For several years, I've been working at a local hotel. It's not a high-end chain hotel, nor is it a discount hotel. It's a small, city-based, "best-kept secret" type of hotel, the kind that prides itself on it's personal approach to customer service and thrives on maintaining the privacy of it's guests. It does tend to cater to the wealthy, whether they are private citizens or celebrities, who expect and rely on the privacy and services we provide for them.
In the years I've been working at the hotel, I have served in several capacities - housekeeping, lounge waitress, desk clerk, janitor and concierge assistant to name a few - but my favorite role is quite unofficial and off-the-books. For the last few years, I have found myself serving in the capacity of what we call "Pleasure Facilitator." Feel free to read into that whatever you desire.
It began three years ago. I had just graduated college and was not working full-time for the hotel, usually double-shifts where I would work housekeeping in the morning and afternoon, and work the desk in the evenings. One such evening, one of our guests, Mr. Jones, approached me with a very unique request. He told me that he was going to be taking his 18-year old daughter out on the town for dinner and a show, and he was hoping that I could go and "entertain" his wife for the evening while they were away. I was quite surprised by the obvious tone of the request, and asked him for clarification, hoping that I was reading more into the request than was there. He very casually informed me that his wife had found me attractive and that she wanted to spend an intimate evening with me. he indicated that there would be a substantial tip included if his wife found me satisfactory.
As this man shared with me his request, I started to get damp. I had seen his wife around the hotel, and she was easily one of the most beautiful women I had ever seen. She was in her late-40's, but looked no older than her teenage daughter. She had flowing blonde hair that framed her perfect face. Her eyes were pools of deep blue, her soft red lips were inviting. She was petite, and constantly wore 4" heels, which made her magnificent legs all the more statuesque. I did not admit it at the time, but there were several times through out the day that I found myself fantasizing about her, dreaming of her naked body laying on the bed of her room. And now, here I was, being presented the opportunity to make my fantasy a reality.
Mr. Jones cleared his throat, bringing me back from my daydream. He handed me a piece of paper and indicated that I should follow the instructions. He then turned and left. I opened the piece of paper and read the instructions as obviously written my Mrs. Jones. The instructions indicated that I was to arrive at the suite no later than 6:45. I was to remove my clothes in the hallway, save for my heels, and place them in a lock-box that would be sitting outside the suite. Once my clothes were secured, I was to use my passkey to enter the suite. The note indicated that Mrs. Jones would be waiting for me inside the suite and if I failed to enter naked, she would refuse me entry. Once accepted into the suite, I was to refer to Mrs. Jones only as Mistress, and to myself only as Pet. I was to speak only when spoken to, and if, at any time I became uncomfortable with the situation, I was to use the word "Pineapple" and our evening together would end immediately. The note also indicated that my tip would only be provided if I remained until Mr. Jones and their daughter returned, or until Mrs. Jones dismissed me.
To say I was excited would have been an understatement. Fifteen minutes after our conversation, I watched Mr. Jones exit the hotel with his daughter. I glanced at my watch and saw that I had 10 minutes to get to Mrs. Jones room and begin our evening. I quickly mad my way up to the 3rd floor and to their door, which was at the end of the hall. Looking around, praying that none of the other guests would choose that moment to exit their rooms, I quickly removed my skirt, blazer, blouse, bra and panties, folded them and placed them in the lock-box. The click of the lock as I closed the lid echoed in the empty hallway. I took a deep breath, slid my passkey in the lock, and opened the door.
As expected, Mrs. Jones was standing in just inside the suite. She was wearing a pair of white 4" heeled slippers and a sheer white robe that tied just below her magnificent breasts. Her bald pussy was uncovered with a hint of moisture glistening in the light of the foyer of the suite.
"Well, pet, I see you are quite eager this evening. I applaud you for following instructions so well." Mrs. Jones said, almost purring.
"Thank you Mistress." I responded, curtsying politely.
Mrs. Jones chuckled, "Well, aren't you well-mannered? I suspect that means you are also obedient. Are you obedient, pet?" she asked.
"Yes Mistress. I am obedient." I responded, trying to stifle my excitement.
"Very good, pet." Mrs. Jones said, "Masturbate for me, pet."
I looked at Mrs. Jones, and slowly slid two fingers of my right hand into my moist pussy. As I fingered myself, I watched as Mrs. Jones licked her lips, her hands slowly lifting to her perfectly round breasts, her fingers gently tracing around her wonderfully hard nipples. Watching Mrs. Jones tease herself made me finger myself harder and faster, my pussy becoming wetter by the second. The sloshing sound of my fingers sliding in and out of my drenched pussy echoed in the foyer of the room. I felt my orgasm starting to build and wondered if I would be allowed to enjoy it right.
"Are you close, pet?" Mr. Jones asked, as if she were reading my thoughts.
"Yes Mistress" I replied, breathlessly.
"I want you to cum right here in the foyer, pet. I want to see your juices flow down those lovely legs of yours." Mr. Jones purred.
I nodded and fingered myself even faster. It took only seconds for my orgasm to overwhelm me and I squealed loudly as my juices started to flow down my legs. I started to feel lightheaded and had to brace my clean hand on the door to prevent myself from falling over. As I was catching my breath, I realized that Mrs. Jones had dropped to her knees and was licking my juices from the insides of my legs. She was being careful not to allow her tongue near my throbbing pussy, but feeling her tongue grazing along my inner thighs almost provided me with a second orgasm.
"You taste wonderful, pet. I can't wait to taste more of you later." Mrs. Jones said seductively. "But for now, why don't we make our way to the sitting area?"
Mrs. Jones beckoned for me to follow her, which I did eagerly. She led me to the sitting room of the suite, where she took a seat on the couch, but indicated that I should remain standing in front of her. She picked up a glass of red wine and began to sip it as she looked me over. "How soon will you be ready to cum for me again, pet?" she asked.
"Mistress, I usually need 15 to 20 minutes between orgasm. I hope this is acceptable." I responded nervously.
"Perfect, pet, but I am going to challenge you. I will double your tip if you can achieve 3 more orgasms in the next 15 minutes." Mrs. Jones said coyly. "And you're going to start now."
Mrs. Jones stood up and walked back to the bedroom, then returned with huge dildo with a suction cup at the base. She licked the suction cup rather seductively and secured the dildo on top of the small coffee table. She then looked at me, winked, and sat back down on the couch. Motioning to the erect dildo, she said "You better get started, pet."
Somewhat concerned, because I had never had anything inside me as large as this dildo, I climbed up onto the coffee table and slowly lowered myself down onto it. To my surprise and relief, Mrs. Jones had apparently lubed it up before hand, for it slid inside of me much easier than I expected. Once it's full length was inside of me, and I adjusted to it's size, I began to fuck the dildo like a total slut. I humped up and down on it hard and fast, moaning and groaning, closing my eyes, focusing on letting the dildo fill my sopping pussy. As I was fucking the dildo, Mrs. Jones leaned forward and began to roll my rock hard nipples between her fingers, twisting them, pulling them, pinching them, all of which was enhancing my experience. To my surprise, I felt my second orgasm already building. I humped up and down on the dildo harder and faster, which seemed to encourage Mrs. Jones to molest my nipples even more. With little warning, my second orgasm overcame me, and I squealed in delight as my juices flowed all over the dildo filling my tingling pussy.
As I remained impaled on the dildo, Mrs. Jones got up and went a second time into the bedroom, returning what appeared to be two long leather straps, one of which separated into two thinner straps at it's midpoint. She also had another dildo with her, an inch or two shorter than the one filling my pussy. Without saying a word, Mrs. Jones wrapped the first leather strap around my waist and snapped it together just above my ass. The then attached the second strap in the front, had me stand up, and ran the strap between my legs effectively keeping the dildo inside of me. The strap separated and came up both ass cheeks and attached to the strap around my waist. I watched as Mrs. Jones then took the second dildo and secured it to the wall, about a foot off of the floor.
"Okay pet," Mrs. Jones began, "Get over here on all fours and let's see you take this lovely dildo in your ass. Four more orgasms to go, sweetie."
My legs were weak, and my heart was still beating rapidly, but I slid off of the coffee table and crawled over to the wall. I turned, and pushed my ass down on the dildo. It was lubed just as the one in my pussy was, so it slid in easily. I began to rock back and forth on my hands and knees, forcing the dildo deeper and deeper into my ass as I did. As I forced more and more of the wall dildo into my ass, I could feel the tip of it pressing against the tip of the long dildo secured in my pussy. Amazingly, I could feel my body beginning to tremble with it's next orgasm within moments.
As I continued to fuck the dildo on the wall, Mrs. Jones untied her sheer robe and let it fall to the floor. She then laid down and slid underneath me, taking my left breast in her mouth and sucking on it as she nibbled on my nipple. As she sucked on my breast, she wrapped her arm around my head and pulled my face down to her breasts. Eagerly, I opened my mouth and began to suck on her right breast. I played with her nipple, rolling it along the back of my teeth, moaning as she sucked on my left breasts and as I humped the wall dildo harder and faster. I could feel my body trembling, my orgasm nearing it's peak. Mrs. Jones could sense it as well, as she begin to bite harder on my left nipple, pinching the right one with her left hand, pushing me over the edge.
With a loud scream, I succumbed to my third orgasm in less than 15 minutes. My whole body shook violently as my juices spilled out from around the dildo and dripped down into Mrs. Jones golden hair. She slid further underneath me and began to lap up my juices as they rolled down my legs.
By this point, I was completely exhausted. I could barely keep myself up on my hands and knees. I was covered in sweat from head to toe. My pussy ached. My ass was on fire. My nipples were throbbingly sensitive. Yet, I could only think of how much more I wanted from Mrs. Jones, how much more I wanted to please her...to pleasure her.
Finally, my legs gave out and I slid off the wall dildo and collapsed onto the floor. Mrs. Jones sat next to me, running her fingers through my sweat-soaked hair. She leaned in and whispered in my ear, "Good girl. Rest now. You have earned your tip tonight, but I'm far from done with you, my pet."
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