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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.

If That Don’t Beat All!

Name: Ned
Gender: Male
Age: 59
Location: usa
My wife enjoys using my penis as a tic tac dispenser. I insert one (or several) into my urethra. Shortly afterwards, she sucks them out. It’s enjoyment for both of us. My question: sometimes there’s a little discomfort that usually goes away in a day or two. Is there something I can use to lessen this sensation? Is this practice too risky to continue? Can I do damage to myself?

tic-tac-fresh-mintAlrighty then; this is pretty out there, Ned. I have to say; no one’s ever reported being a human tic-tac dispenser before. So you get some extra points for the novel use of your pecker. But I’m sitting here trying to imagine how this play got started. I mean, who had the brilliant idea to shove tic-tacs in your piss slit first — you or your wife?

It’s not like I haven’t had guys tell me about the odd things they’ve slipped into their urethra. And ya know what? It’s generally a guy thing. I’ve not had a woman report such activity. I do know a couple of women who are into using urethral sounds, but nothing more exotic than that. In terms of the guys though, I could tell you stories that would make your hair stand on end.

You say “sometimes there’s little discomfort that usually goes away in a day or two.” Ya don’t say! Several things could cause the discomfort you report. Two come immediately to mind. 1) The mint in the tic-tacs will no doubt be an irritant to the sensitive mucosa in your urethra. 2) You’re probably forcing the tic-tacs into your piss slit without using lubrication too, right?a little nuts

Is the practice risky? Probably! I’d never suggest anyone insert anything into his urethra that is not sterile. However, if you insist on continuing this play; the least you could do is add a drop of lube on each tic-tac before insertion. Just know that if you’re not careful such behavior carries a risk of severe irritation; tearing your urethra; or a nasty urinary tract infection, which can become more serious if it spreads to your bladder or kidneys.

My rule of thumb when considering unique uses for one’s body parts is if there is pain, something is amiss. If you can diminish the pain by being more thoughtful and careful about how or what you are doing then, things will probably be better than if ya don’t.

Good luck

What a pain in the ass!

Name: Dan
Age: 55
Gender: Male
Location: Illinois
My wife and I have enjoyed anal sex (giving and receiving to each other) for years, but now I have a problem I need help with. I had a hemorrhoidectomy surgery 3 months ago and we waited 3 months to start up again. Now using the same strap-on as we have been using it was very uncomfortable. The strap-on is only 1-1/2 “thick and I tried again by my self but it did not matter how much lube I used it still hurt. Then I started bleeding. It seems that when the hemorrhoidectomy surgery was done it made my rectum smaller. The question I have is; is there away to stretch the rectum back to the pre-surgery size or do I have to buy smaller toys (the 1-1/2” is the smallest we own right now)? I appreciate any help you can give.

Sorry to hear about the pain in your ass, Dan. I know that recuperating from invasive surgery like that isn’t fun.

ass-painHere’s the thing; I believe that you’re gonna need way more than 3 months to heal completely from the hemorrhoidectomy. I know, bummer, huh? If I had to guess, your down (pardon the pun) time will be more like 6 months to a year.

At 3 months, your ass is, no doubt, healed enough for comfortable bowel movements. But butt fucking is quite another thing. And I don’t think it’s simply an issue of stretching your rectum or the amount of lube you use. Internal healing isn’t like external healing. Plus, there’s the fact that every one of your bowel movements is stressing your rectum making the healing process more lengthy. I encourage patience.

That’s not to say that you still can’t enjoy your hole. External simulation on your rosebud will feel real nice. Digital stimulation, just inside your hole, might also be possible. Just don’t over do it or you will find the healing process will take even longer.

I have a question. Are you able to stimulate your prostate without pain? Or do you experience pain with any insertion to any depth?

Since you’re not here to fill me in on the gory details, I’ll try to respond to my own questions. If you are able to stimulate your prostate without difficulty, I recommend that you keep your anal wanderings to that depth. If, on the other hand, you can’t even go that deep without discomfort, then I suggest you stick to external stimulation for the time being.pain-in-the-ass

I already suggested butthole massage, but don’t forget your perineum, or taint, if you will. I suggest that you find a good strong vibrator, perhaps one that has a pointed (phallic) shape to it. You’re gonna want some fine pin-point accuracy for this stimulation. Move back and forth between your hole, over your taint, to your balls. Stimulate the whole shebang down there. I think you will find that pressing the vibe into your perineum will shiver your prostate in the most delectable way. Done correctly you will discover that your whole pelvis will light up.

[Anyone out there who is afraid of anal insertion, but wants to experience some of the fabled pleasures associated with being a butt pirate, will want to give this external vibration thing a try. Who knows, one day you might wind up slipping the phallic shaped vibe in your ass for real and discover that your insertion fears were unfounded.]

Dan, give your ass at least 3 more months to heal. At that time try doing some very careful and tentative insertions to see how things feel down there. If there is even the slightest pain [internal pain as opposed to sphincter discomfort] stop what you are doing. Don’t try and force the issue. Like I said, this could take a year to heal properly.

Keep me posted on your progress.

Good luck

Hey, Where’s My Big “O”?

Name: BJ
Gender: Female
Age: 23
Location: PA
I’ve been sexually active for several years now and have yet to reach an orgasm. Oral sex, intercourse nor masturbation have been effective. Is there something wrong with me, what might help?

I’d be very much surprised if there was actually something physically wrong with you. But you clearly have some difficulty letting go. And simply put, an orgasm is letting go of built up sexual tension.the big O

Lot of preorgasmic women don’t feel entitled to an orgasm, for one reason or another. Other women are simply unversed on how to make the big “O” happen in their own fine self. Sometimes it’s a combination of both resistance and a lack of know how.

I once had a client, a woman in her late 30’s, the mother of three and a devote Catholic. She was preorgasmic too. Her big stumbling block was fear. You got it; fear of having an orgasm. She had heard from other women over the years how powerful orgasms were and how much fun they were. My client somehow got it in her head that if she were to ever let go and give up that long-awaited screamin’ meme, her entire world would collapse. She’d become a sex addict, neglect her children, divorce her husband and turn her back on God…the whole enchilada.

With that kind of mindset, this little lady wasn’t gonna let herself cum no how.

the big O 2I had to reassure her that, as delightful as orgasms are, they are not like crack cocaine. I told her there was no chance that she’d fly to pieces as a mother, wife and friend of Jesus if she were to diddle herself once in a while. I had to keep repeating this over and over till it finally sank in. You talk about hardheaded! In the end, she had her precious orgasm, joined the ranks for the sexually satisfied and lived happily ever after. …Well, I can’t honestly say about the happily ever after part, but she sure did smile a whole lot more afterwards.

Back to you BJ, I don’t suppose there’s any way you could have one of your gal-pals show you how it’s done, is there? The reason I ask is most guys learn how to choke the chicken by watching, or being instructed by another guy. Us men folk are really good about doin that for one another. Women, on the other hand, don’t seem to do this for one another as much. Which is a freakin’ pity, if ya ask me.

If you can’t (or won’t) get a pal to show you around proper pussy pleasuring, I have another suggestion for you. Mozie on over to DR DICK’S HOW TO VIDEO LIBRARY  and check out a swell instructional video. (There’s a link to this marvelous resource in the header.) Do a quick search for “female masturbation” and let the experts show you a thing or two. You’ll be so glad you did.

Another great resource: The Ultimate Guide to Orgasm for Women: How to Become Orgasmic for a Lifetime by the brilliant Mikaya Heart. By the way, you can find a dynamite two-part interview with Mikaya HERE and HERE!ultimate-guide-to-orgasm-for-women-lg

Here are a few tips:

Get in the mood

Relax as much as you can. Whatever that means for you. Take a warm bath or have a glass of wine. Ensure your privacy: turn off the phone, lock the door for privacy from roommates, kids, whoever. Find a comfy position. Most women start out lying on their backs, legs bent and spread apart, with feet on the ground. Remove most or all of your clothing (or as much as your comfortable with).

Explore your body

Run your hands along your body, lingering along areas that are more responsive to touch than others. If you’re able to do it, and you’ve never done it before, you might want to try to look at your genitals in a mirror. Because so many women are raised with negative messages about their bodies, and particularly their genitals, being able to see while you touch can be powerful and surprising. Find and touch your inner and outer labia, your clitoris, your vagina and your perineum.

Touch yourself

Using one or two fingers, rhythmically stroke the different parts of your vulva, paying particular attention to your clitoris and labia. Experiment with different types of pressure, speed and motion. Try placing a finger on either side of the clitoris and stroking up and down, or placing two fingers on the clitoral hood and rubbing in a circular motion.


Try different types of touch: stroke, tickle, knead, pinch, or lightly pull your genitals. Try using one or several fingers, the palm of your hand, even your knuckles.

Build up excitement

Learn to hold onto sexual excitement by building up and then reducing or temporarily stopping the stimulation. (Men do this all the time when they jack-off.  It’s called edging.) Pay attention to how your body is responding. It will tell you the particular stroke that feels best and when to pick up or slow down the tempo.

Don’t forget to breathe

Many women hold their breath as they get excited. Be mindful of your breath and learn to play with breathing during arousal. Try to breathe deeply rather than hold your breath. This can help release the sexual energy, rather than fight it.

Moving a little

In addition to often holding our breath, many women tense up and don’t move much at all when wtheye masturbate. This might work for you just fine, but if you haven’t explored movement, it’s worth a try. Moving while you are getting turned on, and moving during orgasm can change the way you experience pleasure in your body. For some women this means rocking their pelvis. For others it means moving their legs or torso side to side. Find what movement works for you and then intentionally start doing it while you masturbate.

Letting go

If your hand gets tired, give yourself a rest, switch hands, or try a vibrator. If you’re on the brink of orgasm, but can’t quite get over the hump, try to become more conscious of your breathing, give yourself extra stimulation: caress your nipples, or try thrusting your other fingers or a dildo in and out of your vagina.

Ride the Wave

As you begin to orgasm, continue the stimulation through the orgasm. Lighten up on the stimulation during the first extremely sensitive moments but keep it going to enjoy those little pleasurable aftershocks. Your first orgasm may feel like a blip or a blast, but the more you practice, the more variety you will experience.


Sexual fantasy can be a double edged sword when it comes to masturbation. If you have trouble getting yourself in the mood or getting over the top, a hot fantasy may be just the ticket. I often suggest reading erotica to get in the mood. However, when we fantasize some of our attention is taken away from what’s happening in our bodies in the moment. Sometimes what is getting in the way of us enjoying masturbation is that distance from our bodies. It’s good to try everything, but be mindful of whether or not your fantasies are acting as an enhancer or a distraction.

hitachi-magic-wand-2Some final thoughts…
Vibrators take some of the manual labor out of masturbation by providing direct, intense physical stimulation to the clitoris.  check out all the marvelous vibrators we’ve reviewed for you at Dr Dick’s Sex Toy Reviews.

Many women learn to jill-off in the bath or shower. A direct the stream of water on your vulva and clitoris can be a game changer. Vary the pressure, the pulsation, and the temperature. Alternate methods: slide your butt over the drain so your legs are up in the air and your genitals are up under the tub faucet (rather awkward but do-able for some), or use Jacuzzi jets.

Rub against something–a pillow, the corner of some furniture, a washing machine in operation.

Dildos can be a pleasurable accompaniment to clitoral masturbation, as they offer the fullness of penetration and can also stimulate the g-spot.

Write back again, BJ, and let me know how things go. If you’re not successful, I still have a few other tricks up my sleeve.

Good luck

Stretching out of the sexual doldrums

Name: Gwen
Age: 57
Location: Philly
My husband and I have been married for 33 years. Our relationship is hell when it comes to sex. My husband is overweight, and he’s stressed out about his elderly parents. Sex is non-existent. He never was the instigator in our relationship. And he is the kind of guy who thinks having sex on the couch as opposed to the bedroom is adventuresome. He has become so boring. I don’t believe the man feels sex should be that important at our ages. (I’m 57 and he’s 62) I, on the other hand, am more sexually aroused and creative than ever now that I am more mature and the kids are out of the house. Menopause and all the sex on the internet helps too. 😉 Is there anything I can do to make my man return to being a healthy sexual being once again? Thank you, Gwen

No, thank you, Gwen. Your complaint is a familiar one. In fact it’s so familiar I regularly offer therapy groups for couples in long-term relationships. Like you and your old man, these couples have, for one reason or another, hit a wall when it comes to their sex lives.senior intimacy

I take a very unique approach to these groups by inviting both straight and gay couples to the same group. At first I got a lot of resistance. Most couples, both gay and straight, think there is nothing to be learned from a couple unlike them. They can’t imagine why I would want to integrate the group in such a manner. I think most of my couples feel more comfortable being in a segregated group — straight folks with straight folks, gay folks with gay folks.

But that is of course the reason I integrate the groups. I don’t want them to feel all comfy and cozy, I wanted them to work and learn and stretch themselves out of their sexual doldrums. At first, I had to ask all my couples to suspend judgment about an integrated group until they had an opportunity to participate in one. Now I don’t encounter so much resistance. Word’s gotten out that this is a really creative solution to an otherwise tricky problem. And that old married couples, regardless if they are gay, lesbian or straight have very similar problems. And they can and do learn from one another.

To your specific issue, Gwen, I’m sad to say there’s not much you can do to beef up your sex life if there’s no interest on the part of your husband to do so. I mean, you can lead the horse to the cooch, but you can’t make him lick, if ya know what I mean.

Fat man holding a measurement tape against white background

Fat man holding a measurement tape against white background

You confide that you husband is overweight and stressed; this is not a happy combination when it comes to his sexual response cycle. In fact, your husband sounds like a heart attack waiting to happen. Perhaps if your challenged him about his general health — encourage weight loss and stress reduction, you might find that this would also reignite his sex drive. It’s worth a try.

And thank you for mentioning menopause. So many women find the changes that take place in midlife confusing and disorientating. It’s so good to hear from a woman who is eager to explore and enjoy her sexuality post-menopause.

Men also go through changes, in midlife. There’s even a name for it — andropause — the male menopause as it were. It’s clear that as we age, both women and men need more time and stimulation in which to get aroused. The slower, more sensuous foreplay that often results is a welcome change for most women and even some men.

Increased focus on sensuality, intimacy, and communication can help a sexual relationship remain rewarding even well into our senior years. I think you already know this, Gwen, but many women in my audience don’t.sensual touch

If your husband is avoiding intercourse, there still many ways of expressing your love and staying connected:

  • Hugging, cuddling, kissing
  • reading erotica aloud together
  • Touching, stroking, massage, sensual baths
  • Masturbation and oral sex

However, if your husband is more wedded to food and stress than he is to you, and if he continues to refuse to join you in finding an appropriate outlet for your sexual frustration, then it’s up to you to make this happen on your own. 57 is way too young to say goodbye to your sex life.

May I suggest joining a women’s group. Not a therapy group, but more of a support group or activities group. Getting out of the house, involving yourself with other self-actualized mature women, may uncover the secret solutions other women have put in place to find sexual satisfaction when they are without a partner or have a partner who’s no longer interested in a sex life with them. I think you will be surprised by how creative your sisters can be. Make it happen, Gwen. Don’t sink to the lowest common denominator of living a sexless life.

Good luck

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