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.

Positioning. Even if a guy has an “ideal” penis, i.e. perfectly straight with no outrageous angle, that also sits nicely over clean, hairless balls, which smell like cherry blossoms, that also sweat salted caramel flavored fluid, sex will be comfortable as long as they’re positioned in a way both people are comfortable. Try different positions, particularly those where she is slightly elevated. This may help because she’ll have a slight height advantage as far as lining up your male to her female parts.

What worked yesterday may not work today. I say that because sometimes Ryan and I find a position that we love and end up in that position every day for a week. Once it was one leg over his shoulder while the other leg was flat on the bed. It was great because the angle was perfect, it rubbed on my cervix smoothly without being too painful, and he used gravity and my leg to create an ideal momentum combination that conserved stamina. Then one day, his penis was harder than usual and every time he thrust in, my lower stomach would be in pain. Ryan senses this because I tense up and I start to lose my wetness as the pain gets too overwhelming.

However, what’s just as important as positioning is learning your body. I discovered so much about my body in the past five years that I didn’t know could happen: the different ways I orgasm, feeling my body heighten, noticing every change before, during, and after a climax. I learned all these things and by doing so made our love life that much better. Instead of “going through the motions (of sex),” it became an experience. Surely you can’t expect your partner to do all the work for you. Find out what the best angles/positions are for her so that you can help. Help her to help you! Learn how to do it and practice. I supposed it’s like putting on a condom: by the time you’re done, it spoils the mood and you get soft.

Eventually you will find a permanent female partner who will adapt to your body, penetration style, and/or position requirements. You’ll feel so comfortable with her that you’ll be able to move and feel without saying a word to each other. At that point, you’ll be inside before you even get a chance to get soft.

Once you figure those things above out, then move on to trying anal sex.  For now, my advice is to stick with vaginal penetration, learn your body, learn your positions, and learn to penetrate a woman without needing her to guide you in.  By the way, a man looking down as he puts penis inside us is sexy as hell, not something to be embarrassed about. I don’t shave, have it pierced, and keep it clean and shiny so it can be ignored. Look down and enjoy your girl’s kitty, it’s yours for the next hour or so.


Ryan’s response:
Moving into anal sex when you haven’t mastered the basics of how to penetrate your penis into a vagina doesn’t seem like a good idea.  It actually sounds dangerous.

Are you a risk taker?  If so, keep reading because I do have some suggestions.


First thing you can try is to stand on your head with your pants pulled down (or up, depending on which way you view the illustration). Make sure you are erect and your 45% angled penis is perfectly in place.  Have your girlfriend/wife in front of you on all fours with her ass up in the air. Now, guide your penis down into her ass like an airplane refueling in mid flight. This may be a bit difficult, but the risk is worth the reward.

2015-11-04 (1)Another technique suggested to me by Venice is the trampoline technique. This maneuver needs to be done precisely as any wrong movement can be critical to both of you. First, you will have to again be erect with your pants down. Your girlfriend/wife must be nude and jumping on a trampoline. I’d suggest that she jumps close to the edge so when she jumps off ass first onto your penis, she doesn’t hit the edge of the trampoline (think Greg Louganis) and do a backflip, possibly kicking you in the face. Her dismount must be perfect and she must stick her landing, literally.

2015-11-04 (2)The final technique probably isn’t possible at your skill level, but if you master the first 2 techniques, you might as well go for the Superman. First, you will need to either find a costume store or make your own Superman cape, as this is extremely important for the role-play factor. Once you have your cape on, make sure you pull your pants down and have an erection. Now, stand on the edge of the bed while your girlfriend/wife is on all fours in front of you.  Dive off the bed full speed and put your hands in the Superman flying position. Although you are not really flying, if your jump is good and she is at the right distance, you can literally mimic the concept of flying and glide right into her ass with your cock. This is a perfect penetration technique for a 45% degree angled cock.

If you don’t like these techniques or they seem to be a bit too extreme, you could just go back to having normal sex and take your time to learn your own body. Nothing is more dangerous than a samurai that doesn’t understand how to use his sword.

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LMFAO Ryan??