Unexpected Sugar Daddy Pt. 03

Josephine got up from the bed and went into my bathroom to freshen up. Watching her 18-year-old, 5'4", enticing young body saunter off after I demolished her almost got me hard again. When she returned she had raided my walk-in closet and come back wearing one of my white undershirts. The hem of the shirt just barely reached the tops of her thighs. Her fully alert nipples poked through the material.

"Come on, sir," Josephine said, pulling me out of bed, "I want another drink." I put on a pair of black athletic shorts and a grey t-shirt and joined her back near the kitchen where our wine glasses had been deposited. I refilled her wine and we both settled into a nearby couch in my living room. She reacquired her purse and accessories and tied her wild mane of hair into a quick bun above her head.

She sat with her feet resting under her butt and both legs pressed together, pointed toward me. Her sunkissed legs were on full display. With every small movement she made I caught myself looking up the shirt she was using as a dress... hoping to catch a glimpse of her perfect, smooth little pussy.

Josephine and I sat on my couch for half an hour sipping wine and getting to know each other better. She had already looked into moving into the dorms in the fall. She had accepted the summer internship she wanted, but could not afford to take until today. I told her my story of starting the construction company, where my adult children were now (both of whom were at least ten years older than Josephine), and my dating life.

Until that morning, the youngest partner I had in the previous ten years was a 27-year-old hotel concierge in Las Vegas. A trade show perk. The next youngest non-fling was a 38-year-old architect I had dated on-and-off for a year before she moved to London. My golf buddies and local network would set me up with (what they considered) age-appropriate companions who were at least 40. Since my wife had passed many years prior, I was clear with every prospect that I was not looking to remarry. I figured grandchildren would be on the way soon, I occasionally got the travel itch, and frankly I had done lifelong commitment already.

Josephine recounted tales of growing up primarily with a single father who was, by all accounts, a bit of a roughneck. She had nonetheless blossomed into a feminine and capable young woman. She credited an aunt, grandmother, and a few mentors for guiding her to art, athletics, and answering questions she did not want to ask her father.

"Like what questions?" I asked. Josephine giggled.

"All the girl questions," she said, "I'm sure you don't want to hear them. Often times it was uterus stuff."

I didn't balk at the subject, "I have seen two human beings emerge from a vagina, Josephine. Period questions aren't going to scare me."

She laughed. "Yeah I guess that's true," she said, "I'm used to high school boys - even college guys - who get nervous about anything they can't see."

"Been with a lot of college men have you?" I asked, "Those wildly older men... aged 21."

She smiled and winked at me, "Yeah I set a personal record for myself today. 'Oldest guy I have hooked up with' is now a bar firmly set much higher. My previous best was 20." I hung my head in mock shame and disgrace.

"You definitely moved the bar," I joked.

"When was the last time you slept with someone who was 18?" Josephine asked. I couldn't help but be drawn to her confidence, a maturity beyond her years.

"Ummm," I thought back - deep - into my memory, "Probably when I was 19 or 20. I met my wife in college when we were both 21. I had only been with a couple women up to that point."

"You never cheated on your wife?" Josephine asked. I shook my head.

"No," I said, "One time I made out with a waitress at a company holiday party and I once got pretty frisky on a dance floor at a conference. Nothing too exciting. I told my wife about the waitress, I was 40 at the time. She didn't really care. She said she had an intrigue with our landscaping manager for several months and they got a little hot-and-bothered before she stopped things. I also didn't mind. Fidelity for a lifetime is pretty tough, we did better than most."

She took a sip of her wine and seemed to nod in approval. "That is pretty admirable."

"What about you?" I asked, "You've been with two guys? What's your story?"

"Three now," Josephine corrected, "I don't know. I lost my virginity to a guy at a college party one of my friends took me to. I was on-again off-again with my high school sweetheart. During one of the 'offs' is when I slept with the guy in college. My ex-boyfriend and I finally sealed the deal a couple months ago after prom and then we couldn't stop for a while."

"Ex-boyfriend?" I asked, "Why not current?"

"It ended well actually," Josephine said, "It was a high school thing. I'll always have a soft spot for him but I was heading to college and he joined the Navy. He left for basic training a couple weeks ago, right after graduation, we broke up two weeks before that."

"Well I don't want to judge," I said, "But I suspect he will later regret leaving you for a ship full of men. But I'm glad he's serving our country." I toasted to this anonymous ex-lover in the air. Josephine laughed.

"I'm sure we were headed our separate ways around this time no matter what."

"So what have you learned with your two lovers?" I asked, "What do you like in bed?"

She perked up and took another sip of wine. "Well I love giving and receiving oral. I've tried to learn as much as I can about giving head."

"Oh I'm happy to return the favor," I said, "I've got several decades of experience on that score." Her eyes lit up with excitement.

"Excellent!" she said, "Other than that I haven't tried much. Pretty vanilla. I like when I'm pinned down and I think I'd like to be tied up." She hesitantly looked up at me to see what I thought. She seemed relieved when I casually nodded my approval and mentally added that information to my queue of things to do to Josephine.

"I assume you haven't tried anal?" I asked. She was mid-sip of wine and snorted some of the fluid out when she heard my question.

"No," she giggled, "Not yet. Maybe not ever! And I can barely fit you in the places you're supposed to go. I really don't think I could take your cock... that way."

"Well remember," I said, "Part of our agreement is that I do not like to be told no." Josephine took another, this time choke-less, sip of her wine and set her glass down.

"Well there's a lot we still have to try first, sir," she said. As she spoke she spread her legs and then sat up to straddle me on the couch. "For instance, if you're ready, I would really like to ride your cock." I set my own wine to the side and ran my hands down her fit legs, under the shirt she was wearing, and onto her slight hips.

Josephine let her hands trail down my chest until she arrived at my shorts. She reached under them and began firmly squeezing and pulling on my cock. As she did that, she kissed my cheeks, jaw, and neck. When she felt my member grow in her hands she would coo into my ear. Finally, she pulled me out from the waistband of my shorts and pressed the tip of my cock against her dripping, tight fuckhole.

Josephine whispered into my ear, "Can I ride your cock, sir? Please." I lifted the white undershirt over her head and let my hands roam her lean, nubile body.

"Mmmm," I answered, "I don't think you've earned it yet." Josephine immediately began gyrating her hips and bucking her torso. A demonstration of what she would do if she could ride me. The result was the head of my prick got a massage from the slick, soft folds of her labia.

"Please, sir," she said, "Pleaseeee! It will feel so good in my tight, little pussy. Don't you want to make me take it all? I promise I will be -"

At that moment I applied my full strength into the grip I had on her hips and forced her tenacious little cunt down on my old dick. She moaned and gasped but immediately started bucking her hips to ride me. Her teen pussy milked my shaft for all it was worth and I could feel the head of my member pound into her cervix with every other thrust.

I reached down to grab on to both of her supple little ass cheeks and my fingers grazed the outer lips of her pussy. I played with her sex and could feel just how much pressure the girth of my cock was placing on her vaginal walls.

After a few minutes getting accustomed to my size, Josephine leaned into me so that her head was curled into my neck. She began shamelessly pounding herself with a cock three times her age. She was ravenous for the sensation of me filling her up. Every inch of her moved to get the most pleasure out of me. After fifteen minutes of riding me on the couch, Josephine abruptly stood up, turned around, and lowered herself back down on my member. She squatted forward and rested her hands on my legs before returning to the ride she had started.

"God damnnnn," she moaned as she rode me in a sitting reverse cowgirl. From that angle I got an incredible view of her petite, teen ass. I could appreciate the visual stimulation of seeing my massive prick get absorbed by her impossibly small twat.

After another ten minutes of her efforts, Josephine's moans stopped and her body began to tremble. My fresh new sugar baby was beginning to climax on my manhood. She shook for 20-30 seconds before another wave of her already ample juices gushed onto my shaft. She let out a ferocious moan that sounded like it was half agony, half ecstasy. After a minute of soaking in her orgasm, Josephine collapsed backward onto me, with my cock still engulfed by her satiated inner walls.

Once Josephine caught her breath I scooped her delicate frame up and aggressively rolled her onto her back. I reinserted myself into the vice-grip teen pussy I had purchased just that morning and began pummeling her in missionary on the couch. After a few minutes of kissing and fucking the hot little number underneath me, I leaned up and pulled her legs along my torso so that her feet were over my shoulders. I leaned forward and got several inches deeper into her.

Josephine reflexively pushed me away as I performed what some called the "womb rocker" or "anvil" position. I grabbed both of her hands and pinned them above her head and then laid even harder into her teenage womb. She began screaming in both delight and discomfort as I ravaged her and pinned her to the couch. I lasted longer than I usually would have under those conditions, having already cum twice that day. Watching her face squirm underneath my attack sent me over the edge again. I felt the familiar storm build inside my balls and moments before I reached the point of no return, and much to her surprise, I pulled out.

I guided the tip of my cock to just a few inches above Josephine's sweet, unsuspecting face. My other hand held her wrists above her head and the weight of my body kept her minuscule frame pinned.

"Open your mouth," I said. Josephine dutifully complied and stuck out her tongue, waiting to lap up the treat of my third orgasm. I pumped myself a few more times with my free hand and began unloading stream after stream of cum. Most of it landed in her hair, over her eyes and cheeks but some fell into her waiting mouth. By the time I was finished, a gorgeous, recent high school graduate had a face of my jizz as her reward. After taking in the sight of it all, I too collapsed onto the couch.

Josephine carefully wiped her eyes and looked over at me. "Well... I hope you don't mind if I use your shower, sir."

***

After another glass of wine I escorted Josephine to the shower of my master bathroom. It was a large, tiled rectangle with five nozzles on the wall and a rain head faucet on the ceiling. A tiled bench was set into the side opposite the main wall. Josephine and I hopped in once it was sufficiently steamy and began cleaning off from our two exquisite fucks.

She first rinsed her cum-covered face and ran my shampoo through her hair. Watching the suds cascade down from her auburn locks to the nubile, tight body below stirred something in me again. I picked up a nearby bar of soap and began running it over Josephine's tiny frame. She giggled and looked up at me, keeping eye contact as I massaged the soap into a lather across her breasts and taught stomach. Once there were enough bubbles to make the soap irrelevant, I spun her around to face the bench of the shower. I worked the lather from her front down to her toned quads using both of my hands. Given our height difference, I had to kneel down onto the floor of the shower to work the soap down her legs. She placed both of her hands on the wall of the shower, leaning over the bench.

At that angle I had a perfect view of her firm little butt, defenseless asshole, and the sud-covered lips of her twice-ravaged pussy. After working down her legs my hands trailed back up and began massaging her teen cunt with one hand. I let my thumb glide over her sphincter and apply just a hint of pressure. She obediently took my attentions to every inch of her body. When the steam and sweat had rinsed the suds away, I bent her further over the bench and her pulled her tiny hips back to completely expose her delicate folds from tailbone to clit.

Once Josephine was in the position I wanted, I leaned forward and began greedily licking her most intimate places. She gasped and moaned, she instinctively reached back and placed one hand through my hair - urging me on. In many ways that signified her controlling me, but I felt turnabout was fair play in this regard. Certainly I could still breathe, a distinct difference to when I choked her with my cock. Plus her 18-year-old pussy had the taste of absolute perfection.

After a few minutes of dispersing my efforts across both of her holes, even venturing a brief insertion of my tongue into her ass (which sparked a squirm and sexy giggle), I focused all my attention on her lovely, engorged clit. Four or five decades of experience and I felt as though I could teach a master class on eating a woman out. My ego was proven worthy when, after only four minutes of dedicated intent, I felt her legs begin to tremble and she gripped her fingers in my hair.

One thing I loved about her so far: when she began to cum her moans stopped and she went dead silent until the pinnacle of her climax. After thirty more seconds of my tongue stimulating her pussy she exploded. A loud, satisfied moan. She released my hair to slap the tiled wall and pressed her hips further back to buck against my face. I slowly reduced speed and then took one final lick from her mons to her lumbar region, stopping a moment to savor her virgin butthole again.

When I stood up, she turned around and had a look of complete satisfaction and total exhaustion in her eyes.

"Wow," she said, "I didn't know that would be so amazing." I looked at her curiously.

"Best ever?" I asked. She nodded vigorously and returned to the main stream of the shower.

"I thought I liked getting oral," she said, "I didn't know I loved it. I guess I just needed an experienced, older man to get me off!"

I gave Josephine a mock salute, "Well I'm happy to serve." It was the perfect conclusion to our first night together.