Shaping Michelle

Life's twists and turns are never what one expects. When I decided to tutor young students in history, I thought I was just doing something good -- for the youth, and for myself. After several years of working at a Big Law firm, I decided I needed to do something that didn't involve poring over legal documents and old case law. I'd always loved and thrived in history, which was my major in undergrad, and I'd always pestered my professors with questions about legal history during my years at Harvard Law. Teaching wouldn't pay the bills, hence my pivot towards courtrooms and boardrooms, but it was something I thought would be a nice post-retirement gig. Many of my teachers in high school were former attorneys, which was quite common at Michelle's upscale preparatory school in Manhattan.

Michelle. One of those timeless, elegant names. The Beatles even used it for a song, though I don't think Lennon had a young, Asian girl in mind when he wrote it. Her family had been referred to me by a colleague, and over the course of her senior year I'd taken her from a struggling student to a pretty good scholar of history. She was no Ron Chernow, but she could at least articulate a good analysis of social movements in Victorian England.

When Michelle and I first met, I was struck by her beauty, but I wasn't necessarily attracted to her. She was tall and thin, but with a shapely form. Think of a swimsuit model. I think it was the fact that her mother was white while her father was Chinese-American. Michelle was a social butterfly, most definitely one of the "it" girls at her school. She seemed to have it all, or at least all that high schoolers cared about: good looks, pretty good grades, money, nice clothes. Lots of nice clothes. Michelle was something of an influencer; she wasn't going to be on The Today Show any time soon, but she had a healthy following of fellow preppy cool NYC kids. Vacations in the Hamptons, dining out with friends at the trendiest restaurants. If you grew up in the area, you knew the type. Although she would have been content to live that life forever, and her parents' money could certainly ensure that, her parents' values wouldn't entertain it. When the son of Chinese immigrants and a woman who went from her dad's small-town Ohio hardware store to a director's corner office at a major investment bank raise a kid, you better believe they'll expect that kid to at least get a degree.

Despite her seeming disinterest in academics, she was actually pretty smart; "just needs to apply herself more" was a common critique in her report cards. I guess I felt like somewhat of a kindred spirit in that regard; I'd only shaped myself up in college. Over the course of the school year, we'd developed a friendly rapport. Our tutoring sessions were pretty open-ended, and towards the end we'd end up talking a lot about life, her plans for the future, etc. I always saw myself as a mentor to Michelle.

Which is why what happened one summer day was... unexpected. I was spacing out in my office after a particularly contentious meeting with a corporate client when my phone buzzed.

"hey Milo, I hope this isn't weird but I wanted to know if you were available this weekend" read the grey chat bubble. I wasn't sure why she was asking me about availability -- she'd graduated high school a month before, and was enjoying her last summer before starting at Bowdoin.

"hey Michelle, what's up?" I replied.

Over the course of a few texts, she explained that she missed our conversations and she wanted to catch up and maybe talk about college and whatnot. It seemed a bit strange to me because we weren't necessarily on texting terms. We'd exchange messages just to set up tutoring sessions, but we weren't chewing the fat over text outside of that. But hey, who understands teenagers? I didn't have any plans that Saturday and figured it'd be nice to spend some of it guiding the youth.

"how about dinner at your place? I know you said you like to cook and I'd loooove to try something tasty" she responded, with that little emoji licking its lips punctuating the proposal. Now that was out of the ordinary. She wanted to have dinner? A coffee "date" was what I'd had in mind, but her message triggered something in me. Maybe it was the not-so-recent breakup I'd gone through, or pining for the lost days of my own youth, but suddenly I thought it'd be quite nice to have dinner with her. It'd be fun to whip up one of those Italian dishes that's dead simple to make yet impresses people, and maybe even flirt a bit. A pretty, fit, 18-year-old Asian girl batting her eyelashes at me would be enough of a reward.

I agreed and told her to come to my apartment at 7PM that Saturday. She responded "awesome!" and left it at that. I returned to my work and the next few days flew by me. Truly, I figured I would just be entertaining a young ingénue for a couple hours and assuring her that she was, in fact, smart enough for college (a repeated concern of hers during our tutoring sessions).

When I answered the door that Saturday evening, I was taken aback. Not for any good reason: Michelle was wearing a smart but modest top, short jean shorts, and wedge sandals. Her hair was done up in a pony, and she had well-applied makeup on as usual. This was her typical outfit. What took me by surprise was how I felt looking at her. Her breasts, probably a 32C, looked like two round mounds of heaven. Scanning down her lithe torso, I arrived at her shapely legs and hips. They looked great -- not necessarily muscular, but not lacking in tone (or skintone; she'd clearly been getting her fix of Vitamin D up in the Hamptons).

Of course, that all happened in a split second. I greeted her with a warm smile and let her in to my apartment. Taking a deep breath, she exclaimed "oh, something smells good!" There's nothing like a good spaghetti alla carbonara to tantalize the senses. As the dish was almost ready, I invited her to take a seat at the dining table while I put on the finishing touches. Two modest portions of the Italian classic sat tantalizingly on their plates as I sat down across from Michelle and poured myself a glass of wine.

"None for me?" she pouted.

"Well, I wasn't sure whether to offer, after all you're still a minor," I chided.

Of course, I knew that she drank. She was a recently graduated high schooler about to go off to college. But I still felt a bit uneasy about offering booze to her. After some pleading and puppy eyes, I relented.

"Just one glass for you, this isn't Beach Week" I teased as the cabernet sauvignon flowed into the glass. Taking a sip, she smiled and complimented my taste in wine before swirling it around and admiring the "legs." How I wished to say something about the much nicer legs sitting across from me.

Taking a bite of her food, she let out a loud "mmm" and dug in to her plate. I ate a bit slower, catching myself just mesmerized by this young beauty at my table. I didn't really know what was happening, but I was looking at Michelle in a way I never had before. She was no longer Michelle the Student, she was Michelle the Hot Young Chick. The cliche stirring in my loins began to fire up.

"God, I'm such a slut for pasta!" she exclaimed, stirring me out of my gaze and making me choke a bit on my food. I was not expecting to hear a word like that come out of her mouth, but I quickly saved face and said "hah, yeah, it's the best isn't it? I'm the number one 'thot' for pasta," chuckling as I used slang that was probably already outdated.

As we ate and chatted, both our inhibitions were loosened by the wine. The conversation gradually turned to college and I asked Michelle what she was most nervous about.

"Honestly... dating." This surprised me; I expected some nerves over academics, or balancing school with clubs and socializing.

"Really? I'm sure a girl like you would have no problem meeting a nice young man."

"I don't know... I haven't ever had a boyfriend. And guys don't ever seem to want to talk to me. They like my friends, but I've never even had a guy ask me out."

If there's one thing I've learned in my thirty years, it's that the most attractive women are often lonelier than you think. Guys are intimidated by smokeshows; they figure a 10 must have a long line of suitors and figure there's no way they'd have a chance. Anyone will hit on the girl next door, but talking to someone with literal model looks might as well be like trying to talk to God.

"I think you'll be fine, Michelle. You've got --" I caught myself briefly, trying to think of a diplomatic way to say it without sounding lecherous. "You're smart and well-read, you've got a charming personality, and you're an attractive young woman."

"You think so?"

"You don't? Aren't you an influencer? People don't follow you for fashion and makeup looks because you're not pretty, after all."

She blushed and smiled. "That's true. But guys my age are so obnoxious anyway. They're so immature. They're not like you, you know."

My turn to blush a bit. "Well, I'm a lot different than I was at your age, Michelle. I think guys might just be nervous to talk to you because they think you're out of their league. But you can be the change," I said somewhat jokingly, "and be the one that asks a guy out"!

"Hah! My mom always said a strong woman just goes after what she wants... but you think I'm out of guys' leagues?"

"Well, I don't really buy into the whole 'leagues' thing. That's a very naive way of looking at things. But I do think guys can be intimidated by a woman who's smart and pretty."

I poured myself another glass and decided to top her glass off as well. As the wine worked its magic on me, I started to amp up the flirting and banter. I figured it was a bit of harmless fun and would help boost her confidence. Clearing the plates, I told her I'd have dessert out and that we ought to sit on the sofa. She made her way to the living room while I scooped out a couple servings of gelato.

Taking a seat next to her, but not too close, I couldn't help but notice her beauty again. Her shorts had hiked up a bit, exposing almost all of those long, long legs. Her lips looked luscious as she licked the gelato from them between bites. I noticed her nipples poking through her shirt, no doubt caused by the strong A/C that was blowing over us, but quickly averted my gaze before she caught me. My eyes landed upon her wine glass, which seemed fuller than when I had left the table. The little minx had poured herself a bit more.

"Well, that was delicious" I proclaimed as I turned on my speakers and put on some jazz.

"It really was. Thank you for cooking for me, Milo," she responded as she took a big swig from her glass.

"Easy there, slow and steady" I said. We talked a bit more, enjoying the sounds of Coltrane's "Kind of Blue" as we worked on the wine. I excused myself to use the bathroom, and when I came back I noticed she had polished off her glass.

I sat down and she smiled at me. "I brought some dessert for you too," she said. What happened next was unimaginable.

In the blink of an eye, she moved around and swung one leg over my lap so that she was straddling me, and she immediately kissed me on the lips. Feeling shocked and a bit unsure of what the hell was going on, I didn't reciprocate, and then pulled away.

"What the hell, Michelle?"

"What?" she responded, somewhat curtly.

"We can't... you're my student --"

"I thought you found me attractive --"

"Yeah, I think you're gorgeous, but --"

"So just have some fun with me," and she went in for another kiss.

Blame it on the wine, or the breakup, or the fact that I had a hot, eager, willing young temptress on my lap, but something in me finally broke. This time, I opened up my mouth and met her kiss with vigor. Our tongues swirled around each other, engaged in a dance of lust and passion. My hands moved from my sides to her body, grabbing hold of her pert, tight booty. Her arms were over my shoulders, her fingers scratching my back. The smell of her perfume was intoxicating, and I felt like I was losing all sense of time.

As the kissing continued, our arousal grew. I was hard as a rock, spurred on by her hips moving back and forth, grinding her womanhood against my crotch. After what seemed like ages, I moved her off of me and had her sitting on the couch again, facing forward. We made out like horny teenagers (which made sense for her) while I decided to push things further. With one arm over her shoulders, I pulled her top down until her beautiful tits were spilling out over the shirt and bra.

It had been quite a while since I'd seen such perfection. For an Asian girl, she had pretty big breasts, with quarter-sized areolas and small, very erect, brown nipples. Using my right hand, I started to tease and twist one nipple, eliciting a sexy moan from the teen beauty.

"Does that feel good?"

"Oh... yes... yes..."

Drunk with passion, I then began snaking my other hand down along her taut, firm tummy and arrived at the waistband of her shorts. Deftly undoing the button, I then pushed down behind her panties and felt around for the real prize. As my fingers brushed her labia, she moaned. The little slut was soaking wet, and she began grinding her mound onto my hand as I switched from one nipple to another.

"You like that?"

"Yes... oh god..." she breathed heavily.

A couple fingers made their way into her tight hole, while my palm rubbed against her clit. I pumped my fingers in and out, and I could tell she was rapidly working her way to a climax. I was running on pure instinct at this point, and one of my instincts was to tease. I liked to work a woman up quite a lot before letting her cum, and I intended to do just that with little Michelle.

Her breaths grew shorter, and I pulled my hand away as she was preparing for the peak of pleasure.

"Oh my god" she panted, "oh my god..."

She reached over to me and pulled me in for a sloppy, horny kiss. This time she moved her hand to my pants and began to rub my dick, and I decided to help by undoing my belt and pulling my pants down.

"Have you ever sucked a dick before?"

"I did one time at this party last year... it was a stupid drunk hookup," she responded as she moved down to her knees. I didn't even have to ask her to do it, she just did it. Michelle marveled at my penis. I always figured I was a bit bigger than average, but not pornstar huge.

"His was definitely not as big though."

Michelle opened her mouth and greedily began to work her magic on my shaft. For a supposedly inexperienced girl, she was surprisingly adept at pleasing me. With a bit of guidance, she got the stroking just right while she teased the tip with her tongue, and she even paid attention to my balls.

"Oh... oh god, that feels fucking great" I told her.

"Mmm, you like it?"

"I fucking love it."

After a few minutes, she pulled away briefly to shed her clothes. She peeled away her shirt and undid her bra, letting those beautiful orbs hang freely. I had forgotten how perky and firm teen tits were. Standing up, she wiggled out of her shorts and tossed them aside unceremoniously before resuming her position on her knees. This time, she got very sloppy with the head, and within minutes she had covered much of her face in spit and pre-cum. I was approaching my own climax, and didn't want the fun to end with just a blowjob.

I pulled her away and asked, "where the hell did you learn how to do this?"

"Well," she blushed, "I watch porn. A lot of porn." God bless the internet.

I stood up and took off the rest of my clothes as well. We embraced and made out, passionately but not too intensely. I felt up her perfect tits and ass while she continued stroking my cock.

"Let's go to my bedroom," taking her by the hand and leading her to my quarters.

"Lay down on your back."

Michelle crawled onto the luxurious bed and turned over on to her back. My eyes drank up the tantalizing image before me. Michelle was no longer my student, she was my Venus. A sex goddess. Her long legs, her shaved mound, her lovely breasts, that cover model face. I noticed the tan lines around her pussy and on her tits and imagined her laying out in the nude to tan and take care of them.

"Have you ever been eaten out?"

"No..." she responded shyly. "But I need it."

I dutifully knelt at the foot of the bed, gazing at the perfect cunt before me. Shaved, as I had mentioned, with thin pussy lips and a small but aroused clit. Glistening with her womanly juices, ready to be lapped up. I dove in and began working her gingerly at first, teasing her folds and her clit with my tongue. I wasn't the best at eating pussy, but I knew not to overthink it: just explore their sacred part until you find what really flips the switch.

As my tongue darted around, Michelle began the climb up the hill of orgasm. Her breathing intensified, and her tunnel was practically flooding with arousal. Her moans echoed throughout the bedroom and I could feel her hands gripping the comforter. This time I made sure to take her all the way over the edge; I wanted her first oral experience to be one to remember. My fingers went to work on her clit, rubbing it frantically.

"Oh... oh... I... oh... OH... OH FUCK! FUCK!" she shouted as her body began to convulse, her mound involuntarily pushing back onto my face as she came.

"Fuck... fuck... that was... so good..." she panted deliriously. I couldn't help but feel a bit proud of myself for what I had done. Any inhibitions I had had an hour before were gone. Student and tutor, friend and mentor, all those relations were done. We were two horny lovers, and I decided to push for the final prize.

"Michelle, have you had sex before?"

The girl was still coming down from her orgasmic high. "No... I'm a virgin."

"Could have fooled me," which she chuckled at.

"Like I said... I watch a lot of porn. I've never had sex, though. I've never been with a guy I wanted to have sex with."

"I understand."

"But now I have. I want you, Milo."

I laid down next to her and kissed her and caressed her. We carried on the heavy petting for a few minutes and then I pulled away, turning over to grab my condoms from the nightstand.

"If you're not ready, we don't have to." I may have been horny, but I was still a gentleman, and I did not want to pressure the young girl into doing something she'd regret.

"I'm ready. I need you" she responded while looking me in the eye with the kind of gaze you only get from a woman who's ready to take you.

I quickly fished out the rubber and slipped it onto my cock. I stood up and walked around to the foot of the bed again, pulling Michelle a bit closer. I mounted the bed, spreading her legs as I placed the throbbing head at the entrance to her pussy.

Looking her in the eyes, I asked if she was ready. She nodded and I began to push.

Much like the perkiness of young boobs, I had also forgotten just how tight a fresh cunt could be. As my penis parted her, I could feel her tighten up. She was operating on another level of ecstasy. My head met her virginal wall, and we locked eyes again. I held one hand and she simply nodded.

Michelle let out a quick yelp as I claimed my prize. Her hand squeezed mine for a moment, and I made sure to give her a few seconds to adjust. Once her breathing slowed a bit, I kissed her passionately and began the ancient ritual. I slid in and out, in and out, maintaining a steady rhythm as I savored the tightness of her velvety walls against my dick.

"Oh... god... oh... it's... so... good..."

"Uh... uh... god... Michelle... fuck..."

As her vagina continued to loosen up to accommodate my shaft, I picked up the pace. I moved my arms to go underneath her shoulders, sort of hooking them with my hands. Her legs wrapped around my back and her hands were below my shoulders. As I pounded her harder and faster, she seemed to be pulling me in with her legs, while her nails began to scratch at my back.