Pencil Dicks Short Vaginas, Herpes, and Sugar Daddy Issues

Follow me on Facialbook or Twitter my Clitter!

Have a question for me? Email:


Dear Ms. M.,

This is maybe a little tamer than the questions you usually get. I am a young, 19 year old guy who has been having problems with fit recently. When I first lost my virginity at 16 there were no problems, but with each consecutive girl I have had sex with, I have a harder time getting it to fit in. I have slept with four girls in total now. I think maybe I have just grown down below since I was 16, but maybe I am just doing something wrong. It is more of a depth problem than width usually, and even with lube and lots of foreplay, for the girls it isn’t solved. It is really frustrating not to be able to go all the way in and I was wondering what could help fix this. It is stopping me from enjoying sex as much, especially since the girls find it painful, and having my partner enjoy it is paramount to my own enjoyment as well. As young teenager I never would have thought that I would have wanted a shorter penis; I don’t even think mine is that big (actually I am quite sure). Is it possible these girls just have short vaginas? Is this a common problem? Anything you can tell me would be useful, thanks!

-In Too Deep

P.S.: Not sure if this is inappropriate to include, but my penis is only 18cm (about 7 inches) in length.


I am very pleased to hear you are using lube and engaging in lots of foreplay. I am even more impressed to hear that having your partner enjoy it is paramount to your own enjoyment. You are a wonderful example of a sexually conscious evolved male. Kudos!

When I read your email, I was reminded of a guy I used to date nicknamed Tripod, because basically, it was like a third leg. We didn’t need lube (I get very wet naturally on my own), but he always spent a good 30+ minutes on foreplay. When he did finally penetrate me, I was so eager and hungry for him, he would basically stay still and I would grind my way to greater and greater depths. He was 11+ inches. Only once after a three-day trip we took together, did I feel sore from all the sex.

That being said, I’ve also had sex with guys much smaller than Tripod and smaller than you, yet some of them had this notion that pounding me hard, fast, and forcefully was the way to magically and instantly make me cum. So you see, it’s not necessarily the size of your cock, but how you work it.

Consider the motion in the ocean. Are you going bang bang bang, hammering away? Or, are you slowly entering her, teasing her, and listening to her body? Are you allowing her to suck you inside of her between her legs, because she’s so hungry for it, she needs it? Or are you pounding her?

Hardcore porn tends to teach younger guys the wrong way to do it. Sport sex can be fun on occasion, but remember, porn stars are PAID TO ACT like they’re into it; it’s not a fine example of how to truly please a woman. Go in slow motion, to where you’re driving yourself crazy. Try not to stick the whole thing in there in one big jabbing force.

You can also try switching up the angles. Let her be on top and be the one in control. Or, if you’re on top, go inside of her, then put her legs together and your legs around the outside of her legs. You can also try putting a pillow under her bum to vary the angle.

More importantly, remember you’re only at the beginning of your sexual pilgrimage. If you’re having sex with girls your age, they are likely as new to sex as you are. Odds are, they don’t know what they’re doing yet. Keep trying: patience, perseverance, and practice are key ingredients. Maybe hook-up with an older or more experienced gal who can give you more relevant honest feedback.

Good Luck,

Ms. M.


Ms. M.,

I found Valtrex in my boyfriend’s bathroom cabinet and his name was on the prescription label. When we started having sex, he swore to me he didn’t have anything so we’ve been having sex unprotected for nearly six months now. I’m so pissed I want to kill him, and definitely considering breaking up. A friend said I probably will not get herpes so long as we don’t have sex when he has a visible sore. Is this true or do you think I have already gotten herpes? I’m so mad he lied and didn’t tell me.

-Betrayed In Boston

Hold your horses there, Betrayed. You’re jumping to conclusions and living in the heat of emotion. You haven’t even communicated with your partner about this find, yet you feel your relationship is at a level where it’s okay to have unprotected sex regularly—doesn’t add up.

If you were in a great relationship, you would calmly and coolly explain you were searching for Advil or toilet paper or toothpaste and noticed the bottle of Valtrex with his name on it. Then you would ask, “Is there something I should know? Are you okay?”

He hasn’t necessarily lied. Valtrex is used to treat alpha-herpes viruses, including herpes simplex viruses 1 & 2 (what you’re worried about), plus varicella zoster virus, which causes chicken pox and shingles. So basically, it’s possible he has Valtrex because he had a bad case of shingles, which is not an STD. While they all may be of the same viral family, it’s important you remember the varicella zoster virus that causes shingles does not and will not cause herpes.

If he does have herpes, then yes, it’s possible you have contracted it. It’s a virus that stays dormant in the body, so until you get your first outbreak, you won’t show any symptoms and you can still possibly infect partners. If you have no symptoms but would like to know if you have contracted the virus, you can opt to take a blood test or an antibody test.  Here’s some information on test types, so you can determine which might be best for you.

If you do in fact have the virus, it doesn’t necessarily mean he was the one who gave it to you. In the USA alone, one in four sexually active women and one in five sexually active men have herpes. Additionally, among the estimated 50 million Americans who have genital herpes, 90% don’t know they have the disease. One last thing while we’re on the topic: those blisters on people’s mouths everyone calls “cold sores” are actually herpes simplex type 1. Don’t let them fool you!

-Ms. M.


Dear Ms. M.,

I have been in a relationship with a man who started out as my sugar daddy. He pays my rent and all my college expenses and gives me spending money. We go out to nice restaurants and also have occasional threesomes with other girls, which I enjoyed until recently. You see, I’ve developed feelings for him I can’t explain. We have a huge age difference and looks wise, it doesn’t make sense. I’m afraid to tell him because if I do, he might end the relationship and cut me off. But at the same time, I hate hearing about his mean nagging wife, their family vacations she organizes, and her redecorating plans of their huge townhouse. I deserve what she has, not her. He also has three kids, so I doubt he will leave his family to be with me. What should I do?

Falling for your sugar daddy is like being a drug dealer and gettin’ high on your own supply. You just don’t do it! You got into this situation for money, and at best a friendship—not love.

Most importantly, you do not deserve what his wife has, you deserve better. You deserve a man who wouldn’t cheat on you if you were his wife (unless you were both cool with an open marriage). You deserve a man, who, when faced with a sexless miserable marriage would communicate, seek therapy, or divorce. That is a real man, one who makes a valiant effort, BUT who is also true to himself. If a man is not true to himself, how could you ever expect he remain true to you or your marriage? You may be thinking he wouldn’t cheat on you if you were his wife, but what about in 20 years when you get old and boring? Men have sugar babies for the same reason dogs lick their balls: because they can. And yet, a lot of them have a profound need for affection, sex, and to feel needed by someone, but ironically don’t have the balls to leave their wives who aren’t fulfilling their needs.

He’s not going to leave his miserable nagging wife. You are selling your long-term self short for some cash and the façade of security; that’s not cool. Personally, I think it’s fine to have a sugar daddy at this point in your life. In fact, the experience will hopefully provide you with some insight to men, bad marriages, and how powerful you can be as a female (see Erotic Capital). But once you’re out of college, it’s imperative you make your own money and provide yourself with security, or you’ll wind up being no different than his wife.

The greatest thing that could come out of a long-term relationship like this, besides the obvious mutually beneficial arrangement, is a profound lasting friendship. One day you may not still have sex and you may not be supported by him financially, but you will hopefully always be able to call each other up and shoot the breeze with ease.

You need to get over your romantic feelings for him. Find another guy, ideally hotter and younger to crush on and distract yourself; have lots of sex with the young stud. Take a small break from the sugar daddy, go on a trip, get your groove back like Stella. But whatever you do, DO NOT, I repeat DO NOT, tell your sugar daddy you have feelings for him. It will make life much more complicated for you both. Let it be! He likes being needed, but not being possessed or nagged the way his wife treats him. You are his fun escape from the world; remain so, and remain in your current lifestyle.

You could also consider getting a job and taking out student loans like the rest of American students, but who wants to pay off loans for the rest of their life? Maybe just find another sugar daddy. Affection-starved, sex-starved men in miserable marriages are extremely easy to find. Apparently, there are tons of girls at NYU with them. Screw the expensive costs of college education in this country, and screw the man … oh wait, you are.  😉

Much Love,

Ms. M.


Follow me on Facialbook or Twitter my Clitter!

Have a question for me? Email: