Steven Rodman had been a teacher for almost ten years now. He was an "old hand" in the public high school system and had survived several cutbacks without any problem. Today was a different story. He was informed by his union rep that his name was on a short list for layoff. It seemed almost unbelievable to him. He had never been in any trouble during his decade in the system. Sure the demographics were bad; too many middle class families were fleeing the district. It was inevitable that reductions were in the cards for most of the schools in and around the City. Yet, he thought he would be above this chaos because he had won "teacher of the year awards" almost every one of his years on the job.
Recently separated from his wife of two years, Steve, as one of the few male teachers, had felt secure in his position. At least, until about an hour ago, when vice principal, Sandra Worthington gave him the letter his union rep had given him a "heads up" about earlier that same morning. Steve was only 32 years old and his budding career had come to a screeching halt.
Sandra had tried to take the sting out of the dismissal by dropping to her knees and sucking his cock in frenzied abandon behind the locked door of her office. Just as he exploded inside the attractive 45 year old petite blonde's mouth, her phone rang with an insistent and jarring noise that jarred his already frazzled nerves. Steve put himself away and watched the vice principal wipe his creamy cum from her lips as she answered the call from the District Supervisor to confirm she had "attended to" the six unlucky teachers on this very unlucky Friday the 13th.
Steve kissed Sandra and thanked her for the nice blow job. She laughed and told him her door would always be open should he ever want to come back and visit. It was a generous offer. He knew she had a very demanding and somewhat abusive husband and 3 teenagers that were always getting in trouble. They had "found each other" right after his wife had dropped the bombshell on him of "her need to find herself". Steve discovered that need translated into a hunky divorced stock broker with a designer condo on Park Ave.
He was still in a state of denial as he entered the turnstile at the Subway station. The platform was unusually crowded and he realized this was a Friday before a three day weekend. The car he entered was not that crowded. At the very next stop, the opposite doors opened to a flood of passengers moving over from a local train. When Steve saw the mass of people, he moved to the closed door to get as far away as possible. The mob filled the small car quickly. It looked like he would not be crushed after all. Directly in front of him was a young girl of about 19 years of age. She smiled up at him apologetically as she bumped into him with her handbag. Steve was not certain, but thought the pretty young student looked familiar. He was certain that she was not one of his students. That would have been too embarrassing. To be bouncing up against one of his students. Then again, he didn't have the job anymore, so he would have to say, ex-student. Before the train closed the opposite doors, another local spit out another load of scurrying passengers and the pack descended on the express train like vultures squeezing into the still-open doors. The press of humanity pushed the young girl hard up against Steve's body. In an instant, his legs, groin area, tummy and chest was as one with a nubile young female form of impressive dimensions. He became immediately aware of two luscious rounded ass globes rubbing into his groin. His relaxed member became instantly aroused and it unfolded to take up residence in the gap between the two soft ass cheeks. He could feel the girl tense her ass muscles to close her defenseless crack. It was too late. All she achieved was too rub her ass cheeks on the sides of his shaft in a pleasurable standing lap dance.
The girl's body was so tight against him, he could feel her heartbeat. The noticeable increase in the rate revealed her agitation at the unintended impalement of her posterior. The rocking motion of the moving train acted to bring Steve to the edge of blowing his load between the soft cheeks of the girl riding on his rock hard cock. The point of no return took place when the girl leaned forward slightly to pull her book bag up from the floor. This slight movement caused the head of his cock to press hard against the girl's sensitive anus and triggered his flow of creamy cum to shoot up his shaft and spurt out in forceful spurts. The sticky cum shot straight through his boxer shorts and linen trousers forming a puddle on the young girl's pleated skirt.
Steve didn't know it, but the girl felt the swelling of the flow of cum down the hard rod in her bottom and she could also feel the wetness of the cum puddle on her skirt pushed deep between her ass cheeks. Her face was burning with embarrassment at the indignity of being impaled by a stranger with no way to prevent it. On the other hand, she had to admit it was so very exciting and her pussy lips were brimming with her own juices. In fact, she wanted desperately to turn around and feel the hard penis rubbing on her throbbing clit so she could get off herself.
Before the train pulled into the next express stop, Steve's hard cock had returned to its dormant state. The only visible signs of sexual arousal were the wet spot on his trousers and the little puddle of cream on the girl's pleated skirt. Steve stepped off the train as the door opened. Most of the standing passengers exited. Steve got back on the train and noticed the girl was now holding onto the pole facing him. He gave her a tentative smile and was pleased to see her smile back shyly.
"I have to get off at the next stop. I wanted to apologize for taking advantage of your being pushed up against me."
The girl put her hand on Steve's arm.
"It couldn't be helped, Sir. No harm done. In honesty, I kind of enjoyed it."
She giggled when she admitted her liking for Steve's cock.
"In that case, maybe we can follow-up with getting to know each other better. My name is Steve. And you are?"
"My name is Penny, Steve. Penny Worthington. I think I know you. You work for my Mom at the public school."
Steve remembered her now from the cookout at the school. She was only 17 then and he was still married to Ms. Bitch. He was still in love with his wife then and completely unaware of her affair with the playboy stockbroker. He remembered her wearing her private school cheerleader uniform and thought it unusual that her mother sent her children to a private school. So she was 18 and not 19 as he had first thought.
"Unfortunately, I just had to leave that position. Your mom was very gracious and I loved working with her. I guess we both get off at the same stop now, if you still live at home."
"Yeah, still at home. I go to Stanford University in September. I just got my acceptance letter. Is your pretty wife still working on Wall Street?"
As they both exited the train, Steve helped Penny with her book bag. It was pretty heavy. He wondered how the petite girl managed it onto the subway.
"Well, Penny, My wife has decided to move on to greener pastures. I am afraid the lifestyle of public school teacher did not meet her needs. Our divorce was finalized last month."
At the top of the subway steps, Steve asked Penny if she wanted a ride home. His car was parked across the street from the subway station and he knew Sandra's house was several blocks away. Much too far to carry the heavy book bag.
"Thank you, Steve, if it won't be a bother. I hate that walk because it is all uphill. It is so much better in the morning."
He put their bags in the back seat and put the air conditioning on full blast. Before they started, Steve took some tissues from the glove compartment and told Penny to lean forward in the seat. Then he wiped of the remaining sticky cream from her skirt without getting too familiar with her bottom. Penny was beet red when she sat upright.
"I hope I didn't ruin your uniform skirt. I think if you get it into the wash before it dries, it will not stain."
Penny looked down at Steve's trousers.
"You have the makings of a nice sized stain right there, Mister."
She took some tissues and blotted the wet spot right over his dormant cock. The sudden nearness of the young girl's fingers to his cock made it rise abruptly and push up at her stroking hand. Penny seemed not at all displeased at this. In fact, she looked up into Steve's eyes and in a quick movement she zipped him open and pulled out his now fully erect member. Steve's cock was larger than average and extremely thick. Penny wrapped her fingers around his shaft and stroked him slowly. His pre-cum oozed out onto her fingers. Penny switched hands and put the sticky wet hand to her mouth and licked his pre-cum off with a pointed tongue. It was so erotic that Steve came quickly to a climax and shot a gooey load of white cum onto Penny's bare leg. They both looked at the evidence for a silent moment. Then, Penney lifted her head up to Steve's mouth and he felt her pointy tongue push deep inside his mouth. It was as though Penny was trying to fuck his mouth with her tongue driving deep and sucking all of his saliva down into her tummy.
"Steve, I hate to ask you, but I have not gotten off yet. Could you make me go right now? I need it real bad. I just gotta have it."
With no further invitation needed, Steve lifted Penny's skirt and pushed her panties to the side. His fingers slid inside her vagina. They slid in easily because she was soaking wet with her own pussy juice. With his other hand, Steve reached behind Penny's upraised leg and pushed his thumb deep inside her pulsating anus. The action from his probing fingers at both ends brought Penny to a sudden climax. She put her head on Steve's shoulder and moaned like a lost kitten. He could feel her teeth biting into his suit jacket. The expulsion of pussy juice from her vagina and the convulsing of her tortured anus attested to her satisfying orgasm.
They both rested for a few more moments. Penny was holding his hand like a child who does not want to lose their parent. She looked up at him with the softest eyes he had ever seen. The hint of tears at the corners was a pull on his heart.
"Thank you, Steve! That was the best ever. I am technically still a virgin, I guess. But I have taken it up my ass from my boyfriend Adam a few times when he was not satisfied with me jerking him off or giving him a blowjob. I am just telling you so you don't get surprised if we get to do it all the way. I am a little afraid of having my pussy penetrated, but I guess I am long overdue to getting it opened up."
"Penny, nothing would please me more. But, we have to be sure to have safe sex, if you are not on the pill. You don't want anything to deter you from going to the University this fall. How about Saturday night? I will fix you dinner at my place and we can do it the right way in a nice, soft bed."
Penny nodded her head up and down and kissed Steve on the cheek. It was going to be hard for her to wait another 24 hours to be deflowered, but she would savor the anticipation of spreading her legs wide for this handsome man.
Finally, a real man was going to "make her do it" and her juices were running already as she pictured Steve on top of her.
Penny was just coming out of the shower when her Mother arrived home from school.
Sandra Worthington was tired after a long day as a vice principal. Her little relaxation time with Steve Rodman had given her new vitality and her afternoon had been spent daydreaming about Steve's long thick cock filling her vagina. She loved the way he stretched her so wide and the way he was able to touch her special g-spot without any effort. She looked at her daughter clothed only in a towel and envied her youthful skin and healthy glow. She thought to herself,
"That's how I looked 20 years ago."
Sandra was unaware that part of Penny's glow could be attributed to Steve's attentions both on the subway and in his car driving her home. The glorious orgasm made Penny vibrate with sexual energy. An energy that made her 19 year old body tremble with anticipation of losing her virginity in the next 24 hours. Sandra had no idea that both she and her daughter were fantasizing about the same man. She realized that Steve's termination in the most recent cutback meant no more lunchtime blow jobs and no more desk bend overs with his beautiful cock sliding into her well-lubed ass hole.
"Hi, mom, how was work today?"
Normally, Sandra would just say everything was just fine, but tonight she felt a little blue about Steve's departure.
"Had to let some of the teachers go today, honey. Including that nice Steve Rodman. I will really miss him."
Penny was amused at her mother's comments. If she only know how well acquainted her only daughter was getting with her precious Mr. Rodman.
"That's a shame, mom. He seems like such a nice guy. When did he split with his wife?"
Penny was playing it cool and she wanted to confirm what Steve had informed her about his marital status. She had been lied to so many times by guys at parties and in clubs; her suspicion level was always high. She was sure Steve was leveling with her, but it didn't hurt to be safe instead of sorry.
"I thought I told you, dear, his wife left him about a year and a half ago. He was devastated. I felt so sorry for the poor man. I did all I could to counsel him and give him consolation. As his immediate superior, I mean! He is such a good teacher. I didn't want to lose him. As a teacher, I mean!"
Sandra's daughter gave her mother a funny look. She had caught a vibe from her mother that her concern for Steve was not just as a boss for her employee. No, there was definitely something there that her mother was not telling her.
Penny frowned. Then, she smiled, safe in the knowledge she had always been able to get any secret from her mother. It was just a matter of time. Meanwhile, she was looking forward to tomorrow night at Steve's apartment. Slowly, she moved back into her bedroom. Her hair needed brushing and she wanted to do her toenails in that nice pink shade for Steve to enjoy right after dinner. Penny expected him to explore her from her hair to her toes and the ever so important places in between. She took two condoms from her top drawer and put them in her little party purse. She had been on the pill ever since she turned 18 but this time it was going to be sex deep in her baby making opening. The test runs in her pretty mouth and her very tight little ass never posed any danger to an unwanted pregnancy. This time was curtain going up time on her as yet penetrated pussy. She wanted Steve's cock in her so bad that she could almost taste it.
Penny lay down on the bed and got up on all fours. She looked over her shoulder at the large mirror on her bureau and saw her heart-shaped ass posed in a perfect doggy position. Her ass was her primary source of sexual pleasure the past year. The very first time she opened up her back door for a man's cock was at the beach at Coney Island.
It was the weekend of her 18th birthday and her mom and dad were under an umbrella on the beach. Her dad was on his phone as usual and her mom was stretched out sound asleep in the middle of chaos. The three glasses of wine probably had a lot to do with it. Her dad's friend from work, Mr. Thompson was showing her how to float.
Penny was not a good swimmer and was a little uneasy even in the shallow water. She never did remember Mr. Thompson's first name. She always called him Mr. Thompson and he called her "my little penny". She thought Mr. Thompson was being a little demanding with his hands all over her special spots like her bottom, her pussy place and her budding breasts. But, Penny was not turned off at all by his attention. She was flattered because he was so strong and handsome. He had to be over a foot taller than her and towered over her when they were standing in the surf. Suddenly, they were both jumping up and down in the surf as the waves came in and she felt Mr. Thompson's cock rubbing her swimsuit on her bottom.