tagFirst TimeA Collection of First Times

A Collection of First Times

byTotalKnockout©

Author's Note: all of these stories are autobiographical and absolutely true accounts of some very hot "first times" I've had. Only the names have been changed.

*****

***Oliver: my first oral experience***

My very first experience with oral sex was when I was 18 years old and still a virgin. I was at one of my very first college parties, and I ran into Oliver, a guy I knew from church. We weren't close, but he and I had been friendly. That night he was a little drunk.

"It's my birthday," he confessed drunkenly, as he pulled me into him on the dance floor. "I'm twenty-one..." It seemed like his buddies had gotten him drunk for the occasion. Normally Oliver was super shy, but I guess his inebriated state made him a little more bold. He danced against me and I let him. I heard some of the guys he came with whoop and cheer for him.

"Happy birthday," I whispered and wiggled my ass against him. He gently placed his hands on my hips, and I grinded back into him a little more. I wasn't sure but I thought I could feel the outline of his cock nestled between my round ass cheeks.

I had spent that last eleven years at an all-girls Catholic school, with no boys around, so I was pretty inexperienced for an eighteen-year-old. The furthest I had gone at that point was let some guy I had met at the rare school dance unhook my bra and play with my D-cups, pinching my stiffening nipples under my sweater while he jammed his tongue down my throat. Now that I was at college and away from all the strict prying nuns, I was up for some sexual experimentation.

After we had spent 15 minutes grinding on the dance floor, Oliver pulled me to him and whispered, "Hey, do you wanna get out of here?" I nodded and he grabbed my hand and pulled me into the hallway, his guy friends slapping each other five as we went out.

As soon as we made it into the hallway, it got quieter and all we could hear was the throbbing bass.

"God, you're so pretty," he murmured drunkenly and leaned into me, brushing a stray curl out of my face. He leaned in and kissed me, pressing me against the cinder block wall of the dorm. I could taste the beer on his tongue, which turned me on.

"You wanna go someplace more private?" I asked, looking up at him. He nodded.

The best we could do in that moment was the empty commons room next door. He pulled me inside and then locked both doors from the inside so no one could disturb us. Even with the doors locked, we still only had semi-privacy. The windows of the room looked out of the quad: anyone walking by or going into the party could see us if they were looking hard enough. We were so horny we didn't care.

We fell onto the couch, making out furiously, sucking on each others' tongues, our hands fumbling under each others' clothes. I wondered just how many horny couples had fucked on this very couch.

Oliver had pushed my padded bra and shirt up without even unhooking it and was sucking on my swollen nipples. I moaned and enjoyed him lapping and sucking on my ample tits. After a moment he paused, and pulled me up to sitting, while he sat in front of me on the floor.

"I want to taste you..." he said. He tugged my pants down over my hips, pulling my lacey thong underwear down with them. I gasped as my naked pussy was exposed to a boy for the very first time. Once my pants were around my ankles, he sat on the floor between my open legs and gently parted my pussy lips with his thumbs. Anyone who walked by could see my spread pussy, and Oliver with his head between my thighs, ready to go to town on my wet snatch.

He sought out my hard clit with his tongue, licking and sucking on it, while he splayed my chubby pussy lips with his fingers. Even without his warm spit, I could already tell my pussy was sopping wet.

"Mmmmm you taste so good..." he groaned, pausing and then sucking my throbbing clit some more.

"Ohhhh fuck..." I moaned and shuddered, the wet noises of him lapping at my weeping snatch echoing in the empty commons room. I grabbed the back of his head and pulled him into my pussy, feeling myself getting closer and closer to cumming all over his face. I couldn't believe this shy boy from mass, who was an altar boy, was now eating me out in a public commons room.

As I discovered that night, I had a bit of an exhibitionist streak in me, and the thought that some drunk frat boys could be watching me getting my pussy eaten for the first time pushed me over the edge. I came, bucking and squirming against his sucking lips, my thighs tight around his ears.

When I finally came down from my orgasm, Oliver climbed back up on top of me, smiling. My pussy juices were still wet on his face. He wiped his face on the couch cushions and then I pushed him back, climbing down between his legs to return the favor.

I had seen pictures of cocks before, and felt them between a layer of clothes, but I had never seen a naked one live in the flesh, and I had certainly had never sucked one before: tonight was going to be a night of firsts.

When he saw what I intended to do, Oliver eagerly unzipped his pants and pulled them down for me, his naked cock springing up, hard and long. I later learned that my first cock was quite the specimen. About seven inches long, fully erect and slightly curved, cut, with tight round balls, Oliver's cock was and still is, one of the most beautiful cocks I've ever seen. Even as a virgin, it made my mouth water. I looked up at his face, already braced with anticipation, and licked my lips. I couldn't wait to put this gorgeous cock in my mouth.

The second his smooth mushroom tip parted my wet lips I knew I was going to love sucking cock. I hungrily suckled on the swollen head and he moaned, arching his back towards me. I held the thick shaft upright in my fist and then slid my mouth down as far as I could go without gagging. When I pulled my lips off of his cock with a little pop, it was glistening with my spit. One string of spit connected my swollen lips with the wet tip of his erection.

Still holding his cock upright, I licked the shaft from the bottom to the top in long strokes like I was licking a popsicle. Oliver moaned and grunted. For a cocksucking novice, I was a natural.

After a bit, I plunged his cock back into my mouth and started bobbing my head up and down hungrily on his cock. He moaned some more and tangled his fingers in my hair so he could control the pace. The sound of his grunting and groaning turned me on... I slipped a finger in between my wet pussy lips and rubbed my clit while I blew him.

After a few minutes, we were interrupted by some banging on the commons room door.

"Hey, Oliver, stop fucking freshmen girls and open up in there!" some of his friends shouted through the door, "We're leaving!" Oliver gasped and pulled out of my mouth.

"I'm so sorry," he apologized, stuffing his erect cock in his pants. "I have to go now or I'm going to get into trouble..." I started pulling my clothes back on and stood up. I think our fooling around had sobered him up a little and some of his awkwardness was back.

"I'll sneak out first so they won't bother you," he said, and smiled awkwardly at me. "See you some other time?"

"Sure," I replied. And he quickly exited, closing the door behind him. I heard his buddies cheering him on as they noisily left the party.

We never hooked up again but I often think about his awesome cock and the hot time we had on that couch.

***Harley: my first creampie***

Harley was a Southern boy from Missisippi, a ROTC Air Force guy with the rock hard body of a 22 year old soldier. I met him my senior year at college, when he decided that he wanted to try acting. We were cast in the play together, and I noticed that he was always watching me whenever I had to do my romantic scene with another guy. One time when we were back stage he told the poor 18-year-old tasked with kissing me on stage that he was doing it wrong.

"You need to be more confident, forceful, when you grab her to kiss her: like this..." he scolded the younger kid in his heavy southern drawl. He reached out for me by way of demonstration, and much to my amusement, pulled me in for a deep passionate kiss. I felt my knees go weak. "That's how you kiss a woman," he said to the pale-faced freshman and walked away.

"Harley is super into you," my friend Kim whispered to me, as we watched his tight, muscled ass saunter away in his costume, "you should totally hook up with him at the cast party tonight."

Later that night, Harley showed up to the cast party at my house with a six-pack of Miller High Life, and immediately started drinking with the other guys. I could feel him staring at me from across the room. I had worn a low-cut top for the occasion.

By the time he sauntered up to me, we had both had a little too much to drink. He clearly needed his liquid courage to approach me.

"Heyyyy, darlin'," he slurred slightly, "what's happenin'?"

"Nothing much," I replied slyly and took another swig of my beer. "Except you kissing me earlier..." He grinned and looked away.

"You like that?" he asked with a little bashful smile.

"Mmmmm hmmm," I nodded.

"Want me to do it again?" he drawled, his face drawing in closer to mine.

I grabbed him behind the neck and pulled him close to me and we kissed, his tongue swirling around in my mouth. He tasted like beer and smelled like pure male pheromones. I couldn't get enough.

Somehow when we came up for air, we were on the couch and the whole party had cleared out. I guess everyone felt like they should give us some space to do the inevitable.

"Wanna take this to my room?" I asked slyly. He nodded and he followed me to my bedroom, kissing and squeezing me from behind as we went.

As soon as he shut the door he pulled off his shirt and I got my first real view of his muscled chest and abs. It was a sight to behold.

"You like that, beautiful?" He asked drunkenly, and started pulling off his pants in a sexy striptease. I laughed and turned to put on some music so my roommate wouldn't hear us fucking in the room next door.

His cock was already semi-hard as he lay back in my bed in nothing but his white briefs. I found it kind of funny and hot that this guy still wore tighty whities. Most guys I knew only would be caught dead in boxers.

He watched me hungrily as I pulled off my shirt and skirt and dropped them to the floor. I climbed into bed with him wearing only my bra and panties. He immediately reached up to unhook the clasp on my push-up bra, and groaned at the sight of my round milky jugs with their fat upturned nipples as they swung free.

"Ho-leeee shiiit," he whistled his appreciation as he kneaded my soft flesh between his fingers, "these are some amazin' titties..."

I was a little drunk and we were moving fast. I climbed on top of him and started grinding my satin-clad pussy against his cotton-covered cock. He groaned and I felt his erection growing between my pussy lips. He pushed me off of his hips for a second to shimmy his underwear off and threw them on my floor. I got my first glimpse at his cock. It was average-sized, slightly curved and stood up rock hard away from his muscled body. I was wet and throbbing and anxious to fuck.

My ex-boyfriend was the only cock I had had in my pussy for the past two years. He had popped my cherry two years before and we had done it pretty regularly after that, but there was always so much pressure for sex to be slow and romantic. I never felt like I could just let loose with my ex. Harley was going to be the first casual fuck I was going to have and I was really looking forward to some no strings attached sex.

I peeled my thong panties off and climbed on top of his naked cock and began grinding my wet twat on his now naked erection. He moaned and pushed up against me, trying to squeeze his dick into my pussy.

I've always had a pretty tight pussy and even though I wasn't a virgin, he was having a hard time getting his cock inside me. I adjusted myself until I was holding my chubby pussy lips open and then teased his swollen cock head with the opening of my vagina. I was just about to lower myself on his stiff erection when I realized through my drunken haze that we had forgotten to get a condom.

"Oh shit, we forgot to put on a condom..." I groaned, pulling off of his cock. "It's okay, it's okay, babydoll... I'll pull out," he moaned. "Please just don't get up, you feel so good..."

I don't know if it was his cute Southern accent, or the way his bare flesh felt in between my pussy lips, or the fact that my ex and I had always used condoms, but I gave in. I squatted over his cock and slowly impaled my tight pussy on his erection until our pubic hair was mashed against each other.

I bounced up and down on his cock until we got into a nice fucking rhythm. He reach up and swirled his tongue in my mouth and palmed my tits while I rode him. From his grunts and groans I could tell he was going to pop soon so I reached down and started toying with my clit, but it was too late.

A few seconds later his eyes rolled back into his head and he grunted and came hard, spurting thick ropes of jizz inside me. He came so hard so quickly I could feel the first jet of cum bathing my insides with his goo. "Oh, fuck..." I moaned. When I looked back up at him he had passed out, his softening cock still buried in my cunt.

I slowly climbed off of him, his shiny cock sliding from my stretched hole, now filled to the brim with his spunk. I felt a little dribble out of me and put a hand between my thighs to catch his cum while I quickly tiptoed to the bathroom.

By the time I got into the bathroom, a small puddle of his pearly jism had dripped out of my pussy and into my cupped palm. I quickly sat down and let more of his spunk drip out of me and into the toilet. As I wiped off my hand, I reached for the small make-up mirror on the counter. Still sitting on the toilet seat, I opened my legs and studied my thoroughly used pussy. My lips and clit were swollen and wet and I could see his thick white cream oozing from my hole. I can't explain why, but looking at my creampied pussy turned me on so much, I rubbed my clit until I came all over my sticky fingers, pushing out more of his cum from my vaginal opening.

When I finished cumming, I grabbed some toilet paper and wiped away a long viscous strand of his cum that was dangling from my spent pussy. I turned off the lights, shuffled to my bed and passed out, Harley's sticky cock pressing into the cleft of my ass.

The next morning I got up at 6am for my shift at the campus coffee shop. Harley was passed out and snoring in my bed. I contemplated waking him up for a quickie, but thought better of it. I left him a note and then left for work. I swear I could still feel his spunk leaking out of me all day.

***Jean-Paul: my first monster cock***

I met John-Paul when I was modeling for a figure drawing class. He was smart, clean-cut and professional when he walked up to me after class and handed me a business card.

"This is a link to my work... Just so you know I'm legit," he said matter-of-factly as I was pulling my robe on and reaching for the card. "I'm always looking for models and I think you'd be perfect. Check it out and let me know if you're interested." Before I could answer, he turned on his heel and sauntered away.

I found the card in my pocket a few days later, and remembering his odd manner, I looked up his website and studied his portfolio. His website stated "John Paul Mercier: Erotic Nudes" and the whole site was filled with a hundred erotic nude photographs, all tastefully done, naked women of all shapes and sizes photographed in their homes and in natural environments. I was intrigued.

Before the next class I found him by his easel and told him I had checked out his website.

"Oh yes?" he said, raising an eyebrow at me. "What did you think?"

"Looks interesting," I replied equally cryptically. "Do you always photograph women in their homes?"

"Yes," he replied, "People are much more... relaxed in their own home."

"I see." Something about the way he said "relaxed" made me wonder just how relaxed he was talking about. Relaxed enough to reward the photographer for his hard work?

"I pay $50 to shoot you in your home, and you get a copy of your favorite print. What do you say? Interested?"

"Okay, sure." Alright, I'll bite, I thought. There was something about his no-nonsense, businesslike tone that turned me on. And I had a lot of experience posing nude, so it would be an easy fifty bucks at the least.

"Great," he replied, "Email me your info and some times that work and we'll set something up." And then class began.

Normally, when I'm posing for the figure drawing class, I hold a pose and then let my mind wander. Today, I could feel John-Paul's eyes on me, as it scanned and appraised my naked body. Something about how he was looking at me made me sweat. Little beads of moisture appeared behind my knees, on my upper lip. At one point I watched him study my freshly shaved pussy and I swear he knew I was getting wet. When class ended he locked eyes with me and smiled slightly.

Later that week we arranged for him to come do the photoshoot at my apartment that weekend, when my roommate was out of town. He walked up all four floors to my apartment with his camera and all his equipment, and I answered the door in just my robe.

"Wow, it's hot," he said, removing his jacket, "How about we get to work?"

I dropped my bathrobe and hung it over the chair, this time I was nude for an attentive audience of one. He was very professional and we took some artsy shots in the kitchen where the light was good. Me looking out the window, me leaning over the stove, my naked ass pointed at his lens. He clicked away silently for awhile.

After we had shot on the couch and at the table he suggested moving into the bedroom. At this point, I was getting a little hot and bothered and I could tell he was enjoying his work. I lay back on my bed.

"So... You spend a lot of time around naked women," I said, "Do you ever feel tempted to do more than take photographs?" He looked up from focusing his camera and smiled slyly.

"It depends," he said, "on what's being offered..."

I slowly opened my thighs, opening my shaved snatch to his hungry gaze. I watched him swallow hard, his eyes narrowing on my wet slit. I snaked a finger between the wet lips and started playing with myself while he watched, captivated. He smiled and started snapping some more pictures.

"Do you like what you see?" I asked, and giggled naughtily. I splayed my fingers open, exposing my throbbing clit to the lens. John-Paul took four or five more photos before placing his camera on the chair and turned back to me, watching me rub my clit. He took three or four quick steps to the bed and then climbed between my legs fully clothed, and lowered his face to my juicy pussy.

His long tongue wiggled between my lips and teased at my swollen clit, then he quickly ran his fingers between my slit to lubricate them and plunged his fingers inside me, fingering my pussy while he ate me. It took me about three minutes of his fingers and tongue on my wet cunt for me to cum hard all over his face, moaning in orgasm and covering his face in my juices.

"Fuuuuck that was hot," he moaned, coming up for air.

"I can return the favor..." I replied, now hungry to see this guy's cock.

"That all depends on if you think you can handle this..." he said, unzipping his fly. Without pulling down his pants, he pulled out the biggest cock I've ever seen. It was about ten inches long and very fat, with a big purple head, already leaking precum.

"Holy shit," I breathed, actually wondering if I could get that monster meat in my mouth. I began reaching for his cock and he stopped me.

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