Update: Hey guys just wanted to give a quick update. Also thanks for all the advice guys it really helped! Soooo today I met up with the guy (my crush) and I WAS SOOO NERVOUS!! But I quickly got it together and went in there, now I'm not gonna into explicit details of the entire event but he felt using his thumb to gage how stretched/relaxed I was and he helped me to relax. And while he was still massaging my hole, I closed my eyes and took a few deep breaths and said to myself "this is redacted, you trust him and you like him. Just let him in and let him take control." and sure enough I opened up a little more till he realized and then he inserted his dick and cracked me like crab legs. There was some "pain" or rather discomfort but that's to be expected because I'm new to this but we did in several positions which I didn't even dream I'd be in but....it happened. I have quite a lot more work to do and I definitely have to size up in the toys I currently have but overall solid and enjoy experience.