Q&A: I had sex for the first time and failed. What should I do?

I had sex for the first time and failed. What should I do?

For a bit of background I am clueless when it comes to girls. I’ve never had a girlfriend before. I have never kissed a girl. I have never held a girls hand. I’ve always been very self conscious about my looks and never thought any female would find me attractive so I never really even bothered trying.

I have been hanging out with this girl for the whole summer. She went to my high school and moved before graduation. She is back for the summer and we have been hanging out nearly every day. Just getting food, smoking weed, watching TV. Normal stuff. She invited me up to her room to check out her current living situation etc. I sit on her bed as there really is no where else to sit. She is showing me some new music she downloaded on her computer and after a while she showed me some funny YouTube videos.

The whole time she is inching closer and being very touchy etc. My dumbass did not pick up on any of these signs. Like I said earlier I didn’t think any girl would be attracted to me. Especially not one this pretty. So it’s getting late and she asks me to spend the night, i asked here where i should crash. She said I could just sleep in her bed with her. So i laid down under the blanket and was about to go to sleep when she gets in my face, maybe an inch or two away. She puckers her lips and closes her eyes. I literally and stupidly said, “what are you doing” and she said “what does it look like” and I said “it looks like you are trying to kiss me” she started laughing and that’s when my dumbass realized what was going on. We made out passionately for maybe five minutes. (I got my first kiss hooray!) Then she began taking my pants off and gave me my first ever hand and blow job (hooray again). She said she is usually really good and quick but I was very nervous and lasted a very long time. Her jaw began to hurt and i told her not to sweat it. Not sure why but I could not finish for the life of me.

She is talking extremely dirty and is asking for it, I talk dirty back and tell her I would give it to her etc. Well i got a condom on and she got on her knees into the doggy position. I have never seen a vagina let alone been in one at this point. Keep in mind it is very dark. I couldn’t find the hole to make things simple. She tried to help guide it in etc but it was just continously slipping out. She is very tall so it put me in a very awkward position. I could hardly reach and when I got it in it would come out easily because for one I am not yall and for two she has a rather large butt and my dick really is not very big either. Also I couldn’t manage to get fully erect with the condom on.

I felt super embarrassed and just sorta stopped after a few more attempts etc. I apologized profusely and she said I was fine and that it’s ok. I told her I was sorry I couldn’t satisfy her and she said something along the lines of no problem. I could tell from her tone she was bummed out. She put her clothes on and I suggested maybe I just go.

I’m at home writing this now and I hate myself smh. I dont know what to do. If I should try again, if that would be too awkward, if she doesnt even want to try again or even see me. Worst part is she doesn’t know I’m a virgin. Should I tell her? I really am bummed out, I didnt think sex would be this difficult. At the same time I am pleased to finally have kissed a girl and received oral. Amazing feeling 🙂

Nessa’s response to had sex for the first time

For sure tell her that was your first time.   Had she known prior, she may have helped you a little more or not turned around so you would have to penetrate for the first time doggy style.  Not an easy position for a first timer!

Good ole fashion missionary would have been the way to go.  A good way to get her missionary is to go down on her, run your tongue through her vagina…maybe look at it closely and study it so when you try to stick your penis in it later, you know what you are doing!   And then you can add another first, the first time you ate a girl out.  Out of all those first times, that one is the most important in my opinion!  But maybe I’m bias.

Ryan’s response to had sex for the first time

I’m all about being open and honest.  If she talks with you again, let her know that was your first time.  Believe it or not, she won’t judge you in a negatively.  That’s kind of a guy thing.  Guys can be bullies when it comes to virginity.  She will probably find it adorable.  

Congrats on your first kiss, first blow job, first hand job, and the first time having sex.  Even if it was just a little penetration, that’s pretty much a grand slam right there.  It didn’t go as you planned, but that’s pretty much how everyone’s first time goes.