Last week I went on a date with one of the partners who work at my law firm. He’s a corporate lawyer, Andy, quiet, demure, polite and I felt obligated to say yes because I’m just one of the legal secretaries. You don’t want to piss off the boss. He’s originally from Melbourne, Australia and he’s kind of cute in a dorky way but the accent tipped the scale and I thought I would have a good time. We had a lovely four course dinner at an upscale restaurant but it wasn’t until we were in the taxi ride home did I learn who he really was.
Without asking he slid his hand up my skirt, jammed his fingers in my pussy, pulled them out, smelled them, licked them and said “yes, I think you’ll make for a decent dessert course.” I was shocked, this didn’t seem like the guy I worked with or just had dinner with. I’ve always been afraid of men after how my father verbally and sexually abused me as a young one and as a teen he let his buddies do the same so I didn’t say anything. Andy told the driver we would only be making one stop, the Four Seasons in downtown Chicago. We both lived close by so I didn’t understand why he wanted a hotel.
He checked us into a luxury suite, even though we hadn’t brought any belongings, and we went to our room which was the nicest hotel room I’d ever been in. I stood inside the door and he closed and bolted the door behind me. He then circled me, looking me up and down as if he was a predator and I was his prey. “You’re a dirty, fucking slut,” he said, “and tonight, I’m going to rape you.” He said it so matter of fact that I wasn’t sure if he was serious. “Strip down to your undergarments now or I’ll punish you by slapping you hard across the face.” I did as he said. He began to run his fingertips up and down my body, and I was becoming turned on, feeling my pussy tighten and start to get wet and I could see the obvious arousal in his pants. Andy then gently began to unbutton each one of my garter belt buttons that held my thigh high stockings up, “I’m very pleased you chose to wear these, if you don’t please me, I will hurt you.” He rolled each stocking down individually, taking extra care to help me remove them. He then unsnapped my bra and let it slide down my shoulders and gently pulled down my thong panties and garter belt. Again he circled me and lightly touched different arousal zones of my body, circled my nipples with his fingers, across the small of my back, around my belly button and from my knee he slid his fingers up my thigh and again jammed his fingers inside of my vagina, hard, and circled them a little bit, and I moaned, “yes, I think you’re ready.”
“Get down on your fucking knees now, and hold your mouth open with two fingers on each side, wide enough like you’re having your teeth examined.” I was confused but I didn’t want to get hurt so I did what he said. He unzipped his pants, pulled out his surprisingly large cock that was rock hard and forced it into my mouth until it hit the back of my throat. The gesture surprised me but I was excited by it, and he could tell, he didn’t want me to be happy so he forced it again but harder and faster. And he did it again and again while I was choking and sobbing from the gagging. He was satisfied by my will not to pull away.
“Lie down on the bed, put your hands on your knees and pull them open wide while your legs lie flat on the bed and keep your mouth open but not with your hands anymore.” He took off his tie, put it around my neck and tightened it so tight that it was uncomfortable and beginning to affect my breathing. Although he had taken off his dinner jacket he was still dressed. “Close your eyes, I don’t want you to know which hole I’m going to penetrate next.” I did as I was told. I cried out as I felt his enormous cock slam inside my ass, certain that he had ripped me in two, and he tightened the tie even further. He pushed his penis in my anus over and over again until it began to feel good, and even started to play with my clitoris and I could feel myself starting to climax when he stopped suddenly and put his erection in my mouth again. “Not yet baby, you still have a long way to go before I let you cum, but if you’re a good girl, I will let you. So far you’ve been a very well behaved dirty little whore, I may let you become my special dirty little whore, my chosen one.”
After fucking my face for a short while he penetrated my ass again, with more force, always making sure I could just barely breathe with the tie around my neck. He pushed on harder and faster and started to play with my clit again and this time he moved his hand towards my pussy opening and suddenly slammed four fingers inside. I tried to cry out but the lack of oxygen made it difficult. “Soon, my special dirty little whore, soon I will let you free.”
He kept slamming his huge hard cock in my ass with so much force and speed and was using almost an entire hand to fuck my pussy, I could feel myself starting to climax, but I knew it had been a while but the lack of air made it too fuzzy to make out time. I was getting higher and higher, I was so close and he was going faster and harder yet, moaning that he was cumming too.
Suddenly the tie was loose and I felt myself release. I screamed out when I had the longest most intense orgasm I had ever had, it just kept hitting me in waves and when I started to feel my whole body vibrate because it was finishing he pulled his cock out of my ass, grabbed me by my hair and jerked my head backwards and came all over my face while saying, “yes, that’s my dirty little whore, you’re my special slut, you nasty filthy bitch.”
He told me to go to the bathroom and clean up and I did what I was told, I was bleeding slightly because he had forced his cock so hard into my ass, but it wasn’t anything severe. When I came out of the bathroom he was gone, tie, jacket and all. But he left a note…
“You may stay the night in this luxury suite and I ordered you a massage in the morning, don’t be late for work on Monday my dirty little special whore.”
