That Night

Summary: Rory and Dean's first night together in her room. Missing Scene from Raincoats and Recipes. I might shown Rory as a little more innocent than she might have been but than again Rory grew up with just her mom no dad or brothers so she could be that innocent about naked guys.

Disclaimor: I own nothing.

Rory laid down on her bed with Dean on top of her as he kissed her laying over her. She moaned as she felt his hands in her hair as he pulled her against him. He moved his mouth to her neck and started sucking on it as Rory moved her head over to give him access to it. Dean smiled as he continued to suck on her neck as she moved her arms around his neck as she pulled him down on top of her. Dean tried not to put his entire weight down on her body. She was small and he didn't want to squash her with his body. He said, "Are you sure about this? I know you're still a virgin."

Rory said, "yes I'm sure Dean I want this. I want you to be my first. I love you."

Dean said, "I love you too Rory."

Dean moved them so that they were laying the normal way on her bed. Rory moved her hands down to the bottom of his t-shirt. She pulled on it trying to feel more of his skin as he moved to give her room to pull it off. She pulled it off rubbing her hands up and down his chest. She felt comfortable with that cause they had gone this far when they dated in high school. She rand her hands down his chest and pinched his nipple. Dean moaned and moved his hands down her body to her ass. Rory started kissing down his neck as he grabbed onto her ass as he felt his body react to her kissing. He was already hard at the thought of finally getting to do this with the woman he loved since he was 16.

Dean pulled her skirt of her dress up to her hips wanting to touch her skin he looked up at her giving her time to stop him, but she wasn't interested in stopping her as he started pulling her dress up over her hips. He loved how soft her skin was as rubbed her legs and hips through her underwear. Rory moaned and moved her legs apart a little bit to give him more room as he pulled more on her dress. He tried to pull it up off of her and finally he pulled up in fustration from where he was kissing her neck. He said, "Rory baby can you sit up a bit."

She looked up at him a little suprised and than looked down where he was trying to pull her dress up and off of her. She said, "oh sorry."

Dean pulled himself off of her and pulled her dress all the way off leaving her in her bra and panties. He looked at her half naked body as she smiled up at him. He said, "beautiful."

He leaned back down and started kissing her on the lips again as he ran his hands down her body. He rubbed her boobs through her bra as she pulled on his hair while kissing him hard on the lips. Dean slipped his tongue into her mouth as he pinched her nipple through her bra. Rory whimpered as he moved his mouth down to her neck again. He smiled as he felt her nipples starting to harden under his fingers. He could tell she was really getting turned on.

Rory couldn't believe the sensations that Dean was causing in his body with his hands and mouth. She felt his tongue licking her neck where her pulse point was she bucked her hips as he contuined to play with her nipples through her bra. Rory felt the material of his jeans against her panties and said, "I'm in my underwear and your still wearing your pants."

Dean said, "is that your way of saying that you want to see me in my boxers?"

Rory said, "yes I want to see more than just your boxers or we're not going to do this right."

Dean laughed and kissed her on the lips as he stood up and started unbuttoning his jeans. Rory actually looked with fascination as he pulled his jeans down his hips and looked at her big eyes. Dean realized that she may not have ever seen a man naked before. Dean looked down at her and said, "Rory have you never seen a man naked before?"

Rory turned red when and said, "yeah you know I was raised by mom and have no brothers."

Dean pulled his pants down the rest the way and said, "don't be embaressed baby. I like your innocence."

Rory nodded and laid back on the bed as Dean climbed back on top of her as he kissed her again as she grabbed onto his hair again as he began to kiss her again. They kissed heavily with their tongues dueling for dominance as Dean started reached behind Rory to unfasten her bra. Rory gasped as he pulled her bra off her body and threw it in the floor with the rest of their clothes. Dean looked at her boobs as she bucked her hips a little to him. He felt her squirm a little as he leaned down and kissed her chest down to her boobs. Rory was moaning and had her hands in his hair again as he started sucking on one of her nipples. He smiled as he felt her buck her hips to him again rubbing herself against his erection. He could feel her wettness through her panties and his boxers. He continued to suck on her nipple as he let his hand wonder down to the top of her panties. He once again paused to give her a minute to stop him but she was moaning and really into the sensations going through her body. He pulled her panties off throwing them to join the rest of their clothes.

He set up for a few minutes to finally take a look at her naked body. He liked the way her body was she had good sized boobs and was curvy. He touched her hips and looked up at her as he ran his fingers through the thatch of hair she had above her vagina. Rory was watching what he was doing when he looked up from where he was touching her. Dean leaned back in and started sucking on her nipple again as he gently spread her legs open a bit.

Rory tensed as she felt his fingers start to rub the outside of her pussy. Dean gently pulled back up and started sucking on her neck again trying to distract her. She moved her head to the side whimpering as he bit down on her neck. He knew that she was nervous and really he was to he had never been with a virgin before, and was afraid that he would hurt her. He moved his finger up to her clit and started rubbing it as he continued to suck on her neck. Rory moaned and started to relax a little as she let the pleasure overtake her. She started to get brave and decided she wanted to feel Dean as well so she reached between them toward his boxers. Rory pulled his boxers out and looked down them and eyes grew big at the sight of him. She nervously let his boxers go and looked up at him as he smiled.

He said, "its not going to bite you."

Rory blushed again at his comment. She said, "I know that it just looks so big. Is it even going to fit?"

Dean gently took her hand in his and moved it down to where his boxers were. He said, "Its going to fit don't worry. It might hurt at first, but it will fit."

Rory said, "yeah my mom told me about that when I was 16 after they caught us at Miss Patty's. I think it was in hope I wouldn't have sex with you. That was after I spent 2 days trying to convince her we didn't have sex that night."

Dean smiled and said, "yeah I don't think we ever conviced some people that we didn't have sex that night."

Rory laughed and realized while they were talking she had relaxed and was even rubbing him through his boxers. She looked down at were her hand were and smiled up at him. He said, "ready for me to take them off so you can see the whole thing."

Rory nodded and looked up at him as Dean stood up and pulled his boxers off as well. He reached down to his pants and grabbed the condom that he had brought with him out of his back pocket. He sat it on the bedside table though because they still were not quite ready for that yet.

He laid Rory back down on the bed and climbed on top of her. They went back to making out for a few seconds before Dean started letting his hands wander down her body. He leaned down and started kissing down her body teasing her nipples with his fingers while sucking on her neck again. He moved his mouth back down to her breast sucking on it again as he trailed his fingers down to her pussy. He ran a finger up and down the outside of her entrance. Rory bucked her hips to him as he bit down hard on her nipple as he pushed his finger inside.

Dean moaned as he felt the tightness around his finger. He couldn't wait to feel that around his cock. He said, "god you're tight baby."

Rory moaned as she bucked her hips to his finger as he pushed it in and out of her wiggling it around a bit. Rory pulled his head back up by his hair and started kissing him again as he fingered her hard. He slipped another finger inside her feeling resistance from the tightness. Rory whimpered a little as she felt herself stretch around his fingers giving him access to her. He bit down on her neck again as she bucked her hips moaning as he fingered her hard. Rory cried out in pleasure against Dean's chest as he continued to finger her getting her worked up.

Dean couldn't believe how tight and wet Rory was just around his fingers. He looked down at her naked body under him. Rory was once again looking down at her body were his fingers were playing with her. He pushed in harder as she cried when he hit her gspot giving her intense pleasure. He decided he just had to have a taste so he leaned back in kissing down her body this time not stopping at her boobs. Rory moaned and said, "Dean what are you doing?"

Dean licked her belly button and than looked up at her and said, "you'll see believe me you'll like it."

Rory watched with big eyes as he kissed down her body to her vagina. He moved her legs further apart and licked her clit first before sliding his tongue down the outside of her vagina. She grabbed onto his head as he started teasing her licking and sucking making her moan harder. Rory bucked her hips to his tongue as he slid it up and down her licking her clit and than sliding it back down to her slit. Dean could feel her walls tightening around his fingers even more and knew that she was close so he moved up and started sucking harder on her clit. She screamed out in pleasure as she came from the sucking and fingering.

Dean slid back back up on her body as she came down from her orgaism as he let her ride it out bucking on his fingers. He laid down next to her cuddling her for a few minutes as he let her recover. He had one hell of a hard on now, but he didn't want to go to quickly and hurt her.

Rory came down from her orgaism and realized Dean had stopped kissing her and was laying behind her holding her. She could feel something hard sticking her in the back though and knew that it was him. She pushed back into him and said, "that felt good but we haven't taken care of you yet."

Dean moaned as her ass made contact with his erection. He kissed her bare shoulder where it laid against his chest. He said, "I was just giving you a few minutes to recover before we went there. Are you ready?"

Rory turned around to face him which was a little hard on her small bed. She nodded and kissed him again as he once again pushed her flat on the bed and laid on top of her. She spread her legs open for him as he moved his hands down to her vagina again to make sure she was still wet. He smiled as he felt her she was soaking wet. He reached over and grabbed the condom off of the bedside table. He opened the package and pulled it down on himself as Rory watched. She said, "its big."

Dean saw the uncertainity and tenseness come back in Rory. He kissed her and said, "It'll be okay baby I swear I'll go as slowly and be as gentle as I can be ok."

Rory nodded and kissed him back as she spread her legs open and pulled him down on her. Dean started biting down on her neck as he positioned himself over her. He rubbed her with his dick a couple times to let her get used to the feeling of it and than put it to her entrance. He took her mouth again and kissed her hard as he pushed into her taking her body as he thrusted his tongue in her mouth.

Rory cried out as she felt his dick invade her. It didn't hurt exactly but it was alot bigger than his fingers had been and it was stretching her. She grabbed onto his arms for support as he pushed into her a little more. Shen tensed up as he knocked into her maidenhead. He stopped and kissed her for a minute.

Dean felt the final barrier knowing he was on the verge of breaching her. He knew she felt it too cause she tensed up again around him. He kissed her and said, "relax baby this is going to hurt and if you tense up its going to hurt worse."

Rory tried to relax as he kissed her again staying still as she felt him reach down and start rubbing her clit with his finger she moaned and bucked her hips a little almost breaching her.

Dean felt her relax and decided he'd better do it quickly before she tensed up again. He pulled back out and thrust hard into her taking the cry of pain into his mouth. He stopped for a minute and gave her a quick kiss on the lips. He said, "Are you okay?"

Rory laid as she felt the pain subside once Dean was all the way in. She heard him ask if she was okay but all she could do at that time was nod. Dean leaned in and kissed her as he grabbed onto her body. He started to move in and out of her for a minute it hurt but before long she was moaning again in pleasure as he thrust into her. She felt herself start to really relax as he started to move inside of her at a faster pace. She moaned as he hit her gspot again making her want more.

Dean moaned as he felt her walls pull on him as he thrust in and out of her. He would love to pound into her but he kept it slow and gentle as she started to move with him. He leaned in and kissed her agin on the lips. Rory said, "harder Dean."

Dean nodded and started pushing into her hard and fast as she grabbed onto his back he knew that she was liking it. He got up on his knees for better leverage and pulled her legs around his waist. She cried out at the change of angle but not in pain this time but pleasure as he thrust harder into her. He knew he was on the verge of cumming and wanted her to go over with him so he reached between them again and started to rub her clit. He felt her walls contract around him so he took her nipple in his mouth again and started sucking hard on it. She screamed as she came around him and he could hold back no more yelling himself as he came in her.

Rory felt like she almost blacked out for a second after they finished when she came to Dean was pulling out of her and pulled the condom off and threw it in her trashcan next to her desk. He pulled her comforter up over there bodies which neiter of them had seemed to think to do until now. He laid down beside her holding her with one arm under her head.

A/n: So there's the missing scene from Raincoats and Recipes I probably took liberites on how long they actually had before Lorelai actually came in the house but Dean doesn't strike me as the quicky kinda guy he seems like a gentleman.