Category: Ask Her

Ask Her: Why Smart Girls Are Better In Bed (and how to pick one up)

6016447741_480492d765Dear Bailey,

I’ve always been attracted to smarter girls, but I feel intimidated by them for some reason, and always end up dating girls that are shall we say… less intelligent.  How do I approach smarter girls without looking like an idiot?

Karl D. –Los Angeles, CA

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Ask Her: Bend Over Boyfriend; The Truth About Pegging

4fc4c4f2cb15fDear Bailey,

My wife wants to do me with a strap-on, and although I’m not REPULSED by the idea, I am afraid it will emasculate me in her eyes in some way, or make her think I’m gay.  What should I do?

Sam S. –Hollywood Ca Read more

Ask Her: Going Limp with the Girl on Top

150b1f8357255549c0a57b89ed3f4916_MDear Bailey

I feel I have an amazing sex life, and I’m very attracted to my woman, but when she rides me cowgirl style I always go limp. Is there anything wrong with me?

-Greg A;  Avalon, CA

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Ask Her: Overcoming a Small Penis

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 Read more

Ask Her: Why Nice Guys Are Awful To Date

Dear Bailey,spotniceguy

I’m a nice guy.  I was raised to treat women with respect, be agreeable, never talk down to them, etc.  I also find I am perpetually single.  My relationships last quite a while, but I always end up getting dumped after a couple years, and it usually takes me at least a year to find another girlfriend.  Is it really true that nice guys finish last?  What am I doing wrong? 

James K. –Riverside, IA Read more

Ask Her: Should Cheaters Come Clean?

cheaterDear Bailey,

I’ve been with my GF for 3 years, and we are very happy.  In fact, I even popped the question last November and she said yes, which makes me feel worse about this.  I went out with my friends to a New Years Eve party and ended up wasted and woke up naked in bed next to a girl I didn’t recognize. I don’t know or really like this girl, but the guilt has been eating me up since New Years and I think I should tell my GF.  I don’t want to break up, but I think she should know.  What do you think?

Kevin -Dallas, TX

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Ask Her: Spice Up Your Sex Life

hotsexDear Bailey,

My husband and I have fallen into that sexual rut that I’ve often heard about.  I still love him very much, and we still have sex once or twice per week, but its getting really boring.  Do you have any simple ideas that will spice up our marriage?

Gloria S, -Chino, CA Read more

Ask Her: Public Sex

Dear Bailey,

My girlfriend has a kink that I’m uncomfortable with. She can only have an orgasm when she is on camera or when people are watching her. She also says when she masturbates, she pretends to have people watch her, and in the past has used a webcam so people could watch her. In all other ways she is amazing and normal.  What can I do?

-Anonymous, Southern California Read more

Ask Her: Can Any Girl Learn to Squirt?

O Face

Dear Bailey,

My ex-girlfriend always squirted when she had an orgasm, and my current GF wants to learn how.  If a girl has never squirted, can she learn how to do it?

-Jason M; Rancho Cucamonga, CA


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Ask Her: Why Do Women Think Rape Fantasy is Sexy?

bondageDear Bailey,

 My wife recently came to me and told me that she hasn’t been sexually satisfied in some time.  She says that she can only get excited if she is thinking about being raped, and now wants me to “rape” her.  I’m a little hesitant, as I’ve always considered violence against women to be repugnant. What should I do?

 Jeff H. –Manchester, England Read more