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This story is the first in the”Sugarbaby Chronicles.” These are works of fiction. Any persons or events depicted here are imaginary and exist only in the Author’s mind. These stories will tell the tales of a number of women and men who enter into fictional adult consensual arrangements. The Author intends for each story to stand on its own, however, characters in one story may find their way into other stories depending on reader reactions and requests. Input, voting and comments are very highly valued and encouraged by the author.
Author’s Note: I see this story, Ch. 01 in the Sugarbaby Chronicles, as more of an overview. I began writing it with Angela as the central character. I think it morphed into a story about Mary and Dan with Angela as the “hook” to tell the story. Let me know if you like it.
Ashley sat in her dorm room lamenting her situation. She needed to cough up her share of the deposit for the Spring break trip and she flat out didn’t have the money. She was counting on Christmas money from her parents and grandparents. Santa wasn’t so generous to her this year.
Money was tight for everyone, including the fairly affluent Henderson family. Even if the 20-year-old Ashley had the $500 she had no idea where the rest of the money for a week at S. Padre Island would materialize.
Ashley didn’t want to piss of her girlfriends by backing out of the trip and spending the mid-March week at home or alone in the dorm. The sun, the non-stop partying, the cute boys, and dancing her pretty little ass off all night didn’t look like it was going to happen.
Somehow thought her plight just wasn’t fair. She thought shedeservedto go on Spring break. She felt cheated. Ashley had never held a real job, and her work experience consisted of occasional baby-sitting gigs that served as more or less favors to family friends than a source of income.
Mary Wilson listened to her sorority sister’ plight later that evening when Ashley dropped by her apartment to officially deliver her news about dropping out of the trip. Mary was a senior on a full-ride volleyball scholarship. Mary unfurled her long, athletic legs and stretched, pondering if Ashley was the kind of girl whose plight she might be able to remedy. She giggled to herself regarding how easy it would be for her to come up with the money.
Mary was a party girl, a B student, and social butterfly extraordinaire. She was always organizing parties at the pool located just outside her apartment, weekend adventures to the various clubs and concerts, and generally the one who everyone gravitated towards to have a good time. Mary was also somewhat of an enigma to her sorority and friends. She clearly came from a modest background but managed to live in her own apartment, dressed well, and always had money for partying. Mary, to anyone’s knowledge, had never had a serious boyfriend, and that gave rise to the sterotype of a gay female athlete, even though she was known to occasionally fuck her date to some Zeta party.
Mary told Ashley not to be so sure about cancelling if she was serious about exploring avenues to come up with the cash.
“Look, let me think about it. I might have an idea,” said Mary. Ashley eyebrows shot up in alarm and a degree of intrigue. She coolly told Mary she wasn’t sure liked the sound of whatever it was being considered.
“Whatever. If you want to go I said I might know a way. It isn’t something dangerous, but different. Let me think about it and do some checking,” said Mary.
The next afternoon Dan’s cell phone signaled him a text had come in from Mary, and he excused himself for a moment from his lunch meeting.
“hi Daddy! call asap idea 4 u” read the text.
Dan’s cock stirred as he recalled when two nights ago when Mary straddled him on the expensive leather couch he bought her. He recalled how she offered her 34 DD breasts to him and told him how good Daddy’s cock felt in her hot, tight blonde pussy. Mary could and would fuck for hours, and her desire to please him in every way seemed boundless.
Mary was Dan’s Sugarbaby. They had been together for about two years. It was an arrangement that suited both of them well. Like all relationships it had evolved over time. Dan was divorced, professionally driven and traveled quite a bit. He had neither the time nor interest in a traditional romance. He had a thing for women almost half his age, but what middle-aged man didn’t at least fantasize about sexual attention from a hot college aged girl? Dan just had the means and attitude to make it happen.
Mary was still Dan’s fantasy girl. Mary was his ideal Sugarbaby, and she worked hard to make sure she fit the bill. Physically, she was right out of his long ago teenage wet dreams. Mary stood 5’10 with long blonde hair and a little matching landing strip of pubic hair. She was certainly tone, fit, and flexible. Mary kept a year-around deep tan. Her nails were always perfect. Her beautiful Germanic heritage canlı bahis face featured sparkling white teeth and bright blue eyes.
Once Dan had given Mary a taste of what was possible she became a very willing student. Her prior sexual experience had been the occasional fumbling sex with a few boys, but Dan brought out in her a willingness to try almost anything. She eagerly took instruction on how he liked her to suck his cock. He stilled shuddered when he remembered how she so willingly stuck her taught, virgin ass up in the air to him when he told her she need to learn about ass fucking, and how she urged him not to stop even if it did hurt.
“Hey baby, what’s up?” asked Dan.
“Daddy! Hi! I know you are busy.”
“Oh, just the usual. I’m looking forward to the weekend, sexy girl.”
“Me too! Hey, listen, I have a friend who might be interested in an arrangement if you know any guys looking. She hasn’t done this before and doesn’t know I am checking it out for her. Is that ok?”
“She a good friend?”
“Sorority sister who needs a Daddy. Well, she needs some support. I think she also needs a Daddy.”
“Baby, I told you to be real careful about friends. It’s your call. I don’t have any skin in the game. You do. Could be embarrassing if word got out.”
“I know, Daddy. I know. I am soooo under the radar. I think she would be, too. Something just tells me…I want to bring it up to her. Maybe you could meet her Friday? I don’t want her on those yucky websites.”
“If you want to chance it, yeah, I know a couple of the guys are looking. Mary, you know how this works. I’m not promising anything and I am not going to pimp. I want you to really think that through. See you Friday about 8.”
Mary invited Ashley over to her apartment the next evening. They chatted over a few beers until Mary brought up the trip.
“Hey, you sure you can’t get the money together? This is going to be a fuckin’ epic trip,” asked Mary.
A very dejected Ashley said she didn’t see how. Even if she could find a job slinging pizza part time or working at the mall there wasn’t enough time. In fact, it looked like her entire social calendar for the semester was shot, other than hanging out at the bars and hoping for free drinks or some random boy asking her to a party.
“Well, I don’t have do that shit,” said Mary. “I don’t work. I have money. It’s fun and easy as shit if you can be cool.”
Ashley eyed her cautiously. “Yeah, I sort of noticed that about you. I mean, you have a cool place here. You always buy what you want, tan, your nails done. Are you blowing your student aid money? Dealing drugs? Are you…are you a tit bar dancer? “
The acquisitions hung in the air as the two girls judged each other.
“No. I have a Sugar Daddy,” Mary answered. “I have an arrangement with a guy, an older guy, who is really sweet to me.”
Ashley was astounded at the news. Sugardaddy? Older guy? Arrangement? Thoughts flew threw her mind. However, Ashley wasn’t appalled; she was intrigued.
“Sugardaddy? Like a guy who gives you money,” asked Ashley. “How doesthatwork?’
“It’s pretty simple,” explained Mary. “We spend time together like a real couple. We go out sometimes, except we just don’t go out around friends. We keep it kind of on the down low. We really like each other a lot. He helps me pay my bills so I have time to spend with him. He wants me to be comfortable, too. He is sooooo sweet!”
A blush spread across her face and she couldn’t meet Mary’s eyes. “Do you, like, you know…like…does he make you have sex with him?”
Mary smiled very brightly and replied, “No, Ashley. He doesn’t make me have sex with him.”
“He fucks the daylights out of me,” Mary exclaimed.
She wondered if it really could be that simple. Sex with an older guy that doesn’t creep you out and you get to live large off his dime? Really?
Ashley weighed it as she got up from the couch and went to get another beer from Mary’s refrigerator. Well, fucking the occasional penniless stud in a dorm room wasn’t getting her anywhere, thought Ashley. How much can an older guy get it up? I bet it isn’t that much sex. Just pretend it’s hot the few times it happens, right? I could do that.
“Ok. So, like, how do you find one?” said Ashley.
“The first step is to come back over here around 7 Friday night,” said Mary.
Dan guided the black Lexus LS 460 out of the parking garage and on to the nearly deserted downtown streets. One great aspect of living in Austin were late January evenings like now when it was warm enough to slide open the sunroof. Winter ended soon in Austin. Only an occasional cold snap would punctuate the weather’s relentless march towards the crushing summer heat.
As he drove Dan thought about the looming end of his arrangement with Mary. She was a great girl. Mary set the Sugarbaby Gold Standard for Dan. Mary was a senior and would graduate in June. His arrangement with her was due to end 90-days after she walked bahis siteleri those long, lovely legs across the stage. Dan knew Mary would have no problems finding her first post-undergraduate job. Would she remain in Austin? Take a job in another town? And if she did stay, how would they handle that?
Dan didn’t want a real relationship with Mary. He had been married 23-years before divorcing his wife when he was 44. Now at age 52, he remained committed to never marrying again or even cohabiting with another woman. He never felt really free until he divorced, and he cherished his liberty. Besides, taking up full time with a 23-year-old hottie seemed such a pathetic cliché. Not that Dan ever entertained the thought she would want to settle down with him. He liked their arrangement.
Sure, the arrangement had certainly changed over the past two years, mused Dan. It evolved as they evolved, and neither party ever pressured by the other regarding when or how to change the specifics. It felt comfortable to both of them. The Sugardaddy role suited Dan perfectly, and Mary said she relished her role as his Sugarbaby.
The light turned green and Dan eased the big sedan up Enfield Drive. He wondered if Mary’s sudden interest in introducing her friend to the life had something to with finding him a suitable replacement come June. He knew she cared for him, and Mary no doubt knew he would find another young lady to spoil. Maybe she thinks if she picks her replacement she’ll know he’s safe and in good hands. He chuckled at that thought. If Mary knew him then she should know he fucking well made his own decisions.
So, then, who was this friend of Mary’s? Mary asked if Ashley could be at her apartment when he arrived so he could meet her.
“It will only be for a little bit, Daddy. I promise. It won’t interfere,” Mary had cooed sexily on the phone. “I want you to meet her and see if she might be right for some one you know who is looking. I know one of those horn dogs must be looking.”
Dan was a member of a very loose affiliation of men in town who enjoyed keep a Sugarbaby. It wasn’t a club. They met once a month or so for lunch or dinner at one of the upscale gentlemen’s club in town and the occasional social get together. A few of the guys brought along a woman to these gatherings who were interested in becoming a Sugarbaby, or at least exploring the idea of a short- term arrangement. Arrangements came and went and there was always a few who needed to interview or audition prospects. It was an “on your honor” type thing; you were responsible for the conduct and discretion of the women you introduced to the group. One too many bad calls and you stopped receiving invitations to the gatherings. If you were a man of means and looking for something long or short term, then this was an affiliation you didn’t want to be cast out of.
Dan smiled as his train of thought changed. Mary was an adventuresome girl and loved to surprise her Daddy. Maybe Ashley was another surprise three-way she had planned—which means Mary needed an extra reward for good behavior, grinned Dan. He laughed out loud as he wondered what it was Mary wanted. He found it hard to say no, but he always rewarded good behavior and never punished bad behavior, other than to express his disappointment. That was all it really took for a Sugarbaby to get the message.
“Mary, Mary, Never Contrary, how your wicked garden grows,” Dan thought, as he drove on towards Mary’s Northwest Hills apartment.
Mary was beginning to grow irritated. “Look, just be cool? Ok? He’s a really nice guy and he said it’s ok for you to be here,” Mary yelled at Ashley from the bathroom. “Daddy will be here in a few and I gotta’ finish getting ready. Chill already.”
Ashley stood at Mary’s bedroom door and was asking question after question about her mystery man and how the whole thing worked. Mary explained it was up to Daddy to tell her if he decided to tell her anything at all. “Look, it’s Daddy’s rules, ok? My Daddy tells me the rules upfront and I decide if I can hang with it. He said he would explain if you’re cool enough to do this. So act cool! Be cool! Ashley, just be your self. If I didn’t think this was a good idea for you I would never have even mentioned this to you.”
Mary walked out of the bathroom and Ashley eyes flew open wide. “Oh my God!” she gasped.
Mary was dressed to meet her Daddy for some behind closed doors time. She wore a sheer, see-through white baby doll negligee and matching panties from Victoria’s Secret. Her hair and make up were perfect and her nails painted bright red. She smelled heavily, but not offensively, of Coco Channel Mademoiselle and her skin glistened from freshly applied moisturizer. Mary went to her closet and pulled out a brand new pair of impossibly tall white Italian leather stilettos.
“Daddy likes to start our weekends with me dressed to fuck,” Mary grinned. Ashley was flushed and speechless.
Mary went to the kitchen and pulled out a bottle of Oban Scotch bahis şirketleri Whiskey and a Waterford crystal highball glass and placed it on the small bar in her living room. She went to her Iphone dock, selected a playlist of classic rock, and set the volume at a discreet level—just above quiet.
“Look, you might as well see from the get-go what this is about,” Mary said. “I would fuck Dan even if he wasn’t my Sugardaddy, ok? I really like him and the money and presents are just icing on the cake. If I didn’t like him, if there wasn’t some chemistry, I wouldn’t fuck him like a bitch in heat. Older men just do it for me. I can really get my freak on with him. If this trips you out, then now is the time to decide but you have to promise to keep this on the DL.”
Ashley gulped. She wondered what the fuck she was getting herself in to. “Are you going to fuck him in front of me?”
Mary smiled. “Do you want me to? I will. I have. If he wants to I will fuck him right here while you watch. Are you staying or going?”
Ashley knew it was decision time. “No, I’m in. This is…it’s pretty hot.”
Ashley was about to begin the line of questioning again when Dan knocked at the door. Mary flew across the apartment and flung the door open wide, not caring who might see her in what she called “Daddy’s Angel get-up.”
Mary threw herself into Dan’s arms and pushed her large tits hard against him. “Daddy! Hi, Daddy! Oh, I missed you!” she exclaimed genuinely. She took two steps back towards the doorway and did a slow spin. “Well? Did I do ok?”
Dan’s reaction was to leer at her in mock appraisal, as though he was passing a serious judgment on her appearance. “Nailed it again, good girl.” They both laughed as Dan walked in and closed the door.
“Dan, this is my friend Ashley I mentioned to you. Ashley, this is Dan. Ready for a drink, baby?” Mary picked up the glass and went to get ice for his drink as Dan and Ashley made their hellos.
Dan thought Ashley was pretty hot in a sort of naughty little pixie-gymnast way. She was short, about 5′ even, he guessed. Short, curly brown hair and bright green eyes, Dan noted, and she was very thin with small B cup breasts. Probably a dress size 0 or maybe a 2, Dan thought, and a very pretty face, very feminine. She wears her make up well, a good sign.
Dan sat on the couch and Mary brought him the drink and arranged herself on his lap. She whispered in Dan’s ear and they both chuckled. Dan began to run a finger lightly up and down Mary’s soft inner thigh as they shared a long, deep kiss.
“So Ashley, a pleasure to meet you,” Dan said. “Mary says you are in the market for a Sugardaddy. That right?”
“Well, I think so. I don’t know much about it. Just a little bit about you and Mary.”
Dan fixed Ashley with an earnest look directly in her eyes at as his hand continued to stroke the leg of the beautiful young blonde perched on his lap. “Ashley, are you to be trusted? Do you really know how to keep a confidence? It’s different than keeping a secret. A secret denotes something shameful. A confidence is about being trusted. Understand?”
“Yes, Sir,” Ashley responded reflexively. It was like talking to her father when he was telling her something important but not scolding her. It made her even wetter.
“I can make some introductions for you. I know some gentlemen who might enjoy meeting you. Either that, or you can take your chances on the websites geared towards these type of arrangements. They do not come with my highest recommendations, but they can work. I take it you need money for something.”
Ashley blushed furiously and looked at the floor. “Well, not much. Just enough for a trip or something,” she mumbled.
“Look. You can be honest with me. You are safe. As Mary can attest, I certainly know how to keep a confidence.” Mary smiled and nodded to Ashley then nuzzled Dan’s neck and began to very lightly nibble his ear. Dan moved his hand from the shapely thigh and began to trace a finger up and down along the centerline of Mary’s taut tan stomach.
“I can mention I have recently met a beautiful young woman who is in the market,” said Dan. “You’re a spinner, a petite girl that can be imagined as being able to spin around a man’s cock like pinwheel. In some quarters a young spinner like you are highly sought after.
“Am I too blunt? Too crass? Am I making you uncomfortable? I do not mean to do so. I just want you to know as much as possible about what you are taking under consideration. I am not objectifying you.”
Ashley suddenly didn’t feel the hot blush and actually felt more…confident. “No, not really. I’m interested,” she said.
She noticed Dan’s finger had moved down Mary’s tummy and was now moving back and forth along the elastic of Mary’s damp white panties.
“So I very discreetly mention you to some men I know. Maybe you join Mary and I and another Sugardaddy for dinner so you two can get to know one another. It’s like a blind date. If the two of you hit it off, then whatever arrangement you make is your business and no one else’s. If there is no chemistry then everyone goes separate ways and no hard feelings. I get nothing out of this and only considering this because Mary asked,” said Dan.
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