My New Boss Pt. 14

My sexual escapades with the two young women went on for months. I was getting the most action I had ever enjoyed in my life. Lisa was available, twenty four hours a day, for whatever sexual depravity I could conjure up. On top of that, Amy and I fucked regularly, and we had the occasional threesome.

Amy and Lisa were both living with me. Suky still had most of her shit at my place, and maintained possession of the master bedroom, although she stayed every night at Tim's. Then, through a set of coincidences, our happy love triangle was completely upended.

Firstly, in a not entirely unexpected turn of events, Amy was accepted into Law School in another state. I knew she had been applying for admission over the last few months, and while the initial news was sad, after I digested it, I was happy for her to have an opportunity to potentially improve her life

She broke the news to me as soon as she received the acceptance letter, and it was with a heavy heart that we said our goodbyes. Amy told me that she was leaving the next day, and we sat down with Lisa to see where her head was at.

Lisa was high as a kite when we spoke to her, but she wasn't stupid. She knew that my sexual satisfaction was the key to her staying off the streets, as her options were very limited. She took too many recreational drugs to pass a pre-employment drug screen, had dropped out of school, and her parents had cut her off. I was a roof over her head, a steady supply of her much needed Oxy, and a relative safe haven, in a world that eats eighteen year old female drug-addicts up.

Lisa had obviously thought about her impending homelessness, because she presented a well thought-out plan for why I should keep her on as my fucktoy.

"I have a young girlfriend who is available whenever you want a threesome," Lisa began. "Emma is super cute, drug free, sexually naive but totally open to new experiences. I have a photo of her for you to check out."

Lisa handed me a photo of her and her Emma. "This was taken very recently, without any filters," she assured me.

Amy and I huddled to pore over the photo, as if we were choosing a new cast member for a reality show, based solely on the head-shot.

"Beautiful girl," Amy agreed, without any hint of jealousy. "Eighteen of course?"

"Just turned last month," Lisa assured me. "She will bring picture ID to her audition."

"Audition?" I repeated naively.

"You will definitely want to test drive this bitch," Amy said dispassionately. "A lot of young girls think that they are open to new experiences until they are faced with them," she added. "I think this girl needs to get baptized by fire!"

"She is down for anything that you desire, Tim," Lisa assured me, "anal, lesbian shows, golden showers. I didn't sugar coat it. I will make it happen, I promise. I know men don't communicate the same way women do. I know Amy interprets your desires and shares them with me. I will figure out exactly what you want from us, Tim, and we will provide it for you. Whatever it is," she added agreeably.

"Good girl," I said condescendingly, enjoying the complete power I had over this young beauty. "Just what I wanted to hear. A presentation like that is precisely why you made the debate team," I added dismissively.

"Get Emma here tonight," Amy said decisively. "Let's run that bitch through her paces before I leave tomorrow."

"Tonight?" I asked. "What if she has plans already?"

"What good is Emma to you, if she can't drop her plans at a moment's notice and be here to serve you?" Amy responded.

"I'll make the call," Lisa interjected. "What time works for you, Tim?"

Two hours later, Emma knelt naked before Amy and I, as we began the visual inspection. She was beautifully presented, presumably having been coached by Lisa that I like feminine women. Emma was clean shaven, having apparently just endured a Brazilian wax treatment. Her long blonde hair was like silk, as it cascaded down her back, and her makeup had been done professionally. Her pink lipgloss matched her perfectly manicured nails, and she had recently had a pedicure, which earned her some points. She was a spectacularly put together young woman, the perfect combination of natural beauty and the best cosmetic touches available to a young woman in LA.

"Good first impression," Amy conceded, as if we were judging a dog show.

As it turns out, we may have been trying to select "best in show" because Amy put the beautiful young Emma through a series of choreographed and intentionally demeaning moves. As I watched Emma splay herself, so that we could inspect her anus for any obvious signs of previous use, such as fissures or hemorrhoids, I wondered if Lisa had undergone this humiliating ritual.

"I put all prospective fuck-toys through this same thorough inspection process," Amy assured me, answering my question before I verbalized it. "It keeps them honest during the sexual history disclosure."

This disclosure, its purpose evident by its name, was very invasive and quite frankly embarrassing. However, Emma endured the humiliating questions, and we gleaned enough information to determine that she was an appropriate replacement for Amy. Emma enjoyed vaginal penetrative sex in any position, loved giving blowjobs, and was tolerant of facials. She had never experienced anal sex, but was willing to accommodate my desire for it. She was open to just about anything else, including golden showers, group sex, lesbian shows and even bukkake.

Amy did independently verify Emma's claim that she was a virgin, anally. Using a series of progressively larger butt-plugs, Amy probed Emma's anus until the young girl could take no more.

"We're good," Amy said dispassionately, as Emma recuperated from her violation. "No dicks have been inside that hole. It is too tight."

Once Emma was deemed to be physically and psychologically fit to be my plaything, the subject of monetary compensation came up.

"What are your fees, Emma," Amy asked the young girl.

"The same as Lisa," Emma responded quietly, as she knelt naked before us. "Two hundred dollars per session. No limits on your number of cumshots."

"Fair enough," I said, flashing Lisa an appreciative grin.

I had paid Lisa two hundred dollars to suck my cock the first time. Thereafter, I paid her in OxyContin, for which I paid fifty dollars per pill. Once I met with her dealer and agree to purchase one hundred pills at a time, my acquisition cost was reduced to twenty dollars per pill.

Thanks to Lisa's skillful manipulation, Emma was wiling to accommodate my every sexual need, for two hundred dollars per date. This was a deal, particularly because of how cute she was. I wanted to bust a nut, either inside or on Emma, but Amy indicated that we needed to get her tested for STIs, and enrolled on birth control before I used her.

"You shouldn't have to wear a condom, baby," Amy chided. "She will be ready for you to enjoy in seven days."

Emma agreed to go to the Doctor the following day, to get on birth control, and then we discussed her required maintenance, and upkeep expenses. Separate from her fee for sex, this money was paid to a young woman to reimburse her expenses incurred to look feminine. In Emma's case, I wanted her to be completely clean-shaven every time I saw her, nails freshly manicured, both fingernails and toenails, and her hair and makeup done professionally. We agreed on four hundred dollars per month as a reasonable compensation for Emma to be ready to go within two hours of my call, day or night.

Shortly after that discussion, Amy dismissed the young blonde, and she got up from her knees and scurried out of the room. I admired her naked form as she disappeared through the door, anticipating enjoying every inch of her lithe young body.

One of the reasons I was going to really miss Amy was that she was an exceptionally perceptive young woman. She knew that her invasive inspection of Emma had aroused me immensely, and moved in for the kill.

Amy, Lisa and I had one final threesome that night. There was a tinge of sadness as I realized this was probably the last time Any and I would fuck. However, as I visualized Emma kneeling naked before me, assuring me that I would be the very first man to sodomize her, I knew it was time to move on to new adventures.

To their credit, Lisa and Amy worked really hard to make our last night together memorable. They raided Suky's closet, and a broad smile appeared on my face as they emerged wearing nurse costumes. The attention to detail was phenomenal, short white silk skirts paired with silk bodices that showcased their pert boobs. They each had a red cross, the universal signal of the medical profession, on each breast. They were wearing white garter belts, with little red bows on the straps, and white patent leather ankle high boots, with the red cross symbol emblazoned on the front. Their nurse headpieces, were particularly feminine, a lace ruffle replacing the traditional starched hat that nurses typically wore. Atop the white lace was a red bow with white accents, to match the latex gloves they wore.

As they approached me I had to do a double take. They just looked so cute dressed identically.

"We need a semen sample," Lisa said seductively, before the two of them sank to their knees and began to unzip my pants.

I ended up coming three times that night, the first on their faces as the two sexy nurses sucked me off. I didn't take long to recover, thanks to the visual provided by the girls, as they shed their skirts and bodices, and cavorted before me in their garter belts and high heeled boots. I had my second orgasm doggy-style in Amy's asshole, as Lisa lay beneath us and sucked my nuts. We showered together after I withdrew from her anal passage, our bodies intertwined as we soaped each other up. At Lisa's insistence, I urinated on the two young women as they knelt in front of me and French kissed.

"Something to remember us by," she laughed, as she encouraged me to grab my iPhone and document the event.

Things were light between us, and the girls were laughing as I hosed them off. To my surprise, I got erect again, and for my final orgasm, I fucked Lisa in the ass, as Amy and I made out. It was the perfect end to our months long relationship, and while I was sad that it was coming to an end, I was grateful to the girls for getting me over my break up with Suky. I still loved that young Malaysian woman very much, but in my heart and soul I knew it was better for me to finally have that sadistic bitch in my rear view mirror.

After our farewell threesome, the three of us relaxed in the living room. I took care of my business with Emma, sending her four hundred dollars via Venmo.

I sent an accompanying text, "Good job today, girl. I am willing to try you out as soon as your birth control kicks in."

A few moments later she responded, "Thank you so much. I won't let you down Tim. I will be available in seven days, and I can't wait for you to take my anal cherry!"

Her comeback put a smile on my face. Emma was obviously being coached by Lisa, but it is one thing to understand a man's hot buttons, and another to stimulate them, so I gave her points for initiative.

Amy and Lisa slept in my bed that last night. I was in the middle, and the three of us spooned all night. The love was palpable and I woke up a couple of times wondering if I should try and persuade Amy to stay. I could have used her as a personal assistant, and would have been able to start her off at the same salary as a first year law school graduate. This would have saved her multiple years of hard work, plus the unavoidable mountain of debt created by law school.

We were up early the following day, and as I surveyed Amy from a distance, she looked happy. I just couldn't take her dreams of being a lawyer from her, and even though her dreams of convincing a jury were in direct conflict with my dreams of her being my fuck-toy, I relented and let her go, without any attempt to keep her as my own.

I took the morning off work to run Amy to the airport. Lisa rode with us, and the drive up there was over quickly, as the three of us reminisced over our fun months together. I had an erection for most of the drive, and as soon as we dropped Amy off, Lisa hopped in the front seat and unzipped my jeans.

As my new "main girl," she was entrusted with tending to my every need. She seemed to want to make a point that my trust was well-placed, because she ended up sucking my cock for an hour and a half on the ride home. As I have previously noted on more than one occasion, Lisa possesses otherworldly blowjob skills, and while she could have coaxed me to an orgasm within five minutes of leaving LAX, she was seemingly intent on getting me hooked on her, much the same way that I got her hooked on OxyContin.

For ninety minutes, she treated me to an equal parts sensational, and frustrating blowjob. Sensational in the sense that the entire time, it was all I could do to focus on driving. Frustrating in the sense that, I came close to orgasm so many times that my nuts truly ached.

"Lisa, please," I begged, on more than one occasion.

"You are driving, baby," she admonished me. "Either wait until we get home, or I can stop sucking your cock, if you prefer."

"Don't stop," I pleaded, through gritted teeth. "Please, don't stop!"

Lisa teased and edged me right up until we pulled into my driveway. When I entered my garage, she looked up at me with her extraordinary green eyes, and smiled sweetly.

"Good job, baby," she teased. "I didn't want you to have an accident on the drive home, but now we are here, bust a nut if you want. Unless you want to wait until Emma comes over later," she teased.

I knew she was fucking with me. There was no way I could wait a few more hours to have my release, so I put my hand on the top of her head, grabbed a fistful of her red hair, and applied a little downward pressure.

"Somebody has made their choice," she said with a smile, as she lowered her lips on to my blood-engorged cock.

I didn't take long to come in her mouth. Lisa gives the best blowjobs I have ever experienced, and as she bobbed her head up and down on my cock, using the perfect combination of suction, saliva and frenulum stimulation, I erupted with a roar. I thought I was going to black out, such was the intensity of my release. I saw stars and struggled with tunnel vision for several seconds. I was grateful to the young girl for letting me park up, before she finally got me off.

Lisa had apparently swallowed my load because she snuggled up close to me, nibbled my ear and let out a giggle.

"See you inside, baby," she teased, as she got out of my car and headed inside to freshen up.

I sat in my car for several minutes, taking the time to compose myself and reflect on my good fortune. I had lost Amy today, but Lisa was going to be a more than capable replacement. Plus I had the innocent Emma coming over later. Life was good!

Later that afternoon I took a shower, and prepared myself for my evening with Emma. She showed up right on time, looking every bit like she had spent her entire monthly grooming budget on getting ready for this evening. She looked radiant, dressed in a very classy silk dress, that was a beautiful shade of yellow. Her nails and hair bow were the exact shade of the dress, as were her stockings and high-heels. She had glossed her lips a pale shade of yellow, frosted on top with a white glitter.

As she stood there demurely in my hallway, her angelic face belying her true reason for being here, I felt my cock throb in my jeans. I was going to take this young girl's anal cherry, for the princely sum of two hundred dollars.

"May I take a photo you?" I asked politely. "You look exquisite."

I ended up taking several pictures of Emma as she posed playfully in my hallway. After we were done with our impromptu photo shoot, I sent Emma my favorite picture of her, with an accompanying text.

"Use this as your head-shot when trying to drum up new business," I suggested. "You look angelic."

The businessman in me wanted to add that she could double, maybe triple her prices, but I quickly remembered that this ran counter to my interests, and didn't add that sage advice. I was only paying two hundred dollars per date, regardless of how many shots on goal I enjoyed. In the real world, Emma could have commanded six hundred dollars per hour, which was the going rate for a model-quality teen, that offered anal sex.

Emma, in her current state of preparation, was model-quality. She possessed a natural beauty, her blue eyes absolutely stunning, especially when viewed through her light blonde bangs, that framed her angelic, symmetrical face. A professional makeup artist had attended to her eyes, lips and cheekbones, accentuating the most positive attributes of each of her gorgeous features. She looked like a model on the cover of a teen magazine, and I was about to fuck her in the ass.

Even though I wanted to come right away in Emma's virgin anal passage, I also wanted to experience her other delights, and so I told Lisa I wanted to start with a two-girl blowjob.

"Don't make me come too quickly, Lisa," I admonished the young world-class cocksucker. "This is foreplay, before the main event."

"Whatever you want, Daddy," which became Lisa's default response, sent a shiver down my spine each time she uttered it.

The two girls moved towards me, in tandem, their desire to please me written all over their young faces. Lisa and Emma took turns kissing me, while Lisa unzipped and lowered my jeans to my ankles. I was tenting in my briefs and had a visible wet spot.

"He always leaks," Lisa teased, much to my embarrassment.

"I am used to guys leaking in their undies," Emma responded confidently, "I have that affect on men."

The two young women seemed to share a moment, united in their ability to turn men weak at the knees, and render them unable to fully control their body functions. Their focus turned back to me seconds later, as they sank to their knees in unison. Lisa extended her tongue first, making contact with the tip of my cock through my underwear.

"He likes that," she said, her first, of many, direct instructions to Emma.

Lisa continued to mentor Emma, showing her exactly what I liked as they ran through a series of choreographed sex acts. I had been very clear with Lisa that I didn't want them to make me come, prior to my anal invasion of Emma. However, they took me close a couple of times, and I had to reset in order to prevent my premature ejaculation.

As I watched Emma obediently follow Lisa's instructions, I was at a loss for why she had such a fervent desire to please me. Amy traded sex for favors, whether it was a place to live, or help with her rent. Lisa traded sex for OxyContin, and would have done whatever I wanted, as long as there was a little pill for her at the end of it. Emma's desire to please me was much harder to figure out. She was a teenage goddess who could have been a model. She came from a nice family, lived in a clean middle class home, and hadn't had that many sexual experiences with guys.

Yet, whatever sexual act I suggested was met with an eager, agreeable affirmation, and an almost instantaneous move to adopt the next position. In addition, I was only paying her two hundred dollars a day. Surely, she shouldn't have been so accommodating for that amount of money.

When it came time for the main event, I was beside myself with lust. I think Emma was the most beautiful girl I had ever been with, although from a chemistry standpoint, it was Suky that rocked my world the hardest. That said, Emma was exquisite. Lisa positioned her on all fours on my bed, with a large mirror resting against my headboard, so that I could watch her face as I entered her asshole.