Kevin wasn’t surprised that his mother gave him the cold shoulder the next day. He wanted to apologize for what had happened, but he knew that it would have been a lie. He had wanted it to happen and had dreamed about it happening since he was very young. There was no way he could apologize for that. While he knew that it was crazy to be in love with one’s own mother, after last night, for the first time, he thought that she might have some of the same feelings for him. The fact that she kissed him back and let him play with her breast, gave him hope. Still, she was married now, so Quentin had her, and he didn’t.
As Kevin sat sullenly at the breakfast table, watching his mother move around the kitchen, an idea came to him. Maybe he was trying too hard. He was the one that was jealous. Maybe a little jealousy might not hurt his mom. Suddenly he smiled and finished his coffee. He walked over to his mother, put his arms around her waist from behind, and kissed the nape of her neck. “See you later Mom. I love you,” he whispered into her ear.
Before Kathy could say anything, Kevin was on the way out the door. Her mouth opened but nothing came out. She had no idea what to say. Things had gotten out of hand last night. It couldn’t happen again. She wouldn’t let it. However, she could still feel his lips on her neck and little chills ran down her body, almost making her swoon. She grasped the counter and took a deep breath.
Kevin was whistling as he walked into the college administration office. He was in luck. Sherry Hayward was sitting at her desk.
Sherry smiled at him as he walked over and plopped down in a chair next to her desk.
Kevin liked Sherry. She looked a lot like his mom and was about the same age, with a good shape and a pretty smile. However, where his mom was five foot seven, Sherry was barely over five feet tall. Her diminutive size made her rather large breasts look even larger. She had very short brown hair and pretty freckles across her nose. Kevin made a point of talking to her whenever he could, almost flirting. He knew that she was divorced and without a partner for several months now. He planned to use that to his advantage.
“Hi Ms. Hayward,” Kevin said with his most seductive smile.
“Hi Kevin. I told you to call me Sherry.”
“Okay, Ms. Sherry,” he joked.
She smiled indulgently at his attempt at humor and said, “You’re early to class today.”
“Yea, I know but I just wanted to talk to you.”
“Nothing. I just like talking to pretty women.”
It was corn and she knew it. However, it was always nice to get a compliment. “Thank you Kevin,” she answered, blushing prettily.
Then, there was a long pause in the conversation and Kevin suddenly felt very nervous. His heart began to race. He looked down at the desk, playing with a pencil and said, “So do they let administrative staff go out with students?” The words sounded strange coming from his mouth.
Sherry’s eyebrows rose, wondering where he was going with this. “I don’t think there is any rule against it but…”
Kevin didn’t let her finish as he blurted, “Well, I just happen to have some tickets to ‘Love, The Second Time Around’, which is only in town for one more day.” His words came out in one breath as if he was afraid that if he stopped, he wouldn’t get them out.
The play had been sold out since its premiere and tickets were impossible to get. Kevin had to bribe a friend of a friend and spend $500 bucks. It was a risk but he had overheard Sherry talking and knew that she really wanted to see the play. It was a lot of money and yet, if he were successful, the reward would be more than worth the expense.
“Private box, main balcony,” Kevin said, flashing the tickets.
Sherry’s first thought was no. It was very flattering, but he was just a kid; maybe a very handsome one but still a kid. Then again, she hadn’t been out on a date since the divorce and she really wanted to see the play. Suddenly she felt excitement. It’s crazy. She looked at the young man’s handsome face and thought, why not, what would be the harm? “Will you be a gentleman?”
“Of course.” Kevin’s face lit up like a kid at Christmas. Then he watched her face as she continued to think about it. He worried that she might be reconsidering. Before she could say anything he said, “Then it’s a date?”
Sherry felt another little chill go through her. Hell, she was thirty-five years old; she was old enough to be his mother. Still… it might be fun. Her family wanted her to date anyway. I wonder what they would think if they saw me with a teenager? she thought with a devilish smile and almost laughed aloud.
“Pick me up at seven on Wednesday. Here’s my address,” she said and wrote her address on a business card.
Kevin took the card from her hand and hurried out of the office, as if she might change her mind, turning around and smiling as he exited.
The following Wednesday evening, Kevin came downstairs dressed in a suit. His mother was sitting in the living room reading. He made a point to stop in.
“Oh, you’re going out?”
“Yep, got a hot date,” he said with a smile. He thought he saw a little frown on his mother’s face.
“Oh, you don’t know her. She works at the admin office at the school.”
Kathy had been to the admin office several times and didn’t remember seeing any young women working there. “What’s her name?” she asked, looking back down at her magazine as if it was just a casual question.
Kathy thought for a second and then she looked up in shock. She knew who Sherry was. “Kevin, she’s married isn’t she?”
“Divorced,” he said then bent over and kissed his mother before she could say anything else. “Don’t wait up for me.” He hurried out the door, leaving his mother with her mouth open.
Kevin stopped along the way to Sherry’s house and picked up some flowers. Now, he stood nervously waiting for her to answer the door. When she did, his eyes opened wide in delight. She looked gorgeous. She had on a low cut black cocktail dress that was short on her thighs. The dress was so low in the front that if she bent over too far, her breasts would surely fall out. She had a black choker, with an ivory emblem on it, around her neck. Her face was made up perfectly with blue eye shadow and a soft red lipstick highlighting her pretty mouth. She looked almost regal.
“Are those for me?” Sherry said to the stunned young man.
“Uh… uh… yea, uh… I mean…” Kevin said stuttering.
“Thank you,” she said, taking the flowers and rescuing him from his embarrassment. “I’ll put them in water. It’ll just take a second.”
Kevin stared at her tightly covered backside as she walked away from him, her high heels clicking on the tile and hips swaying seductively. He was sure that she was either not wearing panties or had on thong underwear.
When Sherry came back, she took Kevin’s arm and they walked to the car. Kevin let her in, sneaking a glance at her legs as she slid into the passenger seat. The two chatted and got to know one another on the way to the theater.
Kevin found out that Sherry had been married for ten years with no children. She and her husband had never been a good match. Kevin got the impression that she was too demanding for him. Whether she was referring to sixually, he couldn’t be sure. She said that she wasn’t sure if she would ever marry again. Maybe she would just play the field she added and laughed provocatively. Then Kevin told her about his situation and his dislike for his stepfather, but obviously left out his feelings for his mother.
The show was spectacular as expected. However, Kevin spent more time watching Sherry’s breasts then he did watching the show. He loved the way the soft flesh rippled when she laughed, threatening to pop out of her dress.
Sherry was aware of his eyes and was quite complimented that she could excite such a young, good-looking man. She knew that she wasn’t old, but to a teenager, 35 years old was ancient. She also knew that it could never get serious with a young boy but it was nevertheless refreshing and a boost to her ego to have him practically drool over her. Several times, she leaned into him, pressing her large breasts to his arm. The heat from the touch sent electric shocks all the way to her groin. She glanced down several times and was pleased to see that he had an erection. By intermission, Sherry had to go to the ladies room to wipe her saturated six lips.
When the show was over, they stopped at a local teenager’s hangout and got a root beer float, laughing and joking like kids.
Sherry actually felt like a teenager again. She couldn’t remember the last time she had had this much fun or enjoyed the company of a man so much.
When they arrived at Sherry’s house, Kevin walked her to the door, waiting nervously as she unlocked it.
“I had a wonderful time Kevin,” Sherry said, turning around to face him. Then she waited expectantly.
Kevin felt out of his element now. She was so much older and mature. He wasn’t sure she was waiting for him to kiss her or not, so he decided to just go for it. He pulled her to him and pressed his lips to hers. A sigh almost escaped his lips when she melted into his arms. Suddenly, his nervousness was replaced by passion as he felt her breasts press to his chest and her tongue enter his mouth.
Sherry groaned as the young man continued to kiss her. Almost immediately, she could feel excitement growing in his pants. Ah, youth, she thought as she pressed her groin to his. When she felt his hands sliding down her back, she made no move to stop him. It was a little reward for all of his trouble. Soon, however, his hands were gripping her buttocks, pulling her into his now hard penis. It felt quite large to Sherry.
Kevin pressed Sherry up against the door, his lower half pressing into her groin and his tongue deep in her mouth. He could feel her squirming in excitement as his hands slid further down her backside until they reached the end of her dress. Slowly, he moved his hands upward along the silky nylon on her thighs, waiting all the time for her to stop him.
The lady part of Sherry’s brain was telling her to stop the display they were putting on to her nosy neighbors. However, the woman part loved the attention. It had been so long since anyone had treated her so nice. Her own excitement was growing out of control.
The fingers of Kevin’s hands were shaking as he neared the tops of her nylons. Suddenly, he could feel the hot bare flesh above the elastic band. A moan escaped both of their lips as his fingers moved higher to touch the wet flesh of her excited vagina. Kevin’s head was spinning as he realized that she wasn’t wearing panties at all.
In spite of the warnings that her brain was sending out, Sherry spread her legs slightly, allowing Kevin’s fingers to have access to her swollen six lips. She whimpered in excitement when a finger slowly slid into her dripping hole. “Oh God Kevin, we have to stop,” Sherry said breathlessly as she pulled away from the amorous young man. She reached behind her and pulled his hand down, his finger slipping wetly out of her hole. She closed her eyes and took a deep breath. “I think you had better go,” she said and immediately saw the disappointment in his eyes.
Sherry went up on her toes and kissed Kevin’s lips and at the same time, her hand reached for the bulge in his pants.
Kevin was totally shocked as she squeezed him and said, “I’m free Friday night. I think the county fair over in Trenton has started, if you want, you can to take me.”
“Uh… uh… yea, great,” he stuttered like a schoolboy.
“Seven again?” she asked, her pretty eyes sparkling with mischief.
“Uh… yea… seven is fine.”
“Good night sweetie,” Sherry said, kissing him again and then turned and went into the house.
Kevin stood on the porch for several minutes trying to get his bearings. His plan had been to try to make his mother jealous by going out with an older woman. He was hoping to put on a show for his mother but never considered that he could get lucky. Now, he wasn’t at all sure who was seducing whom.