Brian Meets His Busty Match Ch. 01

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As he had each Saturday for the last few months, Brian walked into the doctor’s office, following behind his mother. He had known to wear just a T-shirt, shorts and flip-flops, as instructed. His mother, however, was wearing a skin-tight yoga outfit, the pants hugging every luscious curve of her large buttocks and thick, muscular thighs. More notably, from behind, he could see her enormous, wobbling breasts — they poked out from either side of her slim torso. Her lustrous dark brown hair was bunched into a ponytail that swung as she walked in front of him toward the receptionist.

She turned around, her massive rack swaying right in front of his face, and put one hand gently on his cheek. “Come along, Brian,” she said. “I know you still think these sessions are awkward, but the doctor says it’s important we continue them to keep you healthy.” She towered over her son — 5’10” to his 5’6″ — and tended to speak to him like a child despite the fact that he had turned 18 six months before. He looked up at her stunningly beautiful face and managed to eke out a smile. “Yes, Mommy, I know.” He had accidentally referred to her as Mommy one day recently when she had woken him up for one of his sessions, and it turned him on so much — and, he got a vague sense, her as well — that it stuck.

The truth was that Brian was always horny. There were two reasons why, at least according to the doctor, a specialist in what she called hypersexuality that his mother had found through a friend dealing with a similar problem with her son. He masturbated almost constantly, sometimes up to seven or eight times a day, his large penis never really softening. Erotic thoughts constantly raced through his head, spurred on by girls and teachers at school he had a crush on, and more recently, voluptuous lifeguards at the pool in their tight red one-piece bathing suits. (He had stopped going because it had become impossible to hide his nonstop erection.)

But the other cause of his problem was obvious: his stunningly beautiful, shockingly voluptuous mother.

Brian had never had a girlfriend. He wanted to, desperately, and he was a decent-looking young man with a sizable penis — but his condition made him extremely self-conscious. Once he turned 18, his mother, sensing that awkwardness, had sat him down. As he stared directly at her massive tits, which bulged out of her too-tight sweater with a plunging neckline — as usual, he simply couldn’t help himself — she asked him if something was wrong. After trying and failing to change the subject, he told her everything. She was clearly taken aback, but found the doctor through her friend — it turned out his problem wasn’t as rare as she initially assumed — and made him an appointment.

At their first visit, to his utter embarrassment, the doctor asked him just a few questions, then had him take his clothes off and masturbate, right in front of his mother. “Go ahead, Brian, cum for me. You can ogle your mother’s body if that helps,” the doctor had said, as the mother gasped, causing her giant rack to shimmy under her tight shirt, the buttons straining to contain her breasts. The doctor poured a bit of lotion on his cock. He wrapped both hands around his rock-hard prick — his preferred method, since it was so thick that one hand couldn’t make it all the way around. It didn’t take long before he orgasmed. “I’m sorry, Mommy!” he cried, as he sprayed thick rope after rope all over the room — including on his mother’s face and body.

After a closer examination — including having his voluptuous mother massage his penis until is was hard again and then jerk him off, spraying more cum all over her office — Dr. Romano diagnosed the teen with hypersexuality, a condition clearly exacerbated by proximity to such a gloriously statuesque, top-heavy mother. She prescribed three sessions a day: His mother was to help him masturbate, both by teasing him with her tall, super-top-heavy body and stroking his thick teenage cock.

They had their “practices” everywhere: In bed, when he first woke up. When he got home, she would greet him at the door wearing nothing but panties, a too-small bra, and heels. At bedtime, she would caress his penis with her huge bra-clad tits, bringing him to the edge, then simply rub her face all over it until he came, spraying on her face, neck and cleavage. (She never seemed to mind. “I just want to help my sweet boy,” she would say as she cleaned her off with a towel.)

A few months later, they were back at the doctor’s office for a check-up. His mother smiled at him, then turned to the receptionist, Becky, a young woman with delicate features and a full bust under her tight sweater. (It seemed that everywhere Brian went, he encountered busty women.)

“Hello, Ms. Pepper. Hi, Brian,” she said, smiling. “Brian, you can disrobe and sit over in the waiting area.”

He knew the drill — though he was always a bit embarrassed to be nude in front of both his mother and Becky. But he did as he was told, pulling off his T-shirt and shorts — he knew enough not to bother wearing underwear. His thick, rigid cock sprang out of his shorts.

“It’s OK, Brian, we know you almost always have an erection. That’s why you’re here,” Becky said with a sweet, almost maternal smile. Brian blushed.

“Come, Brian,” his mother said, her insanely curvy body wobbling as she walked over to the waiting area. Brian’s cock swayed back and forth as he followed her. They sat down on two plush chairs in the back of the waiting room. Brian noticed that the room was just slightly warmer than normal, presumably for naked patients like him.

“I know this is always a bit odd, Brian, but the doctor knows what she’s doing,” the mother said. “We’re doing this because I love you and I want you to be comfortable and happy. I’m sure you’d do the same for your Mommy.” She gently stroked his face. “You can have a condition. Mommy and the doctor both want to help… alleviate some of your discomfort.” She paused and looked down at his cock, then reached up and plumped her breasts, clad in a tight, baby-blue yoga top, presenting them to him; she knew that turned him on almost more than anything. He gulped.

“Would you like me to jerk you off now? The doctor said to help you whenever you needed it. It seems like you do. Are you super horny right now? Do you want me to play with your penis?”

“Yes please, Mommy,” he said bashfully.

There was a bottle of lotion on the side table to her right, and she pumped a bit into her left hand, then, casually, if it were the most normal thing in the world, began to jerk off her own son. “You can look at Mommy’s big breasts if you’d like,” she said.

He did just that, and moaned with lust.

Just then, he heard a noise from the front of the room. Two women entered: One, a stunning middle-aged woman, about his mother’s height and almost as busty. Whereas his mother wore a yoga outfit, this woman was wearing a business suit, though one that clung tightly to her curves. Her red hair was up in a bun.

Behind her, staring down at the floor, was a teen girl that Brian guessed was about his age. She wore a baggy T-shirt and shorts and looked like she wanted to be anywhere else but the doctor’s office. The girl was extremely petite, her mother probably almost a foot taller than her. She definitely looked familiar.

“Hello Ms. Stockton. Hi Rachel,” Becky said, clearly taken aback. “Goodness, it appears that we’ve double-booked this afternoon. Hm. Well, Rachel, why don’t you undress and take a seat while I check with the doctor.”

Rachel’s gaze darted up and she saw Brian, his mother slowly caressing his visibly throbbing cock. Brian didn’t know what to do, so he simply averted his gaze, but could still see Rachel out of the corner of his eye. He suddenly realized that he knew her from school — they had both graduated just a few months before.

Brian flashed-back to the end of their senior year. He had had a crush on Rachel for years, without even knowing her name. She was extremely pretty, with a delicate, sweet face; bright blue eyes, light brown hair that she generally wore in a ponytail, but occasionally wore down, the wavy strands cascading past her shoulders. She was shy, but would every now and then flash him a smile in the hallway as they passed. In math class, he couldn’t help but stare at her; she had caught him looking a few times, blushed and looked away.

But he had to admit that it was her body that he was obsessed with. She almost always wore oversized clothing, but also played on the soccer team, which meant that every now and then he would see her in her short-shorts and tight top. Even with her breasts strapped down by what he presumed was an industrial-strength sports bra, her figure was truly shocking: she was extremely petite; he doubted she was taller than 5 feet, and had a slim torso, arms and neck. After years of soccer, her legs were a bit thick and muscular and her ass cheeks had an impressive roundness to them. And, most notably, she had absolutely massive breasts, which appeared even larger in contrast to her diminutive frame.

Brian had stayed late one school day to help tutor a freshman. As he was leaving, the soccer team had just finished practice and was filing past him on their way to the locker room. He caught sight of her and couldn’t help but stare at her tits; even under the sports bra and a school jersey — the name of the team (the Cougars) distended so much that the word was barely legible — they were obviously huge. He looked up at her face as she passed, and she was looking him in the eyes. Embarrassed, he was about to look away, but she smiled and mouthed the word, “hi.” He smiled back. The rest of the year, he had tried to catch her in her soccer outfit, but she only wore oversized flannel shirts that covered everything — though, even so, her top-heaviness was evident.