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Name: James
Gender: Male
Age: 19
Location:
I want to know if I should have sex with a man for the first time.

Well gee, darlin’, I suppose that would all depend on if you are into man-sex or not. If you are, I suppose having your first encounter will be like falling off a log. However, if you’re not into gay sex, then why would you even be considering such a thing.boys kissing

For the sake of argument, let’s just say you are into some hot man-on-man action, or think you are. If that’s the case, I have some questions. Do you have a particular partner in mind? If you do, what is it about this guy that makes you want to get physical with him? If you’re honest with yourself about this, you will probably be able to determine what kind of sexual contact you want to have with the dude. Which brings me to my next set of questions.

What kind of gay sex are you looking to experiment with? Something light, like kissing, making out, mutual masturbation, shared hand-jobs? For more information on this, check out my swell tutorial about hand jobs titled: The Art Of The Humble Hand Job.

Perhaps you’re looking to be a bit more adventurous, like cock sucking. That’s great too. But wait! Would you know how to smoke some pole with grace and ease? If not, check out my tutorial: So Ya Wanna Be A World-Class Cocksucker …Or How To Give The Perfect Blow Job. To find this brilliant expose and lots more information about the humble hummer, go to the CATEGORY pull down menu in the sidebar and look for “ORAL.” Then look for Cock Sucking.

Maybe you’re considering butt fucking. That’s a bit advanced for the gay sex novice, but it’s not unheard of. If I were you, I’d return to the CATEGORY pull down menu in the sidebar and check out the heading “ANAL”. There you will be treated to loads of information about being a good top, like my tutorial, Finessing That Ass Fuck — A Tutorial For a Top. As well as my tutorial for being a good bottom, Liberating The B.O.B Within.

There’s only one thing you absolutely need to know when it comes to ass fuckin, regardless of what position floats your boat. Be sure that whoever is on top uses a condom. And if you don’t know why you need to do that, then darlin’, you’re just not ready for sex with any kind of partner…same sex or otherwise.

Good luck

Name: Tony
Gender: Male
Age: 24
Location:
I’m trying to find out how to get ink marks off my dick without hurting my dickhead.

Whoops! Looks like you need to reevaluate the company you keep when you drink to the point of passing out, my friend.

I realize writin’ shit on a guy’s johnson while he’s unconscious is a hilarious practical joke among the frat-boy crowd. I mean, what could be funnier, right? Of course being on the receiving end of this little prank, like our friend Tony here, is considerably less comical.

i enjoy penisRidding oneself of ink marks, particularly the indelible variety, from one’s privates is a pain — both literally and figuratively. The best one can say about this clean-up chore is that it will probably cure the guy of binge drinking, at least with a bunch of rowdy adolescent-minded companions with Sharpie markers and too much time on their hands.

OK, Tony, here’s what you do. First, apply a liberal coat of baby oil or mineral oil to the effected area. Take your time massaging the oil into your skin. You may discover that this oily massage gives you a woody. That may be the silver lining to your ink-stained cloud. Actually having an erection will help expand the skin of your dickhead and allow the mineral oil to better penetrate the skin. The oil will sink into your skin and help lift the ink stain to the surface.

Follow this part of the treatment with lots of warm soap and water. You should see ink stain lessening.

Next, massage in a liberal mount of rubbing alcohol. Follow this with more warm soap and water.

Continue alternating between mineral oil followed by soap and water and rubbing alcohol followed by soap and water. Always ending the treatment with the soap and water part. A couple applications like this should do the trick. I would, however, recommend that you be as gentle as possible. If the satin persists after two such applications, give your prick a day to rest before attacking the stain again.

Good luck

Hey dr dick! What’s that toll-free podcast voicemail telephone number? Why, it’s: (866) 422-5680. DON’T BE SHY, LET IT FLY!

Another Selfish Asshole

Name: Samuel
Gender: Male
Age: 36
Location: Arkansas
Eight years ago I was involved with a woman who liked to fuck me in the ass with a strap-on. I liked it a lot, and when we stopped seeing each other, I missed the sensation. I’ve tried hooking up with other women who want to do this to me, but I’ve only found a few. And all of them were looking for a relationship, something I don’t want. Eventually I turned to men for the anal action I was missing. Some of guys are gay, some bi, and some straight. We never hug, kiss or do oral. I only receive, never give. I don’t see a guy for more than a couple of times. Now there seems to be fewer guys out there who want a tight ass to fuck. I prefer women, but men will do — I just really get off on the sensation.

Well, aren’t you a charming fucker…I mean fuckee. You don’t have a clue about how selfish you’re being, do you? And you’re wondering why the pool of people willing to pound your “tight ass” is drying up. It’s not the lack of fuckers out there. darlin’; it’s you!asshole

Listen; there are some basics that you seem to have overlooked when it comes to partnered sex. First among these is ya need at least a modicum of mutuality in your sex play. Did you ever hear of “Give to Get?” There’s probably no mystery why the first woman who strapped one on for you fled the scene. She discovered that you’re just in this for yourself. The other women who pegged you did so hoping they’d get something in return. Even the guys are fleeing in droves. And it’s entirely your fault, Sam. And ya know what else? I’d be willing to bet that you’re getting a reputation for yourself there in Arkansas. Nobody likes a self-absorbed prick. And that kind of bad rep gets around fast, especially in the hinterlands.

ill-stop-being-sarcasticAnyone wanting to get laid as much as you ought to learn how to finesse the fuck he wants. Lets start with the women. Most women are unaccustomed to being a top. Many would feel pretty self-conscious with a strap-on. In exchange for the kind of extraordinary sex you are looking for, most women would want something in return. Most would feel more comfortable exercising a kink in a relationship of some sort or another. They have little to gain otherwise. And if your behaviors with men are any indication of the sex you have with women, it’s surprising that you’ve got pegged at all.

Most men are a lot like most women in this regard. While there are a few of us men folk who will fuck whatever presents itself; even they will look for something in return besides a self-proclaimed tight ass to fuck. And here’s a tip — most guys who crow about how tight their ass is, are deluding themselves. Your insatiable hole is probably not in as pristine condition as you’d like to think.

I have several suggestions for you. First and foremost, treat your partners, even your casual hook ups, with some dignity and respect. Each one is more than just a stiff dick (or dildo) for you to pleasure yourself with. If you want to prevent the pool of available fuckers from evaporating completely, show some humanity yourself. Find out what turns your partner’s crank and get her/him warmed up for the fuck fest. If it take some hugging, kissing and a decent blowjob…you’d better take care of business. It’s the least you can do.

Finally, if you have a preference for women (and you’re put off by the idea of hugging, kissing and a blowin’ some dude just to get your sorry ass fucked); then rethink your aversion to having a relationship. There are all kinds of relationships — from fuck (pegging) buddies to marriage. Surly, you could find it in your heart to reward the woman willing to plug your hungry ass with a little something more than “catch ya later, bitch!”

Good luck

What does is all mean?

Name: Jane
Gender: Female
Age: 23
Location: Vancouver. BC
When my boyfriend and I have sex, there’s a 50/50 chance that he will put his penis between my butt cheeks and hump me that way until he cums. (It’s just intense rubbing, no anal penetration). Even though I don’t feel like I’m getting any pleasure from it, my vagina gets wet, and if he touches me down there and feels that I’m wet, it turns him on even more. What’s going on here?
He’s very affectionate and he tells me he loves by my body. He says he’s totally straight, but this whole anal thing confuses me. If he’s not gay or bi-sexual, why is it that it takes him 20+ minutes to cum during vaginal sex, but only 5 – 7 minutes to cum during anal?

Ok, Jane, to start with, your BF isn’t doing anal. Believe me, darling, you’d know if he were. Anal sex, by definition, means anal penetration. There’s a name for what your freaky boyfriend is doing — rubbing his cock in your crack, but not penetrating you. It’s a form of frottage, or sexual stimulation by rubbing. This is the sexual practice of choice for most lesbians, most commonly referred to as pussy-bumpin’. Hey, maybe your BF is a lesbian!analsex joke

Second, your pussy may be getting wet because your boyfriend’s pre-cum and spooge is dripping down your crack, past your “taint” and all over your fine cooch. It ain’t you producing the wetness, which explains why you’re not aroused. I hope that clears up the mystery juice for ya.

Third, loads of exclusively straight men are into anal. Most are into butt fucking their women, but some are into being fucked BY their women. We call this practice pegging — a woman straps on a mighty fine dildo and drives her man insane with a buggering he’ll not soon forget. So you see, fucking is not just for cunts anymore!

Forth, perhaps, just maybe, your vagina isn’t as tight as your what your man is experiencing between your ass cheeks. Maybe, just perhaps, that’s why it takes him less time to bust a nut that-a-way than in a more traditional form of fucking. Also maybe, he’s more turned on with the allure of the forbidden, taboo backdoor action. I guess the only way you’ll know is to ask your BF straight-up, as it were, so to speak.

So let’s review then, shall we? Now that we know for certain that an interest in cornholing a sweet ass is not just a gay thing. You can relax about your BF bein’ queer for wanting to hump your bum. For some guys this is their favorite kind of sex. They love to bust a nut by rubbing their dicks between a chick’s tits, thighs, buns, or feet. It’s anyone’s guess why these dudes prefer this to getting off in, on or around a pussy, but whatever it is, it’s completely harmless.Anal sex

Here’s a tip, Jane. Relax into this with the ‘ol BF, why don’t ya? Once you stop worrying about his sexual orientation because of his fascination with your be-hind, you may actually enjoy the special attention he’s paying your boot-ty.

And hey, if your BF’s freak with your ass crack isn’t gettin’ you off, you don’t have to just lie there and take it, ya know. While he’s grinding away back there, you could be spending some quality time with little miss clit with say a swell vibrator. Soon you’ll be enjoying things as much as he.

Good luck

It Just Don’t Look Right

Name: Manson.
Age: 21
Location:
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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