Q&A: I Am Having Trouble Penetrating During Anal Sex

anal sex problemsI am a 19 year old male and have been sexually active since I was 16. It’s embarrassing, but to get it out of the way I just want to say, my penis has a very awkward bend that almost goes 45 degrees upwards right at the center of my shaft. I have had multiple partners and have always had trouble penetrating (vagina). Thankfully, most of the girls I have been with have been understanding and actually help me penetrate, by either grabbing my penis and putting it inside themselves, or guiding their bodies down onto me. I know it sounds dumb, but I have always been a bit nervous and haven’t really looked down while I am trying to put my penis inside a girl. I don’t know if it’s because I am shy or I don’t want her to think I haven’t seen it before. Well my current girlfriend is a bit more outgoing and experienced than me and has told me that she wanted to try anal.  When we tried, it was a disaster. Even when she grab my penis so she could insert it herself, she just can’t seem to do it. When I looked down, I felt like I was almost putting a puzzle together and just wanted to sit there and concentrate, which immediately took my erection away.  I also used a condom so I am unsure if this may be causing my problems with my erection. My curve definitely makes it hard, no matter how careful I am. Any help from either of you would be appreciated.  

Venice’s response:
This is an interesting question. I have a few suggestions for you and your situation.

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