As Sheila Moser, Assistant principal and Guidance Counselor at LHS, knelt naked in her office sucking the cock of one of her students, she wondered how she got herself into this dangerous position and thought back to when it started.
About twenty years earlier she had been the best looking girl in her senior class at LHS. She was voted Homecoming queen and Senior Prom queen and a year after graduation she was elected the region's Festival Queen. Her long wavy black hair framed her classically beautiful face. Dark eyes and full lips along with a curvy body on a five foot four inch frame, she was difficult to resist. But being told you were gorgeous your whole life can lead to conceit and that is exactly what happened. On the outside Sheila would smile and give out an occasional compliment to others but on the inside she thought little of anyone but herself.
As a result when she finished school and the richest man in town showed interest, Sheila jumped at the opportunity. After a short affair he left his wife when Sheila told him she was pregnant, though he never discovered it wasn't his child. Sheila enjoyed spending his money and living in the largest house in town but a few years later when he died of a heart attack she was surprised she had spent most of his money and that he had no insurance.
Sheila secured a job at LHS as assistant principal which required her to discipline the students and hand out punishments, a role she was well suited for because she was thought to be mean by the majority of the students. She was also made guidance counselor even though she did not have the qualifications. What she had was the ability to seduce the principal and superintendent into giving her the position in exchange for a few nights each of romance.
Thus she was able to pay her bills and raise her daughter Sierra who turned out to be as attractive a young woman as her. But about the time that Sierra reached eighteen and her senior year at the school, Sheila looked in the mirror and noticed the signs of age creeping up on her. Lines on her face, a few extra pounds and other things that might not have been obvious to others scared Sheila to death and now she had been having trouble sleeping because of this fear. She had always been dependent on her looks and now, she thought, they had begun to fade.
Possibly due to her fear of losing her looks Sheila had started to have dreams about one of the students that her daughter Sierra had been dating. (Sierra rarely dated just one boy at a time. She liked to see them compete for her affection.) Jason, like his Greek namesake, had the body of a Greek god. Now a senior, he was an athlete and starred in three sports. His long, curly blonde hair and blue eyes stunned the female population of the school, including the teachers and staff.
Even though he could get just about any girl at the school, he wanted Sierra. But she played head games with him and strung him along while going out with other boys. When he would come to their door Sheila couldn't help but drool over him. True he had an eighteen year old mind but she ignored that and concentrated on his looks. When Sierra would invite him to share the pool with her, Sheila would go to a window and stare and fantasize about running her hands over his sculpted body. At six feet tall and one hundred seventy pounds there was little fat on him.
Sheila herself had become frustrated with dating. There were few men around that she felt were worthy of her. She dreamed of having a man like the ones she had in her youth. Though there were many students at school who gave her lustful looks, Sheila knew that indulging herself with them could lead to trouble if not prison. As a result of all her frustrations Sheila began to drink.
When Sheila would watch Jason from the window, strip down to his trunks by the pool she often had a drink in her hand and she could feel tingling in all the right places in her body. So when the day came for Jason to enter her office for guidance counselling, Sheila was a bit nervous. Before her stood the boy she had been dreaming about lately. It didn't matter that he was young enough to be her son; she could feel her blood pressure rise.
It was during this counseling session that Jason noticed out of the corner of his eye that Sheila was glancing at his crotch. Sheila was chewing gum but Jason could still smell the whiskey on her breath. Even though she was much older than him she still looked good and the idea of fucking a MILF like Sheila was not an unattractive idea to him. Although both were thinking similar thoughts nothing happened that day.
It wasn't until the following week when Jason showed up at Sheila's house right after school while looking for Sierra that trouble started. Sheila had just consumed almost a half a bottle of her single malt scotch when she heard the doorbell ring. She was wearing nothing but a red silk robe that hung just to her knees. She quickly put on some shoes and walked to the door.
Jason asked for Sierra and Sheila replied. "She's out and won't be back till late tonight." Then Jason asked to use her bathroom. She agreed. Jason didn't want to leave. On one hand he was angry that Sierra was probably out on a date with one of his rivals and on the other hand he didn't want to leave the sight of Sheila in a slinky robe. She was obviously nude underneath it and he could see the imprint of her erect nipples under the material.
As Jason stood in the bathroom pretending to be using it he suddenly realized why he was so attracted to Sheila. She had an uncanny resemblance to his favorite porn star Lanny Barbie. She could be her older sister, he thought. Of course Sheila, if you had asked her, would have no idea who Lanny Barbie was but most of Jason's friends did. Jason quickly thought out a plan.
Jason asked Sheila if he could swim a few laps in the pool. Sheila was pretty drunk so she agreed but stated that she would have to watch since it was a house rule that no one could swim alone because of the danger of drowning.
When they got out to the pool Jason stated that he had no trunks with him and asked if he could swim in his underwear. Sheila paused, took another sip of the whiskey and agreed. Then she sat in a chair and watched Jason strip trying not to be obvious about her enjoyment.
Jason's briefs quickly became transparent after diving in the water. As he made laps his breaststroke revealed solid buttocks and his backstroke revealed a bulging package. Sheila put on her sunglasses to hide her gaze. The more she saw the more she drank until she was tempted to jump in the pool herself. She hadn't had sex in over six months and she was going out of her mind at the show she was seeing.
When he finally came out of the pool he might as well have been naked. Sheila could see everything and her mouth was watering. Jason stood there next to the pool, his body all wet and every muscle pumped with blood from the exercise. He began to wipe off the water with a towel and then suggested that he couldn't wear his wet underwear under his clothes. He said, "Could you turn around while I change?"
Sheila stood up and turned her back as Jason peeled down his underwear. Then as she waited for his okay she felt his presence behind her. She pretended not to notice. Suddenly she felt his breath and then a kiss on the back of her neck. She stiffened but didn't pull away.
Soft, breathy, whiskey soaked words slowly crept from her mouth, " Jason...? Jason... don't." But the tone of her voice said yes.
Then his strong, damp arms encircled her, caressing her and pulling their bodies together. Sheila could feel a firm erection pushing up against her buttocks. She took one last sip of the whiskey and the glass in her hand fell to the grass beneath her. Passion and sexual frustration had taken control and there was no turning back. The fantasy she had dreamed of for months had taken control of her mind and body. She wanted what was behind her, pressing up against her back.
As Jason nestled his mouth against her neck, pushing aside her hair she could feel his hot breath on her ear. She kept her hands at her side but they began to tremble revealing what was in her mind. Jason knew that when Sheila did not turn quickly and push away that he had received the green light he wanted. He reached down from behind her and undid the tie at her waist and the robe fell open. Then he slid his cool hands inside the robe, feeling the heat of her body. His hands slid up and down her stomach until they rose to her breasts and encased them both. Her breasts weren't as firm as the teens he dated or as large as a porn stars' but they were large enough to fill his hands and firm enough to excite him even further.
Sheila's head fell back and her breathing began to speed up as he massaged her mounds. She knew this was wrong but her sexual passion was so strong that she convinced herself she would find a way around the trouble. That's when she felt Jason's hands peel off her robe. Sheila stood there completely naked except for her black high heels.
