The Shy Girl

Casey had always been painfully shy and as she had grown into a young woman of twenty her shyness had only become worse. Her southern family was very strict, and she was not allowed to date, nor have any contact with men outside of her family's church. Casey had grown into a lovely young woman, dark brown hair, small firm breasts capped with stiff pink nipples, and long shapely legs. She was the kind of girl that did not immediately attract men's attention, but she was a quiet kind of pretty that grew on the people around her the longer they knew her.

The problem was that now she could not even look at the few young men who tried to chat with her, her face would flush red and she would not even be able to stammer out a reply to their simple attempts at conversation. That is why she was still technically a virgin, only technically because she had an active fantasy life that was her deep dark secret.

Casey enjoyed masturbating, and would use her fingers to penetrate her tight pussy, finger fucking herself where no hard cock had ever been. She wondered how she had even learned to do that her parents were such prudes. Her mother had told her about what she called the, "evils of sex" when Casey had started to develop into a woman and had done everything possible to make sex sound as horrible as possible. When Casey turned eighteen her mother had described in fairly vivid detail how the man's cock would grow hard with lust and then he would take the woman, piercing her body with his manhood, that there would be blood and pain. Now she wondered how her parents had ever conceived her they were so uptight about sex. They probably considered her the product of their weakness. Her mother had never told Casey about the pleasure of sex. Casey had discovered that on her own, in bed as her fingers explored her body.

She still remembered the first time she had masturbated herself to orgasm, her fingers rubbing her small, stiff clit, her fingers tugging and pulling her nipples, the pleasure building and building until she finally climaxed. Her head had exploded in pleasure; she had to bite her lip to keep from crying out. She remembered her hips pumping, instinctively thrusting as she pleasured herself. After that Casey realized that her mother had not told her everything, that there was a whole different side to sex she was just that she was waiting to explore.

She had listened to her friends to learn more. She did not have too many close friends, but her closest friends, Pam and Amy talked about sex constantly. She heard how they would give their boyfriends blow jobs, she could not imagine sucking on a man's cock but apparently they said it drove men wild. They talked about jacking off their boy friends and how their cum would spurt from their cocks. They talked about how their boyfriends like to feel their tits; both Amy and Pam had big breasts, double the size of Casey's own tits. Casey did not add much, but she listened and she started to imagine how it must be to have sex with a man.

She was fantasying tonight as she lay on her bed naked and masturbating. She was thinking about the tall blonde boy in her math class that had broad shoulders, a thin waist, and long powerful legs. She imagined that the blonde guy was on top of her thrusting his long, thick cock into her tight, wet pussy. Her fingers were busy stoking her clit, and finger fucking her tight hole. She could feel that she was close to orgasm, and she planned to masturbate over and over until she was exhausted. Her parents had gone to a meeting and that gave her hours to play with herself.

The man watching through the window was jacking off as he watched her. The girl was really going at it and he was matching her stroke for stroke. The man liked to watch naked women when they did not know he was there and it was a rare bonus to find a woman having sex, or masturbating. As he watched the slim girl rammed her fingers deep and pumped her hips as she reached orgasm. The man jacked his cock hard and ejaculated his load of cum onto the side of the girl's house as he listened to her moaning in pleasure. He was even more surprised as the girl continued to keep at it, her fingers stroking her clit and pulling her nipples, driving herself towards an even bigger climax. The watching man was glad that he had his digital camera with him and he quickly snapped off as many pictures as he could over the next 20 minutes as he watched the girl bring herself to climax after climax.

The man had been surprised to find this girl masturbating as he knew the neighborhood well and this girl was not one who ever struck him as being sexual in anyway. He laughed as he thought about the fun he would have with the pictures he had taken and how she would react when she saw them. He wondered what she might be willing to do to prevent him revealing his photos to her parents.