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Putting A Ring On It


Name: William
Age: 30
Location: UK
Hi There
I am new to this scene, and I have very little experience in anal sex and I am seeking your help and advice. I am a top but I have a problem keeping my dick hard or staying hard during anal sex. I find it harder to fuck an ass compared to fucking a pussy. Here is the problem: Once I get my dick hard, put on a condom and start fucking, my dick sometimes goes soft on me. Is that normal? How can I keep my dick hard long enough in the ass to enjoy the fuck? Sometimes even when my dick is hard, I find it hard to penetrate an ass. I use lube, so what am I doing wrong? People in gay porn can fuck and fuck like there is no tomorrow. I want to enjoy anal sex too!! Any advice? Please let me know if there is anything I can do to improve in this area?

Boy, you’re in luck, William! One of my most popular tutorials, Finessing That Ass Fuck — A Tutorial For a Top, is waiting for you.  Check it out! It will answer a lot of the questions you have about butt fucking. You should also know that this is the companion piece to my tutorial for ass fuckin’ bottoms handsomely titled: Liberating The B.O.B. Within. Don’t know what a BOB is? No to worry, all will be explained.

gettin it from behindBut before you disappear to do your homework, I’d like to address one of the specific issues you raise, about keeping your dick hard while fucking. You are right to point out that fucking an ass (male or female) is different from fucking a pussy. But regardless of what hole you’re invading, a nice hard stiffy is essential.

Are you familiar with a cockring, William? If not, I suggest you acquaint yourself with these amazing low-tech wonders. Here’s what you should do. Mozie on over to the Dr Dick’s Sex Toy Reviews site and search for my tutorial, Cockring Crash Course. (The search function in the sidebar will assist you.) Prepare yourself to be sorely amazed at the variety and functionality of these little devils.

Cock rings can create larger, firmer erections. Since blood flow enters your dick through arteries deep inside your dick, and leaves it through the veins near the surface of your tool; wearing a cock ring can help to keep more blood inside your dick shaft. And as all you rocket scientists know, blood is what causes erections in the first place. Also some men claim that wearing a cock ring intensifies their orgasm.armour up04

And while you’re on the sex toy review site, use the CATEGORY pull-down menu in the sidebar and look for cockrings. You’ll find it under the last heading, Sexual Enrichment. This will bring up all the cockrings we reviewed, and there’s a load of ‘em, don’t cha know.

I recommend the flexible and/or adjustable cockrings. These are generally made of stretchable rubber or leather. For the more daring there are the metal variety. These may look pretty, but they can be a bitch to put on and to take off. Here’s how ya do it.

  1. Pull your ball sack through the ring first.
  2. Follow this by popping each of your balls through the ring one at a time.
  3. Now bend your cock down and pull it through the ring.

As you can see, putting on one of these little buggers before you have a raging hardon is gonna make it a whole lot easier. To take the cock ring off, simply reverse these steps, pushing your flaccid cock back through the ring first, followed by each of your balls and finally your ball sack.

It’s absolutely essential that you not wear an inflexible (metal) ring for longer than a couple hours. Make sure you don’t buy one that is too small either. If your dick is turning an angry red or worse, purple, or it is cold to the touch, you’re in trouble. Take that ring off immediately. If you don’t you will risk serious injury to your precious johnson. Remember people, play smart with all your toys!

Good luck

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Ask for what you want

Name: Mikel
Gender: Male
Age: 25
Location: Seattle
My problem is: I have a fixation on cut dicks, so when I’m having sex with uncut people, I can’t enjoy it. I feel it’s dirty!!! Should I ask my partners their “shape” before having sex? Wouldn’t I sound like a whore?

What a curious concern you have. I mean, not the cut/uncut thing…that I understand. Lots of people banana_009have a preference for either cut or uncut meat, so I’m cool with that. And sometimes the preference is culturally induced. OK, fine! I also know that some guys prefer what they don’t have. Lots of cut men like uncut cock, and lots of uncut men prefer their partners to be cut. Some people make a big to-do about foreskin, as you suggest, because they think it’s unsightly and/or unclean. Personally, I think that’s complete baloney, but hey, to each his own. Right?

I also know that most people who have a strong cut/uncut preference want to know in advance if their perspective partner’s dick is to their liking. And obviously, the only way to find that out is by asking outright. OK, so far so good.

banana2What I don’t understand about your question is that you think it might be whorish to be up-front and ask a guy about his dick. Like, WHY? Either you don’t understand the meaning of the word “whore,” or you’re just overly sensitive about taking responsibility for what you want. Either way it makes no sense.

Think about it this way, say you don’t ask and you discover, to your great dismay, that the guy you’re about to bone has some fine lace curtains (foreskin). And you get all turned off and this screws up the screwing. You feel bad, he feels bad, and you look like a jerk. Wouldn’t it have been better to save yourself and your unlucky partner the embarrassment of shutting down a fuck by taking responsibility for your predilection before cloths come flying off? Heck, I don’t know about you, but I’d prefer to be thought of as a whore than a complete asshole.

Dr Dick has a hard and fast rule when it comes to sex. If you can’t bring yourself to ask for what you want, then you deserve what you get.

Good luck

Pride Goeth Before The Fall

Name: Jen
Gender: female
Age: 59
Location: North Dakota

I’m a widow and I am so sad. The fellow I’m going with, I really love him, but I can’t have an orgasm with him. I was able to have an orgasm with my husband who is passed away. And I can when I am playing with a toy by myself.

He has such pride and I don’t want to hurt his feelings, because it would take me about a half hour of foreplay to get there.

Thank you for your message, Jen. Your concern about your man and his inability to rock your world is, sadly, a very familiar complaint. I hear it from women all the time.pride

You say that your man is prideful and that you don’t want to hurt his feelings. But are you really willing to sacrifice your sexual wellbeing on that altar? I hope not. Even prideful men can learn something about pleasuring the woman they are with.

Let’s just say that this guy your dating knew how to pleasure all the women he has ever been with previous to you. That pedigree doesn’t make him an expert on pleasuring every other women he will meet, and that includes you.

Allow me to share with you the exchange I had with another woman in your situation. Perhaps my advice to her will be helpful to you. This is from…

Name: Zoe
Gender: female
Age: 25
Location: Boise
I learned how to masturbate when I was 12. From that first time I’ve loved how it makes me feel. No matter how good my lovers are; they never come close to the pleasure I feel when I’m touching myself. I like the intimacy I have with my boyfriend, but he’s not very good in the sack. I’ve been trying to get him to watch me masturbate, or we could masturbate together, so that he’d know how to touch me and make the bells ring. Unfortunately, he’s really straight-laced and he thinks my suggestion is perverted. He resists every time I bring it up. Sometimes after we have sex, I wait for him to fall asleep then get myself off. Is this selfish?


You betcha it’s selfish, selfish as all get-out. Not you, Zoe, but the bonehead you’re fuckin’. This is a classic, “you can lead the horse to water, but you can’t make him drink” sorta deal. Only here we have a “you can lead the horse’s ass to the mysteries of pussy, but you can’t make him appreciate them.”

I gotta ask, what makes a sexually enlightened chick like you hook up with and stay with bozo like him? Do you actually think that he’s gonna magically come around one fine day and let you lead him to nirvana? I think not. You know why I think this? It’s because you’ve created a monster — an “all I need to worry about is me gettin’ off in my girlfriend’s snatch” kinda monster. And that’s one scary kinda monster.

I am of the mind that it’s fruitless to try to get an obstinate partner, like your guy to do something he doesn’t want to do. The nagging alone will harden his resolve to resist. This does not mean you’ll never get your way. It just means that you have to go about this in a completely different way than, “oh honey, won’t you please cum and watch me jill-off? In the numbskull’s defense, he may be missing the point completely. He may not understand why you want him to watch you pleasure yourself. So if your agenda is to get him to be a better lover, that’s how you’re gonna have to approach the big lug.

First off, he needs to be told, in no uncertain terms, that he’s not the Hercules in the boudoir he thinks he is. This is gonna sting his ego like crazy and it might very well be the end of him and you altogether. But I assure you, risking this is much better than maintaining the status quo. Because, with each passing fuck, he will be more convinced then the fuck before that he’s da man.im_da_man

Once you burst his bubble, you’ll need to immediately inflate a new one for and with him. Us men folk can’t live very long with out our illusions. Begin this inflation process by taking some responsibility for this predicament. Own up to keeping him in the dark about his lack of sexual prowess. Then tell him that there’s a very easy and fun fix for the problem. Maybe if he understands that you want to jill-off for him as a tutorial, he’d be more compliant.

I’d be willing to guess that if you made this presentation more of a game or a role-play scenario then a seminar he’d be more receptive. Why not try something like this. Introduce a blindfold into your sex play. Have him strip down to his jock for you, then blindfold him. It’s gonna be his job to get you off without using the magic wand he has stuck in his jock. The blindfold will necessitate that he use his hands (and mouth) to find and pleasure you. While you tease his dick inside his jock guide his hands to your pussy. He’ll no doubt be fumbling around at first, so you’ll have to encourage him with some dirty talk, or actually use his hand to jill yourself off. Just remember keep it fun and playful and keep his dick safely tucked away.

You can see how this little exercise could be educational for him without being emasculating. Once he figures out that there’s more to sex than the old in and out, he might actually cum around, so to speak. Similarly, you might, on another occasion, submit to the blindfold yourself and have him use your hand to jack himself off. In time, you be able to do away with the blindfold altogether. But then, you might want to introduce restraints of some sort. While he’s buck naked and restrained put on a hot and horny show for him. Tease him with your self-pleasuring, but don’t let him touch you. Maybe rub yourself with his stiff cock. Since he’ll be unable to resist, it will be like masturbating with his pecker. Doesn’t that sound like a load of fun for all concerned?

Good luck

It Just Don’t Look Right

Name: Manson.
Age: 21
I was born with hypospadias and I was operated three times during my life. The last operation was when I was 16. Now, I am 21. My problem is that my penis is only 11 cm or 4.3 inches! I am middle-eastern. I am worried about my penis size, since I have heard it won’t grow longer after the ages of 21-25. What is the best method of penis enlargement that you can suggest in my case?
Thank you

First, a quick review of what is hypospadias is for those unfamiliar with the term. It’s an abnormality of the urethra in some men. It involves an unusual placed urinary meatus (piss slit). Instead of opening being at the tip of the glans (or dickhead), a hypospadic urethra opens anywhere on a (raphe) line running from the tip of the dude’s cock along the underside of the shaft to where the base.

hypospadic 2This happens when a guy’s dick does not fully develop in the womb.

This condition has levels of severity, from the hardly noticeable to very obvious. Some children are born intersexed, and have ambiguous genitalia, which requires sexual reassignment surgery. But I’ll save that discussion for another time.

Some guys, particularly those with conspicuous hypospadias can develop a complex about their appearance. This in turn, impacts on their self-image and complicates their ability to form lasting sexual/partner/marriage relationships. Severe hypospadias can also interfere with procreation. Other men, perhaps those with less conspicuous or severe hypospadias show little to no concern for the appearance of their dick and live completely normal lives.

Some parents of children with mild hypospadias seek a surgical correction to the problem. I view this as a highly risky means to solve a less relatively innocuous cosmetic problem. There are men who were operated on as a child who now, as adults, resent the interference. Are you one such man, Manson? You say you’ve had three surgeries. As you may know, matters are often made worse rather than better through surgery. And of course, there’s always the risk of complications, infections and the like. There are, however, more serious cases of hypospadias that demand reconstruction. If your dick issue is causing you anxiety or low self-esteem, help is available. Check out: The Hypospadias and Epispadias Association.

On to the size of your cock. While your cock falls on the smaller end of the spectrum, it still is near the average. You might want to google — average penis size to get the lowdown on that.

It’s true what you suspect. Don’t count on your dick growing any larger than it is. And frankly, there are no effective methods for permanent enlargement. Here’s what I wrote to another young man (18yo) who wanted to grow his dick bigger…

Jeez, this is just about my least favorite topic of all. I keep promising myself that I won’t respond to anymore “how do I grow my dick bigger?” questions. And then along comes a young pup, like you John, and asks the question again. Here’s a tip, everything I have to say about cock enlargement schemes I’ve already said. If you want to know my thoughts about this wearisome topic look for the CATEGORIES pull down menu in the sidebar to your right. Under the main heading Body Issues you will find a subcategory Cock Size. Once you read through all columns and listen to the podcasts you will have all the information you seek.huge pen..

But since you’re a youngster I will respond kindly. First, you’re not even completely through puberty yet, John. So if you could just chill out for a couple more years till your growing spurt is complete, you might find that nature itself will resolve your issue for you. If, by chance, you find that by your 18th birthday your cock is no bigger than it currently is, then it’s time to make your peace with your piece. Because basically that’s the dick you’re gonna have to work with for the rest of your life.

In other words, you have about as much chance of growing a bigger dick than what your genetics has determined for you as you do growing your feet bigger or adding inches to your height or changing the color of your skin. It’s simply not gonna happen. There is no true way of safely increasing either the width or the length of your johnson short of a surgical intervention. And I never recommend that.

Just like there are ways to give the illusion of bigger feet, darker or lighter skin or being taller than you really are, there are things you can do to create the illusion that you’re growin’ yourself a bigger dick. But all the creams, the jelqing, the pumps, the weights, the what-have-you, will only have a short-term effect if they have any effect at all. In the end you will have spent a whole lot of money, wasted a lot of time, been consumed with a great deal of anxiety and possibly even injured yourself to wind up having what you’ve always had and not significantly more.

May I suggest that you practice accepting what genetics has determined for you in terms of cock size and everything else. Because that will give you more time and energy to learn how to use what you have to its greatest benefit. Luckily, our capacity to be a good, and even great, lover has nothing to do with the size of our cock. Anyone who tries to tell you different is pullin’ your leg.

I hope this is helpful.

Good luck

An (extremely long) Tale Of Woe

First Name: Sam
Age: 22
Gender: Male
Location: North Carolina, USA
Wow, where do I even begin….

I am a 22-year-old gay male and believe that I may have SOME form of erectile dysfunction. I emphasize “some” because it is possible for me to get hard, firm erections, but I’m ALWAYS by myself when I do.

I have been able to give myself orgasms since I was in preschool. I did not masturbate the “traditional” way that men do (or ejaculate) until I was in 6th grade. Before that, I would lay down with my hands cupped around my crotch area and would “hump” into them until I felt an orgasm sensation and would then stop. In 6th grade I began to look at gay internet porn, and, seeing how most of those men masturbated, began to emulate the process. I even practiced “edging” often, beginning in 6th grade, as I had read on the internet at that time that it built up sexual stamina and led to powerful orgasms.PERFORMANCE_ANXIETY_pic_02_3

I would say that since I’ve been able to have orgasms (beginning in preschool), I would have one usually at least once a day. There were days here and there where I wouldn’t, but I guess an average would be 6 out of 7 days per week, with an average of twice per day. Of course, it’s hard to average them out since I’ve been having them for so long.

I did not start having sexual intercourse until my freshman year of college when I was 18, with my roommate at that time. Even that first time, I had problems maintaining my erection. I also had to use my hand and masturbate in order to have the orgasm, which took much longer than when I’m by myself. My roommate and I engaged in sexual intercourse regularly for the latter 2 and a half months of my freshman year, and every time, I had to have an orgasm by masturbating. Oral sex would not work, his hand would not work, and we did not engage in anal sex.

From ages 19-20, I had very little intercourse, but regularly masturbated (almost always to porn), and had no problems maintaining an erection and achieving orgasms. I hooked up with older men occasionally during this time, and again, could not have an orgasm unless I masturbated. It was also slightly more difficult to get an erection than by myself watching porn, and always took me longer to achieve orgasm than by myself. I had my first experience with anal sex (as a “top”) during this time as well, and could not ever reach orgasm, same with oral sex and hand-jobs.

When I was 20 I met and began dating my first boyfriend. We were together for 10 months, and while I enjoyed my time with him, our sex life was poor. We did not engage in anal sex except once, because we both considered ourselves tops. The one time we engaged in anal sex I tried to be the bottom, but did not enjoy it at all and had to stop. We did engage in oral sex, but I could never achieve orgasm that way. Again, I had to masturbate in order to have an orgasm. Not only that, but I began to have significant trouble sometimes to get an erection. Also, it took a lot longer for me to reach orgasm when I masturbated with him. By myself with porn, I could reach orgasm as quickly as 5-7 minutes. With him, it often took me at least 20 minutes, and it was usually 25-35 minutes.

loving legsAfter we broke up, I began to hookup a little more frequently then I had in the past, but it was not that often. Whenever I did, again, I always had to masturbate to achieve orgasm, and it took me a long time to do so. AND, during some of these hookups, I simply could not even achieve orgasm myself, as I started to have difficulty maintaining or even getting an erection. I highly doubt it was because of my sexual partners, because I would not hookup with someone I was not sexually attracted to. Also, I usually could have erections during foreplay, but when it came to the “big finish” my erection would start to wane or just become completely soft, and nothing I did or thought about changed that. Once, I achieved orgasm from barebacking (which I have not done since and luckily did not contract HIV or an STD), and there was also only one time where I hooked up with a guy and achieved orgasm from him giving me oral sex, although I believe this was because I refrained from masturbating for the past few days beforehand.

I am 22 now, and am starting to worry that I will not be able to ever have any good sex with someone else other than myself. In almost all of my most recent hookups, I have had to use a cockring to get an erection, and even then sometimes it doesn’t even help. Also, in almost all of my most recent hookups, it either takes me around 30 minutes to masturbate to orgasm, or I simply can’t have an orgasm because of lack of an erection. However, if I am by myself watching porn, I do not have any trouble getting and maintaining “rock-hard” erections and reaching orgasm.

I have become particularly concerned about this problem now, because I have begun to date someone and engage in sex with him for the past few weeks. When we first had sex I topped him anally and had a good erection. But we still masturbated together to completion. Ever since the first time though, I have had a LOT of difficulty just getting an erection period. Cockrings do not help, and oral sex and foreplay don’t really help either. Sometimes when we make out for a while I’ll start to get kind of hard, but then when I try to get ready to penetrate him or simply masturbate with him, I’ll go soft again. I’ve been able to reach orgasms sometimes when I masturbate with him, but my penis is usually semi-soft when I reach orgasm, and again, it takes more effort and certainly more time to do so then when I’m alone watching porn. He is incredibly good FleshJacklooking, good at sex, and very passionate, so I know it is not him. Luckily, he does not mind when I cannot perform, he says he likes me for me and that everything is fine, and he thinks that I shouldn’t worry about it. But at this point, I really can’t help but worry about it…

The last time this problem happened I had willingly decided to not have an orgasm for three days beforehand, hoping that it would help the issue. But unfortunately, it did not help or change anything. I’ve decided to completely stop viewing or watching any pornography whatsoever, and have also decided that when I masturbate I will avoid as much contact with my hand and, instead, use my FleshJack (the gay version of FleshLight) with the “Squeeze” texture (their most “realistic” anal texture). I have not had sex with him since I decided this (which is the day I’ve written this question, May 27, 2015).

I apologize for this EXTREMELY long inquiry, but I didn’t want to leave out any details of my sexual history in case they were important. I’m wondering if masturbating regularly since preschool has anything to do with my poor performance. And I’ve considered that I’m “overthinking everything” when I engage in sex and maybe that’s preventing me from getting erections with other men, but I’m such a sexual person that I can’t think of anything but dirty, sexual thoughts when I’m with another man, yet it just doesn’t seem to work. I do start to focus on not being able to get an erection if I’m not getting one for 5-10 minutes, but during that time beforehand, I’m not thinking about anything other than the pleasure, so I don’t see what I’m doing wrong. The problem is beginning to be REALLY embarrassing and I’m concerned that if I’m already having these problems at only 22 years of age, I’ll likely have the worst of erectile dysfunction problems in the future.

I suppose my main questions are:
1) What could be causing this to happen?
2) Is my proposed method of completely avoiding porn and masturbation via my hand an appropriate solution?
3) Do you have any specific suggestions or general advice that can help me with this problem and/or my sex life?

Again, I apologize if this is way too long; I’ve just never been so concerned about it before. I’m 22, I should be able to get rock hard erections easily, but I feel like a 70 year old man who just “can’t get it up.” ANY advice you can give me will be sincerely appreciated.

Whew, Sam, that was like the War And Peace of sex advice questions.

It’s perfectly clear that you are worried about your sexual response. But I’m gonna guess that your worry is actually making things worse. Before I respond to your three questions, I want to say; get thee to a therapist! You need to sit down with a sex-positive therapist and work through this stuff with him/her. This is super important, don’t just blow it off. If you need a referral, see the Directory of the American College of Sexologists to find someone in your neck of the woods. I also offer remote therapy via Skype or phone. See my Therapy Available page.

whewNow to your questions in the order you asked them…
1) What could be causing this to happen?
Everything you tell me points to performance anxiety. I’ve written and spoken a great deal about this issue over the years. Use the CATEGORIES pull down menu in the sidebar to your right. Scroll down till you find the main category, Sex Therapy. Under it you will find the sub category, Performance Anxiety.  You’ll find tons of information.

2) Is my proposed method of completely avoiding porn and masturbation via my hand an appropriate solution?
It might be, but not for the reason you suspect. Again, you need to discuss this with a therapist. It’s important and more involved than I have time and space to lay it out for you.

3) Do you have any specific suggestions or general advice that can help me with this problem and/or my sex life?
Yeah, chill the fuck out! Honesty, that’s the best thing you can do right now. Then, with the help of a therapist, work through your problems, put in place a program to rebuild your partnered psychosexual response one step at a time. You’ll probably begin with sensate focus training, stress reduction, and relaxation exercises.

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