Dan's Story

Once again my thanks go to alphabetacajun for his editing expertise.

Please note that all characters in this story who are engaging in sexual activities are eighteen years of age or older.

The week before prom, Madeline did not let Dan touch her at all, except for kissing. On Thursday right after school Sheila took her out but wouldn't tell Dan what they were doing. They came back with several bags that Sheila took upstairs. Frank was still out of town, so on Friday Dan and Madeline watched a movie after dinner. Every time Dan would start to run his hand up Madeline's leg she slapped it away, telling him he had to wait until after prom.

"You aren't the only one who is horny, Dan," she told him as they held hands during the movie. "I'm used to Mr. Scanlin making me cum several times when I'm with him, and I haven't even seen him since last Friday. Plus, he has been having me send him short videos all week of me playing with my wet pussy but not cumming."

"I didn't know that!" Dan's already hard cock throbbed at the thought of Madeline sending Frank dirty videos.

"I've been sending him pics for weeks, but just started sending videos. He really likes seeing me naked."

"I want to see you naked, too." Dan tried to keep his voice from sounding whiny, but didn't succeed very well.

"Tomorrow is the big day! I promise I will let you see me naked a lot after tomorrow night." She curled against him and patted his cock through his pants. "I can't wait!"

"Me either!" Dan agreed.

"And just so you know, I've been on birth control since I was 16, so you don't need to worry about condoms." Madeline lowered her voice. "I can't wait to have my pussy filled with cum!"

On Saturday, Sheila had arranged for Madeline to go to the spa early for a complete makeover. While Madeline was being spoiled, Sheila and Donna went out for lunch and drinks. Dan got a haircut at 10 AM, then was free until their dinner reservations at 6 PM. He had already been told that he had to stay in his room or the game room until he was summoned, so after lunch he sat in his game room talking to his friends via text. He found out that three of them had decided to go to the prom, and when they asked if Madeline was serious about slow dancing with them, he told them he was sure she was.

At 4:30 PM he was dressed, his dad having come in a few minutes earlier to help him tie his bow tie. The two walked into the foyer, and when Madeline walked down the stairs both of them gasped. Her hair was a mass of loose curls flowing down her back, and her makeup was flawless, her hazel eyes shining out from smoky eye shadow, and her lips coated in dark red lipstick. Her dress was a burgundy halter style with a wide, plunging cleavage that showed off the firm inner slopes of her breasts. The dress reached almost to the floor, with slits up both sides all the way to her waist, showing off her slim, muscular legs with each step. She had high heeled platform sandals with straps that wrapped up her calves.

"Wow!" Richard spoke first. "You look beautiful, Madeline!"

"Yeah!" Dan smiled at her as she stepped up to him. "You look amazing!"

Madeline blushed, smiling as her mom pinned her corsage on her dress, while Sheila pinned on Dan's boutonniere. The couple posed for pictures, then Richard opened the front door. When Dan stepped out with Madeline on his arm he saw Frank's sleek black SUV, with Frank in a black suit standing next to the open back door.

"My, my, don't you two make a charming couple!" He smiled at both of them, "I have the honor of chauffeuring the best looking couple in the school."

Richard was taking Donna and Sheila to a restaurant near the one where Dan and Madeline had reservations. Frank would drop off the couple, then join the parents for dinner. He would pick them up after dinner and take them to the hotel where the prom was being held. Since their suite was in the same hotel, they wouldn't need a ride home until Sunday afternoon. Several classmates were planning to meet in the hotel restaurant for brunch at 11 AM Sunday morning.

They had just left Dan's house when Frank looked in the rear view mirror at Madeline, who was sitting in the middle of the back seat. "Have you missed me this week, Madeline?"

"Yes," she answered quietly.

"Tell me what you missed."

Dan hand was in Madeline's lap, with their fingers entwined. He felt her squeeze his fingers before she answered. "I missed kissing you."

"Is that all?"

When Madeline shook her head, Frank urged her on. "What else did you miss? I'm sure Dan wants to know. Don't you, Dan?"

Dan looked over at Madeline, then nodded his head.

"I missed dressing up for you, and hearing you tell me how sexy I am." She was looking at Frank in the rear view mirror. "I missed feeling your strong hands on me, rubbing my pussy and making me cum so good. And I really missed getting to play with your big cock. I like feeling it in my hands, and in my mouth. I miss tasting your cum."

"I promise I will make you cum soon, OK babygirl?"

"OK! Thank you, Mr. Scanlin."

Dan's cock was drooling in his underwear as he listened to his girlfriend and Mr. Scanlin. The SUV stopped, and he realized they were at the restaurant. Frank got out and opened Madeline's door, holding out his hand to help her down. Dan got out and walked around to the other side. When he turned the corner he saw Madeline hugging Frank, and Frank leaning down to give her a kiss on the cheek and whisper something in her ear.

"I'll be back in two hours to take you to the prom. You kids enjoy your dinner!" Frank shook Dan's hand and then left to join the parents for dinner.

As they sat across from each other at dinner Dan couldn't believe how sexy Madeline looked. He couldn't help but think about the filthy things his girlfriend had just said to Frank. He knew that if it weren't for Frank, the two teens would not be in this position. Knowing Frank had done everything sexually with his girlfriend before him humiliated him, but it also turned him on knowing that Madeline loved it so much.

Edging for Mr. Scanlin all week had Madeline so horny she could barely sit still. The dress she had on showed her legs up to her waist every time she walked, and the top was so open and low cut that the inside slopes of her boobs were exposed, even the lower curve of her perky tits were visible. Knowing what she had planned for after the prom had her pussy throbbing. She was having fun with Dan. He and his friends were fun to be around, and they had made her move to Billington much less lonely. When she had first met Mr. Scanlin, she got a feeling in her belly that she had never felt before. He never pushed her, but it didn't take long for her to ask him to teach her all about sex.

Their dinner flew by, and soon the young couple was back in Frank's SUV heading to the prom. It was being held in the ballroom at the biggest hotel in the city. Madeline could see Frank's eyes in the mirror, and knew he was staring at her almost bare tits. She could feel the wetness on her pussy lips. Frank stopped the car at the back of the parking lot. It was dark, but they could see the line of cars and limos dropping off their fellow students at the entrance. Madeline didn't wait to be asked. She stood and leaned over the console just as Frank turned his head. She covered his mouth with hers, moaning as she tasted his lips for the first time in a week. Dan was watching from his seat, and he saw that leaned over as she was, Madeline's dress fell away from her chest, completely exposing her firm tits. Frank's hand reached up and he grabbed one of her tits, squeezing it as Madeline's moan turned into a loud sigh as they finally broke their kiss.

"I better drop you kids off. If your girlfriend kisses me again like that I will be tempted to pull her into my lap, and I'd hate to ruin that pretty dress before you get to show it off!" Frank half laughed as he gave Madeline's nipple a final squeeze, then slowly drove toward the entrance as Madeline sat back down and adjusted her dress.

Madeline leaned over and kissed Dan. "Did you like that?" she whispered as she brushed her hand across his lap.

Dan nodded, "I love how sexy you are."

Madeline touched up her lipstick just as they reached the entrance. "Thank you for driving us, Mr. Scanlin. I promise I'll wear this lipstick again so you can rub it off with your cock."

Frank laughed and looked at her in the mirror. "I'll hold you to that! Enjoy your prom, and your after prom."

"Thank you, Mr. Scanlin!" Dan called out as he got out of the car and helped Madeline down.

The prom was a blast. Everyone loved Madeline's dress, with multiple guys and several girls staring as she walked in on Dan's arm. Trevor, Nate, and Zander had a table so they joined them. Nate and Zander wore tuxes, while Trevor was sporting a throwback suit complete with a ruffled shirt and big bow tie. They talked and had some punch as the music started up and the dance floor got busy. There was a table of girls next to theirs, and Madeline noticed one goth girl looking over at Trevor.

"Trevor, you should ask Nina to dance with you. She keeps looking at you!" Madeline told him. Just then a slow song started and she took Trevor's hand, leading him to the dance floor.

"Do you really think Nina would dance with me?" Trevor asked as Madeline pressed against him.

"Yes! You are cute, and your suit is super cool." Madeline encouraged him. "She's into art, too, like you, so you'd have something to talk about."

"I guess so." Trevor agreed.

"She's here to have fun just like us." Madeline continued. "I'll make you a deal. If you get her to slow dance with you, I will give you a blow job next week."

"What?!" Trevor looked at her, suddenly aware of his hand on her bare back, and the sight of her perky tits practically falling out of her dress. "What would Dan say about that?"

"I'm Dan's girlfriend, not his property. Besides," she grinned at him, "he really likes me being a little dirty, in case you couldn't tell."

Madeline made similar deals with Nate and Zander, prompting all three to step out of their comfort zone and talk to the single girls at various tables. Nate and Zander ended up dancing with more than one, and they all joined in for the line dances. After working up the nerve to talk to Nina, Trevor spent most of the evening talking and dancing with the cute goth girl.

Dan and Madeline were slow dancing a couple of hours later. All three of his friends were also on the floor dancing with girls.

"I can't believe the guys got up the nerve to ask girls to dance," Dan smiled at Madeline. "Maybe your D&D campaign worked to get them out of their shell."

"I'm sure that helped," Madeline smiled at Dan, "but I thought they were still a little shy, so I added a little more incentive."

"Oh, really?" Dan saw Madeline bite her lower lip as she nodded. "What kind of incentive?"

"I told each of them if they got a girl to slow dance with them that I would give them a blow job." Madeline leaned in and whispered into Dan's ear. "It looks like your girlfriend is going to be busy next week."

Dan's cock had been half hard all night from being teased all week, then hearing Madeline and Frank talking on the way to the prom, and Madeline's sexy dress. Hearing her say she was going to give each of his best friends a blow job had his cock aching.

"Really?" Dan was so shocked, and horny, that he was tongue tied.

"I didn't think you would mind. You liked them seeing me practically naked, didn't you? And I've been sucking Mr. Scanlin's fat cock for a while now." Madeline could feel her pussy getting hotter as she teased her boyfriend. She could feel him shaking as he held her close.

"That's true. I just never imagined you would want to do that. With them, I mean." He stammered out.

"Why not? You said you liked the idea of me being their cum slut. And after tonight I won't be a virgin, so maybe..." She let the idea hang, causing Dan to stop moving. Madeline pulled him close, pressing her firm tits against his chest, "I'll still be your girlfriend, no matter what."

Dan stared, speechless, then the song ended and they walked over to their table. Trevor and Nate talked to Dan, but he was almost in a daze. His girlfriend had just told him she had promised to give his three best friends blow jobs! And then suggested that she may do even more with them. He wanted to be mad, but his cock was so hard it ached. He took a deep breath and shook his head, then reached for Madeline, taking her hand in his and giving it a squeeze. She turned and gave him a smile, leaning up to kiss him. They spent the next half hour talking and laughing with the group around the table.

"Are you ready to go?" She leaned against him. "I'm ready for the real fun to start."

Dan nodded, and ten minutes later they were walking into the enormous honeymoon suite on the twenty-second floor of the hotel. There were LED candles flickering throughout the living area, and there was a winking glow of them coming from the open bedroom door. The second bedroom door was closed. Dan and Madeline stopped at the large leather sofa, kissing passionately as they were finally alone. Madeline pulled Dan onto the sofa, unbuttoning his shirt and pushing it off. Before he knew it he was naked, and Madeline was kissing his chest and neck while her hands roamed down his belly to find his four inch cock hard and drooling. She still had her dress on, but Dan had put his hand inside the top, sliding the material over to free one of her tits. She paused her kissing, leaning back slightly, but still holding his stiff cock. Dan looked at her, seeing one tit exposed, the nipple jutting out.

"Before we go any further, I want to tell you something." She told him, sitting up straighter and pushing her chest out, letting him see her firm, bare tit.

"OK." Dan nodded, his balls already throbbing from a week of being teased.

"I found your dirty stories and videos on the laptop you gave us," she said quietly.

Dan's eyes went wide. He had never wiped his old laptop when he got his new one. He knew exactly what Madeline had found, and his mouth went dry. Before he could speak, she giggled.

"It's OK, I'm not mad. They were hot, even though they all had a similar theme... All of them about a girlfriend or wife getting fucked by a big cocked man while her boyfriend or husband watched. When Mr. Scanlin started taking me to the living room alone after dinner, I realized it really did turn you on. That first night in the living room with Mr. Scanlin, I saw the picture of your family and just knew that your sister Samantha was Mr. Scanlin's daughter. They look just alike! When I asked him about it the next week, he told me to talk to your mom."

"Oh god," Dan's cock had shriveled to a tiny nub, but Madeline still gripped it between two fingers.

"I thought your mom was going to faint when I asked her, but she told me the truth. She told me the story of how Mr. Scanlin seduced her. It was hot! I got so horny hearing it, and realized it was just like a lot of the stuff you had on your computer. When I asked her if you knew, she couldn't lie, so she told me about your eighteenth birthday."

"Madeline, I'm sorry! I wanted to tell you, but I was afraid you'd never want to see me again." Dan was almost in tears, seeing what should be the best night of his life falling apart.

"I understand, Dan. A few months ago, I would have freaked if I found out you lost your virginity to your mom. But I've changed a lot since then." She took his hand and brought it to her bare tit, then kissed him, her fingers stroking his cock back to life. "I still want to be your girlfriend."

"You do?" They were hugging, Dan's naked body against Madeline in her sexy dress.

"Yes, silly! I've known your dirty little secrets for months, and we've still had lots of fun together. Of course, I let Mr. Scanlin do everything first. He kissed me first; touched me first; I let him cum on me first; and I sucked his cock first. And you love knowing he got me first, didn't you?"

Dan's cock was throbbing again. Hearing Madeline talking about how she had let Mr. Scanlin do those things to her had his heart racing again. "Y-yeah, I do love it. I don't know why, but it really turns me on."

"It turns me on, too. That's why we're here tonight. I want to give you the ultimate turn on." Madeline ran her thumb across Dan's cock head, smearing his precum around the small tip.

"I'm ready to lose my virginity." She stood and shrugged her dress off, letting it puddle to the floor.

Dan stared at his sexy, petite girlfriend. Her 32B tits were firm on her chest, and the dark nipples were rock hard, pointing straight out. Her smooth belly led to a narrow waist and slim hips. She was wearing a tiny pair of panties the color of her dress. The front of it dipped so low that Dan noticed her light brown pubic hair was gone.

"Did you shave?" Dan nodded at her crotch.

"Your mom took me Thursday and I got it waxed. Mr. Scanlin likes smooth pussy."

Dan gulped when he heard her say why her virgin pussy was now bald.

"I'm going to our bedroom. You have a choice. You can follow me and take my virginity with your little dick. Or..." She pointed to the closed bedroom door, "you can knock on that door to let Frank Scanlin know you want to watch him have me first. After he shoves his long, fat cock into my tiny pussy, I promise you will get very sloppy seconds."

"He's here?!" Dan gasped as he looked at the closed door, then back at Madeline.

Madeline simply smiled at him then turned and walked into the open door of their bedroom. Dan stared at her cute ass, the tiny string of her panties disappearing between the firm cheeks. His mind was racing, still processing everything Madeline had said. He knew almost all of the porn he watched and read evolved around petite girlfriends and wives turning into size queens at the hands of the husbands' rivals or friends. Madeline must have liked them, too. She was always eager for her alone time with Frank Scanlin, and liked telling Dan how horny she got as Frank taught her all about sex. All of these thoughts raced through Dan's head in the time it took Madeline to walk into the bedroom. Even before he stood up from the sofa, Dan knew what his decision would be.

A second after he knocked on the door it was opened by his mom. She was naked, and he couldn't read the look on her face as she patted his cheek. He looked past her and saw Frank sitting on the edge of his bed, equally naked, his thick, nine-inch cock rock hard and shiny with what Dan assumed was his mom's saliva. Frank nodded to Dan, standing and walking toward him.

"There is a chair by the bed for you," Frank gave him a wink. "You do want to watch, don't you?"

Dan nodded, too shaken to speak.

Without another word Frank strode out of the room. Dan and Sheila followed in his wake, and when they walked into the other bedroom Dan saw his girlfriend lying on the bed, her hands idly rubbing her toned belly and up to her hard nipples. Her face lit up when she saw Frank enter the room, then her eyes went to Dan and Sheila.

"You don't mind if they watch, do you?" Frank asked as he climbed on the bed and stretched out next to Madeline. She immediately reached for his cock, her small hand stroking it lightly.

"I don't mind," she said just before Frank leaned over and kissed her, his hand cupping her panty covered pussy causing her to gasp into his mouth.

Dan had never seen his girlfriend kiss Frank Scanlin. It was obvious that Frank was in charge. His mouth devoured hers, and his hand on her pussy had her arching her back and moaning immediately. The thought struck Dan that he had still not seen Madeline's pussy, and the first view he got would be just before it was filled with the thick, long cock of a man forty-four years older than her. He felt his mom's hands on his shoulders as she stood behind his chair.