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Best Laid Plans

Chapter One

Photo by zelle duda on Unsplash

Eighth period had just completed at the high school in the picturesque, Norman Rockwell appearing town nestled in the Finger Lakes of Upstate New York. Students, particularly the senior class, were anxious at the warmer weather of spring time and what it signified: The end. The young adults had a difficult time thinking about anything other than impending changes in their lives where new chapters included dreams of college and freedom.

Richie was more serious than his classmates, yet he could not deny a surge of excitement. He hoped to move away from his parochial home to attend school and take in the rarified air of higher education. Richie’s fantasies included Socratic discussions on “the quad” or sitting in a circle on neatly trimmed grass debating the influence of language on perception. Mostly, he wanted the respect he felt was lacking from his fellow high school classmates. Richie did not have the highest grades because he did not work hard enough on classes that did not interest him. Even Richie admitted he was distracted student, but managed to rise to academic occasion when he felt inspired. Teachers could definitely tell he was a thoughtful young man, but bemoaned his lack of consistency. Richie longed for a renaissance approach to education in that he wanted to excel at everything, but he didn’t want to work hard on less interesting subjects. That did not stop him for wanting his classmates to be in awe of his accomplishments in music, math, science, and art.

Jimmy, on the other hand, was gregarious. He realized he had limited talents and if he excelled it was because he was likable. His outgoing demeanor allowed him to talk to anyone and everyone seemed to like him. Jimmy lived a few doors down from where Richie lived. Although they knew each other vaguely in grammar school, they became friends in high school since they sat next to each other in many classes. The thing that got to Richie was that Jimmy was popular with girls. While Richie was quiet, Jimmy was the life of the party. While Richie was still learning how to present himself, Jimmy always looked like one of those models in a catalog, talking to fellow classmates, rakishly leaning on a lacrosse stick. Richie felt girls should want him for his mind and if they didn’t, then they must be frivolous and unworthy of his attention. While Jimmy was not particular in his attention to girls, Richie was exacting in his appreciation of girls. Jimmy was not discerning and Richie was too particular. Consequently, Jimmy was popular with girls and Richie was perceived as a loner.

As Richie left the school building, he could see Jimmy. Richie approached Jimmy and, as he got closer, Richie realized Jimmy was talking to Linda. He could not help but notice how physically close Jimmy was talking to Linda. Their closeness embarrassed Richie, but it was too late to walk away.

Linda was an attractive girl, popular mostly due to her cheerleading. It seemed she was always on display. Of course Richie noticed her but he noticed a lot of guys checking her out, talking to her much like Jimmy was talking to her now. Nothing seemed difficult for her. Although Richie admired her looks, he was also a little jealous that life looked easy for people like Linda and Jimmy.

“Here’s my man, Richie!” Jimmy said, almost as an announcement.

“Hey Richie,” Linda said, a bit demurely. “Are you going to the prom Richie?”

“Of course, he’s going to the prom,” Jimmy interjected.

Actually, Richie had not given it much thought. It might have been the only thing he hadn’t thought about very much. Proms seemed like an alien world to Richie. Richie’s mom, a widow raising a son by herself, never broached the subject of girls, dating, or God forbid, sex. Richie’s mom could tell he was becoming more interested in girls, but Richie was too embarrassed to talk to his mom about it.

“I hadn’t thought about it.”

“What? Of course, you’re going. Linda and I are going together,” Jimmy said.

“Oh. That’s great,” Richie thought, of course they were going to the prom together. It made perfect sense.

“You should ask Barbara to the prom Richie,” Linda said. “She talks about you.”

“She does?” Richie was incredulous. He had seen Linda and Barbara having lunch together all the time. If Richie put any thought into it, he would have realized Barbara was also attractive. Maybe not in the same way as Linda. Barbara was always an audience to the stage that Linda occupied. Barbara was shy and blushed easily. Barbara, like Richie, was being raised by a single parent, her mother. But Richie was aware that Barbara’s parents were divorced. Ha had also heard that Barbara’s mother developed a drinking habit after the divorce. Richie considered Barbara and concluded that she was worthy of his attention.

“Well, maybe I’ll ask Barbara to the prom.”

“Excellent Richie! Let’s go in on a limo and the four of us can ride together.”

Linda gave Richie Barbara’s phone number. On the walk home, Richie rehearsed in his mind how his conversation with Barbara would play out. He called her before his mom got home from work.

“May I speak to Barbara?”

“This is Barbara.” Of course it was Barbara. Richie felt stupid already.

“Hi Barbara. This is Richie. From school?”

“Oh.” She paused. “Hi,” she said. This was not going well.

“I was wondering if you were going to the prom.”

“I’d like to go. No one has asked me yet.”

She’s not making this easy, Richie thought.

“Would you like to go to the prom with me?” Just as Richie finished asking the question, his mother came in the door. Barbara could hear a door opening and what sounded like paper bags being placed on a table.

“Richie, can you put the groceries away? Oh. I didn’t know you were on the phone,” his mom said.

In a hushed tone into the phone, “I gotta go. I’ll talk to you at school tomorrow?”

“I’ll go to the prom with you Richie.”

“Really?” Richie looked around and saw that his mother was staring at him oddly. “Great! I’ll see you tomorrow, okay?”

“Yeah. See you tomorrow.”

Richie hung up the phone, turned around and saw that his mother had not moved.

“What was that all about?”

“I’m taking Barbara to the prom.”

“The prom? Oh. I didn’t realize you were thinking of going. Who’s Barbara?”

“Someone from school.”

“I figured that” she said as she removed groceries from the bags. Richie kept quiet as he put the groceries away.

Since his father passed away, Richie kept a lot of thoughts to himself. He could tell his mother was hurting and he felt helpless. He wanted to console her but didn’t know how. He talked at length to his mother about his hopes for college but he always felt the subject of girls was off limits. Girls meant sex and his mother no longer had sex. He felt that bringing up the subject would sadden her and he wanted to protect her. He thought about the prom all the time now that Barbara agreed to go. Richie imagined scenarios that made him shiver.

On the night of the prom, Richie walked over to Jimmy’s house. He carried a corsage in a clear plastic container. Jimmy felt a little self-conscious dressed in a tuxedo, walking down the street. Going up to Jimmy’s door, Richie could see the limousine coming up the street. Before he could reach the door, the door opened and Richie sensed a flurry of activity inside. Flashes of light occurred as Jimmy’s family took photographs. Only then did Richie realize that his mother had not taken his photograph. She didn’t say anything like “have a good time”. Her only parting words were, “Be a good boy.” But Richie was tired of being a good boy. He was pent up. Richie wanted to let go badly.

“Let’s get out of here.” Jimmy rushed past Richie. “I don’t want it to look like we’re taking each other to the prom.”

Good point, Richie thought. Jimmy went over the route with the driver and he seemed well aware of the itinerary. As they went to pick up Linda, Jimmy opened his tuxedo jacket and showed Richie a pint bottle of whiskey inside his jacket.

“Where’d you get that?” asked Richie.

“Never mind.” Jimmy punched Richie in the shoulder in a friendly manner. “We’re gonna have a good time tonight, right?” Jimmy said.

“Yeah,” Richie said. He was thinking that he hoped so.

As Jimmy and Linda left Linda’s house, Richie could see the two of them a bit wide-eyed. He wasn’t sure if they were glad to leave her house or were anxious about the upcoming night. Feeling a little nervous, Richie drank a bit of whiskey from the bottle Jimmy left behind in the limousine. Then Richie realized the driver saw him. Richie nervously hid the bottle.

“Don’t worry about it, sonny. Just don’t get obnoxious and, whatever you do, if any of you feel like you’re gonna be sick, let me know right away. I’ll pull over. Just don’t get sick in the car.”

This guy seems to know what he was doing, Richie thought. As Jimmy helped Linda get into the car, the driver raised the privacy window. The limousine had a traditional back seat, that Jimmy and Linda quickly occupied and a bench row along one side of the interior. As they rode to pick up Barbara, Jimmy, Linda and Richie looked at each other marveling at the experience. They were all thinking the same thing: this is our senior prom!

Before Richie could get to Barbara’s door, the front door opened and Barbara walked hurriedly away from the house. Richie could see a flash for a photograph but Barbara just wanted to get away. The front door opened a bit wider and Barbara’s mother poked her head out.

“See that you don’t knock her up,” Barbara’s mom said. Richie turned and followed Barbara to the limousine.

The prom was held in a stately old hotel in downtown Syracuse, New York. The grandeur of the old hotel was the perfect setting for the occasion. Some couples seemed happy. Others seemed like it was almost a solemn occasion. It dawned on Richie that for the serious couples, this was a passage to adulthood. Perhaps he should take this more seriously. Was this a prelude to serious endeavors like college and marriage? He wondered about Barbara’s expectations but tried to keep everything light.

The conversation at their table was peppered with innuendo and good humor. Jimmy, as usual, was like a grand master of conversation, not allowing the conversation to lull and drawing out the quiet ones, like Richie and Barbara. For once, Richie was grateful for Jimmy’s presence.

After dinner the awkward dancing commenced. You could tell some had dance lessons but it was mostly a combination of freestyle cutting loose and couples hanging onto each other during the slow songs. Even Richie and Barbara danced. Richie wasn’t sure where to start but Barbara pulled him close and it reassured him that this unique experience was going to be okay. Barbara’s perfume was a little strong but he liked it. He especially liked holding her in his arms and feeling her warmth and her supple body. Her hands on him was a new experience as well. They fell into a trance studying each other in time to the music.

“Let’s get out of here,” Jimmy interrupted. Richie regretted Jimmy’s intrusion. Richie and Barbara looked at each other and shrugged their deference to Jimmy.

Once in the limousine, Jimmy started to speak to the driver. But the driver interrupted.

“Once around Seneca Lake and then back home. Sounds good to you?”


The driver then raised the privacy divider.

Jimmy put the radio on and passed the whiskey bottle around. Barbara took a gulp and it looked like she was going to spit out. Jimmy and Linda laughed. Richie was concerned, thinking of the driver’s earlier admonition.

“I’m okay,” she said.

“Just take a little bit at a time,” Linda told Barbara.

“Oh, I think I’ve had enough,” Barbara said. Everyone laughed. Linda and Jimmy had a sip, set aside the bottle and went into each other’s arms and kissed. Richie was taken aback by their casualness. It looked like they had done this many times before. He felt he had to follow Jimmy’s example and before he could approach Barbara, Barbara was in his arms kissing him. Richie had kissed his cousin, Stephanie. In fact, they made out but it was just to see what it was all about. Richie did not get too excited since it was Stephanie. But this was something entirely different. Richie felt engulfed by her warm parting lips and her probing tongue. He pressed his lips against hers and he was lost in a pool of exploratory desire.

Coming up for air, Richie and Barbara stopped kissing for a moment to look into each other’s eyes. It would have been a romantic moment except they could not help noticing Jimmy and Linda. Jimmy kissed the front of Linda’s neck until his face was wedged between her breasts. One hand was behind her and the other was trying to reach up under her long dress.

Richie went back to kissing Barbara. He didn’t really care what Jimmy was doing. It wasn’t a competition. Linda and Jimmy were already a couple, he realized. Richie went back to what he liked and that was kissing Barbara. Richie and Barbara kissed and their kisses became more impassioned. Barbara leaned back, breaking their kiss, and held one of Richie’s hands. Trance-like, he watched her place his hand on her bosom. Richie felt the contours and marveled at the curves. He cupped her breasts and gave them a slight squeeze. Barbara moaned as she felt Richie’s hands on her. It felt so good to her and so different from her own hands. His caresses and squeezes were unexpected and she sensed his desire. She liked that. She wanted to encourage him but was unsure of the consequences.

“Oh yes. Oh yes, yes.” They heard Linda’s cries of pleasure and looked over. They could not see Jimmy’s hand since it was up under Linda’s long dress. Jimmy was kissing the side of her neck as he worked his fingers against her pussy. “Don’t stop. Don’t stop,” Linda murmured until she stiffened and screamed. “Oh God, yes! Yes! Oh!” Richie thought his eyes were going to pop out of his head. He had never seen anyone have an orgasm and this was both shocking and exciting to him. Barbara straddled Richie to bring the focus back onto them. With her long prom dress draped over their legs, Barbara leaned into Richie until she could feel Richie’s hard cock against her damp pussy. Barbara leaned down to kiss Richie as she rubbed her pussy against his hardness. Richie worked his hands underneath Barbara’s prom dress, feeling her legs and then, cupping her ass in his hands. He wanted to touch her everywhere. Barbara began to moan and Richie could feel the moisture between her legs.

“Mmmm… that’s so good,” Richie and Barbara heard Jimmy say. They look over and they saw Linda next to Jimmy, and Jimmy’s hard cock is full exposed. They watched silently as Linda took Jimmy in her mouth and sucked his cock up and down. Both Richie and Barbara are shocked. Barbara had never seen a hard cock before and it seemed like Linda knew what she was doing. Richie never had a desire to see someone else’s cock, but watching Linda got him even more turned on. Barbara got off Richie and sat next him. Barbara lifted her dress and showed Richie her wet panties. Richie was so excited, he immediately reached for the gap between her legs and touched her pussy through her panties. Barbara cried out as she felt his fingers against her. Barbara reached underneath Richie’s arm and rubbed his cock up and down through his pants.

“Oooh. Yeah. Yeah. I’m going to cum,” they heard Jimmy say. Richie looked over as Linda moved her head up and down quickly, and Jimmy gasped as his cock squirted into Linda’s mouth. Some of his cum escaped the sides of Linda’s mouth and dripped down Jimmy’s cock.

“Not so rough, Richie. Yeah, like that,” Barbara whispered. Richie couldn’t stop. If he was rough it was because he was inexperienced and overheated. His eyes took her in, the light through the moonroof softly illuminating her reclining body and watched as she began to quiver all over until she cried out in her release. “OH! OH!” This was a wonderment for Richie and he grunted as he shot his cum inside his pants.

On the walk from Jimmy’s house, Richie couldn’t stop thinking about the night’s events. And he was also hoping his mother wasn’t awake so he wouldn’t have to hide the damp stain in the front of his trousers.


Photo by Asif Aman on Unsplash

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