So I 29m and a girl 26F I’ve know for probably 10 years had recently started talking again after things had kinda puttered out since I was living out of state but have since moved back. Things are going great, We’re having good times and me not only being terrified of messing something up and just being raised old school never really made any big moves. Now mind you I’ve made it very clear that I had very deep feelings for her and that those had been present since the day we met. So tonight we meet up to do a little workout, And then to go grab a drink afterwards. Things are going nice, We had two drinks, Grabbed some Taco Bell(Horrible idea but she wanted it) and had headed back to her place. We sat around and watched a little bit of TV while she laid her head in my lap and I just kinda stroked her arm and played with her hair in a gentle sweet way. She had fallen asleep and when she woke figured since it was late that we should both maybe go to bed and cuddle, She was into it which I was obviously excited about. So we lay there and I swore it felt like she was doing the little spoon booty wiggle on me, Got a little frisky and got shut down on that and immediately felt so stupid and my heart felt like it was going to beat out of my chest after she had said something to the effect of “we’re going to sleep, If you do that again I’m giving you the boot”. Fuck, Okay like I said felt really really dumb and stupid. Try to just move past it and just fall asleep. I had rolled onto my back because 1. I was hot as hell and 2. I just felt so stupid and that I had messed something up. This is where I begin to get beyond confused, I’m laying on my back still at this point, She puts one leg over mine doing basically like an open invitation if you catch my drift, Puts her neck basically to where my mouth is, And almost basically guides my hand south. Ok…. Confused and not wanting to misread again maybe 20 minutes before saying we’re going to bed and to not do that again, I started with something very simple, Kissing her on the neck which was welcomed, I put my hand back onto hers which was resting on her stomach and again it’s being guided south, Okay…. Confusion deepened, Hand shaking like a leaf both out of fear and excitement because again, Have had a major crush on her for years and never got anywhere near this. To keep it PG-13 even while moving at a literally snails pace everything felt wanted, Things are happening and then it felt like as she had her O moment, She said “okay that’s enough” confused I obviously stop, I guess my face revealed my confusion and she then said “This isn’t what I wanted” followed by a grunt and pants going on. Again, I moved SO slow because even though I was 99.9% sure I was reading her signals right I didn’t want to be wrong again. I’m really just kinda beating myself up here because my last relationship had a dead bedroom for about 6 months, And then this happened. So now not only do I feel like I messed up what could have been more with her, But my self esteem has found a new bottom. To clarify, Neither of us were drunk, Or even remotely tipsy. We had two drinks at about 9pm and this occurred at around midnight. I’m so confused and need some insight on what happened tonight, I’ve been crazy about this girl for so long and on top of the confusion and blow to my esteem, I’m also super freaking bummed out.

Apologies for the wall of text, On mobile.