My New Boss Pt. 32

My boss had just given his young Thai girlfriend the green-light to punish me, and had asked her what form the punishment would take.

"I want to fuck his ass with the strap-on," she said, with the same affected timidity that she had used to get me under the table, for the impromptu game of smile.

"This I want to see," my girlfriend chimed in excitedly.

I would have liked a bit more support from Suky, but she considered Tim the Alpha male in the group, and responded favorably to my subjugation. Ana put her harness back on, but opted for a longer black phallus, with which to penetrate me. While the new strap-on was longer, it was also much thinner, and had a distinct curve at the end. I didn't have much experience with anal sex toys, so the shape of this new one didn't raise any alarm bells for me. I was happy to see that she had applied a generous amount of lube to the end of it.

Tim returned to my comfortable recliner, and Suky refreshed his cocktail. Ana walked towards me, her large black strap-on looking very intimidating.

"Get on all fours, like the bitch you are," she commanded me.

I obeyed her instantly, terrified of getting my ass fucked, but desperately wanting to convey a message of obedience and respect, to the young girl. Once I was in the doggy-style position, Ana spoke.

"Face your boss," she said coldly.

I rotated one quarter of a turn, so that I was now looking directly at Tim. Suky had just returned with a fresh cocktail, and she placed it on the side table, next to my recliner. Then, still naked, she hopped on Tim's lap, gave him a tender open-mouthed kiss, and then turned to watch the show. Ana got behind me, and adjusted the hem of my babydoll so that the silk laid evenly across my ass-cheeks. I still had my yellow panties on, and wasn't sure if she planned to pull them to one side to enter me, or if she was going to rip them from me, in an overt show of dominance.

As I waited to get my punishment, my mind was awash with emotions. Fear was the principal one, as Ana had palpable contempt for me, and was now in the perfect position to make me squeal like a pig, as she tore my ass up. Shame was up there too, as I waited passively like a bitch, in the doggy-style position, with my yellow baby doll arranged neatly on my ass. Surprisingly, there was also a strong feeling of submission, as it aroused me to be taken like a dog, in front of my girlfriend and my boss. I just hoped it didn't hurt too much, and that Ana didn't try to injure me.

Ana picked up a pair of scissors and sliced through the rear of my g-string panties. The tiny yellow silk panties stayed on me, but Ana had created open access to my asshole. She placed the scissors on the floor and handed me the bottle of KY lubricant.

"Get yourself prepared for me," she barked.

I tried to lube my ass up, while remaining in the doggy-style position. However, it was quite difficult to do it that way, and my balance was compromised. Then I remembered that Suky was lubing her asshole up for fat John, the first time I laid eyes on her, so I adopted her position. I squatted on the balls of my feet, using my toes to balance me. Then I reached one hand around the back of my buttocks and began to apply a liberal dose of KY jelly to the entrance of my asshole.

As I hunched over like that, the babydoll reached the floor, covering any trace of my male genitalia. My yellow panties still caressed my nutsack, although there was no longer any fabric between my ass-cheeks. The yellow ribbon tied in my hair made me look less masculine also.

"He looks like a little girl masturbating," Suky exclaimed. "I want a picture of that."

"No pictures," I begged, my pleas falling on deaf ears, as my girlfriend snapped a few pictures of me, in the exact same pose that she had been when we first met.

Once I was sufficiently lubricated I got back on all fours. I was shaking as Ana sidled up behind me, and I felt the tip of the strap-on slide across my buttock. Ana arranged the hem of my babydoll so that it still covered my ass, but left her access to my anus. She lined the well-lubricated tip of the black phallus up with my sphincter, and eased herself forward.

To my surprise, there was no pain. Ana had evidently done this before, because she had selected a thinner strap-on, which was appropriate for a first timer, but had also used enough lube so that it pretty much slid inside me. She didn't really try and butt-fuck me, the way I had seen Suky dominate and brutally sodomize Lisa. Ana was much more particular about her position behind me, which had an obvious correlation to the position of the phallus, within my anal passage.

As she moved around behind me, it actually felt good. In a strange way, the way that being spanked is enjoyable if you have an erection. A few seconds later, as she brushed against my prostate, I tensed up at the profoundly pleasurable feelings emanating from within me.

"There it is," Ana said smugly, "I am going to make you blow your wad as I fuck your ass," she taunted.

Ana maneuvered herself into position, so that the tip of the strap-on touched my prostate with each gentle rocking motion of her hips. She wasn't really fucking me in the conventional sense, of thrusting inside of me. It was more a rotating movement, whereby she could ensure that the phallus was in constant contact with my prostate. This prostate stimulation was incredible and I felt my nuts start to constrict within a few moments.

"My bitch is close," she said to no-one in particular.

Shortly after she announced to the room that my orgasm was imminent, I involuntarily spurted all over the inside of my babydoll. Three huge ropes of semen hit my chest and stomach as I discharged a copious load from my balls. Ana continued with her soft prostate stimulation, and I leaked more seminal fluid into the silky babydoll as it hung below me.

My erection quickly diminished, and once I was flaccid, all my feelings of joy were replaced by humiliation and shame. I wanted to get the fuck out of there. I had semen drying on my chest, and my babydoll no longer resembled sexy feminine lingerie, stained as it was with my copious load.

Ana slapped my ass hard and called me a bitch. Then, as the pleasurable feelings evaporated, they were replaced by fear and pain, as Ana started a protracted and very brutal butt-fucking. She dispensed with the gentle hip rotations and started to fuck my ass with a vengeance. The black phallus felt huge now, as it was forced deeper into my anal passage, and I had some very real concerns of permanent injury.

Under virtually any other circumstances, I would have asked her to stop. However, my boss had made it crystal clear to me that if I didn't suck up whatever Ana dished out, my new work place was going to be Montreal. So, I bit my lip, and allowed her to savagely butt-fuck me.

Tim and Suky were watching intently, occasionally kissing as his erection returned. Suky was absentmindedly stroking his stomach just above his pubic area as he watched me getting sodomized.

"Have you learned your lesson, Timmy?" Ana finally asked me.

I nodded my head in affirmation, unable to form the words that she wanted to hear.

"Do you want me to stop?" she asked coldly.

"Please Ana," I begged, my voice shaky and wavering, "I have had enough."

Ana slowly withdrew her curved phallus, and I let out a sigh of relief. There was blood on the tip of the strap-on, and I wondered how badly my ass was bleeding. I remained on all fours, panting from the sustained anal invasion.

"Go and take a shower, you pussy," Ana said with contempt. "We still have to initiate you into a couple more of the bar games you have such an interest in."

As I was leaving the room, Suky hopped off of Tim's lap, knelt between his legs and started to suck his cock, presumably to get him ready for the next game.

I gave myself a good look over in the bathroom mirror, and my ass seemed fine. No pain when I felt around the entrance, and thankfully, no more blood. I took a quick shower, and when I emerged from the enclosure, Ana's mint green panties, that I had supposedly stolen, were on top of my bath towels. I had no fight left in me, so I put them on and returned to the living room.

Tim was sat at the dining table again, in the only available chair. He took one look at me, in Ana's panties, and chuckled.

"There she is," he said derisively, "my favorite cocksucker. Join the girls under the table."

I knelt down next to Tim and scooted under the table. Suky and Ana were already there, both naked except for their panties. Tim was naked with his legs spread wide apart. We listened as he outlined the rules of the next game.

This game was called "Guess who?" and it didn't take a genius to figure out why. Essentially, the three of us would take turns blowing Tim, while he tried to guess who was sucking his cock.

"I was forced to play this game in numerous VIP rooms in Bangkok, before Tim rescued me," Ana said, with a wavering voice. "It is much more humiliating when a guy that you have never met before selects you and three or four other bar hostesses to play."

We played a few rounds but Tim was able to recognize my superior oral skills every time I took his cock between my lips, and it quickly got boring. It was also apparent that my boss was well on the road to his next orgasm, so after about twenty minutes, Ana and Suky crawled out from under the table, and let me continue blowing Tim. I heard the two of them giggling and chatting excitedly as they left the room.

"I am ready to come, Timmy," my boss said after several minutes of squirming in his chair.

I switched to sustained frenulum teasing, knowing that this intense stimulation would make him blow his load quickly. A few moments later, as his nuts tightened, I enveloped the tip of his cock in my mouth, and swallowed his load. He moaned as he came, his ragged breathing an indicator of the pleasure he was feeling. Then his chair slid back and he was gone.

I remained under the table processing my combination of shame and arousal. Intellectually, my submission to my boss in exchange for a more favorable work environment, disgusted me. However, the physiological signs were in opposition to my disgust, as my cock was fully erect, and my breathing was labored from the excitement of being forced to suck my boss off. Even though it was Tim who had enjoyed the orgasm, I still had to compose myself before I crawled out from under the table. I didn't want the three of them to witness my arousal.

I heard the shower running and returned quickly to my room. To my dismay, Ana was there waiting for me, having apparently showered first.

"Tim wanted a little privacy in the shower with your girlfriend," she said cruelly, "Although since he just came in your mouth, I can't imagine what she can do for him. It's not quite your birthday yet, is it?" she continued, alluding to the fact that my boss planned to urinate on my girlfriend on my special day.

I didn't respond to her, although the sight and scent of her made my erection return.

"Did you enjoy your little game of guess who?" Ana asked. "Having the recipient of your oral skills be your boss, must add some added humiliation to the act. That is the first time I have ever played that game," she added. "Like I said, the only bar game I ever played in Bangkok was connect 4."

I didn't give Ana any reason to further punish me and I remained silent as she mocked and taunted me. I just had to get through this week.

"I need to lock you back in your cock-cage, before Tim gets out of the shower. The fun and games are done for a while and you need to be neutralized," she said dispassionately. "Get on all fours."

I instantly obeyed Ana, the threat of Montreal spurring me into action. Once I was on all fours, Ana placed the tip of her travel vibrator against my nuts, and switched it on. I was immediately subjected to a deep vibration in my balls, that wasn't particularly pleasurable.

My heart sank as I remembered the ruined orgasm that Suky had subjected me to, on the fateful night that I tried to orgasm twice. I never wanted to experience that pleasureless release again, but here I was, at the hands of my new tormentor, Ana.

"This won't take long," she assured me. "Trust me."

She was right. A few moments later, semen began to dribble out of the end of my cock, in a slow stream. The second Ana noticed my feeble ejaculation, she withdrew the vibrator from my nuts and my release ceased immediately. Ana allowed me a few seconds of rest before resting the vibrator back under my balls, thus repeating the cycle.

I am not sure if it was an orgasm or not, as it was not accompanied by any pleasure, or feeling of release. However, Ana did managed to completely drain my nuts and make my erection disappear. The last five minutes were the worst, as my seminal fluid stopped leaking from my cock-head, and the only sensation I had was an annoying humming in my nuts, as she held the vibrator tightly against them.

It wasn't painful, but it was very irritating and uncomfortable. Of course, I sucked it up, nodding my head in acknowledgment as Ana spoke.

"Ruined orgasm, my favorite!" she said cheerfully. "Are you ready to get back in your cage?"

It was a rhetorical question, so I didn't bother to answer.

"Kneel," Ana said, as I moved from my doggy-style position onto my knees.

Ana put the cock-cage on my flaccid penis, locked it with a satisfied smirk, and hung the key around her neck, so that it was visible to all in the house.

Beat it, Timmy," she said dismissively, and I made myself scarce, retreating to the relative safety of the RV, my new abode.

The RV did feel like a safe haven, although I knew it wasn't going to last long. The three of them were visible in the living room as I sat in the RV with all the lights off. Tim was drinking beer now, having apparently gotten quite intoxicated from slamming shots. I heard loud music start and then Tim, Ana and Suky started dancing. I tried to block them out, but I was so worried about their expectations from me that it was difficult to focus on anything else.

I did doze off later on the evening, and when I awoke they had apparently turned in for the night. The following day was my birthday, and for this reason, I tried to lay low. I had been dreading this day for months, and hoped that with the introduction of Ana into our little group, it would possibly pass without incident.

The first sign that things were not going to go according to my plan, was when I saw Suky flitting about in her cheerleader outfit. I let out a sigh of despair when I saw her all dressed up in pink, looking like a total fuck-toy. The inevitability of my upcoming defilement was made all the more certain when Tim emerged from the living room at eleven in the morning, with a beer in his hand.

He rarely drank alcohol in the day, and that would typically be a glass of wine with lunch, on the rare occasion that it happened. He gave me a sneer as he passed me, and my heart sank as I entered the living room and saw three empty beer cans at the foot of my recliner. I wanted to resist him, tell him to go fuck himself, but at sixty thousand dollars a month, I couldn't do anything that might remotely jeopardize my employment prospects.

I felt sick to my stomach as Suky appeared, pink silk ribbon tied in her long black pigtails, the familiar glitter sprinkled not only on her cheekbones, but also all over her fake eyelashes. She was wearing the light pink polyester and spandex crop-top, with the matching pleated skirt, that she had sucked me off in once. The Blow Job University cheerleader uniform, that was too short to ever be worn outside the house. As I took in the details, my cock stiffened immediately, before Suky shattered any illusions I had of her being available to me.

"Tim wants you in yellow," Suky informed me, referring to the silky babydoll that I had worn when we played smile. "Be in the shower in ten minutes."

I literally dragged myself into my bedroom, a sense of dread hanging over me. I racked my brain to see if there was any other option for me, but even as I tried to construe new scenarios, I dressed obediently, in his desired outfit. Once I had the yellow silk babydoll and the matching panties on, Ana entered my bedroom with some feminine accessories. This seemed superfluous to me, seeing as Tim was just going to take a piss on me, but Ana was insistent.

"Tim wants you to look cute," she informed me with a giggle, "and, more importantly, to look like you really made an effort."

Ten minutes later, as I knelt on the cold marble of the shower enclosure, nobody could have accused me of not trying to look cute. Ana did my makeup just so, a light yellow frosting on my lips, yellow glitter on my cheeks, a long silk yellow ribbon adorning my hair, and a yellow garter-belt with matching stockings, highlighting my femininity.

Suky joined me moments later, a picture of innocence in her pink cheerleader uniform. We knelt there uneasily, waiting for Tim to finish his final beer.

"He had six beers," Suky whispered quietly. "Celebrating your birthday," she added with a giggle.

Ana entered the bathroom next, a broad smile across her beautiful face, as she processed the image of Suky and I kneeling expectantly, waiting for her man. She leaned into the shower enclosure and extended her perfectly manicured hand. I shuddered as I noticed that she was holding the yellow bikini bottoms that I had stolen from her suitcase on the Below Deck boat.

"A parting gift from me, in case I never see you again," she said, as she hung the string bikini bottoms around my neck.

She had obviously just masturbated in them, as the crotch was visibly wet and her scent invaded my nose immediately, causing my cock to rise. I tried to will my erection away, the thought of being visibly excited as my boss pissed on me, wearing heavyily on me. However, Ana had so completely scented her bathing suit bottoms, that my erection grew, until I was totally hard.

I heard Tim enter the bathroom next, and then he peered around the shower enclosure, engrossed as he was with a seemingly important phone call.

"Book me on the 4 o'clock flight," he ordered someone. "My car will be here in ten minutes, and then Ana and I will be on our way. I just have a couple of recalcitrant employees to discipline, as my last official act."

I don't know who he was talking to, but if it was Human Resources, I wanted to grab the phone and explain to them that he wasn't writing us up, or docking our pay, for our perceived recalcitrance. He was about to urinate on us, which surely must violate some State or Federal employment laws. However, because Tim is a controlling asshole, he sensed my pushback, and handed me the phone.

"Did you want to have something documented in your personnel file?" he asked, much to Ana's amusement.

I lowered my head submissively, which had the unintended effect of forcing more of Ana's vaginal scent into my nostrils.

"Thanks again for the opportunity," my boss said with a sense of finality, before hanging up the phone.

Evidently pressed for time, with his transportation due in ten minutes, Tim Andrews unzipped his expensive tailored pants and extracted his large cock from his underwear.

"I hope you learn from this experience," he said condescendingly. "It has been a pleasure working with both of you."

Suky and I looked at each other quizzically, trying to understand his cryptic message, before Tim let go of his bladder and started to soak the two of us.

"Look at me," he ordered, "one last look at your boss."

If you have ever tried to drink six cans of beer without taking a piss, you would have realized that it is quite a challenge. Tim's bladder was completely full, and the stinky yellow fluid that emerged from the tip of his penis, came out under considerable pressure, giving the two of us a thorough hosing. He urinated for about thirty seconds, relishing his total domination of us, as Ana cheered him on.