tagTranssexuals & CrossdressersHotel Porter to Private Maid

Hotel Porter to Private Maid


This is my first story, please leave comments below and tell me what you think, I hope to carry on the tale, if the readers like it.

I suppose I should explain how I got like this. How an ordinary guy who was a porter in a hotel became the sissy, dressed as a maid, with a butt plug firmly inserted into my tight sphincter, on my knees, and throbbing 8" cut cock hammering in and out of my mouth.

When I was at college, I had recently needed to get some cash, so I like many others decided to get a job. Due to my studies I had to work around lessons and that usually meant in the evening. I applied for what seemed like hundreds of jobs, which in fact would probably be about 15. I tried bars, restaurants, 24 hour shops, and hotels.

On one cold Wednesday afternoon I got home from studying to find a letter in my mail box, it was a letter from the hotel job I applied for asking me to come to an interview. I had applied for the job of a night porter, which as I could understand it from the description that would be to attend to room service, and carry bags for customers who had arrived late. It was the perfect job, it fitted around my lessons and bought me some extra cash.

The interview was on Friday so I had some time to prepare and get my suit ready and all the other stuff you do when you have an interview. Friday came around and the interview went well, with the manager offering me the job there and then. Through out the interview I did notice one thing the manager was looking at me in a strange way, a way that I had not really seen before. He was about 6'5, broad muscular shoulders which showed he worked out frequently at the hotel gym, short hair, piercing blue eyes, and dark hair.

I never considered myself gay, not even bi, to be honest I hadn't considered anything really, I was just your average guy, I have short blonde hair, blue eyes, stand 5'8, skinny but toned, at college I was no good at sports but I really enjoyed swimming, I was on the reserve for the swimming team, so I trained with the other guys, so I got a basic swimmer figure. I had never been really interested in girls or guys for that matter, so when this very attractive man was looking at me I kinda felt a little weird, and strangely aroused by it.

I was due to start work on Sunday evening I got my uniform, a red porter suit, and was ready for work. It was a quiet evening nothing much happened, the phone rang a couple of times and I took food to the guest's rooms. As it was approaching 2am, the phone rang, I answered it expecting it to be another customer.

"Hello room service, Alex speaking" I said in my cheerful way.

"Hi Alex, it's Matthew" said the voice down the phone, I froze in my spot, crap it was my boss, his voice was velvet to my ears and I got a little excited, I hadn't stopped thinking about him since the interview, and when I did I was at home jacking off. Maybe I was gay, and this was the man who bought those feelings out.

"Hello Sir, how may I help you?" I asked in my being professional at all times voice, Mathew chuckled

"Sir, I like that" he said, "When you have a moment can you come to my office, I want to have a chat and see how your first shift is going"

I agreed and said I would be there in a moment, and just before he hung up he told me to bring a bottle of wine from the cellar up to him. I got the wine placed it on a tray and carried it carefully to his office. I knocked on the door and a voice from within said "Come in". I was nervous, and yet excited to, I took a deep breath and opened the door and walked in.

Mathew was sitting at his desk reading something on his computer, his blue eyes turning to look at me as I entered, he smiled and I saw a row of bright white teeth, and a devilish grin.

"Come on in and sit down" he said pointing to an arm chair, I placed the tray with the wine on the desk and sat down like he asked me to. He got out from his desk and walked round, he picked up 2 wine glasses from the side board and placed on the desk by the wine, and with his back to me he asked.

"How you finding your first shift, any problems?" he said and opened the wine and poured it into the glasses.

"No, none at all, everyone has been really friendly and helpful" I said honestly, the few people I had met had been very friendly to me. As I spoke Mathew turned and handed me a glass of wine, "to celebrate a successful first shift" he said and clinked glasses with me. I thought this was odd, but hey I followed his lead and sipped the wine.

Not being a fan of wine really, but this one I really liked it had a sweetness to it, I sipped some more and we made small chat about what I was studying and if I enjoyed it, I was not much of a drinker and I slowly began to slur my words, however I did tell him I hated college and only went because my dick of a dad wanted me to go.

The room started to spin, gaining speed every time it went round, until I couldn't take it anymore and fell of my chair and onto the floor, then it went black. I couldn't remember anything else.

When I woke, my head was in agony, what didn't help was that my mouth was dry and I couldn't close my jaw, something was strapped around my face keeping my mouth open. When I tried to reach up to take what ever it was out I realised my arms were tied behind my back and then I realised I couldn't get up, a metal pole had been placed between my ankles, forcing my legs to spread, I was lying face down on a soft bed, my ass up in the air.

I was cold, a window was open and I could feel a cold breeze flow across my skin, I was naked, I tried to call for help but because my mouth was locked into one position the sound was in audible and muffled by the pillow. I couldn't see, at first I thought it was because my face was buried into the soft feathered pillow but I soon found out it was a blindfold.

"Don't panic" came a voice I recognised straight away, "I'm not going to hurt you, in fact if you let me I am going to make this an evening you will never forget and want to cherish forever" the voice was Mathew, his voice was soft and kind smooth and velvet to my ears.

I was still scared and began to cry, what was happening? Why me?

"Don't cry, just enjoy it" he said once more, and with that I was pulled round and lifted, my face now resting on his firm bare chest, and me on my knees. "This is how its going to be from now on, and trust me you will love it" he said kindly.

I couldn't help but trust him, his voice calmed me, I then felt him move away but his hands rested on my shoulders.

"I liked you from the moment I saw you Alex. I wanted you and in time I think you will want me." He said and began gently to rub my shoulders. The way he was talking was hypnotic, I instantly trusted him, as his rubbing began turned into gentle pushing and pulling my back and forth.

"Just do what i say and everything will be ok" he said "You were telling me how you hated your college, hated your father, your mother had left you, you have no siblings, your father couldn't care less if you where there or not".

"Shit" I thought how much talking did I do, I thought, he drugged me and I told him everything.

"I am going to help you, give you a better life, one you will enjoy, do you trust me" he asked kindly. I nodded in agreement. "Good, I love your body Alex, so smooth, I like that. I also like it when you call me sir, so from now on you will call me sir understand?"

I nodded one more time, the way he was talking excited me, my cock started to rise, Mathew obviously noticed and moved the hand on my right shoulder and reached down gently gripping 7" cut cock and gently pulling on it, it responded and got harder. I loved this new feeling. My tears stopped, the pain in my head had gone, now there was just excitement.

He suddenly stopped jerking my cock, and moved his hand away and rested on the side of my face, it was soft, "now just relax, everything I am going to do will make you and me very happy" with that he moved the other hand to the other side of my face and guided my head down, I felt something enter my open my mouth, my tongue instantly responded and licked the underside of his cock, as he rocked my mouth back and forth over his 8" cut cock, the fat head hitting the back of my mouth and pushing its way down my throat slowly, time and time again.

I heard Mathew groan slightly, and this pleased me more, I got more excitied.

"Such a pretty fucking mouth, just look how much it wants my big fat cock in it" he said, his voice more commanding and strong, it sent shivers through me as I felt it push its way through. I gagged and coughed and he pulled me back, a trail of saliva from his cock to my lips.

"Good girl" he said, and with that last comment he thrust my head forward and his cock at the same time, it forced its way down my throat passing my gag reflex and now rested, he carried on fucking my mouth, calling me "His little slut" and "his sexy cock sucking sissy"

He was right, loved every inch of his cock in my throat and felt sad when he pulled out and turned me on the bed and just dropped me. My face hitting the pillow, my ass in the air, my cock aching and throbbing, I felt the weight in the bed shift and then felt his smooth hands gently stoke my ass, "look at my little slut's pert ass, just begging me to fuck it" I moaned slightly, I wanted it I would do anything he wanted.

"Does my little Alexis want me to fuck her tight little ass?" he asked, I made a noise which I hoped sounded like "Yes fucking please" He smiled and then I felt something strange, I felt warm air blow over my hole, it sent shivers up my spine, I shake with anticipation, I then felt something stranger still, it was strong, warm, wet, and flicked my hole.

"mmmm" was all I could muster.

"That feel good Alexis?" he said and then buried his tongue deep in my ass, I squirmed and wiggled my ass on his tongue, not wanting him to stop. He then began to lick the rim of my hole and pulled away.

"You're a naughty little slut aren't you Alexis? You just want to be my fuck toy don't you Alexis you filthy sissy" he shouted. I got so turned on at being called names like that and even more so when he called me Alexis. I was his sissy, his toy, his slutty little Alexis and I loved every minute of it.

"That a girl" he said as I moaned in agreement to his remarks, and then with my ass wet and ready he began and inserted a finger. The pain I felt was intense as I felt him stretch my hole, push it in and out, he then added a second, doing exactly the same. I moaned with every thrust of his powerful digits. A third finger now, he was gently turning them back and forth, and then I was empty.

I wondered if I had done anything wrong, but suddenly I felt something else, it pushed and pushed until, I moaned as his cock went deeper and deeper into my ass. "Such a tight little pussy my Alexis has, does she like my big cock sliding in her pussy?" I moaned and tried hard to push my pussy down onto his big fat cock, this was obviously enough for him.

He started to pull back and thrust in, slowly at first, but like he did when he fucked my face gaining speed with every thrust. The pain had gone, I was gripping his cock with my ass, not wanting to let it go, he hammered away, all the time calling me his little slut, his little Alexis.

The feeling was intense, so intense that my cock erupted and shoot stream after stream of cum all over the bed, my body tensed as I shot my load, and this was the sign for Mathew to go to town. No softness, just pure animal fucking, he gasped and shouted.

"Im gonna cum in your tight pussy Alexis" he bellowed and shot his load deep inside me, he kept on thrusting, getting every last drop of his hot cum inside me, filling me.

He pulled out of me and before I knew what was happening his cock was back in my mouth "lick it clean bitch" he commanded, and I did.

When I had finished cleaning his cock, he undid the mouth brace, undid my tied hands and removed the bar spreading my legs, finally he removed my blindfold. I squinted at first and then my eyes adjusted to the light, he was standing in front of me, while I stretched a little on the bed, rolling in my own cum, feeling his ooze its way out of my ass, I looked at him.

"Did you enjoy that?" he asked back to his calming voice.

I nodded and said "Yes" and gasped as I tried to get my breath back.

"Yes what?" he corrected me, still using his smooth voice.

"Sorry, yes sir, I very much enjoyed it" I said with a smile.

He smiled to as if to say I told you so, "Do you want to be mine Alexis?" he asked, he didn't need to ask, I was his from the beginning, I just nodded. He smiled and leaned forward and kissed me gently. "Good, I'm glad". I looked around the room or should I say suite confused a little.

"This is your new home" he said, "it's my private suite in the hotel, no one will know you live here now, you will be locked in here, you are to be my toy, my little Alexis. I will bring your food, and drinks, your clothes are here, you won't need your old ones as you will be my private chamber maid. Understand Alexis?" he asked.

"Yes sir, I understand" I said softly, and with that I was commanded to clean up and have a shower, which I did. After the shower, the steam cleared and saw the maid's uniform hanging on the door, with a note, "Wear this".

I looked at the dress and then at the mirror, "Goodbye Alex" I said to my reflection and got dressed in the tight outfit, I had no underwear just stockings, a red garter belt, high heels, a blonde wig and a collar.

I walked out of the bathroom saw Mathew standing nude in front of me, his cock hardening as his eyes looked at me up and down, he smiled. "Come here and get on your knees" the commanding voice was back, and I responded straight away. I was on my knees in front of him, "good girl now get on all fours" I did as I was told.

He walked around me and stroked my ass some more "Such a fine pussy" he said and with that I felt something cold being inserted into my ass, he spread it around with his finger, then it was replaced by something a lot thicker and firmer.

"That plug will stay up there until I get back in a couple of hours" he commanded, "Now turn over" I obeyed and he lifted the front of my skirt showing my semi hard cock, he smiled once more "you are not allowed to play with that!" he said and suddenly I felt a tight ring go around my cock and balls then a click. " I have the key, you can still relieve yourself, but don't get excited or it will hurt" he said, he then slipped a pair of leather panties over my legs and over my now locked cock and balls and plugged ass.

"On your knees Alexis", I struggled at first but got there, and he then began to thrust his hard cock into my wanting mouth, fucking my throat hard, and loved it. He shot his load down my throat it tasted fantastic, the moment it touched my tongue I was hooked, then pulled out and shot it over my face.

"Don't move, don't touch it" he said commandingly "Until I have left, I want to leave my slut dirty and arrive when she is clean understand Alexis?"

I nodded it was difficult not to lick it as it dribbled over my lips, I watched as Mathew got dressed and moved to the door.

"You will be locked in until I come back. When I do come back, I want this place clean, I want fresh sheets after you spoilt them, understand?" he said calmly once more.

"Yes Sir!" I said obediently, when he left I heard the door lock, I stayed still for a time, a smile crossed my face, I was his.

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