Unexpected Sugar Daddy Pt. 07

The following Saturday I got a text from Josephine at 8:00pm. We had only seen each other once that week, a lunch on Wednesday and no sex. I had to entertain clients on Friday night and she had told me she was occupied with a study group on Saturday, so we made plans to see each other for Sunday brunch before she had to return to her sorority house for chores.

So when Saturday evening rolled around and I was alone listening to vinyls, I was surprised to hear from her.

'Hey would you be willing to help me with something?' she texted.

'Probably!' I replied. She sent me back an emoticon with its eyes closed and tears shooting out of the sides.

'I need help with a piece of furniture in my dorm,' she wrote. I raised my eyebrows. I had never visited Josephine on campus before.

'Don't you think I'll look suspicious in a dormitory of freshmen college students?' I asked.

'Yes you will,' Josephine wrote back moments later, as if prepared for the concern, 'I think I can make it worth your while though...'

'Alright, alright,' I replied, 'Do I need to bring any tools?'

'Just your muscles.'

Ten minutes later I was in my car and plugging Josephine's dorm address into my phone. My mood was that of a man who was really looking forward to finishing one to two more records and falling asleep, and was then suddenly asked to visit Ikea. At least Josephine was fun to look at and it seemed that at least a little entertainment might be in store for me. Though how I was going to give, receive, or take any sexual favors with her roommate present or a floor full of students around was a mystery.

Twenty minutes of thinking about Josephine, while finishing the vinyl I had interrupted on the far less satisfying bluetooth connection to my car, and I was on campus. Walking from the parking lot toward the dorm I encountered a pick up frisbee game in the dark, a handful of alternative-looking coeds on their phones on the steps up to Josephine's dorm, and a few tipsy 19-year-old boys on the prowl.

When I entered her dorm hall a very cute redhead girl sat behind a welcome desk reading "Introduction to Art History." Her nametag read 'Mindy.' She was wearing a green t-shirt and dark blue jeans, it was clear to all who saw her that she had no bra beneath her shirt despite the rapidly cooling fall weather. Her nipples were sticking through the thin material unrestrained. What I noticed most about her though was that she had trimmed her dark red hair into a bouncy pixie cut and her skin was absolutely porcelain, most noticeably on her high cheekbones.

Mindy's entire facial package was rounded out by an elfin, pointed nose and pale white lipgloss. When she looked up at me, something about her eyeliner and the glimmer in her crisp, green eyes told me she was a real treat in the bedroom. Her lips looked like they really knew their way around.

I was very satisfied with my arrangement with Josephine. But the caveman in me wanted to wrap my hands through Mindy's pixie cut and choke her on my cock.

"Good evening," Mindy said, "Who are you here to see?"

Before I could answer, Josephine stepped through the locked door into the dorm lobby.

"Hi, Daddy!" Josephine exclaimed, wrapping her arm through mine and leading me back into the dorm hall. "He's with me, Mindy." As Josephine led me away I absentmindedly turned back to look at Mindy, perhaps to see if she needed anything. To my surprise I caught her eyeing me up and down after (incorrectly) determining I was Josephine's father.

I turned my attention to the task at hand and followed my sugar baby down the hall and into an elevator. Once the doors of the elevator were closed, Josephine took me completely off-guard by turning into me, wrapping her arms around my neck, and passionately kissing me as we rode up to floor twelve.

It wasn't until Josephine pressed her lean, young body against me that I appreciated what she was wearing: tiny grey cotton shorts that exposed her tan, toned legs, a pair of brown UGG boots, and an oversized blue hoodie in her college's livery. She looked like the cliché of a freshman college girl. Her makeup was lightly applied and her hair was entirely contained in a messy bun.

I ran my hands down the back of her hoodie and pulled the material up so my hands could explore her lower back. By the time I made my way up to her shoulder blades to discover she was braless, the elevator door opened and she led me out into her dorm hallway.

Following Josephine closely to observe her cute little ass twitch was a treat. Her shorts appeared to be simply grey sweatpants that had been hemmed so high up her thigh they could almost be lingerie. I was suddenly reminded of why I would drop my quiet evening to help her with furniture at a moment's notice.

She led me past a dozen or so doors, we only encountered a headphone-wearing freshman boy on our way. He tried to conceal that he checked Josephine out via a sideways glance but I, a far more seasoned hunter than the freshman, caught the subtle act. It was no surprise to me that Josephine had captured, or would capture, the attention of any straight man she encountered.

Once we were inside her dorm room, Josephine again rounded on me and kissed me. I was pressed up against her door with a thud and broke our kissing only to check the room for her roommate.

"Are you alone tonight?" I asked. Josephine stepped back, coming off her tiptoes as was required for her to kiss me if she was unaided by heels.

"I am!" she said, "My roommate went back to her parent's house for the night."

"Ah!" I said, "So what do you need help with?" Josephine's eyebrows went up and she spun on one foot to guide me further into her dorm room. At a glance it was pretty much the same as what I experienced in college: cinderblock walls painted white, two twin beds, two desks. A chair, TV, and grimy area rug were scattered about, with a mini fridge in the corner. Unlike the days of old they had their own small bathroom instead of a communal, coed facility on the floor.

"I need help with my bed," Josephine said, standing next to her neatly made, prison-sized mattress. I scoffed at her slightly.

"Oh," I said, "What's wrong with it?" Josephine pranced toward me in two swift steps before again rising up on her toes to kiss me. When she was done she rested flat on her feet and looked up at me longingly with a gleam in her eyes.

"I haven't been fucked on it yet..." she said. "... I think that's a real tragedy in my college experience thus far."

"I see." My hands fell to the waist of her shorts and both of my thumbs started trailing underneath her waistband. I loved the way her trim obliques tucked neatly into any pants she wore. As my thumbs, and then forefingers, begin exploring the flesh beneath her shorts it became clear Josephine was not wearing any underwear.

"What would you do to me if you were here?" Josephine asked.

"Am I not here?" I said. Josephine giggled and grabbed my hands.

"No," she said, "Of course you're here. I mean what would you do to me if you were here like you're supposed to be. I mean... well... we're exclusive right?"

"Right," I said, still not understanding.

"Well then I won't ever get to experience what it's like being a freshman girl in college," Josephine said, "And bringing a guy back to her room that she wants to fuck."

At that, Josephine dropped to her knees and began hastily unzipping my pants.

"So I'm asking you," she continued, "What would you do with me if you were the college guy I'm supposed to be hooking up with right now? If I brought you back here and dropped to my knees to pull your cock out..."

With that she retrieved my semi-hard, but now rapidly growing, member from my jeans and began stroking it over her face. Her auburn hair in its bun, while Josephine looked up at me about to pleasure my cock, reminded me of the day we met. I grabbed the top of her head and pressed her forward until my head had brushed against her tonsils. She kept her eyes fixed on me for a few moments while her tongue curved to accept my shaft running back-and-forth through her mouth.

Josephine moaned and her hands dropped down to her thighs. She was letting me know I was entirely in charge of her now. What a treat she was.

I kept her head in place as I bucked my hips forward, fucking her mouth with intention.

"You want to know how a 19-year-old guy would fuck you in your dorm room?" I asked. Josephine moaned and nodded, unable to speak as I relentlessly used her pretty face. I pressed her backward until she came off her knees and lurched back onto her teenage ass, keeping my hand on her head. It took a moment to move her into position, but I eventually pressed her head back to rest on the wood frame of her bed behind her while my eager prick took care of her front. She was trapped between me and her bed, with me lodged in her throat.

Her hands alternated between resting on my thighs and clutching the rug beneath her as I continued to use her throat for my pleasure. I kept going until her eyes watered and her eyeliner ran, ever so slightly, down her cheeks. Josephine kept her eyes fixed on mine as best as she could under the circumstances.

Once I felt I had made my point, I picked her up from under her arms and pulled her to her feet. She was taken aback but did not have time to adjust before I pulled her college hoodie up over her head, disheveling her bun even further. With her hair out of sorts, I pulled her knots out and let her long hair fall down to its usual length at her lower back.

Rather than kiss her I spun her around until she was partially bent over her own bed. I took a moment to appreciate her firm cheeks yearning to break free of her shorts. I ran my hands over the material a moment and gave her a playful slap on the ass before pulling her shorts down to her ankles.

Without another word my right hand trailed down her back, over her ass, and rested on her outer lips. I massaged her waxed-smooth pussy for about a minute before finally inserting one finger into her wet little hole. Once she was ready I let another finger slip into her and I began massaging her vaginal walls.

"Is this what you want, baby?" I asked. She nodded, biting her lip as I started to finger-fuck my beautiful, young mistress. To finger a girl was a young man's game. I would have much rather gone down on her, bringing my decades of experience to bear. Her peers were not there yet. For every one college girl that had a male classmate bring them to orgasm orally, three more college girls got fingered by an idiot until his patience ran out. Today, at Josephine's request, I would be playing the part of the freshman boy.

Still, even if I was expected to give her the experience of a sloppy college hook up, I could still do it to the best of my ability! After decades of trial and error I certainly knew how to use my fingers to illicit the best response. And my efforts were rewarded.

Josephine moaned and dropped her head as I applied deliberate pressure toward the front of her g-spot, combing the huge cluster of nerve endings that connected her clitoris to her pelvic muscles. I felt the the response I wanted: she began soaking my fingers in her juices.

"Oh... fuck!" Josephine exclaimed as I applied even more pressure against her g-spot, curling my fingers into the front of her vaginal canal from behind. When her legs squirmed I decided she had received enough. A freshman would never take her to her apex with his hard cock already sucked, hanging out of his pants, as she stood there bent over her own bed.

I stood up fully and in one swift movement inserted my full length into Josephine from behind, with her shorts still wrapped around her ankles and boot-clad feet. She slapped the cinderblock wall and bit her lip.

"Oh fuck me... please fuck me!"

I grabbed her hips and began hammering into her wet, tight pussy, taking note that she was more lubricated than usual from the attention of my fingers. She liked being fingered! Who was I to say no? I filed that information away for future use.

Josephine grabbed onto my right hand with hers, urging me to go harder. I clenched my nails into the flesh of her hip and my left hand moved up to wrap around her throat. She drew in a sharp breath as I took control of her neck.

"God you feel good baby," I said as I continued to pound her. I took a moment to admire her tight little ass slapping back against me, practically begging for more of my manhood.

After several minutes I pulled her shorts off her ankles, pressed her slightly onto the bed with her left foot still on the ground, her right leg splayed over the bed, and her torso resting face down on her mattress. At that angle I could drive even deeper into her. Josephine responded by curling her fingers through her sheets and moaning into her pillow. After only a dozen or so thrusts I felt the familiar preamble to her orgasm: a violent tremble that seemed to emanate from her lower abdomen.

Her pussy contracted and her hips bucked against me hard as I kept thrusting into her. Eventually her whole body trembled and she practically screamed into her bedding before going limp.

If I was a method actor and had lost myself in my role of the late night hookup, then I would have cum right then and there. Sadly I was still her older, experienced lover.

I flipped Josephine over onto her back, pulled her boots off, and climbed on top of her. She spread her legs at the perfect time and then wrapped them around me as I settled in above her lithe frame.

With Josephine's feet, calves, and thighs urging me on I pressed forward and re-entered her. My hands explored her upper body for a few minutes before settling in with one hand under her head and the other clutched under her lower back. In that position I began burying myself to the hilt in Josephine before pulling almost entirely out, just to crash back into her. The wood frame of her bed shook with each thrust and her moans filled the room... broken only by an occasional, feral kiss.

I unfastened her legs from around my torso and pulled them up until her feet were almost next to her head. With most of my weight resting against her legs I resumed fucking Josephine at maximum depth.

"Oh my god!" she cried as I forced her to take my full length with her helpless young pussy lifted off the bed to be used at my disposal. "You're too big!"

Her hands found my upper chest and she tried to reflexively push me back, but I grabbed both her wrists in one hand and kept charging forward. The look in her eyes as I ravaged her sent me over the edge and after a few more violent thrusts I exploded into my coed's womb.

I let go of her wrists so that my hands could pull her toward me by the tops of her thighs and used her body to milk all the cum from my pulsating shaft. After savoring my orgasm for a full minute I finally collapsed next to Josephine, spooning her from behind while I gave her a series of intimate kisses on the back of her neck.

She giggled and said, "Thank you!"

"Thank you!" I replied, "If not for you calling me over I would be at home listening to Fleetwood Mac."

* * *

I woke up seven hours later still in Josephine's dorm room. I had undressed down to my boxers, Josephine got back into bed completely naked after our late night romp. We spent the whole night curled up on each other in her twin bed. It was the least comfortable sleeping arrangement I had experienced in a while, very on-brand for the college environment.

Given that Josephine's tight body, particularly her firm little bubble butt, were pressed against me all night, it was no surprise I woke up with a massive erection straining under my boxers. Most of my package was pressed against Josephine's lower back as she slept.

One of my arm's was resting partially under her pillow, I maneuvered it so that it came up and wrapped around her shoulders to keep her in place while my other hand reached beneath our sheets to break my cock free of its constraints. With my raging member in hand, I guided my tip between her soft thighs and started pressing it upward over her smooth lips. I was so hard it did not take long to find and penetrate Josephine's unsuspecting pussy.

She woke with a gasp as I pushed forward, pressing myself into the front of her g-spot from behind. The arm wrapped around her shoulders held her down as I began fucking her while we spooned. God she felt so good.

I used the hand that had guided me into her to reach around and rub her lower stomach and hairless mound. After appreciating her toned abdomen for a few moments my hand dove farther between her legs and I began to massage her clit. Josephine shuddered and moved her top leg up and back to allow me full access to her teenage twat. In between rubbing her I felt my shaft going in and out of her, massaging her labia and demanding her body accommodate my girth.

"Play with yourself, honey," I said, removing my hand and holding her hip to pull her back instead. "Play with yourself until you cum."

Josephine interlaced her fingers and reached down to begin masturbating while I pounded her; she began pressing harder back into me as she worked to get herself off. Her moans grew louder and I summoned my patience to not cum until she had satisfied herself with my cock buried inside her.

We spent ten more minutes enjoying each other during our morning sex before she finally bucked her hips forward and backward and squirted onto my shaft. Josephine bit onto my forearm as she came to keep herself from waking the entire dorm. When she finally came down off her high I gripped onto her frame tightly, turned her to lay facedown on the bed, and plowed her for all she was worth.

Josephine's feet went into the air as she bent her knees, a reaction to the blunt force I was inflicting on her. I was sure it was a lot of cock at that angle, but she still pressed her hips back against me. She was coaxing me to go as deep as I could. That's when I got my wonderful, awful idea.

My sugar baby had squirted a pint of her juices onto me and I was as hard as I could ever possibly be. At the moment I felt my orgasm build I pulled out of her 18-year-old pussy and in one swift, decisive motion pressed into her undefended ass.

Josephine yelped and squirmed beneath me as I thrust in and almost entirely out of her ass several times, but much to her relief I almost immediately started blowing my load into her unprepared rectum.

I pulled her hips back onto me and saw her bite her lip as my shaft took another inch or two of her ass. I groaned in ecstasy as I pumped the last of my cum into her, then pulled out of my little slam piece and collapsed onto the bed. Josephine turned to curl up against my chest.

When I finally caught my breath she broke the silence.

"Well then..." She said. "That's one way to start the day!" I kissed her forehead and basked in the contentment that washed over me.

"You wanted the dorm sex experience," I said. "I think I should get an Oscar." I smiled and kissed her again before closing my eyes for a few more minutes of peace before we got out of bed.