On Madison's Avenue

Story Info
A long road finally leads Madison to her lover's strong arms.
9.9k words
3.95
24.4k
9
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
LSanders
LSanders
401 Followers

As the cliché goes, when you looked up "nerd" in the dictionary, there was a very good chance of finding Thomas Callahan's picture in the book.

Thomas considered himself a "thinking man's nerd." Sure, he loved science, was gifted at math, and was very proficient with a joystick. But, he also loved adventure and loved stories that swept his imagination away on a magic carpet ride of fair damsels, gallant knights, and dangerous beasts.

Of course, the object of most of his fantasies was not a damsel in distress. It was Madison James. Maddie looked like she fell out of the pages of a magazine. She had long, sleek dark brown hair that tumbled halfway down her back and had the texture and shine of spun silk. Her chocolate eyes were capped with arched eyebrows that made her look as if she always had a secret. Her nose was a razor straight line that divided her high cheekbones and angular face to perfection. Her flawless white teeth were usually easy to spot behind a smile formed by her full, pink lips. Madison's skin was a flawless soft coating of dark butter cream.

Most guys were drawn to her large firm breasts that rose proudly above her chiseled abs. Thomas loved her legs. Madison had the powerful legs of an athlete with well-defined calves and slender ankles. She had competed in gymnastics for several years before the demands of school and cheerleading created too many conflicts. Now, she was the main attraction of the cheerleading squad at Kennedy High.

As an object of fantasy, Madison was at the top of the list of just about every guy at Kennedy. Thomas was certainly not immune to the seductive charm of her eyes or her body, but his real feelings for her began in 8th grade. He noticed that she had been very subdued for a couple of days. They were in Social Studies learning about the old west. Mr. Gregson was recounting the story of Little Big Horn and the atrocities heaped upon the Native Americans.

He had some slides of paintings that depicted many of the characters and the lifestyle of the plains Indians in that era. He put up a slide of a Lakota warrior named, Little Hawk, who was a cousin to Crazy Horse, the leader of the Lakota and Cheyenne warriors that annihilated General Custer's army. When Madison looked up at the screen, she burst into tears. She got up and ran out of the room. Everyone was startled by the outburst. Mr. Gregson knew this was not normal behavior for Madison and sent Teri Elliott to check on her. Maddie was sitting in the hallway outside the classroom crying hard. Teri came back in to tell the teacher, and he went to find out what had upset her.

"Madison, what's wrong," he asked as he sat down beside her and put his arm around her shoulders. She clutched him and buried her head in his chest and bawled for several minutes before finally regaining enough composure to talk.

"It's ... It's ... just that ... the horse in that slide looked ... just like Maza," she stammered between sobs. She explained that she had always fantasized about having a horse of her own, but her family could never afford one. They did agree, however, to take in a horse that had been rescued from an abusive rancher in South Dakota. Those animals had been horribly beaten and starved. Most were so frightened people couldn't get near them.

"Maza, which is the Lakota word for steel, was different. He stared right at that asshole owner ..." she stopped and looked up at Mr. Gregson. "I'm sorry."

He smiled at her, brushed some of the sweaty hair from her face and said soothingly, "Sounds like a pretty good choice of words to me."

She smiled behind her puffy eyes. "Maza stared him right in the eye and never backed down. The rescue people said Maza tried to make the rancher mad at him so the other horses wouldn't ... be hit," she said on the verge of tears again. She swallowed hard. "He became my horse, and he died a couple of days ago, and I miss him so much," she said as she collapsed into tears again. Mr. Gregson just sat and held her for the rest of the period.

When Thomas heard that story, he saw Madison in a different light. Of course, she was still beautiful, but he realized she had even more beauty inside. That was the day Thomas fell in love with the real Madison James.

Thomas had to be satisfied with loving Madison from afar for the next couple of years. They had a few classes, and she was always friendly. But, Madison's world was full of the hottest people, and Thomas was not. It's not that he was homely. He just wasn't a star athlete or class president. Madison was not a serial dater. Once she found someone, she wanted to stick with that guy for awhile. Her current boyfriend was Graham Carter. Graham was class president and a basketball star. They made a good match. Graham was tall and blonde and made a terrific complement to Madison's Mediterranean sultriness.

Of course, high school is high school, and Madison engendered more than her fair share of jealousy. Queen of that group was Allison Hathaway. Allison was actually a pretty girl, but she was also a slut who used her body to get what she wanted from guys.

"Look at Miss Highnmighty," she was often heard saying to her friends, the "Slutettes," about Madison. "We've been watching the princess hold court for four years. I think it's about time Sweet L'il Maddie was brought down to earth."

"How? Graham is totally in love with her. You'll never get near him," said Sally Gaines.

Allison sighed. "You have so much to learn about the power of pussy, Sally."

Graham became her sole focus. She flirted with him. Put herself in situations where she was able to expose skin to him. She flattered him. Nothing worked. Allison was getting P.O.ed. Her opportunity came when she found out about a seniors-only party at Chip Davidson's house on Saturday.

She talked her older sister, Penelope, into getting her the needed supplies.

At the party, she knew Madison and the cheerleaders were going to Tammy's house to change and would be late arriving to the party. She latched onto Graham early in the evening and refused to let him out of her sight. While he was talking to Weston, one of his teammates, she slipped a roofie into his beer. When Graham starting feeling the effects, Allison managed to talk him into helping her find her keys in the upstairs bedroom where the coats were being housed.

Once they entered the room, Graham quickly passed out. Allison struggled but managed to get his clothes off. "Wow! You have a very nice, very long cock, Mr. Carter. I wonder if that's what Maddie sees in you." She took her own clothes off and put Graham's limp penis in her mouth. However, she had no luck getting the unconscious boy hard.

"Hi, Maddie!" Sally yelled from the bottom of the stairs. That was her signal to Allison that Madison had arrived.

"Hi, Sally. Have you seen Graham anywhere?" Madison asked.

"Nope. Oh, wait, I remember him telling Allison he would help her find her keys. They might still be in the bedroom with the coats upstairs," she replied, trying to look innocent. Madison was unsure what the odd expression on Sally's face meant, but she said thanks and headed up to the bedroom.

Allison had to think quickly and hopped on top of Graham and began simulating sex. Madison heard what sounded like moans coming from inside. She opened the door and saw a nude Allison writhing on top of some guy. When she opened the door wider, the light from the hall fell on Graham's face. He had his eyes closed and his head thrown back. Allison looked over her shoulder, saw Madison, and winked. Madison put her hand over her mouth and ran down the stairs and out of the house. Tammy saw her and ran up the stairs to see what had happened. Allison was still continuing her performance and ordered Tammy to give them some privacy.

"You fucking piece of shit!" Tammy yelled at Allison and ran out of the house to find Madison. Graham was hysterical the next day trying to get in touch with Madison. Her dad finally had to tell him to stop calling. He left many tearful messages on Maddie's cell phone, but the damage was done.

In school the next week, stories about the weekend romp were the number one topics of conversation. Thomas had been finishing up a chemistry project and was leaving school late. He stopped in his tracks when he heard voices coming from inside one of the girls' bathrooms and Madison name being mentioned.

"Did you see the look on her face," Allison said with a cruel laugh. "Graham Carter ... Mr. Perfect ... with his long sweet cock crammed up my snatch!" The Slutettes howled.

"But, you said you nothing happened. You never fucked him," Sally said.

Allison looked around the group, rolled her eyes, and sighed. "Sally, it doesn't matter. Madison saw me sitting naked on top of her man. As far as she's concerned, he's tainted goods now. The power of pussy, remember?" The group shrieked with cruel laughter again.

Thomas was angrier than he had ever been. He hurt as much watching Madison as she herself hurt living through the experience. He couldn't believe anyone could be that evil. He vowed to get revenge. He had no idea how, but he was not going to let Allison get away with hurting Maddison.

A couple of weeks later, Thomas' mom had to work on Saturday. She ran one of the biggest family medical clinics in town. She sometimes had to go into work on Saturday to catch up. Whenever she did, she would usually ask Thomas if he wanted to go in and do some filing. She paid him, and he was always happy to help his mom.

Thomas was a familiar face around the clinic, so the few staff members that were there on Saturday were friendly. He had been taught the basics of medical records filing and worked for about five hours. It was about hour number three that fate smiled upon him. He had been putting away records in the "H" section when his eye caught the name "Hathaway." Since no one was around, he pulled out the file and, sure enough, it was Allison's. He kept one eye out for staff and leafed through the folder. It was mostly routine annual physical results, immunizations, etc. But, before long, he hit pay dirt. Allison had to be treated for crab lice on two separate occasions and there was a current prescription for Valtrex. Thomas smiled. He knew Valtrex was used to treat genital herpes.

He nonchalantly took the key pages to the copy machine and stuffed the copies into his pants pocket. Afterwards, he made sure the file was in perfect order and completed his work. Later that night, he got busy on his computer making up a fake flyer, inviting people to a party hosted by one Allison Hathaway. The party would feature a crab buffet and free rides were offered to any male who was brave enough. He noted at the bottom that the party was sponsored by GlaxoSmithKline, makers of Valtrex.

Then, on the reverse side, he attached key passages from the medical records, careful to remove any marks that could identify his mom's clinic. He included evidence of the multiple lice treatments and the Valtrex prescription.

Next day, Thomas rode his bike to a shopping center several miles away from his home neighborhood. He made 1,000 copies of the flyer on pink paper. He then stopped by a florist and got a bunch of flowers and a card. In the card, he put one copy of the flyer and signed it from "A Friend." He dropped the flowers and card on Madison's front stoop.

On Monday, he told his mother he had to get up early for a physics group meeting and got to school just a few minutes after the custodial staff opened the doors and the gates. He snuck through the school and dropped fliers in every student bathroom. By the time homeroom ended, the school was buzzing like a hornet's nest.

Allison was in tears in the Principal's office. The Slutettes were hiding out in shock. Madison and her friends were in hysterics reading the flyer and adding their own rude comments. Thomas leaned against a back wall and took in the majesty of his work. Once again, all was right with the world, he thought.

"Okay, we've got two months until State. How are we going to raise money for transportation?" Tammy Cutler asked. She was the captain of the cheerleaders and was addressing her varsity group who had qualified to compete in the state finals that year.

"Why don't we do what Spring Hill did last year?" Kerrie Larson suggested.

"What did they do?" asked Lori Burns.

"They held a Date-a-Cheerleader raffle. I know it sounds cheesy, but they raised almost $3,000," answered Tammy.

"That's gross," Madison said. "It's like we're just pieces of meat being auctioned off."

"Look, I know this isn't exactly the most sophisticated idea, but it seems to work. Besides, all the dates will be chaperoned," Tammy said. "Let's take a vote." Even though not everyone was happy, they group voted to hold the raffle.

The next couple of weeks, the cheerleaders were busy promoting the event. Posters covered the school, and ads were taken out in the school newspaper.

"Hey, Maddie, wait up!" yelled Blake Nielsen. Blake was the All-American quarterback of the Kennedy Warriors. With Blake's chiseled body, dark features and green eyes, he had his pick of just about any girl in school ... any girl who was not named, Madison James.

"Oh, hi, Blake," she said pleasantly but kept walking. He quickly caught up with her.

"Maddie, my cousin's coming to town over the weekend, and Dad and I are going to take the boat up to the lake to go skiing."

"You should have fun," Madison said coolly.

"No, Maddie, I wanted you to come too," he said moving in front of her and blocking her path.

"Thanks, Blake, but, I'm going to the mall with Tara on Saturday."

"What about Sunday?" Blake asked.

"Going to be with the fam," she said with a shrug.

She started to walk away, but Blake stopped her again. "Maddie, I bought 50 Win-A-Date tickets and put your name on all of them. Is that the only way I can get you to go out with me?"

Madison looked up at those green eyes and smirked. "Fifty, huh?"

"Yeah! I'll buy more if I have to. Look, I know that whole thing with Graham sucked, but we're not all jerks. Come on ... one date ... please?"

"One date ..."

"Yes!" He shouted and jumped into the air.

"Hold on. One date ... Then, if I don't want to go out anymore, you graciously consent to disappear. Agreed?"

Blake shook her hand. "Agreed, but you won't be able to resist me after that, Maddie."

She rolled her eyes and replied, "We'll see. I'm late for Spanish. Goodbye, Blake."

He was still hooting; then he stopped. "Hey, Maddie, when?"

"After the raffle," she yelled in return as she walked into Spanish.

Thomas was leaving nothing to chance. He had saved $650 over the past summer mowing yards. He took $500 and bought Madison James raffle tickets. He then asked his uncle to agree to be a chaperone if he won. He had everything in place. Now, all he had to do was hope Lady Luck would smile on him.

On the last Friday of the month, the students filed into the gym for the big raffle. Thanks, in part to Thomas, Madison alone brought in over $1,000. In all, the cheerleaders cleared $3,250 and were assured of being able to get transportation to the state capital for the competition.

Naturally, Ms. Spears, the cheerleader coach, held Madison's drawing last. All the other cheerleaders were standing to the side with their dates. It was interesting to see how many of the cool people had actually bought tickets.

"Finally, we have the drawing for the date on Saturday with Ms. Madison James," Ms. Spears announced into the microphone. Many boys were on the edges of their seats. Thomas was closing his eyes, silently praying. Ms. Spears stuck her hand into the box marked "James" and finally drew out the winning ticket. "And the winner is ..." She stopped and looked around the gym. "Did I ever tell you about my trip last summer to the Grand Canyon?" she asked with a straight face.

"Come on!" yelled one anxious ticket-holder.

The gym broke up in hysterics. Madison blushed. Ms. Spears chuckled and announced, "The winner is: Thomas Callahan!" There was a small cheer from a group of Thomas' friends, but mostly there was a collective moan.

Blake turned to his friends and laughed. "Man, I feel sorry for her!"

Thomas was in danger of hyperventilating, but he made his way down the bleachers to join Madison and the other winners. Like the others, he took her hand when he was beside her.

"I want to thank you all for your enthusiastic participation!" Ms. Spears yelled. "Congratulations to the winners and 'Go Warriors!'" She then turned to the winners and asked everyone to have a seat for a moment.

When the gym was mostly cleared, she told them the rules. The date was to take place the following Saturday. It didn't matter where each couple decided to go, but ALL of them had to be chaperoned. She gave them all her cell number and passed around a list so the chaperone's name and contact information could be included. She explained that she would be talking to each of chaperone to verify the arrangements.

"So, Thomas, when do you want to get together?" Madison asked with a smile.

Thomas felt like he was going to have a heart attack. "My uncle is going to chaperone us, and he'll pick us up about 6:00 if that's not too early."

"No. That's fine," she replied. Her dimples were amazing he thought. "How should I dress?" she asked.

"Casual. Jeans would be fine," he said.

"I can certainly handle that," she said brightly. Thomas was standing there, not knowing what to say and staring into her dark eyes. "So, I guess I'll see you tomorrow at 6:00," she said stifling a laugh.

"Yeah ... 6:00."

"I may need this between now and then," she said, indicating her hand, which Thomas was still holding. He jumped.

"Oh, sorry!" he replied dropping her hand. She laughed. "You're sweet, Thomas." She kissed him on the cheek and gave him directions to her house. He turned red.

At precisely 6:00 pm, Thomas and his uncle turned into Madison's driveway. Thomas had made sure his uncle was on time. Thomas got out of the pick-up and walked up to the door with a box of sugar cubes. Madison greeted him and introduced him to her Dad. He stuck his head out the front door and waved to Thomas' uncle.

"Well, Thomas, I've never been given a box of sugar cubes on a date," Madison said.

"They may come in handy later," Thomas explained mysteriously. He couldn't wipe the smile off his face.

Mr. James watched the whole thing amused. "Is this supposed to be a metaphor about Maddie being sweet?" he asked Thomas.

"No." Then, he looked startled. "Not that she's not sweet," he quickly explained.

Madison laughed at his awkwardness. It had been a long time since a boy had been this nervous picking her up for a date. She found it charming. Madison took Thomas' arm and headed for the truck with the sugar in her hands. "See you later, Daddy!"

"Have a good time, kids," he said closing the door and shaking his head.

Thomas wanted the date to have a theme and wanted Madison to experience things she didn't expect. Instead of dinner at the mall and a movie, he had something completely different in mind.

Madison made it easy to talk. She led the conversation and even brought Thomas' uncle Bill into it. After about forty-five minutes, they left the highway and turned up a dirt road. "Thomas planned this evening's festivities in meticulous detail, Madison," Bill explained. "We are heading to my place." He smiled.

Madison smiled in a confused way, but she was intrigued that this was not a typical date. After a few bumps and jolts, they turned into the gravel drive that led to the house and the barn. There was a big fenced pen and a handful of horses grazing.

The group was met by Thomas' aunt Terry. Thomas helped Madison out of the truck and introduced her to Terry. She extended her hand. "It's nice to meet you, Madison. Welcome to the Split T Ranch."

LSanders
LSanders
401 Followers