Guidance Counseling

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..."

Her nipples were fully erect now and her skin was flushed. Having gone this far without resistance he decided to go for more territory. He slid one hand down over her soft smooth belly and toward her crotch. She shuddered and then gasped as his fingers began to massage the area between her thighs.

"Mr Downs! That's really very naughty!"

"Does it feel nice?"

"Well, I don't really know. It kind of tickles in a funny way."

"Why don't you pull up your dress Karen. It will be easier for me, and don't worry, I won't tell anyone."

He could feel her hesitation but then she reached down to the hem and pulled it up to her waist. "Like this?" she whispered.

The naughtiness of what they were doing had begun to excite her so much she no longer had any ideas of resisting what Mr. Down's hands were doing to her. In fact, she wanted very much for him to continue.

He reached down under the folds of fabric between her thighs and brought his fingers up till they were cupping the soft panty covered mound. She let out a small gasp as his fingers began to rub and massage the mound, exploring it and feeling for the slit in the middle.

"How does it feel now?" he asked.

"gooo ood" she said, a little breathlessly and then gasped again as he pressed a finger against the spot at the top of opening to her most private place.

"Why don't you slip your panties down now" he said, while continuing to massage her and kissing her on the neck.

"Are you sure you won't tell anyone?" her voice quavered a bit but she did as he asked moving the white cotton panties down toward her knees. She couldn't push them lower as he still had one hand on her breast.

His fingers now were exploring bare skin and the soft downy hair that covered her sex, and then one slipped between the fleshy mounds and slipped up inside her. Karen was breathing hard now as his fingers began to rub that special place and then dip inside her. She was getting very wet and his fingers were rubbing the slippery wetness all over her opening and making little wet sounds as they began to rub faster and faster. He pulled her bottom back against his crotch and began rubbing his fully erect cock against her.

"Are you going to have sex with me Mr. Downs?"

"Yes Karen"

"We shouldn't do that you know..."

"Yes Karen, do you mind?"

"I don't know, I don't think so."

She was thrusting her pelvis against his hand now and moaning softly as excitement built between her legs. Maybe it was his bright blue eyes and the way they looked at her that disarmed and turned her on so much, or maybe the way his hands felt on her body. Whatever the reason, she had decided that losing her virginity with him was the best possible fortune knocking on her door.

Still keeping pace with his fingers in Karen's pussy he moved the hand from her breast down between them to the button of his pants, undoing it and letting them drop to the floor and then working his underwear down sufficiently to free his dick. Pulling his hand from between her thighs he turned her around, hoisted her dress and pushed his erection down between her thighs (the platform sandals helped). As he bent down to take one of her nipples into his mouth he began to move his cock back and forth between her legs, coating it with her wetness till it was thoroughly slippery.

He eased her down on the couch and removed her panties. Then moving her thighs apart he knelt between them and putting his hand down to grasp his shaft, he leaned forward and began to rub the head against her pussy, searching for the opening. Karen watched with growing excitement as his hard cock pressed against her and then found its target and pushed inside. He felt a slight resistance, withdrew a little, and then pushed on past it causing Karen to cry out as his hard shaft sank halfway into her.

"Are you OK Karen?"

"Yesss, don't stop, please don't stop!" Her voice was a combination gasp and hiss, a little pain mixed with pleasure. "It's just... it seems a little big... are you sure it will fit?"

"Don't worry Karen, I'll be careful."

He kissed her on the lips and the neck and then sucked on her nipples as he began to slowly withdraw and thrust, withdraw and thrust a little deeper each time. Karen's pussy was tight, but very wet, and soon he had managed to bury the entire length of his hard shaft within her.

He pushed up with his hands rising up so he could watch her body and see his cock, wet with her juices sliding in and out of her virgin pussy. Her fat breasts were rolling back and forth on her chest with each thrust, the nipples standing up proud and red from his sucking. Her eyes were closed now and she was moaning softly. The sight drove him wild with desire.

He tried to maintain his slow pace but it wasn't long before he felt his balls tighten and he laid back down on her and wrapping his arms about her held her body tight against his and with a series of deliberate thrusts he began to deposit his load of spermy semen in the depths of her pussy. He came hard, harder than he could remember, and with each thrust semen spurted out in a torrent.

The pleasure was so intense it almost hurt and he groaned with each spasm. Karen moaned beneath him, her pussy contracting around his pulsing shaft. It seemed to take forever for his cock to stop spasaming. He kissed her passionately on the lips and then on each breast before slowly easing his still semi hard organ from her depths.

"I felt something wet spurting inside me Mr. Downs, you didn't pee in me did you?"

"No Karen", he smiled, "that was my semen, just for you."

"It felt really nice Mr. Downs. Can we do it again?"

"Yes Karen" he said, his cock already beginning to swell. "But first I want to kiss you down here" he said, gently massaging her pussy before leaning down and placing his mouth on her sex.

She shuddered and moaned with pleasure as his tongue began its work and soon she was bucking her pelvis and pulling at his hair with her fingers, urging him on. Her body shuddered and she cried out as the climax washed over her.

He let her calm down a little before beginning to rub his now fully erect shaft along her slit, coating it with their secretions. She put her hands down to touch him, pressing the organ against herself.

"Is it always so big Mr. Downs?"

"No Karen, looking at your breasts made it get big."

"Oh, that's nice, I mean I'm glad. I like the way it feels. It fills me up all the way doesn't it?"

"Yes Karen, all the way."

"Does it feel good inside me?"

"Yes Karen, the best!"

He positioned himself and pushed, easing it back inside her and began rocking, enjoying the sensation of each thrust. He placed a hand on each breast, cupping and squeezing and rolling the nipples and she moaned and thrust her pelvis toward the source of her pleasure, urging him on. He kept his slow pace at first and then gradually increased it until he was pounding away furiously as Karen bucked and cried beneath him.

"Squirt your stuff again, I want to feel it again!"

He obliged, not being able to hold back, and with a groan began to pump her full of his sperm once more.

"Does it feel good when it does that? I mean when it squirts?" She asked when he had finally stopped and was resting on top of her.

"Yes Karen, it feels wonderful, and especially inside you."

"Can we do it again some time?"

"Yes Karen, I'd like that very much. Maybe if you come to see me next Friday. If you are feeling especially naughty you don't have to wear any underwear under your dress when you come. But you better wear your bra, otherwise people might notice."

"That would be very naughty Mr Downs!"

The way she answered let him know that she would come, and without her panties. Just thinking about it began to make him hard again.

"Do we have to wait till Friday?"

"That's the best day Karen because everyone leaves early. People might begin to talk if you come too often."

She pouted "OK, you're probably right."

"Shall we do it once more before you leave Karen?"

"I'd like that. How many times can you do it?"

"Usually only once Karen, but with you it seems to not get tired."

He was still inside her and already hard enough to continue.

They did it slowly this time, with a lot of kissing and him sucking on her breasts. Surprisingly he still produced enough semen to fill her again.

When they had finished he helped her get cleaned up and kissed her again while squeezing her breasts through her dress.

"Goodbye Karen"

"See you next week Mr. Downs."

As he let her out he realized that he had left the door unlocked. Luckily late on Friday the hall was empty and the offices were relatively soundproof. The thought that he had just had sex with a student without protection began to worry him as he drove home and he pulled in at a drugstore and bought a package of condoms telling himself that it was unlikely he had impregnated her and vowing to be more careful next week. Perhaps she was on the pill anyway he mused knowing full well that this was almost certainly not the case. At least the couch had come in handy. He had always considered it a bit of an annoyance.

He thought about her all weekend and it was all he could do not to masturbate as he wanted to save it all for their next meeting. He had decided that either he would use a condom or he would pull out and come on her breasts. The thought of his cum squirting all over her chest began to plague him and he had to struggle to keep from heading to the bathroom right then. The week dragged and he found it hard to concentrate on his work. When he saw her in the halls it was all he could do to keep from staring at her.

Friday came and the hours seemed to pass especially slowly. Maybe she had changed her mind? What if she had told someone?. He sat fidgeting at his desk trying not to think about her, about how erotic it had been when she undid those buttons on the front of her dress, how her breasts filled his hands...

He was already hard when she knocked on the door. He let her in, locked the door behind them and pulled her to him without waiting for her to speak, kissing her passionately. She moaned and rubbed her chest against him. He put both hands on her bottom and pulled her crotch against the bulge in his pants before reaching down and pulling up her dress. His fingers found naked flesh and her pussy was already wet in anticipation. Her hands slid down between them searching for the bulge and squeezing it before starting to undo his pants.

"I was thinking about this all week" she said, squeezing the prize she had now freed from his underwear. "It was driving me crazy!"

He turned her around and bent her over his desk before lifting her dress up over her waist. He took hold of his swollen shaft and pushed it between her legs in a frenzy of horniness and desire. She had to reach down and help him find her slit so he could shove it home. She moaned with pleasure and he reached around to grip her breasts and began pounding away with complete abandon.

Karen seemed to have an orgasm almost as soon as he was inside her. She moaned and her body shuddered and her pussy tightened around his thrusting cock. He was so pent up with desire that he was cumming almost before he knew it, the great torrents of semen exploding inside her soon began squeezing out and running down her thighs. Karen came again as he ejaculated. He collapsed on top of her as he finished, his cock still pulsing weakly inside her.

"Wow! That was even better than last time. You really squirted a lot!" she said feeling his cum running down her thighs.

He stood up and allowed his cock to slip from between her legs. It was followed by a small flood of semen that dripped down and pooled on the floor between her legs. He pulled her to him, squeezing her breasts and kissing her neck.

"Yes it was my sweetie. I can't remember when I last came like that."

She turned to him to kiss him on the lips, her hands wandering down between them to play with his dick.

"How do I get it big again?" she asked pulling on it and squeezing it gently.

"That helps, or kissing..."

"Kissing? You mean sucking don't you. I've heard about girls doing that to boys."

Karen knelt in front of him and without hesitation took him into her mouth. She was still very horny and intent on getting fucked at least once more that afternoon, and anything she might do to ensure that she was willing to try. She could taste his semen mixed with her own juices as she ran her tongue over the fat head with its little eye at the tip. She found the taste exotic, and not unpleasant. In fact it added to her state of horniness. She began to fondle his balls with one hand while the other held the shaft which had begun to swell noticeably.

His hands played with her hair and he began to thrust gently toward her mouth as she continued to suck. While she was inexperienced he found the sensations of her lips, tongue, and hands on him highly erotic.

"Mmmm that feels so nice Karen."

He let her continue till he was fully hard before pulling her up and moving with her to the couch. He undressed her completely before taking his own clothes off. This was the first time he had seen her completely naked and he let his eyes bathe over her for a moment. She had shapely calves and smooth thighs - not at all skinny but there was a small gap between them where they came together right below a neatly trimmed vee of curly light brown hair that covered the two fleshy mounds surrounding and hiding her entrance.