Andy’s Rough Anal College Tale

Most of the below is true, and the sex is hot. Also: It's probably too wordy, it's certainly self-indulgent and there are some looong stretches between said sex scenes. But if you enjoy meet-cutes, decades-old college music and 20th century American literature along with true love, rough anal and multiple partners, this might be just right. Only looking to get off? Skip to the good parts.

*

"Fuck my mouth," Vanessa breathed, lips brushing my cheek and curvy young body molding to mine. "Then you'll fuck my cunt." Cunt. Emphasis on the "T." But she wasn't done.

"And then I want you to fuck my tiny ass," she whispered.

Hell yeah I loved her. Who couldn't?

Of course, that's not how it started. Not with my cock crammed up her tightest space. It began two years prior, when I finally found the courage to speak with the most beautiful person I'd seen in my eighteen years...

I was late for 20th Century American Literature. Again. But fate smiled upon me as I bounded down my dorm's stairs: The lust of my life and fellow Lit delinquent came rushing up from the women's floor. I opened the Draper Hall door for her and those milk chocolate-colored eyes, finally freed from cascading curls, destroyed me.

"Thanks!" she said with a wide smile. So she did speak. And cheerfully, too. I'd stared at her throughout our first year but barely had heard her voice.

Like me, Vanessa was attached. She dated some sullen artsy-fartsy type, and I was weaning off my high school sweetheart -- now 1,000 miles away -- and discovering drunken hook-ups.

"What'd you think of 'A Good Man Is Hard to Find'?" I asked, referencing our Flannery O'Connor assignment. Yes, I was that desperate for conversation.

"Haven't read it yet," she admitted matter-of-factly. "Should I?"

"Absolutely!" I answered quickly. Ugh, not so eager. "It's the funniest story you'll ever read about a serial killer."

She arched a brow, sizing me up while I silently scolded myself. Wooing women with serial killer jokes. Great start. I held my breath for a moment, hearing nothing but our shoes on the cement.

"Hey, thanks for saving me in class the other day," she said, still side-eyeing me.

"What?" Like I didn't know. Professor Hansen had hit her with something obscure from a lame-ass Steinbeck short, and I stepped in when she faltered. "Oh, that. No problem. Who gives a shit about Steinbeck, anyway?"

I checked my Casio. "Geez, I think we're gonna be late."

Vanessa turned to me as we cruised through the sun-drenched quad. "Do you care?"

"Definitely not at the moment," I said, shaking my head with a smile. OK, that was a little forward. My mouth moved way faster than my brain in those days. So did my dick.

"Well, Andy," she replied playfully, flashing a toothy grin. "What exactly does that mean?" I was pleasantly surprised for two reasons: No. 1, she knew my name. I never take that for granted. No. 2, she was intrigued.

"Just that it's hard to be in a hurry when it's so gorgeous out here," I said, making a show of breathing in the fresh air. Subtlety never has been a strength, but I wasn't lying.

Vanessa glanced over, probably ranking my cheeseball factor. She hesitated, and I worried I'd washed out. Then she leaned closer. "Maybe we should blow off class and go for a walk instead," she said, before covering her mouth with a dainty hand, big eyes widening. "Oh my god, I'm sorry! I just ate an onion bagel and I bet my breath is horrid!"

I assured her it wasn't; all I smelled was teen lust and spring blooming after a harsh winter. I handed her a piece of Big Red and we skipped, slipping off campus and down to the river.

Walks to the water became routine and I soon was smitten, swooning over her devious giggle, theatrical accents, razor wit and slammin' body. And I was hardly the only one who loved the latter -- all the straight boys and a bunch of girls (it was that sort of school) occasionally stared.

Hansen even perved on her while reading to the class from John Updike's "The A&P": The author's bikini-clad cutie had, according to the grocery-bagging protagonist, "the two smoothest scoops of vanilla I had ever known." The professor grinned and gaped over the page, ogling Vanessa's fabulous rack. Yep, Hansen was creepy. But he wasn't wrong. Except that my hottie classmate was blessed with doubles.

Vanessa and I grew tighter, she booted her imploding boyfriend and we verged on happening. There were sparks and flirtatious moments, but our lips didn't meet until the last night of first year. We were two of the few left on campus after finishing exams (do first-years still have the shittiest test schedules, or has the Internet made that moot?), and we shared dinner in the Union.

Later, sitting close in my dorm room, walls stripped of the cheap "Blown Away" print (remember that one? A dude and his speaker?) and Zeppelin and Uncle Sam "I Want You" posters, she brushed my shaggy bangs off my forehead. "You have such gorgeous eyes," she said softly. "It's a shame people don't see them more often."

I blinked and looked away, staring at cinderblock and hearing Echo & the Bunnymen on my crappy jam box. It was her mix tape. My classic rock, my comforter, my everything else was packed away for the summer.

"You're seeing them right now," I replied, returning to her steady gaze. "That's pretty awesome."

Smiling, she reached for my hand, holding it atop her warm thigh. Our bodies connected from knee to shoulder, full lips just inches apart. "Can I kiss you?" I asked.

"I don't know, can you?" she sassed, giggling at the grammar reprimand and craning her neck to offer me her mouth.

I could, I did and it was all-time. The first one soft, her perfect lips parting slightly. Lips Like Sugar. The second one harder, the tips of our tongues touching. By the third we had arms tight around each other and she was pulling me down to the thin mattress.

We made out for hours on the narrow dorm single. Thighs scissored, friction from our jeans heating us further. She felt like home in my arms. I thought I knew about love. I had never known this.

Physically, I went no further that night than fondling her beautiful breasts and exploring the thick nipples with my tongue. Emotionally, though, I went all the way. We fell asleep in each other's arms beneath a single sheet. I awoke around 5 a.m., shivering. Alone. Figures. Well, it was fun while it lasted. Then the door opened and there she stood, sweatshirt in one hand and blanket in the other.

I rubbed my eyes. She was still there. "I thought you'd left," I said.

"Why would I wanna do that?" she replied with a grin, shucking her jeans. She watched me watch her doff the white tee, posing in nothing but panties. Strong calves, womanly hips, full C-cups sittin' way up high, upturned areola. A vision. She pulled on the sweatshirt and snuggled against me, throwing the blanket over us.

"I can't believe you came back," I mumbled, slipping back toward sleep.

She kissed my cheek. "Of course I did."

That was a torrid summer. I scored a paid internship and stayed in the city instead of returning to my childhood home, states away. I rented a room from an older shut-in, Vanessa would visit and fucking soon followed. The teen never held back and was never hung up.

We learned something about each other the very first time. I had her naked; we were on a sheet on the floor because I didn't want my older housemates hearing the rickety bed bang against a thin wall. I moved my mouth south from her breasts. She gently put her hands on my shoulders. "I don't want you to stop, but it's that time of the month," she said, almost apologetically. (Why do women feel compelled to apologize for that? Oh right, probably because us dudes can be dicks about it.)

"How heavy are you?" I asked.

"Pretty heavy," she answered, giggling nervously.

I just shrugged and continued. She tasted great, especially while coming, ab muscles contracting in what I would learn was a tell-tell sign of an impending explosion. "Put it in me," she moaned when her shaking stopped. I knelt, thick cock at attention. Looking at her full black bush, I asked if I should use a condom. What a loaded question, pardon the pun.

"Only if you want to," she responded, spreading her legs further. Touché. I sank atop her, guiding my prick to her pussy. She was tight; it wasn't an easy fit. Eyes closed and arching her back, Vanessa's plump limps parted. "Ooohhhh yeaaahhhh," she exhaled.

I drove deep into her warmth. Burying my mouth in her neck, I felt those walls snug around my girth. She pulled her legs up, inviting me further into her center. "Oh my god," she whispered into my ear. "Oh my god. This is exactly what I needed."

I'd had pretty great sex before. In fact, I'd had pretty great sex -- including my first anal -- in that very room (read more about Lisa elsewhere). But this was different.

I've no idea how long it lasted. It seemed like an instant, but I was never quick in those days. I felt her thighs on my hips. Tongue on my lips. Pussy gripping my cock. I didn't want it to end, but her groans got to me. I felt the finish fast approaching while she urged me on, cooing as I coated her insides with come.

She held my arms around her as I fought for breath, face caught in her curls. Best ever. She gently nibbled on my ear. "That was amazing," she said quietly.

"I love you," I replied instinctively, immediately regretting it. I stiffened. Everything but my cock, that is.

"Well, Andy," she answered, pulling me even tighter. "I love you." Relieved, I relaxed. Everything but my cock, that is. I've been blessed with powers of quick recuperation, especially when properly motivated. "Oooh," she murmured, feeling me harden. "Again? Already? Yeah, again. Again!"

"Turn over," I ordered, regaining some composure. I pulled out as she giggled and began to follow instructions. That's when I noticed a red spot the size of Rhode Island seeping across the sheet. "Um..." I started.

"What?!" she asked, concerned, recognizing my hesitant tone. She twisted around, peered down and her eyes widened like the first day we cut class. "Oh my god, I'm so sorry!"

"Why?" I said, giving her tight young ass a light slap. When I looked again, all I saw was my copious come leaking from her cunt. "Didn't I tell you to turn over?"

She laughed again and quickly complied. The second time was even better.

But not as great as the first time I had her ass.

Of course, we were fire well before I shoved my cock up her smallest space. Fueled by the intense passion of youth, nearly every motion of hers made me hard.

Vanessa's resting pose was a thumb along sharp jaw line, index finger pulling at the bottom of her parted, pouty lips. When in thought, she'd softly stroke the digit's tip back and forth over the lip's curves. Mmm, sexy. Especially because it wasn't calculated. No, sensuality permeated every pore. She could play the slut, wearing slinky skirts sans underwear at restaurants and pulling my hand under the hem to feel her slick heat. Hardly innocent. But then she'd recline at her dorm desk with sun streaming in and illuminating her brown eyes, absentmindedly twirling curls with fingers from a hand half concealed in a bulky sweatshirt, and I'd melt.

She encouraged me to reveal my deepest desires, then enthusiastically embraced them. She would don one of my button-up shirts and nothing else (and we all know women are hot as hell naked save for a button-up) before pirouetting around the room, nipples poking through the cotton, cloth swirling around her dancer's thighs with that fine ass and pussy peeking through.

Once she did this and something caused my concrete cock to jump: Instead of glimpsing a dark patch between her legs, I only saw white -- she had shaved herself bare, another fantasy. Remember, this was before bald was de rigueur. And she kept it that way, igniting a fetish that burns to this day.

She eagerly engaged in phone sex when we were apart, placing the receiver near her pussy while frantically frigging herself so I could hear just how soaked that slot was. Then she'd loudly suck each finger clean. She read raunchy mags like Hustler Letters aloud to me (yes, pre-Internet proliferation; I'm old. Sigh) and we fucked to classic porn -- I distinctly remember doing her doggy style while watching "Devil in Miss Jones III."

We fucked constantly. Everywhere. And it was rarely sweet, gentle lovemaking, either; it was raw, furious and completely uninhibited. Her professor uncle's college office. A chair in our dorm's public lounge. A bathroom stall on her all-girl floor. The ancient foldout couch at her parents' cabin. Often quiet for fear of an embarrassing interruption, but always ferocious and filled with dirty declarations.

Some of our sex even came while her roommate, Tess, slept (or so I thought) on the other side of the cramped dorm room. Vanessa confessed years later that Tess frequently heard our fucking.

A talented artist, Vanessa had a style sense I couldn't fathom and a worldliness that could intimidate, even at that age. She introduced my small-town mind to her favorite make-out music: angst-ridden romantics like Bryan Ferry and the Smiths. Cool kids were fucking to slackers like Liz Phair and Pavement -- ironic detachment just a way to hide, well, angst-ridden romanticism -- but Vanessa preferred older Brits. (For Goths and such, it was the Cure. It's always the Cure.)

That artistry extended to the cello, which she played with abandon. Naked. Thighs wrapped around wood, fingerboard nestled between full tits. All her curves were killers. Even her tummy was like Madonna's "Lucky Star" era potbelly, to paraphrase a "Pulp Fiction" character.

So yeah, I was always ready to go. And she never said no. The first time I took her ass was by accident. Swear. We were in her uncle's on-campus office, Vanessa's hands braced against the wall while I pounded her pussy. Her ass out and legs wide, I repeatedly plunged into her from behind. One of my wild strokes missed her clenching front hole and the helmet partially pierced her tiny back bud, eliciting a yelp.

"Oh my god I'm sorry!" I quickly said, jumping away as Vanessa jerked onto her tiptoes, protecting her chute from my invasion. Splayed against the wall, defined calves straining as she remained on the balls of her feet, she slowly rubbed her groin against the rough cinderblock.

I gathered myself and watched her slide a hand down her side before it disappeared into that shaved snatch. "Ooh, don't be sorry," she said. "Is that what you want?"

Jeezus. She was so sexy and much more adventurous than myself. "I love you, Vanessa," I breathed, almost gasping. "May I fuck your ass?"

She grinned over her shoulder and dropped to all fours on the cheap carpet. "Yes, you may," she said, briefly dipping a finger in her slippery snatch before moving it to her ass and circling the star. "Do it!"

Now, neither of us were anal virgins. I had lost mine just a few months prior (recounted in my aforementioned "Lisa" story). Yes, I already was madly in love with Vanessa when Lisa invited me to claim her backdoor cherry, but fidelity is difficult when a hugely-busted, narrow-waisted eighteen-year-old offers her unsullied sphincter. I'm just a man.

But I wasn't fantasizing about Lisa's clenching hole at that instant. Not with Vanessa -- her dancer's back arched -- now digging that finger far into her ass. I slathered some hand lotion onto my cock, then slithered a slick digit up her tunnel. Massaged by the rough walls, our fingers rubbed together, widening the space in preparation for my thick pole.

Moaning, she slid the finger out and moved it to her clit. "Come on," she whispered harshly. "I want it!"

I spread her cheeks, lodged the head of my log in her entrance and pushed. She groaned as the first couple of inches entered. I pulled out, then shoved. She cried out when the big barrel of my stalk violated her most private place, but I didn't stop. I buried the entirety up in her and she whimpered loudly...and simply strummed her clit faster.

Quickly picking up the pace, I gripped her pale cheeks so firmly that I raised red marks on the tender flesh as I slammed into her. It was a sight, and so tight. She moaned continuously, the pitch rising whenever I reached her far reaches, crying at the rough ride.

"You're fucking my ass!" she exclaimed, hot at the notion. "Oh my god, you're fucking my ass."

"You love it, don't you," I hissed, my slim hips reaching a blur as I pushed all the way up her.

"I do. I do!" she squealed, howling at another series of thrusts. "You're gonna make me come!"

She grunted and froze, nothing moving but fingers on her clit like the bow on her cello's strings. I paused, fully sheathed in her asshole, while she clenched my cock and came with a long moan. She collapsed and I pressed down atop her, pushing her into the rug. Every spear from my sword drew a cry. She was tiring after getting hers -- and from the harsh treatment -- but didn't stop me. She never would.

Pummeling her sore hole, I didn't last much longer. Buried to the balls, I exploded inside her, both of us groaning.

When I finally pulled my prick from her ass, a river of come flowed from the stretched, reddened eye. I examined her swollen anus, seed streaming out and staining the carpet. Seriously, proof of our nasty fuck remained on the rug for the entire school year.

She moaned softly, motionless, goosebumps on her arms. I moved the hair from her face and she smiled, cheeks glowing. "Did you like that?" she asked with a knowing giggle, then answered her own question. "Incredible."

I helped her stand, then grabbed some tissues to clean the come glistening on her. "My legs are shaking," she said. "I'm jelly."

Anal became standard after that night. I'd take her butt whenever I wanted, often sneaking into her unlocked dorm room late at night, slipping off my clothes right next to Tess' bed and sliding under the sheets with Vanessa. She never wore anything under the extra-large t-shirt, ass exposed and vulnerable.

Sometimes I'd wake her by pushing my prick into her pussy, the hole immediately getting wet. Sometimes she'd stir with my finger already rooting around in her ass, prepping it for my perverted needs. Soon my rod would be forcing its way up her now pliant space, the hole yielding with less resistance after all the abuse. We'd both come, her roommate feigning sleep, then do it again in the morning after Tess left for class.

But we weren't always good for each other. Maybe some couples can separate sexual fury from the rest of their relationship. We couldn't. That same fire spread to our every interaction, and it wasn't healthy. We were the classic "fighting one moment, incredible make-up sex the next" sort of lovers, I guess.

We could be vicious to each other. We'd hurt one another, have wild sex and do it all again. Which horrid words would we sling to slay the other? [Redacted.] Sorry, I just deleted several specific examples. It's too painful, even for this unfeeling bastard. And I must keep something private, for god's sake.

So we didn't make it. Of course, it didn't help that I couldn't stay faithful. To my great surprise, young women seemed to find me fetching. Despite bedding a few through high school, I largely was dismissed as a nerd. But college was different. Smart, cute, geeky girls abounded, and some were willing to slum with me -- sly lines, winsome smile and puppy dog eyes appealing to good girls wanting to live it up a little.

I didn't miss many opportunities to cheat, treating each potential encounter like it could be my last. A couple of times, an exasperated Vanessa responded in kind, reminding me that she -- one of the hottest women on campus -- could catch a dick at will. I'd apologize for my indiscretion, beg for forgiveness, shamelessly slut-shame her for retaliating (I was such a hypocritical ass), rinse and repeat.