Off-topic Virgin Mindset

You could also work at getting her on top to start. That way she will put it in and you can see how it feels and what she likes. That will translate when you get on top or behind her so you know the motion she enjoyed.

The best way to get it in, in my opinion is to simply either play with her pussy and rub her wetness a bit around the lips (vagina). Or you can simply get some spit and rub it around your head (I do this all the time) and if you can imagine, just rub it up and down the vagina with pressure and you will feel the curtains open and find the opening. It is really so simple. The most important part is to make sure the area is wet so it slides in with ease. Wether it’s from her juices or your spit.

It also may turn her on even more when feeling you rub against her like that with your dick before putting it in.

Sounds to me like you are being your worst enemy. Just wait until you get laid dude, you’ll think back and be like “wow that was easy”.

Find an older woman, 35-45 and be real honest about your lack of experience and get her to teach you. She will be cool about it and totally love it.

Then you are an expert and can start nailing the gossipy young chicks, and much better than your friend does. ;)

My brother did this and turned into a lady killer. It’s a legitimate tactic.