My New Boss Pt. 27

As Brian pulled out of my driveway, I gave Suky a quizzical look.

"Our vacation," she repeated slowly, as if she was communicating with a simple person. "The reward for Steph and I, for Tim's big promotion."

My heart sank as I realized that this dreaded day was fast approaching. My boss, Tim, was taking my girlfriend, Suky, my dream girl, Steph, and his teenage Thai fuck-toy, Ana, on a three week vacation. In their absence, I was expected to tend to Fat John's every need, lovingly pampering him during his Saturday morning massage parlor session. As much as I was going to miss Suky, I was dreading having to accommodate Fat John's increasingly perverse sexual appetites.

I hadn't met Ana, but I knew she had to be absolutely stunning, for Tim to halt his endless quest for young pussy, and declare her to be his girlfriend. As the new Global Head of our company, he had chosen to remain based in Bangkok, which should have been a clear indicator of how much fun was to be had there, as a single guy.

The night before their departure on vacation, Steph and Suky were beside themselves with excitement. They had emptied their entire closets, trying to decide which outfits to take on their three week vacation. Once their suitcases were full of clothes, they enlisted my services to help close the overly stuffed luggage. They each had two huge polycarbonate designer suitcases, bright pink in color, with their names stenciled on the side. I was dismissed right after I managed to get the bags closed and secured, although I heard them hooting and hollering for several hours, after they sent me to my room.

In the morning there was no sign of the girls. Their suitcases were exactly where I had left them the night before, piled up by my front door. I knew Tim would be arriving shortly, and in his continuous attempt to emasculate me, would expect me to load their bags into the cab. For this reason, I waited anxiously by my front door, intending to split right after my service was complete, so that I didn't have to witness them leaving.

Tim, because he loves to rub my nose in it, pulled into my driveway in the rear seat of a Town Car. Well, I say Town Car, but it was actually a Cadillac Stretch Limousine, beautifully detailed and imposing, as it parked right in front of my garage, thus preventing me from leaving.

Tim remained in the car, and the driver opened the trunk remotely, which was my signal to load the girls' luggage. As I carried the first case to the trunk, I noticed two identical pieces of luggage had already been loaded, the name Ana stenciled neatly on the side to prevent confusion. Once the four pink suitcases were stowed in the cavernous trunk, Suky and Steph came out of my front door, heading towards the limo.

They were dressed identically and looked really sexy. They were both wearing hot pink silk mini-skirts, with matching crop-tops, that exposed their tight stomachs. They had on matching high-heeled stilettos, pink fishnet stockings and large oversized pink sunglasses. These glasses concealed their makeup, but I did notice both of them had beautifully glossed pink lips. They each had a large pink bow in their hair which was a very feminine touch. Lastly, both girls carried matching pink Gucci handbags.

They looked very sexy and extremely expensive. It felt like my boss had orchestrated this display of wealth, and ownership of the girls, by blocking my exit with his limo as his playthings got in with him. They had to walk right past me to get into the car, and I could smell their perfume was identical, as they got close to me.

As they approached the limo, I spoke.

"Have a safe trip guys," I said, trying to conceal my jealousy.

Neither of them responded, in fact there was not even any acknowledgement of my existence from either girl. They didn't break their stride, or look my way, but just got into the huge Cadillac with my boss. For whatever reason, Tim had left the rear privacy screen down, so that I could see right into the limo. They both seemed very happy to see Tim, hugging and kissing him on the lips, as I watched through the rear window.

Another young girl appeared in the rear window, her head apparently having been in my boss' lap as he pulled into my driveway. I couldn't see much of her as she was hidden by Suky and Steph's enthusiastic greetings, but I could tell that she was Asian and very petite. I assumed it was Ana, but I was more interested in my girlfriend's behavior.

I had a pang of jealously, as I could clearly see the four of them in the rear seat. Tim was sitting in the middle of Suky and Steph, and they were nibbling his earlobes as the car started to pull away from my garage. Then, in unison, they pulled their lips away from his ears, and both of their heads disappeared into his lap. It was a real kick in the nuts for me, and was clearly done to mess with my head.

My boss reclined his head back onto the rear headrest, and was kissing Ana, as Suky and Steph apparently serviced him. The limo was crawling down the driveway, and finally the rear privacy screen closed, thus eliminating any view I had of the three young women pleasuring my boss.

I never heard from Suky in the three weeks that she was on vacation with my boss, even though I texted her numerous times. My only connection with her was through my boss' Facebook page. Inexplicably, right after they left for their vacation, Tim friend requested me, and after I accepted I was hooked on his page. Even though it stoked my jealousy, and made me vow to stop looking at his feed, I was addicted. There were multiple posts a day, highlighting their extended vacation, and it was apparent that the four of them were inseparable, and having so much fun.

His posts were quite sexual in nature, designed to elicit envy from his male friends (and pure jealousy from me). In fact, I was hooked after his first post, the four of them lounging seductively on the biggest bed I have ever seen in my entire life. Apparently, upon arriving at the Royal Palm Beachcomber Resort in Mauritius, the Manager upgraded the unorthodox group to the Honeymoon Suite, which as I checked on their website, boasted of the double-sized King Bed.

The first photo that Tim posted, presumably taken by one of the bell-hops upon delivering their luggage to the Suite, showed Tim lying in the middle of the massive bed, in just a pair of white linen pants. I figured that they had just checked in, as the bedside clock indicated that it was eleven in the morning.

The three young women were draped all over him, their intent to pleasure this man written all over their youthful faces. Tim made no attempt to conceal his erection, and, to my surprise, it was the angelic Steph who had her perfectly manicured hand on his abdomen, right above the tip of his cock as it struggled against the waistband of his linen pants.

Steph had gone to great pains to inform me that she had very limited sexual experience with men, and now, in stark contrast to her claims, she was making herself available to this man. This couldn't possibly end well for her. Tim is a true Alpha Male, in every sense of the word, and if he sensed any weakness on Steph's part, he would make her pay.

I set up an alert on my phone, that notified me whenever Tim posted something new, and less than thirty minutes later, my phone dinged. The bedside clock had only advanced by twenty-five minutes, and yet things had apparently moved very quickly. This photo showed a much more relaxed Tim Andrews, stood next to the bed, with Steph kneeling by his side.

She was looking up at him with adoration in her baby-blue eyes, and his hand was resting on the top of her head, as if he owned her. His erection was apparently gone, although he was using his spare hand to hide his crotch, in accordance with the strict rules that Facebook has, to prevent overly sexualized, or graphic photos. Steph had applied some clear lipgloss to her lips, and looked absolutely stunning.

The comments started to appear almost immediately, referencing Tim's relaxed demeanor and Steph's newly applied clear-coat. The inference was that she had sucked him off, although with Facebook's moderators eager to suppress any indication of sexual impropriety, the comments remained veiled.

A few moments later, my phone dinged, inviting me to join a Viber group. I accepted immediately, expecting it to be from Tim, in an attempt to circumvent the puritanical censorship of Facebook. The invitation was from Tim, and shortly after my acceptance, I received some additional photographs of their morning check-in, that left no doubt that Steph had indeed sucked my boss off.

Even though I should have realized that the invitation to go on vacation with my boss, was predicated on sexual favors, it still made my heart sink to see that goddess on her knees, with his cock between her lips. Especially as it confirmed my suspicion that Steph's newly applied clear-coat, was actually my boss' semen.

I browsed through the newly sent photos, my cock stiffening as I took in Tim's total control of the young blonde. He had removed his hand from his crotch in the next photo I viewed, taken just prior to her sucking him off. His cock was clearly visible tenting in his linen pants, a large wet spot having formed at the tip. There were traces of Steph's light pink lipgloss around the Velcro opening of his pants, presumably from where she had tried to remove his cock from the confines of the linen, using just her lips.

Tim had a very smug smile on his face, and had titled the photo, "Steph's first real blow-job, to completion!"

I knew this was a reference to the fact that while Steph had sucked my cock in the shower, she hadn't allowed me to ejaculate. That asshole always had to one-up me, and I ended up receiving photographic evidence of many of Steph's "firsts." Predictably, Tim sent me a picture of Steph right after he gave her a facial. She still looked angelic to me, even with his semen splattered across her snooty little upturned nose. Then, as my boss took Steph's anal cherry, Suky guided his cock inside the young girl's virgin anal passage, one hand on his cock-head, the other giving an enthusiastic thumbs-up to his latest conquest.

It all seemed very personal to me, my boss enjoying the sexual delights of my girlfriend and my dream girl. The barrage of photos was endless, and it appeared that all they did was find inventive and exciting ways to get him off. I jerked off every day to the photos, typically after having sprayed a healthy spritz of Suky's perfume in the air. Part of me wanted them to stay on vacation, however sordid the details they shared with me, just so that I could enjoy being off sexual restriction.

There were changes afoot when they moved the party to Thailand. Tim was obviously enjoying all three of Steph's orifices, but when they got to Ana's homeland, he needed to get rid of the young blonde. He was there to spend time with Ana's family in the very poor Isaan province, and the American teenager stuck out like a sore thumb.

Steph had served her purpose and he decided to send her home. He didn't give her too much input on the decision, merely telling her to pack her shit, as the taxi would be there in an hour to drive her to Bangkok International Airport. Steph held it together until she got on the plane, but when I picked her up at LAX, she was distraught.

"It's all my fault," she cried repeatedly, as I drove her back to her place. "How did I expect to be able to compete with Ana and Suky? They are both experienced courtesans, have had numerous lovers, and have been in multiple relationships. I am an inexperienced teenager, with no clue how to satisfy a man. What was I thinking?"

I wanted to tell her that when you look like she did, you can pretty much just lie there and men will come hard just from admiring your beauty. However, I sensed an opportunity and so I took another tact.

"Why don't you work in the massage parlor for a few weeks?" I suggested. "That way when Tim gets back from his vacation, you will have a lot more experience with men, and will be better equipped to rock his world."

I had hoped that Steph would respond in a certain manner, and I wasn't disappointed when she spoke up.

"Could you teach me, how to pleasure a man?" she asked innocently. "Tim will be home in a week, and I would love to be able to keep him happy, once he gets back to LA."

"I don't know, Steph," I said, trying to contain my euphoria at the prospect of a week with the teenage blonde as my sex-toy. "That's not as easy as it sounds."

"Please," she implored me, holding her hands together in the universal sign for begging.

I ended up agreeing to her request, taking a week off from work, which was met with zero resistance, as I had just been passed up on an important promotion, and needed time to "reassess my priorities."

That week, in which I molded Steph into my ideal plaything, enjoyed every one of her orifices bareback, and generally made a total pig of myself, was one of the highlights of my sexual life. Steph obeyed my every command, and cheerfully submitted to my every whim. The best part was, at the end of every day when we climbed into bed and my nut-sack was completely drained, Steph thanked me for the ongoing education.

"Is there anything I can do for you personally?" she asked me, on more than one occasion, as if the entire day spent on various sexual activities, hadn't benefited me, in any way.

"No, I am fine, Steph," I said, managing to keep a straight face. "I am happy to help you become a better lover."

Everything I had ever dreamed about doing to Steph, or in fact any woman on the planet, I got to experience in that fantastic week. On more than one occasion, I would enjoy an incredible ball-draining scenario, only to have the angelic teenager look at me, with her innocent face and ask.

"Can we try that one more time, to make sure I have it perfect?"

I fucked her in every position, anally and vaginally, availing ourselves of Suky's vast collection of lingerie, costumes and fetish wear. After Steph wore all of Suky's clothes, we raided the sex-shop, Amanda having given her blessing to my mission of molding Steph into a compliant fuck-toy. I think Amanda viewed an imminent increase in Steph's pricing structure, once the young blonde progressed beyond merely being a submissive in Amanda's sex show.

By the end of the week, I was running out of ideas, and unbelievably, out of desire, having fucked the compliant teenager completely out of my psyche. I was done with Steph, and I had the photos to prove it, having persuaded Steph to allow me to film most of our encounters, for educational purposes.

Steph had taken everything that I threw at her, no matter how perverse, with zero pushback. In fact, the only thing she complained about was the amount of times she was required to freshen up her makeup.

"You need to look your very best every time you approach a man," I explained to her. "This means that your hair and makeup needs to be impeccable."

In truth, I wanted her to look perfect for my ever-growing collection of home movies featuring her, but I never shared this with her. When Suky finally returned home, and I was tasked with unpacking her suitcases, I didn't even get erect at the sight of her lingerie, such was the extent to which Steph had emptied my nuts.

I thought I had got away with it too, especially after the first night, when Suky hit the sack early. In the morning, I found out that I was sorely mistaken. Suky, after noticing some irregularities in her closet, had a good look through my room, and after removing the air-conditioning vent covers, located my home-made movies of Steph.

Suky knew I feared her immensely, and as I knelt before her naked, she circled me holding her riding crop. She had whipped me with this particular instrument of torture in the past, and while the actual punishment was excruciatingly painful, the recovery period took weeks. I didn't want any part of the protracted healing process, and as she traced the tip of the crop across my trembling ass-cheeks, before moving it in a very threatening manner to the soles of my feet, I folded like a pack of cards.

"It was Amanda's idea," I said, knowing that Suky wouldn't confront her, at least head-on.

Suky moved around in front of me, placed the tip of the riding crop under my chin, and raised my eyes to meet hers.

"Amanda's?" she repeated, as I nodded my head in affirmation.

I wasn't sure if I had done the right thing initially, pitting two Alphas against each other. This could go horribly wrong for me, if the two of them got into a fight, particularly if Amanda prevailed.

I had seriously underestimated Suky, and the next day, when I got home from work, Amanda was kneeling naked in my office. She had her hands bound behind her back with a short piece of red rope, a glass butt-plug wedged deep inside her ass-hole, and she had been whipped, severely, judging by the marks on her back, ass, and shoulders.

Whatever fight had occurred between the two of them, Suky had won, and Amanda had been reduced to a compliant and fearful submissive. Suky was wearing a black corset, black panties and some black Louboutin high-heels. She still carried the riding crop, although in Amanda's beaten down state, this was superfluous. Fear alone would be sufficient to keep her obedient.

As Amanda knelt before her, Suky circled the frightened girl. It seemed incongruous, so out of character for Amanda to be so subdued, but Suky had broken her, and what remained was nothing for me to fear. Suky removed her black panties, and wadded them up in a ball.

"Open wide," she ordered, as Amanda willingly complied.

Suky forced her presumably wet panties into Amanda's mouth, effectively gagging the young girl. Then she tapped her riding crop on the top of my desk, and Amanda rose to her feet, and bent over the top of it. I didn't think Suky was going to thrash her any more. There really didn't seem to be much point in doing so, as Amanda was already broken, and there weren't many areas of her body that weren't already bruised and bloodied.

After Amanda bent over my desk, Suky retrieved a large strap-on phallus from the drawer of my desk, which I recognized immediately. It was the same instrument that Amanda had butt-fucked me with, the realistic fake ejaculating dildo with the huge nuts that hung beneath it, and acted as the reservoir for the imitation semen. There was an ominous click, as Suky secured the phallus into her harness, and then she untied Amanda's hands.

"Put your palms flat on the desk," Suky growled.

Amanda complied immediately, the fight having been thrashed from her body. Suky lined up the phallus with the entrance to Amanda's pussy, and in one fluid motion, impaled her with it. You see the term "revenge fuck" bandied about on the internet, but until you had witnessed Suky giving it to Amanda, you could never imagine quite what this could entail.

This was a protracted, brutal, non-merciful seeing-to, Suky seemingly intent on literally fucking the brains out of Amanda. Suky had a relentless pace going, the large latex phallus getting balls-deep on every inward stroke. Suky held the riding crop in one hand, occasionally bringing it to bear on Amanda's ass-cheeks, and a fistful of Amanda's long silky hair in the other, as she rode her submissive partner like a mule.

At first, Amanda took it like a champ, suffering in silence with her palms flat on my desk. However, as the indignity of her situation sank in, and maybe drawing some parallel between this and the abuse she suffered at the hands of her father and her mother's boyfriend, she began to weep uncontrollably. It was heartbreaking to watch, and I didn't have the stomach for it. However, I knew that if I didn't declare my allegiance without question, it would soon be my turn over the desk, and I didn't want that over-sized phallus in my anus.