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Sex Story

Entry Five

Dear Diary,

I've since gone on three more "jobs." Turns out, both Roger and Bill have alot of friends, mostly bored, married businessmen with alot of time and money.

I met a friend of Roger's tonight, his name was Keller. He's married, four kids in college and he just happens to own four of the most successful BMW dealerships in town.

Come to find out, my name was mentioned purely by accident.

Roger and Keller were having lunch when a beautiful waitress walked by and Keller remarked that he'd love to get a piece of that. Well, that's when Roger piped up and said that he knew someone twice as hot ..... me.

So, naturally, Keller began asking questions and Roger was not shy about giving the details of our hotel tryst. Afterwards, Keller was so turned on, he immediately asked for my phone number.

And now, you're up to speed.

I was watching music videos when the phone rang, it was Keller.

"Is this Roxy?" asked a man with a deep voice.

"Yes, this is Roxy, who is this?" I asked, turning the TV down and tossing the remote.

"My name's Keller, I'm a friend of Roger's," he answered.

I smiled, instantly remembering that night in the hotel.

"Yes, I know Roger," I said, trying not to sound stupid, "What can I do for you, Keller?"

"Well, Roger told me that you're the one I should contact about having some fun on the side. He also told me that you're very discreet," said Keller.

"Well, I believe discretion is important," I said, grabbing my soda from the coffee table, "I take it you're married, or in a relationship."

"I'm married," he said, almost in a whisper, "I'm also a very prominent man in the community and my reputation is extremely important to me."

"I understand," I said, quietly drinking my Pepsi, "So, ummm, where would you like to meet?"

"My wife is out of town, can you come over tonight?" he asked.

I didn't answer, at first, after all, I didn't want to come across as desperate.

"Yes, I can come over tonight, Keller, give me an hour to freshen up," I said.

"Great, I'm at 332 Elms Drive," he said, then politely hung up.

I hung up the black cordless phone and ran upstairs, eager to make more money. And, honestly, I was getting horny again. It had been almost a week since I had been with Roger.

After taking a short, hot bath, I emerged, completely coated with warm bubbles. I found this to be very sexy, but I restrained, knowing I would need all my energy for tonight. So, I quickly got dressed, sliding on black leather pants and a black leather halter top, and finishing off with a few sprays of my favorite perfume.

I found Keller's house pretty easy. Come to find out, he was only about 6 miles from my front door, talk about convenient!

He must have seen my headlights because he was already standing at the front door, nervously looking around to see if anyone saw me. I got out of my car and approached him, not saying a word or showing any emotion on my face.

Once inside, he took my jacket and seemed very pleased with my outfit.

"Wow, Roger said you were hot, but you exceed even my hottest fantasies," said Keller, tossing my jacket onto the couch.

"Thank you, Keller," I said, giving him a sly grin as I walked to the middle of the large living room.

"So, what kind of things do you do?" he asked.

"I can do anything you want," I said, "Whatever you need to get you off, baby."

"Well, I've always wondered what a vibrator in my ass would feel like," he said, seeming almost ashamed.

I smiled and walked towards him, sliding my arms around his waist and giving him a gentle kiss on his soft lips. I could feel his cock poking out behind his pants and this excited me.

"Do you have a vibrator, Keller?" I whispered.

"My wife has one in her dresser drawer," he whispered back.

"Well, how about you go get it and I'll get more comfortable," I suggested, looking up into his dark green eyes.

I couldn't help but giggle at his boyishness. How could such a savvy businessman be so embarrassed about something as minor as wanting your ass fucked with a vibrator. I mean, let's face it, many men enjoy this, it's no longer something that just women get off on anymore.

I slowly slid my fingers between the waistband of my leather pants and my washboard stomach, getting chills as the button popped loose and the zipper fell down.

I could feel my nipples already beginning to harden and my thong was quickly becoming wet. I kicked my pants off, but left my thong on. I reached up and unzipped my black leather halter top, instantly setting my large tits free.

My tan nipples were pointy and aching, begging for some attention. I tossed the top over on top of my pants, remaining in nothing but black stilletto heels and a black lace thong.

Minutes later, Keller emerged with the vibrator and a small bottle of body oil. His cheeks were red and his words were almost in a whisper as he complimented my tits.

"My wife used to have tits like that," he said, "But old age and four kids have destroyed them."

"I'll never let my tits become saggy or unattractive," I said, giving him a reassuring smile.

"Make them jiggle," he whispered, sitting down on the couch, "I like watching tits bounce."

Now, that was hot! He didn't want to get right into the sex, he wanted some old fashioned kinky foreplay.

He groaned and unzipped his dress pants, lifting his ass a bit and sliding them down to his knees.

His cock was pretty good size for a man his age. If I had to guess, I'd have to say it was, at least, nine inches.

He sat there, slowly stroking his fuck rod, watching my huge tits bounce up and down, occasionally slapping into each other.

"Yeah, that's it," he groaned, slowly bucking his hips, "Make them babies bounce for Daddy."

My pussy ached with his words. My nipples became hard as glass and my entire body was screaming to get fucked.

"I have a daughter your age," he whispered, stroking his cock a bit faster, "Her tits aren't as big, though."

I stopped bouncing and slowly dropped to my knees and crawled over to him. He watched my every move, occasionally groaning and whispering for me to come on and earn my money.

To my surprise, he did not want his cock sucked, he just liked seeing me down there near it.

"You ever fuck your Daddy?" he asked, "I bet you have."

I shook my head no and proceeded to tease his cock tip with my tongue anyway. His pre cum was extremely salty and instantly made me thirsty. His cock smelled of Old Spice, as he spread his legs wider.

"I'm gonna lay down and spread my legs," he said, "When I do, I want you to lube up that vibrator and shove it up my ass."

I don't know what it was, but something about that seemed so erotic to me. It was new and different and I was certainly getting off on it.

I watched him lay back and finish sliding his pants off, revealing his entire naked body to me.

"Fuck my ass," he whispered, spreading his legs as wide as he could.

I smiled and licked my lips seductively, then grabbed the bottle of body oil and coated the entire vibrator, making it both shiny and saturated.

I asked him if he was ready and he nodded his head yes and I went about doing as I was instructed.

At first, I was nervous, I had never done this before. But, as the first couple of inches slid into his asshole, I became more and more relaxed. He released his ass muscles, allowing me to finish driving the rest of the vibrator inside him.

"Rub my balls," he panted, "God, fucking rub my balls!!"

I quickly raised my hand and cupped his warm, tight ball sack, instantly gripping them and massaging them.

"Yeah, that's it, bitch," he groaned, "Ram that vibe in me!!"

So, like a good little slut, I obeyed and began fucking Keller's asshole with the thick, eight inch vibrator, watching his asshole open up more and more.

After a few minutes, I noticed Keller had become quiet, mostly just lying there bucking his hips.

"Keller? Are you okay?" I asked.

"If I give you another hundred dollars, will you do something for me?" he asked.

Another hundred? Fuck yeah!

"Of course, Keller, what is it?" I asked, still slowly working the wet vibrator in and out.

"Go in that middle drawer, over there in my desk, and pull out what you find," he said.

"Okay," I whispered, releasing the vibrator and slowly standing up, making my way to the large oak desk, in the corner.

I slid the drawer open to find another vibrator, only this one was attached to a harness.

Wow, this man was kinky!! I loved it!!!

"You ever use a strapon?" he asked, still lying on his back with his legs spread.

"No, but it doesn't look complicated," I answered, pulling the strapon from the drawer and walking back to Keller.

"Put it on and fuck me up the ass," he whispered, quickly flipping over onto his hands and knees.

I stood there, for a moment, admiring his sexy asshole and his firm ass, both unexpected for a man his age.

"Hurry up, bitch," he said, looking over his shoulder.

I took a deep breath and stepped into the harness, looking down and admiring my new found "cock."

"I want you to slap my ass and call me your slut," he whispered, slowly arching his back and thrusting his asshole backwards.

So, I obeyed and took my place behind him. I got on the couch, on my knees and placed my hands on his hips, gently pushing the tip of my "cock" to his rim.

"You want my cock, slut?" I asked, thrusting forward.

"Yes! Yes!" he moaned, "Make me your ass slut!!"

I smiled and pushed the head of my "cock" into Keller's asshole, instantly forcing it open. I leaned back and came back down, popping his right ass cheek. I smiled again, noticing the bright red hand print on his flesh.

He moaned and remarked on how good the sting felt, how it made his balls tighten up. So, I smacked his ass again, a bit harder this time.

I repeated the ass slaps all the while shoving my "cock" deeper and deeper into Keller's ass.

After I was satisfied that his ass had been branded, I again placed my hands on his hips and began fucking him, making him my bitch.

At first, I only gave him a few inches, wanting to tease him and see how much he could take. Then, when I was sure he was at the edge, I pulled out and slammed my "cock" inside him, burying my meat in his asshole.

I told him what a nasty slut he was and how good his asshole felt wrapped around my "cock." I complimented his gorgeous ass and huge dick, telling him over and over that he was now My Bitch.

He really seemed to enjoy that part. He would groan and beg me to fuck him harder, agreeing over and over that he was My Bitch, I owned his asshole, no one else.

I was getting off on this, all this control was mind numbing.

He began to rock his hips faster, begging me to make him cum. So, I instructed him to turn back over, back to his original position.

He quickly obeyed and returned to laying on his back.

"Spread your fucking legs," I moaned, pulling them apart before he could even blink, "Now, stroke that fat cock while I fuck the shit out of you."

He moaned again, and again, he begged me to make him cum. I leaned forward and grabbed onto the arm of the couch for leverage, and began fucking into his asshole like a jackhammer.

I could hear his ass juices slapping my "cock" each time I thrust into him and I knew he was close.

"Yeah, that's it, you little slut, cum for me, cum all over my "cock," I chanted, over and over, pounding into his asshole.

My pussy was wetter then ever and I needed to cum, so I figured, make him cum first then hopefully he'll make me cum.

"You little slut!!" I yelled, "Fucking cum!!!! What the fuck do I have to do? Rip your goddamn asshole in half?"

"Oh, GOD!!!" he screamed, "Rip my asshole!!! Rip my asshole!!!"

I pounded into his ass so hard my tits were becoming sore from slamming into each other, but I never gave up. I just kept on fucking Keller's ass until he finally could take no more. He tensed up and arched his back, throwing his legs apart and screaming, "FUUUUUUUUUUCK!!!! OH, SHIT, TAKE THAT, BITCH, TAKE IT!!!! ALL OVER YOUR FUCKING TITS!!!!!"

Rope, after gooey rope, shot up onto my tits and nipples, spraying all over my stomach and even making it to my lips. I just kept on fucking him right through his orgasm, knowing this would make it more intense.

Finally, after a few minutes of showering me with his seed, Keller came to his senses. He caught his breath and thanked me for fucking him so good.

"I bet you need to get off now, huh, baby?" he asked, slowly sitting up on the couch.

I gently pulled my "cock" from his ass and slid the harness off me.

"Lay down on the floor and I'll suck that sexy pussy for you," he whispered, motioning for me to lay down at the foot of the couch.

I obeyed and quickly dropped to the floor, instantly spreading my legs.

"That's a sexy pussy you got there," he whispered, hovering over me, "Reminds me of my daughter's cunt."

"You've seen your daughter's pussy?" I asked.

"Many times," he said, "Many, many times. I used to pay her to let me watch her shower."

This too, was very sexy and erotic to me. Was I losing it?

"I never fucked her," he said, "But, she did let me finger her and make her cum a few times."

"Mmmm, I love being fingered," I moaned, reaching up and playing with my big tits.

"She was always such a good slut for Daddy," he said, lowering his mouth to my aching pussy, "Always ready to please and be pleased."

I closed my eyes and imagined Keller in the bathroom with his daughter. I imagined her sitting on the toilet, legs totally spread and his fingers buried inside her cunt. This image only made my cunt drool that much more.

Keller's breath was hot on my swollen pussy, almost melting my oversized clit. His tongue was ruthless, lashing against both my clit and my fat pussy lips. I arched my back and groaned, over and over, knowing I would not be able to hold off for very long.

He slammed two fingers inside my dry asshole, instantly sending me into another zone, completely unaware of my surroundings.

Something about having a man, old enough to be my grandfather, fingering me and eating my pussy was very very hot. I had always loved older men, but I had never had one as old as Keller.

My mind drifted away as I became more and more lost in the sensations that were flooding my pussy. I had never had my cunt eaten out so good. He left no spot unlicked. His tongue danced over my clit, sucking it into his mouth and gently biting it with his razor sharp teeth.

I bucked my hips and began riding his face. My nipples were at full attention and my ass had begun to loosen. My pussy was flooding and my mind was jello.

"Oh, God, Kellerrrrrrrr!!!" I screamed, "Oh, fuuuuuuck!!!! I'm gonna cum!!! I'm gonna cum!!!!"

Keller kept on, never faltering. His tongue and fingers worked together like a well oiled machine. One pumping me and the other licking the skin right off my pussy.

I chanted and moaned, panted and screamed, finally reaching the hardest orgasm I'd ever had.

My mind went totally blank and the room was spinning in three different directions. My eyes rolled into my head and my mouth fell open, gaping and panting, struggling not to die of complete and total extasy.

Finally, several minutes later, I was able to breathe and focus again. I watched Keller get up and wipe his mouth clean. He stood over me, wallet in hand, and tossed two one hundred dollar bills beside me.

"That was the best sex I've had in years," he said, extending his hand to help me up off the floor.

"Thank you, Keller," I said, trying to stand without swaying or falling.

"I'll definitely give you a good recommendation," he said, smiling and excusing himself to go take a shower.

Now, normally I would have stayed and showered with him, but that was extra, and considering he had already put his wallet away, I figured our night was finished.

So, I slowly got dressed and quietly left Keller's house, careful to not be seen.

Now, I am home, freshly showered and feeling great. I have now accumulated close to a thousand dollars, not a bad way to make a living.

Who knows, if I keep this up, I might just be able to finance those dreams I've always had.

Love, Roxy