Ugly Ducling

Or: The Randy Tutor and the Reluctant Student

Janie was a typical ugly duckling; at twelve years old she had been chubby and self-conscious, but in the ensuing five years she had developed, growing taller and her figure fining down, and at eighteen she was still a virgin, although her full and curvy figure attracted attention. She had big breasts with large aureoles. Although she had become popular with boys, her natural reserve had never permitted any familiarities beyond some fumbling over her clothes.

Janie was an average student, but her grades in maths were failing, and so her mother engaged a tutor to assist her in catching up on her maths work. Her maths tutor, who was her high school maths teacher and was about 40, came to the house, and as Janie studied in her bedroom, that is where the tuition took place, with Janie's desk pulled up to the bed, where she and her tutor sat side by side.

The day came when Janie's mother, who was out of town attending a wedding, was unable to return home as torrential rain had caused surface flooding, and was forced to spend the night where the wedding had taken place. However Janie's tutor, although getting wet in the heavy rain, had managed to drive to Janie's home. Upstairs, as they sat side by side and Janie was trying to work out a maths problem, she felt something under her skirt and between her thighs.

Janie froze, but acting quite casually, her tutor told her to carry on with her sums. His hand eased further up her thighs, reaching towards her panties. As his fingers reached her panties, Janie closed her legs and asked him to stop, however he told her that he could make her feel heavenly, wonderful, adding that he could help make sure she passed her exams.

Janie was scared, yet relieved at the thought of passing her maths exam, so reluctantly agreed to let him proceed. In an instant he was upon her. She wasn't wearing a bra, and as soon as he removed her tee shirt he attacked her breasts like a hungry animal, grabbing them to squeeze and bite them in a frenzied assault as if inflamed with lust at the sight of her big aureoles. Moaning in pain, Janie begged him to please go slowly and be gentle, but he had no intention of leaving her alone. He wrenched her panties off and began to finger her pussy, penetrating her and stimulating her clitoris to hardness, which Janie quickly discovered she loved. The combination of the pain he was inflicting on her breasts coupled with the pleasure from his fingering was conflicting yet incredible, creating sensations Janie had never before experienced.

He told Janie to spread her legs. She was initially reluctant as she was embarrassed about having a lot of hair on and around her pussy, but he was not deterred and it seemed to further excite him. Getting between her thighs he began using his tongue on her, spreading her pussy lips wide with his fingers to probe inside and lap at her swelling clitoris, creating waves of warmth throughout her body. Although Janie could only imagine what he was doing, she loved the sensations his tongue was teasing from her body, and allowed herself to lay back and surrender herself to pleasure, feeling herself becoming very wet.

Then he took off his pants, breaking the spell. Janie was shocked and horrified. She had never before seen a cock, let alone an erect one, and his erection looked huge, scaring her. He told her to rub and massage it, but she found herself unable to do so initially, but at his urging massaged it a little, and then he asked her to take it in her mouth. Opening her computer he went to a website and showed her pictures of girls taking cocks in their mouths, asking her again to take it in her mouth, but she was not ready to do so. Frustrated, he threatened to fail her in maths. Scared, Janie asked him to lick her pussy some more, or play with her breasts, but not to ask her again to suck his cock, which looked ugly and threatening.

At that he asked if there was ice cream in the house, and told Janie to fetch it. Spreading some on his cock he told Janie to lick it, and she finally agreed, licking the end of his penis, but as soon as she opened her mouth and began licking him he grabbed her hair and pushed his cock deep in her mouth. Without having any choice, and to prevent him choking her with his cock, Janie began to suck him. However almost immediately her stopped her, showing her some blow job videos and asking her to do it to him like that, and then Janie found herself sucking like the girls in the videos, doing it just as he had asked, and she found she was beginning to enjoy it.

He was grabbing her boobs again as she sucked him, further exciting her, and then he took his cock from her mouth and told her to spread her legs wide. Without further foreplay he moved down between her thighs, and spreading them wide stabbed his cock into her tight virgin pussy. Janie screamed, it felt as though something red hot and thick had speared her deep in her pussy, but once he was in and moving the pain began to fade; he was sucking, squeezing and pinching her breasts, she could feel herself opening up in response to his steady thrusting and her pussy no longer felt tight. She felt she was in heaven, was moaning in pleasure and begging him to do more, and climaxed for the first time. As soon as she came he immediately pulled out and spurted his spunk on her stomach.

From that time on the couple regularly had sex in her room, closing the bedroom door and having sex for three hours while pretending to be studying. After that first time he brought condoms and they had sex together on most days for a year, often involving extensive foreplay and oral sex. He loved her breasts, seemingly enraptured by them, and would often grab for them as soon as he entered her room. In turn, Janie quickly learned to worship his dick, teasing, sucking, massaging it, and probing the slit in the end with the tip of her tongue to increase his pleasure.

Her maths tutor became her teacher in the arts of sexual pleasure, and Janie was an eager and enthusiastic pupil.

Doug Campbell 15.10.2020

(as told by Fairleigh Avydd, a.k.a Bigaerolachick)