Ask Her: Overcoming a Small Penis

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Dear Bailey,

smallI have a small penis.  There is no denying that, and I fall well below the national average. I’ve heard the cliché it’s not the size that matters but what you do with it, but I am very insecure about it.  Is there anything I can do to make sure my woman is satisfied?

-Tom T, Smallsville


The short answer (no pun intended) is if penis size mattered to everyone, lesbians would be miserable. Yes, there are many women who say that size matters (and a relationship with those women is probably not going to work out for you), but there are just as many women who not only don’t mind a small penis, they actually prefer it.

The problem with attractive guys with large dicks is they know they are attractive guys with large dicks. They often get lazy because they can, and feel they can rely on their looks and penis size during sex. Women tend to swoon over them for a while, and they have never had the insecurities that small penises can bring. Their attitude is “It’s not what you do with it, it’s the size that counts,” and this doesn’t serve them well when it comes time to impress.

For many women, a small penis gives more pleasure than a big one, plus there really is a great deal more to sex than just penetration.  Most of my readers know that I’m a very sexual creature, but many don’t know that I’m your classic frying pan in bed: you need to heat me up before you stick the meat in.

Some tips to remember:

Focus on Foreplay

Your small Johnson doesn’t mean shit when she is riding your face. Since you have a little guy, make sure you prolong the foreplay until she is ready to pop. If you are dating a multiple orgasm girl, give her a few before you even consider having sex.  If she’s prone to only one orgasm, make sure she has one before you have intercourse.

Just remember: do the things that get HER hot.  For me I like to start with a long kissing session, followed with playful biting and wrestling, leading to me being punished for being the naughty girl I am… but this kind of foreplay is not always appreciated. Find out her preference and do that. Dirty talk, spankings, and talking about fantasies are all good ways to get her motor revved up.

The Little Man in the Boat

Prior to intercourse, you’ll want to spend as much quality time with her clitoris as she can handle. Whether you do this via oral sex, toys, or manual stimulation is really according to her preference, so make sure she climaxes at least once before you move on to penetration. Make sure you take direction too.  If you are licking up and down and she wants some side to side action… do it.

Big Positions For Little Dicks:

Doggie Style

When performed at the correct angle, the doggie can make even the smallest penis feel quite large. Position her so her head and shoulders are on the floor or bed, with her butt raised up. For an even better angle, she needs to arch her back and squeeze her thighs together.  This is probably the sexiest small penis position.

Little tip: (pun intended) Lean forward during penetration, and maintain a lot of body contact.  This makes it intimate, allowing her to feel connected as well as stimulated.

Antelope Style

This is a nice variant of doggie style but set in the Savannah  Just kidding.  I’m seeing if you were paying attention. Jokes aside, this is a great position. You both kneel on the floor and lean over a chair or couch. Open her legs from behind and enter. This leaves her hands free to self-stimulate, making your job easier. Remember to spice it up by adding spanking, hair pulling, and light choking.  Super hot.

Snake Style 

For this sex position, you’ll want your woman lying flat on her belly with her legs closed. Slide a pillow beneath her hips until her bottom arches upward. Keeping your knees bent, straddle her hips while maintaining an upright position, gently spread her thighs just enough to allow penetration and slide your way in. For a tighter fit, hold her thighs together as you penetrate her. This is also an excellent position from which to administer some hot spankings.

Rabbit Ear Style

Lay your woman down on her back, spread her thighs and draw her legs up until her knees are close to her ears. Slip a pillow under her ass (better for small penis entry), and when you penetrate her, it will feel as though you’re filling her completely. Use your arms to hold her knees in place.

While having a small penis might carry social stigma, the reality is any penis size can make a woman orgasm as long as the guy pays special attention to her needs. Yes, you may have to use toys or your fingers to stimulate her during intercourse, but so what? That’s often necessary with a large penis as well. Your penis is not the only part of your body you use during sex. Use everything you have and make her pant for more. Foreplay is what matters most, and an amazing orgasm from a man’s tongue will usually win any woman over.

If all else fails, just shove it in her butt.  Watch how big it seems to her now.

Have Fun!




Bailey Ryan is our resident relationship expert and senior editor. She is a syndicated columnist and the author of “Ask Her”, and has been a guest on several radio and TV broadcasts, and has been recently been cast on a TV show and in a movie. She specializes in sexual behavior, relationship advice, and off-road jeep tech. Feel free to send any questions your heart desires to the magazine or Bailey directly, either on twitter: @chirebailey or email: