My Personal Trainer Ch. 02

While I was bent over, Mistress Isobel took out a stainless-steel double ended clip and used it to attach the handcuff chain to a stainless-steel ring embedded flush in the surface of my dresser.

"That wasn't there before," I observed after I'd been made helpless.

"Before I agreed to come to your home to dominate you, I told your mother to have rings like this installed all around the house," Isobel explained. "That way I can easily make you helpless no matter what room you're in."

I felt a chill down my spine at the implication. I struggled, but the handcuffs and the steel ring both held firm. I wouldn't be getting free until Isobel used the key to unlock me.

"The rings look ornamental to the casual observer," Isobel commented. "One would have to be quite perceptive to guess their true purpose."

Mistress Isobel took her leather strap and let me get a good look at it before using it on me.

"You were a brave girl during your spanking," she whispered in my ear as she stood intimately close and placed one hand possessively on my ass. "You took your punishment well. I'd like to see that sort of bravery when I whip you with the leather strap."

I trembled. Things were moving fast. I'd gone my entire life without being spanked. Now, I'd finally been spanked, and I was going to be whipped just a few minutes later?

My heart thudded in my chest, and I felt a wave of fear... dark, delicious fear, wash over me. Would I be able to handle being whipped? I doubted my resolve, but I wanted Isobel to be proud of me.

I planted my feet and braced myself for my whipping.

Isobel took up a position behind me, folded the leather strap in half and then swung it at my already sore ass cheeks. I had just barely enough time to register a whoosh sound before I felt the crack of leather on my bare skin.

"Aaahh," I cried out in pain. My mother and my sister were in the house. I didn't want them to hear me screaming, but the leather strap was vicious. The sting was worse than being spanked. There was no way I could handle being whipped without screaming.

My cruel mistress didn't allow me any time to adapt to this new, unfamiliar agony. An instant later the leather strap struck me again, this time across the left buttock. And then a third crack of the belt scorched me across both buttocks.

"AARGHH," I cried out as the cruel leather continued to punish my bare bottom with stinging blows.

I continued to scream, stamp my bare feet and struggle against the handcuffs that held my wrists. Of course, all I succeeded in accomplishing was chafing my wrists, but the sudden, sharp, stinging pain made my body react without thinking.

She continued to punish my poor bottom and I continued to scream. I'd had fantasies about being punished like this for years. The reality was far more intense than any of my late-night fantasies, and as I danced under the whip, I wondered if I'd bitten off more than I could chew.

I felt a shocking pain and my body's instinct to escape it was overwhelming. I had dreamed of this, but my body wasn't ready for it. I writhed, twisted my hips, and danced under the painful assault of the strap.

When it was over, my breathing was ragged and my face was wet with tears. I hadn't even realized I had been crying, but my face was soaking wet with the tears that I had shed.

My bottom was in scorching agony, and my wrists were chafed from struggling against the metal cuffs, but at least I finally knew what it really felt like to be punished by a cruel mistress. I'd accomplished something that I had set out to do, even if it meant my bottom was so sore, I'd have to sleep on my stomach tonight. I'd accomplished a very real and important goal in my life.

I was still sobbing and my head was hung low when Mistress Isobel laid a gentle hand on my shoulder and said, "After I leave, don't get dressed. I want you to remain naked for at least two more hours."

I gasped. I had assumed that her authority over me would end after she left my house, but apparently her control over me was going to be more encompassing than that.

"And don't lock yourself inside your room. Leave the door open. If your mother or sister wants to come in, let them. If they have questions about what happened here today, answer them as honestly as possible. I don't want you to keep secrets from them."

She unlocked my handcuffs and I rubbed my chafed wrists. They were sore from all the struggling I did while I was being whipped. Before she walked out of my room, she kissed me and then placed her hand between my legs, kneading my swollen pubic lips until I moaned.

"And remember, no flying solo," she said as I gasped and squirmed. "Slaves aren't allowed to give themselves orgasms. If you cheat, I will find out about it, and you will be punished."

I bit my lower lip and suppressed a sigh. There was a wet pulsing in my sex, and I already felt an urgent need to finger myself to orgasm. But I also desperately wanted to earn Mistress Isobel's approval. I had spent years dreaming about having a master. Now that I had one I refused to give up the moment things became difficult.

That was sort of the point of being a slave anyway. Things were supposed to be difficult. Weren't slaves supposed to endure trials and distress? I whimpered and watched Mistress Isobel walk out of my room. In her gym bag she had most of my panties. I'd have to buy more to replace the ones she took.

Of course, to be an obedient young lady, I'd need to stick to thongs and V-Strings. Full size panties were out of the question.

I was naked and my ass burned and throbbed from my first ever punishment. I walked back over to the mirror to get a good look at my sculpted ass to see just how red and punished it looked.

"Oh, wow."

I was studying my ass in the mirror and marveling at how little visible damage had been done to it when my sister walked in. Her face was a mask of concern and she stood there quietly, waiting for me to acknowledge her.

"Hello, Drew," I said after I tore my gaze away from my reflection.

"Hey, Robin. So, the scary woman is gone," Drew said. "Would you like to fill me in on what's going on with her? Why are you letting her do these things to you?"

"It's hard to explain the attraction to someone who isn't a masochist," I said to Drew.

Being abused and dominated by Mistress Isobel made me feel like nothing I'd ever experienced before; tension, anticipation, risk and a delicious sense of fear all combined in a potent emotional cocktail.

"Can you at least try?"

I nodded, and said, "So, I had this impossible sexual fantasy. I was alone and agonizingly frustrated. There was no one I could share my desires with. Mistress Isobel is allowing me the freedom to become what I desperately wanted to be. Couldn't you see that my puss was soaking wet when she forced me to display myself?"

"I thought you looked humiliated," said Drew.

"Of course I was, but knowing that Mistress Isobel has the power to humiliate me is what makes it all so intense!"

Drew gestured at my reflection in the mirror, having spotted how red my ass looked and accused, "She whipped you!"

"Yes," I admitted. "And it hurts like blazes. But it's a rush. I've never been so sexually aroused. My whole body is just one huge, throbbing mess of sexual desire right now."

"Yeah, your nipples are hard right now," Drew said as she looked me up and down.

"And I get this weird feeling of pride after taking a brutal punishment. I look at the painful marks on my ass after a punishment and something about those marks makes me proud."

"Proud?" my sister asked incredulously.

"Yes, I know it must sound crazy."

I looked over my shoulder, and I studied my reflection in the mirror and added. "Somehow all that extra color made my ass sexier. And knowing that I'd endured all that pain for Isobel, it's like a masochist's badge of honor."

Drew was a good sister. She tried to understand why this was important to me. She found it all counterintuitive, but in the end, she concluded that being the submissive one in a BDSM relationship made me happy, so she was going to be happy for me.

We talked for hours, and then I went downstairs to retrieve my clothes. When Isobel had ordered me to strip naked, I left them down on the hall tree in the foyer. I grabbed my bra and panties and looked around for my dress.

It wasn't with the rest of my clothes.

"Where's my shirtdress?" I asked.

"Isobel said you're no longer allowed to wear that," my mother explained. "She said that you have beautiful legs and that you need to show them off. You're not allowed to wear any skirts or dresses with hemlines that go any lower than this."

Then she brushed her fingertips across my thigh, approximately four or five inches above my knee.

"That's pretty high," commented Drew.

"She also wants you to sign this," my mother said, and she went to fetch a very legal-looking document for me to sign.

"Isobel and I have already signed it. All we need now is your signature."

I looked it over. It was approximately ten pages long. It identified me as "the subordinate." It identified Isobel as "the overseer." It gave her authority over me.

It stated she had the authority to decide when I was allowed to wear clothes, what I could wear, what I was allowed to say, and of course, it gave her total control over my sex life. She could pick out sex partners for me and demand I perform sex acts for them.

The list of ways she had authority over me went on and on forever. And then there was a list of ways that she was allowed to punish me if I ever disobeyed her or disappointed her in any way.

I only went through the first paragraph of punishments before I felt a shiver run up and down my spine. It was daunting to think that Isobel could do these things to me... but it was also intensely exciting.

My head was swimming. It all seemed so unreal. My most private sexual fantasies coldly summarized and presented as a contract.

I didn't read the whole thing. I skimmed it and then signed on the last page, making my submission to Isobel official.

I doubted that the contract was legally enforceable, but signing my name to it had a potent emotional effect on me. I felt utterly submissive to Mistress Isobel and my pussy clenched and spasmed at the thought of how much control she now had over my life.

I felt like a real sex slave. I was naked, my punished bottom was a riot of scalding pain, and I'd just signed a contract that said I'd given up my rights and that Isobel was now my overseer.

* * *

I eventually got dressed and Drew and I went out clothes shopping.

My levels of sexual arousal were frantic, and my ass was so agonizingly sore it made it difficult for me to concentrate. I didn't trust myself behind the wheel. So, I recruited Drew to be my driver.

Our first stop was Cleo's.

It's a high-end women's clothing boutique. They feature a hand-picked collection from independent designers, and upscale labels. They also have attentive staff who will hover over you, offer suggestions, and help you in any way imaginable.

Drew knew most of the staff there. She told a girl named Marie that I was there looking for dresses with high hemlines that would display my legs.

"The higher the better," Drew explained. "My sister has amazing legs, and I want them showing as much as possible."

I could feel myself blushing. My sister was trying to help, but she ended up sounding like a pimp trying to make sure his high-end escort displayed her charms to the best advantage.

Marie was eager to comply. She came back with a selection of elegant minidresses that would leave a lot of leg showing. I tried them all on. Drew tagged along with me to act as a second pair of eyes and give me her expert opinion. Clothes had never been all that important to me, but Drew considered herself something of a fashion expert.

I tried on approximately twenty dresses. Drew picked out six that she said looked perfect on me. We told Marie which dresses I wanted and requested alterations to make them show off my narrow waist.

Marie was all smiles and cooperation, and she promised to have the dresses delivered to my home as soon as they were ready.

The next stop was to Victoria's Secret. I purchased six thongs and six V-strings. I got a few impulse items while I was there, but I was mainly getting panties that I knew Isobel would approve of. She felt that a slave with an ass like mine shouldn't be covering it up. Therefore, all my panties needed to put my ass on display.

* * *

My mistress/overseer had given me an assignment. I was to dress in the sluttiest dress I owned and go to a lesbian bar in Greenwich Village and try to get one of the women there to make out with me.

Mistress Isobel knew that I was straight. She wanted me to do this because she knew it would be awkward and difficult for me. She felt it was good for slaves to be humiliated and in distress.

Drew offered to drive me, but I felt that bringing my sister to such an event would be crossing a line that shouldn't be crossed. I loved that my sister was being so supportive, but I didn't want her to see me in a situation like that.

I took a Lyft to the lesbian bar. The name of the place was Wonderland. I stood outside of Wonderland with a growing sense of anxiety in my chest. I was naked underneath my indecently revealing dress, and that bar was going to be filled with ravenous lesbians.

I considered not going inside. I could call for another Lyft to take me straight home. Of course, if I did, Mistress Isobel would punish me horribly for failing to follow her orders.

I walked in and there were clusters of delicate hanging lamps and custom butterfly sconces throwing warm light across the room, supplemented by neon signs. One prominent sign read "Welcome to Wonderland." Another neon sign by the bar declared, "This is where the magic happens."

Twinkling fairy lights were woven throughout the ceiling and walls alongside eccentric artwork to reinforce the feeling of being transported out of the city. It took me a few moments for my eyes to readjust to the different lighting and atmosphere.

Of course, it only took a few moments for the other patrons to notice me. I had a nice body, and I was wearing a dress that was so revealing it was practically indecent. A redhead in a black dress closed the distance between us fast. Her eyes were bright and enthusiastic. She smiled enticingly at me and said, "Hello. I don't believe I've ever seen you here before."

She was cute, her dress was stylish and I liked her accent. Possibly British? I wasn't sure. I was about to introduce myself when a taller woman approached, placed her hand on the cute redhead's arm, and said, "Back off, Amy! I saw her first!"

The blonde in the royal blue dress was stunning. She was taller, fit, sculpted, and fierce. Her dress looked like mine, same color, same tight fit, only not as revealing as mine. The redhead was intimidated by her and backed off, leaving me alone with the statuesque blonde.

"My name is Jill," she said as she turned her full attention to me.

"I'm Robin," I replied timidly.

"You're very pretty," Jill said. "Of course, you probably knew that already."

I laughed nervously. I had assumed that I'd have time to explore the place before talking to any of the lesbians. I wasn't expecting to get ambushed the moment I walked in the front door. She had a dominant energy I found intimidating.

"You're pretty too," I said, fumbling for words. My heart was beating too fast and my pulse was racing. I had trouble thinking clearly and the words weren't coming to me. I felt clumsy and awkward.

I offered to buy her a drink at the same moment as she was offering to buy me a drink. There was a moment of silence and then Jill ended up buying drinks for both of us. We got two shots of high-end tequila, and the liquid made my insides feel warm.

With the alcohol swimming inside my veins, I slowed down and noticed details I'd been too nervous to notice before. Jill's face was flawless, and full, and sported an incredibly full-looking pair of lips that glistened in the light of the room.

The proximity of her face gave an odd and sensual intimacy to the moment, and I squirmed and felt my temperature rising. She was so attractive and standing so close. The way Isobel had punished and dominated me left me feeling so excited, the alcohol was loosening my inhibitions, and Jill was so warm and close. My head reeled and without thinking each of us reached for the other.

Jill's breath smelled of high-end tequila. I think I told her that I was nervous, and she told me it would be okay. Her voice was alluring and hypnotic and then we kissed.

Jill held my face in her hands and her mouth touched mine. Her lips were soft and warm, softer than I imagined they would be. I felt feverish all over, and when Jill's mouth claimed mine, I moaned.

I moaned into her mouth and kissing a girl felt far better than I thought it would. Jill's kissing technique became more passionate and I responded in kind. Isobel had ordered me to engage in passionate kissing with a lesbian and she hinted very strongly that she would know if I obeyed her orders or not.

Jill grabbed ahold of my hips and pulled me closer, brushing her breasts up against mine as we kissed. She attempted to work her tongue into my mouth, and my first instinct was to resist her.

Then I remembered Isobel. She was my overseer. I was her subordinate. She would want me to submit to this lesbian woman. I silently submitted to Mistress Isobel's authority and allowed the blonde woman to probe my mouth with her tongue.

Our tongues brushed against each other in some sort of erotic dance inside my mouth. We grinded our bodies against each other as we kissed passionately. Her tongue tasted good in my mouth although it felt weird doing this with a girl. I concentrated on being obedient to my overseer. I had signed a contract that said she had authority over me. I had to do whatever she said. That included dressing in a slutty minidress, going to a lesbian club in Greenwich village and making out with a lesbian.

Jill was an incredible kisser which made my task far more enjoyable than I'd anticipated. Then Jill's hands slid lower and one of them worked in underneath the hem of my dress and grabbed my ass.

My ass was still tender from being whipped and I let out a girlish yelp. I flinched and pulled away to protect my sore bottom.

"What's wrong?"

My head was reeling and I was slightly drunk. I was off my game and unable to formulate a believable lie, so, I just told the truth.

"My mother hired a dominatrix to come over to our house," I explained. "She whipped me this morning so now my ass is too sore for me to be getting groped."

Her eyes widened and she released her hold on me. She took a step back and said, "Oh, that's too kinky for me. I'm out."

Jill gave me a look and retreated to a booth filled with other women. It suddenly seemed as if everyone in Wonderland was looking at me.

It was probably just me being anxious and paranoid. The club was too noisy for most of the patrons to hear what I'd said. Still, I felt vulnerable and exposed and I ended up leaving Wonderland and heading home.

That night, I had feverish dreams where I was naked in a women's prison. I was in a shower room with other female prisoners.

Jill was there. Amy was there. Isobel was there. They were all naked and glistening wet. They advanced on me and I was pushed against a wall. They took turns, groping and kissing me and I was helpless to stop them.

Isobel worked her hand between my legs. She grabbed my swollen, sensitive pubic lips and I moaned. I twitched and gasped. The other women stood close by and gave me prurient looks as I was raped.

"She's soaking wet," Isobel exclaimed as she played with my pussy. "It's like she enjoys it when I treat her like this."

I tried not to wriggle and squirm too much as Isobel massaged my sex lips with her fingers. Then she found the entrance to my vagina and thrust two fingers inside me.

"Oooooh!"

Jill and Amy encouraged Isobel to probe deeper into my moist interior and make me gasp and yelp and squirm. Mistress Isobel was happy to accommodate them.

She brought me close to orgasm and then withdrew her fingers from my sopping wet pussy. I moaned piteously. The other women seemed to enjoy the sounds I was making.

That morning, I woke up; my pussy was almost as wet as it was in my dreams, my nipples were so hard that they ached. There was a soft, insistent, wet pulsing in my sex, and I struggled with Mistress Isobel's orders forbidding me to masturbate.