I rubbed my hard cock against her wet labia, and slowly inched my way in. Even though Claire was so horny and wet, she was very tight. She closed her eyes tightly as I pushed my member past the silky walls of her warm pussy, moaning loudly with every inch of penetration. It took a minute or so, but I finally managed to enter her fully and the sensation of her pussy engulfing my cock was amazing. Her cunt was tighter, warmer and smoother than any other women I’ve fucked, and every thrust took all my self-restraint not to cum.
I helped myself to Claire’s breasts, grabbing and fondling them as I pounded her pussy. With every stroke, she was moaning in ecstasy and biting her lips, trying hard not to scream. I ravaged her pussy for five minutes as her love juices squirted out onto her bunched up skirt, and I held her by the throat as I continued banging her on the table. In the end, the aural stimulation of her moans and visual treat of seeing Claire in bondage being fucked by me was too much to bear.
I withdrew my cock from her pussy and quickly made my way to Claire’s face. It wasn’t a moment too soon as I ejaculated hot spurts of my man juices and landed on her perfect make-up. She probably thought I will cum on her body, so she was taken aback when I came all over her face. This was the ultimate fantasy for all the guys in the office, and I’ve heard some of the water cooler talk about how cool it would be to cum on Claire’s face. The warm splurts of sticky man juices landed strategically across her face, coating her hair, eye-lashes, nose and mouth with strings cum.
“Mmmmpph…” Claire protested as all my pent-up cum exploded and landed on her impeccable face. The cum pooled onto her eyes and threatened to flow into her nose, so I quickly used my fingers to spread the cum across her face, and into her half-opened mouth. I thought that she would spit it out, but she let me finger her mouth with cum in it.
“Swallow my cum,” I commanded her. She protested by shaking her head, and I placed my palm over her mouth to prevent her from spitting the cum out. After a few seconds, she relented and swallowed my cum in a single gulp.
I reached out for the box of tissues on another table to wipe my dripping cock - it would be difficult to explain cum stains on the carpet. Once I was done cleaning, I pulled out more sheets to help Claire wipe her face. As I turned around, I took in the beautiful sight of Claire bound on the table with her legs spread wide on the table, and my cum covering her beautiful face and perfect hair.
I helped Claire wipe my cum off her face and hair, as she slowly regained her composure. With the last bit of cum wiped off, she opened her eyes and I looked at her. “That was amazing. It was the best sex I had,” I said. She smiled coyly and replied, “I didn’t realize I enjoyed bondage and role-play that much too.”
Quote:
Originally Posted by
captainofthewin
nice story! i wonder how would TS handle Claire request to search for the document after this part..
btw upped u with my points alr
Thank you for the points… much appreciated. It is interesting and challenging to develop the story because I want to have some variation as to how Ben gets each lady in the team…
I kissed her gently on the lips. “You know… I’ve more tricks up my sleeves… you will like them. We should do this again,” I said as I gently untied her hands. She sat up on the table and she looked into my eyes, “I don’t mind being a friend with benefits… but only with someone who can keep secrets.” I reached over to the server rack, retrieved the hidden documents and passed it to her, “Your secrets are always safe with me Claire.”
She smiled as we got dressed, cleaning up the mess we created during our passionate sex. Claire looked into a mirror and exclaimed, “Oh shit… I looked like I got raped!” I glanced at her, and indeed she looked terrible. Her hair was in a mess, her make-up was all smudged, her clothes were in disarray and her skirt was stained by both our love juices.
Claire called Queen on her mobile, and told her that she needed to go home to settle some matters. She also informed Queenie that she found the document. Given the time it took to settle the document and how Claire had to go home after meeting me, it shouldn’t take much imagination for Queenie to know Claire had sex with me to secure the return of the document.
I unlocked the door of the server room, and Claire gave me a deep kiss before leaving. She placed a finger on my lips and reminded me, “This is a secret between us ok?” I smiled and replied, “Don’t worry… I know what to do.” She gave me a peck on the lips and whispered before leaving, “Keep in touch…”
It was more than a week since my sexual encounter with Claire, and the memories of the session were still fresh in my mind. I saw her a couple of times in the office, but she never made eye contact. Still, it made me smile when I see other guys in office ogling her from a distance, because they could only fantasize about it when I actually fucked her for real.
It was Friday morning when I arrived in office and I saw an envelope on my desk addressed to me. I opened it and a Mercedes key slid out, along with a note that said, “Will need your help tonight. Car is at basement 3 lot 34. C.” I guessed C was Claire, but I didn’t know what the secrecy was about.
It was 6pm when I was about to knock off work, and I received a message. “Ben, I’ll be drinking with some clients tonight. Can you pretend to be my chauffer and pick me up from Harrys at Harbourfront at midnight? Claire” I was befuddled by her request but decided to play along. “Ok sure, see you tonight.” I replied.
I decided to have dinner and stay back in office to work on some reports to pass the time. As it approached midnight, I locked up the office and went down to the carpark. When I located the car, I discovered it was a Mercedes E-Class estate. “Nice car… must be good to be this well-paid!” I thought to myself.
I was wondering what Claire was up to when she wanted me to pretend to be her chauffer. As I drove into the pick-up lane outside Harrys, I began to understand. She looked intoxicated, and she was with three other male clients who were trying to ‘help’ support her by grabbing her at all the wrong places.
I got out of the car and went over to help her out, as she waved goodbye to the clients. “Sorry about that… my chauffer’s here… let’s catch up next week to talk about the contract details!” The three guys were obviously upset that they couldn’t take advantage of her further. I sat Claire in the backseat, drove off as soon as I fastened her seat belt.
“Take a right turn and drive straight Ben,” I heard Claire saying from the back seat. I looked in the rear view mirror and saw that she was intoxicated, but not incapacitated. I followed her instructions and we reached a large dimly lit car park. I parked head in into a lot, turned off the headlights and set the parking brake, before getting into the back seat to check on her.
“Me too…” I replied. “I was wondering if you put it behind you because you never seemed to notice me at work.” Claire planted a soft kiss on my lips, “You know I didn’t want to do it at first,” she said. “But you don’t know that after that day, I really wanted to do it again.”
“But I didn’t want anybody in the office to know, so I had to play it cool,” she continued. “It was special because it was spontaneous. I really loved the roleplay and bondage…” she smiled. As the words left her lips, my cock was stirring and becoming engorged. “So I want our second session to be just as special… and memorable.”
My mind was racing, and I guessed car sex or sex in a public place aroused her, which was why she wanted me to park there. As I leaned in to kiss her, she stopped me and pushed me back. “No Ben… not like this.” I was confused as to what she wanted.
“I have a fantasy…” she admitted. “I always fantasized about being a powerful female CEO who ill-treats her chauffer…” she said. “And one day, the chauffer took revenge by savagely raping her in car. Can you fulfil my fantasy Ben?” she said while gently caressing my growing bulge. I looked around the car park, and it was truly dark, empty and deserted.
It should be pretty safe unless a police patrol car decided to check us out. I decided to take the risk and go ahead with the deed. “Alright… let’s do it,” I agreed. Claire leaned over and kissed me on the lips, “Thank you Ben! I know it’s just a fantasy roleplay, but please make the rape realistic. You can be as rough and violent as you want, so long as there’re no bruises and scars that others can see tomorrow.” That was the first time that any ladies wanted such realistic roleplay, so I was slightly concerned it could be an entrapment.
“Wow… you sure about that? I can get pretty forceful when I am aroused you know…” Claire smiled and replied, “You remember the last time when I had to go home after we had sex, because my clothes were messed up and stained? I’ve a spare set of clothes today, so do whatever you want to me…”
I nearly choked on my own saliva at that moment. It wasn’t just what Claire said – it was the sensuous way she said it. “Alright… I can do that if that’s what you enjoy. But we should still have a safe word in case I go overboard” I insisted. “How about ‘document’?” Claire smiled.
With that, the game is on. I got out of the back seat and returned to the driver seat, playing the role of Claire’s faithful chauffer. I looked into the rear mirror and announced that we’ve arrived. “Miss, we’ve reached home.” Claire pursed her lips and glared at me through the mirror, “Are you being dense or are you really stupid? Two years on the job and you can still forget that you need to open the damn door for me when I’m wearing heels. No wonder you’re just a lowly chauffeur!”
I took a deep breath and looked away. Claire was so scathing in her remarks I wonder if she was role-playing or it was really her talking. I got out of the car and went over to her door to help her out. She stepped out of the car unsteadily and clung to me for support, due to the uneven ground and her 12cm stiletto heels. The heels added more tone to her long fair legs, and complemented her outfit really well.
“Be careful Miss,” I held her arms as she nearly slipped. I could smell her perfume and feel her warmth in the cold night air as I held her close. “Be careful where you are grabbing, you moron. These are designer clothes… it’ll cost you three months’ salary if you dirty them!” she seethed.
“Sorry about that, Miss. I’ll be careful.” I replied, secretly close to my breaking point. “Get the flats from the boot so I can change out of these heels… they’re killing my feet!” Claire ordered. I opened the tailgate and sat her on the ledge of boot, and retrieved her flats from the boot.
Claire glared at me when I handed over her flats, “Oh god you’re really dumb. I’m wearing a tight skirt… how do you expect me to reach my feet and change the shoes myself? Can you take some fucking initiative and change my shoes for me? Seriously… do I have to teach you everything? Are you retarded?”
That was some world-class acting there, and if I had a boss like that in real life, I’d quit immediately. Claire was really hamming it up to make her chauffer angry enough to trip and get her for it. I kneeled down in front of her as she stuck her leg out, and I slowly undid her heels and slip it out of her feet.
Claire had perfectly formed feet to match her long slender leg, and I was really turned on by her feet enveloped in black silky stockings. I kneeled there mesmerised by her feet in my hands, and I involuntarily caressed her feet and trailed my hands up her lower thigh.
“What the fuck do you think you’re doing!” Claire screamed and broke me out of my daze. She pulled her leg back and kicked me to the ground, “How dare you touch me, you piece of shit! You’re just a fucking useless driver! You’re fired!”