Picking a New Sugar Baby Pt. 01 – Anal – Free Sex Story

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I was sitting at my desk, my office door was closed, and I was on the phone with my Wife. There was a knock at the door. “Hey, darlin’, my 9:30 appointment is here. I’ll see you later. I Love you too,” I told her before hanging up and turning my attention to the door.

“Come in,” I called out.

I started looking for the file on my desk with the woman’s information, finding it just as the door shut. I looked up and was surprised to see the young woman was wearing a skimpy schoolgirl-style outfit. Her skirt was short, and it came down about halfway between her waist and knees. She was wearing thigh-high black stockings that were attached to a garter belt. She wore a white button-up sweater that was opened to reveal a tight, almost see-through, white t-shirt. Beth’s long blonde hair was in pigtails. An average-sized purse hung on her shoulder, and a pair of black fuck-me-pumps made by the same designer as her purse completed her outfit.

“Uh… you must be Beth,” I said, and it came out more as a question than a statement. To say that I was surprised would be an understatement.

“Yeah, sorry I’m late,” Beth replied.

“You’re not late. Have a seat,” I told Beth, looking back down at my desk.

Instead of sitting in the chair across from my desk, she came around the desk beside me. She faced the desk, putting her hands down on it and arching her back, which caused her skirt to rise a little, exposing the bottom of her Ass cheeks. I couldn’t help but look.

“Grab it. You know you want to,” Beth said quietly.

“I can’t. I’m married,” I told Beth, still staring at her sexy Ass.

“I know. Your Wife is the one that told me I should dress like this,” she replied, wiggling sexy her Ass. “So, go ahead. Grab it.”

“Wait. Hayley sent you?” I asked.

“Yeah. she said if I let you fuck me like a whore I’d get the job,” Beth replied.

“She said that, huh?” I asked, reaching up and grabbing an Ass cheek. “How old are you?”

Beth didn’t answer. I rubbed her Ass softly, going up to her waist. I wasn’t very surprised to find out she wasn’t wearing panties. I brought my hand back down to the top of her stockings and slid it between her legs, slowly going up. Beth let out a soft moan as my finger lightly brushed the folds of her outer labia. A second later, I had a finger between her Pussy lips. The slut was already wet. I moved my hand along the lips of her Pussy gently. She let out another quiet gasp and then said, “I’m 19.”

“So, you wanna get fucked like a whore, huh?” I asked, taking my hand away from her.

“What I want is the job,” answered Beth. “And I don’t mind using my body to get it,” she continued, wiggling her Ass playfully.

“What about using your body to keep the job?” I asked her.

“Is that part of the job?” Beth asked.

“It is for you,” I told her.

“You want me to be that kind of secretary, huh?” Beth asked coyly as she turned around and leaned back on my desk.

“What exactly do you expect to get out of this job?” I asked her.

“I need money to pay my bills. I need to find a new place to live. I need healthcare,” she replied.

“You want to be a secretary or a sugar-baby?” I asked her.

“What are you offering?” she asked, folding her arms across her chest.

“I’ll give you an allowance, I’ll pay your doctor’s bills, and you can stay at my house by the coast. In return, you only fuck me. When I want, where I want, how I want,” I told her.

“How much of an allowance?” She asked.

“Secretary starts at $38,000 a year, and Sugar-baby pays $52,000. Do a good job, and you’ll get a raise,” I told her.

“So, you’re going to give me a place to live, pay my bills, including doctors, and pay me $1000 a week to be you’re little whore? What is Hayley going to say about all of this?” she asked.

“First off, I said I’d pay your doctor’s bills, not all of your bills. And second, you know Hayley doesn’t care,” I told her. “So, are you interested?”

“I’m intrigued,” she replied, eyeing me thoughtfully. “You’re not into any weird shit, are you? Oh, and I don’t take it in the Ass.”

I laughed. “It depends on what you call weird,” I told her. “But you don’t have to worry about that. Between Hayley and Arianna, I have all of the weird I can handle at home.”

Beth laughed too. “I bet those two keep you on your toes. Ok, well, if you just want to fuck, then yeah, I’m in. When do I start?” she asked.

“Start? You haven’t made it past the interview yet,” I said, reaching down and unbuttoning my pants.

“What do you mean? I thought we just worked out all of the details,” Beth replied.

“You don’t think I’m going to pay you that much without testing you out first, do you? How do I know that Pussy hasn’t been wrecked by a mile of cock? Or that you even know how to use it?” I asked her as I started to unbutton my shirt.

Beth stood up, grabbed the hem of her skirt, and slowly pulled it up. She was about to straddle my lap. I stopped her before she got too close and before her skirt was high enough for me to get a glimpse of her Pussy. “Oh no, you’re not getting off that easy. Get on your knees, whore,” I told her.

Beth froze, looking at me with a slightly shocked expression. “But I thought you wanted to test my Pussy?” she asked.

“I want to test your mouth too. Now get on your fucking knees, whore,” I replied after a moment. “Don’t make me tell you again.”

Beth finally moved, first by letting her skirt fall back into place. Then, she slowly got down on her knees in front of me. The expression on her face didn’t change much. “Take off those shirts. Let me see your tits,” I told her.

Beth began to take her shirts off. “Are you going to keep talking to me like that?” she asked shyly.

I leaned forward and put a hand on her cheek, raising her head so that she was looking at me. “Are you offended?” I asked.

“A little,” she replied softly, trying to look away.

“Beth,” I said, “you’re about to fuck me for money. You’re a whore now. When we aren’t fucking, I’ll treat you with a little more respect. But you need to get it through your head now. While I’m fucking you, you’re nothing but a whore. If you can’t accept that, get up and leave.”

“You’re right. I’ll be ok,” Beth replied as she took her second shirt off.

“Good. Once your tits are out, suck my cock, whore,” I told her, leaning back in my chair.

Once her shirt was off, she crawled the rest of the way to me. She wasn’t wearing a bra as I had thought, and now her young, teenage tits were fully exposed. They were adorable, perky C-cups. I reached down and grabbed one as she got into position between my legs, giving it a couple of good squeezes. Her tit was very firm. I pinched her rock-hard nipple before putting my arms back on the armrests of my chair. Beth put one hand on my leg and used her other hand to fish out my semi-erect cock out of the fly of my boxers. “Holy shit!” she said, looking up at me in disbelief. “This thing is fucking huge!”

“You’re not a virgin, are you?” I asked her.

“Well, no… but…” she started to say.

“Too bad,” I said, cutting her off. “I would have paid you a sign-on bonus of $10,000 if you were.”

Beth’s hand was still loosely gripping my cock. “Are you serious?” she asked.

“Yeah, of course,” I told her.

“What if I knew a girl that would be willing to let you take her virginity for, say, $5,000? Would you give me the other $5,000?” she asked.

I had to laugh at her. “So, what, now you’re a pimp, and you want to turn your friends into whores too?” I asked, holding back laughter.

Beth just stared up at me for a moment, not saying anything. “Let’s see if you get the job first,” I told her. “So far, you’re a pretty shitty whore. I told you to suck my cock, and I’m softer now than when you started.”

She leaned forward and took the head of my cock into her mouth, just past her lips. She looked up at me as if she was seeking my approval. Beth had one hand on my shaft, and the other disappeared between her legs. Her tongue was tickling my foreskin, and I was beginning to get hard in her mouth. “I like the way you look with my cock in your mouth,” I told her, looking down at her.

Beth slowly went down my shaft, all the way to the base of my cock. I could feel my dickhead in her throat. Beth’s eyes never left mine until her forehead was flat against my stomach. She held her head there for an impressive amount of time. “You like sucking cock, don’t you, whore?” I asked her.

She tried to nod and hummed, “Mmm-hmm….”

By now, my cock was starting to throb. Beth started to ease back off my prick, going just as slow as when she had gone down. “Alright, bitch, stand up. Let me see if your Pussy is worth paying for,” I told her.

Beth slid my cock out of her mouth with a quick pop. She didn’t say a word as she stood up then turned around. Beth bent over a little and looked back at me, lowering herself onto my lap. She had to adjust her shirt a little, then my cock was next to her Pussy. There was an intense heat coming off her. Beth wasted no time. She raised up, and I felt her hand on the underside of my cock. An instant later, the tip of my prick was barely inside her cunt. She lowered herself onto my cock slowly. “Goddamn, you’re fucking tight,” I muttered.

“Mmm… yeah, you feel so good inside me,” Beth managed to get out between sharp breaths.

Beth put her hands on her neck, and the back of her head, then started grinding on me slowly. It took her a couple of minutes, but she began moving her hips more once she had adjusted to my size. “Let me know when you’re gonna cum. I’m not on birth control,” she whispered.

As soon as the words were out of my mouth, Beth started working my cock like a real pro. I was impressed. She would go up the length of my shaft until it felt like I was going to come out of her, then ease back down on me at the perfect speed. The entire time she wiggled her hips as if she were hula hooping. I knew I wasn’t going to last very long. Her tight little cunt felt too good. I was right. Not two minutes after she started working her Pussy on me, I was on edge. I grabbed her hips and pulled her down on me as fast and as hard as I could. “Is my Pussy too much for you?” Beth asked, laughing a little.

I ignored her. She was still moving her hips a little, as much as could with me holding her. I moved my hand between her legs and found her clit. Beth started moaning. I ran my other hand up her body, between her tits, to her neck, and gripped it tight. Once I had a good grip on her, I pulled her to me as close as possible. She let her head fall beside mine. “You feel so fucking good. I’m going to cum in your Pussy,” I whispered in her ear before biting it gently.

“No!” Beth screamed as she tried to stand up. “Let me up! Cum on me!”

I tightened my grip on her, squeezing her neck, and pushed down on her pelvis. She couldn’t move. Just as I started pumping cum inside of her tight vaginal canal, I whispered in her ear again, “I always cum inside my whores.”

Beth quit struggling and just laid back on me. “So, I’m your whore now?” she asked.

“With a Pussy like that? Absolutely!” I told her, then kissed her neck, still holding her against me. I rubbed her Pussy lips with the hand I had between her legs. I could not believe how wet she was.

Beth was enjoying the attention I was giving her Pussy. Her breathing had become staggered. Between breaths, she asked, “What if I get pregnant?”

“Then you’ll move in with Hayley, Arianna, and me,” I told her, letting go of her. “Now, stand up, whore.”

She stood up slowly. Her skirt fell back down around her, covering her Ass. I turned back to my desk and started to clear it off. “What if I get pregnant, and I don’t want to live with all of you?” she asked.

“We’ll talk about it if it ever happens. Now, take your skirt off,” I told her.

When I turned back around to face Beth, she was just standing there looking at me. Her skirt had fallen to the floor around her feet. She looked sexy as hell with her shirt opened just enough to expose her nipples and essentially naked from the waist down. I was surprised my cum wasn’t leaking out of her. “Hop up on my desk,” I told her.

Beth kicked her skirt away from her feet and moved to the desk, sitting on the edge. I rolled my chair closer to her, getting between her legs. She put her feet in the chair beside my hips. I could tell she wasn’t quite sure what to do. “Just relax,” I told her. “Do you like having your Pussy eaten?”

“Um… yeah… but…,” she said quietly.

“Good, get comfortable. Lay back on the desk if you want,” I told Beth, leaning down between her legs.

Beth’s Pussy was beautiful. This was the first good look I’d gotten of it. Her inner lips were a sexy shade of dark pink and slightly longer than her labia majora. They were spread a little, their shape was nearly perfect. My cum was just starting to show in her little round Pussy-hole. Beth’s Pussy-hole wasn’t as big around as my pinky. I couldn’t believe my cock had fit inside of her so easily. Now I understood why she was so tight. She had a cute clit, too, peeking out of its hiding place. Her clit was the size of a small pebble, and just as hard, it was a darker color than the rest of her Pussy. Without a doubt, she had one of the sexiest pussies I had ever seen, right behind Hayley and Arianna. Just as I was about to put my mouth on her clit the intoxicating scent of her Pussy hit me. It was a mixture of us, slightly sweet-smelling with a hint of musk. I liked the way our Sex smelled. If she tasted half as good as she smelled, I was going to thoroughly enjoy eating her sloppy Pussy. As I touched my tongue to her clit Beth gasped slightly. “You don’t have to do that,” she said.

I kept my mouth as close to her as I could as I looked up at her. “Do you not want me to?” I asked.

“No. I want you to. I just know that guys don’t really like doing that,” she replied.

“Trust me. I Love eating Pussy,” I told her. “Did you cum while you were on my cock?”

“No.”

“Do you want to cum?” I asked her.

“Well, yeah, of course, I do, but…,” she started saying.

“Then shut the fuck up and let me eat your Pussy,” I said.

I put my lips on her clit before she had a chance to say anything else. Beth moved her legs to my shoulders. She used her heels to pull me to her. I sucked her cute little clit between my lips, flicking it with my tongue. Beth started making a lot of noise, which only encouraged me more. I took my hands and put them under her legs. I started pushing them up. Beth got the idea and laid back on the desk. I lifted her legs in the air then spread them further apart. Now I had better access to her Pussy. I moved down to her Pussy lips, licking down the edge of one with the tip of my tongue, then back up the other. Beth’s moans were getting high-pitched and whining sounding. Beth’s legs were starting to shake a little, and my cum began leaking out of her, down to her sexy little asshole. I used my tongue to lick it off her, then sucked a little more out of her. I stood up and leaned over her. “Open your mouth, whore,” I told her.

Beth looked up at me and opened her mouth. I leaned over Beth, about three feet from her mouth, and let the cum from my mouth fall into hers. Beth swallowed as soon as it was all in her mouth. “Good girl,” I told her.

Beth was reaching for my cock as I went to sit down again. “Fuck me again,” she pleaded.

“I will. My cock isn’t hard yet, and I’m not done eating your creamy Pussy,” I said.

I sat back down and got into the same position before. This time I dove right into her Pussy. I used my tongue to part her Pussy lips and began o lick all around, nice and slow. I worked the middle two fingers of my left hand into her. Beth felt tight around my fingers too. I had more of my cum out of her Pussy and in my mouth in no time at all. I eased my fingers out of her and stood up again. This time Beth anticipated what to do and opened her mouth. Instead of letting my cum drip in her mouth like before, I spit it onto her face, covering her nose and cheeks. “What the fuck, asshole?!” she hissed.

I slapped her across her cheek. “You better learn your place, whore,” I told her sternly.

Beth just looked up at me in shock. Finally, she said, “Yes, sir.”

By now, my cock was half-hard again. Spitting on Beth then slapping her had helped a little. I grabbed my cock and laid it between her Pussy lips. I used my foreskin to rub her clit. “Oh, god, yes! Fuck me!” Beth screamed.

“Not yet,” I told her, leaning over her.

I got face to face with her, then started to lick my cum off her face. Once I had gotten everything, I kissed her. Our tongues met, and she seemed to be trying to get all of my cum out of my mouth. Beth wrapped her arms around me and held me tightly. The kiss seemed to go on and on, with both of us grinding on the other. Her Hot, wet Pussy felt amazing on the bottom of my cock, which was rock hard and throbbing again. Beth pulled away from our kiss and looked up at me. “You’re hard again. Please, fuck me. Make me cum with your cock,” she begged.

“Not yet,” I told her, sitting back down.

I buried my face between Beth’s legs again, wasting no time getting my tongue as deep as I could in her Pussy. She started bucking her hips, trying to grind her dripping cunt on my face. “Please…,” she pleaded. “I need your cock in me.”

I ignored her and eased my fingers inside her. I curled them up to apply some pressure to her g-spot, then moved my tongue to her clit. I sucked on her clit while applying varying pressure to her g-spot. Beth grabbed my head, pulling my hair, trying to separate my mouth from her cunt. “Oh, god! Fuck me!” she screamed. “I’m gonna fucking cum! Please, let me cum on your cock.”

I didn’t stop teasing her clit. Now I was flicking it lightly with my tongue. I was still fingering her Pussy, trying to get my fingers as deep in her as possible. “Oh, fuck! I’m Cumming!” Beth screamed again, this time probably as loud as she possibly could, as she pulled my hair even harder.

Suddenly Beth let go of my hair, got stiff, and let out a long, loud, moaning cry. A clear liquid flooded out of her Pussy. I caught a lot of it in my mouth; still, some ended up in my lap and on the floor. I swallowed as much as I could, then moved away from her and looked up her body at her. Beth had her head laid back on my desk. Her hands were squeezing her tits. “What the hell was that?” I asked.

Beth just laid there for a moment, out of breath. I just sat there looking up at her. Finally, she sat up enough to look at me. “I’m a gusher,” she said. “I was hoping I could hide it from you for a while. Some guys don’t like that.”

“I like it. Don’t be shy around me. Ok?” I told her.

“Yeah, ok. I’ll try,” Beth replied.

“Do you still want me to fuck you?” I asked, standing up, my cock in my hand.

Beth laughed. “Do I really have a choice?” she asked.

“Of course, you don’t. You’re nothing more than my whore right now,” I told her.

I put the head of my prick between her Pussy lips. Beth tried to scoot closer to me. Before she could move very much, I grabbed her hips and drove my cock into her fast and hard. Beth gasped sharply. I moved my hands from her hips down to her legs and raised them up. Now that I had a good grip on her, I started fucking her hard and fast. I wanted to hurt her Pussy with my cock. Beth’s moans got louder and louder, eventually turning into quiet cries of “Oh, god,” and “fuck me.”

I continued fucking her hard. Beth’s tits were bouncing around wildly, which only made me want to fuck her harder. Out of nowhere, she screamed out, “Oh, god, I’m fucking Cumming!”

I didn’t let up. I kept fucking her hard. I noticed there were little streams of her cum shooting out of her Pussy all around my dick when I would thrust into her. I let go of her legs and pulled out of her. No sooner than my cock was out of her, Beth’s cum flooded out and splashed on the floor. Her Pussy lips were quivering, and everything was extremely wet. Her cum was still dripping out of her, leaking down over her asshole and onto my desk. “Stand up, whore,” I told her as I backed up to give her room.

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