The Cunningham’s Babysitter (Part 1)

My heart raced as tow men approached me. I still couldn’t believe I had agreed to this. They told me that they could give me one hell of a night to remember and all I had to do was to show up to Club B, the country’s most expensive club, at 7pm sharp. And here I was, standing at the opulent entrance, flanked by two men in black three piece suit and tie.

“This way, Ms. Sanders.” one of them ushered.

My lips trembled so much in fear, or excitement, that I didn’t dare to speak. I was afraid that I would sound like a distressed whimpering puppy. I simply followed the men through the large entrance and into the fine establishment.

The lobby of the club was as grand as the entrance. Large columns placed in strategic location that made this place seemed like a 17th century opera house. The floor was sparkling as it reflected the glimmering ostentatious chandelier hung above. Two wide stair cases arced perfectly as it link the lobby to the landing one floor above. In between the two stair cases was a oil painting depicting several men and women engaged in an open orgy. Could they be more conspicuous with the whole sex thing?

I was so focus with the details of the lobby, it hadn’t occur to me that I was escort to a concierge. A man with similar black suit stood behind the black marble counter bowed slightly when our eyes connect.

“Greetings, Ms. Sanders. I have been told by Mr. and Mrs. Cunningham to get you to room 305.”

Mr. and Mrs. Cunningham were my employers. Mr. Richard Arthur Cunningham was a influential business conglomerate with a net-worth of several billion USD. Mrs. Helen Courtney Baxter-Cunningham was a renown lawyer that partnered with one of the country’s leading law firms. Me? Well, I was just a uni student doing odd jobs to keep my landlord from bugging me, my fees duly paid and food on the table. The Cunningham hired me to help them babysit their three year old son, Johnny, while they went to work. And they were extremely generous with their payment. A hundred dollar for a few hours, lunch included, what more could I ask?

One day, they insisted that I stayed for dinner and perhaps because of the wine and the food, we began to talk about stuff beyond our comfort zones. Actually, I wasn’t so sure if it was beyond their comfort zones because they seemed awfully jovial talking about it. It all started out with a casual conversation about our sex lives but then gradually, they exposed to me their greatest secrets. For a couple of hours, I listened to their experiences and their fetishes, and before I knew it, I was rubbing my thighs together.

“Please sign the NDA form.” the polite concierge pulled me back as he laid a piece of paper on the counter and pointed an expensive fountain pen on the space at the lower right corner.”If you would just sign here, please.”

The pen was already uncapped when he handed to me and I didn’t hesitate to sign. Luckily, none of them had seen my signature before, because if they had, they would know that I was freaking nervous. I passed the pen back to the man and pushed the paper slightly towards him.

“I’d also need your cellphone or any device that has recording capability.”

The Cunningham told me about the form and confiscation of any recording device, sparing me the need to ask the concierge why. I fished out my smartphone from the small expensive clutch that Mrs. Cunningham was kind enough to lend me and handed it to the concierge.

“Thank you, Ms. Sanders. Please follow these two gentlemen.” he cast a lopsided smile and bowed ever so slightly. “Enjoy your evening.”

What did he mean by enjoy my evening? I couldn’t push away the feeling that he knew exactly was going to happen to me. One of the two men gentle pressed on my shoulder to turn me around. I followed them as they walked. I didn’t know what to do. This whole thing seemed so new to me. As I walked up the opulent stair case with the men to the landing above, I thought about all the things they’d told me during the overstaying.

“Have you heard of the word, BDSM, love?” Mr. Cunningham, ever so polite, asked as he sipped on the Whiskey.

“I’ve heard it a few times from some friends. But I don’t really know what it means.” I lied, of course. No one wanted a babysitter that had sexual fantasies involving ropes and rough sex. Especially not sophisticated people such as Mr. and Mrs. Cunningham.

“Technically, it’s not a word, dear.” Mrs. Cunningham added. “It’s four words, Bondage, Dominatrix, Sadism, and Masochism. Shortened to B.D.S.M.”

I simply nodded. I knew exactly what those words meant, hell, I even watched a couple of BDSM porn movies with my bffs a year ago. I composed myself and faked oblivion, and began to wonder why these two sophisticated people decided to touch on this subject.

“Are you familiar with any of those terms.” Richard smiled at me. Oh, that smile. I wondered how many women had been melted by that lovely smile of his. I had no doubt that the number reached more than a few dozens. And I was sure I was one of them.

“I think they have something to do with kinky sex.” I managed to come up with the most innocent answer. I thought I did. Richard chuckled, as if the answer amused him. I turned my eyes towards Helen, feigning innocence. Helen turned to me with a knowing smile. Shit! They obviously knew that I knew.

“Just by saying that, means you know what it is, love.” Richard said before sipping another mouthful of Whiskey.

I blushed at the blatant remark and lowered my head. My fingers seemed to be the most interesting things to watch right this instant.

“I’m sorry I lied.” I mumbled, feeling somewhat guilty.

“Don’t be silly dear. You don’t have to apologize for that. In fact, we are pleased that you try to be discreet about your sexual endeavors.” Helen pulled my head up to meet her eyes. When our eyes connect, I felt my stomach cringed. Her eyes were burning with lust and I could see that she was sizing me up like I was her prey.

I never could see myself having sex with a woman, but when I looked at Helen, I began to question my sexual preference. Her curvy brown hair suddenly seemed more lovely than usual. And before I could stop myself, I found myself appraising her breasts. Helen obviously saw my little sight seeing as she smiled.

“Ms Sanders?” one of the men broke my train of thoughts. “Please go in.” he gestured politely to the elevator.

“Oh. I’m sorry.” I apologized.

I gave him a weak and nervous smile before walking into the expensively decorated car. The elevator was carpeted and a soft orchestral music was being played inside. I recognized the melody. One of Vivaldi’s masterpiece. The man tapped his card onto a grey square conspicuously placed below the matrix of floor buttons before pressing the 3rd floor button. The security here was sure tight, because I had never seen an elevator that needed a key card except in television showing some spy movies. Suddenly, I had the urge to ask them a question, because I felt weird that I was the only one being flanked by two men in black. None of the patrons I saw at the lobby were with men in black.

“Why am I the only one being escorted?” I stuttered.

“Club rules, Ms. Sanders. All guests must be escorted at all times.”

“Then those people who aren’t escorted?” this time I managed not to croak.

“They are members.” he said simply.

“I see… Why the tight security?”

When elevator chimed our arrival and the reflecting door parted, my question was answered. A woman, prostrated in front of me, with her ass in the air and her fingers prodding her own opening, greeted me. I gasped in surprised and quickly clasped my mouth to stifle myself. The man sitting on one of the single seat couch smiled at me as if he was pleased to see me there.

“Clara, someone is watching you. Show them just how naughty you are?” he spoke salaciously to the prostrating woman.

“Yes, Master.” the woman whimpered and rubbed her opening harder and faster and her moans gradually louder.

“Shit!” I cursed under my breath and quickly followed my escorts out of the elevator, trying not to look at the woman. Okay, I’d read about this before. She must be an exhibitionist. I had to say that the idea of letting some strangers watched you masturbate sure made my stomach cringed.

“Might I ask if you would please stay and watch until she finishes?” the man requested. He fucking requested me to watch her masturbate!

“Should I?” I asked one of the escorts and they simply told me that it’s up to me.

I debated quickly inside my head. Did I want to watch? Well, watching a woman masturbate wasn’t exactly in my to-do list. But the woman did seem to enjoy exposing her hoo-ha to the spotlight. Should I amuse these two? After several seemingly long seconds had passed, I made up my mind and stoically nodded.

“Thank you.” he said with a lopsided smile. “Clara, this kind lady has agreed to stay. You don’t want to disappoint our viewer, do you?” he said in the most sultry tone I’d ever heard. I felt my inside turned to jelly just by witnessing these two playing out their fetish.

The woman, Clara, tensed subtly and began to push her two of her fingers inside her dripping wet opening. Granted, this wasn’t what I had expected, but this was the wettest pussy I’d ever seen in my life. Her juice practically leaked out and dripped onto the expensive looking carpet that covered the whole hallway. There’s even a large damp spot on the carpet beneath her. How long had she been touching herself?

Even though watching her masturbate was somewhat entertaining, I was curious about the two escorts that had no choice but to watch with me. I looked below their waists and sure enough, the evident budge were obviously visible. Even they weren’t immune to this. After satisfying my own curiosity, I turned  back to the lewd woman in front of me. Oh God! Now, she’s using two hands, one prodding her moist entrance while the other teased her own clitoris.

As I watched, I began to feel the ache between my legs. I clamped my thighs together to temporarily relieve the sudden urge to masturbate right that instance. My juice began to seep out, making me really uncomfortable. I wanted to squirm to better relieve myself but that would be too obvious.

After about a minute of relentless teasing and prodding, the woman finally released an explosive orgasm, literally. Squirts of clear fluid sputtered out of her wet opening like a water jet as she shuddered in delight. It was almost like she was peeing. My eyes widened in disbelief. I couldn’t help but to mentally measure the distance the liquid flew through. It was at least 5 feet. Shit! Even peeing wouldn’t get me that far.

“Thank you for staying.” the man said appreciatively before standing up and helped the exhausted woman up on her feet. She practically clung onto him as he lifted her up, princess style. Naked princess style.

I couldn’t help but blushed. I had never witness something like this. Who was I kidding? I didn’t even know pussy could squirt that much that far. Nevertheless, I quickly composed myself and nodded in acknowledgement. My escorts got the obvious hint and turned around quickly, as if they were embarrassed by it. As I followed them, I realized just how much I needed to masturbate after witnessing that. And that very fact made me wondered if these two needed the release as well.

“How do you…” I contemplated, trying to find appropriate words, “cool off.”

“That’s none of your concern, Ms. Sanders.” both of them said politely in unison. Obviously, this wasn’t the first time they were asked this question.

When we reached room 305, the one on my right pressed the doorbell. That’s what I thought, even though no sound was heard. Usually, when I pressed the Cunningham’s doorbell, I could hear a faint chime coming from behind the door. For this case, there was no sound at all.

The lock clicked and the door swung opened. Mr. Cunningham was standing, his 6 foot 7 figure towering my 5 foot 6.

“Thank you for bringing her up.” he nodded to the escorts and handed each of them a hundred dollar tip. $300 dollar tip just for bringing me up? I needed to babysit three times to get as much. The Cunningham’s good to me, don’t get me wrong. In fact, the best out of all my other employers. But the fact that he paid them $300 each just for bringing me up 3 floors and, well, watching a real life pornography with me, made me a bit jealous. Okay, maybe not just a bit.

“Well, come on in.” Mr. Cunningham ushered me in with the usual politeness, seemingly oblivious to my green horns.

I cast my jealousy aside and walked into the suite. It was completely styled in Victorian decoration. Expensive erotic arts strategically placed on the walls. In the middle, hanging on the ceiling, was a smaller version of the chandelier at the lobby, showering the area with warm orange light. There were 3 couches, which matched perfectly with the floral pattered wallpaper and wooden floor, arranged in a U shape, with the center of it was a weird looking, overly rectangular, coffee table.

On the couch was Helen, wearing an equally elegant dress as mine. Hers made her look sophisticated and I envied her natural beauty. She was slightly over thirty years old but looked more like a university fresh graduate than a renown lawyer. She stood up when she saw me and walked to me.

“I’m glad you came. I was beginning to worry that you might not come.”

“Sorry, I’m late. There’s uhm…a show, going on…at the hallway.” I explained, all the while blushing.

“Ah. You must be talking about Leroy and his wife, Clara. Clara’s an exhibitionist. Sometimes Helen and I watch them too. It is very arousing if I may say so myself.” Mr. Cunningham said behind me, his hands holding my shoulders. I couldn’t help but to feel the burning sensation of my skin sizzling under his touch. They were still as polite as ever even though what we were about to embark on defied the very core of conventional morality.

“Kimberly, are you sure you are alright with this?” Helen now stood directly in front of me. She was slightly taller than me and with Richard behind me, I was being sandwiched and that made me felt small. I gave a nervous chuckle before nodding.

Was I okay with this? Well, I was more than okay. I was bored with my sex life. It was always mechanical, penis in penis out, penis ejaculate and penis went fucking limp. Repeat process. Fuck. I was tired of that. The Cunningham gave me an option to spice things up. How could I say no?

“I’m ready.” I reassured them.

“Okay. Now, we are going to blind fold you. Love” Richard whispered into my ear with the same sultry tone as the Leroy. Oh, it’s starting!

From behind, he placed a soft strip of satin over my eyes before tying it snugly around my head. With my vision taken away, I realized my other senses was heightened. I could hear Mr. Cunningham’s low, breathing sound. When Mrs. Cunningham touched my arms, it almost felt electrifying. Her smooth hands rubbed along the length of my arms before catching my hands. Gently, she tugged me and I followed her. I had the layout of the room in my head and judging by the sharp turn, I had no doubt that Mrs. Cunningham was leading me to that weird coffee table in the center of the U-shaped sofa.

Without warning, I felt a small tug on my dress and the familiar zipping sound filled my ears. I was being stripped. Mr. Cunningham was unzipping the zip at the back of my dress.

Mrs. Cunningham let go of my hands and suddenly, the smooth dress fell to the ground. I gasped at the sudden exposure of my skin.

“Good girl.” Mr. Cunningham praised as he caressed my bared breast, clearing appreciating my obedience for not wearing any underwear as previously told.

“Oh dear.” Mrs. Cunningham chorused, “You are wet.” her fingers rubbed against my wet opening. I reflexively pushed her hand away from me and pressed my thighs together.

“That’s not good, dear.” Mrs. Cunningham reprimanded softly as she lightly slapped my shielding hands. I shuddered at the soft touch of her palm. Even though she hit me lightly, it felt more painful than it should be. And it made me feel guilty for my action.

“Kneel and then bend down.” Mr. Cunningham ordered.

I got down to my knees and bent down until my bare breast pressed against the soft cushioning that I didn’t expect. Now I knew why the coffee table looked weird. The top was layered with some kind of leathery material.

“Spread your legs.” Mrs. Cunningham said sultrily. I spread my legs without hesitation and felt something wrapping around my thighs. With a forceful tug, my thighs were secured against the legs of the table, effectively opening me up. After that, my arms followed the same fate as the Cunningham expertly fastened the belts around them. When they were done, I was completely opened and bared, not to mention how defenseless I suddenly felt. No more shielding my pussy.

“What is your safe word dear?” Mrs. Cunningham asked. I silently thanked her for still concerning my safety. At least someone was still thinking straight.

“Alan Turing.” I croaked, but instantly regretted for using the name of a great mathematician in the sake of kinky sex.

“Hmm…is that someone special to you?” Mr. Cunningham cooed, obviously ignorant about the significance of that name.

“He cracked the Nazi’s enigma.” I explained, although I knew they probably didn’t know what I was talking about. “A great mathematician in the 20th century.” I added breathlessly. The Cunninghams, after realizing the man was a famous figure of the past, laughed at my choice for safe word.

“I bet he’ll be honored that you use his name for such exotic occasion, dear.” Mrs. Cunningham chirped. I could feel her index finger trailing along my bare back, moving from my neck to my tailbone before coming back up again. I whimpered at the sensual, yet deliberate touch.

My body tensed up when Mrs. Cunningham seized my earlobe with her teeth, nibbling my sensitive flesh softly. The rumbling hum breathed to my ear sent my body into ecstasy, causing me to squirm on the leathery surface.

“Now, tell me, Kimberly. Why are you so…wet?” her finger went down my spine, passed through the trough between my butt cheeks and ran along my sex the same time the word ‘wet’ came out of her mouth.

My thighs tensed at the contact but with the belts, they remained reluctantly open. Mrs. Cunningham seemed to enjoy my reflexive reaction as she purposefully rubbed along my wet opening harder.

“You must be a naughty girl to be this wet.” she breathed into my ear, setting my nerves on hyperdrive. I could only whimper to the statement. Her carefully loaded words turned my inside into mush. Even the word ‘naughty’ made my pussy throbbed desperately.

When two rough hands groped firmly on my butt, I let out a surprised gasp. The two hands then pushed my cheeks apart, as if to allow more access for Mrs. Cunningham’s teasing fingers.

“My husband wants to fuck you. He’s hard.” Mrs. Cunningham continued. “Do you want him to fuck you?”

“Yes.” I breathed. “I want him in me.” I couldn’t believe I’d just blatantly told the wife that I wanted her husband to fuck me.

“I’m sure you do. You are such a naughty girl.” she chorused ominously. “Naughty girl needs to be punished.”

Out of the blue, a hard slap landed on my left butt cheek. I squealed at the assault. It wasn’t exactly painful but the strike did cause my body to convulse. I felt Mrs. Cunningham was moving around me, her fingers never left my wet pussy.

Another slap came down hard, this time, on my right cheek. I groaned in pleasure. The smack certainly awoken something inside me because I had never felt so aroused before. Helpless and defenseless and being at their mercy electrified a new urge within me. My head began to swirl at the sensory overload.

Without so much as a warning, Mrs. Cunningham’s fingers plunged deep into my sweet opening. I squealed in delight at the delicious invasion. Oh God! She knew exactly how to finger a pussy because this was by far the best fingering I ever had in my entire life. It was even better than fingering myself on my own. Silently, I thanked the belts for holding my thighs apart. She was too good and my thighs involuntarily wanted to shield my overly stimulated pussy. With my brain’s a mess, I couldn’t keep my legs apart even if I wanted to.

“Oh God! That feels so good.” I mumbled, which instantly rewarded me with a succession of slaps on my butt cheeks. My body tensed at the merciless assault to my ass and when the slapping stopped, my cheeks felt bare and hot.

“I think we better put that mouth to some good use.” Mrs. Cunningham said, her tone almost sounded commanding. When the hands disappeared from my butt, I knew what was going to happen. A hand grabbed my hair and gently lifted up my face. I still couldn’t see but the smell and heat coming from in front of me told me Mr. Cunningham’s intention.

“Open your mouth, love.” he ordered. I obeyed.

His manhood filled my entire mouth. I’d never seen his cock before but I knew from this moment that it was thick and long. He pushed his instrument deep inside my mouth until I almost gagged before quickly pulling it back out. I was a bit surprised, not by him, but by myself because I realized that I actually liked this. I never had fellatio before, not this deep at least. I might have kissed a cock or two, but all the way in, no. This was definitely the first, and I absolutely loved it.

The lustful smell and the salty taste were nerve wreaking. I couldn’t believe how much I actually loved it. When he pulled out, I found myself opening wider, yearning for his presence in my mouth. Knowing just how wanton I was, he pushed himself into me once again. I sucked on his length hungrily, wrapping my lips around his hard tool. My tongue flickered on the tip, savoring the salty liquid oozing out of him.

“Her mouth is divine.” Mr. Cunningham groaned as his gently eased himself in and out of my mouth.

All the action made me forgot about Mrs. Cunningham. I didn’t even realize when she wasn’t teasing my pussy anymore.

“Well, I suppose I can use her pussy then.” she cooed. The word ‘use’ made me shivered. It was as if I was some kind of toy for them to play with and that made my pussy clenched attentively.

“Remember that you told me about how dicks go limp too soon? My strapon doesn’t have that problem.” she added and almost immediately, I felt something thick and hard pushed against the lips of my pussy. My thighs strained to clamp shut as the thick length slowly pushed my folds apart and gradually filled me up. I whimpered incessantly.  It almost felt like an eternity when finally, her hips were pressed against my sore ass.

I felt her smooth hands on my waist and seconds later, her fingers gripped onto my small hip as she began to thrust. I yelped at the brutality of the intrusion. My body arched as the thick rod rammed into me. It was the total opposite of Mr. Cunningham. It was the hardest fuck I’d ever experienced. Mrs. Cunningham was a refined woman and it had never crossed my mind that this woman was so much more. Her hips slapped onto my butt cheeks as the thick tool pumped in and out of me hard and fast. I clawed at the wooden legs of the table trying my best to keep my sanity. Moans escaped my throat like that was the only thing my throat was capable of at that moment. Her thrust was so hard, I found myself being pushed forward, taking in Mr. Cunningham’s tool deeper into my throat.

In that moment, the only thing I could think of was the tingling feeling building between my legs. I felt like a complete toy, to be played and used by the two people in front and behind me. The thought made my pussy clenched in excitement, gripping the slippery dildo harder than it already was. As the feeling between my legs build up, I found Mr. Cunningham began to thrust into my mouth harder by the second.

“I’m going to cum.” he announced.

He’s going to cum in my mouth! Oh! The thought was exhilarating and the ache building in my pussy worsened substantially. I shivered at the thought of white hot cum from Mr. Cunningham’s cock poured into my mouth. What would it taste like? Should I swallow it? Oh, why am I so fucking aroused by it? Oh shit! I’m about to cum! Shit! Shit! Shit!….

“I’m coming…I’m coming!” he exhaled, his thrust gained momentum.

Finally, his hands pressed my head hard against his hips, his length all the way inside me and the tip rested at the opening of my throat. Warm salty liquid spurted out and went directly into my throat. I swallowed instinctively, in fact, almost choking. And few seconds later, my body convulsed and I released a mind boggling, nerve wreaking orgasm. My carnal cries were muffled by the large cock inside still my mouth. My body tensed and before I could recover from my current orgasmic state, Mrs. Cunningham’s ceaseless thrust into my overly stimulated pussy pushed me over the edge the second time.

“Fuck!” I muffled. She wasn’t stopping. It was my second orgasm and Mrs. Cunningham was still ramming that thick dildo inside me. Oh God! She’s not stopping! My thighs clenched desperately, trying to protect my pussy from the carnage but the belts kept them helplessly at the side. Mr. Cunningham pulled out of my mouth and I gasped for air.

“Please. Stop! Stop it…I’m…shit…I’m going to….emmmmm….ahhh” I croaked.

“You…are…going…to…squirt!” she said each word with a hard thrust.

I shook my head violently. My eyes rolled back. My throat trembled with squeals. My toes and fingers clenched into fists. My thighs strained against the belts. My body convulsed erratically. Finally, my pussy clenched. It was too late. There was no holding back. I arched my back and gave a low, inhuman groaned as my body unleashed the more explosive orgasm ever. Clear fluid gushed violently out of my pussy. Mrs. Cunningham had gotten what she wanted. For the first time in my life, I was squirting!

The next thing I knew was my face hitting the leathery surface. The triple orgasm had robbed every last ounce of strength from my body. Thoroughly used and completely sated, I let my mind wandered in the darkness and before I knew it, I was already sound asleep. Or more like passed out.










About robsam1991

Even though my stories depicts rapes and violence on women(mostly), i never once condone the action. Not even the slightest. In fact, i despise men who rape women. I never agreed on that women who wear provocative clothing were to be blame on for the rape; though they should take precautions when necessary to avoid risk. As a man, i think it's our responsibility to control ourselves and never let our urge out on innocent people. If you feel like raping someone, then treat a girl nicely so that she would opt for a role play where you can play out a 'rape' on her satisfyingly. Please use safe word.
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