Okay. Here's more or less how it went down.
Part I:>Didn't get much sleep the night before. So I was pretty tired when I went to get her.
>I picked her up. We went to the Indian restaurant. Had really great food and wine.
>I thought she would be a bit more talkative this time around but eh... she's still shy/anxious.
>After dinner I decided to go to a bar downtown to loosen myself up a bit since I was getting kinda antsy. She said she didn't need anything drink at the moment (something to do with the wine + her anxiety medication seems to make her more drunk.)
>The bar I wanted to go to was packed to the gills. So we went to a coffee shop next door. I got a pumpkin spice latte to wake myself up a bit.

>After I got my coffee we went outside and sat at table and just admired the beauty of our surroundings. We kissed.
>We got back to my car and headed back to my place.
Part II:>We get to my place.
>I go to my fridge and down a bottle of cider while she was chilling on my living room couch to calm my nerves.
>I go back to the couch.
>I load up Netflix on my TV, lower the volume, and we just cuddle on the couch and talk for a bit.
>One thing leads to another and we start making out. Then I start kissing her breasts. Then we're essentially dry humping each other.
>She suggests we go ahead and go to my bed. I agree.
>She lays in my bed. I start stripping. I (having a foot fetish) took her socks off and got a footjob from her first to get myself going. That was kinda weird but her soft soles felt good on my dick.
>She strips down. We make out some more in my bed.
>I give her the go ahead to start sucking me off. That felt pretty good except for when her teeth nipped my dick a little bit.

>After that I try to put on a condom but my dick was deflating fast due to nerves (this happened several times). Whenever this happened I just decided to start making out with her some more and just jerk myself off.
>Eventually I get a condom on and I decide to have her ride me first. That was fairly enjoyable and easy for me (seems like it's harder to cum that way).
>We then switch positions and I'm fucking her in the missionary position. About ten or twelve thrusts in I cum.

>I take off my cum filled condom and chuck it the trash. We take a little break and just cuddle to each other for a bit.
>We make out some more and then she suggests that I finger her. I oblige.
>I do that for some time, lick around her clit as well. Vaginas definitely taste... odd.

Anyways, she seemed to enjoy that.
>After all of that we decide to go back to my couch and watch some more of The Office on Netflix. She asks if I feel different now after having sex for the first time and I told her "Totally. I feel like a whole new world has opened up for me." or something along those lines.
>After we finish watching an episode of The Office we both decide to go to bed to sleep since it was late and we were both pretty tired.
Part III:>I really enjoyed having her in my bed. Especially on a cold December night.

>Basically we just cuddled up to one another and fell asleep.
>We eventually both wake up around 7am the next morning, got some water, and washed out our mouths with Scope.
>We start making out again and I ask her if she's down for another round of fucking. She says yes.
>I have her riding on me first. And we switch around and I'm fucking her in the missionary position again. I'm able to last much longer this time.
>I would kinda do a bunch of thrusts. And stop (to prevent myself from cumming). thrust some more. stop. thrust some more again. stop again.

>I have no idea how long I was doing that for but eventually I stopped and didn't cum. TBH, I like the sensation of the thrusting over the sensation of cumming in a condom.
>We decide to take a shower together to wash off our post-sleep & post-sex filth.
>After that we both sit on my bed in nothing but our towels and she asks about my thoughts about us and where we shall go from here. I acknowledge that we're kinda in the dating phase of our relationship right now and I'm totally fine with us not being exclusive yet BUT that I would be definitely open to being exclusive with one another after some more time has passed and we have gotten to know each other a lot better. She seemed okay with that answer.
>Then we put on some clothes, watched a couple of episodes of It's Always Sunny, and ate breakfast at Waffle House.
>On the drive back to her place we talked some more and I talked about how I did like her a lot, how close I was from taking a break from Tinder because of all the nonsense I had to deal with up until this point, and that I was kinda tired of the whole "pursuit" and would likely want to get into some sort of relationship with her. She again reiterated that she definitely thinks I'm cool and fun to hang around with.
>I get to her place, I wish her a Merry Christmas, we kiss each other goodbye.
>I drive back home and take a nap.
I'm most likely going to text her tomorrow to again wish her a merry christmas and ask her when she knows her schedule for next week so we can hang out again.
But yeah. *whew* I'm just glad I finally have this "virginity" monkey off my back.