My New Boss Pt. 28

I knew the Captain had been on the boat for the last eight weeks. He may have jerked off during that time, but he hadn't had any real intimacy, and I was going to offer him some play in exchange for my freedom.

The Captain leaned over me and put his stethoscope on my chest. He told me to breathe in deeply, and listened to my long exhale. He tried to remain professional, but I witnessed him inhale deeply through his nose, to take in my scent. I knew he didn't have much medical training, but was just going to call a Doctor for diagnosis. I had to make a move before he made that call, because I was definitely going to receive a clean bill of health. The Captain had one hand on the chest-piece of the stethoscope, and his other hand on his right ear-piece. He was stood in front of me, leaning over me, his legs spread wide apart to maintain his balance.

I looked up at him, as innocently as I could, then extended one of my freshly painted fingertips to his crotch. He jumped when I made contact with him, but as I located his cock, and gave it a squeeze, it twitched in my hand. It was all or nothing now, so I reached out my other hand and started to unzip his dress whites. He didn't make any attempt to stop me, but simply uttered my name, quietly under his breath.

"Samantha," he whispered.

"Captain," I responded, seductively. "I have wanted to suck your cock since I first met you."

His cock responded favorably to my touch and verbal stimulation, and I felt it continue to stiffen in my hands. He looked over his shoulder a couple of times, but we were in a locked, windowless room and he was the senior ranking officer on board, currently off-shift.

"No-one is going to bother us," I assured him, "unless there is an emergency."

Once his zipper was undone, I scooted towards him, still on my knees. I kept my legs apart, so that my skirt remained hiked up, and my garter-belt was visible. I nibbled his cock through his white linen pants, leaving traces of light pink lipstick on his crotch.

"I will launder your pants for you, Captain, and iron them perfectly when we are done," I said submissively, offering myself up as his surrogate wife while I was on board, rather than just a piece of ass. "Don't worry about the mess we make," I added with a giggle.

I felt his cock throb in his pants as I offered myself to him. Even though the stewardesses were young and reasonably attractive, the sheer number of hours they had to work, coupled with the lack of interaction with members of the opposite sex, meant that there was little incentive to worry about their femininity. They kept themselves clean, but short hair was the easiest to maintain, short unpainted nails required the least maintenance, and comfortable baggy clothes were the normal off-duty attire. Most of the crew didn't even wear perfume.

As I knelt before him, heavily scented, with my lips glossed and my nails painted, it occurred to me that I might have been the most feminine person he had been around in many weeks. The Captain kept looking down at my garter-belt, fixated as he was by the titillating glimpse of the pink silk straps. I hiked my skirt up further for his visual pleasure and resumed my gentle nibbling of his cock, through his dress whites. Occasionally, I would look up at him and smile, and pretty soon he was done with my medical examination, and focused solely on his release.

He was breathing heavily now, moaning as I teased him. I guess he was twenty years older than me, although in my current predicament, he could have been eighty years old and I would have offered him the same loving treatment. As the tell-tale wet patch of arousal appeared in the front of his linen pants, I released his cock from the confines of his underwear. Pre-cum pooled around the tip of his swollen cock, and it felt warm to the touch. I leaned forward, extended my tongue, and licked his seminal fluids from his cock-head. He was leaking heavily now, and I wondered how long it had been since his last release.

I let his semen coat my lips, and looked up shyly at him as he continued to admire me.

"How would you like to have your first orgasm, Captain," I asked innocently, as if to suggest there were many more opportunities available to him, should he wish to enjoy me as his long-term concubine.

"Blowjob," he muttered shakily, as he struggled to control his breathing.

"Whatever you desire, Captain," I said cheerfully, as I took his cock-head between my soft eager lips.

As soon as he entered my mouth I started to tease him with my free hand. Instinctively, I reached my other hand to cup his ass, but the handcuffs rattled against the railings, prevent me from giving him any further pleasure. The Captain realized that he was missing out and, breaking protocol, released me from the steel bracelet.

My time with Lisa, had taught me a thing or two about blowjobs. She was without doubt the best cocksucker I had ever encountered, at the tender age of eighteen. She imparted all of her tricks to me before she left, and now the honorable Captain was about to be the lucky recipient of Lisa's, should have been trademarked blowjob, albeit administered by my eager lips. I had to get this right, I had to rock this man's world, if I had any chance of clemency.

I could have got him off so quickly, as it was apparent it had been a while for the old man. However, he could have achieved the same result by jerking off, or by enlisting the services of the many young escorts, that were available at every port of call. This had to be different. This had to be memorable. I had to leave him wanting more, willing to save my ass from ejection from the boat, in exchange for regular lip service from me. It was an exchange I was totally willing to make, I just need him on board.

For this reason, I took my time. I worshipped his cock, nuts and taint, giving him an extended edging session and a loving tongue bath. Every time he got close, I changed up the stimulation, and I could tell by his contorted facial expressions, and his squirming and moans of delight, that he was in heaven. A couple of times, when I took him right to the edge, he begged me for release.

"Please Samantha," he pleaded, "I am ready to come."

I looked up at him with adoration in my eyes, trying to convey that I was in no hurry. He could enjoy me for as long as he wanted. Take his sweet ass time before he busted a nut. I made him beg me three times before I asked him directly.

"Are you ready to come, Captain?" I asked.

"Jesus, Samantha, Yes," he replied.

"Do you want to come in my mouth or on my face?" I asked coquettishly. "I will swallow your load if you want," I added suggestively.

"I am close, Samantha," he grunted, as I gave his nuts a playful squeeze.

A few seconds later, his desire got the best of him. He began to thrust his hips forward, as if making love to my mouth. Sensing no resistance, he grabbed my ears and started to fuck my face, in earnest. I became quite vocal, moaning and signaling my arousal, as this powerful man took what was rightfully his.

One of my hands was cupped under his swollen nuts, kneading them to encourage him to unload their contents. I slipped my other hand between his legs and began to tease his taint. When I gauged his reaction, it became apparent to me that the Captain, like most men of his generation, had never experienced any stimulation of his nether regions. Rimjobs, prostate stimulation, and anal-play in general, were the foreplay of the younger generation, and prior to this moment, the Captain had not been exposed to this otherworldly delight.

He let out a moan of pleasure, and uttered under his breath.

"Jesus Christ, Samantha, that feels incredible. Please don't stop."

I couldn't move my head due to the Captain's vice grip on my ears, so I raised my eyes to look up at him. I had never given myself more willingly to any man, than I was at this moment. I wanted him to know that, so I smiled broadly, to assure him of my total availability.

The Captain got my message loud and clear, grunting his understanding of the possibilities that lay ahead for him, if he released me from my imprisonment.

"I am coming, Samantha," he cried out, as he unloaded his nuts into my eager mouth.

Lisa had taught me that if a guy is fucking your face, the best course of action is to remain passive, and let him control the flow. Purse your lips, she had instructed me, and keep the saliva flowing. So, blessed to have the advice of one the world's best cocksuckers, I did as instructed, and let the Captain fuck my face until he was done unloading his nuts. I swallowed every last drop of his load, not wanting to break a single promise I ever made to this man.

He released my ears, withdrew his cock from my mouth, and slumped to his knees. I opened my mouth, to let him see that I had eaten his load, and then, smiling broadly at him, I spoke.

"Thank you, Captain," I said softly, with as much deference as I could.

He was breathing heavily and panting. I reached for the stethoscope and held it up jokingly.

"Are you having heart palpitations, Captain?" I asked with a practiced innocence.

"Holy Christ, Samantha," he exclaimed through ragged breaths, "where on earth did you learn to do that?"

"It is a work in progress," I said suggestively, "hopefully you will work with me, and teach me how to make it perfect for you, each and every time."

The old man sat down, leaned his back against the railings that I had been handcuffed to, and continued to try and compose himself. His cock was poking out from his zipper, still erect and covered with traces of my light pink lipstick.

"Let me clean you up, Captain," I said cheerfully, as if this man's pleasure was my life's goal.

I was kneeling in front of him, so I lowered my head into his lap, and began to tenderly lick his cock clean. After a few moments, encouraged by the fact that his erection didn't go away, I extended my legs behind me, so that I was lying prone on the floor. I ground my hips into the floor and scooted back slightly, which had the effect of hiking my little skirt higher up my slender thighs, revealing my garter-belt straps, and the feminine pink bows that adorned them.

I couldn't see what the Captain was doing, as I had my face buried in his lap, but he let out another moan of pleasure, so I hoped he was responding to the visual stimulation, as well as the physical. After several minutes of my eager lips on his cock, it was clear that I had averted its softening, and he was ready for round two. I sat up next to him and slowly removed his dress whites and his underwear.

"Can you get up on your knees, Sir?" I asked the old man.

He nodded an affirmation, and was kneeling shortly afterwards. I crouched in front of him, taking the tip of his cock back into my mouth, and I heard him moan again. Once I was sure he was fully erect, I rolled over onto my back, slipped under him and started to nibble his nutsack. At the same time, I reached one of my hands to his cock, adjusted its position so that my light pink nails were clearly visible, and started to jerk him off. He let out a little whimper of pleasure and I made a mental note that he enjoyed this very much.

I raised the backs of my knees from the floor and put the soles of my bare feet flat on the tiles of the engine room floor. This also had the effect of hiking my skirt up my thighs. The Captain was captivated by my pink garter-belt, and let out another appreciative moan. I felt his nuts constrict, and I knew he was close. Apparently, the imbalance of power between us emboldened him to focus on his own pleasure, and not give a fuck about mine. This was perfect, as I needed this man to view me as his very own sex-toy.

"I am close, Samantha," he whispered hoarsely.

"Come when you are ready, Captain," I said seductively, as I scooted further back under his crotch, and kissed his taint.

Judging by his reaction, the old man had never experienced someone's tongue on his undercarriage. He stiffened up immediately and was whimpering as I simultaneously jerked him off and kissed his taint. It took me by surprise how quickly the second cumshot erupted, and the volume of semen was astonishing too, seeing as how this old man had recently enjoyed an orgasm.

The first blast landed on my upper thighs, right at the top of thigh-highs. I jumped at the feeling of his jizz splattering on my leg. The second rope of semen landed on the front of my skirt, rendering it unwearable for the rest of the day. I gave his taint a quick nibble as the rest of his load dribbled down his cock, onto my chin.

"Oh my God," the Captain exclaimed joyfully, "I came so hard!"

I emerged from underneath his nutsack, all smiles, desperate for my freedom.

"I hope you enjoyed that as much as I did Sir," I said seductively, "Let me clean you up."

While my extended clean-up session didn't coax another erection from him, his moans and whimpers were a clear indication that he loved my attentions. I had noticed during my confinement in the engine room, that there was a sink and a general clean up area in the room. I excused myself and cleaned up using some hand wipes and the soap. Once I was clean, I removed my soiled skirt, and let my t-shirt hang loose around me.

The stretch cotton t-shirt was designed to be tucked into the skirt, so was longer than a regular t-shirt. In fact, when I caught a reflection of myself in the mirror finish of the engine boiler, it appeared as if I were wearing a tight, very short, minidress. I didn't have any panties on, but I had tucked my penis into the waist band of the garter-belt, the base of which was now visible, in addition to the straps.

I made a big show of pulling the hem of my stretch t-shirt down, mimicking the bimbos I had seen pulling their too-short mini-dresses down in nightclubs, years ago when I used to frequent them.

"Oh Captain," I said with affected modesty, "my dress is way to short to wear without panties."

The Captain blushed at my remark and I could see the wanton lust in his eyes. I grabbed a few hand-wipes, and sashayed towards him, trying to be as overtly feminine as I could. He had risen from his knees now, gathered his composure and was leaning against the railings, that I had been handcuffed to. His flaccid cock hung from beneath his dress white shirt, and as I approached him in my make-shift mini dress, I noticed it twitch at the sight of me.

When I reached him, I sank to my knees, in a clear display of submission.

"Let me clean you up, Captain," I offered.

I gave his cock, balls, taint and asshole a thorough wipe down before giving his cock a little peck, right on the tip. He looked down at me, and for the first time since I had met him, gave me a loving tender smile.

"Dress me like you dressed your boss in the video," he said, although it was more like a plea, than a directive.

I knew he had responded favorably to that video. Ana had presented it as evidence that my sexual encounter with Tim, was consensual. My complete submission to my boss was documented, as I held his underwear for him to step into, then his pants, before the video culminated in me kissing his cock through his shorts, after he was dressed.

The Captain had evidently enjoyed that piece of evidence, and wanted a repeat performance for himself. If there was one thing I had learned working for Tim Andrews it was submission. So, utilizing this skill to manipulate the Captain, I dressed him in a tantalizingly slow manner, kissing, licking, nibbling and sucking every square inch of his exposed skin as I helped him get his clothes on. I remained on my knees once he was dressed, silent and with extreme deference.

I wasn't going to ask for release from my imprisonment, as it felt too much like quid pro quo. However, as I knelt there demurely before him in my cotton mini-dress and my pink garter-belt, I could see the desire in his eyes, and I was not surprised when he reached for his radio.

"Captain to Bosun, do you copy?"

"Copy Captain," came the immediate reply.

"I am releasing the prisoner, based on new evidence that I have just been presented with," he began. "He is free to roam the ship with the other guests."

"Copy that Captain, prisoner is free until further notice," the Bosun responded.

With that the Captain gathered his belongings and started to leave the room.

"Sir," I said hesitantly.

"Yes, Samantha," he responded tenderly, clearly enamored with me.

"Sir, can I spend tonight in the safety of your cabin?" I said with trepidation. "I won't be a nuisance and I can sleep on the floor if you need to be alone," I offered. "Tim is not going to be happy that I have been released from confinement. If I could stay out of his way, until you make your final decision about my destiny, I would be eternally grateful to you."

I had chosen my words carefully. As the Captain processed quite what my eternal gratitude entailed, I saw his cock twitch in his dress whites, and I knew I had him.

"You may spend the night with me, under my protection, Samantha," he said magnanimously. "Grab your skirt, honey, and let's go to bed."

The Captain escorted me to his cabin, which was adjacent to the Bridge, and I was pleasantly surprised by its opulence. It closely resembled the master suite that Tim was shown, when he first boarded the ship. Nothing like the cramped staff quarters, below deck. There was a King Size bed in one corner of the large suite, a bar with two bar stools, a desk with a large leather chair, a love-seat and a mini kitchen.

I had been in his situation before, and I just wanted to make it easy for him. I didn't want him to have to jump through hoops for my affection, so I made it very obvious that I was available for all of his wants and desires, as long as he continued to protect me, from forced debarkation.

For this reason, I bent down to look at his CD collection. Once I was on my knees, it was very easy to get on all fours, under the guise of reading the CD titles. I looked back at him over my shoulder, fully aware that my makeshift mini-dress had ridden up over my ass-cheeks, and said seductively.

"What are you in the mood for, Sir?"

I couldn't have telegraphed my availability any more clearly, and as I watched him adjust his crotch, I knew he wanted a piece of my ass.

"I am going to take a shower first," he said in a measured tone. "Fix me a cocktail, Samantha, vodka on the rocks."

I liked his take-charge attitude, and made his drink as he left to shower. A few moments after I heard the shower running, I went into his bedroom, grabbed a pair of his running shorts and after putting them on, I joined him in the shower.

I realized I looked a lot less feminine in my new attire, but he wasn't going to be seeing much of me, in our next encounter. The Captain had a look of surprise as I joined him in the shower, but I motioned for him to turn away from me, and began to lather up his back. He was cleaning his chest and stomach, as I knelt behind him and soaped his ass-cheeks. I made sure he was squeaky clean back there, running my soapy hand between his buttocks several times. After a quick rinse, I spread his butt-cheeks apart, extended my tongue, and began to lick his buttocks softly, like a kitten.

He let out a moan, both to signal to me to continue and to express his gratitude for my continued attention to him. I really wanted to make this special for him. We were going to dock at Alexandria Port in less than twelve hours. How the Captain felt about me, would shape the rest of my life. I knew Egyptian prisons were brutal places, that the establishment viewed homosexual acts, particular sodomy, as blasphemous. Even if I got found not guilty of the charges, as a white man with no grasp of the language or culture, I would face a hostile crowd in the dormitory style cells, particularly dressed in the uniform of a stewardess.