Mart 22, 2021

Tutoring Anastasia

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Anastasia was wet, more wet than she’d ever been, holding her sister’s hand. They we’re walking over to the Donaldson’s house and she was dripping with anticipation. Her sister Veronica was best friend’s with the Donaldson’s middle child, Lisa. During spring break from high school and college for Veronica and Anastasia respectively, they spent most days over at the mansion across the field. It was always more exciting over there, and Anastasia was hoping for an internship with the campaign office that Mr. Donaldson ran. She would ask him for tips, setting goals for her future and networking through him, her father had arranged for him to be a mentor for her.

That’s how everything had started anyway. Lisa and Veronica would play; dress up video games, monopoly or ping pong, all kind of immature things for 18 year old high school seniors but entertaining nonetheless. Anastasia wasn’t one to deprive her younger sister moments of joy, and she hadn’t been getting up to much more interesting stuff herself at that age. Meanwhile she’d sit in the office with Mr. Donaldson, sometimes helping him file, frequently asking him questions about her studies. Sometimes they sat in silence. Those times made her nerves hum and her knees go weak. Sometimes she would stand behind his chair with her head over his shoulder while they browsed work outfits for her in catalogues. Women’s office fashion was just beginning in the late 80’s and there were so many interesting options but sometimes her sense of style was a little unprofessional even though she was old enough at 21 to know better.

He would give opinions sometimes that seemed telling about what he personally found attractive. She’d started tailoring her shopping to fit that. Today she wore something reminiscent of Princess Di. Very adult, so grown up feeling that she almost felt like she was playing a naughty dress up game for him. A dark blue wide shouldered 2 piece skirt suit, white gloves, lined panty hose with kitten heel Mary Janes. Her hair was pulled back with a scarf. For panties she had on lacy frilly French cut ones made of silk. Her bra was white lace as well and barely covered her nipples. Her nipples were wildly hard from grazing the lace, she worried that they must appear more prominent than the large white buttons decorating the front of her blazer. She wore dark lipstick with eyeliner and blush. Putting on her clothes today had felt as sexual as sliding her fingers inside of herself.

She was unconsciously squeezing Veronica’s fingers way too hard in her excitement. She took a deep breath and loosened her grip. Today was going to be the day. Mr. Donaldson was a widower; his wife had died right after the birth of their youngest child out of three. Everyone told her that Mr. and Mrs. Donaldson had been very in love. He had never remarried or as far as anyone seemed to know, taken another lover. That alone excited Anastasia. Her own father and mother hadn’t seemed to love each other much and her father had never shown the love and care to her and her sister that Mr. Donaldson showed his children. He was more like the men in the romance novels she liked to read alone in her room. He also showed her every kindness and never made her feel uncomfortable like all of the rest of her father’s friends who frequently stared at her breasts and sometimes grazed their hands against her ass. Gentleness in a powerful man, Anastasia was learning, was just about the most attractive thing there was.

She had spent many days with Mr. Donaldson recently, and over the years. She had decided, a while ago actually, that she wanted him to be her first sexual partner. He had never hinted at any interest in that, but she was holding onto hope that if she made a move he would reciprocate. She’d had no real experience with boys or men so far, but she was a fairly confident young woman. She hadn’t been raised vain like many of her classmates who had more polished appearances; the emphasis had been on her studies and athletics, not on dances and boyfriends.

She was larger than many of her classmates, proportionally. She had shot up to six feet tall in sophomore year; she had broad shoulders and wide hips with thick thighs from playing basketball, rowing and volleyball. Primarily raised by her father once her parents divorced she hadn’t learned much about makeup or how to do her hair. Sometimes her father had brushed her hair for her at night before tucking her in, which she had loved, but that was the extent of it. So her face was generally bare and even when she wore makeup it was scant because she was aware of how clownish it started to look when she applied too much. Her mousy brown hair had never been dyed and she wore it short but long enough to keep pulled back. But at school a fair enough number of people had told her she had a big chest and a large ass and she hadn’t taken it in a bad way. She was a little baby faced but she carried herself with maturity. She went through the list of her attributes frequently lately because she wanted to reassure herself that Mr. Donaldson could find something to like about her.

She had seen pictures of Mrs. Donaldson, antalya escort she was rarely made up and while she was definitely more delicate than Anastasia she was just as no nonsense appearance wise. They had similar facial structure. She didn’t particularly like making these comparisons. The adult love the couple had obviously shared made her nervous. It wasn’t something she was prepared for at all, more she wanted the kind and handsome Mr. Donaldson to act as her mentor in this area as well, and hopefully enjoy it if that wasn’t asking too much.

By now they’d reached the side of the house, Anastasia stood tall to peek into the living room window over the rose bushes there. Mr. Donaldson was standing there with Lisa chatting amicably, smiling as he finished buttoning the top button of his shirt and tied his tie. Anastasia felt a flutter of nerves in her belly and the heat kick back on in her core. Suddenly he turned his head and caught her eye; he beamed a huge white grin at her and motioned her around the house to the front door. She yanked Veronica’s hand and went running for it.

Mr. Donaldson had been on her mind for years now. She imagined his cock was large. She’d think about him in his suits, this already imposing man with something so much more imposing underneath those neatly pressed clothes. Thought about what he must do when it gets hard. Holding it in his hand and stroking it as it throbbed, running his thumb over the tip as his heart beat faster and his breath came in short gasps; shooting cum onto his stomach and fist, covered in a dew of sweat. She’d think about how maybe he’d enjoy her putting his cock into her mouth. All the while sliding her fingers in and out of herself, getting wetter and wetter, the wetness dripping down between her thighs and she put first one, then 2, then 3 fingers into her dripping wet cunt. She’d slide her thumb over her clit and then into her pussy. She was tight, 4 fingers was a real stretch. She’d get close just from that thought, the thought of how much she was stretching her tight little pussy. If this at just the entrance of her cunt was a lot, imagine how good Mr. Donaldson’s cock would stretch and slam into her.

She’d get too close to cumming and pull her fingers back out and move them to her breasts. She’d wet her nipples with her own juices, squeezing her tits between her hands, holding the large globes stroking the sensitive sides. The soft delicate skin of her breasts would feel so good in Mr. Donaldson’s hands, she was sure. She loved the weighty heft of them in her hands; she couldn’t wait for how it would feel to have his huge hands cupped over them, still not any better able to contain them than her smaller hands were able to. She’d have resented her large breasts and how they affected her life and athletics if she didn’t enjoy playing with them so much. She was jealous of the other girls with their tiny perky breasts that didn’t require bras until she’d started masturbating and then she was certain they couldn’t be deriving the same level of sexual pleasure from their own bodies that she was. Maybe they were, but in any case she had stopped being jealous.

She’d completed this routine last night and again this morning. She had touched herself every night for years now but this proximity to Mr. Donaldson had sent her already high level of sexual interest into overdrive. She touched herself sometimes 4 times a day. Just last week Mr. Donaldson had leaned over her shoulder to read what she had written in her notes and afterward she had excused herself to the hallway where she’d lifted her skirt slid her hand into her panties and two fingers into her already dripping wet cunt and had orgasmed almost immediately; all while hoping that Mr. Donaldson would catch her. She then went back into the room fingers and thighs still sticky, fidgeting in her seat for the rest of their afternoon together.

The public masturbation was not new, just more frequent than it had ever been before. She had been a very good girl her whole life. No drugs, no drinking, no sex, good grades, kept to her bedtime, always followed through on her responsibilities. She was kind to her elders and cared deeply for her little sister. She was always a good little girl. She had found her outlet for her bad side and only needed to express naughtiness that way. She once went to all her college classes with a dildo inside of her and kept it in there for the whole day. During a family dinner last year she slid her fingers inside of herself under her cloth napkin and teased her clit for an hour while carrying on conversation with her father as she came. She wore vibrating panties to prom, she’d been so excited to purchase them from the local sex shop when she had turned 18, she went in with a scarf and sunglasses feeling very mysterious and adult. In her time with Mr. Donaldson she’d get so incredibly wet that she could sit on the edge of his desk and rock gently her panties sliding wet and tantalizing along her clit while she maintained eye contact with him. Once she had lightly cried out during her orgasm while doing that. He had touched her forearm in concern alanya escort that she’d hurt herself. She came again immediately.

She could not wait to get into his office. She was on such a fine edge today. Her panties were wet enough that it was spreading to her thighs and through her panty hose. Her nipples were aching so hard that she was almost whimpering. She wondered sometimes if there was any possibility that he could smell how aroused she was when he got close to her. She hoped he could. All of this would be so much more simple and quick if he would just catch her with her fingers in her cunt, knees slightly bent, back against a wall; fucking herself in his house, wet and sloppy, fingers in her tight little hole. But he never did.

Veronica and Anastasia burst into the door all smiles. They released their hands and went in separate directions, each pulled like magnets to the person they had come here for.

“Welcome back, Anastasia. Do you need a snack or drink before we head into the office for the day, my dear?” Her stomach fluttered again at the casual endearment. Her clit throbbed happily.

“I’m fine, Mr. Donaldson, thank you, sir.” She loved calling him sir. Her clit gave another throb and she squeezed her thighs together. “Let’s just go to your office.”

He chuckled slightly. “I sometimes feel like that’s your favorite room in the house.”

“Oh sir, it is my favorite room in the house.” She was such a good girl, she couldn’t help but be the picture of politeness even now, even as they walked down the hall to his office, which felt like being surrounded by his masculine energy, where she’d hopefully get fucked by him. She led the way to the office, feeling the usual spark as she reached for the doorknob the heat of his strong body at her back. She wondered idly if he had been watching the curve of her ass as she walked ahead of him. She turned the knob and stepped into the office, which looked like the classic ideal of an office/library in a large manor; everything dark and heavy, rich maroon as an accent color but mostly wood and leather. She sat down in her usual seat and he walked to behind the desk.

He was wearing a three piece suit; even though he was able to primarily work from home he was always well dressed for all the phone calls and typing. It was pinstriped charcoal grey and it looked amazing as far as Anastasia was concerned. He leaned back in his chair and regarded her. She had frequently imagined kneeling in front of that chair and taking his hard cock into her mouth while he gazed down at her. “What’s on the agenda for today’s studies, my dear?”

Despite her intense anticipation the question took her by surprise for a second. She suddenly felt bashful. How could she ask this powerful man if he would touch her? Surely he would have if he wanted to, he could have taken what he wanted a million times over if he had wanted it. She took a deep breath, again her nipples were stimulated by the white lace of her bra and she felt emboldened.

“I have something in mind for my studies today, sir, If that’s alright? I thought we might deviate from the study guide some.” She was almost breathless as she said all this. Things had taken on a very soft focus and she felt a little light headed. The sun was shining in through the big windows and she could see dust motes floating in the air. She was having trouble believing she was going through with this. She turned her gaze to him. There was a question in his eyes as he looked back, “What’s this idea?” He asked.

She stood up. She hadn’t actually considered this far, which was foolish because she thought about this day and night, but she found as soon as she started thinking about the big event her cunt would get hot and wet and she’d slide her fingers to her soaking core, tease her clit and her nipples and everything else would fade away. She walked to his desk and stood in front of it briefly while he regarded her. “That outfit is very becoming on you; you’re beginning to look like a very professional young woman.” He said this almost nervously, uncertain of what she was doing, how she was acting. She now circled around the desk to the side he was sitting on. She wedged herself between his knees and the desk, directly in front of him. Her butt propped gently on his blotter. Her fingers went to the first button on her blazer. She popped it open. Her face was stony but also hopeful at the same time. She popped the next button open. He was beginning to see the curves of her breasts pressed together in her bra. The next button popped open. There was no undershirt to this suit. A suit that was far too adult for this college girl to be wearing casually.

One more button and the blazer was fully open. She left it on but pushed it to the sides. More fitting her age, her bra was too small for the breasts it contained. They were squeezed uncomfortably tight and her nipples showed over the tops of the cups. Just lace covered them and they rose slightly above that as well. Before he could stop himself or really contemplate much of what he was doing he reached out. With his belek escort index finger he traced the top of that nipple, Anastasia whimpered. He leaned forward. She held her breath. He covered one nipple with his mouth through her bra and sucked, hard. She dropped her head back and let out a moan she’d clearly been holding in. A moan it felt like she had been holding in for years.

“Oh, my sweet dear girl, is this what you’d like to study today?” He said as he released her nipple from his mouth. He had sucked it hard into his mouth and then bit. It had hurt, and Anastasia was so close to an orgasm from it she wasn’t sure she’d be able to respond to him. But she was a polite little girl she knew that she had to.

“Yes, please, sir. I think you can teach me a lot about this subject, Mr. Donaldson. I don’t think it’s what daddy had in mind when he asked you to mentor me, but I’ve been studying it on my own and I think you’d be very helpful. Will you please teach me, sir?” He had started pulling the cups of the painfully tight bra down to reveal her nipples, rock hard, to the chilly air. The one he had bitten gave a throb, the one he hadn’t ached in a different way, clearly ached to be bitten as well. “Could you please bite the other one as well, Mr. Donaldson? It’s really achy.”

He chuckled, but obliged, breaking eye contact with her to lower his mouth to her left nipple; first wrapping his tongue around it while bringing both hands up to cup just that breast. Then he sucked it gently into his mouth, suckling at it like a baby would for a while. She slid her fingers into his hair and gently held his head as he suckled and suckled, keeping her moaning. Suddenly he sucked hard and bit at her nipple, surprising her with the pain. She gasped and squeezed her thighs together while pulling his hair in her hands. She had never been rough with herself before, she hadn’t realized she would like it, but she did. He pulled back breathing heavy. “Did that hurt too much, my beautiful dear?” She shook her head, still gasping, wanting more.

She shrugged the blazer off completely and he grinned at her. The cups of her bra were fully below her breasts, the huge swell of them hanging out revealed to him. The straps cut into her shoulders and the band was tight on her back and they were practically exploding out towards him. He smiled sweetly at the display and pulled her sideways onto his lap. With the back of his hand he gently grazed her breasts, barely there touches that kept her on edge. He’d lift one fully in his palm and then the other. Now that she was aware she liked the pain of a bite she was hoping for another. He didn’t give it to her though, for 15 minutes or longer he just stroked her breasts. They swelled and tightened under this level of attention and arousal. He worked an office job but he maintained the house’s garden and played sports so his hands were rough. They left pink scratches here and there on her pale white breasts. He’d scrape his nails on the outside edges of her nipples. He stroked and petted her. Just like a beloved dog he pet her and pet her. The back of his hand and then his palms, then just his finger tips, he stroked and pet her aching breasts. It was almost too much, it was almost agony. The way her clit throbbed in connection to these sweet pettings was unbelievable; like nothing she had ever experienced.

“My sweet, sweet girl, do you want me to stop?” He whispered this into her hair. The way his breath felt on her ear brought a hot wet gush from her pussy in response. She simply moaned, she didn’t have her polite words at her disposal right now. She wanted more, she felt crazed, but this felt wonderful, she could live in this feeling. Besides, good girls don’t beg and plead to be fucked like animals by their Daddy’s friends. And she was always a good girl. “I didn’t think so.” He gave her nipple a painful squeeze eliciting a moan and then continued stroking her breast.

After a few more minutes of teasing and stroking her breasts which were beginning to ache to be sucked by him again, he gently tilted her off his lap. “Take the rest of the suit off, my dear. Follow my instructions well, leave your panties on. Leave your gloves on. Once your panty hose are off, put the shoes back on. Can you do that?” She nodded and began to unzip the skirt from the side, then shimmy out of it. She squatted to unbuckle her shoes and gently kicked them off, took her socks off and then peeled her panty hose off. She knelt again to replace her ruffled socks and her shoes and then stood before him. When she knelt she bared her sopping pussy to the chill air of his office. She was quite a sight. Thick hips and thighs, large breasts bursting out of her too tight bra, high waisted lacy panties half soaked through, delicate white gloves and her slight heels still on. From the neck up she looked much as she had when she entered. The pearl necklace her mommy gave her at her throat, her light makeup still in place, hair pulled back and held with a filmy white scarf. It was quite a contrast with her already debauched body lower down. It made her more adult while at the same time emphasizing her inexperience. She would have done literally anything he asked of her at this point. She gave herself over to the feeling of being a willing slave. He knew things that would feel better than she could ever imagine and she would walk across hot coals to experience them.

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