• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Transformed

Transformed

123

I was led through into Mr Sharad's office. This job was going to utterly transform my life! I'd be able to pay off my debts and start on the mortgage. My car wouldn't get repossessed, and I wouldn't get myself blacklisted. Everything was riding on this job. I'd not even applied for it, but had been picked seemingly at random from a lowly button-puncher to be the boss's new PA. Why me? I don't actually know. Apparently my files had been reviewed, and I had all the skills I'd need.

Mr Sharad's executive secretary sat me down and sashayed away, hips swinging enticingly. She strode elegantly around her desk and sat down, quickly getting to work on her computer.

I was left waiting. And waiting. The secretary basically ignored me, and I was left twiddling my thumbs.

Eventually, in response to some unseen signal, she looked up at me.

"Mr Sharad will see you now."

I stood up, swallowed and straightened my tie. I tried to put on a confident face, and walked through into the office. Mr Sharad stood up as I came in. He was a tall, imposing Egyptian man, with dark curly hair and a goatee beard. He stood about six foot two, with a muscular frame.

"Welcome, Christopher" he said warmly, putting his hand out. We shook hands firmly, him putting both big hands around mine.

"I am most pleased to meet you at last Christopher."

"I'm pleased to meet you too, Mr Sharad. It's a real honour to be given this opportunity."

"And I am sure you will... grasp it, Christopher. You understand the opportunity, of course?"

"Well - not really Mr Sharad. I only really know that I'm going for the position of personal assistant, and not an actual secretary. I don't really know what it would involve, though."

"Oh, a great many things Christopher. Many things indeed. You will be very much a companion to me as I travel. Donatella will take care of my schedules, travel arrangements and so forth. And yours of course. Your position might be considered... what do you British call it... a batman, a valet?"

"Oh, right. Yes, I see - that makes sense."

"You can consider this a two week trial period. There are other qualified entrants of course, but I have great hopes for you."

"And how would you like us to start, sir?"

Mr Sharad smiled. "We have already started. You will join me in a drink, yes?"

---

And that was how it started. We took a few drinks, and then we spent time talking. We mainly talked about me, although I did learn that Mr Sharad was the son of a great landowner in Egypt, and had built up a mighty import/export business from scratch. Over the week, I fetched and carried for him, and accompanied him in his trips around the city and to the golf course. He took great interest in my own hobbies, and limited skills. I had developed hobbies and interests at university at the cost of a better degree, which is why I could only get a job at data entry. But I had got good at squash, ballroom dancing, massage, tai chi, and of course sex. I hadn't intended to boast that of course, but he talked me into it on the last day of our 'trial period', when we were drinking in his penthouse. And that's when things started to change...

Over a late dinner, Mr Sharad had worked onto the subject of my skills as a masseur...

"Yes, your massage. You have not demonstrated this skill of yours yet, I think."

I shook my head. "Would you like me to?"

Mr Sharad nodded. He emptied his glass, then stood as he gave it to me to refill. I took the glass and emptied my own. I bent to pick up the carafe of spiced wine. When I looked up, Mr Sharad had started to remove his shirt. I looked up at him like a subject before his king as he steadily stripped his torso of its coverings. I admit I was staring as his muscular body came into view. He stood half-naked, towering over me, before turning and walking off to his bedroom. I stood, thinking quickly. I dashed across to the kitchen, where a decanter of finest olive oil stood on the counter. I grabbed it, and stumbled after him.

When I reached the bedroom, he was stripping off his trousers. He looked at me, fixing my eyes with my own as he reached down to peel down his tight briefs. I was transfixed as momentarily he stood proud and naked, his body muscular and hairy. Between his thighs hung a heavy cock, five inches long despite its languid state. The base of his shaft was buried in a hairy jungle of dark curls, framed by a pair of large balls. As he turned, his firm buttocks came into view, flexing as he climbed onto the bed. I couldn't move until he finally stopped, his body spread out on the huge bed.

Nervously, I stepped forward and clambered onto the bed, pouring a measure of olive oil into my hands. I spread it out onto Mr Sharad's broad back, stroking my hands over his deeply tanned skin. My heart pounded as I did my best to massage his body. Mr Sharad lay like a sultan as my hands moved over him. I ministered to him for several minutes before he spoke.

"You have an excellent touch, Christopher. Most relaxing."

"Th...thank you sir." I stammered.

"You learned to do this in University I understand?"

"Yes sir"

"I have had many massages in Asia and Europe, and many were less pleasant. But there has always been a pattern you do not seem to know."

I flinched, terrified. It was the last day of my trial period. I didn't want to mess things up now!

"What sir? Whatever you want!"

Mr Sharad grunted. "The one receiving the massage is the master, yes? The other his servant?"

"Yes - yes, of course sir!"

"The servant must show their lower position. They are always naked." he said firmly.

Naked? Why? My eyes darted about as my thoughts raced, but one thought was clear - I had to keep him happy. My fingers darted to the neck of my shirt, fluttering at the buttons.

"Of course Mr Sharad. I'm so sorry!" I cried as I stripped off my shirt. I bounced to my feet so that I could quickly push my trousers and briefs down. My socks followed. I knelt by his side again, both of us naked, reaching out to his broad shoulders again.

"Straddle me, Christopher" he ordered. Eyes widening, I did as he asked. I sat at the top of his thighs, legs spread wide by the width of his lower body. My balls hung down, but not my cock. Half-erect, it lay down the crack of his buttocks. I started to press down the erector muscles of his spine, trying to push past the confusing feelings of arousal clouding my mind.

"That is better Christopher," he said after a few minutes. "Now kneel up so that I may turn."

I did what he said, lifting one leg so that he could turn over beneath me. When I sat back again, our cocks hung against one another. As mine stirred, I looked away, eyes running up his flat stomach and hairy chest to his strong jaw and face.

"Rub the top of my chest," he ordered.

I picked up the oil, and poured it over his pectoral muscles, shuffling up his body to reach. His cock was now beneath my buttocks, but mine no longer lay against him, standing proud in the air between us. My hands trembled as I spread the oil over his strong chest. Mr Sharad regarded me with a slight smile.

"I will wager that you practiced this to seduce women, yes?"

"I... I suppose so Mr Sharad. I mean, that was why I took the massage course, and the dancing classes."

"Your touch is excellent. You must have seduced many women, yes? A handsome boy like you?" I swallowed, not knowing the answer.

"Tell me Christopher, have you ever done it to seduce a man?"

"N...No"

"Have you ever been seduced by a man?"

I hung my head, shaking it.

"You are my servant Christopher, yes?" Mr Sharad asked.

"Of course - of course, Mr Sharad"

"Then move down my body, Christopher. Finish your task."

I swallowed again, but started to move my hands down. When they were resting on his flat stomach, I was forced to move back down his body. Beneath my buttocks, his cock had reared up, and I had to half stand to get over it. In moments, I was kneeling on his shins, legs wide apart. My balls were tight against the base of my hard shaft, which stood proudly, jutting into my belly. It was a fairly average six inches; nothing to be ashamed of until you saw Mr Sharad's manly erection.

His cock stood proudly erect, nine inches of thick dark man-meat. He was circumcised, the glans a deep purple knob on the end of his shaft. I stared at it, my hands on his belly. I wasn't massaging any more, and he spoke.

"Take it in your hands" he ordered.

I did as he said, curling my fingers around the thick shaft. Unconsciously, I began stroking my hand up and down. He groaned, a deep rumble in his chest, his eyes closing. I took this as a sign to continue, pumping my hand up and down.

As I masturbated him, my neck bent, and I found myself closer to his cock. I stared at it so much; I didn't notice his hand curl around behind my head. He applied gentle pressure, and I came down. As I approached his shaft, it seemed entirely natural to open my mouth...

Musky and masculine, the bulbous head slipped between my lips. The scent and taste of him filled my senses to bursting, and my lips closed over him. My hand kept pumping slowly, masturbating him into my hot mouth. His fingers entwined in my hair as I sucked him. His cock was so thick; I was scared to take it deeper, keeping just his glans in my mouth. He seemed to enjoy it, and I closed my eyes as I jerked him off. After a lifetime of pumping, or maybe just a few minutes, his cock bucked and kicked in my mouth moments before he shot his thick come into my mouth.

I gulped reflexively, taking the first mouthful easily, but more kept coming, filling me to overflowing. I gasped, releasing his cock, shooting its last dying wads over my face as I tried to catch my breath. I sat back on his legs as I gasped, wiping my face. I wiped my hands on my thighs, confused and still very aroused. My cock was as stiff as it had ever been.

Mr Sharad had a smile on his face, and his eyes opened slowly.

"You learn well Christopher," he said. "Companion, servant and slave. See how well you adopt the roles I ask of you?"

I swallowed, confused. What did he want me to say?

"Stand up Christopher" he said. I obeyed, and he rose, leading me into the bathroom.

"Rub this cream over your body," he said, handing me an unlabelled bottle. He watched as I lathered the contents all over myself from the neck down, even helping with my back.

I stood there tingling as he spoke, telling me that I should shower thoroughly, and then oil myself from a scented bottle. And that he would be waiting in the bedroom.

As I showered, the hair came off my body with the cream. In minutes I was more naked than I had ever been, my hard cock tingling above my hairless balls. My skin was super-sensitive as I applied the scented oil I had been given, coating myself from the neck down again.

What was awaiting me in the bedroom? My mind was awhirl as I walked through, naked and hairless. What had I done? What more would I still do? Before this night, I had never touched another guy in a romantic way. I'd given my boss a blowjob already - and what would be next?

He was waiting for me, a glass of whisky in his hand. He downed it as he appraised me, and I stood silently, hands together at my crotch. He looked like a god, bronzed skin glistening from the massage oil. His thick cock was half hard again. I walked over when he beckoned me, and was shocked when he kissed me, his hot breath tasting of liquor. He took a half-step back, running his hands down over my chest. They moved around as he walked around me, caressing my body possessively and confidently.

"You are aroused, Christopher, yes" he asked confidently.

"Yes" I whispered shyly. I was.

One of his hands cupped my butt. "Get onto the bed Christopher - on all fours."

Oh god. Was he... no! But I did as he told me. My head hang, as I crawled onto the bed, hands and knees apart. He stood behind me, looking at my hairless ass.

"There is a saying in my country Christopher - a woman for children, a boy for pleasure. Do you understand this?"

I nodded silently. After a moment I felt his weight on the bed behind me.

"I shall take you now, Christopher. And there will be much pleasure for both of us."

With one hand, he urged my legs further apart. The second slid between my legs, and an oily finger slid deeply into my ass. I groaned at this shocking invader, my muscles contracting around it. He pumped back and forth a few times, adding a second thick finger for a few strokes before taking hold of my hips.

After a moment, I felt his cock brushing against my ass. I tried to relax as it pressed heavily into my tight sphincter. The lubrication did the trick as the oiled head of his thick cock slid into my ass with a jerk. I gasped as a shock ran through me. It felt indescribable as his cock slowly slid into me, and I groaned long and loud. Before I realised it, I was pushing back onto his cock, hungry for more in my ass.

As my pleasure mounted, Mr Sharad began pumping back and forth, settling into a steady rhythm in and out of me. My ass seemed like the centre of the universe as waves of pleasure and pain rolled over me. My breath was coming in pants as familiar sensations began to arise in my untouched and hairless prick.

Mr Sharad didn't miss a stroke as my pleasure grew to bursting. I cried out with joy as I finally came, explosively erupting all over my belly and the bed sheets. But the pleasure continued as he continued to use me, and the seconds turned into minutes. Tears rolled down my cheeks, and my arms buckled as the sensations overcame me. My face was pressed into the bed, and my cock slowly grew hard again. As he approached his climax, I felt another coming. I tried to hold on, to wait for the end. Finally, he began to pant, and I felt his cock swell yet more inside me. It was too much, and we both came together, collapsing onto the bed in a sweaty heap.

After a while lying on the bed together, he rolled off and reached into his bedside drawer.

"That was very good, Christopher. And I have a reward for you."

He reached out, taking my right hand. Quietly, he slid a ring onto the middle finger, bent and kissed it.

"Your reward, my friend. Never take it off." He said gently.

When he released my hand, I looked at the ring. Purest gold, set with some sort of stone -- striped like polished wood. Tiger's eye, I think.

"Thank you sir," I said gratefully, still breathless.

"You may go now Christopher. Clean yourself and I will see you tomorrow."

He smiled at me warmly, and I smiled back. My head was racing with crazy thoughts, but I had to confess one thing -- I had enjoyed it!

The next day, I woke refreshed, a vague ache in my ass, as well as my pectoral muscles. I must have strained something, I thought. At work, Mr Sharad was pleasant company, but we were never alone, and in the evening he had a dinner engagement. I went home alone, and masturbated, thinking of the crazy night we had spent together. The ring gleamed as I pumped my cock, although I thought nothing of it.

The day after that, we were flying out to Sinai for a few days. I was still having aches and pains in my upper chest, and cramps in my lower abdomen, but I didn't feel ill. I packed my bag, and went to Mr Sharad's apartment to pack his. He was in the shower, and I quietly made a pile of his clothes in the dressing room. As I did, I heard the shower finish hissing, and a few minutes later he came through to the dressing room. He wore a thick towelling robe, water droplets glistening on his skin.

"Aah, Christopher. Good morning. Are you nearly finished?"

"Um, yes Sir. I think I've got everything." I said, not entirely confidently.

"Good," he said. "Now, I believe that there is time for a small indulgence..."

He opened his robe, revealing his naked body. He stood waiting with his hands on his hips, half-erect cock protruding from his crotch. It was obvious what he wanted.

My mind was blank, thinking just of what lay in front of me as I slowly walked towards him. For some reason, I had none of the doubts of the last time this had happened. In fact, I found myself excited. His cock rose as I knelt down in front of him, my master. Taking his cock in my hand, I spotted a drop of pre-cum forming on the tip and licked it off. It tasted like mine but I savoured it like a guilty pleasure.

In moments, my lips were wrapped around his big cock head with my tongue licking it all over. My mouth and tongue began working his meat like I was an accomplished porn star. I wanted to! I wanted to suck him like a pro. I wanted to give him the best head of his life. I started jacking the base of his dick as I licked it up and down. I was really getting into it, licking and sucking his balls, kissing the shaft, and trying to take it deep into my throat. It was during a very deep plunge when he suddenly grasped the back of my head and began shooting hot jets of cum down my throat.

He gasped, taking a few moments to gather himself. I knelt patiently, unsure what I should do next.

In a minute, he smiled, and patted my cheek possessively.

"Most pleasurable my dear," he said. "Now finish packing -- the car will be here soon."

He turned, and left the room. I was left sweating, panting slightly, and my own cock stiff beneath my clothes.

In the car, he talked to me like he had before, discussing politics and the news. Occasionally he took a business call. Once we were in the private plane, he seemed to want to read, and I busied myself in a book. It was basically a Who's Who of the business world, and I figured I ought to learn who Mr Sharad's peers were.

It was a long flight, and I got up occasionally, stretching myself out. My chest still hurt a little. I asked Mr Sharad frequently if I could get him anything, and eventually he said yes. He had me kneel between his legs again, taking another load down my throat submissively. Once again, he was off-hand afterwards. I couldn't understand why this made me flush -- not the blowjob, but that he seemed not bothered about it. Didn't it mean anything to him?

I spent that night alone in my room in his mansion in Sinai, setting an early alarm.

I woke with the sun. After I stretched and showered, I felt my face. It was still smooth. Why didn't I need to shave yet? There wasn't a trace of stubble. I shrugged -- it must be the after-effects of the depilating cream I had used. I examined the rest of my body -- almost hairless, apart from a little stubble at my crotch. I scratched my balls, which were tight up against my perineum.

I looked at myself in the mirror. I must be putting on weight, I thought. My butt was bigger, and there were definite man-boobs! Damn it! I really thought I was keeping in shape, but I guess all the rich food was piling up...

That day was busy for Mr Sharad -- he had many meetings, and there was a banquet that evening. I hovered nearby, doing my best to be entertaining, but there were many other people who wanted time with him. He didn't make use of me at all. Once again, I jerked off in my room; nipples tingling as my reluctantly short cock burst into spray.

I washed myself that evening, so I didn't need to bother the next day. Still no stubble either. When I met Mr Sharad for breakfast, my heart lifted a little. I found myself smiling just to see him, and enjoyed eating in his company. He had less to do that day, and we played tennis in the afternoon. My chest ached a lot -- my increasingly obvious man-boobs were feeling heavy, rubbing against my T-shirt. The nipples protruded clearly through the shirt, and I noticed him looking at them a few time. Afterwards, we went for a steam.

We sat in the steam room in our swimwear -- me in shorts, him in Speedos. His trunks bulged dangerously, and I couldn't help staring. Eventually, he caught me.

123
  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Transformed

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 8 milliseconds