Legal Kinks

Helen was our company lawyer. She was very good at her job, although she was a bit frosty around the office and some of the women considered her a bitch. She was 40, tall, slim and striking, and she dressed the part with pencil skirts and high heels, she made an impression wherever she went. She was married but childless as far as the rumor mill knew. She was the kind of woman I fantasized about: classy, older, sexy, strict.

Six months after I started with the company I was working late since my Fiancé was working nights and another evening of dressing up and satisfying my porn addiction in my empty house was for once not pulling me away from the office. I picked up on an anomaly in the charges from one of our suppliers and started digging through old invoices and deliveries. It wasn't easy, the delivery notes were scrappy at best, but it piqued my interest. The next morning, I went to my boss, and explained my findings, our supplier had been overcharging us for almost four years and it came to a total of over two million dollars.

One phone call and ten minutes later Helen stepped into the CFO's office, looking every bit my fantasy woman, as usual. She was astonished with the news we had for her and then her admiration became evident as the CFO had me outline what I had discovered and how. By the time we broke up from the meeting she was far from frosty towards me.

Over the next few months, we spent a lot of time together putting together the documents she needed to confront the supplier and then, having been met with a firm denial and refusal to cooperate, the filing of a suit. She had a surprisingly wicked sense of humor and she seemed to be warm to my quirkiness and certainly delighted in my eagerness to please her. At some point she moved from calling me James to the more feminine form: Jamie. I loved the way she said it, loved what it implied about how she viewed me. I looked forward to every meeting I had with her, reveled in the time I was able to spend with her and dreamt of her in my fantasies and daydreams. When she was busy discussing things with others in the room, I would study her drinking her in. A couple of times she caught me looking at her legs, the first time she just raised her eyebrows at me, the second time a couple of weeks later she gave me knowing and rather suggestive little look. I couldn't have been more embarrassed, but it did fuel my fantasies even more.

Then the shit hit the fan. With trepidation I knocked on the door to her office and, seeing that I was interrupting her, I quickly told her I was no longer able to be involved in the suit.

"Why not?" The obvious question. She was clearly busy with something else, but I immediately had all of her attention.

I stammered and flushed my way through the answer I had prepared, I might have fooled most other people I knew but not Helen.

"Shut the door." She said quietly, not taking her eyes off me. "Sit down and tell me what I'm missing. I can't lose you as a witness."

Nervously I tried to dig my way out of my situation, but she wasn't fooled. I was sweating, I hated to lie to her, but I couldn't face telling her the truth.

She sat quietly looking at me for what felt like an age. "Has someone threatened you, Jamie?"

She had hit the nail on the head. I nodded silently, dropping my head. My heart breaking, knowing my secret had to come out.

She must have read my panic and desperation, because in a quiet voice she said: "I can protect you, Jamie. Completely! But I need you to come completely clean with me. I need you for the case for sure, but the case aside, I don't want anyone threatening you."

Through a nervous pounding heart I stammered out my situation, knowing that it made me look pathetic and that she would most likely think less of me. I had been threatened by the man we were suing. He would reveal things about me that would ruin my relationship with my fiancé and humiliate me with friends and colleagues. Eventually she coaxed out that I had been posting pictures of myself in lingerie and been visiting femdom and male-dom sites for years, photographing myself in all sorts of compromising positions, staging some photo's to look as if I was not alone. It was something my fiancé would not entertain and that she was revolted by, but my compulsion led me to do it anyway and so I did it in secret. I promised her that I never involved anyone in any of this and that it was just my fantasy life.

When she was satisfied that she had got all of the facts from me, she said. "Jamie, you can live your life the way you want. It's not for him or me or anyone else to judge. But he cannot legally threaten you like that. He is a thug and a bully, he broke the law by doing this to you. I can get him to back off! Give me three days, then if you still want to back out I won't force you to testify."

Reluctantly, humiliated I agreed.

She called in an IT guy she trusted and told him the basics. He grinned at me, I flushed red and Helen immediately said: "This is absolutely confidential, not a hint of this can become public, it's not negotiable at all. We have to nip this in the bud. I need to know how he got the information on Jamie and who else he has threatened."

Three humiliating hours later I left Helen's office. As I was opening the door, she looked at me and said: "I'm sorry this is happening to you, Jamie. I don't like seeing my friends suffer. I'll beat this bully for you and then I'll make him suffer in court." Then almost as an afterthought: "No more of this until the trial is over! Nothing online, no porn, no forums, no messaging! Not even any dressing up in private! Nothing! Do you understand?" It was an order, sternly given, with not a hint of warmth.

I nodded, chastened. "Yes Mrs. Watkins." I replied, my face a hot red of humiliation as I turned to leave.

"Phah!" She chuckled, as I was closing the door. "I hoped you were going to call me "Mistress!""

My head was going to explode with the turmoil of humiliation and self-disgust mixed with the thrill of being considered one of her friends and that last throwaway comment: "Mistress". That final comment fed my fantasies for weeks! My fiancé never had to find out about my dressing up and Helen made the threats go away. Unfortunately, my promise to Helen meant the lack of playtime online and dressing up alone in my bedroom. That brought home the stark reality of the waning relationship with my fiancé. Her lack luster performance in the bedroom was just a symptom of her loss of interest in me.

The case was tried months later, by which time my fiancé had left me anyway, putting me into a lowly depressed state. True to her word Helen had closed down the threats and in doing so had ensured my loyalty to her and to her case.

On the second day of the hearing, I had to go on the stand. Helen guided me through a series of questions that I was prepared for and then smiled at me as she sat down. She then watched me being cross examined. The attorney was quick and gave long winded questions that were difficult to answer simply. I could feel myself squirming as I tried to answer the questions artfully, all the time looking to Helen for approval and help. She was still smiling at me, she never seemed to take her eyes off me and that made it more awkward still. There was something predatory and proprietary about her look, she was watching my discomfort and she seemed to like it.

We won the trial. Everyone had left as soon as they could, I stayed to the end for no other reason other than to be close to Helen. As we walked out of the courthouse lobby the very pissed off defendant rounded on Helen and yelled "You're a fucking Bitch!" Then turned to me and sneered: "You're just a worthless fucking sissy!"

Helen pushed between us and Hissed: "You're a pathetic thief! You are both morally and financially bankrupt and, if you ever threaten any of our staff again, I'll make sure you go to jail for it." She turned and walked away, linking her arm with mine. Grinning at me she said loudly: "Great feeling, winning! Come on, this Bitch lawyer is going to take her favorite sissy out for a celebratory lunch!"

With my heart singing, we went to a steakhouse and ate and drank too much, having a good time reveling in the win until Helen, more than a little drunk, asked: "So! Did you keep your promise? No porn, No surfing online. No Dressing up?"

Sheepishly I nodded.

"Say it!" She said, a stern note in her voice.

"Yes, I kept my promise to you!"

She waited, her eyebrows raised, a little grin on her face, obviously expecting more.

"Mistress!" I added quietly, a little tongue in cheek, the alcohol loosening my tongue.

The giggled delightedly. "Well good! I expected nothing less!" She said lightly with mock severity. Then: "I have a little thank you for you."

She looked a little nervous as she handed me a gift bag. I'd seen her do the same for everyone else involved in the case and had heard they were bottles of wine with lavish gift cards for restaurants, coffee houses and other places tailored to each person. I was delighted to receive the gift but the bag was much lighter than I expected. When I opened it, I blushed red, inside was something pink and lacey. I could barely look at her but I could feel her eyes on me.

"I thought it was a suitable reward for all of your hard work and sacrifice. You are such an obedient little thing and you've been through a pretty tough time with the suit and the threats and Kate walking out on you. You deserve a bit of a treat! Sorry for embarrassing you, well sorry, not sorry! This might be the kinkiest thing I've ever done and it's fun!" she giggled still a little bit of the confidence gone as she tried to gauge my reaction.

I grinned at her sheepishly. I couldn't hide the delight of the sissy within, even through the embarrassment of being given such and intimately girly gift in such a busy place bustling with serious focused businessmen and women. With the ice broken and more wine disappearing into both of us Helen wanted to talk about sex. She always led conversation, always had lots of questions but now they were focused on fetishes and kinks. She kept pointing out people in the restaurant and we took turns guessing what their kink might be. We were both having a great time and it felt like the first time I had laughed in months. She revealed that her sex life was "very vanilla" and that it pretty much always had been. She coyly said that she was letting her hair down buying me this gift and that got a little thrill doing it.

When I got up to go to the bathroom she nodded at the bag. "Take it with you, try them on, I had to guess your size, make sure they fit."

A little humiliated, I carried the little bag discreetly back to the bathroom. Once inside, with the door locked, I peed and then stripped. The feeling of the ink lace panties, bralette and stockings on my bare flesh was delicious. I was so aroused. I had missed this so much! And the thrill that Helen had bought it all for me! It was all I could do to leave without jacking off to the sensations and thoughts bombarding my brain. But, thinking of Helen, my Domme (Oh how I wished!) I redressed, leaving the lingerie on underneath my suit. Steeling myself I opened the bathroom door and walked back to the table. Anyone who looked too closely might have seen the pink stockings at my ankles, but no-one seemed to notice.

Helen was grinning from ear to ear as she watched me approach. "Well?!" she asked as I was sitting down.

Sheepish but thrilled, I said: "Thank you, they're beautiful and you guessed my size perfectly!"

Smiling contentedly, she looked down at the little bag. Nudging it open with the sharp toe of her pump she could see that only my own underwear and socks were in there. She looked back at me with delighted eyes. "Somebody's feeling brave! Feels good though doesn't it!"

I heard a feint click as her pump fell on the floor then I felt her toes traced their way up the inside of my leg. She looked me directly in the face and talked to me about how sexy the silky stockings and lace felt on my skin. I could barely focus on the words she was saying to me. Every nerve in my body was thrilling to the erotic experience of being teased by this wonderful woman. My cock was rock hard but trapped inside the new lace and satin. There was nothing vanilla in her look as her foot stroked up the inside of my thigh and nudged that hard ridge of my cock. She rested her toes on it, wriggling them slowly from side to side.

"What does a sissy call this? It's too big to be a clitoris but it's difficult to call it anything manly when it's wrapped in pink lace!"

Her toes kept moving a slow dance and it was all I could do not to writhe and lift my hips into the pressure. I was in heaven, breathless and incapable of answering her. The waitress saved me from almost certain calamity by coming to the table then. She may not have known exactly what was going on between us, but she got the genera idea when she got close and asked up if we wanted our bill, breaking the spell Helen had over me.

Helen paid the bill and we left, immediately outside the door was a taxi dropping a couple off and Helen jumped in, pulling me behind her. It was almost 5 on a Friday, not worth going back to the office. Helen gave the driver the address of my apartment block and said it was on the way to her home in the suburbs.

We talked about mundane things like life in the city on the short trip to my place. When the taxi pulled up outside, I didn't want to get out, but Helen said: "Can you show me your apartment? I'd love to see how my gift looks in there!" Then she turned to the taxi driver and asked if he could come back to pick her up in 20 minutes. It was all very smooth and innocent, and he could make of it what he wanted. But I was thrilled and scared by the insinuation she was making to me.

As soon as the door clicked closed in my second-floor apartment Helen said: "Strip!" Her voice was short and stern and almost cold.

We stepped into the living room, and I could see she was more than a little impressed as her eyes roamed around the room and the big windows even as I was nervously unbuttoning my shirt with shaking fingers. Her eyes were fixed on me as the pink lace began to come into view though. When my pants hit the floor, she had me take a spin and made an appreciative coo.

"My, My! You do make a pretty girl! Pink looks good on you, but then we both knew it would!"

My heart was pounding like a drum, and I nervously replied. "Thank you, Mistress!"

She visibly grew from my submission, and she moved close to me. She put her mouth to my cheek kissing me lightly, holding my other cheek in her hand, she cooed: "I looked at every photograph on your laptop, every pose you made, every outfit you wore, every website you visited, every video you watched, every dirty thought you put down in words! You have no secrets from me! You want someone to submit to, don't you Jamie!" Her hand was stroking over the lace of the bralette, my nipples were hard, and she was slowly playing with them. They were sensitive, it was incredibly arousing in a way I had never noticed before.

"Yes Mistress." I whispered.

"You are a very dirty little thing! You have a very dirty mind!"

"Yes, Mistress!"

Her hand was gliding lower, over the bare flesh of my slim tummy and then making me gasp as her fingers ran along the length of my flesh where it strained against the lace of the panties.

"You want release don't you, petal!" I could hear lust in her voice.

"Yes, Mistress!"

"How long has it been since you last dressed up?"

"Seven months, Mistress, since you told me not to!"

"How did you cope?" She chuckled, mockingly.

"It was hard mistress!"

"It still is!" She cooed into my ear as her hand gripped then squeezed me hard through the lace, making me moan in delight.

"How long since you had release?" She wondered.

"The same Mistress. I thought you wouldn't want me to!" I confessed.

"Oh my!" She marveled. "Your obedience knows no bounds!" Running her fingers along the shaft. "So, you saved this for me?" Down to my full sensitive balls, cupping them, caressing them through the lace.

I moaned again. "Yes mistress."

Her hand moved again cupping the bare flesh of my buttocks where the thong back left them exposed.

"Submission is an interesting concept! You've allowed me to control one of your most deeply ingrained urges even without me knowing it!"

Her fingers traced the lace where it delved down between my buttocks, making me moan again.

"You have some very kinky interpretations of submission, don't you petal!"

"Yes Mistress!" It came out almost as a whimper.

Her hand stroked its way up over my hip, up my stomach, gently stroking, then pinching, then twisting my nipple. As a gasp of lust filled pain escaped me her lips came down on mine. It was a brief chaste kiss but as she lifted her mouth she said: "I like it!"

Her hand went to my shoulder and then she was pushing me down onto my knees, her other hand lifting her skirt. "Show me!" She hissed. "Show me submission!"

I dropped willingly to my knees as she leaned back against the door frame. My lips immediately on the satin of her own deep purple panties just above the mound of her pussy making her groan. I kissed my way down over her pussy lips feeling wetness as my hands pulled down on the elastic, lifting my mouth as they fell to the floor where she kicked them off. Her hands on my head, pulling me back to her. My lips on her pully, my tongue lapping greedily along and between the lips making her moan and whimper. Then my tongue lashed across her clit and she groaned: "Oh yes, Oh fuck, Yesss! You beautiful little sissy! Lick me!"

I focused in on her clit flicking it over and over, running my tongue over and around it, my hands stroking and grabbing her smooth firm buttocks, pulling my face onto her mound. Her fingers grasping and playing though my hair sending every nerve ending of my own tingling as I reveled in the tasty slick wetness of her sex. She was groaning and moaning above me, her hands more desperate with every lap of my tongue, gripping my head, riding my face, writhing against me, a squeal of ecstasy rising out of her as my tongue flicked over the hard nub of her clit over and over, faster and faster.

"Ohhhhhh, Yessssss, Fuck Yesssssssssss!" She wailed as her orgasm crashed over her. "Yessssssss."

She held my head as I lapped slowly over her pussy lips up to her clit again slowly, again and again, little aftershocks rolling over her. Then, almost suddenly, she pushed me away with a gasp of "Enough!"

Her skirt fell, and I lost sight of the beautiful sex of my beautiful tormentor. I looked up into her face and she looked a little stunned.

"Damn you're good at that!" she groaned. Then she looked down. My panties tightly stretched over the hardness within. Leaning back against the door post she lifted a leg and traced the length of me with her toes.

"It seems you enjoyed it almost as much as I did!" She said with a little grin, regaining her composure. She reached down and stroked my head.

"Mmmm, you'd like to cum too, wouldn't you petal!"

"Yes Mistress!" I croaked with a hoarse voice, surprised I hadn't done already, as wound up and turned on as I was.

I whimpered as her big toe rubbed over the head and she took that as a sign. Concentrating there with her toe as I pushed my hips forward to intensify the pressure.

"Oh, you are a needy little slut! But then you have been good. You deserve a reward."

The friction increased as her toes stroked over and over across the sensitive head. I could hear myself moaning and her words cascading over me. I ran my hands up and down her sexy legs, thrilling at the feel of them on my hands and arms.