Game Of Chance For A Mistress

I was doing some internet searches late at night, checking porn websites for later exploration. I typed in female domination and scrolled through the suggestions. Mostly there were clips sites and the occasional sign up site. On the bottom of the third page, just as I reached my limit of interest I was intrigued by a site that presented an interesting proposition. I could not resist looking at it.

I answered a basic profile questionnaire to get in. I lied mildly (wrong birthdate, slightly different spelling of my name) just in case, but I did put in my correct location just in case it was legitimate. I did want to try this.

The instructions were simple. Answer yes or no to a list of fetishes and limits, then move to the page of non-professional dominatrices. Select either three or six based on photographs they had supplied or by profiles put up by them. Why three or six? Each photograph or profile was assigned either one of two numbers on an electronic dice, though you did not know who was who. You rolled the dice and it tumbled away, eventually giving you a number to be used as a reference, along with the time and date. An email would follow.

Thirty minutes later a message appeared instructing me to be at 26 Jones Street at 9pm on Friday night. I was not to cum before then and I was to shave my cock and balls before coming. I was to be on time. Failure to do any of these things would terminate the assignation straight away. How she would know that I had cum during the three days I had to wit I don't know, but I guess they were playing on your need to be submissive.

-o0o-

I arrived at five-to- nine and waited in the car. Right on nine I rang the doorbell. After waiting for a minute the door swung open and I was face to face with a tall, athletic blonde dressed in tight jeans and a t-shirt. Her hair was quite short and her green eyes were radiant with anticipation.

I didn't recognise her face, but then the three photographs I chose did not really give that much detail of the particular ladies. The photos I picked were a close up of a hand holding a pair of nipple clamps and clutching a crop, a shot of a torso wrapped in a black leather corset that hinted at rosy nipples and a few stray black pubic hairs, and finally a photograph of a naked back with long dark hair. I had rolled the first photograph, my domme for the night holding the clamps and crop.

"Hi, my name is Alexis. Come in."

"I'm James, happy to meet you."

"Join me in a drink James, while I ask you a few questions. White or red?"

"Red, thank you."

"So are you ready to serve me tonight? Did you shave? Did you cum?"

"Yes. Yes. No."

"Okay, that's good. Are you hard at the thought of serving me?"

"Yes."

"Yes, what?"

"Yes Mistress."

"Do you have a big cock?"

"Average I think Mistress. What is big for you Mistress?"

"Ten inches. That is the last question you ask now. How big are you?"

"Seven or eight inches Mistress."

"I'll check that in a few minutes." Looking down at a sheet of paper Mistress Alexis continued "So I see you alright with some impact, anal, some cbt and sex. No to blood, medical and needles. Shame, some of those I quite like. But we have enough to work with, at least for one session. Is there anything you would like to add or change?"

"No Mistress."

Alexis showed me to a small bathroom and told me to shower. If the water went cold I needed to get out fast because she was waiting for me. As it was I exited while the water was hot and dried off. I remained naked as instructed, and after I exited the bathroom I knelt and waited.

After a couples minutes I looked up to see Mistress Alexis, wearing a sheer black body suit, a pair of black patent high heels and a pair of hoop earrings. Her breasts were small with very small very erect nipples that indented the fine mesh of her outfit. I could make out her shaved mound, her tight lips starting to blossom with excitement. I looked up to her jewel like eyes.

She looked down at my hard thick cock.

"Like what you see?" she enquired knowingly. I could see her plotting her pleasure for the night while she took me in.

"Yes Mistress. You are extremely sexy."

"Okay, we know the basic limits, but I also use red/yellow/green as safe words. Are you familiar?"

"Yes Mistress."

"Explain it back to me."

"Yes Mistress. Green is good, yellow is close to a limit, and red is stop immediately."

"Good. Stand up."

Mistress Alexis moved over and cupped my balls. And squeezed.

She bit my earlobe before whispering "follow me."

She led me into a playroom and tied me to a wall. Next thing she was giving me a hard work over with a cat of nine tails. I lasted as long as I could before I exclaimed "yellow Mistress!"

Mistress Alexis kept going at the same intensity so I called yellow again. No change, so I yelled "red, red, red!"

She stopped, untied me, told me to kneel and watch.

Alexis sat in her armchair, and after popping her body suit to expose her naked mound she spread her legs, lubed a large black dildo and started to fill herself. After a few moments of watching her, imagining my cock sliding into her gasping cunt, I was almost wishing I hadn't called red.

Then she looked directly at me and sneered "this is what you missed out on. Leave now, and don't come back!"

I gathered my clothes and dressed quickly, and as I left I heard Alexis getting close to her orgasm.

-o0o-

When I got home I considered my position. One more try I thought, perhaps I would find someone as promising that would live up to that promise. It was a shame because Alexis was sexy as hell.

I logged onto the website and considered once again whether to select from photographs or profiles. I went photographs, and picked the two I had picked last time. Alexis' photograph did not come up as a choice. The third photograph I picked was a reasonably close picture of a red head's crotch with a box covering the delicate bits. Inside the black box were the words "Worship me!"

I had my three and so I rolled again.

Ten minutes later there was a text. "Send your address. I will see you tomorrow at 2pm."

-o0o-

At two o'clock there was a knock on the door. I opened it to find a casually dressed brunette asking for me by name. She was tall and wore loose fitting clothes. On her head was a cap and she sported sunglasses.

"I noticed a park about a block away. Let's go for a walk."

"Okay, but I am expecting someone right about now."

"That's me silly. I'm Jane, from the site." She rolled the reference number off her tongue, and then her face lit up in a radiant smile.

I must have looked confused. I explained I was not expecting an approach like this, to which she replied that she wanted to get to know me better before we got too far in. I briefly explained about Alexis, and Jane assured me her approach was different. She confided that she knew Alexis, and that she had a bit of a reputation for running multiple subs and being a bit rough.

I came to my senses, grabbed my wallet, keys and sunglasses and off we went. On the way we bought ice cream. By the time we sat on a shady bench I felt much better.

Jane pulled a copy of my form out of her pocket and asked me about each limit. I altered the impact play limit, because of what Alexis had done. I didn't totally dismiss it but it became a limit to be discussed on the day.

Jane talked about herself for a bit. She was a single mother who shared custody of her daughter. They had an agreement with a week on, week off system, and this was Jane's week off. She was back on Monday, leaving her today and tomorrow for playtime. She had developed a thing for femdom at university. She had shared a house with another girl who dominated her boyfriend. Jane had developed a thing for Vicky, and had agreed to "cuckold" her boyfriend. Watching Vicky work him over and then have oral, vaginal and anal sex with her had opened Jane's eyes to a new world. She had played a bit but after she started seeing Miles that all stopped. He was very vanilla. Her pregnancy and subsequent break up had stalled this part of her life but she had recently settled in to a new house and a new job, and was ready to explore her neglected sex life. I was the third submissive she had met, the first two finding her a bit too relaxed.

"They should go to Alexis then," I observed.

"Perhaps they will draw her. As for me I had fun on the night, played with some hard cocks, had a couple of good orgasms and moved on happily. I don't think I'm looking for marriage or to settle down, but who knows what will come? I would like to develop a relationship of sorts to see how it goes. If I was only after a single session you'd be on your stomach with a dildo in your arse right now."

"Sounds like fun, if a bit fast. I am happy to try the longer game. How about we have dinner tonight and see what happens? I'll book something and send you a text."

"Sounds good, though don't start imagining you will make many choices." I knew it would be good when she laughed.

"I'll book somewhere nice so we can both dress up a bit."

"Okay, but I expect you to be wearing a cock cage. Present the key to me in front of our waiter tonight."

"Guess I am going shopping this afternoon. Anything else?"

"Clean sheets, your preferred lube and a nice red wine. We'll take it from there, depending upon how good the wine is."

"Sounds good. Will I send you a text with the details for dinner, or can I pick you up?"

"Send me the name and address and I will let you know."

"Eight okay?"

"Yes."

"Thank you Mistress Jane."

"Welcome. Also, I am only Mistress Jane in the scene, not when we are socialising like this."

That was unexpected, but also very nice. Jane had a relaxed manner that Alexis certainly did not display to me.

"How will I know?"

"Oh, you'll know. I'll wait for your text. By the way I don't know how big your cock is but make sure the cock cage fits snugly but isn't too tight. You might need to wear it for a while. I will mark it out of ten when I see it. The difference between your score and ten will determine a punishment."

"Huh?"

"If I think the harness is worth six the punishment will be worth four. That might be four anal fucks or denial of four orgasms, or it might be not so bad."

"Got it."

"Going now. See you tonight."

Jane left and I prepared to leave. I had some shopping to do, starting with the cock cage. I went to an adult shop in a neighbouring suburb. A nice Goth girl took great pleasure in fastening the wire cock cage on me. It was chromed and snugly held my hardening cock. She made sure it worked by whispering nasty suggestions in my ear and guiding my hand to her pierced nipple. "If she doesn't want you come back and I'll find a way to use this that you haven't thought of."

"Threat or promise?"

"Both" she replied, glint in her eye.

"I might take you up on the offer. What do you covet in this shop?"

"I like these earrings" she replied, pointing to some silver studs shaped like cat of nine tails. I bought them and presented them to her as a gift. I also found a polished metal butt plug that I thought might make a nice gift for Jane, and hoped I would actually experience sometime in the future.

After I getting her name, Brigid, I left to finish my errands. To the chemist for lube, to the bottle shop for a very nice merlot. To go with this I bought some nice cheese and biscuits. I also called one of my favourite restaurants, a discrete modern room with good food and professional service. I had not been there since I broke up with my last girlfriend, but I did fondly remember the food and atmosphere. I booked and sent Jane a text. She replied, asking me to meet her there.

I went home and spruced up for the night ahead.

-o0o-

I arrived at five to eight. Jane, as was her want, had not arrived by quarter past. It was nervous twenty minutes for me, especially as an attractive waitress checked several times about whether I needed anything. It was almost as if she knew. Suddenly there was a commotion and a swirl of red brought Jane to our table. Wow. Tall as I remembered and as pretty as she had been earlier, she was now extraordinarily sexy to me as well. Yes, I am shallow, and was looking forward how the night would unfold. Jane wore a red dress, black tights, black ankle boots and a red cape.

I stood to kiss her and we sat. After a quick glance at the menu and winelist Jane called the attractive waitress over and ordered our dinner. She chose salad, followed by beef and roast vegetables. And to drink a glass of prosecco to start and a hairy chested shiraz for the main.

We chatted amiably until the waitress came over with the prosecco. Jane glanced at me and I produced the key. I handed her the key and exclaimed, "here is the key to my new cock cage. I hope you find it satisfactory."

"I will tell you later." I noticed the waitress's draw drop. I figured, why not drive it home.

"Mistress, I also bought you a present" as I produced the box containing the butt plug. Jane opened it and praised my gift, further surprising the waitress.

The waitress left, returning several minutes later with the salads.

Jane introduced herself, introduced me and apologised for shocking her. Jane then asked for her name.

"Mandy," she replied. She went on to explain that she was less shocked and more intrigued. Jane asked what time Mandy would finish, and arranged to meet for a quick coffee.

As we ate we talked more about each other, and our desires. I explained that I was looking for something different, to stretch myself because I had a bit of a kinky side that had so far only been explored theoretically, largely through watching and reading porn. Jane said that she had felt a certain kinkiness from quite a young age, and that it had blossomed in adulthood. She didn't need it all the time but got a tremendous feeling of satisfaction when she was in the mood and she had a sub to play with.

"Are you in the mood tonight?" I asked, hopeful and fearful at the same time. She had a lot more experience despite her laconic nature.

"Maybe, she replied. "I am certainly excited, but I am still weighing up the possibilities. I know you will do what I need because you have already, but I am wondering about whether Mandy might be fun to play with. It' s been a while since I have had a woman's touch."

"Where does that leave me?"

"Maybe it still means I play with you tonight. Maybe you get to watch. Maybe we play tomorrow. Or, if you become petulant, we call it quits after dinner. This is a decision that will be made based upon my mood, Mandy's reply and your actions. My suggestion is that you get on board, and then we will have a good time. It might not be exactly what you imagined, whatever that was, but it will be entertaining and you will probably get off. Alright?"

"Yes, Jane. As you wish."

Jane signalled to Mandy and requested dessert menus. When she brought them Jane asked if she was an option? Mandy blushed, so Jane asked her to bring us two chocolate fondant puddings and two macchiatos. And her panties.

Mandy put our order in and disappeared off the floor. Five minutes later she returned to our table with our coffees. After placing them on our table she reached into her skirt pocket and pulled out a lacy white G-string that she gently placed on the table in front of Jane. There was a long silence as Jane considered the underwear and then looked at me.

"How is your cock going?" she enquired rhetorically. She knew I was in pleasurable agony that she increased by asking me if Mandy was shaved or had a bush. I looked at Jane, who smiled at me. I knew what I had to do, and so I reached under Mandy's skirt. She flinched slightly as I ran my hand over her mound.

"Trimmed bush" I announced.

"Good" replied. She turned to Mandy. "Does the collar match the cuffs?"

"Yes, I am a natural redhead."

"Want to play tonight?"

"Yes please. I finish at 10."

"Do you have a car?"

"No, I walk to work."

"Tonight you'll have a lift. Are you a sub, domme or switch?"

"I don't know. It's just that I like girls sometimes."

Mandy left the table and Jane and I looked to each other.

"The way I see this going is that you will submit to me and I will fuck Mandy while you watch. If you are very good you might get off. How you react to this will determine whether we see each other. And beside, doesn't Mandy turn you on?"

"Yes, she does. I was caught by surprise is all."

"To be honest I didn't plan this but why not roll with it? She is hot and while I am away she might be fun. Let's see what happens."

We finished and moved outside to wait. While we stood in the carpark Jane moved in to kiss me. That was nice, and then she grasped my balls. She gave a slight tug as she looked into my eyes demanding my will. Her had moved up and grasped the cock cage. She unzipped me and pulled it out in the car park. Luckily for me that it was a bit dark and deserted. Jane looked down and whispered "seven." That meant a punishment of three of whatever Jane decided.

"I'm feeling generous tonight. Three orgasms while nipple clamps are in place is the starting point."

Mandy came out of the staff entrance. Jane waved and she joined us.

"We will go to Mandy's so she can change, and then we will see you at your place. Go home, get naked and wait. Don't forget the wine. We won't be long," Jane told me. Looks like I was spending the night with two hot women, one of who had my balls right where she wanted them.

-o0o-

About an hour later the doorbell rang. I answered it quickly, kneeling as I opened it to Jane and Mandy. Jane told me to stand. She admired my now quite abused cock as it pressed hard against its chrome prison. Jane had changed slightly, the tights removed and the boots now knee length. Mandy wore a black t-shirt, flowing black skirt and a pair of ballet flats. She carried a box that she put down as she entered.

Jane turned to Mandy and asked her if she would submit. She nodded her agreement.

"Good. This will be fun for all of us. Strip!"

Mandy shucked off her clothes to reveal a trim taught body with perky breasts topped with pale pink nipples and a full auburn bush.

Jane briefly explained limits and safe words and then we started playing.

"James, I need two things from you. The first is the tweezer nipple clamps from my toy box. The second is a glass of the red wine."

I found the clamps and handed them to Jane. When I returned Mandy was grimacing slightly as she got used to the clamps. Jane walked behind her, nuzzled her neck and stroked her cunt. Jane lifted her hand to show the glistening result. She pointed at me to kneel in front of Mandy.

"Eat her." I worked Mandy the way I normally eat a lady, soft and gentle long strokes that gradually shorten and become a tight figure eight action around the clitoris. It wasn't long before she crumpled as I drove my tongue across her nub. As she came Jane removed the clamps, sending pain and ecstasy pulsing through Mandy simultaneously.

I moved back. Jane looked at me with a glint in her eyes. "Very good. Remember your punishment? One down, two to go. My turn for an orgasm. Let's see what you two can do. James, please turn the lights right down and put on some soft jazz."

This was the weirdest femdom scene I could imagine, yet she had both Mandy and I enthralled.

I put on some gently spiralling saxophone jazz then switched on a lamp on a side table. Once the overhead was off there was a warm glow in the room.

Jane moved to Mandy and kissed her. I moved in and eased down the zip of Jane's dress. Mandy stepped back for a second to let it slither to the floor. Jane stood in her boots and boy leg panties. Her beautiful puffy nipples were quite pronounced and beginning to harden to excite points.