At 58 life was decidedly good. Not everything had gone exactly to plan. I had lost my wife ten years earlier, but both of our adult children were out of the house, past college, and married. I had started my own construction company with my best friend 30-years prior. We had grown it into a multi-million dollar venture. Most days I let the company run itself, and my friend had long since sold most of his stake and moved to Hawaii. Not a terrible plan.
So I found myself usually living alone, lots of disposable income, and no obligations. I took up yoga, laid into golf, and occasionally dated 30-and 40-somethings for fun. But that was about it. And although my age was starting to show, at 6'3" and with ample time on my hands I kept in better shape than most of my peers. When the hostess at the country club caught me leering or I snuck a peak at a hot little number in the yoga studio... it usually didn't go anywhere, but they certainly didn't seem to mind. A "silver fox," they called me.
For years, life had few surprises until my encounter with Josephine. It was the last week of May and my company usually awarded scholarships to employee's children headed to college. Josephine, at 18, was leaving the local high school and heading to a nearby private university. She was the daughter of one of our electricians and she had received a partial scholarship to be on the university's cross-country team. The tuition was pretty extraordinary and although her father intended to help, they couldn't cover it all. Even our maximum scholarship amount wasn't enough. The staff that handled the internal scholarship application process had forwarded her details to me and I was to meet with her to see what we could do.
So on another lazy Saturday I had an 11:00am appointment with Josephine. She arrived at my house, a red brick home on the outskirts of town that was starting to feel ridiculous to live in alone. My office looked out to the front courtyard and I saw Josephine pull up in a red Jeep wrangler. It had a slight post-factory lift and made it look like a formidable machine. I was surprised when out of the excessively large Jeep stepped a beautiful pixie.
Josephine was about 5'4" and looked as if she weighed 100 pounds soaking wet. She was fit, from the running that earned her athletic scholarship, but not overly muscular. Nice and toned. She had dark auburn hair that was tied up into an extensive bun. It looked as if she had so much hair it would easily reach down to her ass but was contained above her shoulders for now. She had shown up for the appointment in a loose, but revealing, white athletic racerback tank top. The sides of her top flowed and occasionally exposed her ribs and taught stomach. The top cascaded around the very top of black yoga pants that left almost nothing to the imagination. Her firm little bubble butt was on display for all who were curious. Her pant legs crested into the folds of what I imagined was a very tight pussy, and her thighs looked gorgeous swishing from her Jeep to my front door. To top it all off she had donned a pair of all-white converse tennis shoes that accentuated her youthful, energetic vibe.
My housekeeper greeted Josephine and brought her into my office where I immediately noticed her eyes. They were deep brown and sat just above a smattering of freckles on her cheeks. As our eyes met I think I felt the hint of a spark. Her face was perfect. Gorgeous and stunningly symmetrical. She had applied a little bit of makeup: mascara and attention to her eyelashes to make them appear bolder. I covertly tried to take all of her in before pointing her small, feminine frame to the chair in front of my desk.
"Good to meet you," I said, "Please... sit."
I took my seat opposite Josephine behind an imposing wooden desk. The gorgeous, sexy teen in front of me sat in the large armchair I provided. Her lithe frame totally absorbed by the furniture. She crossed her toned legs and I couldn't help but notice the way the "V" of her abdomen and pussy in her yoga pants. How it connected to her petite thighs.
She looked embarrassed, but not from my fleeting glance.
"What's wrong?" I asked.
Her voice was angelic. Sweet, submissive, but with just enough confidence. I think she knew of the effect she had on men. "Nothing," Josephine said, "I'm sorry I didn't realize how nice your home is. I feel completely underdressed."
"Not at all," I said, "I'm not very formal." I knew something about my answer probably didn't land. Even though I did think of myself as informal, I was sitting in freshly laundered jeans, $300 shoes, a starched shirt, and blue blazer. She seemed to relax a little, but only a little.
I picked up the papers my secretary had laid out for me on all the scholarship applicants. As a blue collar industry, there were not that many children even interested in going to college. We also had an apprentice program where they could take up most of the trades anyway. Josephine was one of the most promising applicants and what she was really asking for, whether she knew it or not, was an exception to our funding limits.
"So give me the lay of the land," I said, "What can I do for you?"
She cleared her throat and sat up a little straighter. "Well - first - I appreciate so much that you're talking with me today and all the company has done for me and Dad." I nodded and she continued. "It's kind of a complicated situation but I've got a half scholarship to do cross-country and the company is kicking in $10,000 per semester... which is amazing. But that leaves $15,000 a semester for tuition and fees alone. So like, I'm not even living on campus and still have other expenses. Dad will do what he can but he can't really make up $30,000, $50,000 a year."
"I'm surprised you're not on any academic scholarship."
"Yeah," she said. As she talked I found myself focusing too much on her lips, the way she nervously glanced to the side as she spoke, and how easy it would be for me to pin her against a wall and have my way with her. "My grades are pretty good, but some of the people who come here are the smartest people in the world it feels like. There's not much left for me."
"So why not student loans? Just curious." I said.
"Well," she bit her lip, "I could. I know I could. But I've just read so many horror stories about student loans and... well... I'm not going to be an engineer."
"What are you going to be?" I asked, and for the first time her eyes looked up to me and I could see her swell with confidence.
"Honestly," she said, "I want to be an artist. They have a great fine arts and art history program. But I promised Dad I would take business courses and stick with Spanish as my minor, and I would consider being a business major. At least have something on that front." She looked away again, "He was thinking if all else fails having some business savvy and being able to speak Spanish... I'd at least know people in the trades who could get me a job. But not a job that can make up $200,000 in student loan debt any time soon."
I found myself becoming intrigued. "What kind of art?"
"Everything!" she said, "I paint mostly, but I'm starting to get into street art, stenciling, and some other mixed media. They have a whole class on Banksy at the school."
We talked for another fifteen minutes about her art, college, and what she had ahead. As she spoke I could feel myself becoming inappropriately smitten with the creature some 40-years my junior now sitting in my home office. She was stunning, driven, and the sexiest thing of all... she was in need of me.
"Alright well," I said, after a while, "Josephine the thing we're working against here is that the scholarship fund was designed for the state colleges. A maximum of $10,000 per semester, per student." She immediately looked crestfallen. "Can I ask what is your plan if we can't make up any of the difference? Will you still go?"
She took a deep breath. "Honestly I don't know. I was going to try to find a summer job to help but I also wanted to take this internship. I think I would go but ---" she stopped short.
"What?" I asked.
"It's nothing, a friend of mine had another solution. I don't know. I have a lot to figure out." She stood up and, as she did, I caught site of something I had not noticed before: her magnificent, perky, C-cup breasts. They were tucked in tight by her sports bra, which appeared to be a built-in feature of her tank top. As she stood up I reflexively got to my feet as well.
"Well wait, we're not done," I said, "But what's the other solution?"
She looked embarrassed and began to blush, bringing out the perfectly tanned complexion of her facial features. "I can't really-" she said, "-I appreciate your time."
"Josephine," I said, "You've come all this way. I want to find a solution for you. What all is on the table?"
She placed one hand back on her armchair while facing me, she immediately looked down at the floor. "Well, have you ever heard of Seeking Arrangement?"
Not what I expected! I smirked a little but Josephine, looking at the floor, didn't see. And that's when the old man got an idea and his dick grew two sizes too big that day. "No," I said, steeling my composure, "What is that?"
"It's a website," Josephine said, "A dating website. Where you... where girls who are younger find older men to date who sort of... take care of what they need. So to speak."
"Oh," I nodded, "A dating website? So I gather... they take care of you and you... take care of them?" She blushed again and looked up at me.
"Yeah," she said, a little too comfortable with me, "That's the idea. Anyway my friend Becky is a couple years older and does it and she thinks it's great. Perfect for me. I don't know." I took one look at the petite, tight, little teen before me and then took a mental picture of my assets and hatched my plan.
"Well," I said, "Maybe that's not a bad idea. If that's something you're interested in ... maybe there's an arrangement to be made with me instead?" She looked up at me and cocked her head to the side.
"Like what kind of arrangement?" she asked. I detected a hint of a devilish smile underneath what was 90% innocence.
"Well if you're looking for an... arrangement," I said, "And I'm open to that and can help you along. I would work something out if you want."
"Well what would we do for my tuition?" she asked.
"You would actually be in good shape," I said, "I can grant you a bigger scholarship through the company, the $15,000 per semester to cover your tuition. What are the other expenses, what is the internship you want?"
"Well," she said, taking a step forward to come to the front of my desk. "I mean I have my car payment, I need to get a meal plan, and a girl has to cover a lot of other things you know. The internship is at the local art museum working on one of their exhibits and all of their showings this summer."
"And if you could, would you move into the dorms?" I asked. She laughed.
"Yes, of course," she said, "But that's another... I don't know... it's like another $25,000 a year." The room fell silent for a few seconds while I formulated my offer.
"Ok," I said, "How about this.... I will make sure my company covers the rest of your tuition that your athletic scholarship does not. I will cover your dorm, car, and other expenses and an allowance, let's say a stipend, to get you through the summer."
Her eyes lit up, as if all her prayers had been answered. She deftly ran around the desk and jumped into my arms to give me a hug. "Oh my god thank you!" She yelled, burying herself into me. I found my hands drift to her back and for the first time got a sense of how slender and fuckable she was with me towering over her. After a moment she stepped back, awkwardly.
"I'm sorry," she said, "I didn't mean to - you know - personal space." I smiled reassuringly, knowing full well personal space was going to be the least of our concerns.
"So what's the arrangement then?" she asked. "What do you want from me?"
"Well that's kind of the pickle," I said, "It's not a done deal yet."
"Oh my god, anything!" she said.
"Well for starters," I said, "I am a very particular man and this is a significant arrangement we're making. I expect my conditions to be met." She nodded. I began to list my expectations and with each one she obediently indicated her acceptance:
"I know you're a runner but I expect you do yoga and pilates too, at my expense, to stay in shape.
I'll send you to the spa every once in a while but I expect you to keep up appearances and grooming; I believe the spa I know can do Brazilian waxes.
You are to be on call for me. Scheduling conflicts come up but I expect you to answer my calls and texts and be available when I ask. I'll pay for your phone.
I expect exclusivity. No other sugar daddies or boyfriends.
And perhaps most important of all for you to know is that, in the bedroom, I am very direct and expect you to do as you're told. I can be pretty domineering and I do not like to be told no.
If you have any hesitation or think you can't meet those expectations you should tell me now. I can still arrange for the scholarship boost but the rest is off the table."
Josephine took a breath and considered her options. It seemed to be a clear choice: she could form an agreement with one sugar daddy instead of resorting to a menagerie of old men to service. In exchange all her problems would be solved. More to the point, the man in front of her was a successful, reliable, and frankly - sexy - option. A man she'd known of most of her life but only just met that day.
"Ok," she said. "I agree."
I smiled and reached out to place my right hand on her hip. "Good," I said, "The first thing to know is that when we're alone I expect you to address me as 'sir,' do you understand?"
"Yes, sir!" she teased. "What's the second thing?"
"Ah, well," I answered, "The second thing is that I expect a down payment today. I want to see if you're up to the task or if I'm going to have to train you."
"Oh," she said, "What kind of down payment?"
In a flash, I turned her small frame around to face away from me and bent her over my desk. She braced herself, caught totally off-guard, and shuttered as I smacked her tight little ass.
"What kind of down payment, SIR." I corrected her. I let my hand rest firmly on her cute little bubble butt. The entire thing fit into the palm of just one hand. She took in a sharp breath and then let out a single, surprised giggle.
"I'm sorry, sir," she said, "What kind of down payment, sir?" I grabbed the bottom of her tank top and pulled it up over her head, exposing her top half. I then spun her back around to face me as I sat back in my chair again. I got to see her perfect, dime-sized nipples free on her magnificent C-cups for the first time. She made no effort to hide them, she simply stood in front of me with her hands now resting on her yoga pant-clad hips. Her toned waistline was on display and a single studded belly button ring was prominently featured.
"Well let's see what you've got," I said, "Come kneel in front of me and suck on my cock, Josephine." She took another breath that seemed to bear the weight of this being the point of no return. Josephine then adjusted her hairbun and sank to her knees, her little head resting between both of my powerful legs.
She adjusted herself to get comfortable, her ass resting on the back of her white chucks, and then both of her diminutive hands came up to unzip my jeans. I had already felt the blood rushing to my member since the moment she said "Seeking Arrangement." I knew I was going to need very little attention to get to full mast.
Josephine reached into my boxers and her hand found the base of my dick. Just from wrapping her thumb and forefinger around it she looked up at me in surprise. "Oh... my... god..." she said. After a few seconds of fumbling around with my clothes she finally freed me from the constraints of my pants. A nine inch, adult cock that was plainly thicker than her forearm was pointing straight at her young, elfen features.
She started laughing for a few seconds and then finished with an awkward, dispirited croak before focusing on me again. "Ok maybe we need to renegotiate..."
I smiled, "Renegotiate... sir," I corrected, dangerously, "Why would we need to renegotiate?"
"Well, sir," Josephine said, "I assume you would have a manageable dick, sir. In fact I hoped it would be nice, sir, but this is like ... 'ha ha' big. Like a practical joke cock. I think I should get at least... overtime... or something for this thing, sir." She did her best to wrap her right hand around the shaft and began experimenting with moving me and jerking me off. She looked at home. A little nervous but also excited. I felt it was best she learn to use all her assets in life to get what she wanted. In many ways I was a noble teacher, out to speed her along in her lessons of influencing men.
"Let's see how you do," I said, "And if your efforts are above-and-beyond I'm open to performance bonuses." I smiled. I was beginning to even 'catch feelings' for this beautiful creature kneeling in front of me.
With that, Josephine bit her lip and gave me a moment's consideration before wrapping her 18-year-old lips around the head of my cock. For thirty seconds - at least - I was lost in bliss. She started to work on pleasuring me. If the size of the member under her tutelage was a problem, she didn't immediately show it. In fact, even though I was stretching her lips beyond propriety, she was able to fit my girth into her pretty mouth. She began taking more and more length into her young throat.
I sat back and let her work her magic for several minutes, enjoying my prowess for converting a money-losing scholarship into a money-losing fuck buddy who was, by my measure, a perfect ten. Less than ten minutes in I noticed that she seemed to be getting more comfortable. She had adjusted her posture, she would deepthroat me in exquisitely slow fashion only to then switch to a rapid, self-face fuck. I enjoyed every minute. The fast, the slow, the deep and shallow. She took a few breaks, presumable to rest her jaw, but would lick my shaft and let her tiny hand massage my cock while she regrouped... ready to go at me again.
Close to fifteen minutes in she was able to take me deeper into her throat than she had before and would indicate this by gently gagging on me and quickly coming up for air. It was then that I decided she was ready to see what I meant by being "direct" in the bedroom. In this case... in my office. Semantics.
I could feel the familiar stirring in my balls and knew I was getting close as this tiny vixen serviced the cock of a man more than three times her age. I took my right hand and wrapped it around her teen head, buried in the topknot of wild auburn hair. Once in position I took over and insisted I be in control of her motions. To my delight, Josephine responded by dropping her hands to her thighs and submitting to my inclinations. I had to possess this young woman. I simply had to have her and - to me - that meant controlling her.
For three or four glorious minutes I took her teen mouth under hand and made her work my dick to my satisfaction. I pressed her further down my shaft and forced her to deepthroat me beyond what she could do unassisted. That meant that for a few beats she would quite plainly choke on my cock. She would squirm a little, she was not used to being dominated I was sure. But when I changed pace and fucked her teen mouth at a quicker speed I would find that she let out a few gentle moans. Most importantly, she kept her hands on her thighs. She struggled, but she did not protest.
"Look at me, Josephine," I said. Her ravishing eyes (each streaked with tears that had carried mascara across her cheeks as I gagged her) looked up to mine. "Look at me baby," I continued, "I'm going to cum in your mouth." She nodded as I made her take my cock only halfway down, enjoying how cute she looked with her mouth full of my dick. "I hope this was understood, but I expect you to swallow."