With Benefits – Chapter 1

The first time they did it, Freddie was pretty confused. Not only because his only experience with the other gender up to that point had been strictly confined to late nights sitting in front of his computer screen, mother asleep, door locked, and headphones on with the volume turned all the way down, pumping a tightly clenched fist quickly up and down in his lap, but more importantly because he had been pretty sure that Sam hated him with every last fiber of her being. And, the last time he checked, you didn’t just go and have sex with someone you hate.

It was the summer after junior year and Freddie had just finished brushing his teeth and was about to go to bed when his cell phone rang.

“Hello?”

“Hey Fredward.”

“Sam? What do you want?”

“Can you come over here?”

“What? It’s past 1:00. Why?”

“Can I not just want to see you?”

“…”

“Look, you can either come over here by yourself or I can come over there and make you.”

“OK, fine. Whatever.” Click.

Freddie pulled on a T-shirt and a pair of jeans, kicked his shoes on and quietly snuck out of his room, being careful to avoid that spot in the hallway with the weak floorboard so he wouldn’t wake his mother who was asleep just down the hall. He snatched his keys from the tray by the door and then slid out of the apartment without making so much as a sound.

It was 1:15 when he pulled up to the curb in front of Sam’s house. He saw the light in Sam’s window on as he was walking up the path, so he didn’t bother to ring the doorbell or knock. A few moments after stepping onto the porch, he heard the locks on the door being undone and soon the door was open and he had stepped inside. Sam motioned for him to be quiet as he stepped through the door and kicked off his shoes; tiptoeing, she led him through the house to her room.

He took a few steps into the room so he was standing at the edge of her bed. She followed him in, closing the door behind her and turning the lock.

“So why am I here? It’s one o’clock, for Chriss—” Freddie began to say. But he was interrupted before he could finish as Sam stepped forward and brought her mouth crashing onto his in probably the most aggressive kiss Freddie had ever seen. And he wasn’t even sure that kisses could be aggressive.

Recovering from the brief shock, he pushed her off, taking a quick step back. “What the hell was that?” he said in a hushed yell.

“Just shut up,” Sam said, as if that were an answer, and advancing on him again.

She gave him a quick shove, forcing him onto the bed. Before he could protest again, she had leapt in one lithe movement from the floor onto the bed, straddling her legs across him and holding down his wrists. She leaned her head down and brought her lips up against his again, this kiss just as aggressive as the one before.

Sam’s long, blonde hair fell around Freddie’s face, filling his nose with her scent. He could feel the heat rising in his face, making his head light and turning his cheeks red, but more importantly he could feel the heat rising in his crotch. He struggled against Sam, trying to prize his hands free and escape before their close proximity revealed his growing erection and changed the situation from horribly awkward to downright life-ruining. Sam had always been the stronger of the two, however, and Freddie could not break free.

Just as Freddie was beginning to see lights, Sam broke off the kiss and raised her head so her face now completely filled his vision. Her mouth was crooked in a smirk and Freddie felt her slide down his stomach and over his belt, coming to a stop just above his crotch. A quick, high-pitched yelp, followed by a low moan escaped Freddie’s throat as Sam lowered her hips onto the bulge in his jeans, grinding down in slow circles.

“So you do actually have one,” she laughed, her smirk widening into a full grin.

Freddie would have liked to have shot back some retort, some insult, something to save him the indignity; all he could manage, though, was to grunt “Uh…” and weakly nod his head. A part of Freddie was painfully aware of how hard he’d become as Sam continued to grind against him, dying of the embarrassment and screaming to push Sam off and run. But that part had been pushed off to the very corners of his mind now by the waves of sensation washing over him, and another part of Freddie, a part that the boy himself was not aware even existed in him, began to take over.

So when Sam leaned down to bring their lips together once more, instead of lying paralyzed beneath her, he kissed her back, bringing his left hand up to the back of her head, digging his fingers into her hair; his right he brought up to her back, grabbing a fistful of her shirt and pulling her down against his chest. He shuddered as he felt Sam begin running her hands through his hair, down his neck, across his chest, and finally over his crotch; Freddie let out a short cry against Sam’s cheek as she firmly closed her hand around his dick through the fabric of his jeans, his hips bucking involuntarily.

When Sam broke off this time, she raised herself up, pulling Freddie up along with her, so he was sitting on the edge of the bed and she was kneeling across his legs. Still grinning that same ear-to-ear smile, Sam brushed her hair back behind her shoulders and reached down for the hem of her shirt; she pulled the shirt off in a quick motion and tossed it aside onto the floor, revealing a bra colored the palest of pinks.

“Well don’t start drooling,” he heard Sam say. Freddie suddenly became aware that he’d been staring at the curve of her left breast, his mouth hanging open; indeed, a bead of saliva had begun to leak out of the corner of his mouth.

“Right, sorry,” he said, his cheeks flaring red. He quickly closed his mouth and swallowed.

Sam sat back on her heels and gestured with two fingers in an up and down motion at him. “Shirt,” she said.

“Oh, yeah,” he said, nodding quickly a few times. He reached down to the hem of his shirt and pulled it quickly over his head, throwing it onto the floor as well.

“That’s better,” Sam said softly, leaning forward again and placing her palms around his waist. Freddie felt like electricity was running through his skin as she slid her hands up his sides, across his abs, up his chest, over his nipples, and finally over his shoulders. She leaned back quickly once again, reaching with one hand behind her back and undoing the clasp of her bra with one snap and sliding it off her shoulders and onto the floor, before locking her arms around his neck and moving in to kiss him again. The feeling of Sam’s skin against his, her firm nipples poking lightly into his bare chest, made Freddie’s head spin as he wrapped his arms around her and ran his hands along her back.

Sam soon broke their lips apart, only, to Freddie’s great surprise, to start trailing kisses all across his body. She kissed his neck, sucking slightly on his collarbone; she kissed his shoulder; she kissed his chest; she kissed his nipple, sucking it slightly and circling the tip of her tongue around the now firm pink nub, making Freddie moan again in pleasure; she kissed his stomach, nuzzling his navel lightly with her nose.

When he felt the little pecks of Sam’s lips across his flesh stop, Freddie craned his neck forward to meet Sam’s face, still fixed in that wide grin. She rubbed her hands across his chest once again before standing up. Propping himself up by his elbows, Freddie watched as Sam slowly undid her jeans, sliding them down her legs to reveal a pair of panties in the same pale pink as her bra. Freddie felt Sam’s hands on him again as she knelt down on the floor in front of the bed and began to undo his belt followed shortly by his pants; he helped her slide the pants off his legs, revealing his black boxer-briefs, tenting in the center from the pressure of his cock straining against the fabric.

Sam wrapped a hand around his cock and balls through the fabric of his underwear, briefly massaging them in slow circles. Finally, she slid the boxer-briefs down his legs, the tip of his dick catching against the elastic band as she did and snapping back against his chest.

Reflecting later, Freddie would find that somehow, laying there completely naked on Sam’s bed, Sam hovering over him, herself naked all but for her panties, he did not feel the least bit awkward, nor did he feel as though his life had been ruined, nor did he feel an ounce of embarrassment. Somehow, that moment had felt inexplicably right, and somehow rang inexplicably true, despite the complete craziness and utter confusion that had surrounded the rest of that night.

But at that moment, Freddie didn’t have the luxury of being able to think straight. Sam crawled up onto the bed beside him, wrapping one arm around his neck and bringing him against her. She kissed him again, running her other hand all across his body. Her hand moved down the entire length of his erection before closing firmly around the center of his shaft; Freddie yelped again as a tremor that probably would have registered a solid 7 on the Richter scale shot through his body. He thought he might come then and there, but managed to pull himself back from the edge, if only just.

“Oh shit,” Freddie said, throwing his head back before burying his face in the curve of her neck, as Sam began to pump her hand up and down across his cock. He moaned against her neck and his heart began to race even faster as she quickened her pace.

“Shit, Sam… I’m…” Freddie gasped. Sam released her grasp on him and brought both her hands up to position his face in front of hers. She guided one of Freddie’s hands to her breast, making massaging motions; he continued to squeeze her breast when she removed her hand, causing her to moan and squirm against him. He continued like this until Sam’s hand returned and began guiding his down her body to the hem of her panties which he helped her slide off.

“Touch me,” she breathed, more a command than anything else, guiding Freddie’s fingers down to her vagina; Freddie swallowed hard and then complied. She moaned and sighed into his mouth as he rubbed her folds. After a moment, Freddie felt Sam’s hand on his again slowly push his forefinger between the folds of skin and inside her. She broke their mouths apart and continued to moan with increasing intensity as she guided his finger around the inside of her vagina. He watched her face contort with pleasure as she moved his finger to massage the flesh surrounding her clit.

Freddie continued to finger her, her breaths growing shorter and more erratic by the second, until she pushed his hand away. After a few breaths, she looked him in the eye, still grinning widely, and said, “I want you inside me,” her voice dripping with what Freddie would later mark as pure lust. At the moment, however, Freddie had absolutely no idea what Sam meant until she quickly flipped over on the bed, reaching for her nightstand. Pulling the drawer open, she fumbled around inside and produced a small packet that Freddie initially thought might have been a moist towelette but that he soon realized was actually a condom.

“You know how to put one on?” she said, tossing the little packet in front of him on the bed.

“Uh, yeah, sure,” he said back, grabbing it and fumbling to tear it open. He tried to think back to the video they’d shown in health class freshman year as he unrolled the condom onto his hard dick. When he finished, he looked up to see her grinning down on him.

“Good work,” she said.

They moved up so they were now properly lying on the bed, Freddie still on his back and Sam on her hands and knees beside him. When they reached the head of the bed, Sam straddled his hips again and positioned the tip of his cock, which was trembling and twitching slightly, at the entrance to her vagina.

The wave of utter ecstasy that washed over him as Sam plunged his dick into her hit Freddie like a ton of bricks. “Oh, God!” he cried as Sam began to move up and down on top of him. The warmth of her and the tightness surrounding his cock nearly drove Freddie mad. He moved both his hands to grasp her hips and began thrusting deeper into her as she rode him harder, faster.

“Oh shit… fuck, shit… unngh! Shit… oh, fuck…” The stream of profanity continued to flow out of Freddie’s mouth as he matched Sam’s quickening pace, synchronizing his thrusts with hers.

Soon Freddie felt that familiar feeling building within his crotch; this time, however, the feeling was much stronger than anything he’d ever felt before. “Fuck, Sam… I’m gonna come…” he said. But Sam didn’t respond, only riding him harder and harder.

Freddie thrust in furiously a few more times before finally feeling himself tip over the edge. “Oh!” he screamed as his orgasm washed over him and he felt the cum pumping out through his dick. Almost simultaneously he felt Sam’s walls contract around him and she called out too. The two rode out their orgasms against each other, continuing to thrust and grind until the final shocks of pleasure had passed.

After a moment and a few breaths, Sam climbed off of Freddie as he slid himself out of her. Sam stepped off the bed and walked over to the pile where they had thrown their clothes, picking up her panties and sliding them on

Freddie sat up on the bed and slid the condom off his dick. “Uh…” he began to say.

“Over there,” Sam said as she picked up her bra and put it on, pointing over to a wastebasket between her desk and bed.

“Ah,” Freddie said, leaning over and tossing the condom in it. He moved over to the edge of the bed and swung his feet onto the floor, sitting up. “Sam…” he said, looking at her back as she bent down again to fish through the pile of clothes.

“You can go now,” she said, tossing his underwear over her shoulder and into his face; they were followed shortly by his pants.

“Sam, I want to know what just happened,” he said, getting up and stepping into his pants.

“I just needed to blow off some steam,” she said matter-of-factly. She tossed his shirt over to him and he put it on.

“Sam, I…” Freddie began, taking a step towards her. But she cut him off.

“You should probably get home before your mom calls the National Guard,” she said, walking to her dresser and pulling out a pair of pajamas.

“Yeah, right…” Freddie said, still confused. He started to say something else, still wanting to press the matter, but realized before he did that it would be no use. Instead he simply picked up his socks from the floor, undid the lock on the door, and left.