My unexpected journey – part 4 by Desire2beagurl

Slowly I start to regain consciousness, my head still pounding and spinning from the nights events. I try to move but find it difficult since arms, legs, and bodies are splayed all over the bed and on top of me. As my senses return more and more I suddenly feel pain radiating from my ass. Then I notice that most of the bodies are only over my upper half and it seemed someone, or a few someone’s, took advantage and had their way with me while I was passed out. I could feel my sore hole straining to close as warm liquid leaked steadily out and onto the bed.I finally managed to squirm out of the pile and as I started to roll off the bed I was stopped by the body of my girlfriend, Kendra. She looked down at me and smiled, telling me good morning as she kissed me. Still trying to wake up completely I felt her raise my leg, pressing her body against my back. I gasped as I felt her enter me from behind, her hard cock sliding easily into my abused hole. Gently she pushed until she was fully seated inside me, then she began rocking her hips back and forth causing me to moan as the pleasure built up inside me. She gets into a steady rhythm and as I start to moan she whispers to be quiet so we don’t wake the others. The pleasure builds inside me as her hard cock steadily pushes in and out until I feel her push in one last time, her cock pulsing as she pumps her cum into me.

She bends down and kisses me again as her cock slides out of me, cum spilling from my hole again, my own little cock dribbling onto the bed leaving a small wet spot on the sheet. She quickly gets up and leaves the room leaving me to lay there and gather my wits about me. Gingerly I scoot off the bed, gathering what clothes of mine I can find and a few that weren’t. Quickly getting dressed I silently cross the room and head out the door, making my way down the hall and down the stairs to the kitchen where the sweet smell of coffee hits my nostrils.

I see a group of girls behind the counter giggling as they stand around the coffee pot. As I get closer one of the girls turns around and smiles at me, handing me a hot cup of coffee. I take it graciously and take a slug of the hot liquid. I notice a strange, yet familiar, taste to it and the girl tells me that it’s a special latte and everyone helped. A little confused I thank her, taking another gulp of the drink, making my way around the counter. Everything started to make sense as I came around the corner and saw that the “girls” were all half naked with their cocks still dripping cum. They giggled again as I drank down the last of the cup, making sure to lick around the lip of it, the salty taste of their cum lingering on my tongue.

I decided that it was time to go but with only my costume to wear I figured it wasn’t a great idea to walk around town in the daylight like that. Taking the back streets I quickly made my way across the city and back to my girlfriends apartment. I took the time to remember the events of the previous night and though I had a really good time I hoped there wasn’t another one soon. It’s one thing to be having sex with my girlfriend but not by a whole lot of people. Lost in my thoughts I wander the side streets until I finally get to her place, making my way up the stairs I see Kendra just getting to the door herself.

She smiles at me as she opens the door. I barely closed the door when she starts pulling off the pieces of her costume, making her way to the bedroom. I follow suit and begin to undress as I follow her down the hall. We start talking about the party and all the events that transpired that night. She stopped in the hall and looked at me, a bit of concern on her face as she asked me if I enjoyed myself at the party. I told her that I did in fact have fun and this seemed to put her at ease as she smiled and continued down the hall. As we reached the bedroom she pulled me to her, our bodies pressed against each other as she pressed her lips against mine. Our lips locked as I felt her snake her tongue into my mouth and I followed her lead snaking mine into hers. We kissed like this for a bit before she pulled away and smiled.

She opened the top drawer of her nightstand and grabbed something out although I couldn’t see what it was. Looking over her shoulder I could see the growing concern on her face. Moving closer I asked her what the problem was and she asked me if I still really wanted to be a girl. I stopped for a second and thought about it and with a big smile I proudly answered that I definitely still wanted to be. She squealed with delight as she turned around holding a silver device in her hand. She explained that it was a chastity cage and that if I still really wanted to be a girl I should at least try it for a day.

I agreed and she grinned from ear to ear as she sat down on the bed, putting the device over my soft little cock, and locking it into place forcing me to groan in pain. She showed me the key and then placed it in the drawer. I felt a huge discomfort at first but as I moved around a bit it seemed to go away. As the pain ebbed but was a steady reminder that it was there, Kendra picked up the newspaper on the bed and motioned for me to sit next to her. She said that since I wanted to be a girl that I would have to start a new life and that meant a new job since I wasn’t sure my old one would be all that accepting.

We scrolled through the want ads together and came across several that looked promising. After taking each one into account we decided on the maid’s job since it wasn’t very far and seemed like an easy way to make a little money. I placed the call and got all the information I would need as far as where to go, who I would be working for, and the basics of what I would need to do. Then they asked me if I read the ad completely, to which I replied that I had. They asked me if I understood that they provide a special service to their client, meaning anything the client wants the client gets. I affirmed with them that I understood and hung up the phone, explaining to Kendra what had transpired.

She clapped her hands and rummaged through her closet searching for something. She squealed as she returned holding a maid’s outfit in one hand, although it seemed a little odd to be an actual uniform, and a few more items to go with it. She helped me get dressed in the black lace bra and thong, making sure to tuck my caged cock between my legs so it wouldn’t bulge the tight underwear, along with a pair of sheer pantyhose and heels, which took me a few tries to get the hang of. Next she helped me on the pink maid’s uniform which seemed to be made of a shiny, plastic type material that squeaked a little as I moved and barely came down over my ass. She then helped me take out the extensions in my hair and affixed a pinkish wig that came down to my armpits in its place, ensuring a tight fit so it wouldn’t move around. Finally she put on the maid headdress and sat me down to do my make-up before giving me a kiss on the lips and walking with me to the door.

We kissed again as I left to start my new job and waved as I heard her say she would be waiting for me when I got back. The uncomfortableness in my crotch from the cage was beginning to subside by the time I made it to the apartment complex and rang the buzzer for the one I was supposed to get to. A gruff voice answered asking who I was and what I wanted. I explained that I was sent there by the cleaning company and moments later the door buzzed, allowing me to come in. I made my way inside and took the elevator to the floor I needed to. Getting off I noticed the area was rather run-down and dirty as flies buzzed over piles of trash and other things.

I quickly made my way down the hall to the door of my customer and knocked rapidly. The gruff voice I had heard before answered again telling me to come in. Opening the door the dank odor of the room assaulted my nose and I resisted the urge to vomit. Upon closing the door the gruff voice, which seemed to be coming from the bedroom, shouted again to get to work and not to disturb him. I quickly began cleaning the entire apartment starting with the kitchen, then the bathroom which needed serious cleaning, then the hallway, and finally I go to the living room. I had just gotten done picking up the last of the magazines on the floor and placing them on the coffee table when I heard footsteps behind me.

My nerves began to go into overdrive as I heard the footsteps getting closer and closer. Standing up and turning I stood facing the burly, huge man, who stood at least a foot taller then me, staring down and smiling a wicked toothy grin. He made his way over to the couch and sat down, eyes still glued on me. He asked me if I was new and I told him that I was. His grin got even bigger as he told me he would go easy on me and motioned for me to come closer to him. Remembering what the operator on the phone had told me I walked over to him, a polite smile plastered on my face. It wasn’t until then that I really noticed that he was completely naked and his cock was steadily getting harder.

In a flash I felt the man grab me and pull me on top of his lap, his hands grabbing and groping my ass. He lifter the back of my skirt up and slid my thong to the side pulling me down, his bulbous cock head sliding into my anus with disheartening ease. Gripping me tightly and moving me up and down like a rag doll he shoved his cock deeper and deeper inside of me, my anus stretching and spreading to accommodate the new intruder. Moans of pleasure involuntarily escaped my lips which seem to excite the burly man even more as he continued his assault on my rectum finally getting his whole cock inside me.

With me completely impaled his grip loosened and I put my hands instinctively on the back of the couch. Lust clouded my mind as I started grinding my hips and moving up and down on his cock. His moans and groans seemed to hit an animalistic nerve in me and goaded me into going faster and harder. Waves of pleasure built up inside me as I continued riding the stranger, my shouts and cries of ecstasy echoing in the room. His hands moved up and caressed my non-existent breasts, pulling the dress and bra to expose my hard nipple. His tongue lashed out, flicking it and sending shivers up and down my spine. I could feel his cock getting harder and knew it wouldn’t be long. Suddenly I felt myself lifted up onto my feet, spun around, and bent over forcing me to grip the side of the coffee table, my ass completely exposed.