Picking up guys in bars

This is a true story, or as true as I remember it. I’ve changed some of the names, for obvious reasons. My name isn’t Jenny, my boss isn’t named Cynthia, and the club in question isn’t called Club San Limites, but the club does exist in downtown Montreal under a different name. I’ve also omitted some details like what industry I work in and where what city I live in. It’s not like I’m famous or anything, but it’s a small industry and those who work in it could probably identify “Cynthia” and me from details like that. But those details aren’t important to the story, so leaving them out won’t affect anything.

That trip to Montreal changed my life. It opened me up to a world that I was only vaguely aware existed, and more importantly, it led me to discover who I am sexually. I’d been to Montreal before; we have a major client located there, and I’d been working on that account for two years, but this was the first trip to the city on my own. I was taking over management of the account from Cynthia, my boss. It was my first big promotion, and I was excited.

Even better, before we got to Montreal we had a stop in New York to see another client. Cynthia was along for that leg of the trip. I was twenty-five years old and this was my first trip to the Big Apple. We spent the day in meetings and at dinner with the client, so I didn’t have much of a chance to see the city, but that didn’t matter. I was in New York, and that was thrill enough. Then I was up before dawn to catch the first flight to Montreal.

And to make things even better, Cynthia had suggested I stay the weekend in Montreal, even going so far as telling me to expense the weekend hotel bills, saying I would be spending a lot of time in Montreal, so I should get to know the city on the company’s dime. She said I could consider it sort of a bonus for working so hard over the last year. Cynthia is great like that. She’s demanding and makes you bust your ass, but she also knows how to reward you. I loved working for her, and she’d taken me under her wing as a prot,g,.

A few weeks before the trip, I had half-suspected that Cynthia was interested in me sexually. Now, I had wondered about her sexual orientation before–she was forty-five and never married, never bringing a partner, male or female, to any corporate social event–but I actually knew almost nothing about her personal life. Cynthia is scrupulous about maintaining a professional demeanor. What made me suspect she might be interested in me was that a few weeks earlier she had cracked that professional barrier and asked about my social life, in particular whether there was a guy in my life.

There’s not, at least not any one guy. I’ve got a couple of friends who provide benefits and are usually available for late-night booty calls, and when the urge is overpowering and my friends are otherwise engaged, I just go out to a bar and pick a guy up. I don’t want to sound conceited or anything, but I’m good looking and finding a guy for a roll in the sack just isn’t a problem. My priorities right now are work, the gym, and nights out with friends. I’m twenty-five. True love and finding the one guy to spend the rest of my life with can wait a while.

Anyway, Cynthia seemed surprised when I told her that I didn’t date much, telling me that should be more adventurous–for obvious reasons I didn’t tell her about picking up guys in bars. I remember her exact words because they were so surprising, “at your age you should be exploring your sexuality. You need to find what excites you, what turns you on. If you’re into being tied up, you should be learning how to tie knots. If you’re into women, you need to be discovering that.” Up to that point, the conversation had been one I could have had with any of my girlfriends, but it was that statement that led me to think she might be interested in being more than just a friend.

That isn’t the sort of thing that bosses, especially bosses as savvy as Cynthia, say. Told to the wrong person, it could be the basis for a sexual harassment suit. Not that I took offense. In fact, I thought I might be willing to have fling with Cynthia if she asked. I didn’t think I was really into women, but I’d fooled around with some of my girlfriends once or twice–nothing major, just some kissing and fumbling about–but Cynthia is quite attractive, and despite what she thought, I could be adventurous–more adventurous than even I knew, as it turned out. I’d often wondered what real sex with a woman might be like and was willing to try it under the right circumstances. But nothing came of the conversation, and by the time the Montreal trip rolled around I was convinced that she had been just trying to be a friend and had been extending her mentoring role into my social life. I figured that she didn’t want me to make the mistake she had made and end up being forty-five and alone, without even a girlfriend to talk to about men and sex.

Cynthia was beautiful, elegant, and had a winning personality–she could charm just about anyone. She was also rich, having been with the company since its founding and had made a fortune when the firm went public. But she still worked harder than anyone else in the firm, continuing to bring in millions in new business to the company, and that kind of dedication came at a cost. As far as I could tell, she had no social life at all. She was at the stage in life where she would be justified in powering down, reducing her hours, and delegating more work to her employees, but she remained as hard charging a businesswoman as ever. She lived for work.

Anyway, all that was going through my mind as I took the elevator up to my hotel room. The meetings that day with the Montreal client had gone really well, and I was looking forward to a weekend of exploring the city. It was snowing, but Montreal on a Friday night, even a snowy one, would be fun.

Once I got to my room, however, I saw the bag sitting on the bed. It was black leather, Coach, and thus expensive. It had a tag on it that read, “To help you enjoy the weekend.” No signature. My first thought was that Cynthia had arranged to have a present delivered. But then I opened the bag.

It was some kind of sick joke. Inside was a kinky sex kit. There was a leather collar; some sort of leather body harness; a pair of elbow-length, black gloves; and a pair of black leather, above-the-knee boots. There were two vibrators, one like the one I, and every girl my age, has at home and another smaller one, a pocket rocket for the clit. Some of my girlfriends told me those pocket rockets were absolutely great, but that I’d never tried one. There was also a huge dildo made of black silicone. It was about nine inches long and thicker than any cock had the right to be, and came with a corresponding strap-on harness. There was also a double-headed, silicone dildo. The sex toys were all in their original packaging, and to top it all off, the bag contained an assortment of lubes and body oils. There was also an envelope inside that contained some kind of membership card. It read, “Club Sans Limites, Member # A0154, if found, please return to…” and there was a Montreal address and phone number. It didn’t take a pocket-rocket scientist to figure out that the Club San Limites was some kind of sex club.

I knew right away that Cynthia would never give me something like this. Either this was an over-the-top prank by one of my friends or I had some pervert for a stalker. All my friends knew I was in Montreal for the weekend, as did everyone at work, plus a bunch of my clients. Any of them could easily have found out which hotel I was staying at. I couldn’t think of anyone at work who would send me this, and while some of my friends aren’t above playing pranks, this went beyond anything they might do. Not only did they not think like this, none of them would spend this kind of money on a prank–I didn’t know how much sex toys like this cost, but they looked expensive, and I do know how much a Coach bag costs; the bag and its contents easily cost six or seven hundred dollars.

But then I realized there were a few other people who might have sent it–the clients I worked for here in Montreal. There were two partners who owned the company and either one could easily afford this, and they might know about the club, given that they lived in the city. They were both older men, in their mid-fifties. I knew John the best. He was a really sweet guy, but not the kind of guy you’d expect to be a member of a kinky sex club. He was a jovial, pudgy guy who was always going on about his family and kids and the charity work that he threw himself into every spare minute he had. And he had never shown the slightest hint that he might be seriously interested in sex with me–or anyone else, for that matter. He’d have to be an amazing con artist to have a secret kinkster identity. Keith, the other partner, was another matter. His responsibilities in the company didn’t overlap with my work, so I hadn’t had many dealings with him. I knew nothing about him except that he was divorced. It’s possible he could be harboring a secret thing for me and this was his way of letting me know. Keith wasn’t a bad-looking guy, but not really my type, and I would never sleep with a client anyway. And anyway, any guy who pulled a stunt like this to get my attention would be scratched off my list. It was just too creepy.

That left the stalker theory, and that wasn’t a comfort.

I called the front desk and asked who had delivered the bag. After a few minutes, the desk clerk called back and said that the bag had been dropped off by a messenger service with instructions that it be delivered to my room at check-in. He was sorry he couldn’t be of more help.

I flipped open my laptop and Googled the name of the club. There were only a few hits, all business directories that gave the club’s address and phone number and said only that it was a “private club.” Whatever this club was, it didn’t have a web page and its members didn’t talk about it on the net. I next went to Google Maps and looked up the address. It was on a side street, a few blocks from my hotel. The street view showed that it was on a respectable street, lined with a mix of offices, cafes, and shops, but at the club’s address all I could see was a blank door and a small sign with name of the club. So the place existed, but was very discreet, whatever it was.

I decided that, prank or pervert, I wasn’t going to play the game. So I put the bag aside and started unpacking my clothes and thinking about plans for that evening. The snow would limit my options, but maybe the concierge could direct me to a decent bar or club. But my thoughts kept drifting back to the bag and what kind of establishment the Club San Limites was and how much whoever sent it knew about me.

I opened the bag again and checked the sizes of the boots and clothing. They fit me. That made me more nervous. Someone who knew my shoe size had gone to great trouble and expense to lure me to this club. And the really troubling thing was that it was working.

My curiosity won out. I knew that if I didn’t go, I’d be wondering the rest of my life what the hell had been going on. I might as well check out this club to see if it was what I thought it was and if someone had really given me a membership to it. I had nothing better to do that evening, and it would be an adventure. I thought about the risk, but it seemed minimal. The location was public. It’s not like I was going to go walking down a dark alley. And if anything looked sketchy, I could just turn around and leave. So I put on my coat, picked up the bag, and headed down to the lobby to catch a cab to the club.

It wasn’t snowing all that much, but the streets were deserted already, even though it was only just after seven on a Friday night. It only took a few minutes to get to the club’s address. The street was mostly empty, the offices and cafes, which catered to the lunch crowd, were closed. There were a few people hurriedly walking past though, so it didn’t seem particularly ominous, and I noticed a corner bar down that block that I could use as a refuge if things got scary. After the cab drove off I stood in the snow for a moment, screwing up the courage to open the door. Then I walked up the three steps to the door, opened it, and stepped inside.

The foyer looked like the entrance to an upscale restaurant, with dark wood paneling and plush carpeting. There was reception station, staffed by a young woman, about my age, wearing glasses and with her hair bound up in a bun. Vaguely pretty, she didn’t have the appearance of someone who would be working the door at a sex club. She looked like a no-nonsense schoolmarm.

“Bonjour,” said the woman.

Unsure of what to say, I just handed the woman the membership card. The woman looked at the card and then punched something, presumably the member number, into the reception station’s computer.

“Good evening, Ms. Loring,” said the woman, in accented, but perfect English. “Welcome to the Club Sans Limites. I’m Helene, the hostess for this evening. If you require anything, just ask me or any of the staff. We’re here to make your visit exciting and pleasant.”

I was about to explain that I had been given the bag and card and had no idea what the club was, but the woman just continued.

“Since it’s your first time, I’d like to give you a tour of our facilities and explain how we operate. I’m sure you’re familiar with it from our correspondence and from the friend who nominated you for membership, but we always like to go over the details with those coming here for the first time. We find that making sure that there are no misunderstandings in advance makes for a more enjoyable evening.”

Again, my curiosity got the better of me. I would take the tour and then leave. I had idly wondered what went on in sex clubs before–and by now I was pretty damned sure this was a sex club, a very upscale sex club–and this would be a no-risk way of finding out. Besides, tonight would probably be my only opportunity to ever step foot in a place like this. I might as well see what was beyond the reception station. I found myself smiling and agreeing to the tour.

Helene took the bag from me and handed it to another woman, and then she and I started the tour off with the changing rooms, which were on the first floor. There were a lot of them, at least twenty. Each had a locker, a shower and toilet, and a small bed. Helene explained that members often chose to sleep a few hours in their changing room before heading home in the morning; it was a private place to prepare before the evening’s “entertainment,” and for recuperating afterward. One of the club’s few rules was that the “entertainment,” as she kept calling it, was not to occur in the changing rooms. There were beds upstairs that weren’t for sleeping.

She then took me upstairs. On the second floor there was a small bar and some staff were setting out a light buffet supper. Helene explained that drinks were available, but that most members refrained from anything more than a glass of wine or two. “It blunts the abilities,” she explained. The same went with the food; a heavy meal “interfered with the fun, but you need something to keep the blood sugar up.”

Next up was the common room. It took up most of the second floor and the ceiling extended up through the next floor. It was designed around a large sunken pit with couches around the edge. There were that various restraints, cages, and bondage devices scattered throughout the room. There were a few chairs with stirrups and arm restraints, a couple of sex swings, and at the very center of the pit was what looked like a vaulting horse, but had shackles for arms and legs; it was clearly designed to have someone bent over it and tied down. I had seen pictures of such furniture on the internet, but I never dreamed I would actually see them in real life. No one else was in the room, and Helene explained that things usually didn’t get started until after nine. I asked how many would normally be here on a typical Friday night and she told me that some twenty or thirty club members might be there on weekend nights, but that she didn’t expect that many tonight because of the snow.

“Of course, we have our entertainment staff to supplement the guests,” explained Helene. “So you don’t have to worry if it’s not crowded. There’s always someone to play with.”

“Do you…?” I asked. She didn’t look like a prostitute, or at least how I thought a prostitute should look. Regardless of the euphemism “entertainment staff,” prostitutes were what they were. Maybe exclusive to the club and probably well paid, but prostitutes nonetheless.

“Oh no,” replied Helene. “I’m not entertainment staff. I keep the club’s books and some nights I’m at the reception desk.” She reached out and gently stroked my chin. “But sometimes I make an exception for special members. Just for fun.”

I felt a knot begin to form in my stomach. Perhaps my little game had gone on too long.

But the tour continued. On the floor above were private rooms. They ran along one side of balcony that overlooked the big common room below. The rooms were decorated in various themes, accommodating almost any fantasy one could think of. Some imitated decor from around the world; there was an Egyptian room and a Japanese room, for instance. Others were outfitted as dungeons. While the decor choices were varied, they all exhibited good taste, if you could call it that. What I mean is that there were no velvet paintings of naked women or porn films playing on large-screen TVs, the kind of things I expected to see at a sex club, and it was all very clean and well maintained. About half of the rooms had large Jacuzzis. Two of the rooms were basically big tiled bathrooms, for “water sports” explained Helene. I made a note to find out exactly what “water sports” entailed–when I did find out later on, I realized instantly that it wasn’t my scene at all, but to each her own. One room looked like a cheap hotel room, for “affairs” explained Helene. Another looked like a teenage girl’s room. “Schoolgirl fantasy” was the explanation. Some of the rooms had the doors closed. “Occupied.”

Helene explained that if you left the door open, you were open to others joining you. If you kept it closed, you wanted to remain private. “If you think you might like to join in,” explained Helene, “it is best to stand by the door until the occupants notice you. They’ll invite you in if they want you to join them. Don’t take it personally if you aren’t invited. It just may not be the right moment for them.” She took a long look up and down my body. “You won’t have any problems, though.” I get those looks from guys all the time. It was disconcerting to get it from this prim-looking woman.

We ended up back in one of the changing rooms, and I saw that the contents of the bag had been neatly laid out. All the items had been removed from their packaging.

“Now, I have to go over a few safety rules,” said Helene. “First, do not feel pressured to do anything you do not want to do. You decide what activities you want to participate in and with who; do not worry about what anyone else thinks, and feel free to say ‘no’ to anything you are not comfortable with. The safe word is ‘alabaster.’ If any of your partners say that word, ‘alabaster,’ stop what you’re doing immediately. If your partner is restrained, loosen the restraints as well. If at any time you feel uncomfortable or want to stop, just say ‘alabaster.’ Sometimes new members get somewhat scared their first time. Don’t be afraid to use the safe word, which is ‘alabaster.’ Sometimes it just takes a minute or two to compose yourself, or the activity is just getting a little too intense, and you can continue in a few moments. And don’t worry, we’ve never had a problem with a member ignoring a safe word. Everyone here is very considerate.” Helene went on to explain the hand signals that were to be used in lieu of a safe word when either I or one of my partners were gagged. Then she made me repeat the safe word and make the hand signals. Finally she said that at the end of the evening, if I wished, I could leave the bag in the changing room and all the gear would be cleaned and held until I visited the club again. All I need do was call ahead, and everything would be prepared for my arrival.

“Since the club is rather quiet right now, you’ll probably want one of the staff to warm you up. You’re new, but do you have anyone in mind?”

“I really don’t know…”

“Of course, I will pick someone out for you. I know just who will be right for you. Get changed and someone will be here to take you up to one of the rooms shortly. Prenez du bon temps!” And then Helene was gone.

I just stood there. I knew I should just walk out, but I couldn’t make my legs move. From the moment I had arrived at the club, I had started to become excited. I could feel that warm, nervous ball in my gut that glowed whenever I anticipated sex. I didn’t start with any conscious intent of staying and having sex, especially kinky sex, but as the tour had progressed I had gotten hornier. Now the desire was overwhelming. I found myself undressing and taking a shower, after which I started to get into the leather outfit. I fumbled a bit with the harness thingy, trying to figure out how to put it on, but I got it after a minute. I fastened the leather collar around my neck, laced up the high boots with the spiked heels, put on the gloves, and looked at myself in the mirror–I looked good; the black leather contrasted with my pale skin and matched my dark hair, the harness accentuated my breasts, and my lanky body in that outfit simply screamed “mistress of pain.” For once my height and smallish breasts–I’m 5′ 9″ and a B-cup–were working for me. But something was off. It was the hair. My shoulder length hairstyle just didn’t fit with the costume, so I tied it back in a ponytail. That was better. Not only did the ponytail make me look more like a “dominatrix,” but it got it out of the way and more practical–although while I may have looked the part, I had no idea how to act like a dominatrix or even any idea if I wanted to. Then a knock came at the door and I was past the point of no return.

I opened the door to find a very beautiful woman clad in a leather corset, garters and stockings. She had a collar around her neck. She was a bit shorter than me, but curvier, with a bigger bust, and light brown hair.

“I am Celine, Ms. Loring. Do you have a particular room preference?”

“Nnn…no,”I stammered. “Any one will do fine.”

“Let me get your things then,” said Celine, who picked up the various toys and bottles of lube and placed them in the bag. Then picking up the bag and taking me by the hand she led me upstairs.

I found myself in the Japanese room. Tatami mats covered the floor and most of the walls. There were some paintings of some traditional Japanese nature scenes on the walls as well as some hangings with calligraphy on them. The room had a large king-size bed, a Jacuzzi, and various restraints hung from the ceiling and some of the walls. The wall opposite the bed was dominated by an x-shaped cross with hand and ankle cuffs. I wondered what the man that Helene had picked out for her would look like and whether or not he would be gentle. Helene clearly thought that I was more adventurous than I actually was, and there was no telling what kind of person Helene would think was “right” for me.

Celine busied herself taking toys and lube from out of the bag and laying them out on the bed. Then she crossed the room and embraced me.

“Now what kind of things do you like?” asked Celine.

“Um, I thought you were going to be a man…”

“Would you like me to get one of the boys? I won’t be insulted or upset if that is what you prefer.”

I flashed to what Cynthia had said to me, about exploring my sexuality. This might be the moment to play with a woman. No strings. No one else would ever be the wiser.

“No, no. I’m just a bit surprised,” I found myself saying.

“Good,” said Celine. “When I saw you I thought it would be my lucky night. Helene is good to me. We’ll have a lot of fun together, and later on we can find some men if you wish. Now, you’re here, so you’re not vanilla, but are you mild, edgy, or hardcore?”

I was about to reply “mild,” but I checked myself.

“I like edgy, but nothing extreme,” I ended up saying. “And no pain,” I added at the last minute.

“I understand. I am sorry for all the questions, but one more. Are you dom or sub?”

It was time for a bit of honesty as it would be readily apparent in a few minutes that I had no idea what I was doing.

“I’m still kind of new at this. Maybe you’d better take the lead.”

“Certainly. I will take charge, but your wish is my command.”

With that she put her hand behind my head and drew my lips to meet her own. Ever so gently, she started to part my lips with her tongue and soon we were engaged in a fierce exchange of tongues. Then Celine broke off the kiss, nipping at my lower lip as she did so; not hard enough really hurt, but just hard enough to let me know that she was not all sugar and spice. A chill run down my spine when I felt that slight pain. It was a level of eroticism I had never before experienced. And the fact that it turned me on scared me more than a little.

Then she began to maneuver me backward, toward the bed, pushing me down onto it when we reached the destination. Celine jumped on top, straddling me and began nipping at my breasts, shoulders, and neck. I started to block her, but Celine grabbed my wrists and pinned them to the bed above my head. I was now relatively helpless and another thrill ran through me when I realized there was nothing I could do to stop it. The biting continued. I just put my head back and let it happen.

Celine alternated nips and kisses. When she bit my nipples, which are especially sensitive, it was an unbearable joy. The moment of expectation, not knowing what was to be delivered. Would be a kiss or a bite? The anticipation was excruciating. But while the nips and kisses, and the delays between them, were exquisitely pleasurable, I was frustrated. I couldn’t move my arms, and as attentive and skilled as Celine was, my inability to move made me uncomfortable.

Celine noticed. “Would you like me to stop?”

“Just release my arms, please.” Celine complied. “The rest of what you were doing was very nice, though.”

“Would you like to be on top? Perhaps you are a bit of dom. You like to be in control, yes?” said Celine having diagnosed the cause of my discomfort better than I ever could have.

“Yes, please.”

And with that, Celine gave me another kiss, and rolled over onto her back, pulling me on top of her.

I felt like the dog who caught the car. I was suddenly at a loss as to what to do with my new plaything.

“Would my mistress like to restrain me?” prompted Celine, turning her head to look at one of the corners of the bed. I noticed that at the four corners of the bed there were padded leather cuffs with straps attaching them to the bedposts. I quickly moved to secure Celine’s wrists and ankles, and in a moment she was spread eagle on the bed, her breasts heaving.

“Would my mistress like to know if I’ve been a good girl?” she prompted again.

I reached out my hand and tweaked her left nipple. “Has my plaything been a good girl?”

“Yes, mistress.”

I slapped her left breast. “I don’t believe you.”

“But I have been, mistress.”

Slap! To the right one this time.

“You know I don’t like it when you don’t tell the truth.” I was astonishing myself. I didn’t know where all this was coming from. And I could feel myself starting to get wet between my legs.

“I swear, mistress, I haven’t done anything wrong.”

Slap! “Didn’t you just try to dominate your mistress?”

“Yes…but only because I thought that’s what you wanted, and I didn’t know the rules. Please don’t punish me too harshly.”

“Maybe I’ll be lenient this time, but you will have to be punished. I’m not going to let you cum, at least not right away. Is that fair?”

“Yes, mistress.”

“You’ll have to pleasure me, though. And if you do a good job, I’ll think about letting you cum.”

With that I offered my left breast to Celine’s mouth, and she eagerly started to suck and tongue the nipple. Her mouth on my breast felt even better than when I had been the one restrained. After a few minutes I switched and offered her my right breast, which she eagerly attacked as well. She took another nip at my nipple.

Slap! I brought my hand down on Celine’s pussy, causing her eyes to open wide with surprise.

“Tit for tat. If you try to hurt your mistress, she will punish you. And remember, she’s the one in control.” Much as I had liked the nips, this control was better.

“Yes.”

Slap!

“Yes, mistress.”

“For that insubordination, you’re going to have to eat my pussy.” With that I straddled Celine’s head and lowered my pussy to her mouth. For the first time, I felt a woman’s tongue down there, my earlier fooling around with my girlfriends never having progressed this far.

But I quickly found that Celine was far more skilled than any man I had ever been with. This dominance thing had come out of nowhere, and I really had no idea what I was doing, so far having made it up as I went along. I had hoped to use the opportunity afforded by my sitting on her face to figure out what to do next. I really was at a loss. But Celine’s skills were too much for my brain to cope with, and I couldn’t think what to do next; I was too distracted by the pleasure she was giving me.

She had started by parting my labia with her tongue, taking long licks from down below and ending just shy of my clit. Then she started alternating those licks by taking my labia between her lips and tugging and squeezing, which indirectly started stimulating my clit. Then Celine raised her head and started swirling her tongue around the bud of my clit, zeroing in on it, until she took it between her lips and started sucking, alternating that with little flicks by the tip of her tongue.

I felt the orgasm begin, that familiar tingle in my feet that then moved up my legs, signaling that it was on its way and nothing would stop it. I felt detached, almost like an out-of-body experience, like a wave of pleasure had temporarily pushed me out of her body. I could still feel the pleasures of Celine’s tonguing, but I felt them at a remove. My breathing became ragged and labored. Then the wave of pleasure hit, traveling from groin to brain. I didn’t exactly pass out; I remained aware of what was happening, but it was as if my brain short circuited, losing all muscle control. I collapsed on top of Celine, eyes closed. It had been a good one.

The musky odor of Celine’s pussy brought me back to reality. It smelled good. Throwing the dominance scenario out the window, I just wanted to return the favor. But first I untied Celine; I wanted her unrestrained for this. As Celine moved her limbs and rubbed her wrists, I positioned myself back on top in a sixty-nine and started eating my first pussy.

Celine tasted good; her sweat mixed with the tart taste of her juices. It was not at all like a man tastes. This was less confusing than being the dom. While I had never gone down on a woman before, at least I had lots of experience being on the receiving end. If I just did what I liked to have done to me, I couldn’t be too far off. I focused my tongue on Celine’s clit, alternating licking and sucking, and ran the fingers of my right hand along Celine’s labia. She was wet. I penetrated her with one finger, then two. The angle was somewhat awkward, but manageable.

For her part, Celine began licking me again, and was rather successful at first, but as Celine’s own pleasure grew and I focused on her pussy, moving slightly to get a better angle, my pussy moved further and further away from her mouth. After a few minutes, she could only manage a few licks here and there. But I didn’t care. I had had my pleasure, now I wanted Celine’s too.

And I got it. After a few more minutes of this, Celine rocked with her own orgasm. And the two of us cuddled together and kissed.

“Wow! That was great,” said Celine, breaking the kiss.

“I had no idea what I was doing. That was my first time, both with a woman and with this dominatrix thing.”

“You could have fooled me.”

“I have so much to learn.”

“Well, you’ve got a good start…We have an audience.”

I turned and looked at the door, not realizing before, in all my nervousness, that Celine had left it open. A naked man was standing there, slowly stroking his erect cock. He was older, salt and pepper hair, in his late forties or fiftyish, but in good shape, and rather handsome.

“Would my plaything like a nice, juicy cock to play with, as a reward for giving her mistress such a wonderful orgasm?”

“Oh yes, mistress,” replied Celine.

I beckoned the man into the room.

“Suck his cock for me,” I whispered into Celine’s ear.

Celine stood up, met the man by the side of the bed, dropped to her knees, and took the cock into her mouth.

I lay on the bed watching, absent mindedly running a finger in a circle around my clitoris, and realizing that I wanted a cock now too. Watching Celine service this anonymous gentleman was exciting, but just watching wasn’t satisfying enough.

I stood up and stood next to the man, putting her arm around him, looking down at the gorgeous, curvy woman sucking his cock, occasionally kissing the man’s shoulder.

“Does he taste good?”

“Yes, mistress,” Celine said. “Would mistress like a taste?”

“In a moment. I just want to watch for now.”

I then noticed a movement by the door; another man was standing there. This one was younger, mid-thirties, blond with blue eyes. He wasn’t erect, but his cock looked large nonetheless. I beckoned him in too, dropping to my knees in front of him.

For the first time that evening, I was on familiar ground. True, I was engaged in a foursome in a sex club, and any moment others might show up to watch, but I did know how to suck cock. Cynthia had once told me that when confronted with a large task that you didn’t know how to begin, you should just find a small piece that you know how to do and start with that. For me that night, that small piece was sucking cock. But as I suspected, the piece was far from small. In fact the man was rather large, in girth as well as length. Not monstrous, but definitely in the category of well-endowed.

The man grew hard quickly, and I found I couldn’t keep the whole cock in my mouth. I licked down the shaft, and pushing the penis against the man’s stomach, I took his balls into my mouth, one at a time. I realized the man was shaved, surprised that I hadn’t noticed it before. It made licking his balls a lot easier and more pleasant.

But I didn’t want him to cum like this. I needed to be fucked. I stood up, and without saying a word drew my new partner to the bed. I lay down and looked up at him. He didn’t need to be told what to do. I closed her eyes.

I felt the head of his cock rub up and down my labia, as he found the entrance to my vagina. Then a gentle pressure and, large as he was, he slipped right in. He pushed slowly but firmly, until I could feel his thighs press against mine. He was buried inside me, filling me quite nicely. Then he started thrusting back and forth. I rocked my hips in sync with this thrusts, taking him as deeply as I could on each down stroke.

I felt a kiss on my forehead. It was the older man. He presented his penis to my mouth, and I took it in eagerly. Two men at once. Another first.

This was an amazing feeling, being doubly filled. Normally, fucking alone doesn’t bring me to orgasm. Don’t get me wrong, I like being fucked very much. Having a man inside you, being penetrated, is a wonderful sensation. But I have to supply some extra stimulation to my clit to reach orgasm. But these two gentleman really did it for me. The younger one was large enough that my clit rubbed the shaft of his cock with every thrust. It felt incredible. And the older gentleman was just the right size for my mouth. I could deep throat him with ease. So I had two men penetrating me to their full length.

I wanted it to go on forever, but of course it couldn’t. The older man came first. He was considerate and warned me, but I didn’t mind. I kept sucking. I don’t mind the taste of semen, although he produced quite a bit, more than I was used to. I gulped the cum down as fast as he could spurt it out. Then he softened and slipped out of my mouth.

I would have been sad that this particular combination was over for the evening, but that familiar tingling sensation in my legs didn’t give me time to think about it. Again the wave hit and my brain circuited. All I knew was pleasure.

When I could focus again, the younger gentleman was still pounding away, but I could tell by his face that he wasn’t far from cumming himself. I gave my hips a bit of a swirl and tried to clamp my pussy muscles down on him, to milk his cock. It seemed to work, he gasped and groaned. I felt him soften too and slip out of me.

The two men collapsed on either side of me, and we rested there a while, not saying a word. They ran their hands along my body, and we gently kissed. It was very nice.

I felt a third kiss on my forehead, and I opened my eyes, expecting to see Celine, but instead it was Helene.

“I see that you’ve enjoyed yourself.”

“Yes, Celine was wonderful, the perfect selection. Thank you.”

“Well knowing what our members want is my job.”

“So, you arranged all this?”

“Only Celine. These gentlemen are members, like you. They weren’t part of the plan, but that’s the wonderful thing about this club.”

“Well, thank you for everything anyway. You’re very good at your job.”

“But I am not working now.”

“You’re not?”

“No, and if you still have some energy left and perhaps you want to thank me in a different way.”

I smiled. “Did you have anything in mind?”

“Yes, I do.”

Helene smiled at my two companions, who got the hint and slipped away. I was sorry to see them go. We had never spoken a word to each other, and I didn’t even know their names.

Helene followed them to the door, and closed it behind the men as they left.

“I have particular tastes,” she said. “I only enjoy certain things.”

“You don’t like to be watched?” I said, guessing that was why she closed the door.

“No.”

“And you prefer women?” That much I had guessed earlier by the way she had been looking at me.

“Yes.”

“What do you like in particular?”

“I like to be taken by a woman. To be fucked hard.” She reached down and picked up the large dildo that had been in the bag. “With something like this. Can you do that for me?”

“Undress,” I ordered.

I lay on the bed as this prim, proper looking woman deliberately shed her business attire. It wasn’t a striptease exactly, but it was exciting. At that moment I finally understood why men like to watch women undress. I had always thought it a necessary, but not particularly exciting, preliminary step to sex, but the way that Helene slowly unbuttoned each button and slipped out of each garment, got my juices flowing again. She carefully folded each garment after she took it off, leaving them in an organized pile on one of the chairs. The non-eroticism of every deliberate motion she made was incredibly erotic.

She was a small woman, about 5′ 3″ and slender, but not skinny. She had curvy hips, and when she took off her bra, I saw that she had firm, round breasts, perfectly proportioned for her frame, topped with small, brown nipples, the color of her hair.

When she was completely naked, the last thing to come off were her glasses, which she carefully placed on top of the pile of clothes, she undid the bun in her hair, shaking her head, to let her hair fall free. It fell to below her shoulders, completing the transformation from schoolmarm into sex goddess

I stood up. I picked up the dildo and the strap-on harness.

“Put it on me,” I ordered. I really didn’t know how to put it on, and while I would have figured it out, it wouldn’t have been without a lot of fumbling. I figured this would kill two birds with one stone with me being dominant and having her put the strap-on on me.

Helene took the toy and the harness and slipped the dildo through the ring in front and then fastened some snaps that held it firmly in place. She then knelt before me, allowing me to step into the harness, then she lifted it up to my waist and tightened the straps, taking care that the harness was positioned just so. I realized at that moment that there was a small nub on the inside of the harness that was now resting against my clit. When I thrust in and out, it would give me pleasure as well.

Silently, Helene stood up and moved around my back. She embraced me, placing her hands on my breasts and started kissing my shoulders and the back of my neck. God! That felt good. Her hands roamed across my body as she continued kiss the back of my neck, then she moved down, kissing along the spine down to my ass.

Then I got the surprise of the evening. She spread my cheeks and started tonguing my asshole. I squealed, partly out of surprise and partly out of pleasure. It felt great. I’d never played with my ass before. I had thought it was dirty and vaguely disgusting, but here was this woman sticking her tongue up there, licking around the anus and thrusting in and out. I spread my legs to give her more access.

I think I might have cum from that alone if she had kept doing it, but Helene moved around to my front and started sucking my new cock. Of course, I couldn’t feel anything, but it was sexy to look at.

“Is it lubed enough for you?” I asked.

Helene nodded without stopping her sucking.

“Okay, then on the bed.”

Helene gave me a questioning look.

“On your back,” I said, figuring out what she wanted to know.

She complied.

I moved to her, cupping her right breast with my left hand and placing my right over her pussy. She shivered, but wasn’t all that wet yet. I licked my fingers to get them wet and then ran them along her labia, which slowly blossomed open at my touch. I alternated rubbing circles around her clit with the rubbing along her lips until she was wet. Then I slipped a gloved finger in to make sure. I leaned down suckling her breast while I finger-fucked her. I was rewarded with some low moans from this gorgeous woman. I was getting the hang of this girl-girl thing.

I moved my mouth up to her ear, nipping at her earlobe and whispering, “now I’m going to fuck your brains out. Are you ready for that?”

In response she nodded and the muscles in her pussy clamped down around my finger.

I removed my finger and positioned myself between her legs, pressing the head of my new silicone cock against the entrance of her vagina. I pressed forward and it slipped it. I stopped for a moment, and she moaned. Then I shoved it all the way in. Helene yelped, her eyes opening wide, and an almost maniacal smile coming across her face. She liked it hard.

It took me a few minutes to get the hang of using the strap-on. Going slow was no problem, but doing it roughly took a bit of practice. For the first time I gained an appreciation for the work that guys have to do during sex. But soon I was pounding her hard, so hard that she kept moving across the bed, and I had to keep pulling her back to me to keep the rhythm going.

That was frustrating. So I pulled out and flipped Helene over, rather roughly–she smiled at that. She was lying face down on the bed, her feet on the floor, and I entered her again from behind. No preliminaries, this time, I just shoved. She yelled, but it wasn’t the safe word, so I kept going. Pounding harder and harder until I just couldn’t go any harder.

Helene was biting her lower lip, and I could see her fingers digging into the mattress. Then she let out a scream as her orgasm hit her. I stopped my thrusting, just leaving the dildo in her–I could feel it twitching as her pussy clenched and unclenched, milking it. That little nub felt good against my clit–not enough to get me off, but definitely getting me excited all over again as it kept rubbing me from her shuddering as the last convulsions of her orgasm diminished. Then I slipped out of her.

I bent over her, kissing the back of her neck.

“Have you had enough, Bitch?” I wasn’t sure about using that last word, but she trembled when I said it, so I think she liked it.

“No, mistress.”

“Would you like me to fuck you again?

“Yes please, mistress.”

Then I got an idea. She had given me a rimjob, so she was into anal play.

“Would you like me to fuck you in the ass?”

Helene gasped. “Oh yes, mistress, please.”

I peeled off those long, black gloves, grabbed a bottle of lube and squirted some along the crack of her ass, and then rubbed it, making sure the outside of her anus was slick, and making sure my fingers were well-lubed in the process. Then I slipped the tip of my index finger into her ass. She let out a gasp, and I could feel her sphincter tighten around my fingertip. I let it sit for a minute until her anus loosened its grip a bit, and then I pushed it deeper. To the second knuckle, and then all the way. I started working my finger in and out.

“This is just a taste,” I whispered in Helene’s ear. “Just you wait ’til I start pounding your ass with this big dick of mine. Can you wait?”

“No, mistress.”

“Do you want another finger to help you get ready?”

She nodded.

I slipped my middle finger in too, and soon I was reaming her ass hard with both. It was time.

I pulled my fingers out of Helene’s ass and poured lube onto the strap-on. It was already pretty wet from the fucking before, but I figured better safe than sorry. Despite my tough talk, I didn’t really want to hurt her. I’d never done anything like this before, and for a moment I didn’t really know the best way to take her. Then I got another idea.

I grabbed Helene by the hair, and pulled her head back. I kissed her roughly and said, “You’ve been a good little bitch, so I’m going to give you a choice. I’m going to fuck you hard in the ass–no choice in that–but you can choose how you want to take it. Get in the position that’ll hurt you the least.”

“Thank you, mistress.”

And with that she climbed up on the bed, on her knees, ass high in the air, and her head down on the pillows. Before I climbed onto the bed, I had an inspiration and picked up the pocket rocket vibrator, palming it. Then I climbed up behind her and positioned the head of the dildo at her sphincter.

I pushed, slowly but steadily. At first it wouldn’t go in, and I could feel the base of the dildo pressing against my pussy. Then the head popped in. Helene let out a little yell, and I stopped, like I had with my finger, and let her anus get used to the girth of this rather large strap-on. After a minute, I pushed some more. Another inch, and then I stopped again. Then another inch and another stop. Finally I started pushing steadily, still slowly, but without stopping. Helene moaned

Soon, I was buried in her ass all the way to the hilt. I had trouble believing that this little woman could take that big dildo all the way, but she had. I started thrusting in and out slowly. I gradually built up speed until I was fucking her hard, not as hard as I had fucked her pussy, but still pretty hard.

“Can you take more, bitch?”

Helene grunted in response, which I took to be a yes. I started thrusting faster. That little bud felt even better on my pussy. Her ass gripped the dildo tighter than her pussy had, giving it more friction against my clit. I went even faster. Helene’s hand wandered to her pussy, and she started rubbing her clit.

I could tell she was at the verge of orgasm, so I suddenly pushed her hand out of the way and applied the pocket rocket to her clit. I’ve never heard a woman yell so loud, and she went over the falls. She bucked so hard that she pushed the strap-on out of her ass, and it was all I could do to keep the vibrator against her clit. She convulsed. I mean she really went into convulsions. For a moment I was scared that I’d really done something to her. Then her hands pushed the pocket vibrator away from her, she could take no more pleasure. She lay there heaving, tears streaming down her cheeks.

I leaned over and kissed her.

“Are you all right, Helene?”

She smiled and nodded, not yet capable of speech. But she didn’t lay there long.

“You haven’t cum,” she said to me.

“Earlier I did, but not with you.”

She unbuckled the strap-on and dove down onto my pussy, sucking my clit into my mouth. That little bud had gotten me worked up, and it didn’t take long for Helene’s tongue to finish the job. My orgasm was nowhere near as dramatic as Helene’s had been, but it was very satisfying.

We lay together for what must have been nearly an hour, kissing, caressing, and holding one another. It was delicious.

Helene was the one who got up first. She kissed me again, stroked my face gently, and told me that she really enjoyed herself, as if I couldn’t tell from her last orgasm. She asked when I might be coming again, and I told her I was in town for the weekend and would be back tomorrow. She sighed, saying that she wasn’t working tomorrow, and while the club’s owners didn’t mind employees occasionally staying late to indulge themselves, they weren’t supposed to come there when they weren’t working.

After Helene left, I gathered my things, placed them in the bag, and went downstairs to my dressing room. I took a shower and debated whether I should sleep there for a few hours before I put on my street clothes, but I figured I would probably be more comfortable at the hotel. I left the bag and the toys in the dressing room and went out into the lobby. The staff at the front desk, a rather large and burly man at this early hour in the morning, called me a cab, and I went back to the hotel.

I woke a little before noon and ordered breakfast from room service. Then I contemplated what had just happened to me. It was incredible. I thought I had always been rather open sexually, and I knew that I hadn’t done anything all that extreme. Lots of people have had same-sex experiences, multiple partners at once, and played light dom-sub games, but there’s a huge difference between knowing other people do these things and actually doing them yourself. And of course few people have so many first-time experiences in one night. I had jumped into the deep-end and discovered that I was a good swimmer.

What really threw me was what I had discovered about myself. I had no idea that I was something of a dom. Thinking about it, I probably shouldn’t have been surprised. I always had sex on my own terms, picking up guys and calling friends for booty calls when I wanted it. But I had never tried to dominate anyone. But being in charge, really in charge, definitely turned me on. And while I had done a little fooling around with girlfriends and had told myself that I was up for more, I had never seriously considered having sex with another woman. Now I had done it. Not only that, I had liked it. A lot. I thought about that for a while–seriously. At that moment I was really questioning my sexuality at this point. But after a few minutes I realized that while I would happily have sex with women in the future, maybe even going so far as to pick up a woman who looked nice, I really was primarily attracted to men.

Then I thought about going back to the club that evening. There wasn’t any question. I definitely was.

Then I remembered the bag and the mysterious person who had sent it. I hadn’t thought about that since sometime when Helene was giving me the tour of the club. Who the hell had sent it?

Having seen the club, I could rule out any of my friends. This club had to be mega-expensive, and none of them could afford to join it, much less give me a membership as a prank. The same went for most of the people at work. While we’re all well paid, we’re not that well paid. There was Cynthia, of course, but she would never do something like this. Even if she was into kinky sex, she’d never take the risk with someone from work.

I thought about John and Keith, the two clients here in Montreal. John was even a less likely candidate than Cynthia. Keith, however, was quickly becoming the prime suspect. Then I remembered that yesterday John excused himself from our meeting at one point to take care of something because Keith was on vacation in the Caribbean. If Keith did this, he’d certainly be in town to see the result. So I still had no clue who sent the bag.

I put the thought of who had sent the bag out of my head. It did not good to dwell on the matter. The person would eventually reveal themselves, and then I would deal with it.

I went out for a few hours to play tourist and check out the city. Montreal is a great city, and I would enjoy coming here, even without considering the Club Sans Limites. But I cut the tour short in the late afternoon and headed back to the hotel for a nap and then a light, room service dinner. I wanted to be ready for action that evening.

Around eight I called the club and said I would be coming by at ten, and to please have my things ready for me. The man who answered the phone was very pleasant and said it would all be ready when I arrived. Then I spent the next two hours in nervous expectation. Finally it was time and went downstairs and caught a cab to the club.

Going into the club seemed different this time. Of course the it looked the same. The staff at the front desk, a handsome young man who I would have been glad to pick up in a bar a week ago and a nice-looking young woman who I’d now gladly pick up after last night, were friendly–although not as friendly as Helene had been, but then she was a special case. But I was more confident. I knew what to expect, or at least I had a reasonably good idea what to expect. I knew that I was still in for some surprises.

When I got to my dressing room, the bag and all its contents had been cleaned and were laid out for me. I thought about just going naked, but decided I should have some kind of sexy accoutrements. I decided to forgo the body harness and gloves, but I put on the leather collar and boots, and again I tied my hair back in a ponytail. That had worked well last night. Then I picked up my strap-on and my bottle of lube, leaving the vibrators and other toys behind as too much to carry, and walked out into the club.

It was more crowded tonight. There were four couples scattered about the floor of the main room, engaged in various activities. And there was one threesome in the middle, where a woman was tied down over the horse. One man was spanking her, and another was teasing her mouth with his cock. That looked promising, but I decided to make a round before committing to anything.

I walked upstairs. Only three rooms were occupied with open doors. An older couple was fucking in one. Another, the room I had been in last night, had two women toying with a man who was tied spread-eagled to the bed. That looked like fun, but I really wanted some cock tonight, and three women in one room would be a bit much. The third had a well-muscled guy sucking another guy’s cock. I stayed and watched that for a while, but no invitation to join them was forthcoming, so I moved on, a little disappointed but appreciative of the eye candy they had given me.

I looked over the balcony at the people downstairs. The couples all seemed pretty engrossed in one another. So the threesome in the middle looked like the best bet for my first fun of the evening. I went down and approached them.

I stood a few feet away, strap-on and harness in hand, waiting to see if they wanted more company. I looked at the man who had been spanking the woman, and who was now giving her a rimjob and realized that he was the most drop-dead gorgeous man I had ever seen. In his late-thirties with brown hair that was just starting to go gray around the temples, strong jaw, and chiseled features. His body was toned, without being aggressively muscled, tapering from broad shoulders to a slim waist and a cute butt. And, best of all, from the bulge in his leather g-string, which was the only thing he was wearing, he was very well-built down there too.

The woman looked attractive, although she was facing away from me, and since she was bound and lying face down over the horse I couldn’t see her well. She looked a bit older, fortyish maybe, with short, dark brown hair. She was wearing a leather bustier, garter, fishnet stockings and high heels.

The other man was quite good-looking too, but suffered in comparison. A bit younger, he was also blond and thinner, attractive, but not as aggressively masculine and oozing testosterone as his male companion. He had stopped teasing the woman with his cock, and now she was sucking it. He looked at me, smiled, and waved me over.

“I’m Alan. I have two playmates here,” he said. “If you’d like to play with George for a while go ahead, while I get Cynthia ready. She likes a triple stuffing.”

I looked down at the woman and suddenly realized she was my Cynthia. My boss.

Cynthia stopped sucking just long enough to smile and say, “Hello, Jenny. I’m glad to see you enjoying your membership.” Then she went back to sucking Alan’s cock.

I guess I knew all along that it had to have been Cynthia who gave me the membership, but knowing something in your bones and suddenly being faced with the fact are two different experiences. I couldn’t respond. Nor could I process what this all meant.

I just stared. It was Cynthia all right, but I’d never imagined her like this. I just watched, stunned, as she sucked Alan’s cock and George rimmed her ass. She looked good, really good. It seemed like I stared for ten minutes, but in actuality it probably wasn’t much more than thirty seconds.

I knew I couldn’t stand there gawking all night, so I walked over to George, took him by the hair, made him stand up, and walked him over to where Cynthia could see us. Then I made him kneel and shoved his face into my pussy. George’s lips and tongue went right to work, first grabbing and gently tugging at my labia, then his tongue sliding up between my nether lips, and finally after a few minutes of this, after I was thoroughly wet, he locked onto and started sucking my clit. He was a good pussy licker; not as good as Celine had been last night, but still very good. All the while Cynthia kept sucking Alan’s cock, but her eyes were locked on mine.

I was so intent on watching Cynthia, I almost missed the warning signs of my impending orgasm. But I noticed the tingling in my legs at the last moment and grabbed George’s shoulders for support as my first orgasm of the night swept up through me. It was a nice one, but not overwhelming, but I was just getting warmed up.

But I still needed some cock. I pushed George’s head away and knelt down facing him. I kissed him and said, “that was quite pleasant, George. I’d like to give you a reward for eating me so well. Would you like me to suck your cock?”

“Yes, if it pleases you mistress.”

“It does. You have a very nice looking cock, and I want to know what it tastes like. Stand up.”

George stood up, and pulled his g-string down, taking my first close-up look at his penis. It was beautiful, some seven inches long, and nicely thick. It was mostly erect already, with the head poking out of the foreskin. I took it in my right hand, rubbing down the length of the shaft and exposing the head completely. I knew it would feel fantastic inside of me.

I took a quick lick at the head, running my tongue along the hole, catching a drop of salty pre-cum. Then I dove down, taking most of his shaft into my mouth, and started sucking in earnest. I really like sucking cock, and this was one of the nicest I had ever been presented with. After a bit I switched up, pushing his penis up against his stomach, and tacking the underside of the shaft, occasionally dipping down to take his balls in my mouth.

All the while I kept glancing over to Cynthia. She was still watching, but Alan had moved around and was fucking her from behind. I only wished I weren’t so busy. I would have liked to watch them. But there would be plenty of time for that.

Finally, I couldn’t take it anymore. I had to find out if George fucked as well as the looked and tasted. I stopped sucking and laid back onto the floor, pulling George down on top of me.

“Fuck me,” I commanded.

“Yes, Mistress.”

I could feel him rub the head of his cock against my labia, finding the entrance to my vagina, then he pushed forward and entered me. It felt wonderful as he filled me. He started thrusting back and forth, and I wrapped my legs around his torso, matching his thrusts. We fell into a rhythm almost immediately, as if we’d been lovers for years.

I looked over at Cynthia and Alan. He had unstrapped her from the horse and had laid her on the floor next to me. He was now fucking her missionary style too. I reached over and grabbed Cynthia’s hand. She gripped mine back tightly.

It didn’t take long for George to bring me off a second time. This orgasm was bigger. I don’t think I screamed–it was probably more like load moaning. Five or six major contractions and then a lot of little ones as George stopped his thrusting, holding his penis inside me. My vaginal muscles kept tightening and loosening around his shaft. God, it felt good. Then, slowly, he started thrusting again.

Then I had an idea. I don’t know what made me think of it. Maybe it was because I was still holding the strap-on in my left hand. I’d never given any thought before to pegging a guy before, but suddenly I wanted to take this gorgeous man who was standing in front of me.

“George.”

“Yes, mistress.”

“Do you like to be fucked in the ass?”

“Yes, mistress. Very much.”

I slipped off of him, letting go of Cynthia’s hand, somewhat reluctantly, and stood up. I attached the strap-on and told George to assume the position. He got down on his elbow and knees, ass high in the air.

I applied a generous amount of lube to the dildo, and then to the crack of his ass, working one of my well-lubed fingers into his asshole in the process. It was tight, gripping my finger so hard it almost hurt.

“Relax, I’ll go slow at first,” I told George. Then I worked a second finger in, and started moving them back and forth slowly. George exhaled, and his grip on my fingers loosened a bit. I moved my hand a bit faster, keeping it up until could withdraw and insert my fingers quite easily. It was time.

I positioned the head of my dildo at his anus and gently pushed forward. There was a moment of resistance, then the head of the dildo popped in. George gasped, then relaxed. I held it there a moment, and then started pushing slowly deeper. One inch. Two inches. Then three. Soon I was buried to the hilt.

I started thrusting in and out, slowly at first, but picking up speed as I went. Soon I was slamming George pretty hard, but he didn’t seem to mind, letting out a low groan of pleasure each time I drove the dildo back deep into him. I reached around and grabbed his cock, giving him a handjob. It was rather tricky at first to get the rhythm of both hand and dildo working in sync, but I got it after a minute.

It didn’t take George long. He’d been building up to this all night, and my stroking his cock sent him over the edge. He erupted all over my hand. I kept stroking, but slowed my thrusts, eventually pulling out of him. I shoved my hand in his face, telling him to lick his cum off it, and he dutifully complied. I can’t describe the thrill of having this beautiful man do whatever I said.

I looked over at Cynthia and Alan. I’d forgotten about them as I had gotten busy with George. They had finished fucking and were watching us.

“Now, are you ready to be triply fucked?” Alan asked Cynthia.

“Yes, Master. If you desire it.”

“Now go prepare your fellow slave so he is ready for you. The faster you get him hard, the faster you’ll be fucked.”

Cynthia crawled over and took George’s cock in her mouth and began sucking. I moved over and sat next to Alan, watching the pair. I noticed he was still hard. He evidently hadn’t cum, and he was slowly stroking himself to keep himself that way. I reached over and took over that duty as we watched. It was the least I could do for his sharing George with me.

“It won’t be long,” says Alan. “George has a rather short refractory period. He’s ready to get back in the saddle in minutes. He’s really an amazing fellow.”

“Are you lovers?” I asked.

“No. I mean we have played together on occasion, but neither of us is really into other men. Usually we team up with another sub woman. We play with Cynthia whenever she’s in town, but we’ve been looking for a dom woman to join us regularly. She told us you were coming to town this weekend and might be joining the club, so she arranged for us to meet.”

All the while we were talking I was getting my first good look at Cynthia. The business attire I was used to seeing her in showed that she had a nice figure, but it obviously covered up a lot. She is quite petite, about 5′ 3″ and small framed, but she sported a very nice pair of breasts that her business suits hid quite well. They were still firm and capped with big pink nipples. She also shaved down there, completely. I wax and keep my hair down there trimmed short, but I’d never thought of Cynthia doing it, much less taking it all off. She really is a beautiful woman.

Alan and I continued chatting as I slowly stroked him to keep him hard, but he was right. George was ready to go again in less than ten minutes.

Alan orchestrated this next phase of our session. He handed me another strap-on that was identical to mine; it must have been Cynthia’s. I exchanged it for the one that I had fucked George with, and once I had it cinched up, Alan had me lie on the floor. He then grabbed Cynthia by the hair and led her over to me.

“Fuck your friend for me,” he commanded her. And Cynthia lowered herself onto my silicone cock. I was face to face with my boss for the first time that evening.

Then Alan snapped his fingers, signaling to George. He pointed, and George obediently moved behind Cynthia. A moment later she gasped. I couldn’t see it, but he must have penetrated her anus with that rather large cock of his.

Then Alan placed a foot on either side of my head and fed his cock to Cynthia’s waiting mouth. This was the triple-stuffing that he had been talking about.

Cynthia began to rock back and forth on my faux-cock as George thrust into her, and with each forward thrust she engulfed Alan’s cock with her mouth.

I tried to match her movements by thrusting my hips in time, but Cynthia’s hips and thighs kept me pinned to the floor; she was using me as a base to steady herself. So there wasn’t much I could do but watch, but it was quite a view. As I said, I couldn’t really see George, but Cynthia’s body and movements were on full display for me. Her nipples were hard as rocks, pointy as pencil erasers. Looking straight up I could see her blowjob technique from below. It was an angle I’d never seen before, watching Alan’s balls swing back and forth every time Cynthia thrust against him.

I couldn’t get any sensations from Cynthia’s vagina against the dildo, of course, but I could feel that little nub move back and forth against my clit as she moved and with each of George’s thrusts. It felt good and was getting me worked up, but it wasn’t enough to get me off.

Alan, unsurprisingly as he’d been building up to it all night, was the first to cum. As he groaned, George stopped his thrusting for a moment, allowing Cynthia a chance to milk Alan’s cock of the last drops of semen, then Alan withdrew his rapidly deflating penis.

Cynthia looked down at me.

“You had better have saved me some of that cum,” I told her sternly. She nodded yes in response, unable to speak with her mouth full.

I reached up and pulled her head down to mine, and we kissed for the first time, transferring the salty goo into my mouth, and then back into hers. We kept kissing, smearing the cum over our faces.

“You’d better clean that off me,” I said.

“Yes, mistress.” And Cynthia began dutifully licking the cum off my face as George resumed his thrusting.

I tried kissing Cynthia again, but it was difficult. George was thrusting too hard. So I just held her head in my hands as she ground against my strap-on dildo and took each of George’s thrusts. I could tell from her expression that she was about to cum, and a moment later she began moaning and panting.

“Oh, God, God, uh, uh, uh, God.”

She quivered and shook. It was like an earthquake happening on top of me. I heard George groaning too. He was cumming as well.

When George withdrew, Cynthia simply collapsed on top of me. I held her tight until she stopped trembling. Then I brushed her hair back and started kissing her. She didn’t respond at first, but after a few kisses she started returning them, and we spent the next few minutes just holding each other and kissing.

I realized that we were neglecting Alan and George, so I broke the kiss and looked around for them. They were sitting on a nearby couch, watching us and smiling. Two other women were with them, watching as well. I looked around and realized a small crowd had gathered to watch, but was breaking up and the people were getting back to whatever activities they had been engaged in before. I gathered that the four of us had put on quite a show.

I motioned to Cynthia, and the two of us crawled the short distance to where the two men were sitting. I thanked them and we kissed. But they seemed comfortable with the two women who had joined them and looking for some new adventure, so I promised to ask the club to tell them the next time I was in town.

I took Cynthia by the hand and led her away, picking up the other strap-on as I left. I wanted some time alone with Cynthia. I didn’t know if she wanted more sex that night, but I needed to talk to her. We went upstairs to an empty room, and I closed the door behind us.

“What would you like me to do, Mistress?” asked Cynthia as I unstrapped the dildo that was still around my pelvis.

I told her that the role play was over for now, and that I wanted her to join me on the bed. We lay down and just looked into each other’s eyes for a few moments. Finally I spoke.

“I can’t believe you bought me the membership to this club. How did you know I would take to it.”

“Well, I don’t know what I find harder to believe, that I actually screwed up the courage to do it, or that you followed through and came here. But I had my suspicions that you might be a bit kinky.”

“Well, I had no idea. Before this the kinkiest thing I’d done was a little mutual masturbation with a girlfriend. I’ve been pretty vanilla. I was happy with my sex life, but after these two nights, I see there’s a whole nother world of things for me to try. But the last thing I expected was for you to be into it, especially as a sub. You’re so commanding and charging at work.”

“I guess the sub thing is a release,” she said. “You can’t be in charge everywhere. It’s too exhausting. To let go and have other people tell me what to do is relaxing for me. And I’m so exciting that you’re a dom. We’d have fun together regardless, but that’s just perfect.”

“Do you do this at home too?”

“Not so much. I try to keep my play a few hundred miles away from home so no one finds out. But there are few discreet couples I play with sometimes. I’ll introduce you. And now, of course, I’ve got another friend to play with at home. That is, if you want to, of course. Our professional relationship won’t change one bit regardless, and we’ll still be friends even if you don’t want to play.”

“Oh, I definitely want to. I want to explore my bi side more, although I’m pretty sure that I’m mostly into guys.”

“Me too. I’ve got a strong bi streak and really enjoy women,” she said. “But I couldn’t live without a good stiff cock.”

It was weird to hear her talk like this. But I could get used to it.

She told me that she had gotten me a three-year membership to the Montreal club. Club membership fees were usually non-refundable, but she’d worked a deal with the club to get a refund for most of it if I had refused it. She also admitted to arranging for Helene to take special care of me on my first night.

“What have you discovered about yourself?” she asked.

“Oh, God. Like I said, I’ve discovered that I’m a bit bisexual, but there’s just something about muscles and a hard cock that I can’t do without. I think I kind of knew I wanted to play around with women, though, at least in some recess in the back of my brain. But the dom thing came out of nowhere. I had no idea that was lurking underneath my skin. I really get off on telling people what to do.” She smiled again.

I leaned in and kissed her again. Cynthia was irresistible when she smiled.

“Are you up for a little, gentle, vanilla love making?” I asked. “Vanilla is one thing I haven’t tried here yet. Is it allowed here?”

“Well, I won’t tell anyone if you don’t”

She kissed me again, and I rolled onto my back pulling her on top of me. She then slipped down and took my left breast into her mouth. I just leaned back and let her take me, too tired to keep playing the dom. After a few minutes of playing with my left nipple, getting it nice and hard, she switched and did the same to the right. I love to have my nipples played with, they’re so sensitive. But all too soon she journeyed south, stopping to tongue my navel for a few moments, then on to my pussy.

She gave me several minutes of delicious frustration as she kissed the inside of my thighs and mons, and as she sucked my labia into her mouth, doing everything except touch my clit. When she finally clamped her lips around my bud it was a blessed relief.

After a few minutes of just lying back and enjoying, I asked her to swing around on top of me again, and we settled into a sixty-nine.

Cynthia’s pussy was sweet and it didn’t take long for both of us to rock into another orgasm. I was the first to go over the falls, and when I recovered and returned to my duties Cynthia followed soon afterwards.

We held each other for a while, and then headed downstairs to the showers and back to the hotel. Cynthia was staying in another hotel, but she spent the night with me in mine. It was the first of many nights that we would be together.