The sun had long gone down and they were walking side by side under the street lights back to her room. It had been about four weeks since Oscar had first gotten up the nerve to ask if she wanted to go to dinner with him that night, and although he had been shaking like a leaf as he stood before her, she had said yes.
She actually said yes!
He knew he had sounded like a complete idiot as he stuttered through conversations, but he had tried so hard. He had even brought her flowers. He honestly hadn't been certain whether the night had gone well or not, as he had never been on a 'date' before, but when she asked if he wanted to see her the next day he almost yelled out in the affirmative.
It was now a month later and they walked along the brick sidewalks, Oscar chatting away to cover the anxiety building in his stomach. He had never been to a girl's rooms before…
She sensed his discomfort and gently placed her hand in his, linking her small fingers between his long slender ones. Oscar no longer jumped like he had the first time she had held hands with him. By now they had held hands and maybe even kissed a few times… Oscar smirked to himself at the thought. He had actually kissed a girl! And more than once!
They finally reached her door and she led him inside. Oddly enough he was a little disappointed when the room looked almost identical to his. He had always expected girl's rooms to be… different, fancier maybe. He looked around and spied a tank sitting on her dresser across the room and walked over to it.
"You have a fish?"
"Mhm," she said. "I used to have him at home, but Mother brought him when she came to visit earlier this year. She said she thought he would remind me of home, but I think she was just tired of feeding him."
Oscar laughed heartily as he always did around her. She could always make him laugh.
He pressed his face to the glass and smiled wide as he watched the little blue fish swim around and around. He had a childlike wonder about him that she couldn't get enough of, and to her he was perfect in his own odd and timid way.
She gathered her courage and walked over to him. She took his hand once again and pulled him away from his new friend. She led Oscar to the bed and as soon as he hit the mattress she could see his lanky body tense up. She leaned forward and pressed her lips to his.
Did she really want this? Was she ready?
She had thought about this for a long time, but she knew where she wanted to go with this, with him.
Oscar sat frozen as every fiber of his body was acutely aware that he was sitting on a bed, on her bed. Maybe she just wanted him to be comfortable. His eyes darted around the room- he could've sat in the chair at the desk…
He jolted when he felt her hands against his cheeks and he had to tell himself to calm down, that all they were doing was kissing. They had done this before, it was no big deal… except they'd most certainly never done it on a bed.
Beds were for other things…
He forced his eyes closed and screwed them tightly shut. He had learned that you weren't supposed to keep your eyes open while kissing, girls didn't like that.
She moved and sat down next to him, never letting their lips break contact. She had long ago learned that if you stopped for even a second, Oscar would take off running. He really was a terribly shy creature.
She licked along his bottom lip and earned a small whimper from her partner, but he obediently parted his lips. She gently touched her tongue to his, careful not to scare him off too soon. They had reached this far once before but had immediately stopped when Oscar had suddenly been struck with a panic attack. It had taken her almost a half an hour to calm him down.
Oscar took a deep breath through his nose when he felt her tongue brush against his. He wouldn't panic this time. He wouldn't. He didn't like being so afraid of this kind of… stuff. It had taken him a long time to get used to kissing. It was so wet, which was weird but also kinda nice in an odd way… kissing made him feel funny.
She moved closer and placed her hand on his slender thigh so gently that she wasn't even certain he realized what she had done. She moved her hand upward but hadn't gone far before Oscar pulled abruptly away.
"Shhh… it's okay," she said and pulled his head back toward her. An uncertain noise escaped him but he allowed his mouth to open again. He trusted her.
They continued like this for a while with her continuing to touch his body in new ways, getting him used to the feeling. She ran her fingers through his red hair, making it look even more wild than usual, held her palm against his chest, ran her hand farther up his thigh. Eventually she began to push him backwards onto the bed and was surprised when she felt no resistance.
For the first time in maybe his entire life Oscar wasn't thinking, wasn't analyzing, wasn't avoiding. He was simply feeling. The only thoughts running through his mind were that she was very pretty and that it was getting awfully hot in the room.
She was kneeling over top of him with her legs resting on either side of his thin hips. She opened her eyes for a moment to peek down and she smirked when she saw the clear definition of his enjoyment through his pants. She ran her hand downward from his neck, over his shirt, and lingering just long enough on his belt before allowing her fingers to brush over his arousal.
The reaction was instant. Oscar was immediately aware of her body pressed against his, her legs holding him captive, her hand touching him. He jolted upward and almost smacked his head against hers.
She immediately removed her hand and placed her palms against his chest, "Oscar, it's okay. Calm down… shhh."
His red hair moved wildly as he shook his head harshly back and forth. He began trying to brush her hands away but she grabbed his wrists and stopped his movements. She didn't move from her position, wanting to show him that she had no intention of getting up and ending this. She continued to murmur soothing words in his ear and after a few minutes he slowly calmed. His eyes were screwed shut and his hands were clenched into fists, his face turned downward.
"Oscar, look at me."
When she got no response she released his wrists and lifted his face, "Open your eyes."
He slowly, very slowly, opened his eyes and peeked up toward her. His eyes met hers for only a second before darting back down.
"Are you okay?" She asked.
He shook his head minutely and she leaned forward.
"Just trust me," she murmured in his ear and gently pushed him back onto the mattress. She didn't even bother with kissing him this time, knowing that he was wound far too tightly to forget what was happening again.
She moved her hand down and lightly touched him again, this time not feeling the same hardness that she felt only a few short moments before. His body tightened but he stayed still.
"Breathe, Oscar," she said with a laugh. He released the breath he had been holding and slowly turned his eyes downward. She was touching him THERE. He had never been touched there before by anyone else, and only a few times by himself, aside from bathing of course. But the times he had used his own hands had never felt like this, had never felt this good.
He released a soft moan and she smiled up at him, pleased to see his pants tightening once again and feeling him hardening under her hand once more. She rubbed over him and realized that there was nothing else in the world she wanted to watch besides Oscar Hopkins squirming in pleasure.
He could hardly hold still- not that that was anything new, he could never keep still anyway. His pants were quickly becoming uncomfortable but yet he didn't want her to stop. It was then that he realized he wasn't touching her. Was he supposed to? He was pretty certain he was. His mind raced as he wondered what to do. He thought back to some of the magazines he had seen a few of the boys reading at school, but there was no way he could do that… but he wanted her to feel happy too, he wanted her to feel the same nauseating but oddly pleasurable feeling that he was.
When he leaned forward she braced herself for another panic attack, but instead was surprised to have him pull her closer to his body. Her hand slipped away from his arousal but he knew that was okay because it was her turn now.
He thought back to those magazines and tried to mimic what he had seen. He nervously touched his fingers to her neck before slowly sliding them downward. He swallowed thickly when he reached her breasts, a place he had tried in vain to keep his eyes away from when they were together. He rested his hand there before leaning forward and pressing his lips against hers. She made a noise and for a moment he thought he had hurt her and was about to pull away when she crushed her lips harder against his. She pushed him back down onto the bed and her fingers immediately slipped his thin suspenders from his shoulders and began unbuttoning his white shirt. It took all of Oscar's strength not to jump up from the bed and run half naked into the cold night.
He jerked when her hands touched his bare chest but he forced himself to stay still. She wasn't hurting him and she was obviously enjoying herself, so he stayed still and let her continue. It wasn't long before his shirt was gone and she began undoing the buttons on her own shirt before throwing it aside.
Oscar's pants were definitely much too tight now as he laid still and watched in awe as she stood and slipped her skirt off. She returned to the bed and he really had no idea what to do next as he was most definitely not going to touch her in her current state of undress. Oscar had gathered enough courage for one night thank you very much.
He found himself staring at her half exposed breasts when he felt a hot and wet heat against his prick. His entire body jerked and his hands flew to his mouth to stop a shriek as she mouthed him through his pants. He breathed quickly and heavily and was pretty certain this was the most terrifying thing he had ever done, but yet as her tongue pressed against his clothed erection he couldn't imagine asking her to stop.
It wasn't long before her bra and panties disappeared and she was completely naked. The moment her fingers touched his belt he covered his eyes with his hands and she eased him from both his pants and underwear. She heard a few tiny whimpers and gave him a few moments to collect himself. She was amazed she had gotten him this far, but she had a feeling the hard cock now pressing against her bare thigh had something to do with it.
When his breathing slowed he peeked through his slender fingers. His eyes roved over her entire body, from the top of her head all the way down to her feet. He was in awe. He had never seen a girl naked in real life, nor had he really expected to any time soon. But he was so happy when he was with her, and if she wanted to do this then he would try. He had no idea what to do but he would try as hard as he could for her, to make her happy.
She gently eased his hands away from his face and leaned forward. She kissed him and he smiled as her hair brushed against his face.
His eyelids grew heavy as he felt her hand on his bare cock. He watched as she lifted herself up before slowly kneeling down just enough for his hard prick to touch her core. It was hot and wet and Oscar was certain he was about to faint. He couldn't bring himself to do anything but lay there with his hands gripping her thighs, trying desperately not to squeeze hard enough to cause her pain.
She rubbed his cock through her wet folds and watched as he clenched his teeth and stared intensely at the ceiling. His breathing was already ragged and they hadn't even begun.
Slowly, inch by agonizing inch he was enveloped in the hottest wettest heat he had ever felt.
He was in Heaven.
His eyes closed and his mouth opened and his hips thrust forward on their own accord.
"Don't move," she said and his eyes popped open at the pain in her voice. He immediately lifted his head and saw her face screwed up, her teeth grinding together.
He felt horrible. He had hurt her!
"I'm, I'm, 'm sorry. I don't, I just-" he stammered, unsure of what to say and half afraid to move another centimeter for fear of causing her more pain.
"No no, it's okay, just wait," she said as she continued to lower herself onto him. She could feel her tight channel molding itself to him, could feel his cock slowly opening her. She finally sat fully on his lap and took a deep breath.
Oscar had to move, oh God he needed to move! But he didn't, he stayed where he was and gripped the sheets under him until his knuckles turned white.
He would not move. He would not hurt her.
He began this mantra in his head and gasped when she felt her shift.
Oh God oh God oh God…
She shifted on his lap and he gritted his teeth together, allowing only the smallest of sounds to escape from his throat. He had never felt anything so good in his entire life, and judging by the sound of it she was slowly beginning to feel the same way.
She circled her hips and he had never felt something so tight and so hot in his life and he never wanted it to end. After a few moments she lifted herself up before easing back down. She continued to slowly fuck herself on his cock until the pain ebbed away and all she felt was pleasure, until all she felt was him filling her.
"Oh God, Oscar…"
He moaned loudly at the way his name sounded on her lips. Through still-clenched teeth he stuttered, "Move? Now?"
"Yes! Yes please move."
It was as if his body had been released from a tight grip as his muscles immediately relaxed and his hips thrust harshly upward. They both shouted out in pleasure as his cock drove into her even deeper. Whatever hesitation Oscar had previously felt it was long forgotten. All he knew was the instinctual thrust of his hips and that he never wanted this feeling to end. He didn't have to worry about what to do anymore, his body knew exactly what it wanted.
Despite a few moments of awkward, unsynchronized movement, they were soon rhythmically moving together as she bounced on his cock and he pushed up into her. He threw his head back into the pillow and held onto her hips, driving her down onto his cock.
They moved as if they were racing one another toward orgasm, neither of them having felt anything like this before. She leaned forward and put her hands on his chest and continued to bounce her hips up and down, driving him into the mattress.
The tight wet friction on his cock soon became too much and it didn't take long before he felt a tightening in his lower body and his cock begin to throb.
"I, I can't-"
"It's okay," she panted. "Come on, Oscar. Come for me."
"Ah, ah, AH…" he gasped as his hips stuttered in their movement before slamming upward, driving him even deeper into her as he released.
His eyes screwed shut but he heard her scream and felt her walls clench down impossibly tighter onto his pulsing cock. He couldn't breathe, couldn't see, couldn't move, and yet when his breathing finally slowed and he lay there bonelessly, he couldn't wipe the sloppy grin off his face…
