Unexpected Sugar Daddy Pt. 02

After my midday blowjob from Josephine, the world was looking up. She put her top back on, gave me her number, and left $1,000 richer than when she arrived. I watched her lithe frame get back in her Jeep and, when she didn't know I was looking, she checked her hair in the rearview mirror and smiled.

The rest of the day passed uneventfully and I started dreaming of how I was going to enjoy my new prize. Josephine was incredible. Sexy, vibrant, smart. And for now she would be mine.

I checked my bank account around 1:00pm and noticed that Josephine had already cashed her check. No rest for the wicked with her. By 4:00pm I felt I had let her sit on this new situation long enough and was ready to reach out. My generation was prone to calling instead of texting, but I thought someone her age might be more comfortable with a text instead.

'Good afternoon, Josephine. Are you still comfortable with our agreement?'

Less than a minute went by before she answered, 'I am! I'm nervous tho...'

'What are you nervous about?'

'IDK,' she answered, 'Maybe I'm excited too.'

'Do I excite you?'

This time a few minutes went by before she replied, 'Yeah. After I left I had to go home and change.'

'You had to change clothes? What for?'

'Lol,' she answered, 'I got really wet. I didn't want to tell you. I've only gone down on a couple guys but you were so big. I don't know. Apparently that worked for me.'

'You soaked through your panties too?'

'I don't wear panties with yoga pants ;-)'

I could feel myself start to get hard again. God, this stunning piece of ass was going to get whatever she wanted from me.

'Well,' I wrote, 'When are you free tonight?'

'Um after dinner?' she said, 'Maybe like 7. What are we doing tonight, sir?'

'Whatever I want,' I said, 'And first we need to pick your outfit.'

'Well how can I pick if I don't know what we're doing?' she teased.

'No I said WE need to pick your outfit. Send me options.'

'Well do you want me in something formal or casual?'

'No,' I answered, 'Send me pictures of the choices.'

Another few minutes went by before I got an answer. Her reply came in the form of a picture with a text underneath. The picture was a selfie of her in a mirror but cropped so that only the middle of her bare thighs down to her feet were showing. Her thighs looked so delicious. For the first time I was noticing her cute feet, they were proportional to her small figure.

'Well it all hinges on the shoes, sir,' she wrote. Before I could reply she sent me three photos that looked almost identical to the first but she was wearing different shoes in each. One photo showed her in blue high top converse tennis shoes. Another in purple velvet pumps - four inches - with a black bow on the toes. The last was a pair of cork wedges that had at least five inches of lift. I mulled over my options. So many possibilities.

'I love the blue chucks and I can't wait to see you in heels,' I wrote, 'But I want to see you in the wedges. It's summer. They look warm.'

'Yes, sir!' she replied. Another few minutes went by and I received three more texts. This time her waist and below was showing in the mirror and she had the wedges on in all three. My choices this time started with a pair of skin tight, dark blue jeans that sat just below her tiny hips. Next was the bottom half of a white sundress that ended above the middle of her thighs. Last was a pair of cut off shorts that had holes between the pockets and her legs, they displayed the most of her pelvic region I had seen so far. The shorts extended only a half inch from her pussy and she wore a thick brown belt with them. That gave the effect of making the shorts look even smaller than they already were.

'God how to pick?' I responded, 'Your legs are gorgeous. I like all my choices but I want to see you in the shorts tonight.'

I could see she was typing and after a minute I received three more photos, each one showing her from shoulders down to the floor. In all three she was wearing the shoes and shorts I had selected for her. This time each photo displayed a different top. One was a low cut bohemian spaghetti strap in purple, exposing the tops and sides of her perky teen breasts, she had tucked half of it into her shorts. The second was a plain white t-shirt but it was clear she was wearing no bra as her nipples poked gently through the fabric, it ended just an inch above the waist of her shorts... exposing her taught stomach. The third was a form-fitting brown lace that exposed half of her midriff and barley contained her C-cup cleavage.

'What a decision!' I wrote, 'But I think the purple. It's sexy."

Ten minutes went by and I received three more texts. This time taken from the side and showing her profile. The first had her hair down, clearly extending far down her back. The second with her hair up in an elaborate bun. The final choice was pigtails weaved on either side of her beautiful young face.

'All good options,' I replied, 'But leave your hair down tonight for me.'

'Yes, sir!'

'You're forgetting one of the most important things of all...' I wrote to Josephine. She sent back a smirk emoticon and five minutes later I was treated to the best photos up to that point. She had disrobed except for the selected platform wedges and sent me three selfies of her entire body, head to toe, in profile. She had turned away from the mirror so I could only see her side. One hand held her phone and the other arm wrapped to cover her delicious teen tits.

In each photo I was presented a choice of panties: one pair of white lacy boy-shorts that hugged the gentle bubble of her firm little ass; one tiny purple thong in silk that closely matched the top I had picked; and one with no underwear at all... only her bare hips. From the profile of her panty-less photo I could catch a small glimpse of her 18-year-old mound and see that it appeared to be perfectly smooth.

'I love that you don't wear panties,' I said, 'But I think you better wear the purple thong in case you get too wet tonight.'

'Good point!' she said back. 'I didn't know it turned me on so much but I really liked having your cock in my mouth this morning. I had to pick up chapstick though, you stretched my lips so bad.'

'What did you like about it?' I asked. Before she answered I received a picture of her in the entire selected attire facing front, with one knee bent to accentuate her legs. Standing in front of her mirror was a mouth-watering teen fuck toy. Her long auburn hair cascaded around her waist. A purple spaghetti strap top displayed her ample breasts, significantly larger than you would expect on her petite frame. Her ripped daisy dukes were left unzipped and unbuckled to display the purple silk thong underneath. Her sunkissed, toned legs ended in the wedges that gave her entire figure a distinctive bounce.

'Jesus Christ,' I wrote back.

'Do you like what you see, sir?' she asked, 'Because I like how you took charge of me this morning. It was nice to have a man that knows what he wants.'

'I really like what I see, Josephine,' I answered, 'Be at my house at 8:00. Don't forget to bring some of your art for me to see.'

'I think I'm going to enjoy working for my tuition ;-) See you tonight, sir.'

* * *

I felt like 8:00pm could not come soon enough, but wanted to keep my cool. I was looking forward to consummating my arrangement with Josephine. One thing that really took the pressure off was having already drained my balls into her pliant, barely legal mouth a few hours before.

When 8:01 pm rolled around I had setup a table with wine and some charcuterie. Lit a few candles and dimmed some of the lights. My home was a colonial style mansion and, I felt, very impressive to a girl who grew up in her father's apartment.

Josephine arrived in her red Jeep, this time with the bikini top of the SUV pulled up. I opened the door and stood in the doorway waiting for her. When she stepped up to the entrance she was wearing the pre-ordained outfit. She had added a bit of mascara, and was carrying a few bulky paintings wrapped in a canvas blanket.

"Good evening," I said to her. She smiled and I saw the light in her eyes come to life.

"Good evening, sir." I took the paintings out of her hands to carry them for her and leaned down to give her a peck on the cheek. She flustered a little and we walked into my home together. I set the paintings down in the entry way and escorted her to the nearby kitchen where I poured her a glass of white wine. We toasted to the evening and then I asked her to show me the art she brought.

Josephine led me back to the entryway, wine in hand, and my eyes roamed over her backside like I was reviewing a piece of meat at the butcher. She was stunning. She bent down to unwrap the pile of art leaning against my wall, a sliver of her tight butt cheeks slipped out from under the shorts I had made her wear.

When she stood back up she was holding one of three canvasses she brought with her and the content was... quite good. She had painted the face of a woman in mosaic using what appeared to be graffiti spray paint. Each piece of the mosaic looked like a vibrant piece of tile individually sprayed on. It must have taken her days or even weeks to execute.

I stood there in silence.

"Well..." she said, "What do you think?" I let the silence beat another second because I was truly impressed.

"It's really... it's rather good," I said, I lifted my wine glass up to toast to her, "Well done. How long did that take you?"

"Oof like four weeks," she said, "It took me forever to set it up and even longer to actually do."

"Who is it?" I asked.

"It's my mother," Josephine said, "She died when I was ten. This was based on my favorite picture of her." Before I could respond she had set it aside and picked up the second piece. This was a more traditional painting, oil on canvas, of a the historic district of our town. It was also very impressive and vibrant.

"Wow, Josephine," I said, "I mean it you are very good. I can see why you want to pursue this."

"You're just being nice because I went down on you this morning," she winked at me.

"That doesn't hurt... but they're both impressive." She smiled and turned away, picking up the third and final piece. It was a mixed media of sorts: water color, oil paint, and spray paint. She had woven all three materials together to create an abstract depiction of a mountain landscape. It was - like her - fresh and stunning.

"These are great," I said, "And they'll make my job a lot easier."

"What job is that?" Josephine asked.

"Money laundering," I said, smiling. "People might ask questions about how you've gone from struggling to afford tuition to suddenly having all your expenses covered. I'm going to buy some of your art as we go to help explain your cash flow. If anybody asks, 'You sold another piece.' It will help that you are objectively good."

"That would be amazing," Josephine said, turning around to face me while taking another sip of wine. "Where will the pieces go?" She flirtatiously swayed toward me, closing the distance between us, and I was once again reminded how petite and delicate she was.

"Some I'll keep here," I said, "But we'll work out a way for the company and maybe an anonymous trust to donate others to galleries and shows. Start building your name. Growing your brand."

"Mmmmm," she purred, "Is there anything else we can grow?" She closed the distance between us completely and let one hand slip precariously onto my belt while the other held her glass. "Is there any way I could thank you for your patronage, sir?" Josephine was looking up at me, batting her eyes. Her face was a little closer than that morning given the platform wedges she was now wearing.

"There is," I said, setting my own wine down at a nearby end table. I took her hand from my belt and led her down the hallway to my bedroom. She giggled and drained the rest of her wine as we went, setting the glass aside on a counter. Once in the bedroom she got to take in the master suite: a large king bed, two plush arm chairs, a linen-embroidered bench in front of the bed, and a large area rug between each piece of furniture. One door led into the master bathroom and closets.

"Nice room," she said, again closing the distance between us and wrapping her slim arms around my neck. I reached down and placed both hands along her waist, holding her firmly in place. The size of my hands wrapped around her tiny frame started getting me hard. She would be easy for me to dominate and that was going to be clear in short order.

I leaned down and kissed her, gently at first, soaking in the electricity of a first kiss with this creature. Her hands wrapped around my head and her fingers started nimbly playing with my salt and pepper hair. I pulled the purple spaghetti strap top out of the waist of her shorts and moved my hands on to her soft, but toned, abdomen. She moaned into one of our kisses, feeling my hands on her.

I pulled the top over her head and, once cleared, leaned down to kiss her chest and pert teenage breasts. Once I made my way to each tit I gently bit her tiny nipples and she let out a squeal of protest and excitement. My hands reached down to her hips and then squeezed her tight posterior. Her ass was amazing. Just enough bubble and a little curve, but firm. She had such slender hips I could fit all of her in one hand. While I worked on her chest she started kissing, and even licking, my neck.

I unbuckled her belt and began reciprocating the oral attention on the neck by gently starting a hickey above her collar bone. She giggled at the sensation as my strong, mature hands unbuttoned her shorts and began exploring the depths beyond them. I played with the silk material of her thong and ran my fingers over her 18-year-old pussy. She moaned into my ear as I played with her. I could feel the heat of her sex grow and knew a very wet, but extremely tight, prize was waiting for me.

After a few moments of using my hands on some of her most sensitive erogenous zones, I swiftly pulled both her thong and shorts off in one swoop to her feet. She stepped out of them, leaving her wedges on. For the first time I laid eyes on her completely smooth teen pussy. When you got to soak all of her in - gorgeous face, perky breasts, toned stomach, bare little cunt, and supple thighs - all standing in platform shoes and ready to service you... it was too much to withstand. She blushed and bit her lip as I reviewed her.

"Do you like what you see, sir?" she asked. I didn't respond. I just dragged her over to my area rug and took another minute to let my hands roam over her tight body. For a moment I let my fingers dip between the folds of her labia and she gasped as I felt how wet she was.

After a moment playing with her clit, much to her delight, I whispered in her ear. "Get on your knees."

"Yes, sir," she whispered back. Josephine descended to obediently kneel in front of me. She let her hands rest on her thighs and tucked her shoe-clad feet underneath her cute little ass. She kept eye contact with me during her entire descent and then locked onto the crotch of my jeans. I unzipped them for her and pulled out my almost fully erect cock. When she saw it she bit her lip again and admired it like a juicy steak ready to be devoured.

One of her diminutive hands reached up and began gently playing with the base of my manhood. She got in position so that she could plant soft kisses along the shaft to start. As she kissed her way up my member she cooed, "What should I do with this, sir?" I moaned at her ministrations on my cock.

"I want you to take that dick down your throat for me," I said. She smiled and looked up at me, my now fully erect member eclipsing much of her face.

"You know, sir," Josephine said, "You haven't really held up your end of the bargain yet... how do I know that -"

At that moment I placed my hand on her head and firmly grasped her skull before shoving my 9-inch prick into her mouth. She recoiled a little, but I held her in position and began fucking her sweet young face. Having caught her off-guard, it was only natural that she gagged the first few times I pushed myself past her tonsils and into her throat. Both of her hands reached up and applied pressure to my thighs in a reflexive action.

"Look at me," I said. Her deep brown eyes opened and looked up at the much older man having his way with her. "Put your hands behind your back. Cross your wrists."

Josephine did as she was told and wrapped her hands behind her back, ensuring I met no resistance to my forward thrusts. Her fingers grazed the backs of her shoes and I looked over her back to enjoy the sight of this submissive little slut doing as ordered.

I enjoyed her mouth so much. Because of how thick I was, her lips were again harshly stretched around my entire circumference. Whenever I would slow my pace I could feel the sensation of my shaft passing back and forth over the suction of her lips. It was truly magnificent.

"Are you a virgin," I asked her. She shook her head no. "How many men have you been with?" I heard her struggle to say 'two' with me in her mouth and then she held up her hand and displayed two fingers for me. I let go over her head and she began taking over the work of pleasuring me while I took off my shirt. I let my pants down and she helped me remove them. As soon as they were discarded I pressed her face onto my heavy ballsack for her to continue by licking my scrotum. As with every other maneuver up to that point, she complied.

Once I had my fill of her tongue working my undercarriage, I reached down and picked her straight up into the air. She wrapped her legs around me and I carried her light frame over to my bedroom wall. With one hand still holding her, I used the other to position myself at the entrance of her sex. She was pinned between me and the wall, completely at my mercy.

"Are you on the pill?" I asked.

"I have an IUD," she answered. She looked lost in excitement and apprehension.

"Do you want me to fuck you, Josephine?" I asked, "Are you ready for me to take you?" She took a deep breathe and nodded vigorously. With one motion I thrust up and buried my cock into the tightest, most inviting pussy I had ever experienced. Every inch of her cunt grasped me like a vice. The kind of warmth and pressure that men dream of. She shuddered and moaned. Her nails dug into my shoulder blades as I started pumping her hard against the wall.

After several minutes of enjoying the first sensations of feeling each other, I pulled her legs up so that both of her wedge-clad feet were resting on my shoulders. Her legs were pressed against my chest, turning her into a v-shaped sextoy between me and the wall. At that angle I was pounding her cervix hard with every thrust and she bit her lip to take the punishing attention I was giving her.

An eternity went by of having my way with her. When it felt like I had made my point, I let her down and guided her to the bench in front of my bed. I pressed her down so that both of her knees were on the bench and her torso was splayed out onto the foot of my bed. I grabbed my cock and let the head trail up and down her tight pussy from behind. My cock looked almost as wide as her entire teen ass and I had my first view of her puckered little butthole.

When I pushed forward into her again, the lips of her pussy hugged the head of my dick and clinged to it like a rubberband. I grabbed onto her hips and began slowly fucking Josephine in doggy style. The glands of her inner walls contracted and gave every inch of me a deeply satisfying sensation.

Josephine moaned into the mattress and recoiled at the deepest, hardest thrusts. She took it like a champ as I pounded her with reckless abandon. After ten minutes of enjoying my new mount I brought one hand crashing down on her petite rear.