A/N: I own nothing but the season 1-5 DVD's
Lorelai and Rory were sitting on the couch eating take out from Al's Pancake World. Lorelai puts her arm around Rory, they had just finished discussing the possibility that Rory might have sex with jess in the very near future, and whether or not Lorelai wanted to know anymore about Rory's possibly incoming sex life.
'Oh my God Mom, I don't know what im doing, I mean where are we going to do ummm. It! I don't want to lose my virginity in the back Of Jess' car" Rory said frantically.
"Woah, slow down there sister, are you really serious about this whole thing, I mean, is it really going to happen soon?" Lorelai asked.
"Yes, Mom im really really serious about this, I just don't know what to do."
"Okay Rory, I think the time has come to show you some stuff, now that youre going to be doing things that require this kind of stuff." Lorelai said as she got up and led Rory to her bedroom, Lorelai opened the top drawer of her nightstand and pulled out 3 condoms.
"Umm, mom why are you giving me so many of them?"
"Well, do you know how to put one on?"
"Yes, they taught us with bananas in like 7th grade health class…"
"Okay then, 1 for your nightsatand, 1 for your purse, and 1 for your pocket, I want you safe all around town, well maybe not in Doose's, but who would ever want to have sex in Doose's. As for your problem with location, I might be able to facilitate a location for you guys, even though its verging on bad mom behavior."
"Thanks Mom!" Rory said hugging Lorelai
"Take the box." Lorelai said, handing Rory the box of condoms" Lets go to bed"
"Sounds good to me" Rory said as she went to bed thinking about Jess. Lorelai had went to bed wondering if she had done the right thing.
3 hours later Rory was still awake and felt a bit thirsty, so shegot up to get something to drink, when she opened the door to her bedroom she saw her Mom sitting on the couch with a blank stare across her face.
"What are you still doing up?" Rory asked
" Are you telling me that you have been asleep the past three hours? Have you slept at all tonight?"
"Not a wink. Ive been thinking about the things that you told me, so I have to ask, why are you helping and supporting me in this decision?
" Rory, I remember when I was in your situation, and I think that you are responsible enough to do it, hell you were responsible enough at the age of three, but that's not the point, I just want you to be prepared for it so you don't pull a Lorelai."
Rory just nodded and hugged her mom.
"So when exactly can we do this?"
"Well I have a date with Alex tomorrow night, and I could definitely make it a late date, if that's not too soon for you." Lorelai said with a smile " I would probly get home around one o'clock in the morning, and Jess could spend the night if I can clear it with Luke without mentioning the sex thing."
"I don't know how to thank you mom."
"Just don't get pregnant and have a great time."
"I wont and I will, respectively of course, and you have fun with Alex.
"Oh, don't you worry about us" Lorelai said, smirking
"Mom, can I ask you something?"
"You can ask me anything Rory."
" I was just wondering how bad does it hurt the first time?"
"Well, you see, so much about the pain you've been hearing about really only has to do with how you do it and with who youre doing it. Of course the how youre doing it refers to the position that your using and the with who youre doing it, I don't really think you will have a problem with because it is obvious to me that you and Jess love each other and I don't think he would want to hurt you any more than you have to be hurt. My best advice to you is just take it slow and since im assuming he already has experience I think he should probably be on top and have him guide you until you get the hang of it. Does that answer your question?
"Yes it does, and I think I am finally tired." Rory said getting up.
"I think im just going to sit here for a little while longer and think."
"Is there anything you want to talk about?" Rory asked.
" Oh No, you go to bed, I was just thinking about my first time… it was awkward and I didn't know what I was doing, but even with all of that, Chris made it feel absolutely perfect."Lorelai said with Rory listening intentively." Chris was my first real love, he was my escape from a life I did not want for myself. I never wanted you to have to escape from your life, I wanted you to choose what you wanted. I just want you to know, you don't have to be afraid to tell me anything."
"Thanks Mom, for everything."
"You better get to bed now, you have a big night tomorrow" Lorelai said
"Yeah I guess I do, good night mom, I love you"
" I love you too sweets." Lorelai said as they both go up and went to bed.
A/N The sex will come in the third chapter, im trying to take things slow
