Jesse St. James
Jesse was going to make sure that he made their first time together so amazing that it cancelled out anything that came before. She’d forget all about Finn and he’d forget all about the girls that came before her. They were already gone from his mind because he was finally getting to make love to the girl he loved for so long. She was the only thing that mattered in the world right now and he was going to focus every ounce of his energy on her. This was the epic romance that he promised her so long ago and he was going to make sure it was done right. However, that didn’t mean they couldn’t have a little extra fun in between moments of romance.
When Rachel revealed that she had tried touching herself before a few times, but that she never got the hang of it, he chuckled and ran his thumb along her hand. “Its not that difficult. You just have to listen to the word of your body,” he explained, glancing up to look in her eyes to see if she got his reference. When he moved his hand for her to touch herself, he hoped that she wouldn’t grow shy and refuse. When she nodded that she would, he smiled and watched carefully as she pushed a single finger inside of herself. “Try another,” he whispered, biting his lip as he watched her insert two. He was about to instruct her to also touch her clit at the same time when she discovered it herself. “Feels good?” he asked as he rubbed one of her thighs. Realizing that he was wearing too much clothes, he pulled his sweater off and knelt down on the bed next to Rachel so he could kiss her while she continued to touch herself. As he kissed her, he began working at removing his jeans and boxers, having to break the kiss for a brief moment to get them off completely.
“Let me help,” he whispered with a smirk as he ran his hand down her body to replace her hand with it. He began rubbing slow circles against her sensitive nub with his thumb before inserting two fingers inside of her. He knew that because his fingers were much thicker and longer, it would feel even better for her. But now all of this was starting to make Jesse yearn for some reciprocation and he found himself grabbing her hand with his free one. Luckily, the position they were in with him knelt down next to her allowed for him to do this while touching her at the same time. He led her hand over to grasp his rock hard length and watched to see what she’d do next as he continued to pleasure her with his hand.
Though she was finally getting the hang of touching herself and it was finally starting to actually feel good, she was missing the absence of Jesse’s body against her, and found that she was beginning to crave the taste and touch of him. Just then, like he had read her mind and could completely understand what she wanted, his mouth was moving against her own. She eagerly responded to the kiss, using her free hand to lace her fingers into his curls and pull his mouth more securely against her own - kissing him intensely and moaning into his mouth from both his lips and the feel of her hand working against her womanhood.
Just when she thought it couldn’t get any better, Jesse’s hand had replaced her own, and because his hands were much larger than her own, as well as the fact that he was infinitely more experienced than she, feeling his hand working against her was a ton times better than her own. “Oh my god, Jesse.” Rachel whimpered in between quiet gasps and moans, thrusting her hips up against his hand to drive his fingers deeper within her and obtain more friction from his thumb against her clit. When Jesse moved her hand over his length, she bit her lip harshly to stifle a loud moan at the feel of his incredibly hard length in her hand - feeling how large it was helping to turn her on even more, and her want for him to go tenfold. She immediately began stroking him, tuning out the part of her that was worried that her inexperience would make her no good at touching him and just opting for going by instinct and just relishing in just how good it felt to have Jesse in her hand, as well as feel his own hand moving against her.
Jesse St. James
If Jesse thought the sounds Rachel was making while she touched herself were hot, they had nothing on the sounds she made when he was the one doing the pleasing. “Don’t hold back, Rach,” he whispered against her lips, encouraging her to be as vocal as she wanted. He watched in awe as she thrust her hips up in a way of making his fingers go deeper inside of her. Wanting to give her exactly what she wanted, he began pumping his fingers in and out of her deeper and at a faster pace. He tore his eyes from what he was doing to her to focus on what she was now doing to him. His eyes widened as he watched her small hands stroke him so perfectly. Tilting his head back, he couldn’t stifle the moan that managed to escape even if he wanted to.
He moaned her name and began thrusting his hips into her hand to make it feel even better. But he knew that he couldn’t keep this up or he’d finish far too soon. “Rach…” he moaned, looking down at her and licking his lips. “I want you so badly right now,” he growled. If they continued with the foreplay any longer, they’d both come undone before they could truly be intimate and Jesse wasn’t having any of that. He needed to be inside of her right now and make their bodies become one. Running his hand through his hair, he thought about protection and looked around slightly. Having not been sexually active for a while, he wasn’t exactly fully prepared. “You wouldn’t happen to have any…” he asked, trailing off with a gulp.
Rachel bit her lip to restrain her wide grin that threatened to spread across her face at the loud and long moan that came out of Jesse’s lips in response to her hand wrapping around his hard length, the knowledge that she had succeeded in pleasing him as much as he was pleasing her making her pride swell. She had only had sex with Finn once, and they had barely really done any foreplay - leaving Rachel somewhat worried that she wouldn’t be able to please Jesse once they finally did this. However, if his reactions were any indicator, she was doing a good job, which made her incredibly happy. After all she had done to him, the least that she could do for Jesse was please him sexually.
Having him thrust his hips up against her hand to get more friction had her moaning loudly, the combined feeling of his stiff length in her hand and his expert fingers working masterfully at her entrance driving her insane, and she knew that she wouldn’t be able to handle all this wonderful torture any longer. Thankfully, Jesse seemed to be on the same page as her, what with him saying how badly he wanted her - obviously indicating to go all the way. She nodded firmly in agreement, and was about to pull him into a kiss, when he asked about protection. She shook her head, wrapping her arms firmly around his neck and pulling him close. “I’m on birth control, Jesse. Just do it. Please. I need you.” She murmured, pressing warm kisses up and down the column of his throat in between words.
Jesse St. James
Jesse sighed in relief when Rachel informed him that she was on birth control. Now they wouldn’t have to worry about the fact that they didn’t have any protection on them. The fact that she was already on birth control excited him more because it meant that he would get to fully feel all of her without having the barrier of the condom between them. Hearing her practically plead for him to enter her made him practically shiver with desire. Moving over her, he parted her legs so he could position himself in between them. He ran the head of his length along her entrance and moaned at the feel of their most sensitive areas rubbing against each other. Unable to hold back any longer, he entered her with one swift thrust that immediately brought a moan of her name to fall from his lips.
Running his hands along her sides, he leaned down to capture her lips in a bruising kiss as he began thrusting in and out of her at an even pace. The pleasure of it all made it hard for him to focus on their kisses, though, so he settled with resting his forehead on hers and looked her in the eyes. “I love you,” he whispered, kissing her quickly before moving his lips down to her neck. He gently nipped and sucked on her pulse point, making sure to leave her a mark that would remind her of what happened between them for her to discover later. Missing her lips, he reclaimed them in a slow and loving kiss that took his own breath away.