The New Flatmates Pt. 01

At 21 life for me wasn't going quite how anyone had planned. The first 16 years had been as a typical boy, albeit a short, skinny and nerdy one. The next couple of years I spent discovering my bisexuality while also discovering a love of cross-dressing. At 18 years old, I came out to my family as gender fluid and decided to change my name, now going by Kris / Kristy. While they were relatively supportive of me, it caused enough friction that I eventually decided to move away to another city. I managed to support myself doing a few jobs over the last couple years and live in a small studio apartment, but the ever increasing rents and cost of progressing by feminization were putting a real strain on my finances. Loosing my current job was the last straw, and it was also likely due to how much more feminine I had become over the last year on hormones, even if they wouldn't say it out loud.

So here I was, living in a city where I barely knew anyone, looking for a new job, an affordable apartment and quickly running out of money. Two weeks later I had managed to pick up some part time work, but had no luck on finding cheaper accommodation.

I was getting desperate enough, I was even venting about it to the guys I was chatting with on a hookup app. Most of them simply ignored the gripe and changed the subject or made some vulgar joke about it. But then one of the guys I was talking with said there was an extra room in his flat and we could work something out. I knew what he meant, but he was also quite attractive and seemed quite smart and sweet through the rest of the conversation. So I thought it'd be a win-win situation, but neither of us could have imagined just what was in-store for me.

After chatting for a while longer, we decided to meet at my place that night to discuss things and what I thought would be an audition of my skills. I cleaned myself up and got ready for the date. I was already hairless from regularly waxing but did a round with the razor to make sure I was smooth. A few enemas and a shower later I was ready to do my makeup. He seemed to particularly like a few pictures I shared in an e-girl style, so I decided to go for something similar. With colorful pink and purple eyeshadow, matching lipstick, long winged black eyeliner, pink bra and panties, white knee high socks, pink with white plaid miniskirt, white crop top and pink shoulder length wig. Topped off with matching earrings and belly button piercings, some cute pink platform shoes and some pink leather garters with heart detail to hold my stocks up. I looked at myself up and down in the mirror, getting the skirt just right, so my panties would be visible when I was doing anything other than standing up straight.

He arrived a couple minutes past the agreed upon time, introduced himself as David and I could see in his face just how much he liked my outfit. We sat on my bed and exchanged pleasantries, then began discussing a few things about ourselves. Later I moved to his lap occasionally kissing and stroking his face, while he reached under my skirt to grope my ass while we kept talking. After a while he bought up his flat and the empty room.

David lived in a 6 bedroom house with 4 of his friends, they were all in their late 20s and had good jobs. He explained they had been looking at renting the extra room but hadn't found anyone they could all agree on. Since they were easily making rent between them, there was little financial motive as well. On top of that the friends had begun fighting over chores and keeping the place clean. So when I mentioned my situation to David, he had an idea. I'd have a place to stay free of charge and in exchange, I'd do all the chores for them, cook, keep the common areas clean and do their laundry. Having been sure I'd have to do sexual favors for him - and a little disappointed he didn't mention any - I asked if there were any other requirements, because it all sounded too good to be true. David replied, that it's not a requirement, but he would like me to be dressed as a girl as much as possible and for us to continue having a sexual relationship as long as both of us wanted. I agreed, trying not to sound too eager and kissed him passionately on the mouth.

Being much bigger than me he easily flipped me from his lap onto the bed. Leaning over me and said, "Once we're done here, why don't we head back to my place? You can see the place and meet everyone."

"Sure," I said, barely even thinking. Then I began making out with the handsome stranger that I was soon going to be living with.

As I was kissing him, he took off his pants and broke away from the kiss to sit next to me. I got a good look at his 8inch hard cock and took the hint to move off the bed, kneeling in front of him and slowly began to suck it. Working my way down the shaft to get it nice and wet. Once his cock was covered in slobber, I went into deepthroat his member and got my lips all the way to the base. This elicited some moans from David as he moved his hand to the back of my head.

"What a good little cock sucker you are," he exclaimed. I looked up at him trying as best I could to smile with my mouth full and began to move away. But his hand stiffened, holding my head down as he simply said, "Not yet."

I tried remaining as calm as I could while he held my head down. Slowly tears started welling up in my eyes and rolling down my face. I looked up again at him with pleading eyes. Just as the panic was about to set in, he slowly eased the pressure, allowing my head to recede till only the tip of his penis was in my mouth. With my airway clear, I caught my breath as best I could.

"Good, girl," David said with a more stern tone. "Now listen carefully, every time I say so, I want you to deep-throat my cock and hold it for as long as you can physically endure. Anything less will result in a punishment. And until I say we finished, you will not let the tip of my penis out of your mouth. Is that clear?"

I looked up at him and nodded my head in confirmation, being conscious of keeping the tip of his cock firmly in my mouth before continuing to suck it.

This continued for what felt like over half an hour, every few minutes he would instruct me in a stern and direct voice, and I would deep-throat him and hold it till I was crying and gagging and desperate for air. Then after coming back up I would work the head with my mouth and use my hands to stroke him, catching my breath and waiting for him to tell me to go again. He occasionally changed things up by spitting on my face while I was sucking him, adding to the increasing amount of fluids everywhere. I also received a couple spankings as punishment for not holding the deep-throat long enough. On the next instruction while my face was pressed into his crotch and his cock was buried in my throat, he would lean forward to spank my ass. This made it extremely difficult to concentrate on the cock in my throat, but I also held it till my body was screaming, not wanting to be punished even further. Eventually, after one more long deep-throat, he said stop and my aching jaw finally left his member. His lap, the bed and the floor beneath us was covered in spit and I could only imagine what my face and make-up looked like after all of that.

"On the bed. Ass up, face down," he said, standing up, before asking, "Where, do you keep your lube?"

I pointed out the desk in the corner as I climbed onto the bed, grabbing my pillow to rest my head on. Still catching my breath, with my ass now in the air waiting for him. As he searched around the desk, he found a couple bottles of lube as well as some of my toys. He threw them next to me on the bed as he walked over. Then he lifted my skirt up to reveal my panties which he slowly pulled down my thighs to my ankles before removing and throwing onto the floor.

Looking at my tight asshole he pushed one finger against it. "You sure are tight for being such a whore. But my sluts know to be always ready for a good hard pounding! I shouldn't need to waste my time stretching you out before fucking you. And once you're living with me, it will not be acceptable for your ass to ever be so tight. I should be able to use it whenever I want. So I suggest you put those toys to good use, especially that butt plug of yours. For today I won't force anything or damage that hole. But you still need to be taught a lesson for not making yourself ready for me. I'll let you go ahead and stretch your pussy yourself, and I'll give you some gentle encouragement. " He ended the sentence with a sadistic smile.

I reached for a bottle of lube, then grabbed the dildo next to me. While I was applying the lube to it, he struck my ass cheek hard, causing me to drop the bottle. As I reached for the bottle again, he struck the other cheek, causing me to jolt forward again.

"Better hurry up or your ass is going to be raw by the time I start fucking you!" he said, followed by another slap on my bottom.

I quickly applied enough lube to the dildo and moved it to my hole while he continued to alternate hitting my cheeks. Having chosen my medium size dildo it took a little bit of time to try and work the head in as he continued to spank my ass. Sensing it would take a bit longer than he thought, he moved to a more comfortable position. Kneeling near my face, resting his hard spit covered cock on my head as he reached around with both hands to pull my ass cheeks apart. This initially helped a little with my task, till one of his hands released my cheek to move away and swiftly return with a good hard smack. I worked the dildo as best I could, trying to stretch my hole, using far more force than when I'm usually pleasuring myself with it.

As he kept spanking my ass, he spoke again, "Once you feel you're ready, beg me to fuck you!"

I managed to work most of the dildo into my hole and fuck myself a couple of times as he continued his assault causing both of my ass cheeks to feel on fire.

"Please! fu....ck me like the sl...ut I am!" I begged, still working the dildo as he continued to spank me.

"That didn't sound very convincing," he replied, continuing to spank me.

"Please, I nee....d your hard co....ck! I need you to -...ugh - use me for your pleasure! I want to be no...thing more than your cock sleeve and cu....m rag! " I pleaded, trying my best to speak through the spankings.

"Do you think you're open enough for me? " He asked, punctuating his question with another slap.

As soon as I answered yes, he pushed on my hand hard, making me scream as he pushed the rest of the dildo in. Pressing down even more on my and the dildo for leverage he spun his body around and was standing over me on the bed. Then he grabbed the base of the dildo from my hand and pulled it out in a single swift motion, making my body twitch.

He poured some lube over his cock while standing over me, stroking himself to spread it out and dripping a large gob of it onto my ass. Then beginning to push his way into my boy pussy. Still encountering some resistance, he spanked my ass again to make a point but said nothing. He kept a steady force until the head of his cock entered my hole causing a gasp from me. He continued to slowly push until his body was firmly up against me and his entire cock was buried in my hole. Then he began pulling back till just the tip was inside me. He forcefully thrust back in this time, forcing my face into the bed and eliciting a moan from me as I held tight onto the bed sheets and pillow. He continued, picking up the pace, slamming his hips into my sore ass cheeks, grabbing my hips for leverage to make each thrust more forceful, sending a shockwave through me each time he slammed his body into mine. Slapping his body against my cheeks with each thrust, reigniting the fiery pain from the spanking before. After some time of this, my legs were no longer able hold my body up against his thrusts as he slammed me into a prone position. But he didn't miss a beat as he continued pounding my ass, putting his entire weight on me, pushing me into the bed.

I had lost track of time and had no idea how long he had been going at it pounding my ass, but we were both covered in sweat and by now my hips were moving to meet his every thrust. Finally, he groaned with a couple of slow, powerful thrusts as he came deep into my ass before collapsing on top of me, his still hard member in my ass. For a moment he was fumbling for something next to me on the bed, before pulling out and standing up. As I went to turn around I felt something at my asshole again. He rather easily pushed my butt-plug into my well used pussy, causing me to yelp in surprise.

He walked to the chair in the corner, had a seat and spoke again. "Put those panties back on and fix your makeup, and do not touch that butt-plug or your clit. Time to go see your new house and flatmates."