Pleasure Penthouse: Hour 00

Prologue

A woman receives an interesting offer on a sexchat site.

I logged onto the chat site, already a little aroused. In just a matter of a few months, the site had really changed my life - for the better. I had no idea that things were going to get even more exciting in a short time.

As usual I clicked into the lesbian chatroom first, wanting to say hello to my favorite girls and see if there was anyone interested in private messaging. There were a few messages already waiting in my inbox, evident by the little red number in the corner. I opened them and read through them. Some were friends saying hello, others were just dick pics. And then there was the message that changed everything. It was sent by someone I didn't recognize - not one of my friends - and appeared to be a guy from the username.

"Hello there. I'm reaching out to you about an unique opportunity I think you would be interested in. You chatted with a friend of mine, who relayed how enthusiastic you are in your sexual experiences. Your bio further added to my desire to invite you to an exclusive event taking place in the pleasure penthouse. Please let me know if you are interested in further details."

I was curious I'll admit. There were any number of people, men and women, who could have relayed this opinion about me. I was always engaged when I chatted and engaged in cyber sex. Even more so when I would video or voice call. I contemplated the message for a few seconds, fingers tapping against my laptop.

"You got me curious. Sure I'd like more details." I quickly tapped out and sent to this strange messenger.

The response came within minutes.

"I understand you have no qualms about video calling, as long as you have established a relationship of trust. Would you be interested in a face to face session? The highest assurances would be provided that you can still remain anonymous, and you would also be compensated monetarily for expenses and for enjoyment."

As I read the message I realized that this man still hadn't told me the exact sexual aspect yet. And it sounded like I would be paid?

"I think I need more info before agreeing to a f2f. What is the sex part of this? And what exactly are you offering to pay me for? I'm not a call girl fyi."

Now the response came in seconds.

"You would be invited to a party at the pleasure penthouse, one that would last 24 hours and have multiple people engaging in various sexual activities. You would be paid $1000 for every orgasm you have during this 24 hour period, either at your own hand or others. Our mutual friend XXXXXXX can vouch for the authenticity of who I am and this event. The event is taking place in San Francisco in a week's time. Are you interested?"

My pussy came to life as I read the message. It sounded like a challenge. A really fun challenge that could be win-win, and a trip to SF could be fun. I rocked in my seat for a couple seconds, then leaned forward to send my response.

"Hell yes"

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This was the beginning of my experiences with pleasure penthouse, all of which have been remarkable. I can't even count the orgasms I've had at all the various events I've attended, and I've had a few relationships (sexual and emotional) come out of my visits to the penthouse. I have most definitely done things I would never have done before, or even wasn't comfortable with in the moment. Didn't stop me from cumming though. I guess I'm just saying that this journey wasn't as clear cut as I thought it was going to be when I said yes. And this mystery man turned out to play a huge role in corrupting me with pleasure, pain, and even love.

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Hour Zero

She enters the penthouse.

As the car slowed, chugging over the rails, a garbled announcement came over the speakers notifying the passengers of the station they had just pulled into. I grabbed my tote from where it was sitting at my feet and stood, stumbling slightly in my heels as we abruptly stopped moving. I caught myself on a pole and looked up to see a man sitting across from me staring at my bare legs. He was hot and I definitely didn't mind, so I blew him a saucy kiss. I saw his lips quirk up in the shadow of a smile as I slung my bag onto my shoulder, pulled my coat tighter around me, and turned to follow the other passengers getting off. My heels clicked and echoed quietly in the underground Bart station, relatively empty at the moment. All the commuters had already made their way to their respective homes, and now only San Francisco natives and tourists were left in the station at 9pm on a Friday night. Well them and college kids out going bar hopping with their fake IDs.

I chuckled as I watched a particularly affectionate young couple groping each other as they made their way up to street level. Ah those had been the days...But this was supposed to be quite the promising night as well, and with that thought in mind I turned to survey my surroundings, looking for whoever was supposed to guide me to my next stop.

Here I was in San Francisco, a week after the mystery man had first messaged me. I feel a bit silly calling him mystery man, but that's what his username had been and he made no effort to introduce himself when explaining the details later. I had been booked on a flight which landed at 7pm at SFO, been told that I needed to bring nothing other than a form of identification and my phone if I so desired. Then from the hotel I would take Bart and get off at a station where someone would meet me and walk me to the hotel the penthouse was located at. Mystery man was living up to his title.

I grinned as I remembered how I had tartly typed out the question of whether I should be wearing any clothes or not, or should I truly bring nothing. Of course punctuated with emojis. I loved to tease and mystery man had really just made it too easy. His response had been fun.

"You may dress comfortably for your flight. At arrivals someone will be waiting to drive you to your hotel where you can leave any personal items you bring with you. Clothes and beauty items suiting the event will be provided for you to wear and keep. If you have anything you would like to wear specifically, feel free to voice that request now."

So proper and polite, always straight to the point. I could just imagine our mystery man sitting in an office somewhere, typing away intently, lining all the details to a sex event nicely while wholly ignoring my blatantly sexual flirting. A man like that, you just knew he always had to be in control. And a girl like me, well you just know I love making people lose control. Which was probably why I had..ahem..used the method I did to describe what clothing items I wanted to request.

Shaking my head, I smiled again and ran my hands down the length of my trench coat, smoothing it over my bare legs. I wasn't naked underneath, no. In fact my attire was probably more indecent than just a plain old birthday suit. I was wearing a surprisingly sturdy fishnet bodysuit, that was cut high to showcase my slim stomach and thighs but still tight enough to provide support to my breasts which swayed with each step of my four-inch glossy black stilettos. And of course accessories! Silver nipple clamps connected with a delicate chain with a section of chain running down to attach to my belly piercing to form a Y. Steel armbands tightly encasing my biceps, and a floofy black garter on my left leg. My lips were a deep red, my lashes coated in water resistant mascara, and my eyelids a smokey brown. I looked hot, no scratch that - I looked utterly fuckable.

In requesting the clothing I had a lot of fun...

I had dressed up in a get up very similar, down to the last detail, and posed for the camera in a variety of ways. Pressed up against a wall with my arms stretched above me. On all fours with my ass facing the camera, quarter sized holes in the netting perfectly showcasing my holes, and looking over my shoulder while I bit my lip. Legs spread over either arm of a chair and my hands in my hair, eyes closed and my head thrown back. On my knees but sitting back on my bum, sucking two fingers into my mouth as I looked directly into the camera. Oooh I had fun with my little photoshoot and I had certainly taken my time, to the point that mystery man had messaged me asking if I was still there. Little did he know...

I told him, "Sorry, stepped away for a second. Wanted to get pictures of what I want to request, and it's pretty specific. Hope that's okay?"

Within seconds he responded with a "Yes that is fine. Send the pictures here, and I will do my best to get all the items." Hook, line, and sinker! I then grinned shakily as I uploaded my pictures to my laptop, and started sending pose after pose to him. Each picture steamier than the last, but I gave him no time to respond in between them. And hell yea I was turned on. Fun clothes and a camera always did that to me.

But the minutes stretched out and mystery man didn't respond, and I started to doubt myself. Had I gone too far? And then finally he messaged back.

"I appreciate you going above and beyond for your request. All items will be waiting for you in your room. But I am going to have to ask you to send in your measurements for the following:"

And then he sent a detailed list of everything from bust size to bicep width and the length from my waist to crotch. Well not necessarily the response I was expecting...maybe he was gay? Or asexual? Well that didn't make much sense for a guy running a pleasure penthouse. The asexual part I mean. Guess he just wasn't into me.

Glum, I got up to dig out my measuring tape from my laundry room. When I returned to my room, to my surprise there was a message notification waiting for me. Was he already getting impatient?

I clicked open our chat and read, "Feel free to continue being creative with your measurements." Smiling, I quickly shed my thin attire, unwound the measuring tape, and positioned myself in front of the camera again. Maybe he wasn't completely immune to me after all.

Before I could take the first measurement, my computer pinged that someone had PMed me. I turned to see a new message in the chat box I still had open.

"Don't take so long this time."

Unable to resist, I typed out, "If you're so impatient why don't you come and measure me yourself?"

His response was instantaneous. "I can think of other uses for a ruler when I see you next week." My body hummed. He was going to be at the event? And other uses for a ruler...my arousal came rushing back, leaving me tingling and a little breathless. All of a sudden I was even more eager for Friday to roll around.

The sound of the next Bart train screeching into the station pulled me out of my memories. A quick glance at the scrolling text on the platform screens showed that it was the 9:13 train. The event was supposed to start at 10pm, and I still had no idea which hotel I was supposed to go to. I had been waiting here for ten minutes, and the schmuck that was supposed to be my guide was starting to look like a no-show.

I crossed my arms and tapped one foot, thinking about my situation. I knew the way back to my hotel, and the key card was in the pocket of my trench coat. I could get back on another train going in the opposite direction. No, that's not what I wanted though. I dropped my arms in frustration and looked around as a few individuals trickled out of the still train behind me. Maybe he was late?

Or...maybe he was already here, and didn't know what I looked like. I slowly looked around the station. There were some people at the ticket machine, others in front of the map of the Bart system. A few moving slowly in and out of the exits and stairwells to the street above. And some waiting for the next train to come in. But no one waiting for a someone.

Or so I thought. I honestly missed him in my first and second pass of the people around me. It was only the flickering of the shadows from the departing train that caught my attention. There, at the end of the platform next to one of the brick columns was a man standing with a briefcase in hand. Not a strange thing on its own, considering that others were also standing still, presumably waiting for the next train. But unlike the others, this man wasn't leaning against the column tired after a long day. He wasn't staring at his phone or the dark tunnel in anticipation of the next train. His body was half turned towards the platform but his face was angled toward me. At this distance and with the lack of light, I couldn't make out his exact expression but I knew he was looking at me.

The second I realized that this man was the schmuck I was waiting for was the second he started moving toward me. He was wearing a well cut suit that framed his body, and his long legs were steadily decreasing the distance between us. But he wasn't in a hurry. So I made no move to go towards him. As he got closer to me I realized that he was the guy from earlier, the one who had been looking at my legs and the one I blew a kiss to. The same shadow of some sort of expression was on his face — not quite amusement, not wholly serious, but something in between and far more intense. I continued checking him out as he grew to a close and stopped next to me. With a briefcase in one hand and an expensive watch on the other, he looked every bit of the business man he probably was. Tall, dark, handsome, and used to being in charge. And suddenly I knew who he was.

My lips curved up into a bright smile as the silence stretched out between us. My grin seemed to irritate him because he frowned, a quick wrinkling of his forehead and downturn of his lips.

"Something funny?" He questioned, voice quiet and steady.

"Just saying hello," I said with a small flip of my hair. I had my usual desire of wanting to rile up this man who was just so put together, I really couldn't resist.

He cleared his throat, blanking his expression, and held out his hand, "Shall we?" He obviously expected me to take his hand, which goes to show he really hadn't figured out that he should know better by now.

Feigning confusion, I looked down at his hand and then back up to his face. "I'm sorry...but do I know you?" My tone was innocent but I'm sure my eyes gave me away.

A quick flare of exasperation followed by amusement crossed his face as he shook his head and then grabbed my elbow. Without giving me a second to protest, he started moving towards the east stairwell dragging me along with him. "You really do need someone to take a ruler to your backside." There was a hint of gravel in his voice now, enough to send a spark of awareness through me. And of course the reference wasn't lost on me - it was him!

"Hmm, are you volunteering?" I teased as I pulled my elbow away to link arms with him instead. I was rewarded with another quirking of his lips as we stepped out onto the street. He never broke his stride once, but he moved at a pace that allowed for my ridiculously high heels even though I'm sure we could have been walking faster.

The sounds of the San Francisco night filled the air between us as we stopped at a corner waiting for the crosswalk. Even with my heels and already considerable height, he still had a few inches on me. And with his brooding looks and attitude, mystery man was certainly living up to his moniker. Looks like it was up to me to make conversation. Not a problem.

"There a reason you kept me waiting? Or why you didn't talk to me on the train?" I asked, glancing up at him as we continued moving toward a destination only he knew. He looked down at me for a moment and at our linked arms before responding.

"I was debating whether to take you to the penthouse or not." He said the words matter of fact, but surprise and shock passed through me.

"You mean you were reconsidering my invitation? But why? What did I—," I exclaimed before he sharply jerked me closer to him, stopping us on the sidewalk and silencing me.

"I was debating whether to take you to the penthouse or to my room." He rushed the words out, head bent closer to me and his voice gravelly again. And that strange expression from before was back, except this time I could place it. It was desire. My breath hitched a little and I could feel a slickness between my legs, a result of our proximity and the meaning of his words. His eyes held mine for a heated moment, before he pulled away and we were moving again.

I was quiet for a few minutes, catching my breath and trying to get a control of my arousal. After all, I had a pretty important challenge ahead of me. But still I couldn't stop myself from saying the next sentence.

"I thought you were gay." My tone was just as matter of fact as his but there was a small smile on my face. I was rewarded with his steps faltering, but we didn't stop this time. In fact he picked up the pace, his hand sliding down to grip mine and pull me along. He threw a dark look over his shoulder at me.

"No, not gay." He didn't say much but his response spoke volumes. So did his lack of outrage. I grinned wider.

"But I'm definitely getting bi vibes." The tightening of his hand was his answer. "You are bi. So are you a top or a bottom- oof!!"

I cut off as we came to a halt next to a set of glass doors, with me crashing into mystery man's chest. They were nondescript and so was the entire wall behind them. Mystery man punched in a code on the keypad next to the doors and they clicked open. He pulled open a door and gestured me inwards.

"We're here. And Miss Abbas, my sexual preferences are not the point of interest here." He was back to being curt and proper. I stepped inside and he pulled the door closed behind him. With his hand was at the small of my back, he pushed me through a quiet lobby towards an elevator.

When he pushed the call button, the doors immediately slid open. And then we were inside and he was twisting a key into a slot on the button panel. We were moving upwards, the air tingling with anticipation of what was to come. Still I couldn't let him have the last word. I slid closer to him, drawing his dark eyes to my face. I held his gaze as I leaned in to press my lips to the skin just above the first button of his shirt.

"I disagree. I'm definitely interested in your sexual preferences." I pressed closer to his front gasping a little as the nipple clamps pinched, his hand falling just above my ass and his eyes making it clear that he was only letting me get this close. I rubbed my nose against his jaw, my lips inches below his and my hands flat on his chest. "Also I don't think it's fair that you know my name and I don't know yours."

He let out a small chuckle, one that both surprised me while turning me on. "Would you prefer it if I call you Fucktastic Gal?" The elevator doors dinged open behind us and he tightened his arm around me, walking me backwards as he moved to exit the elevator.

We stopped in the middle of the hallway and he looked down at me, waiting for my response. I hummed and darted out my tongue to lick the same spot I had kissed. "Better than Miss Abbas. But Ana will have to do." It was clear I wasn't going to wrangle his name out of him, and honestly I wasn't too focused on that anymore.

But to my dismay he let go of me and stepped away. Shaking out his cuff while still holding his briefcase in one hand, he nodded to something behind me. I turned to see a blue door, no number on its front.

"Once you step inside your 24 hours start. Do you remember the conditions?" He was looking at his watch when I turned back to answer.

"$1000 for each orgasm I have between tonight at 10pm and tomorrow at the same time. I can use anything or anyone in the penthouse. No phones or last names allowed. No taking off masks for any reason. If there is an emergency, find and press a call button present in each room." I rattled off what I had drilled into my memory, and he nodded in satisfaction.