My New Boss Pt. 14

When I came into the room, I inhaled sharply as I admired her beauty. Emma's silky dress was hiked up over her ass, revealing the fact that she was wearing a yellow garter belt to support her stockings. She had a pair of tiny yellow panties on, that were pulled down over her ass enough to allow me entry into her anal passage. I knew she was a virgin, anally, from both her sexual history disclosure and the physical examination she had endured from Amy. Emma had been unable to accommodate any but the tiniest of butt-plugs in her little asshole. This bitch was going to be tight.

Lisa had applied some Anal Ease lubricating jelly to Emma's asshole, and given the young girl two muscle relaxers. I tried to act cool as I scooted up behind her, but my heart was beating in my chest. She was just so fucking beautiful, way out of my league, and yet I was about to take her anal cherry from her. I smiled at her in the mirror, trying to break the ice.

Whatever fear or anxiety she was experiencing, as she was about to get butt-fucked for the first time, was hidden behind her beautiful smile and words of encouragement.

"Take me Daddy," she whispered, taking a page out of Lisa's book. "Fuck my tight virgin ass. My cherry is yours for the taking."

Her dirty talk was so in contrast to her angelic face, that I wanted to come immediately. I thought about jerking off on the back of her silk dress. It wouldn't have taken me long to blow my load all over her, such was my arousal. It was Lisa that brought my focus back to the reason we were here this afternoon.

"Let me lube you up Daddy," she offered. "Emma is ready for you to get balls-deep."

I struggled to control my urges, as Lisa applied a copious helping of Anal Ease to my throbbing cock. Once I was slick with the lubricating jelly, Lisa lined up my cock with the entrance to Emma's virgin rosebud, placed one hand on my ass, pushed me forward. I felt her sphincter push back against my cock-head and I let out a barely audible moan, as I anticipated being inside her.

Lisa pushed me forward with increased pressure, and I grabbed Emma's hips to hold her in position, but I wasn't able to penetrate the entrance to her anal passage.

"Fuck, she is too tight," I said quietly. "I can't get inside her."

To my surprise, it was Emma who offered me words of encouragement.

"Push harder, baby," she said with a smile. "I can handle it. I want you inside my ass."

Her innocent face staring back at me in the mirror, as she encouraged me to fuck her ass, was not helping me with my premature ejaculation issue. If she kept this up, I was going to come before I was inside her. Lisa recognized this and offered a solution.

"Let me warm her up for you," Lisa offered cheerfully. "I am prepared just in case this happened."

I stepped back from behind the young beauty, and watched as Lisa picked up a strap-on harness from the floor by the bed. She attached it to her lithe young frame and then selected a thin dildo from the collection assembled next to the bed. After lubing it up, Lisa got behind Emma, and positioned the greased head of the dildo against Emma's sphincter. I watched Emma's face intently, as Lisa forced herself inside the young blonde's asshole.

To her credit, Emma continued to hide her fear, discomfort, pain and whatever other emotions she was experiencing, behind a broad smile. Once Lisa was all the way inside Emma's anal passage, she withdrew completely, selected a slightly larger phallus, and repeated the process. After the fourth attachment had been deep inside Emma's ass, both girls agreed she was ready for me.

I took my place behind the young goddess, and lined myself up with her rosebud. I managed to penetrate her sphincter, the ring-shaped muscle relaxing as I entered it, and closing on my shaft once I was through it. The dildos had done a great job of opening up her anal passage sufficiently for me to gain entry, but she was still so incredibly tight that my range of motion was limited to fairly shallow strokes.

I maintained eye-contact with her in the mirror as I sodomized her, and she continued to hide any pain she was feeling behind her huge, agreeable smile. I am embarrassed to admit, I came shortly after getting inside her. She was just so pretty and so angelic looking that I couldn't hold myself back. The thought that I was balls-deep in Emma's virgin ass was just too much to handle, and I shot my load into her anal cavity.

Emma continued to talk dirty to me, the disparity between her angelic looks and the filth spewing from her mouth, emptying my nuts with every shallow thrust inside her. After I was finished ejaculating, I withdrew slowly from her tight asshole. Emma turned towards me and, under the watchful eye of Lisa, began to suck me clean.

"You don't need to," I began, before Lisa cut me off.

"Emma needs to learn everything that you like, baby," Lisa admonished me. "You can't cut her any slack just because she is so pretty. She is here for the sole purpose of pleasuring you. Bedsides, she used an anal cleanser before you fucked her ass, so she should be squeaky clean back there."

"I used it twice," Emma said proudly, as she sucked our fluids from my cock.

A very strange thing occurred after I came in Emma's ass. Instead of my cock softening, as it always did after ejaculation, my cock stayed rock-hard. I don't have a plausible explanation from a physiological standpoint, but my gut feeling is that Emma was just so impossibly cute, that my cock wanted another crack before she left. Whatever the reason, for the first time since I was in my early twenties, ten minutes after my orgasm, I was ready to go again.

Emma seemed very impressed with my refractory period, covering her mouth with one hand, a look of mock horror on her face as she expressed her surprise.

"Holy shit, Lisa," the young blonde squealed. "He is already hard again. You never told me about this."

In Lisa's defense, there was nothing to tell. I had fucked the crap out of Amy and Lisa on numerous occasions, and regardless of the level of stimulation they had provided me, we still had to wait in excess of thirty minutes for me to recharge and get hard again. This was uncharted territory for me. A young girl so breathtakingly gorgeous, that my cock stayed rock-hard out of fear of missing out. That was the truth of the matter. I wanted another piece of Emma in case I never saw her again.

I ended up tit-fucking her. It was the one position that I could think of, that would allow me to enjoy an orgasm and simultaneously stare at her beautiful face. Emma had done a wonderful job of sucking my cock clean, so I asked her to lay on her back and hold her tits together. I was so desperate to enjoy her for the second time, that my hand was shaking as I applied KY lube to my cock. She rested her manicured hand on my wrist to calm me.

"Lisa will lube us up, baby," she said sweetly. "There's no rush. You can enjoy me whenever you want. Take your time, baby."

Lisa did end up lubing both of us up. She poured a very generous helping of the silky lubricant on my shaft and cock-head first, before squeezing almost the whole bottle between Emma's tits. Of course, Emma's tits were perfect too, a full "C" cup with perky erect nipples that glistened once coated in the KY liquid.

As soon as I straddled her, and slipped my cock-head between her oiled tits, I felt my nuts constrict. Lisa moved away from lubing up Emma's tits, and positioned herself behind me. I heard some shuffling around as she maneuvered herself into her desired position.

I felt her warm breath on my buttocks first, followed shortly afterwards by her tongue. She traced the tip of it across my ass-cheeks, until it disappeared between them. When I felt her tongue on my asshole, I let out a little whimper, and Emma picked up on it right away.

"Don't hold back, baby," she cooed. "Come right away if it feels good. Most guys don't last that long with me."

Knowing that I wasn't alone in blowing my load quickly around her, made me feel like less of a chump. All guys find her completely irresistible, I told myself, justifying my early release. With the pressure to perform removed from my shoulders, I focused solely on my pleasure. I thrust deeply between her well-oiled tits, as she taunted me to orgasm, and Lisa licked my asshole. A few moments later I exploded, ejaculating all over Emma's face.

She continued to smile and maintain eye contact with me, even though my semen was now splattered all over her face and hair. I lowered my head to kiss her, something I had never been inclined to do with a woman whose face I had just come over. Emma and I made out for several moments, as Lisa continued to rim me.

I finally managed to pull myself away from this goddess, and she signaled her intent to take a shower.

"I will join you," Lisa said cheerfully.

I guess the toll of three intense orgasms, starting with Lisa's ninety minute blowjob on the return drive from the airport, got the best of me, because as the girls showered, I fell asleep. When I awoke, less then an hour later, Emma was gone and I already missed her.

Lisa and I had a couple of glasses of wine and rehashed the crazy evening. I had a visible erection, and as soon as Lisa saw it she offered to suck my cock. I politely declined. I knew that she was just going through the motions to secure her beloved Oxy, and I couldn't stop thinking about Emma. Once the alcohol kicked in, I excused myself, telling Lisa that I had some work to do in my office.

Lisa turned on the television, and I retired to my office with a stiff vodka. One thing led to another, and after a protracted viewing of Emma's impromptu photo shoot, emboldened by the alcohol, I called the young goddess. She didn't seem surprised at all to hear from me, answering the phone cheerfully.

"Hi Daddy, I knew you would call me. Did I pass the first audition?" she asked seductively. "I thought maybe you got bored of me because you fell asleep."

We ended up talking for two hours, although she was interrupted by her parents three times, whose general attentiveness seemed to remove daddy issues from the list of possibilities of why she had agreed to be my sex-toy for two hundred dollars. During our conversation, in which I laid my cards on the table, we openly discussed my sexual proclivities.

Emma got me very excited and when I told her so, we engaged in phone sex. Well, she remained fully clothed because her parents kept checking in on her, but she encouraged me to jerk off to my favorite photo of her, as she talked me over the edge.

After my cum-shot, we talked at length, about anything and everything. Emma proclaimed her innocence, telling me that tonight was the furthest she had ever been with a man. She told me that she had experienced a couple of joyless sexual encounters, but for the most part her sexual history was heavy petting. She had made a couple of remarks earlier that evening, that seemed to contradict her assertion that she was inexperienced, so I called her out on it.

At my request, Emma clarified her earlier remarks about the affect she had on men. She had said, "I am used to guys leaking in their undies" and "most guys don't last that long with me" which seemed to suggest sexual contact of some type. I didn't want to appear overly controlling or jealous, but I wanted this woman in my life and I needed the truth.

"That typically happened during a make-out session," she assured me with a giggle. "College guys normally, leaking in their undies as we kissed. A lot of times I would rub them through their jeans and get them to blow their wad in their pants," she confessed. "That was what I meant when I said most guys don't last that long with me, I swear."

She seemed genuine and I was inclined to believe her. However, her sexual disclosure also troubled me, and I asked her about it.

"I completely embellished it," she began, "to try and impress you. Lisa said you were a very experienced lover and I worried if you knew the truth about my limited sexual experience, you wouldn't consider me."

"Loves giving blowjobs?" I asked, the alcohol increasing my confidence.

"Never given one to completion," she assured me. "Foreplay only with my boyfriend."

"Tolerant of facials?"

"I got my first facial tonight, Daddy," she replied. "Now that I finally experienced one, I would change the word tolerant to enjoys."

When I pressed her for her true sexual history, I learned that Emma had only had sex twice in her life, both encounters she viewed as terrible. Her candid nature got me hard again, and as I pounded my last vodka, I told her that I had an erection.

"FaceTime me, baby," she teased. "My parents have gone to bed. I want to watch you jerk off again."

I couldn't get enough of this teenage goddess, and as soon we connected on FaceTime, Emma stripped down to her underwear and started to encourage me to jerk off. I have enjoyed phone sex and FaceTime sex numerous times before, and in the past I have always persuaded the woman to engage in the lewdest acts possible to get me off.

However, Emma was so beautiful, so innocent and angelic that I asked her just to pose for me in her bra and panties, and to look demure. She was wearing a pink Victoria's Secret push-up bra with matching thong panties, and had glossed her lips the exact same shade. She knelt in her bed holding a stuffed white teddy bear, and looking the picture of innocence. Her big blue eyes stared right into mine, and even though it was my fifth orgasm of the day, and I had consumed alcohol which should have inhibited my release, a few moments later I blew my load all over my stomach. Emma remained motionless after I ejaculated, allowing me to compose myself and also continuing to provide the visual of an angelic teenager.

"Can I see you tomorrow, Emma?" I asked, trying to hide my desperation, and sensing that the power dynamic between us was changing already.

"I have a Spanish immersion trip to Mexico for three days, starting tomorrow," she informed me. "I can cancel it if you need me to. I want to put your needs first, always."

I was tempted to ask her to cancel her trip, but central to my core was a deep-rooted respect for education. After all, I had allowed Lisa to suck me off for some cash to purchase her schoolbooks. I had released Amy from service as my sex-toy, to attend law school. I often encouraged my young girlfriends to maintain and respect their ties to their schools, by dressing up for me in their High School Cheerleader Uniforms. Yes, I should have been the President of my High School Booster Club, I mused.

Magnanimously, I agreed to allow Emma to attend her school trip. She thanked me profusely, a broad smile of gratitude plastered all over her beautiful face.

"I owe you one, Daddy," she said enthusiastically. "I want you to fuck me when I get back. Let's make a day of it."

"Ok, baby," I responded, "Enjoy your trip. I will see you as soon as you get back."

Emma blew me a kiss, her perfectly manicured nails matching her glossed lips exactly, as she held her dainty hand under her chin. I couldn't wait to see her again, and get balls-deep in that goddess.

Unfortunately for me, my plans to fuck the crap out of Emma never came to fruition, due to some unexpected and unwelcome changes. Three days is an eternity, and unfortunately the second event that broke up the love triangle between Amy, Lisa and I occurred in the 72 hour time period, that Emma was in Mexico. This event involve Tim, and it made me rue the day that I let a girl's education get in the way of my needs.

Just three days after Amy left to pursue her dreams of law school, our company expanded its footprint globally, opening a new office in Thailand. Tim petitioned for the position of President, in our new Bangkok office, and was given the opportunity. He left almost immediately, without even saying goodbye. I was promoted to President of our California office, based on the credit Tim had given me for our most recent successful marketing campaigns.

My new position gave me a twenty thousand dollar a month raise, and totally changed my financial situation. I didn't start firing people, the way Tim had. I wasn't looking to upset the apple cart, just trying to strive for incremental improvement.

Predictably, Suky showed up at my house, as she was now technically homeless. Going to Thailand with Tim was not an option, due to her immigration status. Not like he would have taken her anyway, with all the available pussy in the Land of Smiles. Tim didn't give Suky much notice, before he asked her to leave his house. He fucked her one last time, ejaculating inside her tight pussy as a parting gift for me, before he told her she had to go.

Suky didn't even ask me if she could stay with me. She still had a key, and most of her clothes were still in my master bedroom closet. Lisa and I were sitting at the breakfast table having lunch, when Suky let herself in the front door. She sauntered in like she owned the place and gave Lisa a filthy look. Lisa wisely averted her gaze, and then Suky grabbed me by my hair, and dragged me, half crawling, into the master bedroom.

Suky forced me onto my back on the bedroom floor, removed her panties and straddled my face. I knew what was expected of me, and, as I extended my tongue, I realized that Tim had just deposited a fresh load of semen inside my girlfriend's pussy.

"Tim says hi," Suky said coldly, as I ate his load from her. "Who is the bitch in the kitchen?"

"Just a friend that needs a place to crash Suky," I answered. "There is nothing going on between us, I swear on my life."

As I ate Suky to her first orgasm, Tim's load leaked from her pussy onto my face. After she ground out another three vocal orgasms on my face, I noticed she was still leaking profusely. That was either the most copious load Tim had ever blown inside her, or he had enjoyed her multiple times, before he booted her out of his place.

As Suky rested between orgasms, she seemed to anticipate my line of questioning and spoke up.

"Tim offered me up as a bonus to the Senior Management Team," she began, immediately answering my question about how Tim had possibly deposited so much semen inside of her. "He passed me around like a joint."

"In recognition of all their hard work over the last few months, and in anticipation that you might be a little less generous towards your co-workers when it comes to access to my body, Tim allowed the entire Marketing team a crack at my tight little pussy. Everyone except Jimmy, went for it," she said proudly, reveling in the fact that the only person in my department that didn't mount her, was openly gay.

"Those are my co-workers, Suky," I exclaimed jealously. "How the hell am I going to face them at work tomorrow?"

"You will figure it out," she taunted. "You could just pretend you know know nothing about it, and it will remain an office secret," she offered. "Or, you could take ownership of it, and explain it that was your idea."

"My idea," I said incredulously, "why the fuck would I allow all of my co-workers to fuck my girlfriend?"

"Teamwork? Bonding?" Suky began, as if she really thought that this would justify these lewd actions in some way.

"Tim," she continued, "if you are magnanimous about the gift you just bestowed upon your peers, it would go a long way towards building a cohesive team. Maybe offer up round two, if certain lofty performance goals are met?"

"What the hell, Suky? Round two?" I said with contempt.

"Well," she continued, "if you choose to sweep it under the rug, it won't go away. Your decision to ignore that it happened, will be viewed by many as an invitation to enjoy second helpings. Even those that don't go back for more will view you as a cuckold pussy."