The Roommate

After college I got a job with a company where a friend of mine from school also had a job. He already had an apartment and asked if I wanted to share it with him to help save on the rent, I readily agreed. Since we were in two different departments we didn't always keep the same work schedule and so I was often by myself as he would travel more than me. One night I decided to get a blow up doll and see how it was. Since I didn't want to spend too much money the one I got was not that great and the holes were not the smoothest, but I would dress her up in my clothes, get dressed myself and pretend we were lesbian lovers. Since my roommate seemed to always be away I became more and more bold and began to dress up in pantyhose, heels and a skirt when I was home. There was just something about wearing pantyhose that really turned me on.

One night I was feeling really kinky and took my strap on and placed it on my blow up doll. I then got into a 69 position and while I pumped my rod in an out of her mouth I bobbed up and down on hers. I was so into it that I didn't hear my roommate come home or even know that he was standing at my door watching me. It wasn't until I felt his hands on my hips that I realized I had been caught. He didn't say a thing but lifted my skirt and began to probe my backside. I had planned to ride the strap on and so I had lubed myself up, so when he found me ready he merely unzipped his pants and placed his hard on at my opening. Without saying a word he slowly entered me, filling me with his monster cock.

Once in, he slowly withdrew it until only the tip was inside and then began to pound my ass. Just as I felt his cock begin to swell I blew my load all over the face of the blow up doll and then felt him thrust all the way in and fill my bowels with his load. As he softened, he told me to put on fresh lipstick and join him in the living room. As I knelt there reveling in being filled with such a big cock and experiencing such a climax it didn't dawn on me that he knew I had lipstick.

As I entered the living room I could start to feel his load leak out of my ass and start to run down the insides of my thighs. I found him sitting on the couch naked from the waist down. He beckoned me to kneel between his legs and start cleaning him up. While I sat there with his cock in my mouth he explained that he had found some of my female items and had wondered about them, but when he never saw a girl come over began to suspect. When he came home tonight and heard me making noises he wanted to confirm or deny the girlfriend theory and when he saw me doing it with a doll all dressed up he knew he had me.

He then explains that from now on I would always dress feminine when I was home and that I would be at his beckon call. In return he wouldn't tell anyone especially the folks at work, as I could lose my job. He told me that if I agreed I was to suck him hard again and keep going until he rewarded me. Seeing as I had no other option I continued to suck on him. As he gets harder I realize how big he really is and can't seem to get all of it down my throat. He tells me not to worry that I will have lots of practice. He tells me that since this is Friday we will go out shopping for some additional items for my wardrobe tomorrow. As he begins to swell he grabs my head and holds it so that just the tip of his cock is in my mouth and begins to blow his second load for the night.

As my cheeks puff out from all the cum, I try to swallow but some leaks out and runs down my chin. When he is finished he tells me that he is really going to like having me as his roommate. He finally lets me go and allows me to stand up, as I go to leave he tells me to just go to bed as I am and that he will wake me in the morning.

The next morning I am awakened by my roommate placing his cock against my lips and telling me to open my mouth. After getting my bearings I slowly opened my mouth and began to suck. He tells me to just be still and swallow, I don't understand until he starts to pee in my mouth. My first reaction is to pull away, but he has anticipated that and has a hold of my head. He then forces more of his cock down my throat and tells me to just relax and swallow. I do as he says and before long he is done. He then tells me to keep sucking and get him hard. Once he is hard he tells me to suck out my breakfast, as he blows his load and I swallow it down he tells me to get out all of my crossdressing stuff so he can see what I have and what we need to buy.

I lay out my clothes, shoes and make-up. When he asks about my toys I reluctantly pull those out too. After surveying my items he determines that I need to buy several more pairs of heels, some more bras, a pair of inserts for the bras, some dresses, more tampons and pads, some more make-up and a wig. He then tells me to get dressed to go out. As I move to put my stuff away he tells me to wear something from what I have out.

I start to object but he just looks at me and I know any resistance is futile. I pick a pair of pantyhose, my stirrup pants a flowery t-shirt and some low heels. He then has me put on a little bit of make-up. He also makes sure I bring along my purse, filled with lipstick, lube, a tampon and my driver's license and credit cards. Needless to say I am extremely nervous as we walk out of our apartment to his car, especially since he places his hand on my ass as we walk.

Once in the car he has me pull his cock out of his pants and stroke it as we drive. We drive for quite some time and I finally realize he is going to a mall in the next town over and am grateful for that. Walking in, we immediately head to the Piercing Pagoda and I get both my ears pierced. Next we head to Fredericks of Hollywood where I buy a garter belt, nylons, and some bras along with some other sexy items at his digression. Whenever I need to try on an item he goes with me so he can see how it looks.

Next we hit one of the big stores in the mall and I pick up the remaining items that I need, except for my wig. For that we head to a specialty shop. As we walk in he tells the clerk that I am looking for a wig and need help. Since I wear my hair short she places a cap on me and then proceeds to help me try on different wigs, until we find one he likes. He tells me to wear it home and asks the clerk if I can use their bathroom to change into some of my new clothes. She is a little hesitant, but finally says okay.

We walk into the back and he tells me to put on one of my new bras with the inserts, my new green dress and matching high heels and my new garter belt and nylons. When I ask about panties he tells me not to worry about them. After getting dressing in my new clothes I feel so sexy that I start to get hard. I step out to show him and he immediately sees my hard on tenting my dress and smirks. He tells me that unless I want to get arrested for lewd behavior I had better learn to control myself.

I realize what he is talking about and put my hands over my groin. He tells me that he will gladly help me take care of it. As he approaches he tells me to hike my dress up around my waist and to kneel on the floor. He then takes out his cock, tells me to place it in my mouth and while I suck him off I can jerk myself off. As I suck, I reach down and begin stroking my cock. Due to all the excitement and dressing up, I quickly blow my load all over the floor. He tells me to scoop up my seed and eat it just as he fills my mouth and throat with his own load. As I swallow it down I can't believe how I got myself into this position. He then tells me to stand up and smooth out my dress and warns me to try to control myself. As we leave the store he thanks the saleslady and tells her we will be back.

Once we get back to the apartment my roommate has me put on a fashion show, showing off all my different outfits and accessories. Every once in a while he has me stop and either kneel down between his legs and suck him or impale myself on his hard on and ride it for a while. Once I am done with the fashion show he informs me that I am way too hairy and that from this point forward I am required to be hairless from my neck down, I have to start growing my hair out so I could style it in a girlish fashion, I have to keep my boi pussy lubricated at all times and filled at all times.

So if his cock isn't up my ass I have to have either a butt plug in it or a dildo. He tells me he has a doctor friend and is pretty sure he can get me some "vitamins" that I can start to take in order to help me look and feel more feminine. I have to be dressed en femme whenever I am not at work, and while at work I have to have only girl clothes on underneath my work clothes and that he will be inspecting me at random to ensure I am complying. He tells me that if I fail to follow any of the new rules he will punish me.

To ensure I understand he is not kidding he tells me to lay over his lap so he can show me. As I lay across his lap, he lifts my dress, exposing my bare ass framed by my garter belt. I cringed in anticipation of what is about to happen. He immediately lands five quick slaps across my backside causing me to jerk and let out a scream. He tells me that I am to lay still and take my punishment without any sound. If I want to I can cry but that is it.

He asks if I understand and I simply nod. He then proceeds to give me a rather long spanking alternating between my cheeks until I am blubbering like a baby. Once he sees he has the desired affect he tells me to stand up and thank him for teaching me my place and to curtsey. I quickly do and go to rub my sore ass when he tells me to leave it alone and to go and make us dinner. As I walk into the kitchen I wonder what else lays in store for me.

THE END