Dan's Story Ch. 05

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.

Dan looked at Madeline as she rested her head on her arms. She caught his eye and crooked her finger at him. He shuffled around until his face was on the floor inches from hers. He could see from the look on her face that she loved the way Nate was fucking her. He could hear the steady 'slap, slap' of Nate's belly hitting Madeline's ass steadily, rocking her back and forth.

"I can't believe I'm Nate's first fuck." Madeline smiled over at Dan. "He's a natural. Oh, yeah, Nate, keep fucking me!" She looked back at Dan's friend as he sped up his strokes.

"Fuck, Madeline! I'm gonna cum!" Nate grunted out, his strokes becoming erratic.

"Cum in my pussy!" Madeline encouraged him. "Give Dan a big load to clean out of me!"

Dan gulped as he heard his girlfriend urging his friend to cum in her pussy. Madeline leaned toward Dan and kissed him, her lips sliding across his from Nate's fucking. She giggled as she tried to keep contact with Dan's mouth. She broke the kiss and smiled at him.

"Isn't this fun!? I love being a cum dump for your friends." She looked down and saw Dan's tiny pecker standing straight up. "I can see you love it, too."

Above them Nate stopped fucking and held himself pressed tightly against Madeline's ass. He felt his balls start to clench as he began to pump his seed into her tight body. When he finally stopped cumming he staggered back onto the futon, flopping onto his back with his slimy cock lying against his thigh. Madeline had closed her eyes when she felt him cumming in her, and as soon as he pulled out she opened her eyes and looked at Dan.

"OK, time to clean me up, sweetie." She gave him a peck on the cheek, then raised up and turned around to face Nate. She reached for his wet cock and lifted it, then turned to Dan. "Slide under me, baby, and eat Nate's cum out of my pussy while I clean him up."

Dan moved around, getting his head between Madeline's thighs. Her pussy was above his face, and he looked up just in time to see a long string of cum fall from her gaping hole onto his cheek. He felt it sliding down to his neck as he stared at his girlfriend's freshly fucked pussy inches above his face. Her pussy lips were bright pink and opened up like a fish's mouth, swollen and hanging down from Nate's cock. He could see the entrance to her pussy, the pink meat coated in pearly white cum that gravity was helping drain out. Another string of Nate's cum appeared, running down one of her outer lips before extending toward Dan's face. He opened his mouth and caught it on his tongue, moaning as he tasted Nate's unique flavor mixed with his girlfriend's pussy juice. Dan could hear Madeline licking and sucking Nate's cock. He glanced up her body to see her holding Nate's entire cock in her mouth just before she settled her pussy onto his face, blocking his view.

Dan's world narrowed to Madeline's sloppy pussy covering his face, and the feel of his cock throbbing helplessly. He heard Madeline and Nate talking, but Madeline's thighs around his head muffled the sound. At one point he heard Nate let out a loud "Holy Fuck, Madeline!" followed by giggling from her. When Madeline raised up off of his face, Dan took deep breaths and looked up, seeing her looking down at him. He noticed that she had her hand stroking Nate's cock, which was hard once again.

"I think Nate wants another turn at my pussy." Madeline grinned down at Dan.

Madeline crawled onto the futon and lay on her back, spreading her legs for Nate. Dan sat up, feeling the mixture of cum and pussy juice that had been smeared on his face starting to cool. He watched as Nate mounted Madeline. She wrapped her arms around his neck and they kissed as he started slowly fucking her. Dan could hear her pussy slurping with each stroke. Nate licked and sucked on Madeline's nipples as she ran her fingers through his hair. He varied his strokes, sometimes going slowly, then slamming hard enough to make their crotches slap loudly. Dan could see Madeline's smile as she gave herself to Nate. He leaned over to whisper in her ear, and Madeline answered quietly, although Dan could hear what she was saying.

Madeline: "It's not really sore, but it's definitely more sensitive. I can tell you've fucked me good already, because my pussy lips and inside is swollen, so I can feel your cock even more."

Nate groaned when Madeline pulled her knees back, opening herself up for him, her feet on his hips. He leaned into her ear again, and she sucked in her breath, then pulled him to her for a long kiss. She glanced over at Dan, knowing he could hear her, before turning and nodding at Nate.

"Yes, Nate, I will be your girlfriend."

Dan's heart fell when he heard his girlfriend tell Nate she would be his. He felt tears prickle his eyes and started to move away when he heard what Madeline said next.

"Dan is my number one boyfriend, of course. He and I share something I don't think I will ever have with anyone else. But I'll be your girlfriend, too. You can fuck me without taking me out on dates. How does that sound?"

Dan didn't hear Nate's response. He felt his cock twitch and had to bite his lip to keep from cumming. He was experiencing a rollercoaster of emotions, going from devastated to euphoric. Even as it registered that Madeline wanted to be his girlfriend, he felt humiliated knowing that she also wanted to be Nate's girlfriend. Dan had a feeling she would be calling herself Trevor's and Zander's girlfriend as well. Dan looked down and saw that his cock was harder than ever, with precum oozing steadily out the tip, evidence that deep down this was exactly what he craved.

Madeline loved to fuck. From the first time Frank Scanlin kissed her months ago, she knew she was going to be the type of girl that would do anything for her lover. Finding out how much it turned Dan on seeing her be another man's slut only made it hotter for her. She was sitting on Dan's face, feeling his tongue flicking along her wet pussy lips as Nate's cum flooded his mouth, while she was licking her own pussy juice off Nate's cock. When she licked down to Nate's balls he let out a low moan. She followed the cum trail lower, and felt Nate pull his knees back. Without thinking, she pushed her face against his balls and ran her tongue across his taint and onto his asshole, bringing a loud "Holy Fuck Madeline!" a second time from his lips. She couldn't help but giggle when she felt his cock start to stiffen in her hand, then she licked his asshole again and again before dragging her tongue back up to his balls, then along his now hard shaft.

Feeling Nate on top of her, slowly feeding his cock into her pussy, had Madeline almost purring. She was aware of Dan watching her from the floor, but concentrated on Nate, loving the feel of his body on hers, and his cock keeping her pussy dripping. When Nate started talking to her, she answered loud enough for Dan to hear, and when Nate asked her if she would be his girlfriend she knew Dan would freak out hearing her answer. Mr. Scanlin had told her many times that Dan was a cuckold like his dad, and secretly wanted to hear how much she loved fucking other men. When she told Nate she would be his girlfriend, she caught Dan's shocked look out of the corner of her eye, and when she said Dan was still her boyfriend she saw Dan start to shake.

Nate started fucking Madeline harder after she told him she would be his girlfriend. He knew she meant it more like a fuck buddy, and he was fine with that. He pushed her legs onto his shoulders and began to drive his cock into her pussy. She grunted under him, her hands gliding along his sides and down to his ass.

"That's it, boyfriend. Give me that cock. Fuck me like my other boyfriend can't." Madeline chanted, feeling Nate's cock sliding along her sensitive channel. "Put another load of cum in me for Dan to eat."

Nate couldn't hold back any longer. Arching his back, he plunged into Madeline's hot pussy one more time, holding himself deep as his balls emptied themselves for the third time that night. After he finished, he flopped beside Madeline, who turned and kissed him.

"I love how you keep getting hard for me." She murmured into his mouth. "I want you to use my holes all summer."

Nate nodded, his chest heaving from the long fuck session. He looked at his watch and jumped up. "Crap! I gotta go! I told mom I'd be home at ten thirty, and it's already twenty after."

Madeline giggled as Nate jumped over her and off the bed. "You better take a quick shower, unless you want your mom to know you've been fucking all night."

"You're right." Nate grabbed his clothes off the floor and looked at the bathroom door. "Dan, can I take a quick shower?"

"Yeah, sure." Dan nodded.

The guys spent the night regularly, so he knew where clean towels were located. As soon as Nate closed the bathroom door behind him Dan heard Madeline clear her throat. He looked over and saw her stretched out on the futon with her legs spread. Her pussy was once again a mess.

"Still hungry?" She smiled at him.

In answer, Dan crawled between her legs and began to lick her gooey slit, bringing fresh moans to her lips.

"I only came once the last time Nate fucked me, so I need a couple more from your sweet mouth." She reached down and ran her fingers through his hair.

They heard the shower stop and a minute later Nate came out, pulling his shirt over his head. He found his shoes and slipped them on, then stopped, looking down at Madeline lying on the futon with Dan between her legs licking her well-fucked pussy.

"Dan really likes your cum, Nate." Madeline giggled. "Dan, you should thank Nate for giving you so much cum to lick up tonight."

Dan blushed listening to Madeline tease him but lifted his head and looked at Nate and mumbled. "Thanks for cumming so much." He ducked his head back down, burying his face in Madeline's crotch to hide his embarrassment. His hard cock was aching, trapped between his belly and the futon.

"Give me a kiss." Madeline told Nate, raising up on one elbow to hug and kiss him. "Thank you for fucking me so good! I'll see you at school tomorrow, boyfriend."

As soon as Nate left the room Madeline grabbed Dan's head and arched up, grinding her wet pussy against his face as she orgasmed. Dan had learned from last night that she could cum several times, so he kept licking and kissing all around her pussy.

"Mmm, you really are good at eating pussy, Dan." She sighed. "I hope you had half as much fun watching as I had fucking Nate!"

Dan looked up at her. "It was fun. You are so sexy. I can't believe he went three times."

"What, you don't think I'm sexy enough to keep a guy hard?" She teased.

"No, I didn't mean it like that!" Dan sputtered. "Just that he came so much the second time, I thought he might be done."

"Well, when I was cleaning him off after that second time, I licked all the way down to his ass, and that got him hard fast." Madeline put her hands behind her knees and rocked back, offering her puckered asshole to Dan. "It felt good when you licked my ass last night. Why don't you lick it really good right now?"

Dan lowered his head and began to lick Madeline's cum covered ass. He heard her moans and pressed his tongue deeper, feeling the tip push past her ring.

"Mmm, that feels good, Dan." Madeline encouraged him. "I know Nate is going to like fucking it."

Dan moaned as he heard his girlfriend talking about giving her last virgin hole to someone else. He cleaned her ass thoroughly, then licked back up to her clit, sucking and licking until she came again.

"OK, that's enough for tonight." Madeline gently pushed Dan's head away from her pussy. "I need to get home."

Dan scooted off the bed and stood up. Madeline sat up and looked at Dan, then covered her mouth and pointed at his dick.

"Oh wow! Dan, your little pee pee is so hard! And almost purple. Does it hurt?" She reached out but didn't touch it.

Dan nodded. His cock had been achingly hard since Madeline had come into the game room in her lingerie hours ago. He looked down and saw a long string of precum hanging from the tip of his little pecker. Madeline reached out and ran one finger from his tight balls, along the underside of his cock, to the drooling slit. Dan's cock bounced and strained at her touch, fresh precum bubbling out the tip. Madeline ran her finger through the clear liquid before putting her finger in her mouth.

"You do taste good." She said after popping her finger out of her mouth. "But I think you should wait until tomorrow to cum. Will you do that for me, Dan? Will you wait until I suck Zander's big cock and let him fuck me before you empty your balls?"

"Ohgod, Madeline. They already hurt! I'm not sure if I can hold off that long." Dan was almost whining, even as his cock twitched and bobbed in front of his girlfriend.

"I edged myself for a week for Mr. Scanlin." She reminded him. "If you are a good boy and hold off, I will let you choose between my mouth or my sloppy pussy to put your cum, OK?"

"OK." Dan moaned again when Madeline gave his cock a pat before standing and giving him a hug. The feel of her smooth belly against his penis almost caused him to lose control.

"Your mom said she would put my clothes in your room." Madeline said. They went into Dan's room and dressed, then walked to the front of the house. The living room was silent, so they went out to Dan's car.

As they drove home Madeline held Dan's hand. "You are OK with me being Nate's girlfriend, aren't you? Trevor didn't ask, but I think he may be hoping that Nina will want to be his girlfriend. If Zander asks me, I'll be his girlfriend, too."

"Really?" Dan was almost dizzy processing the idea of Madeline agreeing to be Nate's and Zander's girlfriend. "But you'll still be my girlfriend, won't you?"

"Of course I'll be your girlfriend, silly!" Madeline squeezed his hand. "With your friends I consider myself more like a mistress. You know, a woman willing to spread her legs any time one of the guys wants to empty his balls."

Dan swallowed and nodded. "Yeah, I understand what you mean." Dan was painfully aware of the dull ache in his own balls, even as his cock lurched back into full hardness listening to his girlfriend talking about spreading her legs for his friends.

When they arrived at Madeline's house she leaned over and gave him a kiss. "Remember, no jerking off tonight thinking about your girlfriend being a slut your best friends."

Wednesday

Dan couldn't concentrate at school on Wednesday. Madeline had started out his day texting him a pic of her with Trevor's cock in her mouth, copying Nate and Zander. When she greeted him with a kiss outside the school he could taste the remnants of Trevor's cum.

"I thought Trevor deserved a blow job for bringing me to school." Madeline whispered into Dan's ear.

Dan nodded and blushed, looking at his cute girlfriend. Madeline was wearing a pair of ripped jean shorts that almost showed her ass, and a button-up short sleeved shirt tied under her perky boobs, with only one button holding it closed. Knowing Zander was going to be fucking his girlfriend after school didn't help his state of mind, especially since Dan's mom had gushed to Madeline about the size of Zander's cock.

The four friends sat around at lunch talking about summer plans, with graduation less than two weeks away. Between family vacations and summer camps they would all be gone at various times. Madeline was starting a part-time job, as was Nate, so their time together as a group would be limited. Madeline was sitting between Nate and Zander, with Trevor and Dan across from them.

"Don't worry." Madeline reassured them. "My job is only during the week, so I'll still have Saturdays open."

Dan saw Madeline's hands moving under the table and was sure she was rubbing Nate's and Zander's cocks. She looked at Dan before adding, "I mean, if you guys still plan on playing D&D at Dan's house this summer before you leave for college."

All of the guys immediately chimed in that they planned on going to Dan's every Saturday throughout the summer and hoped to do some overnight gaming as well. They knew that everyone wouldn't be available every Saturday due to work schedules and vacations.

"Ooooh, that sounds fun!" Madeline giggled. "Will I be invited for the sleepovers?"

She was met with a chorus of "Yes!" "You better believe it!" and "I get to pick your PJs!" from the guys.

"Will your mom let you stay all night?" Dan asked, looking across the table at Madeline.

"I'm pretty sure she will." Madeline giggled. "She hasn't said anything yet, but she's given me some looks when I've come home a few times. Especially on Thursdays, and the two Saturdays your mom and I did our little succubus campaign."

Dan gulped, and the other guys looked at Madeline. Zander chimed in. "If your mom is OK with you staying over it would be awesome! But we don't want you to get in trouble."

"I'll figure it out, don't worry. Oh, I'm not available this Saturday." Madeline told them. "My sister is playing in the state tournament and I'm going with mom to watch her. You guys should come! It's at Stanton College. I'm sure you'd all like watching all the volleyball players in their tiny shorts and tank tops." She teased them.

The guys said they would ask their parents but were sure it would be OK. All of them had family coming in for graduation the next weekend.

"So, we won't get to play, um, D&D for the next two weeks?" Nate looked around the table. "That sucks!"

"No kidding. The last few weeks of D&D have been the best ever!" Trevor waggled his eyebrows at Madeline. Everyone laughed, but then got serious as they discussed getting together again.

Later that afternoon Dan and Madeline were in his game room. They didn't have any homework, so they were playing MarioKart.

"Are you going to change before Zander comes over?" Dan asked, looking over at Madeline's bare legs.

"Nope. Zander said he thought I looked sexy in anything I wore." Madeline looked at Dan. "He's your best friend, isn't he?"

"Yeah." Dan nodded. "When his mom died I hung out at his house a lot. Mom wanted to make sure he wasn't alone. His sister Luna was there some, but it was hard because of their ages."

"How old were they? What happened to his mom?"

"Zander was ten, and Luna was thirteen. Their mom had breast cancer years earlier, but it came back."

"Oh, that's so sad. And Zander's dad never remarried?" Madeline asked.

"No. I was too young at the time to understand a lot of what was going on. Later mom told me that Mr. Simms didn't want to date because he wanted to give Zander and Luna all of his attention."

"Well, Zander is definitely a nice guy." Madeline leaned over and kissed Dan. "I'm glad you two are such good friends." She giggled and ran her hand up his thigh. "Because I plan on letting him fill my pussy up after dinner so you can get a hot, creamy dessert."

"God, Madeline!" Dan couldn't help but smile at how quickly Madeline changed the mood from somber to horny. "You drive me crazy."

Madeline could feel Dan's cock harden under her palm. "I like driving you crazy." She told him. "I like it even more when I get a big cock to play with instead of your little one."

Madeline stood before Dan could reply. She unbuttoned the one button of her shirt, then loosened the knot tying it under her boobs. Her almost C cups looked big on her small frame, and with her shirt gaped open Dan could see the inner slopes of the firm globes.

"I'm going to go talk to your mom for a minute." Madeline told him. "And I'll see what your dad thinks of my outfit."

Dan looked at his watch as Madeline turned and left. It was just after 4:00, so Zander wouldn't be arriving for almost an hour. He switched to single player mode, trying to keep his mind occupied as he waited for Madeline to come back. He knew she liked to talk to his mom about Frank Scanlin and what she had done for him through the years. Dan also knew that Madeline had sucked his dad's cock, even though by her account it was no bigger than his.

Dan heard voices from down the hall and looked at his watch. It was 4:55. He paused his game and went to the back of the room, standing by the chair across from the love seat. He heard Madeline's laugh, then she stepped into the room holding hands with Zander. Dan's eyes went wide. He had seen his girlfriend wearing outfits ranging from modest to slutty. Frank Scanlin had brought out her exhibitionist side, something that fed Dan's perverse need to let others see her body. When she had left earlier, she was wearing shorts and a revealing shirt, along with her favorite black Converse tennis shoes. She was still wearing her shoes and shorts, but her shirt was gone, leaving her lightly tanned upper body completely bare, her firm, pale tits and rock hard nipples on display.

Madeline saw Dan's reaction and gave him a big smile. "Your dad said my shirt didn't hide much, so I decided to take it off." She told him, looking from Dan to Zander.

Madeline leaned against Zander, pressing her naked tits against his arm. "Since I already told Zander about Mr. Scanlin taking my cherry with his big cock, we're going to go across the hall, OK?"

"Y-yeah, sure." Dan managed to get out. Knowing his girlfriend was walking around his house topless gave Dan goosebumps, and being reminded that she had already told him the story of their prom night made him blush.

"Are you sure you're OK with this, Dan?" Zander had one arm around Madeline's waist but was looking at his best friend with concern in his eyes.

Dan took a deep breath. He knew Zander wouldn't do anything with Madeline if he thought that Dan didn't want it. "Yes. I'm very OK with it. Have fun, just don't be late for dinner!" He forced a smile. "Mom made your favorite. Spaghetti."

Zander nodded, then he and Madeline turned and went into the spare bedroom across the hall. Dan got an Izze from the small fridge and went back to his game. He finished a game forty-five minutes later and stood, walking to the back of the room. He hadn't heard anything from across the hall. At 5:55 the door opened and Madeline came out, followed by Zander. Madeline's face was flushed, the redness spreading down her neck to her chest. Her nipples were hard points, and Dan could see that her lips were slightly swollen as she ran her tongue across them. Zander was sweaty also, his hair mussed.

"Let's go eat!" Madeline smiled over at Dan as she held her hand out to him. Leaning in she whispered into his ear. "Don't worry, I'll tell you all about it later."

Dan nodded as she took his hand, holding Zander's with her other, and the three walked to the dining room. When they got to the dining room Dan was not surprised to see his mom topless, showing off her pierced nipples.

"I didn't want Madeline to feel awkward." She grinned at Dan's topless girlfriend. "Although if my tits looked as good as hers I would show them off every chance I got!"

"Your breasts are as sexy as the day I met you." Dan's dad assured her. "Maybe even sexier, with the piercings Frank got you."

"You're sweet, Richard." Sheila smiled across the table at her husband, then looked at Madeline. "But look at Madeline's. Already bigger than mine, and so firm! My pussy is wet just looking at them."

Madeline blushed, but smiled at the attention, knowing that everyone at the table was now staring at her young tits. "Thank you, Mrs. Boykin. I'm wet too, but for another reason."

The two ladies laughed, and Dan saw Zander blush even as he joined in. Dan's dad knew Zander better than any of Dan's other friends, so the conversation around the table was fairly casual. Madeline and Sheila got plenty of looks, and their nipples were hard the entire time. When they were all finished Richard excused himself and went upstairs.

"OK, you two." Sheila motioned to Zander and Madeline, who were next to each other. "I believe you have some unfinished business. Dan will help me clean up."

"Thank you for dinner, Mrs. Boykin." Zander said as he stood.

"Yes, it was delicious!" Madeline agreed. She looked over at Dan. "We're going back to the guest room, so you don't need to hurry."

Dan swallowed and nodded. He helped his mom clean up from dinner, then she had him sit with her. He tried not to stare at his own mom's naked tits, but it wasn't easy, and he knew she caught him glancing down at them.

"Madeline said she was going to tell you about her time with Zander after he leaves." Sheila said as she patted Dan's shoulder. "She said you got to watch her with Nate, though. Did you like that?"

Dan nodded, his cock twitching as he remembered the sight of his girlfriend cumming on Nate's cock over and over.

"She also said you liked licking her messy pussy. I'm glad, because it's important that she knows that you support her decision to let others have her pussy."

"Does dad like yours messy?" Dan whispered, acutely aware of his aching balls as he fidgeted in his seat.

"Oh, yes!" Sheila smiled. "He has learned to love the taste of cum. He has sucked quite a few cocks, too, whether they have just finished fucking me, or to get them hard for my pussy."

Dan looked at his mom, his eyes wide. He didn't realize he was licking his lips until his mom leaned over and kissed him gently. "Don't worry, sweetie, I doubt Madeline will ask you to suck one of your friend's cocks. But one day, don't be surprised if your wife asks you to do it for her."

Dan was trembling. He had several videos of cuckolds sucking the cocks of their wives' bulls, and while he found them revolting they also made him cum the hardest when he masturbated to them.

"I will let you go, sweetie." Sheila stood and pulled Dan to his feet, hugging him to her naked chest and kissing him fully on the lips. "You may have to show me what you've learned about eating pussy soon." She teased him before leaving the room.

Dan walked slowly back to the game room. He could feel his precum soaking into his underwear. As he approached the spare bedroom he noticed that the door wasn't closed all the way. He stopped and looked through the gap. The room was dark except for a lamp at the side of the futon that gave off enough light for Dan to see Madeline and Zander. Madeline had her left foot on the back of the futon, with her right leg sprawled out and hanging off the edge. Zander was between her legs, his ass rising and falling as he fucked into her with slow, deliberate strokes. Dan heard Madeline's voice encouraging her latest lover.

"Yes, Zander. Fuck me deep. God, that feels so good!" Madeline's arms went around Zander's neck and pulled him down for a kiss.

Dan had seen Nate fucking Madeline the day before, but he could tell from the tone of Madeline's voice that Zander was hitting places that had only been touched by Frank Scanlin before now. Madeline had her arms around Zander's neck, her legs spread wide as Zander kept fucking into her. They were kissing and talking, their voices too low for Dan to hear, then Madeline arched against Zander and let out a long moan. She turned her head toward the door and her eyes locked with Dan's. Dan was rooted to the spot, his cock throbbing painfully.

"Ohhh fuuuucckk!" Madeline's eyes never left Dan's as she started to cum. "Don't stop! Your cock is so good, Zander! I love it!!"

Madeline's lower body was shaking and writhing as she came. Zander's ass never stopped rising and falling, and as Dan watched Madeline's orgasm slowed, then with a hiss her crotch began to rise up again, and she pulled Zander into a wet kiss as she began to cum again. Dan watched for a few more minutes, feeling his cock drooling more precum into his underwear. He finally tore himself away from the doorway and stumbled across the hall and into the game room. He collapsed onto the love seat, the urge to take his cock out and jerk off was almost too much to resist. Madeline's promise to let him cum in her mouth or pussy kept him from finishing himself off.

Dan sat and listened to the sounds coming from across the hall. The rhythmic slap-slap of naked bodies was interspersed with loud moans from Madeline. After what seemed like forever, but was probably half an hour, Dan heard a harsh, drawn-out groan from what had to be Zander, then it got quiet. Dan knew that his best friend had just cum inside his girlfriend. He waited for one or both of them to come into the game room, but it remained quiet. He got up and walked to the game room door but stopped before walking across the hall. He could hear soft voices coming from the guest room but couldn't understand them. He stepped closer, staying away from the opening to keep Madeline from seeing him. From there he could hear snippets of Zander's and Madeline's conversation.

"It was much better than Trevor or Nate." Madeline's voice came through, then a giggle. "Oh, god no! Dan's penis is so small I don't consider what he does as fucking."

"Mmmm, Nate told you that? Yes, I'll be your girlfriend, too."

Dan felt his heart pounding, and as humiliated as he was, he could feel his cock pulsing. He was about to turn around when he heard Madeline speak again.

"I can feel you getting hard again... Of course you can fuck me again. Dan will just have to wait."

Dan heard Madeline moan softly, then the unmistakable sound of a hard cock fucking a wet pussy. He hung his head and went back into the game room, slumping on the love seat as he resigned himself to wait until Zander added another load of cum to his girlfriend's pussy.

Almost an hour later Zander stepped into the doorway of the game room. Dan looked up from his phone and saw that his friend was already dressed.

"Hey man." Zander stopped at the doorway. "I'm heading out. Madeline said she's ready for you."

Dan looked up and nodded, not sure how to answer his best friend. He felt like a loser, willingly letting his girlfriend fuck his friends. The worst part was the fact that his dick had been hard the entire time Madeline had been alone with Zander.

"See you tomorrow at school." Zander said as he patted Dan's shoulder as he walked away.

Dan took a deep breath. Wiping his sweaty hands on his shorts, he walked across the hall. The door was open halfway, with the lamp at the futon still the only light in the room. He saw that the futon had been opened into a bed at some point, and Madeline was sprawled in the center, her chest rising and falling. Her legs were spread, and as Dan approached he could see the mess Zander had left. Her pussy lips were swollen, with gobs of cum oozing out. Madeline lifted her head and looked at Dan as his eyes never left her crotch. She ran her hands down her belly and slowly peeled her pussy lips apart, showing Dan her dark pink meat covered in cum.

"I saw you watching Zander fucking me earlier. Do you want to hear what else we did while you were waiting?" She spread her legs further. "Get naked and slide your little cock in my pussy and I'll tell you all the details."

Dan tore his eyes from Madeline's pussy, looking up at her smiling face. He quickly stripped and climbed between her legs, gasping when Madeline caught his cock between her thumb and finger and guided him to her sopping wet cunt. He groaned when he felt his cock sink into her, the heat from her pussy almost making him cum immediately. He gritted his teeth and took a deep breath, trying to hold off. Madeline giggled when she saw her boyfriend struggling to keep from cumming so quickly. She wrapped her legs around his waist, holding his crotch tightly against her slick pussy. She could barely feel his cock in her well-fucked hole.

She pulled his face down and kissed him, letting him taste Zander's cock on her lips and tongue. "Zander has a nice, long cock, Dan. Not quite as long as Mr. Scanlin's, and nowhere near as fat, but it feels amazing. He fucked my throat before dinner. I laid on my back across one of the bean bags, and when he was on his knees he was at the perfect height. God it felt so good! He really liked putting his hand on my neck and feeling his cock head making my throat swell. When he came, he kept his cock stuffed in my throat so deep his balls covered my eyes. I did manage to get him to pull back in time for me to get a few spurts in my mouth so I could taste him."

"Ohshit, Madeline!" Dan moaned out. "I'm so close!"

"I know, baby." Madeline stroked Dan's back. "Try to hold out a little longer."

They lay quietly while Dan struggled to keep from cumming. His cock was not moving, but the heat of Madeline's swampy cunt had him shaking, even though he could barely feel her pussy walls gripping his skinny shaft. When she felt him calm down she continued.

"You saw him fucking me when you peeked at us. He licked my pussy first, then worked himself balls deep. I've told you how Mr. Scanlin's cock is so long it goes into the deepest part of my pussy. Well, Zander's cock goes almost as deep as well, but since it's not as fat as Mr. Scanlin's he can fuck me deep easier, and my god it feels good!" Madeline could feel Dan shaking, and knew he wasn't going to last long. "It's OK if you cum from hearing about your best friend fucking me, Dan. I will tell you the rest while you clean my gooey pussy. Zander put two nice loads there after dinner."

Dan whined into Madeline's neck as he felt his balls explode. He tried to move his hips, but Madeline had her legs locked around his waist holding him in place. His orgasm was over in three spurts. Madeline relaxed her legs, and he slid down, kissing her perky tits and flat belly before his tongue tasted the salty sheen of cum and girl juice above her bald mound.

"Is it as messy as it feels, Dan?" Madeline ran her hands through Dan's hair as he looked up at her.

"Yeah, it's real slimy." Dan was up close with Madeline's pussy now, the smell of cum almost overpowering.

Her outer lips were peeled back, exposing her tiny clit in its hood. Dan was learning what his girlfriend liked, so he flattened his tongue and ran it from the base of her slit up to her clit, collecting wads of cum before closing his mouth and slurping it down noisily.

"Mmmmm, I love how soft your mouth is on my tender cunt, Dan." Madeline sighed. "I'm so glad you're my boyfriend, because not many guys would be willing to eat someone else's cum out of their girlfriend's pussy."

She giggled as she shifted her crotch, guiding Dan's tongue all over her messy cunt. "So, after Zander worked his cock deep inside me, he was able to fuck me with long strokes. You saw him doing that. It felt sooo good! Every time he bottomed out, I felt his head bumping against my cervix and my feet literally jerked. I couldn't help it! At one point he pushed my legs back and I was watching my feet twitch and jerk with every stroke. When he came in me the first time, he laid on top of me and rested. His cock is so long it stayed inside, and as we kissed and talked I was squeezing him with my cunt muscles, and after a few minutes he started getting hard again."

Dan pushed his tongue deep into Madeline's open hole, getting rewarded by a huge glob of Zander's cum. He gulped it down and drew his tongue out, lying flat on the bed and licking between her cheeks to her asshole. Madeline let out a sigh when she felt Dan's tongue slide across her sensitive asshole.

"That feels nice, Dan. If you can get hard again, I will suck your cock for you." She tempted him. "After Zander got hard again I sat on his lap and we made out while I rode his long cock. He liked sucking my nipples, and he even played with my ass a little. I think I came four or five more times while I was riding him. Feeling his cock deep in my cunt as we kissed and talked kept me dripping wet!"

Dan moaned as he listened to Madeline telling him about her time with Zander. He had one hand on his cock as he licked all over her pussy and ass, cleaning the combination of her and Zander's cum from her smooth skin. He finally raised up to his knees, showing Madeline his erect cock.

"Oh, Dan! Your little wee wee is hard again!" She smiled at him. "Come up here and let me suck it."

Dan shuffled around, then let Madeline guide him onto his back. She lay beside him and leaned over, giving his tiny hairless balls a kiss. "Just so you know, I told Zander I wanted to be his girlfriend, too." Madeline's mouth covered Dan's small penis, easily taking him to the root, making him gasp.

"You're OK with me being Nate's and Zander's girlfriend, aren't you?" She had the base of his cock between two fingers, licking the head as she looked up at him. "We all know your cock is useless, although it's cute for the short time it's hard."

"I'm gonna cum!" Dan choked out, his eyes pleading with his girlfriend. Madeline quickly captured his head between her lips and jerked the short shaft with two fingers, her eyes shining as she held his gaze. He felt his balls pulse twice, then a third painful time when Madeline sucked hard. She pulled off and swallowed quickly.

"Your cum is tasty, Dan." She licked her lips. "But I prefer having a big mouthful to swallow. Or a pussy full for you to eat."

She winked at him as she moved around and pulled him into a hug. "This summer is going to be awesome! Between my boyfriends and Mr. Scanlin, I'm going to have all the cock I could ever want!"

This concludes Dan's story... so far. I have other ideas for his time with Madeline as he goes to college, but for now I plan to concentrate on my other stories. If you want more of this timeline let me know in comments or via email.