Unexpected Sugar Daddy Pt. 04

Twenty minutes ago I had texted Josephine and demanded she report for duty at my house. Since our first night together a week had gone by and we spent several days, largely via text and email, arranging for the transfer of funds, purchase of her artwork, and deposits on her new living situation. We had also agreed to a monthly stipend that would cover her expenses.

On day three, first thing in the morning, she texted me and asked why I had not called her over, evening adding a smiling devil emoticon. I replied that I was not as young as I once was, that our first day together had satisfied me extensively. Of course I wanted more, but I wasn't planning to have her whore herself out to me every single day. She followed up by texting me a picture of herself, point down from her point-of-view. She was in her bed, completely naked, and her delicate hand was reaching down to play with herself.

'What if I want more now, sir?' she asked.

'I guess you'll have to earn it." I replied. Four more days went by, and more flirtatious texts came my way. On the evening of day three she sent me a selfie of her in the shower, looking over her arched back with pert little butt thrust back. The text read, 'Wish you were here.' I didn't reply.

On day four she sent me a picture of her outfit on her first day of her art internship. She had selected a pair of trim-cut black slacks, they hugged her thighs so nicely, and a lavender short-sleeve blouse. She had picked matching black heels that exposed her toes - freshly manicured after I had sent her to the spa for detailing. As a treat for me, she left her slacks unzipped to demonstrate she was going commando. The soft skin of her smooth mound on full display. Her text read 'I hope I don't start daydreaming of you at work, I won't have time to change if I do.'

I replied, 'Good luck on your first day.'

On day five, in the evening, she sent me a drunk text. She had been at a party with friends and it was almost midnight. 'Why aren't to flirting back with me?" she wrote.

'Maybe I want to build your anticipation,' I answered.

'That's not very nice,' she said, 'I thought you would've asked me to come over again by now.'

'So you can earn your keep?' I asked.

'I want to earn my keep, sir,' Josephine said, 'But you're not letting me.'

'How do you want to earn your keep?' I asked.

'I don't know,' she said, 'But I know you'll take what you want.'

'You forgot to say *sir* Josephine...'

A few minutes went by and I was treated to a selfie of her in the mirror, standing with only her pair of blue, hightop chucks on. She was facing away so that I got an incredible view of her ass, with her back slightly arched to accentuate its curve.

'Well maybe you'll teach me a lesson soon, sir.'

'I will,' I answered, 'Goodnight, Josephine.'

On day six we were all business but I could tell she was getting frustrated with me. I let her endure the wait another day and then on day seven, when I knew she was off work, I called her over at 2:00pm. She arrived wearing a pair of dark blue yoga pants, her white chucks, and a form-fitting athletic top in white. As soon as my housekeeper let her in and I had closed the door to my office, where I had been waiting for her, I dragged her over to my desk and roughly bent her over.

Josephine giggled, her head planted on some of my papers. "I guess we're not playing around today, sir!" I pulled her pants down to her knees, exposing her panty-less ass, and landed a firm swat on her left cheek. I was already hard in anticipation and couldn't wait to fuck my hot little sextoy again.

Josephine had one leg bent and was up on her tennis shoe-clad toes given the height of the desk and her petite size. I unzipped my jeans and let my fully erect member rest on her lower back. She groaned, feeling its weight and size land on her tiny lumbar region, nestled between her two back dimples. "Oh my god," she said. She reached forward to grab on to the front of the desk for support as I let the head of my dick make a trail up and down her pussy lips until I was coated in her juices.

I put my other hand on her lower back to hold her in place and then pushed forward to begin my assault on her tight, smooth, teen cunt. The girth and volume of member seemed to sink into her folds, it felt like I was weighing down her entire body with the gravity of my much older prick.

Once I had expanded her passage I got to work pumping the 18-year-old piece of ass I had paid for in droves that week. For her part, Josephine moaned and took the pounding she deserved. I placed both my hands on her hips, further pinning her to my desk as I thrust in and out of her.

I looked down to see her yoga pants wrapped around her knees and both of her white chucks pointed toward each other at the toes. Her feet were squirming underneath me to endure the ravishing fuck I was delivering. After several minutes of me enjoying the sensation of her tight inner walls she finally spoke.

"I'm so-glad you-called me-over, sir," Josephine said, "I've been - desperate - for your cock - all week." Hearing my little sugarbaby plead for me sent me over the edge. I grabbed a fistful of her loose brown hair and yanked her lithe body up off the desk as I discharged a week of cum into her obedient womb. Her little twat began to spasm and milk my shaft for more and she let out an audacious groan of approval.

When I had finished I released her hair and patted her back between her shoulder blades. She was still catching her breath, bent over my desk, as I pulled her yoga pants back up. I slapped her firm little butt again and she perked up.

"I appreciate you coming by, Josephine," I said, "Tonight I have a surprise for you. Send me some choices of outfits this afternoon."

She laughed, "So that's it? Just call me over and pound me out then send me on my way?"

I nodded and sat back down, "I'll make tonight worth your while, but you should expect to be available to service me and leave when I ask." She shrugged her shoulders and turned to leave.

"Well I'll see you tonight, sir," she said as she left my office, half frustrated and half relieved that I had finally fucked her after making her wait for a week.

***

That afternoon we revisited our texting game. This time I knew I was taking her to a private dinner on a rooftop terrace downtown. A formal attire evening. Josephine started her texting with choice of shoes. Black pump heels, black converse sneakers, or tan suede ankle booties. I picked the heels, they made her small feet and toned calves look amazing.

Next was my choice of bottoms. She offered up a pair of skintight low-rider jeans, a form fitting red skirt, or the quintessential little black dress. The hem came only a quarter of the way down her luscious teen thighs and hugged every inch of her hips and waist. It came alive at the top with strategically placed fabric that barely covered her C-cup tits, exposing vast amounts of the top and sides of her breasts. Two minuscule straps connected the triangles covering her breasts to a tie around her neck. She had also tied her robust mane of hair into a fancy bun.

Obviously I picked the little black dress.

'And now for the final question...' the next series of texts displayed her in profile, lifting the hem of her dress up over her hips. As a choice of panties I was to select from: sheer black lacy boyshorts, a diminutive purple thong, or nothing at all.

'No panties for you tonight,' I ordered.

'Yes, sir!' Josephine wrote. 'Where and when?'

'Come to my house at 7:00,' I replied.

***

Josephine arrived in the form-fitting little black dress, black pump heels, and no panties that I had prescribed at 7:00 on the dot. Seeing her petite, tight little body exit the powerful Jeep she drove, done up to the nines, was incredibly sexy. As she approached the door I stepped out in a blue blazer, white dress shirt, and dark grey khakis.

"You clean up nice, sir," Josephine said as the click of her stiletto heels echoed along my stone entryway. She looked absolutely devastating, just laying eyes on her started to get me hard. Her hair and makeup were both finely appointed and elegantly done.

Josephine stopped within just a few inches of me and, even in her heels, looked up at me with her stunning brown eyes. I felt her eyes looked best as they kept themselves locked on mine while her mouth sucked my cock.

I reached one powerful hand around her waist, settling on her firm little teen rear, and pulled her whole frame forward for a kiss. Feeling the thin material of her dress hug her ass and feeling confirmation that she was going commando, as ordered, resulted in a rush of blood to my manhood. 'Soon,' I thought to myself.

After a brief kiss the car I had ordered pulled up in my driveway. Not a ride share, a towncar you had to call and make a reservation for. The principal benefit of which would be a driver with a lot of discretion. The car was a black Cadillac XTS limousine. Not a full stretch limo, about half that size, but enough to warrant a dividing wall between the driver and plenty of space for four passengers.

I nodded to the driver and opened the door for Josephine. She stepped down into the car, briefly flashing the fresh Brazilian wax I had paid for earlier in the week. I stepped in and soon we were off to our destination.

"So where are we going, sir?" Josephine asked.

"To dinner," I said, "It's a surprise."

Josephine leaned into me and whispered in my ear. "Are there any other surprises tonight, sir?" I smiled and confirmed that the dividing wall between the driver and our passenger section was firmly secured.

"There are, for instance, you're going to service me while we drive." Josephine recoiled, startled that I was setting that tone for our car ride. She hesitated a moment and then spoke.

"Oh... ok," she said, "How would you like it, sir?" I spread my legs and pointed toward the floor of the car.

"On your knees," I said, "And my way."

"Your way?" Josephine asked as she slid over my thigh to plop both knees on the floor of the car between my legs. Her cute little head bobbed up over my lap, looking submissively up at me.

"Yes, my way," I answered. "In a way... I misspoke. You're not going to service me so much as I'm going to use your mouth to cum. Dinner is twenty minutes away. Should be plenty of time."

Josephine cocked her head as she dutifully unzipped my pants, clearly apprehensive about how the drive was unfolding. "Plenty of time for what, sir?" She pulled out my rapidly engorging member and pointed it at her own lips.

"For me to have my way with your throat," I said. With that, Josephine started obediently sucking on the tip of my member. After just a few seconds I ordered her to put her hands down, which she did... knowing what was coming.

"Let me control your motions, baby," I said as I took her gorgeous, 18-year-old head into both my hands and began rocking her mouth back and forth on my dick. Seeing her kneeling before me on the floor of the car, her pretty face at my disposal, made my dick swell to its full potential in seconds.

Josephine willingly took the throat fucking I demanded. The lipgloss she had applied for the evening reflected the soft lighting inside the limo as her mouth stretched around the circumference of my member. God she was such a good little cocksucker. I tightened my grip around her teen skull and began pressing her head down further as I thrust my hips up. Several times, as her lips and nose were buried into my pubes, she gagged violently. But she kept her hands resting on her thighs and let me use her.

After several minutes of ploughing her esophagus I made my move. At the apex of forcing my cock down her throat, and with her cheeks rubbing against the zipper of my jeans, I held her down for several seconds and choked her on my shaft. Josephine tried to take the pressure as best as she could and I soaked up every moment of feeling her throat contract around my rigid prick. She gave it her all but eventually her reflexed kicked in and she brought one hand up to press against my thigh, pushing me away.

The moment I felt her resist, the familiar pulse of a primitive, explosive release of semen began and I let out a deep, guttural moan as I shot wave after wave of cum down Josephine's struggling throat. She brought both hands up into the air at her sides, trying not to resist but reflexively needing to do something with her hands.

"Look at me baby," I said. Josephine's watering eyes looked up at the sugar daddy blowing his load directly into her unsuspecting tummy. The moment our eyes met a streak of mascara fell down her cheek. That brought another shot of cum out of my sack and I basked in the sight of seeing her little heel clad feet struggling beneath her slim frame.

I let go of her head and my dick came hurtling out of her mouth as she gasped for air. A long trail of her saliva came popping out with my manhood and fell onto her chin and the floor of the car. Josephine took in several shallow, rabid breaths and began swallowing the excess spit that had accumulated in her oral cavity. When she finally came to she looked up at me, exasperated.

"That was," she patted my thighs with her hands, "That was a little much." I leaned up and took her neck in one of my strong hands and tilted her backward to look at me. One of her hands instinctively grabbed my arm.

"That was a little much, sir," I corrected her. "You come at a pretty high price, Josephine. And you're worth it, but I don't get told no. Do you understand?"

She nodded warily and I let go over her neck to brush her tear-stained cheek. "You'll get used to it, and it's not like I always need to be rough with you." I pulled her up to sit on my lap and enjoyed the feeling of her firm little arse resting against me.

"Clean yourself help, baby," I said, "We'll be there soon."

***

Josephine and I arrived at "La Terrasse," a fashionable French bistro that was housed on the top floor of an old red brick bank from the late 1800s. A small elevator took us up to the roof where a cute hostess, probably just a year or two older than Josephine, escorted us to the table I reserved.

Before long, Josephine had settled in after the rough face-fucking I had given her in the car and we talked about the start of her internship. It sounded like the perfect fit and I found myself proud of enabling her endeavors. She had a zest for life I found insanely attractive.

After an hour and a half the dessert was finished, the check was paid, and the wait staff diligently cleaned up and departed so we could enjoy the view alone. Only a few of the staff gave away their suspicious looks about our age difference during the meal.

When all was quiet I took Josephine's hand and guided her thin form over to the rails so she could take in the sunset over the city. "Beautiful isn't it?" I asked. She looked out and agreed, admiring the view.

"It would make a great painting." As she considered the potential art before her, I maneuvered myself around her back and pressed myself against her tiny frame. My hands slid down both of her sides and began pulling up the material of her dress. She squirmed in self-defense.

"What are you doing!?" she asked as I exposed her bare little pussy to the night air.

What are you doing, sir," I corrected, landing a single swat onto the flesh of her teen ass. I spun her back to face the view and kneeled behind her, lifting the hem of her tight dress up to her waist. I placed both my hands on her hips and tilted her slightly forward, exposing her delicate folds from back to thighs. With Josephine in position, I leaned forward and began expertly ravishing her with my tongue. I started with her outer lips and then focused all my attention on her sweet little clit. After a minute any resistance disappeared and she began pressing herself back onto my face.

It took some time for her to get out of her own head, but after ten minutes she let go of the rail, grasped a handful of my hair. And exploded onto my tongue with an earth-shattering orgasm. As she came down from her high I began licking her sweet little asshole. Josephine giggled and protested a bit but was still drowning in dopamine.

Before she could entirely catch her breath I stood up, unzipped my pants, and pressed my rock hard cock into her tight folds. She gasped in surprise. My hands returned to her hips and I began pumping the little harlot for all she was worth. Her vaginal walls felt so good milking my shaft. She was hot and slick from my oral attention and every inch of her teen cunt gripped onto my member.

After a few more minutes I let one hand wrap around to the front of her sex to play with her smooth pussy while my other hand found her neck and latched on. One of her heel-clad feet came off the ground as another climax overcame Josephine. I grasped her throat harder and used it to pull her whole body down and back onto my dick. I felt the tip of my manhood ram her cervix as her pussy spasmed. I let out a deep, satisfied groan as my third load of the day burst into Josephine's 18-year-old body. Her thighs quivered and squeezed another shot out of my shaft.

When I had enough I slowly pulled out of her. Josephine collapsed a bit onto the rail and pulled her dress down.

"That... was..." Josephine turned and looked at me, completely content. "Amazing... sir." I gave her a kiss on the cheek and we spent a few minutes catching our breath and watching the night sky overtake dusk.