Hey everyone, First time ever posting on here. First, I just want to say thanks. I’ve been a reader of the site for a long time even before I was out, and while there were many days I thought I would never be brave enough to come out of the closet, these posts inspired me to finally build up the courage to do so. So I didn’t come out until I was 27 (I’m in my early thirties now). Long story, but I lived in a rural town and was scared and nervous about it. I live in a larger city now. Even though I’ve been out for several years now, I am still a virgin. I’ve never even kissed a guy (or girl) before. Crazy, I know, and trust me, I really want it, but I started a new career when I moved and sort of pushed my personal life to the backburner, but it bothers me that I put in all of the work building up the courage to come out, but have yet to still enjoy any of the physical and sexual perks of that. Jumping forward, I’ve dipped my toes into the online dating world, and I’ve been speaking to a guy I really like and that I think I would really like to be my first. He’s a bit older than me, and I like the fact that he is older and more experienced, and I feel like I’ll be more comfortable with him taking control and guiding me a bit. I definitely want to bottom for my first time, this is the way I’ve thought about it and planned out for so long now. I read the sticky thread about this but I have a few concerns/questions that I hope you guys can help with. First, I know it’s a crazy question, but any tips on kissing? I don’t want to be terrible at it the first time lol. Onto the sex part, any tips for oral sex? I want to make sure I do a good job for him, I have some idea of what to do but any tips I’d appreciate. Second, onto the actual anal sex, what is the best way to prepare myself? Should I not eat certain foods or things beforehand? I’ve never even used a finger for that so this will definitely be something new for me (I’m not sure how big he is). What I would really like position wise is to be on my back so I can be looking at him, but I also want to do what’s going to be the easiest and most comfortable and enjoyable. I really want to be able to take all of him on this first time and be able to really enjoy that and this experience that I’ve been waiting on. I’ve purchased lubed condoms and lube as well, do I need anything else? My main concern is just to make it special for not only me but also him, the more I know he’s turned on, the more I’ll be turned on. Any tips or advice is greatly appreciated. I know saying that I want it to be perfect is a high bar to set, but I do want to it be really great and for us to both be very happy at the end. Also, I’m hoping our relationship will continue, and I’d ideally like us to have sex on a daily basis (with him always topping and me always the bottom). Is there any tips on this as far as me needing to do anything differently to be prepared to do it so regularly? I know this is a long post but I sincerely appreciate any help you guys can provide. Thanks again.