Story and characters entirely fictional. Sometimes crazy risks don't work out, but sometimes they do.
*****
Mr. Downs sat in his office waiting for his 4pm appointment. He didn't normally take appointments so late as school finished at 3:05 and he was usually headed home by 4, but something had caused him to make an exception that Friday. Karen, the student in question, had been quite insistent and he had relented. She had seemed distraught about something but wouldn't say what it was.
As the school guidance counselor he saw most of the seniors several times over the course of the year but he didn't recall much about Karen other than she seemed to be a bright student (if a bit sheltered), usually dressed quite demurely for a girl her age but that she had shapely legs. She had seemed overly shy with few friends although she was pretty enough. Perhaps the fact that she had been home schooled for most of her life had something to do with it. She had only started attending public school her junior year.
He was 32 with short-cropped dark hair and trim frame, a little less that 6' tall. His small office had a desk, a couple of chairs, and a couch - a legacy from when the small room had been used as a faculty lounge during some repairs several years ago.
There was a knock at the door and he opened it to find a young woman standing there. She was about 5'4" tall (although the platform sandals she was wearing made her almost as tall as he was) with long brown hair, a pretty face, and did have shapely legs. She seemed anxious or nervous about something.
"Hi Karen, come in."
"Hi Mr. Downs." She smiled at him and he noticed a shine in her deep brown eyes, the pupils large with interest.
She was dressed in a cotton print dress with a button-up front. The bust was a bit small for her ample chest and as a result there were gaps between the buttons and he could see that she had on a white cotton bra. He found himself staring at her chest with involuntary interest which she immediately noted and pouted.
"What's up Karen? Why the sad face he asked?" bringing his gaze back to her face with some (hopefully) concealed embarrassment and a slight flush to his cheeks.
"Oh nothing" was the reply.
"Must be something or you wouldn't be here."
Her cheeks flushed bright red as she replied "Its just that all the girls at school say I look like a cow" she pouted.
"I'm sure they're just jealous" he answered. "I think you are a very pretty woman Karen." (and he meant it)
"Do you really think so?"
She was clearly pleased with his answer and continued "So you don't think they are too big, I mean, you know..." she said looking down at her chest and again blushing profusely.
He was taken aback at her question but recovered quickly.
"Don't the boys like them?"
"How should I know?" she retorted "Do you think I'm dumb enough to ask them?"
"Well, you asked me..."
"Yeah, but you're different." She looked up at him with her bright eyes and a bit of a smile.
For some reason his normal reserve when dealing with students failed him and he was taken over by a desire to see the young woman in front of him naked. Perhaps, in part, it was due to the already noticeable swelling in his pants (he had a special fondness for women's breasts and Karen looked like she had rather nice ones). Perhaps the fact that he had been divorced for over a year and hadn't had sex (or even thought much about it) for most of that time.
At any rate he found himself saying "You know if you want a real expert opinion why don't you unbutton your dress and show them to me? It's hard to say when they are all covered up."
She gasped "But Mr Downs, that would be really naughty! I can't do that!"
"Don't worry, I won't tell anyone. Here, let me help." He reached toward the row of buttons.
"No! I'll do it, but you mustn't tell, not anyone."
She was feeling shy and embarrassed and bold all at the same time. She had had a secret crush on Mr. Downs most of her senior year although he had never seemed to pay much attention to her. For some reason, despite her normal shyness, she really did want him to see her tits and get his approval. After all he had probably seen a lot of girls naked boobs before she told herself. She hadn't had a clear agenda when she made the appointment other than the fact that she would be graduating soon and wanted to see him once more, alone if possible, but the direction they were headed now caused a surge of unfamiliar excitement.
She began undoing the buttons one at a time as he watched, his cock, already somewhat swollen, began lengthen in anticipation of the sight to be revealed. She reached the bottom of the set and shyly pulled the front of her dress open. Her full fat mounds completely filled the cups of her bra and swelled out a bit over the tops as it was probably a size or so too small for her. Likely her attempt to minimize their appearance.
She looked up at him in anticipation of some judgement.
"Do you want me to help you with the bra?" he asked "Taking it off I mean?" He was all in now, all caution discarded as she stood there in front of him with her dress pulled open.
She blushed furiously and stood there speechless.
"Here, turn around" he said. Taking control of the situation he put his hands on her shoulders and turned her around.
She let him, starting a bit at his touch and again as his fingers sought the clasp beneath the thin material of her dress and deftly unhooked it. With his face so near her he noticed how nice she smelled, clean and soft. He had nearly forgotten what a woman smelled like and he inhaled deeply as he put his hands on her shoulders and slid the dress and the bra straps down her arms a little before reaching down in front and pulling the cups up to release her breasts.
Soft and spongy they did droop down a bit, despite standing out proudly from her chest, and had large puffy pink areolas. Her nipples were soft and barely showing. He slid his hands down and cupped them, squeezing gently and then running his thumbs up over the nipples and back till they began to jut out, and then squeezing them again. Even though his hands were quite large they more than filled them. They felt wonderful and having them in his hands he was reluctant to remove them - and she offered no resistance.
She had just stood there in shock at first but now he felt her arch her back slightly, pressing the soft mounds against his palms.
"I think you have very beautiful breasts Karen. Do you like it when boys touch them and suck on the nipples?"
"Oh my god Mr Downs! Do you think I would let a boy do those things??"
"Well, do you like what I am doing now?"
"No...well a little, I mean please don't stop..."
