The Real Kate Ch. 01

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Kate has her first good orgasm.
7.6k words
4.17
28.3k
15

Part 1 of the 3 part series

Updated 06/08/2023
Created 03/27/2018
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The story grew from kernels of truth lying fallow in my memory for many years. As they sprouted, a work of complete fiction evolved. Any similarities to real people are accidental and unintentional.

*****

Kate has her first good orgasm

My name is Kate, and I was 23 years old when these events unfolded 35 years ago. Without exaggeration, I can assure you that people considered me extremely attractive. Photos from the time depict a young woman, 5'8" tall, with a slender 115-pound frame, firm a/b-cup breasts, brunette hair, and a model-pretty face. Genetics were kind to me, as I never set foot in a gym, or did anything special to maintain my physique.

Not to brag, just to illustrate: My sister Lucy, three years my elder, modelled and acted in New York City. After years of work, she won a small recurring role on a soap opera. Proud of her success, she invited me to the set to watch. Lucy introduced me to the director, who looked me over and, without even a "hello," exclaimed "where were you when we were casting for Lucy's part?" Lucy shot me a daggered look, and never invited me to the set again.

Once, when I was 19 and walking up the street, a guy came toward me on a bicycle. His eyes locked on me, and his head swiveled as he rode by. Right into an intersection where he was hit by a car. They took him away in an ambulance.

Yes, an extremely attractive young woman.

At the age of 23, I was neither very sexual, nor very sexually experienced. In many ways, I suppose the word "prude" applied. Of course, I knew my effect on men, and, if I'm honest, I admit that I liked it. After all, they'd been looking at me for over ten years. I rarely wore a bra, often dressed in short skirts and tight shorts, and didn't mind when people stared. OK, I wanted men to look. But it was more about the attention and, I suppose, it felt like a kind of power; not a sexual thing for me at all.

In fact, sex just wasn't that important, and I wondered why everyone made such a fuss about it. It wasn't much on my mind. I had a difficult time reaching orgasm, even when masturbating. I didn't have masturbation fantasies and it was a relatively rare activity for me. I didn't mental energy on it.

Of course, I dated a little in high school. Looks and IQ represented my two most important criteria in a boyfriend. My mom always said, "looks turn heads, but brains pay bills."

I lost my virginity after my senior year to Nick, my then-boyfriend and, arguably, the best-looking guy in our class. We stayed together through our first two years of college, not far from home in the Midwest. I never orgasmed with him, and we weren't particularly sexually active.

We didn't talk about sex, or during sex. There was no oral activity, and we never moved out of the missionary position. I masturbated myself to orgasm occasionally, and that pretty much defined the extend of my sex life with Nick. It just wasn't a sexy relationship. Which was fine with me.

One day I found Nick in his dorm room with another girl in his bed. Objectively, she was nowhere near as attractive as I am. Nick and I broke up. It didn't hurt as much as one would think. In retrospect, I think I dated Nick because people expected me to have a good-looking boyfriend. I conformed to the social norm, but I didn't really care for him. I certainly didn't love him.

My next relationship was with Peter. He was an engineer, kind of a nerd, but very good looking in an all-american way. I had my first partner orgasm with him; I could come when he licked me, something he did about once a month. But never from intercourse. For me, our sex life was kind of blah. I didn't enjoy giving oral, and only did it when I absolutely had to. He was quiet when we made love. He would finish and then, sometimes, lick me until I came.

We did it about once a week, maybe a little less, which seemed fine to me. I guess I'd say we were well matched in the sex drive department. Continuing the trend from my relationship with Nick, we didn't talk about sex or our fantasies. But we did plan a life together.

After we graduated, he took a job in Boston, and I moved to the east coast with him. A handsome man, with no bad habits, and a promising career seemed like a good catch. My family had always struggled financially, and I liked the security that Peter offered. I thought we would get married. I found a position as an assistant manager in a chain retail store, a job that I hated, but it had upward potential and gave me a good discount on clothes.

Our sex life dropped off after the move. Peter worked long hours, and intimacy went from infrequent to practically non-existent. As we'd never been that active, I didn't think much of it. I didn't miss it, I suppose. Our combined incomes allowed me to buy nice clothes and quality makeup, decorate the apartment, and purchase a new car. I felt content.

About three months after the move, Peter broke up with me. He had started dating another engineer from work. Feeling stupid, I learned he had lied about those late nights at the office. He said that, while I was beautiful, I was "a cold fish" in bed. It hurt. I mean, I knew I was pretty, wasn't that enough? I'd never thought that much about my performance in bed. And certainly never conceived that someone would leave me because of it, particularly for a less attractive woman.

Since Peter had leased the place, I had to relocate. I felt unmoored, having moved to an unfamiliar area with no friends, for a relationship that no longer existed and a car payment I could barely afford. I began to party a bit, a way to fill the void and suppress my fear.

I found a shared housing situation for myself. I got the master with a private bath in a four-bedroom home. My roommates were Mary, Steve, and Jim. We were all about the same age.

Mary was the first person I ever really knew from the south. She had a deep accent, which sometimes I struggled to understand. Mary was average looking, with a flat-nosed, square face, dirty blonde hair, big soft breasts, and a stocky build. She would have been on the edge of OK looking if she lost 15 pounds, but she didn't really care to do it. Not a head turner.

High-school educated and of average intelligence, she worked in a medical office, at a low-stress job. Very sexual, Mary always had a crude comment or joke and talked freely about sex in general, and her sexual experiences in particular. To hear her, she had bedded quite a few men. We were friendly, but not really friends. Not my type.

Steve was tall and lanky and, unfortunately, had a badly acne-scarred face. He seemed relatively quiet and travelled a lot for work. A nice guy, he was self-conscious about his looks. He didn't take the same interest in me that most men did, which I thought was a little strange. But safe. I didn't pay much attention to him as he was unattractive and seemed of average intelligence. Sounds cold, but it's true.

Jim turned out to be an ass of the first order. I will acknowledge that, objectively, he was extremely sexy, with a totally ripped body, a classically handsome face, and an air of confidence. He was probably 6'1" and 200 pounds of solidly defined muscle. He worked at a gym, and as a print model, mostly for bathing suits, underwear, and t-shirts. Things that his body went well with.

Jim was always walking around the house without his shirt and wearing shorts that emphasized his obvious bulge. I wondered whether he stuffed something in there to make it appear huge, because none of my boyfriends looked anything like that. Mary loved it.

As I soon learned, Jim's bedroom was a revolving door of conquests. Busty girls from his gym, I guess. Most left in the middle of the night, but occasionally one stayed for a starry-eyed breakfast. Some wore wedding rings. They almost always came back for more, until Jim tired of them. He was busy with them at least four or five nights a week. I couldn't imagine wanting that much sex. I was glad my bedroom was at the other end of the house, so I didn't have to hear it.

Jim began flirting with me immediately after I moved in. It was largely unsophisticated comments, kind of like high school. I ignored him. While his body was undeniably hot, he had a room-temperature IQ, pursued women for sport, and clearly considered himself god's gift in the bedroom. Yuk.

Perhaps because I ignored him, he began overtly staring at me in a way that told me he was having sexual thoughts. In truth, I liked the fact that he wanted me and I knew that, unlike his parade of chesty bimbos, he would never have me. Sometimes I would tease my nipples hard before I went into a room with him, just to make him think about my breasts. It was that power thing again, I guess.

Our house was not far from an ivy-league university. After a couple of months, I began dating a senior from the school. Reasonably bright, Brad was also a hockey player. Tall, with an athlete's body and a good-enough face. He lived in a rental home with four other guys, and his bedroom was on the second floor. Right underneath his space was Mark's room. I walked past it every time I went up to see my hockey player.

Brad could get hard just looking at me, which I loved. I didn't even have to touch him. Unfortunately, he had a severe premature ejaculation problem. He rarely lasted more than 30 seconds, sometimes he had trouble making it to ten. Which, in a way, was OK...because his bed squeaked incredibly. It annoyed me to no end.

I didn't orgasm with Brad. He couldn't even get me to come from oral. It was really a rebound relationship that I knew was going nowhere. He was hot enough, intelligent enough to carry on a conversation, and he liked to party; and so did I.

One evening, on my way to Brad's room, I heard clearly sexual moans as I walked toward the stairs. Mark's door was ajar, exposing a slice of his room. That wedge included his bed. Mark had placed his mattress on the floor, and a slender, small-breasted blonde girl on her back, with her eyes closed and her legs spread, occupied it. Mark had his head between her legs, licking her. She was writhing and moaning and had her hands on the back of Mark's head. I could hear her talking to him - telling him how good it felt and how he was "the best cunt licker she had ever had."

I could see Mark's hard cock, so stiff it pointed straight up - parallel to his belly. I had never seen a dick that hard before. The tip was even with his belly button. In retrospect, I now know that all my previous boyfriends had been on the smaller side in that department. Mark was, perhaps a little longer than them, but not by much. He was my height, with a slim build, but obviously worked out as his body was extremely well-defined.

I was mesmerized, and I couldn't help myself from stopping and watching. This pre-dated internet porn, and I had never seen another couple in a state of intimacy.

Mark teased her and licked her, and they talked. Dirty, sexy talk like I'd never heard before.

"You're so wet and tight. I love the way your cunt grips my finger. I can feel you getting close."

Her undulating hips and guttural moans were incredibly stimulating. Mark would bring her close to coming, then stop and pull back. I watched her hips move up, trying to get his tongue back. He did this again. And again. Then asked her if she wanted to come.

"Yes," she hissed through clenched teeth.

"Keep your eyes closed and tell me your last masturbation fantasy." Mark rubbed lightly over her clearly swollen clit with his finger. I was getting very turned on.

As he stimulated her clit with his finger, she spoke. "Last night I masturbated and imagined that I stepped out of the shower and came into my bedroom and there was a guy from my gym waiting for me, naked. He had a huge cock, even limp it hung halfway down his thigh. It was bigger limp than you are erect."

Mark slowly slipped two fingers inside her wet and swollen pussy. I could hear her moan and watched as she moved her hips to take the digits deeper. His brought his lips down and began to lightly lick her bud. She writhed and gasped. Mark told her to keep talking. He sucked her clit into his mouth, eliciting a sexy groan in response. Mark lifted his hips and I could see his cock twitching. It looked so hard. Her hands grabbed his triceps and her fingers dug into his skin. They would leave marks, I was sure.

The girl continued: "I walked over to him and kissed him. He took my hand and put in on his tool and I lightly stroked it while he caressed me and kissed me. He cupped my breasts and made my nipples hard. Then he slid one hand down my belly. My legs parted for him and he began to tease my pussy lips, lightly running his fingertips over them."

"I could feel his cock getting harder, bigger. I got really wet. He turned me around and bent me over the bed. I pictured the massive head of his cock rubbing against my pussy. I was slick and slippery. He pushed the head against me. It was huge, but I wanted it. I wanted to feel that monster stretching me out. I spread my legs a bit more and lifted my ass up to make it easier for him to enter."

Her hips were moving faster now, and Mark was sucking her clit into his mouth as he moved two fingers insider her. I knew she was getting close.

"I imagined the feeling of the thick head pushing into me, opening me up, filling my pussy. I fingered myself while I pretended to experience being stretched by his huge manhood. 'Yes...please...fuck me' I begged. I masturbated imagining him taking me with that massive cock, fucking me hard, stretching me out, making me his, making me ask for it, plead for it."

And then she came. She grabbed Mark's head and bucked against him, quivering and moaning. Her orgasm must have lasted 30 seconds. I'd most certainly never had an orgasm like that. Mark looked up at her, slid himself up her body, and whispered something in her ear. I watched as she wrapped her arms around his lean body. She reached down and grasped his erection, and Mark sighed as his slim cock disappeared inside her very wet opening. It was gentle and loving, and very, very intimate.

As he entered her, her eyes slowly opened, and she saw me. She just looked at me and gave a little smile, or, perhaps, I would more aptly describe it as a smirk. Then she extended her foot and closed the door. I knew I should keep going up the stairs. But, I didn't. I stayed in the hallway beside the door, listening to them having sex.

Altogether, they made love for over an hour. Even though I couldn't make out what they were saying, I knew that they were doing something I had never done. The girl had multiple orgasms. While I haven't ever watched a clock, I'm sure I'd never had sex last for over 20 minutes from first kiss to post-coital shower.

It left me feeling unsettled. Horny...but also aware that I had not even imagined experiencing anything like that. I couldn't help feeling that my sex life was boring and, by extension, that I was boring in bed. A cold fish.

I'd also never thought much about cock size. Mark's girlfriend had put previously unknown thoughts in my head. Steve had a huge lump. Was he really that big? Were my boyfriends small? Was that why I didn't come from intercourse? Size obsessed Mary, that's for sure.

Uncharacteristically for me, I jumped on Brad as soon as I walked in his door. Squeak, squeak, squeak, and he was done. I found myself thinking about the size of his cock. A little smaller than Mark. Same as my other boyfriends. He got up to shower, and I masturbated myself to orgasm while he did, imagining that I was being made love to the way I had just witnessed, except I blessed Mark with a bigger cock.

About two weeks later in the morning, I went into the kitchen in Brad's house and to discover Mark there, making breakfast. He liked to cook as it turned out. "Where's your girlfriend?" I asked. A puzzled look crossed his face, and then a crooked smile.

"Oh Lisa," he responded. "We're not a couple, we just keep each other company sometimes. Long term, I'm not her type; she like big guys. She told me that she saw you watching us, you know. And, of course, we heard you two squeaking. The whole house can hear that bed."

At that, I turned bright red and didn't know what to say. And what did his comment about "big guys" mean? It couldn't be penis size, could it? I wondered. After the things I'd heard them say, I thought it was possible.

"Where's Brad?" Mark bridged the silence.

"He had an early hockey practice and left me on my own," I confessed, still red.

"Risky move with a beautiful woman in a house full of men," Mark responded and again gave that little smile. "Would you like some breakfast?"

Was he flirting with me? Sure seemed like it.

By the end of the meal, I was convinced be was probably the smartest person I had ever known. And I was mildly sexually aroused. That night, I masturbated imagining that I was Lisa, in Mark's bed. A week later, I broke up with Brad. A week after that, Mark asked me out. He wasn't really my type physically, as he was short and, although muscled, he had a slim build. I like taller, huskier guys. But, I'd been masturbating to him. And he was super-smart. I said yes.

Our first date consisted of a walk around the campus. There were numerous stops at places of interest, and lots of conversation. A computer science major, it was clear that Mark was significantly brighter than your average human. We ended up back at his room, sitting on the floor mattress, as there was only one hard-backed chair in the space.

He asked me if it was weird to be right under Brad's room. I said no, because I never really cared that much about Brad. "You know I could hear it every time you guys had sex," Mark commented. "It never seemed to last very long. Did you come?"

Taken aback by the forthrightness of the question, I colored again, and shaking my head to indicate "no." "Well Brad's the original minute man," Mark added. "I don't think the squeak has ever lasted more than 60 seconds with anyone."

"Wait - so he's had other girls here?" I knew he had moved in just before we started dating; I wasn't sure how that was possible.

"He wasn't exclusive with you. I assumed you knew."

The shocked look on my face told Mark everything. My head was swirling. Why did all my boyfriends seek other lovers? Was there something wrong with me? A cold fish in bed?

Mark chose this moment for our first kiss. Leaning in, "I think I know a way to make you feel better" he whispered. And our lips touched in a soft, sensuous connection. His tongue lightly teased my lips and I responded by opening my mouth just a bit. Feeling the opening, his tongue pushed forward, and we kissed deeply. It was hot, and I felt my body responding. Best first kiss ever. No, best kiss ever.

As we kissed, Mark's hand gently caressed my face, my hair, my neck. It slid down my shoulder and over the side of my braless breast. My nipples hardened, and he brushed across them with the back of his hand. I moaned with pleasure into his mouth.

With our lips still locked, he took my hand and led it to his crotch, where I could feel his hardness through the fabric of his jeans. His hand went back to my belly, and he began working it down, inside my pants.

At that, I wrapped my fingers around his wrist. "Please...stop. I'm not ready for this...and I don't go that far on the first date." I know I sounded tentative and unsure.

A gentleman, Mark stopped. "No problem - I'll never push your boundaries."

We spent the next hour kissing and talking, and then I drove myself home. Part of me was wishing that he wasn't so respectful of my limits. I was horny, not a feeling I usually experienced.

I walked in the door to find Mary sitting at the kitchen table, drinking bourbon by herself. She looked up at me with wet eyes and, in a slightly slurred deep southern drawl, asked "Kate, have yuh evah hayad a really big dick?"