My New Boss Pt. 13

To my complete surprise, Lisa was a world-class cocksucker, by far the best I have ever experienced, which is saying a lot, considering the amount of prostitutes I have enjoyed over the years. It was the perfect combination of edging, deep-throating and sensual teasing, and she brought me to the boil several times. Each time, as I rapidly approached my orgasm, she would change up her technique and prevent me from premature ejaculation.

"I am close," I whispered through gritted teeth, on more than one occasion.

"I know," she responded cheerfully, withdrawing her lips from my cock as she let me compose myself.

"Lisa, please," I begged after several minutes of her edging me.

"Are you enjoying my blowjob?" she teased, at one point, clearly loving the control she had over me.

"Yes," I whispered, "but I want to come."

"You think you want to come," she corrected me. "However, as soon as you blow your wad, you will wish it hadn't ended. Take your time baby, enjoy my eager touch. We have forty minutes, let's not rush."

As I absorbed her words of wisdom, she adjusted the position of her head and began to give me a mind blowing frenulum tease, that in itself could have got me off in a couple of minutes, had she been inclined to rush me. I felt my nuts constrict, the sure sign that I was close, and Lisa moved her attentions back to a less sensitive area of my genitals, thereby averting my imminent ejaculation.

To say I got my money's worth was an understatement. Had I been given the opportunity to preview her oral skills, I would have paid five hundred dollars for that blowjob.

I had lost track of time. I knew Amy had indicated that she would be gone about forty minutes, but never in my wildest dreams did I anticipate that we would use most of our allotted time, on such an extended, sensual blowjob. Lisa however, in-spite of all of her faults, was focused on the value for money component of my blowjob, and she decided when my time was up.

She patted the edge of the bed and motioned for me to sit. I followed her directive, and she spread my knees far apart, and knelt between them. She looked up at me one more time, smiled and said, very sweetly.

"Now, I am ready for you to come. I really enjoyed sucking your cock, but now I want to swallow your load."

I was breathing heavily from the prolonged teasing session, I could feel sweat under my armpits and behind my neck, and my nuts ached from the anticipation of an orgasm. However, once Lisa decreed that it was time, she put her lips back on me, and using an incredible combination of suction, saliva, frenulum stimulation and an ever increasing tempo, she extracted the entire contents of my swollen nuts in less than sixty seconds.

It was a truly mind-blowing orgasm, up there with the most memorable of my life. By far the best blowjob I had ever experienced, timed almost to perfection, as I heard my garage door open right after I blew my copious load into Lisa's mouth. I was grateful for the fact that she had seated me on the bed, before getting me off, as my whole body convulsed at the magic moment. I am not sure I could have remained standing through that experience, and Lisa knew that.

After I stopped ejaculating, Lisa looked up at me with her innocent green eyes, opened her mouth and allowed me the privilege of watching her swallow my load.

"My God," I exclaimed, "that was amazing. I did not expect that."

"No-one has ever asked for their money back," she said with a smile, in an obvious attempt at humor.

She licked her lips and whispered, "There is plenty more where that came from. Lots of extras on my menu for a generous guy like you."

I heard Amy enter my living room and call out Lisa's name. Before I could thank her, beg her for her phone number, or tell her that I loved her, Lisa was gone, in search of her beloved Oxy, desperately chasing her high.

Lisa spent a lot of time at my house after that first sexual encounter. It was a very convenient quid pro quo arrangement, with both parties getting exactly what we wanted. I was a safe haven for Lisa, in addition to being clean and respectful towards her. I was single, had a little cash to throw around, and I am not embarrassed to admit it, I was an easy come.

Lisa was able to give up her regulars, a bunch of married guys that she met through babysitting. I say give up her regulars as if she dropped them overnight, but, in truth it was a protracted separation, one-sided to say the least. She had to change her phone number such was the volume of calls from these middle-aged under-sexed losers, trying to persuade her not to disappear from their lives. One of them offered her one thousand dollars for one last night, money he could ill afford to spend, she assured me. It was at this point that I realized that her comment about no-one ever asking for their money back, wasn't a poor attempt at humor. This young girl was a hooker!

We talked about it one night, and Lisa was very candid.

"Married guys create extra drama for me," she began. "Besides the obvious marital chaos created if we get caught by the wife, there is the extra hassle of trying to hide my drug dependence from the kids, and the potential of introducing an STI into an otherwise happy household."

She had obviously given this a lot of thought, and she wanted to run her process by me.

"Why would I want to entertain half a dozen married guys to get my fix, when I could be exclusive with you?" she mused. "Keep me supplied with Oxy, and I will move in and be yours," she offered. "For whatever you desire."

Amy, surprisingly enough, was all for it. She had applied for admission to several law schools, many of which were out of state, and probably felt like she could garner my future financial support, if she hooked me up with some replacement pussy.

I knew it was wrong, but once I figured out the extent of Lisa's drug addiction, I used it to my advantage. I asked Amy to introduce me to her dealer, and after I had bought Oxy a few times, I negotiated a larger purchase at a greatly reduced price. I also persuaded the drug dealer not to sell Oxy to Lisa or Amy in the future, so that I alone controlled the young redhead's supply.

Lisa was my sexual plaything in exchange for OxyContin. I was paying her in drugs by now, instead of cash, and I figured my reduced acquisition cost of the Oxy, increased my return on my dollar.

I was paying about one third of the street price, as long as I purchased one hundred pills each time. I kept a stash of Oxy in my wall safe, and dangled it in front of the young redhead, in exchange for increasingly depraved sex acts.

I wasn't assertive enough or communicative enough to ask Lisa directly for the aforementioned kinky sex acts, so Amy took care of the logistics. I would tell her exactly what I was in the mood for, and she would act as an intermediary between Lisa and I, to ensure that I got exactly what I wanted, however perverse.

Amy still lived in my house and shared my bed, but it was Lisa who kept my balls drained. Lisa started to attend school more sporadically a few weeks after she first sucked me off, as her drug dependence affected her cognitive ability, and made it harder for her to keep pace with the coursework. I did contact her school on her behalf, after she designated me as her parental guardian. They allowed her to study off-campus, and turn her assignments in online. Truth be told, I ended up doing most of her coursework, but it was enough to keep her enrolled. Her focus shifted from getting an education to finding a safe place to live, where she could continue her drug abuse. For this reason, one day she practically begged me to let her stay with me.

I had already made the decision to allow her to live at my place, but I held my cards close to my chest, and listened impassively as she knelt before me and outlined her case to be my roommate. She made quite a compelling presentation, her debate skills presumably honed by her time on the Varsity team. She offered me unrestricted access to all three of her orifices, several costume changes per day, and a completely open mind to new experiences.

I felt like such a prick when I magnanimously allowed her to suck me off, to facilitate my decision to let her reside in my house, albeit under a probationary period.

"You need to be on your best behavior, Lisa," I told her as she knelt before me with my semen on her lips. "Do whatever Daddy tells you. Be a good girl."

"Whatever you want, Daddy," she repeated agreeably.

Once our agreement was ironed out, I gradually increased Lisa's dose of Oxy, and threatened to withhold it from her, unless she did exactly what I wanted sexually. As it happens, the mere threat was enough. Lisa soon found out that her dealer had zero interest in selling to her, and realized that I was now her sole source of Oxy. Sure, there were other dealers, operating in the shady parts of town, but these were places that a teenage girl could not go alone, and Lisa adjusted quickly to her new reality.

Once her dependence on me was solidified, my sexual demands became increasingly perverse. Lisa had agreeably accommodated all of my kinks, so I began to unleash my previously buried sexual proclivities. Buried that is, due to their unsavory nature or the fact that they could be considered taboo, in some conservative settings.

I wasn't there when Amy ran my latest requests by Lisa, but I got the feedback later each evening, and there was a remarkable consistency to it. Amy would present the perverse scenario, and Lisa would absorb, process and nod her assent to the act, all within a few seconds. I am sure Lisa only questioned whether the sex act would be more painful than the symptoms of OxyContin withdrawal, which from all accounts were horrible. Lisa never said no!

Amy offered Lisa up to me for all kinds of sexual delights, but once I had enjoyed her dressed up as she was in her rather limited wardrobe, I decided to expand my horizons. Lisa and Amy were forbidden to enter the master bedroom, reserved as it was for Suky, and her extensive closet of lingerie, costumes and fetish wear. However, one afternoon, when I craved variety, l let the girls in there.

Thirty minutes later, as Amy emerged dressed as a dominatrix, dragging Lisa behind her on a dog leash, my decision to share Suky's clothes was validated. The two of them were definitely in sync as far providing me a visual spectacle, and I watched in awe as Amy dominated the young redhead.

Amy was dressed from head to toe in skintight black latex, but it was her high-heeled stiletto boots, shined as they were to perfection, that caught my focus. I knew Suky hadn't polished them herself, and I also knew that I had to return them to her closet in perfect condition, after Lisa had worn them.

Amy strutted around my living room keeping the young girl on a very short leash, and my cock stiffened as I watched Lisa's complete submission. At one point, Amy stood still in the center of the room, as Lisa knelt just behind her, in the 'heel' position. This gave me the opportunity to check out what Lisa was wearing.

My eyes were drawn to her kitten ears first, the cute black furry little accessory, setting the tone for her depiction as an animal. Lisa was wearing a black satin bodysuit, black stockings and black satin slippers, almost like ballet shoes. This choice of footwear, in addition to being very feminine, enabled Lisa to crawl on all fours, without the added hindrance of heels. She had some padded gloves on her hands, presumably to protect her palms, in case her master wanted to walk her on a hard surface.

Amy tugged hard once on the leash, pulling Lisa up from her knees and onto all fours. Without using any verbal commands, Amy walked briskly forward, dragging Lisa behind her. As they passed me I couldn't resist checking out Lisa's tight little ass. A smile came over my face as the coup de grace came into view. Lisa had a cute, black furry kitten tail emerging from her asshole, the perfect accessory to complete her costume.

Lisa looked so cute dressed up as a little kitten, her tail swishing from side to side as Amy walked her on the leash. I wanted to fuck Lisa, and I was just about to verbalize my desires to Amy, when she cut me off.

"I am sure you are ready to bust a nut, Tim!" she began, stating the obvious. "However, we have a little show planned for you first. Relax and enjoy!"

Amy led Lisa over to the coffee table in my living room, bent her over it so that her ass was raised up in the air, and tied her off on a short leash. I watched as Amy put on a harness, and then attached a strap-on dildo to it. She removed Lisa's kitten tail, which had been wedged inside her asshole, and had done a phenomenal job of opening her up. She started to apply some Anal Ease jelly to Lisa's gaping asshole, and shortly thereafter entered the little minx.

Amy gave Lisa an extended ass-fucking, during which the young redhead experienced several orgasms. I was surprised at how easily Lisa came from anal sex, although I suspect some of her sexual release was due to being thoroughly dominated. Several minutes later, Amy withdrew her dildo from Lisa's ass, moved around to her head, and made her suck the phallus clean. My cock throbbed as I watched Amy own the young redhead, and I started to unzip my jeans.

"Are you ready to get yours?" Amy teased. " I have another surprise for you."

Amy withdrew the strap-on from Lisa's mouth and left to go into the kitchen. Seconds later she returned with a stainless steel bowl. It had some paw prints stenciled on it, was full of milk and had Lisa emblazoned on the side of it. I watched in amusement as Amy placed the bowl in the middle of the living room floor, and asked Lisa if she was hungry.

Lisa nodded an affirmative, and after being untied from the leg of the coffee table, crawled over to the bowl and began to lick its contents up, using her tongue. Amy walked over to my side, finished unzipping my jeans, and removed my stiffening cock.

"I think Lisa might need some more cream in her bowl," she suggested.

It took me a split second to process what she was saying, and a smile crept over my face as got her drift. I could butt-fuck this young girl whenever I desired, but this was an opportunity to try something new, and I was all over it. I began to touch myself, as Amy snuggled closer to me and started to talk dirty to me.

"Why don't you go and kneel by Lisa," she invited me. "Let her suck your cock until you are close. Then jerk off in her bowl, baby. Add your load to her creamy meal. Watch that bitch lap it up."

This sounded like a great idea, so I walked over to Lisa and lowered myself to my knees so that she could suck my cock. I hadn't even been between Lisa's lips for five minutes, before I felt my nuts constrict, such are her blowjob skills. She bobbed her head up and down my shaft, using the perfect amount of suction, and allowing her tongue to tease my frenulum as she blew me. She even knew when I was close, bringing me right to the edge, before withdrawing my cock from her mouth, and then pointing it directly into her bowl of milk.

My first rope of cum landed with a splash in the middle of the milk, resting on the surface of it, like whipped cream atop a specialty coffee. Lisa continued to jerk me off and I blew three more ropes into her bowl. Once she was sure I was done ejaculating, she lowered my cock into the liquid, and stirred it, which dissolve my semen into the milk, making it much more appetizing for the young redhead.

"Eat," I said commandingly.

Lisa licked her lips and lowered them to the bowl, eagerly lapping up my load as it mixed with her milk. I watched her intently as she licked the bowl clean, and then Amy called her to heel, and they left the room as they entered it, master and pet.

After my experience with Lisa dressed as a kitten, the girls were given free reign over Suky's closet. I still had the occasional threesome with Amy and Lisa, but for the most part, Amy and I would chat about what sexual kink I wanted Lisa to do next. Then Amy would raid Suky's extensive closet full of lingerie, costumes and fetish wear, and serve the young redhead up to me on a platter, dressed in some ridiculously sexy costume. As Lisa got more and more reliant on the drugs, she would beg me to let her suck me off in exchange for a hit of Oxy.

My morning routine definitely got upgraded. Amy and I shared a bed although she had to get up earlier than I did. Amy would get out of my bed before I awoke, and as she got ready for school, Lisa would crawl under my comforter and suck my cock until I woke up.

The first time it happened, I was in the middle of a very sensual dream about her. In my dream, Lisa was on her knees dressed as a cheerleader. She had put her hair in pigtails using two pink bows. She had applied her pink lip gloss and was alternating between sucking my cock and gently nibbling my nuts. She maintained eye contact as she pleasured me and I was getting close. I started to thrust my hips slightly and she allowed me to gently make love to her soft pink lips. We both knew that I was close and she smiled at me to let me know that I could come in her warm mouth. Once I got her consent, I started to thrust deeper between her glossed lips, trying to bust a nut in her mouth.

I awoke right at the point of ejaculatory inevitably. Well, that is the medical term. All men know it as "the point of no return". The point when orgasm is a certainty even if the stimulation ceases immediately. I was in bed and she was kneeling on the floor by the side of my my bed. Her head was under the comforter, and she had my cock between her lips. I was humping the sheets, grinding my hips in desperate search of release. Right as I awoke I ejaculated into Lisa's mouth, spurting six or seven thick ropes of cum as I unloaded my swollen nuts.

It was a spectacular way to start my day, and from that day forward, it was our new routine. Each morning Lisa would slip her head under the comforter, and awaken me with a blowjob. Getting sucked off is a marvelous way to wake up, and I would kick the covers off and watch the teenage redhead work her magic. She truly was an expert at oral sex, and most of the time, I just relaxed in my bed and let her coax a load from my nuts. Once I came in her mouth, she would let me watch her swallow my load, with a look of eternal gratitude on her young face.

Some mornings I just wasn't ready to get up. I would still be sleepy as she sucked my cock to wake me up. On these occasions, I would roll onto my side, and fuck Lisa's mouth until I came inside it. Then I would withdraw my cock from between her soft lips, roll over and go back to sleep.

Lisa's reward for getting me off was a hit of Oxy, and she always craved her first hit of the day. So, on the mornings when I blew my load and fell back to sleep, she would come back about thirty minutes later and suck me off again.

After I came, and as I composed myself, Lisa would kneel expectantly by my bedside, awaiting her first hit of Oxy. I would place the pill in the palm of my hand, and allow her to take it from me, without using her hands.

The next part of my daily routine was my morning shower. Sometimes Lisa would join me, and I would fuck her vaginally or anally against the wall of the shower enclosure. However, most days I showered alone, and I used this time to prepare myself mentally for the day. If I had a particularly stressful day ahead, I was usually ready for another round. I would communicate my desired way to have my next orgasm to Amy, and she would relay my expectations to the young redhead.

"This morning," I told Amy, "I want to jerk off in Lisa's hair."

"No problem Tim," Amy said cheerfully. "I will tell Lisa to get her hair and makeup really cute for you."