in the stall and playing along with her.

She turned and faced me. The shower spray was hitting both of our faces, water running down our bodies. Her pale golden skin was almost luminescent as it was covered with fine droplets of water. Her nipples were erect, hard brown nubs, and her small pubic patch of straight black hair was shiny and matted together. I wanted her, and she knew it. We were only standing inches from each other. Her right hand cupped my breast, feeling my soap slickened skin against hers, and lifting slightly to heft the weight of my breast.

"So big, and so beautiful," she murmured, the beat of the water almost drowning out what she saying to herself. The feel of her skin against my breast made me squeeze my legs together in nervous anticipation.

She leaned forward and did I what I was hoping she wouldn't do. And not because I didn't want her to, but because of where I knew it was going to lead. She pulled my nipple into her hot, wet mouth, pushing her head against me without the reserve I was accustomed to. She fed on it, now using her left hand to squeeze my other tit, asserting herself without rules. This wasn't submission, it was passion. I put my hands on the small of her back, holding her tight against me, as my hands went lower to knead her firm buttocks.

"Oh, Soo ..." I managed to say breathily as my pussy, brought so close to climax by my fingers, was telling me there was no turning back. I put my hands on the shoulders of the shorter woman and gently pressed down. She immediately knew what I wanted and with her eyes asked me if this is what I really wanted. Of course at this point, what I wanted was irrelevant. What I needed was her tongue, buried to the hilt in my pussy, heedless of the consequences. I nodded my head slightly.

She took a washcloth off the shower's bench and laid it carefully on the tiled floor before she knelt in front of me. It was so sexy, so erotic, to see her kneeling in front of me, looking up, as the water rained down on the two of us. I stood with a wider stance, with my feet apart, as she wedged her slight frame between my legs. She grasped my butt with both of her hands and pressed her face upwards, her lips covering my labia, drawing the ripe, succulent flesh inside her mouth. She was schooled in submission by Gwen, and her proficiency in oral sex was something I hadn't experienced before. Before long, I almost swooned as her talented mouth brought me to the cusp of a head splitting orgasm. Only now faintly aware of Mistress Gwen's admonishment, I was too far gone to heed it. Soo's finger, coated with my pussy juice, wandered lower to rim my anus and then press against the entrance. The subtle pressure set me off, my hips involuntarily thrusting against her face as my anal ring gave way and her fingers slid almost effortlessly inside me.

"Shit!" I bellowed as an orgasm crashed down on me, weakening my knees and causing me to put my hands on Soo's shoulders to maintain my balance. I remember my eyes were closed and water was streaming off of my hair as I held her shoulders as I appreciated the gift she had given me, damning the consequences that would come later.

"Thank you," I said to Soo, helping her up to a standing position.

She smiled demurely. "You're so beautiful Miss Cassie," she whispered.

I finished rinsing myself off and then left the shower to Soo, drying off and then getting ready to see Gwen. With a towel wrapped around my head, I went into my room and checked my phone. Twenty minutes left, so I had to hustle. My little side excursion with Soo cost me my entire cushion of time. I wondered what I would tell Gwen. I went back into the bathroom to dry my hair. Soo was already gone, the glass on the shower already carefully squeegeed.

I finished drying my hair and putting on my make-up and now I only had a few minutes to dress. I had unpacked, and went through the dresser drawer to find a bra and matching panties. I put them on first, then the tiny skirt, the skin hugging almost translucent top, and then the slutty pumps. I wobbled a bit on the pumps before finding my center. Then I remembered the collar I was given. It was made of black leather, with rolled edges and a small chrome buckle. I went into the bathroom to look at the mirror while I fastened the collar to my neck. It felt strange, the light pressure of the leather against me. Also I detected a faint smell, the smell of sweat mixed with leather. I wondered who wore it before me.

I gripped the stair's handrail a bit tighter than usual as I side stepped down the stairs on my almost impossibly high Louboutin's. It was hard to feel slutty when I was trying to maintain my balance. I got to the bottom of the stairs. The front door was open. Mistress Gwen was standing on the threshold looking elegant in a designer pantsuit. I could see the Bentley idling in the driveway right outside the front door, Rita driving and Soo in the front seat next to her.

I walked up to greet Mistress Gwen, but she was having none of that. She flipped up the edge of my skirt to see my panties.

"I told you to put on what I had left for you."

"I did," I protested. I should have known better than to argue. Gwen reached under my skirt with both hands and jerked down on my panties till they were puddled around my ankles. This was part of the game. She had given me instructions which I was to obey literally. My mistake in donning a bra and panties gave her the opening to punish me. I felt contrite about my error, but excited and apprehensive about my punishment.

"What's this?" Her tone was accusatory and that wasn't good.

"My panties, Mistress Gwen."

Her eyes betrayed her disappointment. "Did I leave them out for you to wear?"

I already realized my faux pas, but of course too late. "No, but I assumed ..."

Before I could finish she grabbed the edge of my bra through my top.

"And this?"

"I'm sorry."

"Sorry for what?"

"Sorry that I didn't follow your directions."

"Take off your bra and get on your hands and knees."

"Here?" It was a mistake to challenge her, but I wasn't completely settled into my role.

She didn't answer. She stood there impatiently. Her silence was my answer. I fumbled with my top, eventually peeling it off. I took off my bra, threw it on the entranceway floor, and pulled on my top without it. My nipples now stood out prominently through the gossamer thin silk. I got on my hands and knees, my knees outside on the porch and my hands inside the house on the marble tiles of the entranceway. Mistress Gwen was outside, and flipped up my skirt, exposing my bare bottom to Rita and Soo, who were watching from the car. I turned my head to the side so I could see Mistress Gwen going to the car and searching in the glove box. She stood up holding a blue plastic ice scraper. Since it didn't snow in Florida it was left there for another purpose. I was pretty sure of what that purpose was.

"You disobeyed me." She wanted me to tremble. I was.

"Yes, Mistress Gwen." I felt the breeze blowing under my skirt and on my exposed privates. I was already wet.

"Disobeying me means punishment. Are you ready to accept yours?

"Yes, Mistress Gwen." I wasn't really ready. My butt was about to be tanned by an ice scraper in clear view of my two housemates.

She slapped my left ass cheek with the backside of the ice scraper, the ribbed plastic leaving a lingering hot, stinging sensation. She hit me a total of ten times, five times on each cheek. Tears were freely flowing down my cheeks. My ass was red hot, and the heat made by face flush. The fact that Rita and Soo also witnessed my punishment only escalated my embarrassment and humiliation.

There were no words from her scolding me for my behavior, nor were there words of comfort. I was on my hands and knees sobbing, spanked in front of my new sisters, punished for my transgression. Mistress Gwen reached between my legs to ask me how I felt about my punishment. The touch of her fingers on my pussy almost made me cum. I flinched. She drew her damp fingers, wet and glossy, and examined them in the late afternoon sunlight. She had her answer. She was to provide no relief.

Ashamed that I was publicly humiliated, and even more ashamed that I loved it, I got into the back seat of the car, sitting next to Mistress Gwen. The cool, supple leather was like a salve to my tortured backside. Rita turned the car around and drove down the driveway. The gate automatically opened, and the massive black car carried us down the tree lined street.

* * *

The car turned into the parking lot of a strip shopping center on the edge of Longboat Key, right before entering the city limits of Sarasota. We parked on the far end of the lot, away from all of the other cars. The store on the end, "The Velvet Rope," had its display windows blacked out. Rita opened my door for me. I looked around the parking lot before I got out. I wasn't comfortable being seen in my skimpy outfit.

I teetered on my heels, walking like a drunk across the irregular surface of the crumbling asphalt parking lot. Rita opened the door to the store, and cow bells attached to the inside handle announced our arrival. A matronly woman, probably in her 40's, came through a beaded curtain in the back of the store wearing a broad smile on her face. She had close cropped bleach blonde hair, a cherubic face, enormous breasts and an ample backside. If my gaydar was working, she was a classic butch lesbian.

"Gwen." She greeted my Domme with open arms. The hug was long and genuine.

"Babs."

I found out that Babs was short for Barbara, and Gwen and Barbara had been close friends in New Orleans. They both found themselves in Longboat Key, by coincidence rather than by design.

Babs looked at me, slowly and deliberately, her gaze making me feel uncomfortable. I dipped my chin, looking at the short pile commercial carpet under my "fuck me" heels.

She pronounced her verdict. "She's a beauty Gwen. Where did you find her?"

It was strange having two people talking about me while I was present.

"Showed up at my door last week."

"So they're still doing that?" Babs must have been familiar with the scene in New Orleans in the 80's. Women often showed up at Gwen's house, hoping to be invited in.

"No, she's a newspaper reporter. I think she's better being a sub, but I'm looking forward to the article she's going to write about me.

"A reporter embedding herself in your little complex?"

"More like bedding herself in our complex." The two women shared a laugh at my expense. I could hear Soo and Rita chuckling behind me as well.

"I'm sure you're here for a reason. What can I do for you today?"

"Cassie wanted to go shopping. I was hoping we could buy a few toys for her." Gwen turned her head so she was looking towards the back of the store. "We were hoping to use the private room in the back."

Babs went to the front door. She hung a sign on the outside handle that said "Be Back Soon." It had a cardboard clock on it with the hands showing she'd be back in an hour. She locked the door.

"Let's go." Babs led us to a room in the back marked "Private." She pulled the key ring attached to her belt loop and unlocked the door, pushing it open.

"What would you like to see?" Babs asked, letting us into her private playroom.

We entered the room. I saw black floor tiles made of rubber and a drop ceiling. There was a study wooden bench in the middle of the room and what I recognized as a St. Andrew's cross in the back of the room.

Gwen pulled me close to her, putting her arm around my waist before answering Babs. "You know what we have ... surprise us."

Gwen put her hand under my skirt, giving my sore bottom a gentle squeeze. "Honey, you go stand over there." She pointed to a large wooden "X" against the back wall. "Rita, why don't you and Soo help her?"

By help, she meant helping me take off my clothes and then fastening the cuffs so I was facing the cross with my wrists bound to the cross above me and my ankles bound to the cross below me.

With me facing the cross, I could only hear them, but couldn't see them.

"So this is something that just came in. The highest quality. All handmade by a shop in Tampa. See the length of the falls. And the ends are knotted for additional "pop."

I could hear Mistress Gwen playing with it, the leather falls swishing through the air. "Mind if I try it out?"

"Of course. That's why we're here."

"You know Cassie here had an orgasm this morning without my permission."

Shit, Soo had given me up.

"Tsk, tsk, poor Cassie."

I started to tremble. Before I could get into full panic mode I felt what seemed like a hundred fire ants biting my butt at the same time, re-igniting the burn from the ice scraper spanking no more than an hour ago.

"Owww!" burst out of my lungs as the bite of the flogger's tails left a persistent white hot heat.

The excitement in Gwen's voice showed delight. "That felt great. The weight ... the momentum ... I liked it. It's a keeper."

Bab was pleased as well. No one in the room was apparently concerned that there was a five alarm fire raging on my backside. "I knew you'd like it. I ordered it with the thought that you'd buy it."

"You know me too well."

"Let's just say I know your tastes."

"Well, now that it's mine." She let go another swing, this time harder than the first. The pain level went up again, my eyes starting to water. Now I was craving the light at the end of the tunnel.

Three more strokes and I was bawling ... and begging.

"I wonder if she liked it," Gwen mused. "Why don't you do the honors of finding out."

This seemed to be the universal test. Apparently my pussy was incapable of lying. I felt Bab's hand on my crotch, smaller and meatier than Gwen's, drag across my sex. Her touch lingered longer than necessary, her fingers playing with my fleshy folds.

"Ahhhhh," I sighed, even though I didn't want to.

"She likes it." I heard Babs lick her wet fingers.

"I knew she would. She's turning into my little pain slut."

"Can I ..." Babs started to ask.

Gwen answered before she finished asking. "I think you should ..."

"She's so pretty. Gwen, you have all the luck ...".

Babs stood next to me. She was shorter than Gwen by a few inches, but much bigger breasted. Her breasts rubbed against my side as she leaned up against me.

"You little slut ... you liked the flogging ... didn't you?" her hot breath making the hairs on my neck stand on end.

I nodded my head. My butt was on fire, but I liked it. My whole body was warm ... and I was horny.

She rubbed my pussy. I started panting. This is what I wanted. I wanted it now.

"Please ... Babs ... please ...". Begging seemed to be part of the ritual and it came naturally to me.

"You're ready, aren't you?"

"Yes ... yes ..." I said breathlessly.

"You're asking the wrong person little one."

"Mistress Gwen ..."

Babs pushed two fingers inside me. I wanted to explode.

"Please ... please ..." My begging was both persistent and pathetic.

Gwen completely ignored me and my begging. "What else do you have Babs? I don't want to go home with just one thing."

No. Please no. I was desperate. But I couldn't move my hands or my feet. I could feel my pussy juices running down the inside of my thighs. The roller coaster was perched on the top of the first drop. I wanted it to plunge forward. The anticipation was far worse than the pain.

"I've got one other thing that came in last week. I tried it out last week. Worked well."

"Well, bring it."

I heard the door open, then shut.

I was quivering with want. Mistress Gwen knew exactly what she was doing. She had wound me up as tight as she could. The release was going to be spectacular. I waited ... what seemed like eons. The door opened and closed again.

It was Bab's voice. "I think you'll like this."

"I think you should demonstrate this on my slut, don't you?"

"Of course."

I heard a mechanical whirring noise. It became louder as Babs came closer. She got on her tip toes so she could whisper in my ear again. "You're going to like this."

It was a two pronged vibrator. I felt the larger prong press against my anus. My anal ring stretched, but didn't give way.

"Uhhhh," I grunted at the unexpected pressure and impending intrusion.

The pressure went away and I heard her spit. The tip, wet with her saliva, wiggled against my anus until it gave way, welcoming the plastic invader into my ass.

"Ahhhh," I purred as the smooth plastic slid effortlessly into my back channel, my muscles gripping the vibrating cylinder. It felt fantastic. Ass play was definitely being added to my list of kinks.

"Now here's the good part." I thought I was getting the good part. I was wrong. The other smaller arm of the vibrator was meant to massage my clit. Babs twisted the vibrator so the smaller arm was touching me there.

I heard a faint disembodied voice in the background. "You may cum."

"Oh my God!" I practically shouted as the little plastic arm rocketed me to an orgasm. I flailed against the St. Andrews cross as Babs fucked my ass with the vibrator, with each thrust grinding the smaller arm against my clit. A copious amount of liquid streamed down my legs. It was the first time I squirted. It was a monumental release.

Through the haze of the pain and pleasure I heard Bab's voice, now in the back of the room.

"I think she's a keeper."

"I do too," I heard Gwen reply.

I hung limply against the cross. The humiliation, the pain, the anticipation, the fear, and the release - it was all perfectly orchestrated by Mistress Gwen. I wondered what diary entry she had followed.

She was making it hard on me to ever leave.

* * *

That was the most exciting shopping trip I had ever been on. Soo and Rita had to help me back to the car. I didn't remember the ride home. They put me to bed, and I think I slept for quite a while before I woke up at 2 a.m. I was hungry. I had missed both lunch and dinner. I threw on a robe over my pajamas and padded down the stairs in my slippers. I saw that the light was on in the kitchen and went in. Rita was sitting on a bar stool eating a sandwich. She was wearing a men's white t-shirt and navy boxer shorts. She looked gruff and tough but I knew the truth. She had a good heart and would do anything for Gwen.

"Hey sleepy head." She put her sandwich down and grabbed the open bag of potato chips that was sitting in front of her and pushed it in my direction.

"Chips?"

"What are you eating?"

"Sandwich. There's leftover ham in the fridge."

That sounded good to me. Rita could see that I was hungry. She pointed. "Bread's over in the drawer next to the toaster."

I went over to the drawer and pulled out a half loaf of sourdough bread. I opened the plastic wrap and pulled out two inside slices. Rita got up and retrieved a plate from the dishwasher. It was still warm from the drying cycle.