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Dear Ashley, a weekly sex column in which Sex Expert Ashley Cobb answers your most intimate questions. Nothing is off-limits!  Have a sex question, Ashley, “Your Favorite Friend In Filth,” has an answer. For questions on sex, email Ashley at


Dear Ashley, 

I am a 59 year old white man who recently started seeing a 45 year old black woman.  I have never been with  a black woman before and she has never been with a white man. We talked about oral sex and she is excited about me performing cunninglis on her as well as I. But I am a little worried about sex because I am somewhat small. How should I initiate sex with her. Please advise and give tips? I want this to be memorable.


Dear Mr. Smaller Package,

I have both good and bad news. The good news is as the saying goes: “It’s not always the size of the boat but the motion in the ocean” Sex can still be pleasureable with a smaller penis. With the average penis size only being five inches—you’re in good company. Most of the pleasure points on the vagina are around the vaginal opening and 2 to 3 inches inside at the G-spot. Which means technically you don’t have to be King Ding-a-ling to make a woman cum. You just need to know how to work what God gave you. And if she’s like me she might not enjoy a third leg anyway. I’m not sure who put out the rumor that  the bigger the dick, the better the sex but that shit is “Fake News.” 

Good sex is more about skill and knowing your partner’s pleasure points than it is about dick size. I’m sure there are more than a few women who like myself have been bamboozled, hoodwinked and led astray by a larger penis only to have to reach for her vibrator to finish the job. If you are confident in your skill set then lead with that. Do what you know works. Also pay attention to her body language, breaths and moans; these will tell you how well she’s enjoying the interaction.

Now for the bad news: If she is a size queen, it’s a dead deal before it begins. Size queens are women who love big dicks! They love the pain and extra full feeling that only a well-endowed penis can provide. However, even if she is a size queen most women love head. Good head can almost make you forget about dick. So my advice is to make sure you eat her pussy from the front to the back. Eat that thing so good you make her call on religion. The key to sex when having a small penis is to make her cum as a many times as possible before penetration, so by the time you’re ready to stick it in she’ll be on such an orgasmic high, it won’t even matter how small your dick is. So when in doubt–eat her out!

Ashley Cobb is the millennial microphone that brings the conversation of Black women’s pleasure to the forefront. Creator of digital platform Gossip And Gasms, her work and words have been featured in Cosmopolitan, Men’s Health, Shape Magazine, Business Insider, and Huffington Post. Follow her on Instagram and Twitter via @sexwithashley

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