The Shy Girl
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa, Blackmail, Humiliation, Gang Bang, Interracial, Black Male, Anal Sex, Masturbation, Exhibitionism, Voyeurism, Size,
Desc: Erotica Sex Story: Chapter 1 - Casey is a very shy and sexually repressed girl. Her religious background and overly protective parents have made her feel only shame about sexual pleasure. She is caught on film by a man who watches her masturbate and she is given a wicked choice.
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 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 fantasizing 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.
Casey woke up the next morning and got ready for class like she always did. Her parents were their usual boring selves as she joined them for breakfast. "Remember dear our women's group meets tomorrow night at 8:00," her mother had said.
"I hope your getting all A's. That damn college is killing me with the money I have to pay and I want to make sure you are doing your best."
Casey had reassured her father that she was putting forth her best work and headed off to class. The man who had watched her the night before slid into Casey's house through an open window. He made certain modifications in Casey's room, and left her a little surprise.
Casey returned home about 4:00pm from school and went into her room throwing her book bag on the bed. She glanced over at the window and was surprised to see what looked like a flyer taped to the outside of her window. She walked over closer and was horrified to discover it was a picture of her naked and masturbating. It looked like it had been taken just the night before. She opened the window and ripped the picture down, crumpling it in her hand. 'Oh, my god she thought to herself. Someone was watching me touch myself. Oh, my god what if my parents find out. Her face was red with shame, and she looked down at the crumpled picture in her hand. She notice some typed words on the back of it that she had not seen earlier.
She smoothed out the paper and read the small typed words on the back: "I hope you enjoy the picture that I left for you. I know that I enjoyed watching you finger fuck your pussy. I jacked my cock while I watched you. Now if you don't want me to give these pictures to your parents you will do exactly what I say. Outside your front door under the large azalea bush is a paper bag. Go get it and read the other instructions inside."
Casey's stomach felt sick, and she was so embarrassed that she wasn't even sure her shaky legs would make it to the front door and back. She fought off the urge to run and hide and instead went out and found the bag under the bush as she had been instructed.
Taking the bag back into her room she opened it. Inside was an ear piece that looked like something that would be used with a cell phone, and a large thick piece of plastic. She realized that it was in the shape of a man's cock when she pulled it out. Casey had never seen a hard cock before and she had not imagined that a cock would be so big. She could not resist and she gripped the hard rubber cock, feeling it like it was real. She could no imagine how such a monster could ever fit inside a woman. There was a note in the bag that she should put the ear piece in her ear. She did so and was rewarded with the sound of her black mailer's voice.
"That's a good girl," she heard the voice say. It was altered, almost like one of the computer voices she had hear on TV shows. "Keep doing what I say and we can make sure your parents don't find out what a nasty slut they have for a daughter."
"I am not a slut Casey said out loud. The man could hear her as there was a small microphone built into the ear piece and said, "You would be a slut if you ever had the chance to be with a man. You would like being fucked wouldn't you Casey. You like to think about being fucked don't you?"
Casey was so embarrassed she could not answer him. Her face turned beet red and she lowered her eyes to her hands. Then the man said, "Now here is what I want you to do..."
What I want to see is you fuck yourself with the dildo. I want to watch you get off on a man's cock, even a fake cock. Do it now before your parents get home. Otherwise you can expect your dad to get a special delivery at his work. A few dozen shots of his virgin daughter fingering her tight, wet pussy ought to wake him up."
Casey immediately felt two feeling course through her body, the first was horror, how could she ever put that thing inside herself? The second was a kind of thrill; she felt so sluttish and nasty and the thought of using the dildo made her pussy tingle and grow wet She said to the man in a shaky voice, "I can't do that please don't make me do that. I have never done anything like that before. Please!"
I watched you stick your fingers up your pussy, so I think you can do this, the man replied. "Unless of course you would rather me just send the pictures to your father, it is really your decision Casey."
"Oh, God no don't even think that. I'll do it; I'll masturbate with the dildo."
"That's better, why don't you start by touching your breasts for me. Leave your clothes on, just take off your panties, unbutton your blouse and pull your bra up. I like to watch women pull their nipples."
Casey did as he asked pulling her white panties off from under the dark navy, knee length skirt she was wearing, and unbuttoning her white blouse pulling her conservative white bra up revealing her small tits to the watching man. She started to lightly stimulate her nipples making them swell and grow erect on her small breasts. In spite of her extreme embarrassment she could feel herself becoming excited, desire growing within her body.
She could hear the lust in his voice as he said, "That's it Casey pull your nipples for me, make them nice and hard. I am jerking off watching you touch yourself."
Casey had a thought, "How can you see me she said. I closed the curtains tight when I got the picture from the window, oh my God do you have a camera on me or something?"
He heard the watching man chuckle, "I can see you, which is all you need to know, and how I do it is none of your business. Now hike up your skirt and start to rub the dildo into your cunt hole."
Casey let go of her engorged nipples, and slowly hiked up her skirt, showing the watching man her dark furred cunt. She ran her fingers up and down her twat and realized that she was already soaking wet, she stifled a moan as her fingers caressed her cunt lips, and her fingers were quickly coated with her lubrication. She took the big fake cock and rubbed it up and down her wet pussy, quickly coating it with her cunt juice. Her excitement was growing and she did not even need the watching man to prompt her to start to penetrate her tight fuck hole. She pushed the fat head of the dildo into her pussy, sliding it slow into her twat until she had taken half the length into her tight virgin hole. She slowly slid it out and then shoved it back in getting more forceful as her tight cunt loosened up and accepted more and more of the hard dong.
Casey looked down at her cunt and saw that her pubic hair was soaked with her lubrication, matted and wet, her cunt lips were swollen with lust, and her clit stuck out hard and erect between her swollen cunt lips. She moved the fingers of one hand to her clit and started to rub it back and forth in time to her slow fucking of her twat with the big fake cock. The watching man was in her ear, talking to her, "That's it dirty girl, masturbate for me, make yourself cum. I am jacking my cock while I watch you fuck yourself. Ohhhh, I'm cumming I spurting my cum thinking about you."
Casey was over the edge too and as orgasm gripped her it was all she could do not to scream loudly in pleasure, her grunting exertions were loud enough and she drove the hard cock deep as she rubbed her clit vigorously, bringing herself to peak after peak.
She finally came back to earth and she heard the watching man in her ear again, "That was real good baby. Meet me here at 2:00 tomorrow and we will go for round 2."
Casey almost cried, "Round 2? Wasn't this enough? How long do you expect me to do this for you?"
"Just be here tomorrow or your dad will get a surprise you probably won't like."