LTR – DR DICK SEX ADVICE

March 21, 2007June 3, 2026

Pros and Wannabes

When it comes to sex, pro and amateur alike have issues. (It’s a good thing too; otherwise I’d be out of work.) Weather one is just getting the hang of things or one is making bank pleasuring others, body awareness and sexual technique can be fine-tuned.

In our culture just about everyone, regardless of age, faces some kind of bugaboo about sex and/or intimacy. When we are young, inexperience and the sexual misconceptions and misinformation that accompanies youth can seem charming to some. Youth, after all, is a time for stumbling about.

Not so when we’re all grown up. Those who are old enough to know better, but don’t, are not judged as indulgently as greenhorn youth. Older folks are expected to learn the lessons of youth while we are young. And while there are a whole set of particular issues that arise for us in our middle years, it’s exasperating to encounter an oldster who is still clueless about the fundamentals.

Hey Dick!
As you know, I am an escort. My business is doing very well. In fact, so well I need to ask if you know of any meds, besides Viagra, that I can take that will help me maintain an erection over a longer period of time?

Can I be frank? Here’s the deal, let’s say I have I have two one-hour clients during the day. Then a regular of mine calls and wants an all-nighter. That’s not a problem other than the fact that this particular client wants to get fucked hard. I mean real hard, for hours at a time. He’s an insatiable power bottom.

I want to be able to ride his ass, like the bitch he is. Hell, I’m even attracted to him. I just can’t stay hard enough to fuck him like he likes (especially after having had the two clients before him that same day). Sometimes I have difficulty getting it up for him, and wind up finger-fucking him till my hand is sore. I do not want to lose this client. And shifting days is not the solution. Because when he wants it he wants it and I have to produce. That’s what I do, I sell “muscle.” I have a reputation for giving the best hard driving, dominating and controlling sex around.

Again, is there a medication I can take to maintain the erection?
— Works Hard

Dear WH,

Your life reads like a cheap porn movie script. Lordy, the good doctor nearly got the vapors simply reading through your very explicit missive. (As you can see, I had to edit out some of the more gory details so I could protect your identity in this public forum.) Of course, as you suggest, it never hurts to advertise. You’re so bad!

I thoroughly understand the pressures you and other sex workers face. It’s not as glamorous a life as it is often portrayed, huh? Ok, so you’re beautiful, men idolize you and crave your attention. You’re getting loads of sex, putting all those “bitches” in their place, and crying all the way to the bank. It’s a tough job, but someone’s got to do it. But then again, there are all those sniggling performance issues that even a he-man like you must contend with.

The trouble lies in the fact that you are a workaholic. And that’s never good, regardless of the work one does. Sex work, like any other work, will burn you out if you’re not careful. If you don’t learn to pace yourself, darlin’, you’ll fizzle. (How’s that for an appropriate euphemism?) And from what you tell me, this is already beginning to happen. Keep it up (no pun intended), you won’t be the first causality in this line of work, nor will you be the last. But If you ask me, and I happen to know a little something about sex work myself, the object here is to grow old (or older in your case) in your chosen profession.

I’m tellin’ ya, WH, if the erectile burnout don’t get ya the psychological torment will. I’ll bet you’re terrified the word will get out that MR. Big-Beautiful-29-year-old-Stud-Power-Fucker can’t get it up. That would be real bad for business. And you know how those johns can gossip. Bitches! They don’t know that you’re servicing men at a rate that would make a superhero blush. All they see is limp willie and that spells trouble right there in River City.

It’s not surprising that you are having erection concerns given the number of clients you are seeing in one day. I mean, girlfriend, when do you find time to eat? You don’t need a new med, you need a vacation. If Viagra and a good cock ring don’t do the trick, then, in my humble opinion, your body is telling you to slow the fuck down.

And here’s another tip; research is beginning to show that prolonged and persistent use of Viagra can have some very unpleasant side effects. Those who overuse this potent cardiovascular drug, particularly young men who use it recreationally, may be in for some very unpleasant surprises down the road. So, I have one simple suggestion, WH, have a care about your sexual wellbeing and treat your dick gently. Despite the pounding you can inflict with it, it is a very delicate mechanism.

Good Luck

Dear doc, I am just about to turn 50 years of age. Is there a sex life ahead for me? I love sex clubs and anonymous sex. But is it too late for me to get into a relationship.
— Washed up?

I regret to inform you, Washed, sex does, indeed, come to a screeching halt right as you turn 50. In fact your dick is gonna fall off too, cuz you ain’t gonna be needin’ that little thing no more.

I mean, come on, I’m sure you know better than that. Thanks to the wonders of modern pharmacology even Bob Dole is getting laid, for Christ sake. Wake up and smell the coffee, Washed!

Oh, and one other thing, since there’s no guarantee that you’ve taken note of this subtlety, especially seein’ how you missed the big picture above, I have a tip for you. If it’s relationship sex you’re after, you’re gonna have to look for that in a different venue than where you are currently skulking around for stand-up sex. And you can pretty much count on the fact that relationship sex is gonna demand a whole different set of skills than anonymous sex. Do you have what it takes? Hmmm, the jury is still out on that. But if you’re just now lookin to nest at 50, I’d say an acquittal is highly unlikely.

Good Luck

Dear Doctor, I am gay, 49 and after a “broken heart” in my 30’s I went back to the closet for 20 years. I feel so lonely. Seems I have wasted my life. At my age, how can I ever find a lover with whom I can truly be happy, both spiritually and sexually? This is very difficult for me and I really would appreciate any good advice. Thank you. Kind regards.
— Lonely in Louvain

Dear LL,

Hey, it’s never too late to find what you are looking for. However, this particular quest is not for the faint of heart. If you’re prone to retreat into your shell, or closet as the case may be, every time you are disappointed or rejected, don’t even start this adventure. But, if your life of loneliness and isolation has taught you to value the companionship and love of others, then your years in the closet may not have been a total waste. Get out there and make a difference.

Live authentically; it is the best aphrodisiac. You may not find everything you are looking for in one package, but that shouldn’t matter. That’s the stuff for fairytales. The object is to satisfy your needs. So, if you find satisfying sex with one person and spiritual fulfillment with another, so be it.

And may I suggest that you try and expand your concepts of what defines happiness for you. You don’t want to box yourself in now that you’re finally venturing out of the closet.

Good Luck

March 19, 2007May 14, 2026

Sex Advice With An Edge — Podcast #06 — 03/19/07

[Look for the podcast play button below.]

Hey sex fans,

This week we have a slew of written submissions —

Roxy is a cock in a frock and his marriage is on the rock-s!
Young Pete is queer, and his yahoo family hates fags.
Gwen is over the hump, but still wants to hump.

And finally A Sexual Enrichment Tutorial —

Suppressing the Gag Reflex!

BE THERE, OR BE SQUARE!

Dr Dick is now on iTunes. You’ll fine me in the podcast section under the heading — Health, subheading — Sexuality. Or search for Dr Dick Sex Advice With An Edge. And don’t forget to subscribe. I don’t want you to miss even one episode.

Today’s Podcast is brought to you by: Daddy Oohhh! Productions, Quality Adult Entertainment, Enrichment and Educataion

Podcast: Play in new window | Download

February 12, 2007June 3, 2026

Slippery When Wet

Getting to the bottom of things, so to speak is not always as easy as it appears at first glance. I’d like to share with you an exchange I’ve been having with very articulate correspondent from Chicago…dr dick’s hometown. Pay attention to how the topic moves from a concern about finding the proper lube to issue of much greater importance.

Hey there Dr. Dick,

I’m a 31 year-old gay guy from Chicago, Illinois, and I’ve been in a completely monogamous relationship with my partner, who is 38, for almost nine years.I consider myself to be on the bottom side of versatile–what can I say? I love it when my guy fucks me! But my partner is never able to cum when he makes love to me because of the lube on his dick. For whatever reason, it desensitizes him, and he’s unable to get off either from fucking or masturbation. We’ve tried various brands of lube, as well as different kinds of lotion, but nothing works.

We’re both HIV- and haven’t used condoms for many years. One of my biggest fantasies is to feel him shoot his load inside of me. Unfortunately, he is unable to get to that point. Furthermore, I hate that I get to cum and he doesn’t. I’ve looked for different kinds of lube online, but to be honest, I just don’t know which one might do the trick. Do you have any suggestions?
Thanks, Dr. Dick,
— Daniel

Hey Daniel,

Let me see if I understand what you’re saying. Your partner is unable to ejaculate when he uses either lotion or lube while either masturbating or when fucking you. Right? Does that mean he can masturbate to ejaculation just fine with a dry hand?So when you guys have sex, and he’s fucking you, and you cum, what happens next? Does he pull out of you, wipe off the lube and beat off till he cums?

Daniel, I need a bit more information before I can advise you. I hope you take the time to respond.

dr dick

Thanks for your thoughts on this, Dr. Dick.

That’s right, my partner can’t seem to bring himself to climax using either lotion or lube.He can masturbate to ejaculation with a dry hand. However, I will say that it often takes him a little longer to ejaculate in general, which may just be one of those things that happens to us all sooner or later. He goes wild when I go down on his butt while he masturbates — he usually cums pretty quickly then.

So if there’s no fucking involved, we’ll play around together for awhile, then I’ll concentrate on him until he cums, and then I either jerk off or he’ll jerk me off.

When he’s fucking me, it usually becomes all about me, which I don’t think is very fair, because unless he takes a shower and washes off the lube with soap and water, he can’t cum at all.

He is generally content to just enjoy our love making on these occasions without necessarily having an orgasm. That’s all well and good, but like I said, I don’t think it’s very fair, and I wish I could figure out a solution.

Thanks! Please let me know if you need any more information. I’m looking forward to hearing you’re thoughts on this.
— Daniel

Hello again, Daniel.

This is all very curious. I’d be willing to speculate that what you present here is not merely a wet hand vs. dry hand issue. I took particular note of these comments of yours: “I will say that it often takes him a little longer to ejaculate in general…” “He goes wild when I go down on his butt while he masturbates–he usually cums pretty quickly.” and “… I’ll concentrate on him until he cums…”

First, it’s not unusual for a man not to cum as a top in anal (or vaginal) intercourse. Sometimes there’s simply not enough of the right kind of friction. If, for example, your BF is like another client of mine and his masturbation style is very vigorous, or like my client who is only able to cum by concentrating his manual stimulation on his frenulum, he’ll not cum in anal intercourse…or any intercourse for that matter. He has to get himself off by hand.

You say your BF enjoys being rimmed, and this hastens him to orgasm. Does he enjoy any other butt play, like prostate massage? If he does, you guys could try something like this. You eat his ass while he is masturbating on his back. Using a small vibrating dildo stimulate his prostate. As he approaches ejaculatory inevitability add lube to his dick, straddle him and sit on his dick.This may sound like a whole lot of work, and it may very well be. My suspicion is that your BF has, for whatever reason, talked himself out of every cuming in your ass and the lack of success with traditional anal intercourse has reinforced that. However, if you can help him break down his resistance with a fucking success, some positive reinforcement might turn the tide.

I hasten to add that if what I describe above interferes with spontaneity of your sex play, you may just want to enjoy the sex as you already have it.

Good Luck!

Now that’s really interesting, Doc.
My partner is a bit vigorous when he masturbates, and that’s how he finally gets off 100% of the time. I can’t think of a single other instance when that wasn’t the case. But I just suddenly remembered something he told me a long time ago about his first sexual experience with a dude.

My partner was receiving a blowjob, and as he was cumming, he farted. Now, that particular fart was certainly unfortunately timed — and probably the result of the relaxation that comes with an orgasm — but now I wonder whether or not, way back when, something psychological occurred. I would certainly speculate that switching to masturbation as he’s getting close might not be some kind of mechanism to shift the focus from down there to somewhere else, if you see what I mean.

We’ve never tried any other kind of ass play. I fuck him sometimes, which he enjoys. But we’ve never been much for toys or anything like that. I did get him a latex dildo as a joke one Christmas — nicknamed Gloria, for some reason — but I think I played with that when I masturbated alone more often than when we were having sex. Anyway, Gloria’s gone now — it slowly turned a funny yellow color so we tossed it. A small vibrator sounds like a fun idea…I know I’d use it at the very least!I’m always a little disappointed when our love making isn’t as successful as I’d like it to be, but I’m always careful not to show it, because my partner genuinely feels that he’s not great in the sack — which is nonsense (it really is nonsense).

Sex is always great, and especially between two people who love each other like we do. That sounds a bit trite, but we’re always laughing and doing silly stuff when we’re in bed together, and generally having fun, and I think we communicate well too.I have to admit, we’re not as spontaneous as we would like when it comes to sex. I’m going to go out on a limb and say that lots of couples fall into this trap where the events of the day — work, school for me, dinner, paying bills, answering emails and phone calls, surfing the Internet, booking travel, etc. — gets the better of us, and before you know it, everyone’s tired and ready to fall asleep as soon as their head hits the pillow.

Sometimes, though, if my partner is home when I get home, we’ll find ourselves lying on the bed playing with the cats. When they get fed up with our antics, we usually joke around with each other, talking, laughing, which may or may not lead to sex. It’s great when it does. Other times, especially at night when we’re getting in bed, one or both of us might be horny and we’ll have sex. Many times, I’ll be in the mood but not him, and I’ll jerk off while he rubs my balls and my chest, or he’ll jerk me off, and then go to sleep. That’s about as spontaneous as it gets for us.

Sexual spontaneity is definitely something we both know we need to work on. I’d love to have one of those moments where we have to leave dinner, jump in a cab, and get home ASAP, because we’re so worked up that we gotta jump in bed and play!

— Daniel

Daniel,

Thank you so much for all of this. It’s brilliant. Sounds like you have an exceptionally enviable relationship. Also sounds like you have plenty of room for spicing things up too.It’s so interesting that you mention your BF’s fart incident. I’ve had other people tell me similar stories. Almost to the one, each reported that this single fart incident during sex, altered their entire sexual response cycle for years. Isn’t that amazing? Aren’t we incredible creatures?

All the best,

Dr Dick

April 28, 2006June 3, 2026

INTER GENERATIONAL FUN!

A cluster of email arrived lately from folks in inter-generational relationships. They raise some very interesting issues. Check it out.

Dr. Dick, I’m a 20-year-old lesbian and have been involved in a relationship for a year and a half. She is also 23 years older than me. As much as we don’t want to admit it, our age difference is becoming a problem for us. We have had a difficult and stressful ride for the time we have been together. We are just at different places in our lives. Neither one of us truly wants to break it off; we have put far too much effort into this. I don’t doubt our deep feelings for each other, but is love enough to keep a relationship healthy? I would like to think so, but then of course I don’t have any prior experience. I am young and have many years and many possibilities in front of me. This doesn’t concern me, because more than anything I want this to work. What can we do? – Dena

Dear Dena,

The issues you present get right to the heart of some of the stickiest stuff of human relationships — sex, intimacy and love. Each one of these is different from the other and each satisfies (or frustrates) a specific need in each of us. The problem, of course, is that many of us jumble them all together and make a muddle of things. Let’s see if we can parse things out a bit.

You ask, “is loving someone enough to make a relationship work?” The short answer is, yes, absolutely. The rub comes with defining what that particular relationship will look like. Simply loving someone will NOT be enough to satisfy a need for sexual expression, nor will it satisfy every intimacy need.

That being said, if maintaining your relationship at all costs is your objective, I’d suggest that you consider making some kind of adjustment to your current relationship to allow you to experiment with satisfying your sexual and intimacy needs outside the relationship. Of course, this is often easier said than done.

If your girlfriend is mature enough, she’ll understand your needs and give you the permission you request. If not, you’ll have to do it on your own. You need to grow; so does your partner. Pretending that this issue will somehow disappear, just because you love one another, is foolish. Unattended, these needs will worm their way into every facet of your being together and they’ll destroy everything you currently have in place.

I always favor the up-front approach. Have a frank discussion with your partner. Work out some new, temporary parameters for your relationship. Check in frequently with one another. Take note of how each of you is adjusting to this fresh approach to problem solving. Assure her of her rightful place as your primary partner. All other relationships are merely satellite relationships that are meant to augment what is available on the home front. Of course, you’ll need to grant her the same latitude you seek for yourself. Honesty, communication and assurance will be your keys to success.

Good luck,

Doc, I am 72 years old and I live with a 38 year old young man. Ours is a celibate life but with lots of touch and love. We decided that sex between us could be destructive so we put that aside. We are free to make sexual liaisons outside the relationship, but they have been minimal. We enjoy each other so much without the tension of having to perform that we would like to share the idea with others. We have a freedom that others could cherish. Many have sex without love why not love without sex? I am happy for the first time in my life and suggest these kinds of alternatives in every forum I can. Thank you for your time. – Bill

Dear Bill,

What a joy it was reading your e-mail.

You and I share the same mission. We’re both encouraging others to consider the array of different models of loving, intimacy and sex that are available.

Most of the mail I get is from people who, despite being intelligent and sophisticated in most other matters, have absolutely no creativity in terms of the relationships they form. Just about everyone wants to know how he/she can mimic the look and feel of the dominant heterosexual, sexually exclusive model. As if that were the only legitimate means of being together. Why are gay men and lesbians so eager to buy into a lifestyle that rarely works for straight people? Maybe the wisdom you speak of is that which only comes with age and life experience.

There is one thing I’d like to point out. You say, “Ours is a celibate life…” I think you mean to say that you and your partner live a sexually abstinent life together, correct? Celibacy means something very specific; it means not being heterosexually married. This is a common enough mistake, one that permeates the popular culture.

I applaud your determination to bring the “good news” of alternative models of loving, intimacy and sex to every forum you can. I’m doing the same. Good luck in your efforts. You have a kindred spirit in Dr. Dick.

Dr Dick, I’m currently in a long-term relationship with a man who’s 18 years older than I am. I’m 29. It seems that I want to have sex more often than he does. It may be the age difference between us. I have tried masturbation to relieve my need, but it does not work too well. Whenever I’m with him in bed, I feel like touching him and so on. What should I do? – I Need More

Dear INM,

Congratulations! You’ve discovered the joys of inter-generational relationships. And I see you’ve also discovered the challenges.The issue you present is a common one, even for people dating within their own age group. A disparity in terms of sexual needs often appears between individuals in a relationship. This can be an opportunity for some creative problem solving or it can destroy the whole damn thing.

Here’s my suggestion.

First, try to discover if the difference in need has to do with sex or with intimacy. They’re not the same things, ya know. Does your partner even know that you are withering on the vine? Give yourself permission to explore other options to satisfy your libido. Could you have a sexual playmate outside the relationship? Is a three-way possible? Spice things up with some role-playing or a new sex toy. It’s easy to lose interest in sex when the play is boring, repetitive and ho hum.

There are lots of sex manuals on the market, to be sure. You could consult one of them for ideas if you can’t tap into your own god-given creativity. Of course a less expensive, and I think a more fun way to do this is to visit your local sex emporium. Don’t have one in your town? Too embarrassed to darken the doorway if there is one in your town? Never fear there are loads of them online. Make a date with your partner to visit a store. Pick out something new and naughty for him/her. Let him/her do the same for you.

Remember that sex oughta be an adventure even for an old “married” couple like you. Take all the opportunities that present themselves to make magic happen. You’ll be saving more than your LTR.

Good Luck