Sarah's Discoveries - Cover

Sarah's Discoveries

Copyright© 2026 by DangerMouse

Chapter 6: Two-man Challenge

Incest Sex Story: Chapter 6: Two-man Challenge - Sarah (and then one of Sarah's friends) are introduced to a variety of pleasures by Sarah's older brother and one of his friends. It was originally split into four "books" but I have combined them here. This is one of my favorite stories that I got from the early internet (probably even before the web existed in the wild). I couldn't find it online when I looked so I thought I would share it here for others to enjoy. If this is your story, please let me know and I can take it down.

Caution: This Incest Sex Story contains strong sexual content, including Ma/ft   ft/ft   Consensual   Drunk/Drugged   Lesbian   Heterosexual   Vignettes   Incest   Brother   Sister   Light Bond   Group Sex   Anal Sex   Double Penetration   Exhibitionism   First   Masturbation   Oral Sex   Voyeurism   Public Sex  

David pushed slowly, not wanting to hurt his little sister. She was looking at him with her big blue eyes, her blonde hair splayed out beneath her and biting her lower lip in trepidation. His rock-hard cock parted the labia as he flexed and slowly worked the head in.

“Ooooh,” moaned Sarah.

The room flashed as Rob took a picture.

“Sarah’s first fuck ... aaaaw”, Rob quipped. Sarah giggled while David looked concerned. “Just for the photo album, you know,” he explained. He put the camera on the table and sat down on the couch, stroking himself and watching.

“You ok, babe?” David inquired nervously. He hoped he hadn’t hurt her.

“Yeah, just fine,” she replied. “How much is in?”

“Just the head.”

“Put the rest in then,” Sarah moaned before closing her eyes and biting her lip again. David thought it was amazingly sexy.

He started pushing again, working his way in with little strokes. Whimpers and moans sounded from Sarah, but she never indicated that she wanted him to stop. She was like velvet, he decided. He had never been in anyone so soft and so tight before. “Should he worry about getting stuck?” he pondered.

Long seconds later, he was buried to the hilt. He just held it there for her to get used to it.

Her eyes popped open. “All the way in now?” she asked, sweat beading on her forehead.

“Yup,” said David. “How do you feel?”

“Wonderful,” she replied and smiled dreamily. “I’ve never felt so full. I think this thing is in my stomach.”

“I never felt a cherry. You sure you’re a virgin?” David wondered.

“Of course I am!” Sarah looked indignant. “I broke it one time in gym. I was trying to go into a split.” She blushed. “It was kinda embarrassing actually.”

“Ah. Sorry.” David kissed her on the forehead. “I didn’t mean to question your integrity.”

“Shut up and fuck me,” was her reply.

Not needing to be asked twice, David withdrew slightly before pushing himself back in. Sarah gasped loudly. Her hands gripped his sides. He repeated the motion with a little more length, and was rewarded with another gasp. On the third thrust she pushed back at him, her eyes tightly shut in concentration. David began a slow pistoning action, each time making the stroke a little longer. Before long, Sarah was beginning to twist and turn, moaning and clutching at the couch.

“Oh ... my ... God!” she exclaimed through clenched teeth. “Never ... ever ... stop!”

And David was of no intention to. She was amazing. By the time he was stroking full length, she was screaming and her face was contorting. He was pretty sure she was saying things, but the words came out like gibberish. Her fingernails were making red marks down his sides.

Sarah shook. Never in her life had she felt something like it. The sensations were sending sparks up and down her arms and legs, her head was spinning and her pussy was on fire. Her breasts were shaking back and forth and she wanted to grab them, but couldn’t because her hands were too busy clawing at the David. She could swear he was pushing a log into her, but it felt so good.

If she opened her eyes she could see the expressions on David’s face. There was intense concentration, intermingled with bliss each time he bottomed out. She could feel his sweat dripping on her and running down her body, each new drop sending a ripple of sensation from where it hit. When she concentrated, she thought she could feel the relief of the veins on his cock and the flare of the head as they scraped along her insides.

David was by now pounding in and out of the little girl, his strong arms holding her close. Wet, sloppy slapping noises filled the room has their hips impacted. He could feel her juices being pushed out and running down his balls with every thrust. Her flushed tits were bouncing vigorously back and forth as his eyes tried to follow the paths of her engorged nipples.

Sarah had already come twice. She imagined she was the redhead on the table under her brother.

“Oh yes!” she screamed. “Initiate me!!”

David managed a chuckle and Rob laughed out loud.

“You know,” said Rob to the moaning teenager, “the initiation is not complete for any of the girls until they have completed the Three-man Challenge.” He grinned. “What you saw was just the preliminaries.”

Sarah came again, hollering all the way, before replying breathlessly.

“Just ... the ... prelim ... inaries?” Each pause was accentuated with the slap of David burying himself in her. She put her little hand on his chest, urging him to slow down. She was still mewling and whimpering as he slowly stroked in and out. Rob nodded at her.

“So what’s the ... three-man challenge?” she inquired between breaths.

“Well,” Rob continued. “A girl has to take on three guys at once. When they all come in her, she is initiated.”

Sarah stared at him in disbelief. “Three at once!? How?”

“Well, you remember what I did with my fingers?”

Her eyes widened even further. Rob nodded. David slammed his cock into her once before resuming his slow stroking. Sarah gasped.

“Sorry,” he grinned.

Sarah glared at him. “Too bad we don’t have three guys here then,” she said to no one in particular. David and Rob looked at each other incredulously.

“Don’t you think ... losing two virginities ... in a day is plenty ... already?” David inquired, unable to believe how much had already happened, nor how much the little girl seemed able to handle. He teased at her opening for a second before plunging back in. He was rewarded with a sharp intake of breath followed by a moan.

“You know...” Rob ventured. “We have been known to do a Two-man Challenge if the situation warrants it.” Sarah looked at him curiously, trying to focus as her body was rocked back and forth. “Well, I mean, if a girl can handle the bottom two, the mouth usually isn’t that much of a problem.”

Sarah looked like she was considering it between David’s strokes.

“I wanna do it!” she declared.

“What!?” they exclaimed.

“Why not?” she asked.

David and Rob looked at each other again and shrugged.

“We should probably do it now then,” David suggested, catching his breath. “Cause I’m not sure if I’ll be able to get it up again after this.” He looked at Sarah. “You sure know how to wear a guy out.” His statement was punctuated with a solid thrust that left Sarah gasping.

Sarah opened her big, blue eyes and smiled impishly. “That’s why I have two, right?” She was rewarded with another thrust, even firmer than the previous.

“So you think you can handle two at once, huh?” Rob looked eager and had moved closer. “We should probably see if you could even handle anal sex first.” His fist was sliding slowly up and down his erection.

David slowly extracted himself from Sarah. Her eyebrows furrowed in obvious irritation.

“Where are you going?” she demanded.

“I need a break if you want me to last.” He stood up and she could see her juices coating his cock, dripping down his balls. With a burst of energy Sarah sat up and leaned forward, swiping the tip with her tongue.

“Mmm...” she uttered appreciatively. “That tastes so sexy.” She went to work cleaning David’s cock of her secretions and it was all he could do to not just blow in her face again.

Meanwhile, Rob had gotten up and was rummaging through his bag.

“Aha!” he exclaimed and pulled out a little plastic bottle. “I knew there was some in there!”

Sarah, after finishing David’s cock with a quick kiss on the tip, asked, “What’s that?”

“Body massage oil,” Rob replied. “It feels really good and is very slippery. Since this is your first time, I think we’ll need all the help we can get.” He winked at her. “Come here, you can help me apply it.” Rob sat down on the couch, his legs apart. He waved Sarah over to kneel between them and then handed her the bottle.

“Put a good dollop in your hands, then start massaging it onto my cock,” he instructed. “Get it good and slippery.”

She placed a kiss on the top causing his cock to lurch before following his directions. David came up behind her, grabbed the bottle and squeezed a bunch into his hands. He gave her a quick peck on the cheek before kneeling behind her and applying it to her ass. She moaned as his strong fingers massaged the oil into her skin, first just around the opening and then inside.

Pretty soon he had his finger pumping in and out, making squishy noises that caused Sarah to giggle as she started pushing back onto it. Rob’s cock was glistening and she was sure it wasn’t going to get any slipperier as she leaned back on her heels.

“Are you ready?” Rob asked.

“I think so,” Sarah replied, feeling a bit of trepidation now that it was time.

“Ok, get up on the couch, then, and straddle me, facing Dave.” Sarah hurried to follow his directions; suddenly worried she would chicken out. Once she was in position, she could feel Rob’s cock nestled in the cleft of her ass. She realized that she would have to raise herself up quite a bit before she could mount it. She looked ahead at David, who had picked up the camera.

“Might as well catch all the firsts,” he commented.

Rob pulled her backwards and instructed her to reach back to put her hands on the back of the couch. “Now you can lift yourself up with your legs until you’re at the right height,” he said.

Sarah did, while Rob steadied her with one hand under her ass. His other hand was aiming his cock. When she finally found the right position, she could feel the tip of his cock right at her sphincter. She was nervous now, and wanted to get it over with. She remembered how tight their fingers had been in there, and this was a whole lot larger.

Rob took his hand off her ass, causing her to slip down a little, the tip of his cock pushing against her tight ring. Sarah grimaced and then started to push slowly, pumping slightly up and down, trying to get a little more in each time. Suddenly, the head just popped past the muscle and Rob made a little lurch penetrating further.

Sarah moaned, and David took the opportunity to get off a shot of his teenage sister with his buddy’s cock barely inserted in her ass. David’s cock was rock-hard and jutting out in front.

“Try bouncing a little,” Rob suggested. Sarah did, and with each bounce he penetrated a bit deeper. Every inch was effort, as the organ slowly made its way into the little blonde. It hurt a little, but the massage oil was doing its job.

After about five minutes of bouncing, wiggling and rocking, Sarah found herself sitting directly on Rob’s lap and realized he was all the way in. And good thing it was too. Any further and she was certain it would be coming out her throat.

 
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