Dan's Story

Thanks again to alphabetacajun for editing.

Disclaimer: All characters are 18+. This is a work of fiction. Any similarities to persons living or dead, or actual events is purely coincidental.

Tuesday

Dan walked into the kitchen Tuesday morning and saw his mom at the small table drinking her coffee. She was wearing a see through babydoll nightgown, her full tits and pierced nipples on display. Dan's breakfast was on the table next to her, and he sat and took a drink of OJ before digging in.

"Good morning, sweetie!" Sheila greeted her son. "Did you sleep well last night?"

"Yeah." Dan could feel his cock already leaking into his underwear. He had fallen asleep thinking about Madeline sucking and fucking Trevor and woke up thinking about her doing the same with Nate after school.

"Are you looking forward to Nate coming over this afternoon?" Sheila looked at her son and smiled. "It's important for you to like what is happening as much as Madeline. It may be easier for you to understand now, but your father absolutely loves knowing what I do for Frank."

"I think I get it, mom." Dan looked over as he finished his eggs and toast. "I mean, when Madeline was meeting with Mr. Scanlin in the living room I would get so worked up I would have the shakes. I really like that feeling, though, wondering what they were doing, and the sight of her when she came into the room after being with him for an hour or two."

Sheila smiled and patted Dan's arm. "You are so like your father. And it's good that you know it now. Your father knew he was different even before we got married, but until Frank opened our eyes he didn't know what he was missing."

"I gotta go. I'm meeting Madeline and the guys before school." Dan put his dishes in the dishwasher and gave his mom a kiss on the cheek.

"Have a good day at school. See you this afternoon." Sheila called out as he left.

Everyone was waiting at their gathering spot when Dan got to school. Zander had started giving Madeline a ride since she lived in the same neighborhood now. Dan saw them smiling and talking as he walked up. Madeline was standing between Zander and Nate, with Trevor in front of them. Now that the weather was warm, most of the girls were wearing shorts or skirts. Of course, the cheerleaders were the fashion leaders, but Madeline's newfound sexuality, combined with Sheila's sense of style, had the formerly shy girl turning heads with her outfits. Today she was wearing a plaid skirt and over the knee white socks, with a skintight long sleeved shirt that left her belly bare. The outline of her nipples was already apparent through the thin material, and her skirt rode low on her hips, flaring out to mid-thigh. She smiled and waved when she saw Dan, but turned her attention back to Nate as he was talking.

When the bell rang they made their way into the building. Nate and Trevor went toward their class, while Madeline linked arms with Zander and Dan as they headed to theirs.

"Hey babe!" Madeline paused long enough to give Dan a kiss on the cheek.

Dan smiled at his girlfriend, his eyes drawn to the bumps her nipples made in her shirt. "Hey to you! I can see you're already excited for calculus." He teased as he nodded toward her shirt.

Madeline giggled. "I think you know what I'm excited for, and it's definitely not class." She turned toward Dan as they got to their classroom. "I was a little naughty on the way to school." She whispered. "I couldn't resist giving Zander a little rub. He's so long!"

Dan blushed, and looked up at Zander who shook his head and looked away.

At lunch, Madeline sat between Dan and Nate, but spent most of the time talking to Nate with her hand on his thigh. "It's only fair that I act like his girlfriend today." She explained to Dan. "After all, he's the one who gets to cum in me later."

Dan felt his cock throbbing even as his heart hammered in his chest. He was only inches from his girlfriend, but she was acting like she was Nate's even as the four carried on a conversation.

School finally ended, and the four met in the parking lot. "See you at five, Nate." Madeline smiled and waved. "I can't wait!"

As soon as they left the parking lot, Madeline leaned against her door and spread her legs. Dan looked over and saw her lift her skirt, giving Dan a view of her bald pussy.

"Did you go without panties all day?" He asked as he tore his gaze from his girlfriend's puffy pussy and back to the road.

"No, silly." Madeline said as she ran a finger through her wet slit. "Nate and I were bored in History class after lunch, so he dared me to take them off. I did and put them in his pocket as we walked out. I sat in the back of the last class and teased my clit the whole time. I'm sooo horny!"

Thirty minutes after they got to Dan's house Madeline left to talk to Sheila. Dan thought she might not change clothes, since she was wearing a super sexy skirt already, and the shirt showed off her firm tits and nipples. She didn't come back until close to five o'clock, and Dan couldn't help but stare when she walked in the game room.

"I guess I don't have to ask if you like it." Madeline smiled and turned around. "I was texting Nate last night asking him what he wanted me to wear for him, and he said he really liked sexy lingerie."

Madeline was wearing a dark blue babydoll nighty. The material was sheer, with the cups outlined in white lace accenting her firm tits. The top hung down to just above her belly button, revealing a matching sheer g-string that did nothing to hide her swollen pussy. She walked in front of Dan and turned in a slow circle, letting him see her bare ass and toned legs.

"Your dad really liked my outfit." She told him. "But I didn't suck his cock today. We did kiss a little, and I told him I would give him a blow job tomorrow if he wanted. I bet you would love to watch that, wouldn't you?"

Dan could only blush. He was about to reply when he heard voices coming down the hall. His mom walked in wearing a babydoll nighty similar to Madeline's, only her top had underwire holding up her fuller tits, and she had on a pair of high heels.

"Oh, Madeline, you look so cute!" Sheila smiled at her, then turned to Nate. "Is this what you had in mind for her, Nate?"

Nate looked Madeline up and down, then nodded his head. "You look amazing, Madeline!"

"OK, I'll leave you kids alone. Dinner is at six." Sheila winked at Dan as she turned and left.

Madeline and Nate sat on the love seat, where they kissed for a few minutes. Nate was more forward than Trevor, palming her pussy through her panties as they made out. As Madeline told Nate the abbreviated story of hers and Dan's prom night Nate teased her nipples through the see through top. She kept her legs spread, letting Dan see the wet spot in her panties from her excitement. When she finished telling the story Nate looked over at Dan and shook his head.

"I knew you liked kinky porn, dude, but had no idea how seriously into it you are!" Nate turned to Madeline. "Have you always had a thing for old guys?"

Madeline shook her head. "Nope. I never thought of old guys as sexy, but the first time I talked to Mr. Scanlin my pussy got wet, and he didn't even touch me!"

"What about doing stuff with Dan's friends?" Nate slid his hand back down to Madeline's crotch, his hand going inside of her panties to feel her bald pussy for the first time.

Madeline arched her back and squeezed Nate's shoulder. "Hmmmm! That just kinda happened. It started out with our little D&D campaign. Letting you guys see me was a huge turn on, and I found out that Dan loved it, too."

Madeline turned and pulled Nate down for a kiss, then Dan watched her hips begin to shake as Nate's hand in her panties kept moving. When she broke the kiss she turned to Dan.

"Your friend just made me cum." She took Nate's hand from her panties and showed Dan the wetness on his fingers. "I think I'm going to take Nate across the hall and thank him in private."

Dan watched as Nate and Madeline walked hand in hand out of the room. His head was spinning as he sat waiting for them to return. He knew that Madeline was going to give Nate a blowjob and planned on fucking him after dinner. Nate was the most outgoing of his friends, so Dan wasn't surprised that he had asked questions. He was a little shocked that he had boldly played with Madeline's pussy while Dan watched, and that he had made Madeline cum so easily. It was 5:50 PM when Madeline walked back into the room. Her panties were gone, and Dan could see that her pussy lips were puffy and wet. Her nipples were visible through the sheer top, so hard they made points in the thin material. She straddled Dan's lap and grabbed the back of his head in both hands, pushing her lips against his in a wet, open-mouthed kiss. Dan opened his mouth and felt warm cum pouring across his tongue. He swallowed reflexively as Madeline moaned into his mouth as she kissed him.

"Nate cums a lot, Dan!" Madeline breathed into his mouth after she broke the kiss. "I swallowed two big gulps, but wanted to save some for you. He made me cum two more times eating my pussy."

Madeline's lips and tongue continued to tease Dan's lips, his tongue darting out to lick the cum from her chin. She guided Dan's hand to her crotch, where he ran his finger along her slit, feeling her pussy juice oozing out.

"You're soaking wet." He mumbled as they kissed.

"Mmm-hmm. I think Nate's been studying." Madeline giggled. "He wanted to sixty-nine. It felt amazing sucking on his cock while he ate my pussy. And just before I came the second time he put a finger in my ass. I had his cock in my throat, or you would have heard me scream! I couldn't stop cumming from him sucking my clit and fingering my butt!"

Madeline leaned back and grinned down at Dan. "Your mom told me I would love having both holes stuffed, and I think she's right."

Dan looked over at Nate, who had come into the room a moment earlier. Nate smiled and shrugged. "I'll be happy to help you out with that, Madeline."

"I bet you would!" Madeline laughed. "Your cock will probably feel good in my ass, but I want it in my pussy today. We better go eat so we can get back and play some more."

The three walked to the dining room. Nate had his shirt and shorts back on, while Madeline just had on the top of her babydoll. Sheila raised an eyebrow when she noticed Madeline's lack of panties, while Richard openly stared.

"What happened to your panties, dear?" Sheila asked as they all sat.

Nate blushed as Madeline patted his leg and giggled. "Nate got a little excited when we went to the guest room and ripped them when he was taking them off me."

"Well, those things happen." Sheila looked at Nate. "Next time try to be more careful. Sexy panties aren't cheap, you know."

Everyone couldn't help but laugh at Nate's embarrassment. Once they started eating dinner, Dan's dad changed the subject by asking Nate about his post high school plans. Dan was sitting across from Madeline and Nate, watching as Nate's hand went below the table. Madeline caught Dan's eye and bit her lip as Nate's hand moved to her lap. A few minutes later Madeline thanked Sheila for dinner before she and Nate left the room.

"How are you holding up, Dan?" Richard asked. Dan was surprised, as his dad had not given any acknowledgement into his relationship with Madeline.

"I'm OK." Dan answered as he helped his mom clear the table. "I like knowing Madeline is having fun."

"She's definitely enjoying herself." Richard smiled. "And I am sure you are aware that she will most likely always need to get her, um, enjoyment this way."

Dan nodded, knowing what his dad was saying. If he wanted a future with Madeline, it was going to be one in which he would be her cuckold. Richard stood and patted his son on the shoulder as he excused himself.

When Dan got to the game room he didn't hear anything from the guest room. He expected to be waiting for a couple of hours like last night, so he logged in to play an online video game. He immediately had a message pop up and saw that it was from Trevor.

Trevor: "Waiting your turn? ;)"

Dan shook his head at his friend's dig. "Yeah. Just finished dinner. Want to play some Bio?"

Trevor: "Sure."

Dan and Trevor had been playing online for about an hour when he heard the door to the guest room open. He turned and saw Madeline walk in and approach him. She was still wearing her top, although it had been pulled down to expose both of her perky breasts.

"H-hang on, Trevor." Dan stuttered out as Madeline stopped in front of him.

She gave him a big smile and leaned in, putting her mouth inches from Dan's with his mic in between them. "Trevor?" At Dan's nod she continued. "Nate is OK with you watching us fuck, Dan. I think he likes being watched almost as much as me!"

Dan heard Trevor in his headset. "I heard, dude! You go watch live porn. I'll see you tomorrow."

Dan blushed and took off his headset. "Trevor heard you. Are you sure Nate's OK with it?"

"I'm positive." Madeline closed the gap and licked across Dan's lips, letting him taste Nate's precum. "I think he would have agreed even if I hadn't told him he could be the first to fuck my ass."

Dan groaned at Madeline's words, then stood up when she tugged on his arm. She pushed his shirt up, and he lifted his arms to let her take it off, followed by his shorts and underwear. When he was naked she reached down and patted his hard cock. "Do you think you'll cum watching me get fucked by your friend?"

"I don't know." Dan whispered as they stopped at the guest room door.

"Don't touch yourself, OK?" Madeline. "If you can keep from cumming you'll get to add your cum to Nate's in my pussy when he's finished with me."

Dan let Madeline lead him into the room. It was dimly lit by a lamp on the side table. Nate was sitting on the futon naked, stroking his cock as he watched the two approach. Nate couldn't believe that Dan actually liked watching his girlfriend fuck other guys, but he wasn't going to complain. Nate had always been a bit of a showoff, so letting Dan watch was no big deal. He felt his cock get even harder when he saw Madeline step away from Dan and climb onto the futon. She smiled at him as she crawled over him until her face was above his hard cock, looking into his eyes as she opened her mouth and slowly took his cock in, not stopping until his head popped into her throat and her lips were mashed against his balls.

"Geez, Madeline! Your mouth feels awesome!" Nate looked into Madeline's eyes, then glanced over at Dan, who was standing to the side staring at his girlfriend taking all of Nate's cock down her throat.

Madeline could feel her pussy throbbing as she took Nate's cock down her throat while Dan watched. She had no trouble relaxing her throat for Nate's average sized cock. It was just long enough for the head to pop in. She found she loved the feeling of her throat surrendering to a cock, and while it didn't stretch her the way Mr. Scanlin's did, it felt good popping in and out of her throat. She lifted up and turned around, straddling Nate's lap facing Dan.

"Ready, Dan?" She asked as she held herself over Nate's rock-hard cock.

Dan gulped and nodded. He could see Nate's hand at the base of his cock, holding it away from his belly so that Madeline could line up her pussy mouth with the shiny head. Madeline's pussy lips were already parted from their earlier fucking. Her clit was so tiny he couldn't see it nestled at the top of her slit. Dan felt his own cock pulsing, so small it stuck straight out from his groin. He knew if he touched it he would cum, and knowing that Nate's cock was about to be enveloped by Madeline's hot, wet pussy made his stomach lurch. Madeline shifted slightly, reaching behind her, putting her hand on Nate's chest for balance. This caused her back to arch, giving Dan an even better view of her bald pussy lips kissing the tip of Nate's cock, then slowly spreading as she let herself down, inch after inch of hard cock disappearing until she was sitting on his thighs.

"Mmm, your cock feels good in my pussy, Nate." Madeline leaned back on him completely, turning her head for a kiss.

Dan watched as the two made out while Madeline ground her pussy on Nate's cock. Nate had one hand on Madeline's chest, squeezing and pinching her nipples. The other hand was between her legs, teasing her clit and bringing sighs and hisses from her. Madeline put her hands on her own thighs, pushing them wider.

"Come closer, Dan." Madeline startled Dan, and he glanced up from her spread open crotch to see her looking at him while Nate kissed along her neck and shoulder. "Get on your knees and get close. Nnnn...I'm about to cum again on Nate's cock."

Dan dropped to his knees and shuffled forward, so close he was almost touching Nate's knees. The light was dim, but Dan could easily make out Madeline's shiny wet pussy lips gripping the base of Nate's cock. She was rocking back and forth on Nate's lap, her pussy making soft slurping sounds. Dribbles of juice were trailing out, running down to coat Nate's balls. Nate had his hand at the top of Madeline's slit, using two fingers to hold it open while the other strummed her clit.

"So good, Nate!" Madeline bounced slightly on his lap, her pussy squishing as she moved. "Nnnnnnn!!!"

She jerked and arched her back, and as Dan stared, he saw her pussy start to pulse, her breath hissing out in time with her orgasmic contractions. Nate didn't stop rubbing her clit, and after settling her pussy back fully onto his cock, Madeline glued her mouth to Nate's and began to moan. Her hands dug into her thighs as she kept herself open for him, and as Dan watched her pussy began to pulse with the rhythm of Nate's finger strumming her clit.

Madeline's pussy was already soaking wet from the fucking she and Nate had done earlier, but when she looked down at her boyfriend staring at her pussy filled with Nate's cock, she felt her entire body start to tingle. Losing her virginity to Mr. Scanlin had ignited a streak of exhibitionism that she never knew she had, and getting to fuck Dan's friends in front of him turned her on just as much. She felt Nate's fingers move to her clit, and soon her orgasm slammed through her. She arched and groaned out her pleasure, and when she leaned back to kiss Nate she expected him to take his hand away from her clit. Instead, he slowed his furious rubbing and began to stroke it steadily. Her entire crotch jerked at the sensations rocketing through her over-stimulated nub, but then she felt a hot fire begin to grow in her belly even as her pussy clenched over and over on the hard cock filling her tight channel. She looked down at her boyfriend as she felt her belly twitching with each flick of Nate's finger over her clit.

"Is this what you want to see, Dan?" Madeline's voice was husky as she squirmed on Nate's lap. "I'm going to cum on your friend's cock again. Ohhhh, yessss!"

Dan started to nod as he listened to his girlfriend start to cum. Her body went rigid as she rode out her orgasm. Nate finally moved his hand from her clit and she sagged against him. Dan could see Madeline's clit easily now. Even as small as it was, the tiny nub was glistening, and her pussy lips had swelled as they gripped Nate's cock. Nate started to move, and Dan fell backward, ending up lying across one of the small bean bags. Nate held Madeline by her waist as he guided her to the floor, his cock remaining embedded in her pussy as he went to his knees behind her. Madeline lay her head on her crossed arms, turning her head to look at Dan. With her ass in the air, Nate began to fuck her. After having his cock enveloped in her tight sheath for so long without moving, he was ready to feel his cock sliding in and out. Madeline sighed when she felt his cock sliding almost out of her pussy then shoving back in. She knew this position made her little pussy even tighter. When Mr. Scanlin had fucked her in this position, she felt so full that every time he slammed into her it forced her breath out of her lungs. She loved the feeling of being completely full that Mr. Scanlin's big cock gave her, but now she was realizing that a normal sized cock felt good too.