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Dear Ashley,

I have a question that’s personal and I figured I’d ask for your advice… I’m a 40-year-old virgin and while I have had oral sex I haven’t had penetrative sex. I wanna have sex, but I’m nervous that it’ll hurt. I do get turned on by certain things and I have masturbated (with a pillow). Where should I begin in my search to have my first penetrative sex experience? I’m not in a relationship but I wanna have sex. I do have one friend in mind but he doesn’t know (obviously) and would probably never think I was a virgin because we flirt a lot and text things back and forth, like pics, he probably wouldn’t even believe me if I told him. He’s 34 which shouldn’t be a big deal… but yea.. Lol. Thanks for taking the time to read this and thanks for any advice/suggestions.


Dear 40 Year Old Virgin,

First of all, let me say how commendable it is that you’ve managed to not have sex for this long, because honey, Ashley couldn’t do it.  Due to the fact that you’ve waited this long, I’m assuming for religious reasons, it’s probably best that your first penetrative sexual experience be with someone you have a connection with.  That being said, I think your friend with whom you’ve already been flirting would be an excellent candidate. As your “Favorite Friend In Filth” I am going to give some pointers on how you can approach this topic with your friend confidently without it being embarrassing.  

You stated above that you guys are already flirting, texting and sending photos that I assume are nudes or at least partial nudes. This is a great sign that indicates to me he already has interest and finds you sexually attractive. My first piece of advice would be to send a very sexy nude with the following caption, “What would you say if I told you that I wanted to have sex with you?”  This question is going to get a response, don’t worry. It may catch him a little off guard but he will respond. The next step depending on your level of comfort could happen over the phone or continue via text. Once, he responds to the first question you tell him that before you guys can have sex you must tell him a secret. Now, of course, the secret is that you are a virgin, but instead of saying, ‘I’m a virgin, surprise!’  I want you to share with him how you really enjoy the connection thus far and feel ready to explore the next level, but because of (explain your why here) you’ve never had penetrative sex and would love to share that experience with him. 

Now, to be completely transparent this could go one of two ways: he could be flattered, understanding and honored to go on this journey with you or he could decline. No matter the outcome you will be okay either way.  If he declines, no biggie you have lost absolutely nothing and you try again with the next love interest. You will find someone who will be honored to share this experience with you, you must remember that! But because you are the whole entire sh*t, he would be crazy to say no, so when he says yes, you need to be prepared.

A lot of women’s first time was either painful or not the best experience overall because we are not taught what to expect or how to prepare. It’s important to remember to have him be gentle and go slow. Take your time, it’s not a race— only go as far as you feel comfortable. ALSO USE LUBE! I can not stress this enough, lube makes sex 100x more pleasurable. Invest in some silicone lube, I personally recommend Momentum Intimacy, a Black owned company. Even though this will be your first penetrative experience it’s still important that you take control of your pleasure, which means being vocal when something doesn’t feel good. Sex is not supposed to be painful.  Foreplay is crucial in helping women prepare for penetration. I recommend the 20/20 rule. Have him spend an average of 20 minutes above the waist, this can include fondling the breast, kissing, touching etc. The next 20 minutes should be spent below the waist, stimulating the clitoris, rubbing the thighs etc. I also suggest that he slowly begins to penetrate you with his fingers one at a time, to prepare for the main event. Again at any time if something hurts, doesn’t feel good or if you change your mind, STOP! This experience is about you. Remember to take your time, breathe, relax and enjoy the pleasure. 


Ashley Cobb, is the millennial microphone that brings the conversation of Black women’s pleasure to the forefront.  To submit your sex questions email her at

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