by Raven Watyrs
It wasn’t two days later that I found myself outside a hotel room door about to meet my very first client. I had been utterly nervous and stood there shaking in my spiked heels for at least 10 minutes before I grew the balls to actually knock. I didn’t know what to expect on the other side, but I was pleasantly surprised when I opened the door and there stood a smokin’ hot business man, about 40 years old, looking smouldering and sexy with a glass of whiskey in his hand. Not too shabby.
My first experience had been fantastic. After enjoying a whiskey with Brian, his name, he asked me to stand next to the vast window which over looked a huge park. He sat in the corner and asked me to strip for him, everything off except my heels. I had been quivering with anticipation, relishing the naughtiness of fucking a stranger for money. I slowly stripped, removing my dress, then my bra, then I peeled my panties down my long legs, leaving my in stockings, a garter belt, and my black stilettos. Brian had licked his lips and eye-fucked me while I stood there, rubbing at the bulge in his pants before ordering me to get down on my knees and crawl towards him slowly.
I promptly dropped to my knees and starting crawling towards him, my massive tits swaying languidly beneath me. I moved like a cat and crawled up his lap, undid his pants, and pulled out his beautiful dick, hot and smooth to the touch.
“Do you want me to suck your cock, Brian?” I purred up at him, stroking his length and feeling him shudder at my touch.
“You know it,” he said, leaning his head back and enjoying his experience.
I wrapped my lips around the head of his dick and started sucking. I ran my tongue under the ridge of his mushroom cap and explored his length, licking and kissing down the shaft of his impressive length. As I mentioned, I was no nun; I’d had my fair share of man meat in my 21 years, but I had to admit, Brian had a nice looking dick. Long, pink, perfect.
I bobbed up and down on him until he was rock hard and close to shooting his load down the back of my throat. He’d hired me for more than a blowjob, so before he blew his salty wad into my mouth, I crawled the rest of the way onto his lap and straddled myself over top of him. I grabbed a condom from the table beside the chair he was on and slid it over the length of his shaft before rising up and positioning his mushroom capped head at the opening to my very excited and very wet slit.
He groaned and reached for my tits, massaging them and kneading at them, pinching my nipples before sucking them into his hungry mouth. I slid myself down his shaft as he sucked and lapped away. He pushed them together and flicked his tongue over my nipples sending electric jolts down to my clit.
I pushed down and started to ride him, sliding my tight tunnel over his throbbing cock. I moved slowly at first, grinding my clit into him as I lowered down, then sliding back up, torturing him with my tight pussy. I started riding faster, bouncing in his lap, my tits rebounding in his face. Brian didn’t last long with me grinding into him like a seasoned cowboy and I felt him tense up and cum hard. He cried out and spurt his hot load up my juicy cunt in long delicious jets.
Twenty minutes later, I was back in my car heading home for dinner. It was the easiest $300 I’d ever made. Plus it didn’t hurt that I got to ride a hell of a cock in the process.
I was beaming when I got home. Absolutely thrilled with my new situation. I wished I could shout it from the roof tops! But obviously that wasn’t wise. Probably best to keep my little trysts under the radar, even if I wished I could tell someone. I knew it was weird, but I really did wish I could have shared it with my step-father, Jason. I wasn’t all that close with my mom, but I’d always been close with Jason. He had come into the picture about five years ago and I took to him right away. He could be kind of bossy sometimes, but he cared for me and looked out for me at every turn. Plus, he was unbelievably good looking and I’d nursed a burning crush on him since day one.
I didn’t live at home anymore, but called weekly to catch up. I had been careful to keep the details of my job as vague as possible, telling them that I was waitressing in a club making lots of money in tips. My mother didn’t seem to care much about what I did; she wasn’t interested in my life, which was fine with me. She was kind of a bitch and we’d never been close. I couldn’t wait to have a baby so I could be the exact opposite type of mother that she was. But Jason said he was proud of me and that he wished he could help me out more. I felt bad about lying to him, but I didn’t think he’d appreciate that I was out fucking a bunch of strangers. He was very protective of me.
“Thanks Daddy,” I had said before hanging up that night. Jason said he liked it when I called him that. I liked it too. I knew it was wrong, but my crush on him had ballooned into full on burning desire. The attention he paid me lit a fire in my loins. I had rubbed on out more than a few times picturing my ‘Daddy’ drilling into me. Sometimes I’d pretend I was with him instead of my mom. I knew it was naughty, but I couldn’t help it; it just happened. Plus, it wasn’t like he was my real dad.
In any event, I was happy with my new job. Happy about the money and happy about the perks I got to enjoy along the way. As I walked to my car, relishing the tingle my ass checks still felt from David’s broad palm, I checked my messages to see if I had another client that day.
Sure enough, Susan had messaged me. I had another outcall later than night. Seven o’clock at the Sheridan Waterfront hotel, she wrote. Dress like a school girl, no panties. You’re booked for an hour at the usual rate. $300. He’s a new client, so treat him well.
Titillated, I drove home to shower and prepare for my next date. I’d have my whole degree paid for before I knew it.
CHAPTER TWO
Decked out in a sexy little Catholic schoolgirl outfit, complete with knee high socks, a pleated skirt, and a little white top with straining buttons which were barely holding things together. My bouncing cleavage was a sight to behold. It was a cool summer night and my nipples were erect and at attention. Every man I passed in the lobby stared gape-jawed as I made my way to the elevators and I felt a delicious heat radiate down to my bare pussy, exposed to the air under my skirt.
Up on the 15th floor, I found the right room and knocked confidently. I was looking forward to servicing this new client. It was a chance to get him hooked on me as a regular going forward.
I heard the occupant on the other side make his way to the door, so I leaned against the door frame, jutting my hip out and putting a sly little smile on my face, trying to look a sexy as possible for his first impression.
The door swung open and I said, “Hi, there. I’m Andrea, your date for–”
I froze, my voice trapped in my throat. My eyes almost popped out of their sockets.
Jason had answered the door. My stepfather had answered the door.
We stared at each other in absolute shock for what seemed like 30 solid seconds before I stammered, “What, uh… Jason, what are you doing here?”
“What am I doing here?” he replied. “What are you doing here?” He leaned out and looked left and right down the hotel hallway, checking to see if anyone was there. An older couple a few doors down was trying to get their key to work; the gentleman eyed me up and down in my naughty little get up as his wife struggled at the door. Jason grabbed my arm and pulled me into his room. “Jesus Christ, get in here,” he said under his breath.
It was a nice hotel suite with massive, plush king-sized bed, but I was slightly too stunned to appreciate it at the moment. Jason pulled me into the room, spun me around, and sat on the bed before backing up and running his hand down his face.
“Is this how you’ve been paying for school, Andrea?” he said, pacing back and forth a bit.
I watched him as he walked back and forth. Fuck he was gorgeous. He was shirtless, but had on a pair of pajama pants that looked incredible hanging on his rock hard body. He was going on about how dangerous and bad this was, but I was too distracted by his chiseled abs and broad shoulders to hear much of what he was saying. The muscles in his arms flexed and contracted under his skin as he
paced and the heat returned to my loins.
“…I mean, Andrea, I could have given you money if you told me you needed it,” he finished, throwing his hands up in the air to punctuate his last point.
I finally registered what he was saying. I looked up at him innocently and said, “But Daddy, my tuition is way more money than you think it is. It’s crazy expensive. Plus I wanted to make you proud. Proud that I was doing it on my own.”
I stopped suddenly. Why was I explaining myself? I was an adult; I could make my own decisions. Plus, hadn’t he just called for an escort in a schoolgirl’s uniform? I mean, he was married to my mom. It was pretty naughty, what he was doing.
“Wait a second,” I said. “Why am I being lectured? You’re the one who’s paying for sex here. What about mom?”
Jason scoffed and rolled his eyes, then looked at me and said, “Listen, I’m sorry to have to tell you this now, but your mother has left me. She’s been having an affair with her rich friend’s husband and they’re running off together.”
“Wow,” I said, not really that surprised. “What a bitch.” My mom wasn’t the most reliable or trust-worthy person in the world.
“It’s fine,” he shook his head. “It wasn’t really working anyway. It was just a matter of time until she left. Plus, I wanted to have kids the day we married and she promised me we would. But as time went on, she changed her tune. She said her mothering days were over.”
No shit, I thought. She wasn’t exactly mother of the year. Poor guy, my heart went out to him.
“I haven’t been happy. We haven’t had sex in months,” he said before turning to face me. “Hence my call to the Fox Den…” he trailed off and I felt his eyes on my body. My clit started to pulse along with the rhythm of my heartbeat, as he looked me over with his sexy, dark eyes. My breath quickened.
“And what’s with the schoolgirl request?” I asked as I stood up from the bed and trailed my hand over the outline of my nipple pressing against my top. He licked his lips and I saw his erection start pushing against the front of his pants. I didn’t let him answer. Instead, I said, “You wanted to pretend you were fucking me, didn’t you Daddy?”
I took a few slow steps towards him and watched as he started to breathe a little faster. “Were you going to make your escort call you ‘Daddy’, Daddy?” I said as I came to a stop in front of his strong frame.
I watched his cock twitch and jump in his pants each time I said ‘Daddy’. I could feel the wetness start spreading across my exposed pussy lips under my pleated skirt, the cool air from the hotel room sending shivers up my spine as it moved through my legs.
Jason’s breath hitched and he shivered as I ran my long, red fingernail through the tuft of course hair under his belly button all the way up his chest before coming to a stop at the base of his neck.
“Do you want to fuck your little girl, Daddy?” I purred at him feeling him quiver with arousal.
“I... I…” he stammered as I slowly got down on my knees in front of him.
“Yes, Daddy?” I said, running my fingers over his bulge, feeling the hard ridge of the head of his dick and caressing it gently.
“Uhhhh, fuck,” he said under his breath, his eyes rolling back in his head. “Fuck yes. God, I’ve wanted to fuck you for a long time,” he admitted.
“Mmmhmm, Daddy,” I said kneeling between his legs. “Then I think you deserve it.” I hooked my red fingernails around the waistband of his pants and pulled them down his strong legs. His massive cock bounced out in front of my face and my mouth immediately started watering. After all my masturbatory fantasies of Jason pummeling into me with his rock hard fuck stick, and here it was right in front of me.
My pussy contracted and pulsed as I took hold of the shaft in my hands and licked my red lips, moistening them before I pulled him toward me. I opened my mouth and took his head in, closing my lips around the bulbous mushroom cap and sucking at his smooth, warm skin. I licked and slurped him like a lollypop as I slid my fists down his shaft, lubricating it with my spit as I bobbed around at the tip.
Jason groaned out and grabbed my hair at the back of my head to push my face into his crotch. I opened my mouth wide and took his thick girth as far into my throat as I could manage. He pushed in and hit my soft palette with the head of his cock, making me gag and cough. He forced me to hold his dick deep in my mouth, and thick saliva ran down my chin as he grunted and jammed himself in.
My eyes were watering as I reached down and started fingering my clit. I was totally wet, my pussy lips swollen, red and engorged, desperate for attention. Years of fantasizing about Jason made me feel like I might implode with arousal now that his dick was pounding the back of my throat. He released my head and I popped off his cock to catch my breath. I liked it a little rough and I sensed this was about to get even more interesting.
“Mmm,” I said, looking up at him and running my tongue around my wet lips. “ I love sucking Daddy’s dick.”
I wiped my chin and mouth and jerked his shaft as I leaned in and sucked one of his balls into my mouth, rolling it around and tugging on it. He groaned out again and his dick surged in my hand. It was huge, at least 9-inches of hot, pink, veiny, deliciousness. I sucked his other ball into my mouth and breathed in his musky, male scent.
He gripped my hair again as I licked and sucked on his balls. He said, “Daddy is going to fuck the shit out of his little girl soon.” I moaned at his words and pumped his shaft faster and harder before taking him into my mouth again. I slid my lips down his cock and flicked my tongue under his head. Holding on to his hips, I bobbed my face into him over and over, tasting salty precum ooze out the little slit at the tip of his dick.
I stood slowly, pushing my tits into his chest as I got to my feet. He grasped my head in his hands and pulled me into him, shoving his tongue between my lips and kissing me deeply. I kissed him back and felt his hands frantically groping at my buttons. I gasped as he grabbed the sides of my shirt and yanked it apart, sending buttons flying across the room.
“Yes, Daddy!” I cried and he dove for my tits, pushed up high in my sexy black lace bra. He grabbed at me and squeezed, pinching my nipples through the lace, making me moan and push myself into him. I reached up and ripped my shirt of my arms, unclasped my bra and let it fall to the floor. My massive breasts bounced forth and he sucked a hard nipple into his mouth, lapping at me and kneading at my soft flesh.
“Fuck you taste so good,” he mumbled, rolling my nipple with his tongue before biting the tip and making me yelp out. “Daddy’s going to have to punish his little girl for being such a naughty little slut.”
He pushed me back towards the bed, groping my tits and probing my mouth with his tongue. He sat down and motioned for me to lie over his lap. “Daddy’s little girl needs a spanking,” he growled. “Get over here.”
I crawled over his lap and looked over my shoulder at him, biting my bottom lip. “Are you going to spank me hard, Daddy?” I said. “For getting fucked by so many men?”
He snarled at me and lifted the back of my skirt exposing my round, taut ass cheeks. “You’re mine to fuck,” he growled. “Only mine.” He raised his hand and slapped it down hard and fast. I screamed out as the delectable pain ricocheted through my body, my pussy throbbing and juicy.
“Again, Daddy!” I cried. He raised his hand a second time and smacked my ass with his massive palm. I cried out and he rubbed his hand in circles over the red handprint that had appeared on my white skin. I moaned as he caressed me, his fingers brushing over my pussy lips, feeling the slick wetness and probing at my aching opening. I arched my back, sticking my ass in the air and spreading myself open for him.
He slapped his hand down again, hard and sudden, rubbing at my stinging skin for a moment before plunging two of his fingers suddenly deep into my slit. I gasped at the shock and moaned in pleasure. My ass was tingling and I pushed into his hand feeling his fingers spread inside my juicy tunnel as he pumped his hand into me over and over.
“Oh fuck!” I mewed out. “That feels so fucking good!”
He was driving me closer and closer to orgasm as he jacked his hand roughly in my tight twat. Arching my back even deeper, I pushed my hips up, spreading myself open as much as I could over his lap. He withdrew his fingers and rubbed furiously over my dripping wet clit. My body was shaking and quivering under his touch and I felt his massive erection bump against my tits swaying beneath me. I was being driven wild.
“You’re not going to cum yet, little girl,” he said. “Daddy wants to feel how tight that asshole is first.” M
Oh god, I thought. I hadn’t tried anal before. But I was so turned on, I was practically vibrating with horniness. At this point, I’d probably let him put a coke bottle up my ass.
“Please don’t hurt me, Daddy,” I begged him through my sexed up eyes. I was nervous, but I wanted to feel him in my ass.
“Daddy owns that ass, doesn’t he” he said as he lifted me off his lap and put me on the all fours. “Daddy can do whatever he wants to it.”
“Yes, Daddy,” I mewed. On my hands and knees on the bed, I looked over my shoulder and watched Jason stroking his huge dick, staring at my wet cunt and tight little asshole. He was primal as he pumped at his shaft and licked his lips. I was desperate to feel him fill me up.
He spat on his palm and rubbed it into the head of his cock as he approached me. I gyrated my ass, moving it in small circles, tempting him. He reached forward and pressed at my asshole with his wet thumb, circled and rimming the edge, sending new sensations through my body. He ran his fingers down my snatch, getting his fingers coated in my juices before dragging them back up to my puckered little hole, all the while pumping at his cock with his other hand.
