Kylie’s Cups Ch. 01: First Gaze

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Ball Gag

Based on true experiences. Names have been modified to protect privacy.


I had always been told I was attractive. Even though as a younger teenager, I had been slightly overweight and awkward, I had always been told I had a pretty face. At the time this story takes place, I was a college student in Boston, beginning my junior year. Through running and a healthy diet, I had overcome the adolescent woes surrounding my figure. I was about 20, and in my prime. With tanned skin, an ethnically ambiguous face, long naturally wavy dark hair, and petite toned yet curvy 5’4 frame, I was particularly attractive to a certain subset of over older men who had an appetite for young exotic-looking women who fulfilled their dominant tendencies and desire for conquest. I was dating an older guy, James, a sophisticated professional in his thirties, suave, my first lover, and an incorrigible flirt. Though I was conscious of my appeal, I still hadn’t yet completely gotten over my insecurities about my body, and so I let it slide if I caught him looking too long at another girl or joking about threesomes, because I imagined that my body alone could never really satisfy a man.

Around this time, I moved in with a friend, Kylie. She was my age, a quiet, studious girl I had met in one of my English classes. Though most of the time, her body wasn’t clearly discernible in outdated jeans and baggy t-shirts, Kylie had a fantastic figure, something I had always had an eye for. Like I said, I wasn’t particularly secure in my own body and had become a master of comparison. I knew instantly how to evaluate my own attractiveness in comparison to my friends and particular how I measured up, literally, to their figures. Kylie had one of the best figures of my group of friends, particularly that Fall when we returned to school – she’d lost a bit of weight, and now living together, I saw her in shorts and tank tops, so it was obvious what it was shaped like.

She was about my height, 5’4, slim and toned from active swimming, with curly red hair down to her chin, and blue eyes in a cute face. She wasn’t particularly pretty, but her body more than made up for it. I remember seeing her on my first day back when we were moving into the apartment, dressed in short khaki shorts and a grey tank top. You see, Kylie was extremely busty. I wasn’t small myself, a 34D cup, which I had thought was more than enough, but I couldn’t get over the sheer volume Urfa Escort of her breasts. They were the kind that were way bigger than anything I had even imagined, the type of boobs you saw on porn stars. There was no doubt, however, that they were natural; she was young, so they were still firm, but the teardrop shape and soft under curve as they hung slightly suggested that they were completely natural. They stretched out her tank top almost indecently, and bounced heavily in her bra when she made the slightest movement. I remember noticing how heavy they looked atop her flat stomach and thin waist, and how unexpected on a girl with rather slim thighs. She’d lost weight, so they looked obscene stretching out slightly beyond her slender upper arms, jutting out below her narrow innocent face. It was obviously she was a few cups bigger than a DD, though I wouldn’t learn until later that semester than she was a 32H cup.

I should mention here that I have always been fascinated by other busty girls. I first realized that breasts can get really big, even on otherwise thin bodies, around the time I was 15 and my older cousin was changing in front of me for a party. I remember being absolutely transfixed by the weight of her huge boobs on her tiny body. It seemed surreal, yet intensely arousing. This is also a good time to mention that although I consider myself straight and have only wanted relationships with men, from this time onwards, women’s breasts and pornography highlighting voluminous busts have been the quickest and most satisfying way to arouse me. It may be a fetish of sorts, but I find very topheavy women incredibly hot and I have to control my gaze so that it’s not excessively obvious that I am staring at them.

But back to Kylie. I remember feeling both awed by her incredible tits and intensely jealous. While I had a very attractive body at the time, smooth, tanned, and toned from an active lifestyle, with nice proportional curves, I had always aspired to the “slim and stacked” model that was simply not attainable. I remembered thinking that I would insist on meeting James at his place or going out, and not inviting him back because I did not want him to see Kylie. It sounds incredibly petty, but I was young, James was my first lover, and I knew that he had a ravenous sexual appetite. I also sensed that Kylie, who was, incredibly, still a virgin, despite her shyness, craved attention and was quite Urfa Escort Bayan competitive with me.

We were both honors students, competed for grades, and developed a fashion rivalry that semester. I had always been into fashion, taking care of my appearance and wearing little dresses and skirts to class, and I noticed her envious gaze sometimes when I stepped out of my room. That semester, our very first living together, she shed the jeans and t-shirts for tight tops and miniskirts, low-cut dresses, and even halter tops for some parties. She usually denied being competitive with other women, but one night when we had been drinking together, she admitted to feeling jealous of some of her closest friends, including me, and wanting to outshine them in academics, looks, and relationships. I never forgot her confession, and for that reason, when she mentioned wanting to meet my boyfriend, I changed the topic or gave a vague answer.

I managed to keep James away from our apartment until October. One night, it was simply more convenient for him to come over to our apartment after work. Kylie had been casually dating someone and was supposed to be out, so I agreed to it. I met him at work and we went back to my place together. When we opened the door, I realized we weren’t alone. I could hear rustling in Kylie’s bedroom down the hall, and before I could do anything, she had emerged.

A strange tension engulfed us as she drew closer. It was my worst nightmare. James was coming face to face with her, and she was dressed in her most revealing outfit yet. She was wearing a very short tight black skirt over lace tights, with a tight leather jacket half zipped. She was showing an enormous amount of milky cleavage and one could make out the silk of her top under the jacket. She was wearing more make-up than usual, heavy eyeliner emphasizing the brightness of her eyes and otherwise soft blush tones highlighting her clear youthful skin. The combination of nubile femininity and her potent sexuality was intoxicating. I could feel James’ gaze on her, and caught the way she returned it. I felt like an outsider, intruding on an intimate moment. I remember how sharp the sting of resentment felt and how I chastized her, in my mind, for her slutty top, though it was no more provocative than clothes I regularly wore. I hated her for flaunting her massive chest and stealing the attention of the only guy I wanted to Escort Urfa myself.

“Hi, I’m Kylie!” she interrupted, breaking the loaded silence.

“James, this is Kylie, my roommate,” I said, reluctantly, hating the way he eagerly shook her hand and tried – discretely – to get another look at her pushed-up breasts.

“It’s so great to meet you,” she said smiling at him, “But I have to go,” she turned to me, “I’m meeting Eric.”

Eric was the guy she’d been seeing. I was glad to see her rush out, not wanting to prolong the encounter between my boyfriend and my tarted-up friend, but unfortunately, the damage was done.

No sooner had she left, did James make a comment.

“Wow, she’s really…” he made an obscene gesture with his hands, indicating the chest area.

I just raised my eyebrows, not wanting to encourage this.

“Are those even real?” he asked, as we went into my room, clearly still fixated on Kylie.

“Yes, they’re real. She’s got big boobs, no big deal.” I tried telling myself that being dismissive would make Kylie’s figure less threatening.

“Big? Those are massive melons. Who’s Eric? Her boyfriend? With a pair like that, she must have lots of guys trying to get a look…”

“Are you really asking me these questions about my roommate?” I said, starting to get irritated, “You want to get a look at them yourself?”

Realizing he’d upset me, James denied wanting to see them himself, saying that he just couldn’t help notice such a “freakish” size. I wasn’t entirely convinced, but I was very attached to him, and willing to convince myself that it really was just a scientific curiosity about an anomaly of the human form, not the unbridled animal lust that I had sensed when they first met.

This initial encounter paved the way for the tale of decadence and uncontrollable desire that will follow. Once James saw Kylie, no matter how much he liked me or how deeply I wanted a fairytale romance, it was like an unstoppable force. My young age, insecurity, and her loneliness created the perfect conditions for the transgressions that followed. James no longer wanted to meet at his place – he always asked if we could go over to my apartment, and it became increasingly difficult to make up excuses to say no. Kylie, meanwhile, seemed to be fully embracing her femininity and her clothes seemed more revealing than ever, making her even more threatening to me.

The next chapter picks up at my apartment, where I return one day, surprised by James who has come to visit me at lunch, let in by Kylie who happened to be at home, dressed in one of her skimpy peach camisoles and boxers, and the two are chatting animatedly, even flirtatiously…

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