Unexpected Sugar Daddy Pt. 05 – Anal – Free Sex Story

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Weeks passed and Josephine started the rigorous college program I was paying for after she completed her summer internship. The sexy little vixen would often stop by around lunch or the late afternoon, occasionally we would have dinner, and I wanted her to have the full college experience so we rarely spent every weekend together. Those weekends where we did connect it was usually only for a night and morning.

Some of my favorite early encounters with Josephine took place in the summer months after our arrangement was made and when she initially started classes. She was a perfect addition to my lifestyle.

One Sunday afternoon when I was working in my garage, Josephine arrived in her jeep wearing a white t-shirt, cutoff jean shorts, and a pair of black sandals; with her hair tied in a messy bun. Upon her unannounced arrival she pulled me into the garage and before the garage door was even down she was on her knees sucking my cock. I tried to warn her I was sweaty and unwashed from my landscaping and weekend chores but she didn’t even respond, she just gobbled up the willing member before her.

After she had deepthroated me for several minutes I pulled her up to her feet and yanked her daisy dukes down to her ankles in one swoop, revealing her perfectly waxed, teenage Pussy and the fact that she was going commando. I pulled her up into my arms with her little white t-shirt still on and fucked her in midair. Josephine gasped as she was taken like a rag doll by the strong older man she had come to seduce. I used her tight little body for several minutes standing in my garage and then laid her on my workbench on her left side and fucked her from behind, sideways, while I was standing up. Knowing she had come (unrequested) to get it from me, I railed her wet fuckhole as hard as I could and when I felt the familiar stir in my sack I grabbed a fistful of her hair and yanked her head back while I released my cum deep into her womb. Josephine came hard on my cock and left with only a “Thank you, sir!”

A week later, Josephine took an Uber to my place late one Friday after a frat party. She arrived in a little black dress and heels, with her hair down… makeup and hair done to the nines. When she arrived, more than a little tipsy, I scooped her up and carried her into my bedroom. Once I had her dress off and admired the lacy black thong she was wearing, I laid her down and serviced her with my tongue for over half an hour. She came twice before I finally got inside her. For another half hour I pounded my teen sugar baby with her feet over my shoulders and unfettered access to her tight Pussy. When I was finally ready to cum I surprised Josephine by pulling out and Cumming on her pretty teen face. She surprised me by pulling the globs of semen off her face and licking them off her fingers for my enjoyment.

One of my favorite times though was when I invited her over to watch college football one Saturday. She showed up in her black yoga pants and a sporty, grey tank top. Josephine surprised me by making me an intricate sandwich, bringing me a beer, and immediately sinking to her knees to blow me while I watched the game, ate the sandwich, and drank in my favorite chair. For twenty minutes I savored the food, view, and 1st quarter while Josephine serviced me. As usual, when I was ready, I wrapped my fingers in her hair and held her in place while I came down her throat until she gagged, and then I customarily let the rest of my load spill out over her tongue.

By October I was completely satisfied with our arrangement. We would occasionally go on dates, visit art exhibits, or spend some lounging time together. When she told me she had a week long fall break though I immediately sprang into action.

“What are you doing for Fall Break?”

“Nothing,” Josephine said, “My friends are pretty much just going home for a few days or camping. I don’t want to camp in the fall – too cold.”

“Go somewhere warm,” I replied. She stuck her tongue out at me.

“Everywhere warm is pretty expensive, sir,” Josephine said. I smiled and nodded.

“Well how about I take you somewhere?” I asked. She lit up at the possibility.

“Where??” she said.

“Let’s go to Hawaii,” I said, “I’ll take you to Maui. Or any of them really but I know Maui and the Big Island the best.”

“Really?” Josephine asked.

“Yeah.”

“What do I tell my dad?”

“I don’t know,” I laughed, “Tell them you ended up going camping. You won’t have cell phone access.”

Thirty minutes later we had booked our flight, picked a hotel, and Josephine was riding me in my office chair to say thank you.

* * *

Ten days later I had Josephine on my arm as we arrived on Maui. Sitting next to her on the plane in her black, skin tight leggings, blue converse, and yellow tank top had been absolute murder. Similarly unpleasant was the flight attendant referring to me as Josephine’s dad. She teased me by calling me “daddy” the rest of the flight.

I wanted to rip her clothes off the entire time and goggled at her supple thighs, crossed in her seat as she read a book, for hours. Knowing full well she had been forbidden underwear during the trip and had been waxed the day before in preparation for the Hawaiian sun.

I had sprung for a villa in Kihei at a nice resort; it was a one bedroom in white stucco that overlooked the ocean. The concierge gave Josephine and me a curious look as he realized we were staying in a one bedroom and had a staggering age difference.

The moment we walked in I pressed Josephine against the wall, hand on her neck, and gave her a passionate kiss before working down her neck. I licked the point where her neck met her shoulders and savored the salty taste as she giggled.

My hands ran down her lean torso to rest on her hips as I pressed my full weight against her, pinning her lithe frame against the wall.

“Someone’s eager!” Josephine teased. My hands ran over her tight rear and gave both cheeks a squeeze.

“I’ve been ogling you through four time zones,” I said cooly into her ear. My hands maneuvered so that one went down the back of her pants to play with her Ass and the other went down the front to rub her smooth, teenage mound. She clutched my back as I stimulated her erogenous zones until she was soaked and ready for my incursion.

I lifted her tank top over her head then swiftly pulled her leggings to the floor. She stepped out of them, leaving them in a pile in the entryway, but remained in her blue converse.

I scooped Josephine up in both arms and carried her into the living room. Without another word I pressed her down onto the large Tahitian area rug, unzipped my pants to expose my fully erect cock, and pummeled my tight little piece of Ass for an hour. Josephine took me in missionary, doggy style, reverse cowgirl, and back to missionary until I finally pulled out and released stream after stream of cum onto her sweaty, spent, and petite body from nipples to her smooth mound.

The next day was, if possible, more excruciating than the airplane ready. I wanted to mount Josephine from breakfast to dinner. We grabbed coffee and a bite to eat at the resort restaurant then went back to our villa to change. When I next saw Josephine she was wearing a blue, thong bikini with gold metal accents. The bikini left almost nothing to the imagination, which was perfect for me to soak in her fit, lean, young figure all day.

When we got back to the room that afternoon I started flirting with Josephine, pinching her cute little bare Ass and kissing her neck. For the first time ever she pushed me back to reject my advances and puckered her lips at me.

“Not yet you dirty old man,” Josephine said, “I have a surprise for you later.” I didn’t mind the delay, she was worth the anticipation.

* * *

That evening I was ready for dinner, waiting in the living room for Josephine to finish getting ready. When she finally emerged my cock sprang to life. Josephine, my 18-year-old sugar baby, was standing in the doorway in a blue sundress with yellow floral-themed embroidery that came up scandalously high. It was made of a light, wavy fabric and clung to her in the right places while flaring out to catch the breeze. It showed just a modest amount of cleavage but exposed her entire, lean back… down to her back dimples.

Her hair and make up was done exquisitely and she was wearing wedge heels made out of cork and a lacy, white toe strap. She looked incredible and her skin had an after sun glow. I wanted to fuck her so badly.

My jaw dropped and she knew it.

“What??” Josephine asked, blushing a bit.

“My god,” I said, “That is a nice dress.”

“I’m glad you like it,” she said, “I expensed it to you.”

“Ohhhhh…” I teased her, “So this is my dress then?” I pulled her close and ran a hand down her back until I had her dress-clad, firm Ass in my hand.

“Sir,” Josephine said, breaking our embrace a bit, “I have a surprise for you.” She looked up at me doe-faced.

“What is it baby?”

“Well,” Josephine started… showing a little embarrassment, “Taking me on trips was not part of our arrangement. So I wanted to do something to say thank you.” Josephine bit her lip and stepped closer to me again, looking up into my eyes.

“I asked around for advice,” she continued, “The girls on the cross country team had answers that ranged from ‘You don’t owe him for taking you on a trip!’ to things like ‘A realllly good Blowjob.’ And I felt like I already give you really good blowjobs orrrrr you already fuck my mouth exactly how you want to anyway!” Josephine took my hands from her waist and cheeks and pulled them under her short dress to rest on the bare skin of her Ass. She was continuing to abide by the underwear embargo for the trip, even with a mini sundress on.

“So I asked a friend of mine in a sorority for ideas,” Josephine said as she wrapped her arms around my neck and pressed her lean body against me. “She had to go ask around and came back with answers that ranged from ‘You don’t owe him for taking you on a trip!’ to answers like ‘Let him fuck your Ass in Hawaii,’ ” Josephine stood up on her toes to place her mouth closer to my ear.

“Well sir,” she said, “I do feel like I owe you a lot. You’re taking care of me, giving me the best Sex I’ve ever had, I Love Cumming on your cock, and I Love spending time with you… and I also know you don’t have to do any of it and you definitely did not have to bring me here.” Her voice dropped a little lower and quieter, “So I wanted to ask if you would fuck my Ass tonight… so I can say thank you…”

She came off her toes to return to her usual, heel-clad height, and continued to look up at me.. biting her lip. My hands were holding the firm, petite Ass I would be having as soon as possible. Before I could answer, Josephine placed a finger on my lips.

“There’s just one thing,” she said, “We still have to make our dinner reservation and I want you to wine and dine me knowing the whole time we’re at the table that you’ll be bending me over and fucking my Ass later tonight. I’ve never done it and I think teasing you a little bit is really sexy.”

With my heart pounding I mustered the strength to say, “Lead the way,” instead of pounding her into the villa floor.

Josephine took my hand and walked me out of the villa, across the resort, and into the beautiful Hawaiian evening. The ocean breeze caught the hem of her sundress every so often and exposed another inch or two of her tanned, toned thighs. I was in heaven. I could not wait for the rest of the evening.

At dinner we settled in at a high top table which gave me an excellent view of Josephine’s legs the entire time. Knowing she was panty-less beneath her sundress and that I would have unlimited access to everything beneath her dress that night kept my cock on alert the entire meal. A few of the patrons stared at us: a couple with an obvious age difference. Some were skeptical, the men were jealous, and a few seemed to satiate their interest by telling themselves we were father and daughter.

Knowing I had to endure the length of the dinner, and wanting to play it cool for Josephine too of course, I chatted her up about her plans for her next pieces of art. Even suggesting she paint something inspired by Hawaii. She curtly replied she already had a plan for a Hawaiian-inspired piece, but she didn’t want to discuss it yet.

Josephine had brought her fake ID on the trip and drained two Mai Tais before the entrees came. I couldn’t help but feel she was getting herself in the mood for the anticipated encounter. We ate, drank, and laughed next to the Maui sunset.

The check came, I paid, and whether the waiter noticed or not that I leapt from my chair to take Josephine’s hand and scurry her out of the restaurant was anyone’s guess. Five minutes later we entered the villa and I practically threw her against the wall and began kissing her neck.

Josephine giggled and ran her hands up my sides before pulling me in closer to her lithe frame. Before I could take control of the situation any further, Josephine slid down the wall to rest on her cute Ass, her knees up, and her smooth teen Pussy exposed beneath her dress. She looked up at me longingly as she unzipped my pants and reached in to grab my cock. I could not recall a time that she initiated oral while sitting instead of kneeling.

My fully erect member came out of my pants and I had to squat a fair bit to position myself level with Josephine’s mouth. She was stroking me while I did and the way she bit her lip drove me crazy.

“Fuck my mouth, sir,” Josephine said softly. She let go of my shaft and placed both her hands next to her on the cold tile beneath us. I leaned forward to press myself past her lips and let my right hand grip onto her head. Josephine kept her eyes locked on mine and moaned when I pushed past her tonsils and into her 18-year-old throat.

This girl was perfect. That’s all I could think of as I slowly, methodically used her pretty face. If I didn’t know what was in store for me I would have surely cum in her mouth. After ten minutes of gagging Josephine on my much older prick I picked her up and pressed her against the wall again. This time my hand went under her dress to play with her bald, soaked Pussy.

“What next?” I asked. She playfully nibbled on my neck while I fingered her, then pushed me back to guide me into the living room. A wicker sofa stood in front of a bay window with a gorgeous view of the early evening ocean. Josephine stopped to pull something out of her bag then turned to me.

“Here,” she said, handing me a bottle of lube. She then turned and pulled her sundress up and off her lean frame before sinking onto the sofa on her knees, facing the bay window. She still had her lovely wedge heels on, and nothing else, and stretched herself out so her cute little Ass was pressed back for my viewing pleasure.

“Do whatever you want with me, sir,” Josephine said, looking over her shoulder, her hands gripping the top of the sofa. I stepped forward, still wearing my tropical button down and slacks… with a fully attentive cock sticking out toward Josephine’s nubile body. I stepped forward and ran my hands over her back, gripping her Ass, and even roaming over the backs of her legs and calves as I admired the beautiful teen Ass and perfectly waxed lips below… waiting for my attention.

I ran my cock up and down Josephine’s Pussy, coating myself in her juices, before plunging forward into her tight, 18-year-old cunt. She gasped as my full length and girth forced its way into her submissive folds. I grabbed her hips with both hands and slowly fucked my sugar baby while taking in the night sky and ocean below it. Once I had enough of the ocean view, I looked down to ponder the defenseless Ass at my disposal. Her cute little rosebud did not look as if it could possibly fit me… but it would.

I opened the bottle of lube Josephine had provided and poured a glob into her tiny crack. She giggled a little and told me it was cold. I used my thumb and forefinger to massage some of the lube around her tight hole and into my little nymph’s sphincter. She gasped when I buried my thumb into her Ass to the knuckle and then almost laughed and sighed when my whole thumb proceeded further in. I rhythmically fucked Josephine’s virgin Ass with my thumb for a minute to get her accustomed to the sensation. She moaned a little and gripped tighter onto the sofa.

Once I thought she was ready I pulled my cock from her tight teen twat and coated my tip in the lube still sitting in her crack. Without any other fanfare I pressed the head of my eager member slowly into her Ass and waited for the natural resistance of her sphincter to give way to my incursion. Once her body had given in, the next two inches of my cock slid effortlessly into her Ass.

Josephine gasped and pressed herself ever so slightly back into me, sending another inch of my shaft into her tight hole. I savored the delicious sensation of the vice-like grip of her teen rectum and then pulled out to the tip, only to plunge back into her. Josephine moaned, clenched her hands tighter, and chuckled a little as I began fucking her tail. She was an Anal virgin no longer.

Before I got further into my treat, I took in the scene. A Hot college freshman beneath me and the moonlight starting to reflect on the tops of the Hawaiian waves through the bay window.

I ran my hands up her back to rest on her shoulders and held her in place as I picked up my rhythm. Once I was confident she could take it, I proceeded further into her butt – just over half my cock was in her. I looked down to see her toes curled inside her heels and the top of her head rested on the top of the wicker sofa.

“Are you ok?” I asked.

“Yeeessss!” Josephine moaned in reply. “It hurts a little… but I want it sooo bad, sir. I can’t believe you’re fucking my Ass like this.”

I picked up the bottle of lube and poured another globule onto my shaft. As soon as the new lube was spread out Josephine began moaning noticeably more. She let one hand off the couch and brought it down to play with her clit.

“Yeah babe,” I said as I continued fucking her Ass, “Play with yourself, honey. That’s so Hot.”

“Yeah??” she said as she began pleasuring herself. “Do you like that, sir?” I held her shoulders firmer and pulled her back into me, leaving only an inch or two of my cock out of her petite rear.

“Keep going,” I said as my right hand found her hair and pulled her head back, driving the last inch of my cock into her. I could feel just how tiny she was as my cock filled her most intimate hole. The way she was moaning I was almost certain I was banging her G-spot through her Ass, at least triggering it enough for her liking.

After a few minutes of playing with herself I felt Josephine begin to shudder.

“Babe!” she said, “Babe… you’re gonna make me cum so hard!” Fucking the feral piece of Ass below me was too much. As soon as she peaked in her own Orgasm I lost control and pummeled her Ass harder. After only a few piston-like thrusts into her, my balls tightened and I sank a huge load of cum into Josephine’s waiting Ass.

Her whole torso fell, exasperated, onto the top of the couch as she took my seed. She was breathless and still enjoying the come down from her own climax. Meanwhile I was using her Ass to milk my cock of every last drop. Once we caught our breath I carefully, slowly pulled myself from her butt. I collapsed on the sofa and she turned to straddle me, sitting in my lap and facing me.

She looked adoringly into my eyes and I had to admit, I was developing feelings for her.

“Holy shit!” Josephine said, “I don’t think I’ve ever cum like that.”

“Was it ok?” I asked. She placed her hand on her head and closed her eyes.

“It was amazing,” she said, “It burned too but holy fuck. I could learn to like that… a lot.”

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