My New Boss Pt. 13

As soon as Tim told the girls to get rid of me, my iPad went black, as Rim terminated the streaming of me fucking my pocket pussy. It was an abrupt ending to my forced masturbation session, and while part of me felt relieved, my excitement was fueled by the thought of what my boss was going to do with the entire massage team at his disposal. There were six twenty-something young Asians and the Mamasan, Joy. How the hell could one man handle that much stimulation?

I resumed fucking my pocket pussy as I contemplated my boss' session with the girls. I knew I would hear all about it in excruciating detail, tomorrow at work, but for now it was just what my imagination could conjure up. I exploded into my sex toy a few moments later, my eyes closed, thinking about my girlfriend taking a facial from my boss.

After I came, shame washed over me, as I took in the visual of my plastic sex-toy stuffed into my sofa, encased in a pair of scented silky panties. It seemed so demeaning, especially while my boss had seven women at his disposal. My cock went soft and I withdrew from the pocket pussy, the combination of the lube and my semen smeared all over the front of my silky panties. Rim's final slur, "Pussy," was an accurate and fitting pejorative.

Suky never came home that night. She moved on to bigger and better things, as she spent the night with Tim. I knew that my boss had enjoyed the fuck out of my girlfriend, and would tell me all of the sordid details, the next day at work. Even though I had been forced to watch Fat John enjoy Suky, I had never been cuckolded by someone that I had to see everyday. The thought of it, prior to it happening, disgusted me. However, now that I was actually living it, it made my cock rock-hard, just to think about it. Every time I closed my eyes, I could visualize Suky kneeling before my boss, smiling up at him, with his semen splattered all over her face. This sensation was tinged with jealousy, and a hint of sadness, but my cock stayed erect all evening.

When Amy returned home that night from her after-school study group, she asked me where Suky was. I could barely verbalize the events of the evening, so traumatizing were they to me. However, as I stammered through my recollection of what had transpired, my cock continued to stay rock-hard.

Amy obviously noticed my mixture of distress and arousal, because sensing an opportunity, she moved in for the kill. When I turned in for the night, the beautiful young college girl was in my bed, dressed in her new pink lingerie. She smelled so good, was dressed so sexily, and made herself so available to me, I just could not resist her, even though I had already come twice that evening.

"I am available to you, for whatever needs you may have," she teased. "I want nothing in return, your desire for me is sufficient. Just tell me how you want me."

"Doggy-style," I stammered, remembering the first time I had taken her over my desk.

Amy didn't need any foreplay, intimacy or further direction. She got up on the bed on all fours, arched her back so that her blonde hair spilled over her pink silk camisole, and wiggled her ass seductively. I went to lower her panties, but she looked over her shoulder and informed me.

"I am wearing crotchless panties, baby. I will only ever wear this style of underwear when I am around you. I want to make it easy for you to get inside me, whenever you feel in the mood."

I ended up easing into Amy's tight, young pussy, from behind, through the access hole in her panties. The silk felt fantastic as it caressed both sides of my cock, while we fucked doggy-style. Her assurance that she wanted nothing in return, conspired with her submissive stance, and the gentle caress of her silky panties, to get me off. As I approached my orgasm, Amy issued her next request.

"Pull out of me when you are ready to blow your load," she pleaded. "I want you to ejaculate all over my new lingerie. Mark me as your bitch."

This was all the invitation that I needed, and as I approached my cumshot, I told Amy I was close. She raised her head upright and arched her back, and as I enjoyed the visual of the young blonde submitting to me, I withdrew at the last second, and erupted all over her lower back, encased as it was in her new pink camisole. Even though I had come twice earlier that evening, performing for the massage parlor girls, my first rope of come was very powerful, ascending in a high arc before splattering across her beautiful lingerie and the tips of her long blonde hair.

Amy let out a squeal of delight, and raised her ass before thrusting it back into me. This enabled me to ease my cock between the gap in her ass cheeks, and as I gyrated my hips forward, this additional friction made me shoot my second rope right into her silky tresses. The semen got absorbed right away, her hair matting around it as it dried. I had two less powerful cumshots onto her ass, before the sensitivity in my cock-head forced me to pull back from her.

"Holy fuck, baby, you soaked me," she exclaimed cheerfully. "You came hard!"

I slumped down onto the bed, testing the waters to see if Amy really didn't need anything in return from me. Amy seemed enthralled with my orgasm, and laid down next to me, stroking my forehead with her fingernails.

"Just relax, baby," she assured me, as she gently caressed the temples of my head.

This was a first for me. Being able to blow my wad and then fall asleep was uncharted territory for me. Amy laid next to me touching me very gently as I closed my eyes. She was whispering sweet nothings to me, as I slowly drifted off. I don't know how long she allowed me to rest, but at some point I awoke to her soft lips on my cock.

I was laying on my side, and Amy had maneuvered herself into position so that her head was in my crotch. She raked her fingernails across my buttocks as she blew me, and before long I had another erection.

"I want you to come again," she said, smiling at me like my pleasure was the most important thing in her world.

Amy helped me up to my knees, and continued to suck my cock until I was completely hard. As I knelt before her on the bed, she put her manicured fingertips under her arms and removed her soiled camisole. It was at this moment that I realized her nails were the exact same shade as her lingerie. Seconds later I noticed that her glossed lips were also the same shade. Amy had clearly put some effort into the visual component of my experience.

Once her camisole was off, her pert breasts were right in front of me, standing upright, nipples fully erect. Amy lifted one of my legs up, and crawled underneath me so that I was straddling her upper body. She gave me the sweetest most innocent smile, before she offered herself up to me for my next release.

"Do you want to fuck my tits, baby?" she asked. "Bust a nut before we go to bed."

This was a new experience for me. Not the tit-fucking of course, but rather the overt offer of sexual release, with seemingly no reciprocation required, on my part. From a girl that I wasn't paying to date, but was actually more like my girlfriend.

"Come on baby," Amy cooed, as she held her tits together and licked one of her nipples. "Don't make me beg you."

I shuffled nervously on my knees as I looked down at her. My cock stiffened under her verbal provocation, and I leaked a drop of pre-cum onto her stomach.

"There's the response I was looking for," Amy said, as she picked up the KY liquid and poured a generous helping of lubricant between her tits.

Once her tits were glistening with the lubricant, she held them together and thrust them skyward, inviting me to fuck them. I shuffled forward on my knees and slid my cock between her well-oiled breasts. It felt really good to slide into that little cavity that was created by Amy squeezing her tits together, and I let out a whimper of excitement. Once my cock was nestled between them, I thrust forward tentatively, pleasure written all over my face.

"Don't be shy," Amy admonished me, "Fuck my tits, baby."

I did start to thrust between them, although apparently not aggressively enough for Amy's liking. She put one hand on my ass and pulled me deeper between her lubricated mounds, not pausing until my cock-head hit her chin. Once I made contact with her face, I backed up reflexively, and Amy pulled me back between her tits, until we established a rhythm.

She was smiling at me the whole time I tit-fucked her, a seemingly open invitation to come between her breasts. Her baby blue eyes twinkled as she accommodated my primal urges, and as I got into a steady flow, she began to tease me.

"Fuck my tits baby. Own them. Own me. I want you to come on my face."

I let out another whimper, and Amy knew I was close. She lifted her head slightly, and began to kiss the tip of my cock as it emerged from between her breasts. I noticed traces of her pink lipgloss all over my cock-head, and moments later I blew my wad. My first cumshot hit her right on the lips, nestled as they were around the tip of my cock.

The gentleman in me pulled back reflexively, trying to redirect my ejaculation onto her tits or neck. Amy was having none of it. She tightened her grip on my ass and pulled me forward abruptly, opening her mouth wide to accommodate my thrusting cock. I shot my second rope of cum into her mouth, gasping at the sensations as she closed her lips around me, and began to suckle me. She took the next two shots in her mouth before releasing me and throwing her head backwards.

This movement made me shoot my last rope onto her neck, where it swiftly ran down into her hair. She kept her breasts squeezed firmly together allowing me to grind out the last of my orgasm. I was breathing hard by the time she released my cock from between her tits, and began to suck me clean.

She encouraged me to roll over on my side, as she extricated herself from beneath me and got to her feet by the bedside. She kissed me gently on the lips and spoke.

"I am going to take a shower," she said quietly, "Don't wait up for me."

I tried my hardest to stay awake until she returned, but the physical release had taken its toll, and I ended up falling asleep. I never heard her come back to bed, but in the morning I awoke to the sensations of her sucking me off. Apparently, it never bothered Amy that I had used her the night before, and I ended up blowing my load, as I laid on my side and fucked her mouth.

Amy was the exact opposite of Suky, when it came to sex. With Suky, it was all about her needs. She would straddle my face, get herself off, and then fall asleep. Amy, however, didn't seem that interested in getting off. She viewed sex as a currency, to be used in exchange for something she wanted, or needed. Amy used sex to get me to pay her late rent, even though she squandered the money on lingerie. Amy used sex to negotiate free room and board in my house. In her mind, everything had a price, and, after Suky dropped out of my life, Amy became my love interest.

I still saw Suky once a week at the massage parlor, although I wasn't a willing participant. Tim, because he is a controlling asshole, insisted that I keep my Saturday morning appointment with Suky. Tim would use Suky for an hour and a half, and then turn her over to me in a disgusting state. She would often have semen on her clothes and in her hair, and one day I questioned her about it.

"Does Tim even get you naked at the massage parlor?" I asked, knowing that he had access to all three of her orifices whenever he desired.

"Yes," Suky delighted in telling me. "Tim enjoys me as he sees fit every Saturday morning. After he is satisfied, he likes me to get dressed. Then he jerks off on me, before sending me to your appointment."

Suky got off on their domination of me. She would make me kiss her, and eat her pussy and asshole out, so that I could taste his semen in every one of her orifices. Of course, Tim forbade Suky to give me any attention, becoming extremely possessive of his latest fuck-toy.

If Tim hadn't held my career in his hands, I would have told Suky to fuck off. Especially, as Amy was taking care of all of my needs, sexually. Tim had made it crystal clear to me that if I didn't obey Suky's commands with a smile, I was going to spend my weekends pampering and worshiping Fat John.

On the home front, Amy was more than enough woman for me, and she kept my nuts completely drained. One night, Amy gave me a blowjob, and after I came in her mouth, we were snuggling. I was basking in my post-orgasmic bliss, and Amy asked me an interesting question.

"Baby, would you be interested in helping out a friend of mine, who is in a spot of trouble?" she asked. "Lisa, who is a college freshman, and a member of my debate team, spent the money her parents sent her for books, on drugs. She is full of remorse, desperately in need of school books, and needs to earn some quick cash. I thought you might be willing to help her out," Amy said.

I wasn't sure what Amy was getting at, but I was willing to help out her friend, if she needed school books. Before I could say yes, Amy showed me a picture of Lisa, in her High School Cheerleader Uniform, which seemed unnecessary.

"She's very cute," Amy said, stating the obvious.

Lisa was eighteen years old, a green-eyed redhead, and as her athletic uniform hid little from the eyes, evidently a total hardbody.

"How much money does Lisa need for her school books?" I asked Amy.

"Two hundred," Amy responded. "Lisa is willing to suck you off for two hundred dollars."

"Suck me off?" I repeated, reflexively looking at her Cheerleader picture, but feeling like an asshole the second I did.

"Of course, baby. I wouldn't ask you to help her out for free," Amy said to my surprise. "It's for a good cause. I know you value education."

"Are you okay with this Amy?" I asked. "I don't want to do anything to hurt our relationship."

"Of course," Amy replied. "I want you to be totally satisfied, sexually. I know men crave variety, and I know I need to pay my rent. Consider Lisa this month's payment."

Amy brought Lisa over to my house, the following night. I thought it was going to be awkward, but Lisa was high as a kite, and very eager to earn her two hundred dollars. I offered Amy and Lisa a glass of wine, and the three of us sat in the living room and chatted amiably.

"Can we take care of the money side of our transaction?" Lisa asked, me less than ten minutes after she arrived. "I want to score some more drugs."

"Of course Lisa," Amy said pleasantly. "Tim, why don't you and Lisa go and get acquainted. I will go and get some Oxy for Lisa, and give you guys some privacy. Can I get the two hundred dollars up front, Tim?"

"I thought the money was for school books," I said naively.

Lisa and Amy looked at each other and began to giggle.

"I didn't think you would let me suck your cock for drug money," the young redhead responded. "I lied about needing schoolbooks. I need Oxy. Please, I have nowhere else to turn."

I knew, deep in my soul, that this was wrong, but you shouldn't judge me until you have been in my position. I had a very cute eighteen year old co-ed, who was offering to suck me off, for two hundred bucks. I had neckties worth more than that. Why should I care what she spent the money on, I rationalized?

"Come on Tim," Amy teased, "let her suck you off, baby."

"Guys tell me I am really good at blowjobs," Lisa said innocently. "I swallow too, unless you would rather come on my face," she added enthusiastically.

Lisa's matter of fact approach to sex for money, made my cock stiffen in my pants. She was of legal age, I reminded myself, as if to further justify my decision. Before I knew it, my little head had acted on behalf of the rest of my body, and I nodded in agreement. Lisa broke out into a broad smile as I handed Amy two hundred dollars.

The young redhead grabbed me by the hand, and asked me where the master bedroom was. Instinctively, I pointed at the door, and Lisa started to lead me in that direction.

"Amy, can we use your bedroom?" I asked, after remembering that most of Suky's stuff was still in the master bedroom.

"Of course, no problem," Amy responded as she left to score the Oxy. "See you in about forty minutes."

My cock was already rock-hard by the time we entered Amy's bedroom. I was very excited at the prospect of getting head from this young girl, although my expectations were fairly low. I knew there was no such thing as a bad blowjob, although at eighteen years old, I was sure Lisa would be mediocre at best. Apparently some guys had told her she was good at blowjobs, but I doubt any of her teenage recipients had much to compare it to.

Lisa moved in close to me and tried to kiss me. I really wanted to make out with the young redhead, but I am not a complete idiot, so I asked her for some ID just to make sure she was of legal age. At forty-two years of age, I could do some serious prison time, if Lisa wasn't at least eighteen. She seemed a little taken aback, but a quick glance at her driver license proved that she was legal, having turned eighteen two months ago.

Once I knew she was legal, Lisa and I started to make out. She was a very sensual kisser, and my cock throbbed in my pants as we shared a tender open-mouthed kiss. She was also aggressive, rubbing my my cock through my jeans as we made out. Lisa had my zipper undone within a few moments, and she reminded me of Amy as she tried to undress me as we embraced. Maybe it is a generational thing, but we were moving much faster than I was used to.

A couple of minutes after we entered the room, my jeans and my shirt were on the floor, and I was stood there in just my briefs, with nowhere to hide my erection. I had leaked into my underwear too, a visible wet stain announcing to the young woman that I was an easy come.

Lisa seemed flattered by my excitement, and rubbed the tip of my cock through my briefs, leaving traces of pre-cum on the palm of her hand.

"How do you want me?" she asked amiably.

When I didn't respond immediately, she smiled and rephrased the question.

"Do you want to stand and I will get on my knees? Do you want to sit on the bed while I kneel in front of you? How do you want me?" Lisa asked cheerfully.

I wanted the bitch on her knees, naked except for her high heels, as I stood in front of the mirror and watched her blow me. However, because I am neither assertive or particularly communicative, when it comes to sex, I clammed up and shuffled around uncomfortably.

"Ladies choice then," she said sweetly, diffusing any awkwardness that would have existed, had she not been so comfortable in her position.

Lisa dropped slowly to her knees, and looked up at me adoringly, her green eyes sparkling as she licked her lips. Then she extended her tongue and licked the wet spot in my briefs. I jumped involuntarily at her touch, and for a split second it felt like I was the teenager.

"You like a soft touch?" she asked, as if she was trying to tailor this experience to my preferences.

"I do prefer soft and gentle," I confessed, getting more comfortable with this young girl with each passing moment.

Lisa nodded her understanding and began to nibble and lick my cock through my underwear. Her ministrations made me desire her very much, and also served to increase the size of the wet spot in my briefs. She teased me until my underwear was slick with my seminal fluids, before making a big show of removing them with her teeth. Once my briefs hit the floor, she sucked and nibbled my nuts for several minutes, until I was whimpering with a combination of frustration and anticipation.

My pre-cum was flowing freely, and the teenage redhead stopped fucking with me periodically, to lick the fluids from my cock-head. Finally, after what seemed like an eternity, she enveloped my cock in her warm mouth and began to suck me off.