Our building’s landlord is a little over 6’, very stocky to chubby and in his 60’s. I had been dodging him for the past few weeks because I overspent and didn’t have my rent money again. Trying to avoid him a left a few voicemails how I promise to drop off the rent check, but the landlord Carl was not buying it this time.

He left me a voicemail saying we needed to discuss this month’s rent, or I would be evicted. I left another voicemail that I would be home at 7pm. I know he knew I crossdressed, and a few times caught him looking at my butt and legs when he thought I didn’t notice. Wanting to get on his good side, I put my hair in a ponytail, applied my favorite strawberry lip gloss and perfume. Next, I slipped on my cute pink skirt that snuggly covered my big butt, pink reeboks and pink ankle socks. I tried to look extremely cute and girly to get his sympathy and maybe just maybe he would let me skate until my next payday.

I was hoping he would be nice because in the past he did cross the line a few times when he asked why I liked dressing like a girl I just rolled my eyes and walked off.   I liked having as much distance between me and him. He always looked and smelled like a bum with a hangover. He’s gruff and a bit creepy, but I loved my little apartment and didn’t want to lose it, so today I was really desperate.

Right on schedule Carl knocking on my door, I took a deep breath and opened it. "Hey, Carl” I said in my sweetest girly voice. Carl said something under his breath, I think it was another sissy comment in another of his attempts to humiliate me whenever we crossed paths. "You have the rent?!" he said bluntly while staring at me. I stammered a bit as Carl rudely walked right passed me, straight into my living room and stood with a scarily stern face. Folding his burly hairy arms, he said only one word… “Rent?!” I looked at him sheepishly and apologized. I hoped my feminine helpless appearance would sway on him. His dirty pig face grinned as he said, “This is how you pay rent girly boy” Carl unzipped his jeans and whipped out his cock. It was rapidly inflating, and I thought maybe I didn’t think this all the way through…but, in my mind, I thought “okay I knew this situation could get ugly, just do it and its over” I’ve given head, just blow him and be done.

He had a wad of meat that plopped out his pants. So much old hairy cock, and now it was really getting hard. "Come on girly boy I only have about 20 minutes" he said with a stern face. Trying to slow things down I asked if he wanted a drink. Carl rolled his eyes, "Enough of your bullshit, you’re going this cock and then I will decide if I kick you out or not.” "Ok" I said awkwardly as I walked over to him. His hands were on his hips now as he proudly looked down at his meat then at me walking towards him. “No…, crawl faggot” He was totally enjoying the power of the situation, he controlled if I could stay in my comfy apartment or if I had to pack up and get out. I did what he wanted, got on my hands and knees, and crawled until I reached his crotch. He stroked his meat some and slapped it down on my forehead, then put his smelly balls in my face. Carl showed his dominance. He noticed me leaning away and slapped me harder with his thick veiny uncut cock.  "I bet your pretty lips can suck cock really good” Carl took joy in my humiliation. I let the comment go and started to suck his old swollen cock.

I continued to feel his big cock grow in my mouth. After a couple minutes of sucking, I took a quick breath. I was giving him the best blowjob of my life hoping for a quick end of the ordeal. My plan was to wait right until he was ready to blow then jerk him off, but now I didn’t want to piss him off.

When I was sucking slowly back and forth, his huge hand palmed the back of my head, and he shoved his cock completely down my throat. I tried to scream but meat was in my windpipe. I pounded my fists on his legs, then tried to push him off me but I couldn’t get away. My eyes teared up, thankfully he finally he let me breath. OMG his is nuts I thought! Coughing while catching my breath he just said “keep sucking my beautiful brown whore” again he forced me back on his swollen cock.  After face fucking me to the point that I was almost puked, he let me breath again. I know my mascara mixed with tears was rolling down my face, he looked at me with a fake puzzled face and said “Why are you crying like a little baby, I thought you sissies LOVED sucking big dicks” then he broke out in laughter.

“Get up sissy" he demanded as he grabbed me under my arms and yanked me up like I weighted nothing. He turned me around, bent me over his muscular arm and groped my ass under my skirt. The next thing I knew, his hand was gripping the back of my neck and pushed me over the couch.

“Bent over, I want to see your juicy black ass” Pushing me over the couch, he held me in place as yanked my panties down so hard they ripped off my butt. I tried to push back but it was no use, he pushed me so hard my naked ass was over the top of the couch. It felt so weird and scary being forced over the couch with my ass and puckered hole so exposed by a crazy man.

“Stop squirming” with that, his mighty hand that felt like sandpaper slapped my ass so hard I was in shock. I tried to cover my butt…then…WHAP, WHAP, WHAP, WHAP! “I will spank these fat cheeks so hard you won’t sit for a week!” he barked. “Wait” I tried to say something, then he pulled me back off the couch. I thought he changed his mind, but I was wrong. He looked at the couch for a few seconds then walked over to the front and pulled off the cushions and pulled out the mattress.

He told he was sick of my whining and didn’t give a fuck about my tears. I just wanted this to be over, so I got on the bed buried my face in the pillows with my ass facing him. “Get that air in the air sweet thing” I did as I was told and buried my face deeper in the pillows to hide my humiliation, this had gone so wrong. My bottom half was totally exposed except for the skirt, and he started again with the insults. Carl roughly grabbed my shaved little balls, “Is this the reason you are a girlyboy?” “You really are not a man, are you?!” “Is it because of this pee wee shit between your legs?" “What the fuck are these?!” He laughed even harder with my little balls between his thumb and forefinger. The more he laughed the further I buried my face in the pillows. I heard the familiar sound of a cock being stoked with oil, then with zero compassion forcefully pulled one check and slathered liquid on and in my hole.

“W-wait…” I managed to stammer out, “you need a cond..!” “Shut up” he shot back. I yelped as the pressure violently opened asshole against my will, it felt like his cock was ripping me open. I bucked and wiggled instinctive trying to get away from his cock abusing my poor butthole. I gave a long “Aawwww, GOD STOOOOOOP!!!” I cried out as his beefy cock popped past my anal ring and kept sliding in.  I whimpered and moaned as he pushed, widening my tight asshole pushing even deeper. “Take it, I know your black sissy pussy can handle my white dick” Carl mockingly hissed as he began pumping his massive meat in and out of my already sore butthole.

It was excruciatingly painful having his pole opening me up wider and wider; and his full balls slapped against me. He pulled back just so that the head stayed in then slammed back in. Carl was enjoying how uncomfortable it was for me, he seemed enjoy listening to my pleas. His slimy cock continued to pump in and out of my fuckhole as he rained down insult after insult giving him more power! “Faggot…sissy…stupid cunt…fat ass black gurly boy…” His pace was picking up, then he slapped me on the back of the head. “Here it comes faggot. Carl grabbed my waist with both hands and started hate fucking me viciously, then he pushed as hard as he could. My leg twisted as he went deeper than anyone had ever gone, the pain was unbearable. He pushed my head down in the pillows to muffle my screams.  Carl’s cock convulsed as he pumped thick white gooey sperm in me. It was so agonizing having the full weight of this bastard on top of me and his painful dick still stretching me out.

He finally rolled off me, from behind me I just heard him mockingly say “Look at you…. you are a fucking pathetic sissy” “I need to get a picture of this.” I was tired and sore and didn’t care.  I just continued to lay on my belly with my legs spread. The back of my body was sweaty and sticky, my destroyed ass felt bruised and battered as his gross cum oozed out of my gaping hole.  I finally worked up the strength to lift up my head and look back as he was wiping his now limp cock on the sheets, it was a mess. He put his pants back on, looked down at me, and rudely smirked “The next time you don’t have the rent on time, be in that cute little outfit and have your sweet brown ass pussy ready.” He manhandled my ass a final time then walked out the door.