Sex Advice With An Edge — Podcast #48 — 01/28/08

[Look for the podcast play button below.]

Hey sex fans,

I have a load of very fascinating questions from the sexually worrisome; and they’re all men this week. What’s up with that? I, of course, respond with an equal number of captivating, witty and oh so informative responses! Hey, it’s what I do.

  • DJ wants to know if it’s ok for he and the hubby to bone one of his patients.
  • Brett thinks his wife is closet bisexual. But he’s just bein’ a guy.
  • James is new at this whole blowjob thing!
  • Ricardo is playing birth control Russian Roulette.
  • Sean and Mel are clueless butt pirates! They should get to know one another.

BE THERE, OR BE SQUARE!

Check out The Lick-A-Dee-Split Connection. That’s dr dick’s toll free podcast voicemail. Don’t worry people; no one will personally answer the phone. Your message goes directly to voicemail.

Got a question? No time to write? Give dr dick a call at (866) 422-5680. Again, the TOLL FREE voicemail number is (866) 422-5680. DON’T BE SHY, LET IT FLY !

Look for my podcasts on iTunes. You’ll fine me in the health section under the subheading — Sexuality. Or just 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.

Say, would you like to become a sponsor for one or more of my weekly sex advice podcasts? As you know, I plug a product or service at the beginning and end of each show. Each podcast has its own posting on my site along with the name of the podcast sponsor and a banner for the product or service.

The beauty part about this unique opportunity is that once a sponsor’s ad is included in a particular podcast that sponsor is embedded there forever.

Your sponsorship also underscores your social conscience. Your marketing dollars will not only got to promote your product, but you will be doing so while helping to disseminate badly needed sex education and sexual enrichment messages. Simply put, ya just can’t get a better bang for your advertising buck!

For further information, contact me at: dr_dick@drdicksexadvice.com

Today’s podcast is once again bought to you by: DR DICK’S HOW TO VIDEO LIBRARY.

drdickvod.jpg

Ace In The Hole

Name: Kevin
Gender: Male
Age: 22
Location: Toronto
I’m just out of college and have a ton of bills and no real job prospects at the moment. A friend suggested I do some escorting to make ends meet. Guys tell me that I’m hot and I like sex, but I don’t know if I could pull it off. Suggestions?

You betcha I have suggestions…a lot of ‘em, don’t ‘cha know.

Being hot and liking sex are great assets if you decide to turn pro, but you’ll need way more than that. Being a sex worker is not like having sex for love or even having recreational sex. You will be exchanging sex for money and that makes it a business proposition. Therefore you’d be wise to approach this with as much forethought as you would any other career move. It is, after all, the world’s oldest profession.

abs.jpgIf you do decide to set up shop, so to speak, you’ll need the capacity to have sex with a much wider range of people than if you were looking for a date. And probably just as important, when there’s an exchange of money, the john becomes your customer. And you know what they say about the customer always being right. The truth of the matter is that all pro sex is client directed. It’s not about you even when it looks like it’s all about you.

So let’s say you’re a really great fuck, fun to be with too. You’ll also need the emotional distance and psychological resilience to cope with the intimacy issues this line of work creates. This is precisely the point where most fledgling sex workers flounder. They either give too much or not enough. Some actually resent their clients for renting them. I know, this is totally absurd, but it happens all the time. This lack of clarity will cause you to have trouble establishing healthy boundaries between you and your john.

Regardless if you are a cheap street hustler turning tricks to support a drug habit or an expensive rent-boy who is servicing the rich and famous, the pitfalls are the same. A lot of sex workers are self-destructive or have huge unresolved sex issues that they try to compensate for by making people pay them for what they usually give away.

If you still think this is a line of work for you, Kevin, be aware that your mind and body are your greatest business assets. Take care of them. Nurture them. Keep them clean, fit and toned. Hygiene, both physical and mental, is a must. Body awareness, not the narcissistic type, and safe-sex practices are your frontline defense against STIs (sexually transmitted infections). Make it your business to be tested for HIV and the other common STIs on a regular (every 3-6 months) basis.

Stay clean and sober while on the job. More sex workers get busted for drugs rather than hustling. Know how to handle a drugged out client. You’ll probably see a lot of those. Know that they can take forever to get off, and can sometimes be paranoid and dangerous.

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Speaking of getting busted; you know this line of work is against the law, don’t you. That of course doesn’t stop lots of people from plying their trade. But the successful ones will have their wits about them, particularly in terms of how they market themselves. Never suggest, in any forum — written or spoken, that you are offering sexual favors for money.

Be fiscally responsibility. Plan for the lean times…and there are always lean times. You’ll probably be a hot property at first; ya know the whole “new meat” phenomenon. Don’t let this go to your head. Count on there being cuter, younger, hotter competitors getting off the bus tomorrow. Try to cultivate a number of regular clients. Have a thought to how and where you will market yourself. And I fully encourage you not to do this full-time, at least not at first. If you find it difficult to meet your financial goals, you’ll be tempted to do more and more risky things just to make ends meet.

Sex work is often more about being psychologically present than a sexual performance. Your clients will often be more lonely and isolated then they are horny. Treat them with respect. Improve your mind. Make yourself interesting. Stay abreast on current affairs and the popular culture. Develop other skills like massage and bodywork.

You should have at least one trusted friend who knows your whereabouts at all times, or who has access to your appointment book. Protect yourself: use a pager or cell phone and never make a date with anyone who won’t share his/her phone number with you. Always make a call back before you head out. Keep an appointment book, in code if you must.

Carry a travel bag or backpack with you to all your “dates”. This should contain the basics: condoms, lube, massage oil, handi-wipes, toys, etc. But you should also have an extra shirt and mace (or other protective equipment). Keep all your belongings — clothing, phone, watch, and wallet — together and near your bag. Know where that bag is at all times and be ready to pick up and leave if there’s trouble.

I also suggest that you connect with other sex workers in your area. There is strength in numbers. Other rent-boys will provide you with essential information about troublesome clients and help you get the lay of the land, so to speak.

Finally, here’s a few of great resource for all sex workers — The Sex Workers Outreach Project, BAYSWAN, AIM and St James Infirmary.

Name: Clare
Gender: Female
Age: 40
Location: St Louis
My best friend can’t bring herself to sever her ties with her ex-boyfriend. Even though their last attempted reunion ended in a very violent fight. My friend has this weird nostalgia for the relationship she had with her ex at the beginning. Back then, before he started drinking and drugging, they did have a couple of good years, but that was a long time ago. I’m very concerned for my friend. She’s often depressed and she is pulling away from her friends. I think she is seriously considering getting back with her no-good, two-timing ex. I know that my role as a friend is to love and support her, but her ex is not to be trusted. I fear as much for her safety as for her heart. What’s a friend to do?

So many things are going on here, Clare. It’s hard to know where to begin. Your friend can’t sever her ties with her ex because she doesn’t want to. Even if she wanted to end it once and for all, it’s not an easy thing to do.

Anyone who has been there will tell ya that quitin’ a bad relationship is as difficult as quitin’ booze or dope…maybe even harder. Most folks in poisonous relationships can’t extricate themselves because they are part of the toxicity. Bad relationships, like the good ones, are completely dependent on the participation of both individuals in the couple. Each one feeds off the other and each one’s bad behaviors rewards and facilitates the pathologies of the other.

domistic_violence02.jpgThere is no such thing as a good, psychologically healthy person in a bad relationship. There may be one in the couple that is less culpable, or less abusive, or less self-destructive, but there is never one that is without blame.

Like all junkies, your friend is hooked. Her depression and withdrawal are outward signs of the pathology. Nothing is gonna change this for her until she acknowledges that she is caught in a downward spiral. Domestic violence — and we ought to label the nature of your friend’s relationship for what it is — will escalate. It always does. Will your friend get out in time? There’s no guarantee. Is there anything you can do? Well that, Clare, is a more difficult question to answer. If you do too much you are at risk of supporting her habit. Or worse, you could be co-opted into the pathological dynamic of the relationship.

The best you can do is to tell your friend how you feel about her predicament. Speak your mind in no uncertain terms. If you decide to confront your friend with an intervention, I suggest that you have some well-considered resources to hand her while you are doing so. For example, you could do some legwork and find a some local domestic violence resources — a hot line, a shelter, counseling referrals and the like. Once you make this intervention and it’s over; drop it. Drop it for good. This is the hardest thing a friend has to do, but constantly badgering someone in your friend’s condition is counterproductive. If you can’t stand to witness the self-destruction, take your leave of the friendship and hope for the best.

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However you play this, don’t hold your breath for a happy ending. They happen sometime, of course, but real life is so not like the movies.

Name: Dena
Gender: Female
Age: 32
Location: NYC
I love my cunt. In fact you could say I have a cunt fetish. I love to stuff my cunt with really big toys. My current BF introduced me to fist fucking and I love it. I guess what I want to know is can this be dangerous?

I love it, a chick who refers to her pussy as a cunt! You go, girl!

But what’s this…you’re just now gettin’ around to askin’ if fisting is dangerous? Not before, but after you’ve had a fist in your cunt? Well, so much for being proactive. I’d be willing to guess that you probably already have some data on the advisability of this form of extreme sex play. You clearly have enough information to declare that you LOVE IT.

hanball2.jpgOk, for everyone in my audience who hasn’t heard of fisting (both those with a cunt and those who are cunt-less), let’s start at the beginning. I trust you know what fingering is, right? Whether it’s fingerin’ a pussy or an asshole, it’s loads of fun to diddle someone’s innards. We already know that fingerin’ a dude’s hole will stimulate his prostate, which even non-gay men are finding to be way fun. And fingering a pussy will stimulate a woman’s G-spot. Ok sex fans; take that fingerin’ concept and multiply that by 5. That’s right, fisting is inserting a whole hand/fist into cunt or asshole.

For all you folks who haven’t fainted away, yes, it is anatomically possible, and yes, it CAN be EXTREMELY pleasurable. I hasten to add that gettin’ a whole fist inside a pussy is somewhat easier than gettin’ a fist in an asshole. But for folks like you, Dena, those who are into massive penetration, nothing is a bigger turn-on. Fisting aficionados say that handballing is the most intimate and complete way to touch another human being. This kind of extreme penetration has to be worked up to slowly and gently.

To your question if this practice is harmful…well not if ya do it right. First off, the fisting top does NOT make a fist and ram it home. Trust and communication between partners is as essential as is tons of lube. Some folks swear by Crisco, others the legendary J-Lube — a handy-dandy concentrate for veterinarian use. They believe this product stand apart from the rest because it’s more slippery and gooey. You can find J-Lube in Dr Dick’s Stockroom. See the My Stockroom tab right there at the top of this page. How freakin’ convenient is that?

The fisting top must, of course, respect his/her partner’s limits and pain threshold. Safe fisting is happy fisting. And to that end, keep the following concerns in mind.handball1.jpg

First of all, the fisting top must cut and file all his/her nails until every finger is as smooth as it could possibly be. Your fingers will be in some very delicate places — places that may not have pain receptors. You’ll want to insure that you minimize all chance of causing injury.

Make sure your partner is relaxed, comfortable and turned on. When a woman is aroused, her pussy lubricates, relaxes, expands and lengthens; all of which are very important for accommodating a fist, don’t ‘cha know.

Even the wettest cunt in the world will need lots and lots of lube during fisting. There’s no such thing as too much lube, so prepare for a big fat mess. Lube your hand, the back of your hand, between your fingers. Keep applying lube as you go. Push the lube into the pussy (or asshole) with your fingers. Remember if you’re using latex gloves, oil-based lubes will dissolve latex.

Start with one or two fingers and work your way up to three and then four. Most people need some time to further relax their muscles, and some may require several stretching sessions, over weeks or even months, before they can actually accommodate a whole hand.

Tops, be sensitive to your bottom’s feelings. You are trying to finesse part of her body to open and to admit part of your body deeply inside her. If you take your time, the energy exchange between you and she will move you both into an altered state. Communication and relaxation is key.

handball_self.jpgOnce you’ve reached a five-finger insertion, you’re almost there. But it’s at this precise point that the handballing top needs to be the most attentive. Your partner’s pussy is being stretched to its near limit. Your partner is going to be riding a wave of pain/pleasure. If you find her cunt has reached its limit for the time being, respect that and pull out slowly. But if your partner wants more, then slip your knuckles inside. Be sure to fold your thumb under your fingers, so that your hand will form a duckbill wedge shape. This will allow you to gradually stretch your partner open as you press on. Apply steady but slow pressure.

Your partner should tell you when to push and when to back off. Careless fisting can cause muscle and tissue injuries. If the top goes too fast or too hard there’s gonna be more than discomfort, there will sure enough be injury. Listen to the owner of the pussy; she will let you know the difference between hurts so good and hurts really bad.

Your knuckles are the widest part of the hand and the most difficult part to get past the opening of the cunt. If there’s gonna be resistance to the insertion of the fist, it’ll probably be at this point. Wait until your partner is ready before making the big push. She may be able to help by bearing down (like if she were birthin’ a baby, or taking a big dump). Once your knuckles slip past the ring of muscles around the vaginal entrance, the pressure will ease off. Now you can gently roll your duckbill shaped hand into a fist.

At this point, the owner of the pussy or asshole may want a gentle pumping movement with your hand. Fisting can produce extremely intense sensations; so ask her what feels good to her.

When the session is done, make your hand into the duckbill wedge shape once again, and gently slide it out slowly.

Good luck ya’ll

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Sex Advice With An Edge — Podcast #47 — 01/21/08

[Look for the podcast play button below.]

Hey sex fans,

I have a nice load of provocative questions from the sexually worrisome. And I respond with an equal number of astounding, amiable and oh so informative responses! Hey, it’s what I do.

  • Amy’s vibrator don’t work no how!
  • Dan is dating a woman with a blockage. But what kind of blockage?
  • Jon’s meds eliminates his spooge output. Pity that!
  • LD’s partner died, but he wants to get back in the swing of things.

FINALLY, ANOTHER SEXUAL ENRICHMENT TUTORIAL

  • The Big Tease; How to Strip for Someone Special

BE THERE, OR BE SQUARE!

Check out The Lick-A-Dee-Split Connection. That’s dr dick’s toll free podcast voicemail. Don’t worry people; no one will personally answer the phone. Your message goes directly to voicemail.

Got a question? No time to write? Give dr dick a call at (866) 422-5680. Again, the TOLL FREE voicemail number is (866) 422-5680. DON’T BE SHY, LET IT FLY !

Look for my podcasts on iTunes. You’ll fine me in the health section under the subheading — Sexuality. Or just 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.

Say, would you like to become a sponsor for one or more of my weekly sex advice podcasts? As you know, I plug a product or service at the beginning and end of each show. Each podcast has its own posting on my site along with the name of the podcast sponsor and a banner for the product or service.

The beauty part about this unique opportunity is that once a sponsor’s ad is included in a particular podcast that sponsor is embedded there forever.

Your sponsorship also underscores your social conscience. Your marketing dollars will not only got to promote your product, but you will be doing so while helping to disseminate badly needed sex education and sexual enrichment messages. Simply put, ya just can’t get a better bang for your advertising buck!

For further information, contact me at: dr_dick@drdicksexadvice.com

Today’s podcast is once again bought to you by: Eden Fantasys — for all your adult toys!


Can U Squeeze Me In

Name: Jim & Elaine
Gender: Couple
Age: 42 & 38
Location: Denver
We have been happily married for 15 years. We have a good, but pretty vanilla sex life together. We want to spice things up and are talking about maybe looking for other couples online. We’re both in good shape and have very outgoing personalities. Both of us have had one short affair in the past, now we think we want to play together. Thoughts?

You guys want to look for other couples online…for ummm sex? I mean you imply that but you don’t really come right out and say it, do you? I know you are new to this and you are just feeling your way through this unfamiliar territory, but unless you want to look like rank amateurs by other swingers…and that’s what we’re talking about, swinging, right? You’d better get comfortable articulating precisely what it is you want, how you want it and with whom.

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If you’ve already begun your online search, you’ve probably already discovered that there are several different avenues for you to pursue. There are, of course, dating and profile sites. There are sites that feature ads from other swingers. For example you could check out craigslist for the generic variety. Then there are exclusive swing parties and more inclusive swinger clubs. And each of these outlets may offer special groupings for the fetish-oriented swinger.

Before you swing, you guys need to decide what type of swing-set you want. If the vocabulary that follows is unfamiliar to you, you have some remedial homework to do before you launch your swing-capade. There is “soft” swinging and “hard” swinging. Bisexually may or may not be an option for you.

If you assume that all swingers are open-minded about sex, consider this; lots of swing outlets prohibit male-on-male sex. Personally, I find this extremely bizarre. But I suppose it only underscores the prejudices of the popular culture. There are some swing-sets that allow novice swingers to simply to be voyeurs. I can’t fuckin’ figure that out either. Maybe it’s a heterosexual thing.

If you gravitate toward the club-set there are 3 types to consider:6190_01.jpg

  1. SEX clubs — these clubs allow full-on sex, but only in designated areas.
  2. NO-SEX clubs — allow for lots of exhibitionism and voyeurism, including nudity, but no full-on sex. These clubs are great for meeting other swingers and to set up your own sex dates.
  3. Swinger parties are NO-SEX events, and are usually held in a nightclub or restaurant. Again, you can meet like-minded folks there and set up your own sex dates.

Whichever outlet you choose; make sure you understand all the rules and regulations of the get together before you decide to attend.

Like I said, it’s of the utmost importance that you guys decide, in advance, what your limits are. A good number of otherwise healthy marriages flounder at this point. Have a clear and frank exchange with each other on the ground rules of your swinging and then stick to them. Negotiating a change to the rules of engagement during a swing is a very bad idea. That’s not to say that your ground rules won’t change and evolve over time; just don’t attempt to adjust them while they are in play.

Never push your partner into doing something he/she is not ready to do. Be open with each other before, during and especially after a swing. Effective communication is essential. This goes for communicating with your fellow swingers. Be sure to let everyone know that you are newbees to the scene. (Don’t worry, everyone will already know.) Novices stick out like a sore…hardon.

Most clubs and groupings don’t allow single men. Most swing-sets are women oriented, to the degree that women set the tone for the swing. That being said, it’s still a man’s world. Men generally dictate the type of sexual expression that will be tolerated — thus the prohibition, stated or unstated, against male on male sex. Female on female sex is, of course, encouraged for obvious reasons. How’s that for a screwed-up double standard?

Most clubs expect full or partial nudity. My swinger friends advise that if you just want to attend so you can ogle others, stay the fuck home! Novice swingers, like you guys, ought to stay together until you feel comfortable being apart. But for Christ sake, don’t glom on to one another like the other swingers have the cooties.

Most of all, take responsibility for your eroticism and your sexuality. Be friendly and good-natured. And don’t try to pretend you’re a more accomplished sexual athlete than you are.

Be advised, you are about to embark on a sexual journey that will take you to the edges of what society regards as appropriate sexual behavior. Don’t be surprised if some of your more traditional friends discriminate against you when they find out about your new activities. Finally, swinging is far less about what you do (sex) and way more about who you are (a lifestyle). To that end, I’d like to turn you on to a fantastic resource. Check out my friends, John and Allie, at SwingerCast. Be sure to tell them dr dick sent ya!

Name: Nathan
Gender: Male
Age: 37
Location: Dallas
I’m a married guy with a great wife and 3 beautiful kids. A couple of weeks ago, I went to a masseuse I found on craigslist. I don’t have a lot of experience with massage and thought I would be safe going to a guy instead of a woman. The guy was really nice and did a good massage, but somehow I popped wood near the end of the massage. I was really embarrassed, but he was like totally fine with that. Then he asked if I wanted a happy ending. I didn’t even know what that was till he started to massage my ass and blow me. I have to admit it was totally amazing. I never felt anything like it before in my life. My wife sometimes will give me oral sex, but nothing like this. I blew a load like nothing I ever did before. I though my insides were coming out of my cock. I was wowed and scared and confused and I could hardly sit up. Then the guy said I had a real healthy prostate. I said what? And he said he was massaging my prostate while he was sucking me off. I can’t stop thinking about this. I want more but I feel really guilty and I’m afraid this is going to make me gay.

What a fabulous story, Nathan. But we need to clear up a few things. A masseuse is a female practitioner of massage. A masseur is a male practitioner. This is a common enough mistake, but I thought you should know the proper usage for further reference. Because you can see how a little unintended slip like this will make all the difference in the world. If you say a masseuse gave you a blowjob that’s totally different from getting a blowjob from a masseur, don’t ‘cha know.

chimp_prostate_exam.jpgI’m gonna also guess you never had a prostate massage before this encounter with the masseur. A prostate massage coupled with your first blowjob from a guy…hell, you are lucky your insides didn’t shoot out your dick along with your spooge. I’m joking of course, but it does stand to reason that you had such an intense and explosive orgasm and ejaculation. That’s precisely what prostate massage does, honey.

Now, let’s see if we can figure out why you can’t stop thinking about this. It doesn’t take a rocket scientist to analyze that either. This was a peak sexual experience for you. I mean, beside the mind-blowing release, the means by which you had this orgasm — the guy’s finger in your ass and the guy’s mouth on your dick were both unexpected and apparently unprecedented. So I figure you had very little time to cognitively respond to the stimuli before things came to their explosive climax, as it were. And you did say you were already relaxed and aroused by the massage, right?

I’d be willing to bet that if you had some emotional distance from the experience you would realize your body was simply responding to the stimulus it was receiving. Your dick and your prostate weren’t able to distinguish the gender of the person diddlin’ your ass and blowin’ you. And since your brain was occupied with all these new sensations you had little time, if any to process and possibly protest. And maybe you wouldn’t have protested even if you could. Maybe you wanted to take this little walk on the wild side. Tust me, lots of guys do.

Now that the event has passed, you have plenty of time to process. And process you are…to withinprostate_massage.jpg an inch of its life…if ya ask me. This experience looms so large for you because it is forbidden fruit, so to speak. It upsets the apple cart of your cozy and predictable heterosexuality. I mean it’s one thing to pop wood on a massage table. It’s something totally different to blow a wad while a guy is givin’ you head.

And now that you have all this time on your hands to keep pouring over and over this in you head, the event is taking on a proportion it probably wouldn’t have otherwise.

prostate_massage_copy.jpgLet me put your mind to rest, one blowjob from a guy…even an earth-shatterin, prostate massagin’ blowjob, like the kind you got from this fabulous masseur…won’t make you gay. Nor does wanting to repeat the experience make you gay. All this experience really tells us is that you like a good blowjob and you now know where to get a really fantastic one when next you want one.

Think about it this way. Say you went to a Chinese restaurant and, to your great surprise, had the best dim sum ever. You were so impressed with the food that you’ve been eager to return to this particular eatery for another go at those tasty vittles. Does this desire for yummy dim sum make you Chinese? I don’t think so…unless, of course, you were Chinese before you went to the restaurant.

Finally, the guilt you’re experiencing, where might that be coming from? There are so many sources one would be hard-pressed to come up with an exhaustive list. But let’s look at the top contenders.

  • You’re married with a family. You had a sexual experience…unplanned as it might have been…with someone other than your wife. BINGO!
  • Our culture’s buttoned-down sex and gender stereotypes — who can do what to whom. BINGO!
  • The dictates of our sex-negative society about what is proper and what is not in terms of sexual exploration and experimentation. BINGO!
  • The shame of possibly being labeled a fag. BINGO!
  • The fear of your own desires and where they might lead you. BINGO!
  • The allure of the forbidden and the explosive charge the illicit. BINGO.

The experience you had with that masseur, Nathan, is so highly charged, both culturally and sexually that it will take some while for you to find your balance once again. In the interim, my I suggest that you postpone any judgments about yourself or what the indecent might imply about you until you’ve have some emotional distance and the time to calmly process all of this. In the final analysis, I think you’ll come to the conclusion that this is a relatively harmless sexual outlet. The masseur is providing you a service…I mean beyond the obvious. He is providing you a safe, secure non-judgmental environment to exercise and expand your sexual repertoire. Think of it like a place you go to learn about the wonders of sexual dim sum.

Name: Rebecca
Gender: Female
Age: 24
Location: Cincinnati
Last year I had a sexual relationship with a guy I met through work. We kept it light and had some fun. He has since relocated to another city, but we keep in touch and hook up whenever he’s in town. The last time he was here he asked if I would ever consider a threesome with him and one of his male friends. I told him I might consider it if I knew the other guy. As it turns out, the other guy and I went to the same college. I know, small world, huh? The idea of having a 3-way with these two guys is totally hot; I’m attracted to both of them. Even though this would be a first for me, I would like to give it a try. I guess my question is what should I look for in this kind of situation?

What should you look for in this kind of situation? Why, look for double the fun, you little vixen you! You sound like you’re a pretty savvy chick when it comes to sex, Rebecca. I suspect you’ve been around the block a time or two. Good for you. You also seem to know what you want and how to go about getting that, kudos to you on that.

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Trying new things can be really fun especially when your playing with people you like and are turned on to. I’d suggest you keep the event light and breezy. Too many people try to script a 3-way to within an inch of its life. And that can fuck up the whole damn thing. At the same time, just hooking up for quick shag can be a little too impersonal when it comes to 3-ways.

Luckily, there’s another way. I suggest the three of you start your encounter by getting a bite to eat together. A little food and a few cocktails can be a great start to the adventure. No doubt all three of you will be a little nervous, so make this part of the outing light, sexy and flirtatious. Practice your seduction skills on each of the guys. You will soon discover the sexual hierarchy…and there always is one in these kinds of encounters.

If there are any ground rules, this is the time to mention them. The more you discover about the guys in this non-sexual environment the more prepared you will be for how the rest of the evening will play itself out. If I were you, I’d want to get a sense of how experienced the two guys are at having a 3-way. Do you happen to know if the guys are bisexual? If they are, you can be assured that the 3-way dynamic will be fundamentally different than if they guys are not bi and only want to shower their hot monkey-love on you. Maybe you could ask about their sexual fantasies and share some of your own. Just remember, you are an equal partner in this ménage. I’d make sure that the fellas knew what turned you on. Fortunately, you have the advantage of having already played with the one guys; so that should make things easier.

I hope you write back and let me know how the encounter went. My interest, of course, is purely scientific, don’t ‘cha know. But I will want all the gory details. And a detailed photo essay would also be deeply appreciated. 😉

Good luck ya’ll

Sex Advice With An Edge — Podcast #46 — 01/14/08

[Look for the podcast play button below.]

Hey sex fans,

I have a might big load of thought-provoking questions from the sexually worrisome. And I respond with an equal number of dazzling, charming and oh so informative responses! Hey, it’s what I do.

  • Seattle Guy has way too many questions, some of which are the wrong ones.
  • Dan and Rebecca wanna cum together.
  • Erin, Joy and Gene get quickies.
  • James has been fucked up for 25 years…or more.
  • S’s BF is hung like a horse! What could be the matter with that?
  • Alx has a thing for her older brother!

BE THERE, OR BE SQUARE!

Check out The Lick-A-Dee-Split Connection. That’s dr dick’s toll free podcast voicemail. Don’t worry people; no one will personally answer the phone. Your message goes directly to voicemail.

Got a question? No time to write? Give dr dick a call at (866) 422-5680. Again, the TOLL FREE voicemail number is (866) 422-5680. DON’T BE SHY, LET IT FLY !

Look for my podcasts on iTunes. You’ll fine me in the health section under the subheading — Sexuality. Or just 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.

Say, would you like to become a sponsor for one or more of my weekly sex advice podcasts? As you know, I plug a product or service at the beginning and end of each show. Each podcast has its own posting on my site along with the name of the podcast sponsor and a banner for the product or service.

The beauty part about this unique opportunity is that once a sponsor’s ad is included in a particular podcast that sponsor is embedded there forever.

Your sponsorship also underscores your social conscience. Your marketing dollars will not only got to promote your product, but you will be doing so while helping to disseminate badly needed sex education and sexual enrichment messages. Simply put, ya just can’t get a better bang for your advertising buck!

For further information, contact me at: dr_dick@drdicksexadvice.com

 

Loose Change

Name: Tia
Gender: Female
Age: 19
I have a problem. I’m still a virgin, but my bf thinks I’m not. It’s really my fault he thinks this, cuz I told him I was all experienced and everything. We’ve been going together for about 8 months already and I really want my first time to be with him, but how am I going to act all experienced when I don’t know what I’m doing.
HELP ME PLEASE!!!

That sure enough is a pickle you got yourself into darlin’. You’ve got some ‘splanin’ to do Lucy!

Funny, because I’m more likely to hear from young women who are not virgins, but who want to know how they can fool a new partner into thinking they are. I guess we can chalk up all this deception and confusion to the powerful associations every culture imposes on virginity…female virginity, that is.

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Like most things sexual there is a huge double standard between the cultural and individual importance of virginity for women as opposed to men. Cultural expectations about virginity are also tied to age as well as gender. For example, our society expects its 16-year-old girls to be virgins. To be otherwise, at that tender age, would be a scandal in most communities. (Jamie Lynn Spears comes immediately to mind.) But a 35 year old woman who is still a virgin is considered an old maid — or worse, a dyke.

Of course, things are more fluid when it comes to boys and men. On the one hand, a 16year old boy who is not a virgin may raise some eyebrows in some communities. But many others in those same communities would praise him for being a stud. On the other hand, a 35 year old man who is still a virgin is the butt of jokes — or worse, a queer. In fact, he’s also more of a disgrace to his gender than an old maid is to hers. Funny how that works, huh?

I hasten to add that there is a lot to argue with in terms of these arbitrary cultural norms, and I encourage ya’ll to argue away. God knows I do! And you don’t have to buy into them either. God knows I don’t! But till things change, these norms are the norms, like it or lump it.

I’d love to know why you felt the need to deceive your BF in the first place? Do the people you hang with, prize sexual experience over sexual innocence for a young woman of 19? And what are the expectations of your group regarding a 19 year old guy? I’ll bet the expectation is that he not be a virgin. Right?

Well you can see why a lot of people, not just you Tia, find this whole thing just too damned complicated. And rather than add to the confusion or the deception, I encourage you to come clean with the BF about your cherry.

Here’s why I think this is the best policy. First, if the BF is sexually experienced, it will be very difficult for you to hide the fact that you’re not. Besides, like you said in your message to me. “I really want my first time to be with him.” Why not just come out and tell him that, sweetheart? No man is gonna turn that down…ever. Simply put, that is the most sexually charged and treasured sentence in any language.

Begin the big talk with your man like this. “Baby, I got something real special to tell you. You know how I’ve been sayin that I’ve been with other guys and everything? Well that was just my way of keeping all the other guys from pestering me for my junk. Baby, the truth is that I haven’t had sex before now. And the best part of this is I’ve decided that I really want my first time to be with you. My cherry belongs to you, baby”

Like I said, Tia, no man is gonna turn that down. The BF will be so flattered you won’t have to pretend to be something you’re not. Clearing the air like this will also allow you to relax when the magic moment finally happens. And relaxation is the key to enjoying yourself. And you should enjoy yourself.

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 have a preference for either natural or snipped meat, so I’m cool with that. Sometimes the preference is even culturally induced. Ok, fine! I also know that some guys prefer what they don’t have. Lots of clipped men like uncut cock, and lots of natural 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?

cock-buffet.jpgI 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 to ask outright. Ok, so far so good.

What I don’t understand about your question is that you think it might be whorish to be up-front and ask a guy about the condition of his trouser snake. Like, WHY? Either you don’t understand the meaning of the word “whore,” or you’re too self-conscious about taking responsibility for your personal tastes in tonsil ticklers . 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. 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.

Name: William
Gender:
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! Last week I published my long-awaited: Finessing That Ass Fuck — A Tutorial For a Top. Check it out! It’ll answer a lot of the questions you have about butt fucking.

But before you take off to read that, 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 issex_toys_dj212901.jpg essential.

Do you know what a cockring is, William? If not, I suggest you acquaint yourself with these amazing low-tech wonders. Here’s what you should do. Turn your attention to the Eden Fantasys banner at the top of this page. Click through that link and go to the Sex Toys for Men section. Look for Erection Help there you will see the link to cockrings. Prepare yourself to be sorely amazed at the variety and functionality of these little devils.

Cock rings can create larger and firmer erections. Since blood flow enters your dick through arteries deep inside your dick, and leaves it through the veins nearer the surface of your schlong; wearing a cock ring can help to sex_toys_gef90178bs.jpgkeep more blood inside your dick shaft. And as all you rocket scientists know, blood flow is what causes erections in the first place. Also some men claim that wearing a cock ring intensifies their orgasm.

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 put a rigid one on.

  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 one of these little buggers on before you have a raging hardon is gonna be 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!

NEXT, ANOTHER SEXUAL ENRICHMENT TUTORIAL

Beginning Sex Play — Tips and Techniques

The most frequent questions I get are from your average dick and jane, (or dick and dick, or jane and jane) who want to spice up their sex life. Inevitably they describe the kind of sex they’re currently having. And almost universally the description makes this grown man cry. Jeez, the boredom. How do they stand it? It’s a wonder any of them are having any sex at all.

What is it with the humdrum, run of the mill, we’ve always done it that way mentality? Are ya’ll afraid that if you add a little something new to your sex chore. from time to time, that the sky will fall? Holy cow!

Today’s tutorial is another attempt to motivate you to get off your butts and make something interesting happen in the sex department. We’ll begin with what was once called foreplay.

First off, I hate the word “foreplay” because it suggests that all these really great sex activities are only a lead up to a single — “more important” activity — fucking. It also implies that ya’ll can dispense with the one in order to hurry up and get to the other. And that, my friends, is always a huge mistake.

do-not-disturb.jpgFrom now on I want us to banish “foreplay” from our vocabulary. Instead let’s start using “Beginning Sex Play”. It says it all. It says it’s at the beginning, but there’s no suggestion that anything in particular must follow.

I’m of the mind that we’d all be better served if we thought of sex play as a continuum of pleasure and pleasuring — with a beginning, middle and an end. If you ask me, our sex play ought mirror our sexual response cycles — arousal, plateau, orgasm and resolution. That way we’re less likely to overburden one particular activity at the expense of all the others. Get it? Got it? Good!

Experienced sex fans agree; the best sexual encounters include an extended period of sensual play at the beginning of most sex play. This brings increased pleasure to both partners, and will make whatever else that might follow more satisfying. Just remember, beginning sex play can be a meal in itself.

Beginning sex play brings spice to the encounter because it gets our motors started. Even all yousex_toys_rd9613.jpg major sex athletes out there who are perpetually primed for sex will benefit from some hearty beginning sex play. It will help cool your jets and make the encounter last longer than a firecracker. And I know that you know what I mean!

In our hectic rush around world, beginning sex play is particularly important. It helps us transition from the daily cares and woes to the realm of sensual pleasures. The workaholics among us need more time to become fully aroused. Their minds are still filled with the junk of the day, and not yet ready to give or receive pleasure. And pleasuring and being pleasured takes a big attitude shift from that of the rest of the day. In fact, if you’re gonna approach sex and pleasuring with the same mindset you have on the job or with the kids, give it up now and be done with it. You’ll only walk away from the encounter disappointed.

sex_toys_ki0001.jpgBeginning sex play primes us for maximum pleasure. Men will have the time we need to come to full erection and women will have the time they need to properly lubricate. By the way, this is called the arousal stage in our sexual response cycle. But you probably know that already, right?

When we stop thinking of beginning sex play as “foreplay” we realize there is no such thing as spending too much time giving and getting pleasure. If beginning sex play evolves into full-on fucking — SWELL. Both partners will be fully aroused and fucking will flow naturally and effortlessly from the pleasure enjoyed at the beginning of sex play.

Beginning sex play can include everything from chocolate and whipped cream to whips and chains. But let’s not get too far ahead of our selves. Let’s start at the beginning of beginning sex play. Most people miss out on the pleasure of undressing with and for their partners. Stripping out of, or being helped out of our daily wear and into something sexysex_toys_ks0092.jpg or nothing at all can be very arousing. It’s also a visual signal that we’re shifting out of our work-a-day world and entering the realm of sensuality. Stripping is an art form, ya know. We could all learn a lesson or two from the folks who do this for a living, but more about this in a later tutorial.

Creating the right sex environment is important too. Make sure the room is warm. Proper lighting and music will surely add to the mood. Scents are also important. More and more people are incorporating erotica into their sex play — reading a sexy story together or enjoying some hot porn will make the encounter memorable.

Most women complain that their partners don’t kiss long enough and rush the kissing to get at their pussy. Guys, what the fuck? You want pussy? Use your mouth to maximum advantage kiss and nibble all over everything. Literally devour your partner with your mouth. Believe me, if you do this right, by the time you get to her pussy she’s gonna want sex_toys_055337396x.jpgto give it up big time.

Beginning sex play is the perfect time for setting the mood for all that might follow. It’s a time for sharing fantasies, role-playing, dirty talk or some full body massage. Always have some nice lotion available then use your hands, forearms, feet and elbows to knead your partner’s muscles and naughty bits.

Certain areas on the body are more hot-wired than others. It’s your job to find each and every one your partner has. As you massage vary your strokes and touch to stimulate your partner. Roll your fingertips across his or her nipples and behind his or her ears as you kiss him and tease her with your tongue.

If you’re doin things right, your partner will be moaning with pleasure. If she or he starts getting impatient it’s time to bring out the restraints. There’s nothing like some hot erotic bondage to punctuate your beginning sex play.

While your darling is subdued and possibly blindfolded, crank things up a notch. Add differentsex_toys_ss34047.jpg
sensations and stimuli, a warm chocolate sauce followed by ice cream. A fur mitt followed by a Loofah. Introduce some sex toys — a vibrator, tit clamps, or an anal stimulator.

Don’t forget to check in with your partner from time to time. Ask for some feedback and direction. Do you like this? Or do you like this better? Never presume to know what your partner likes simply because he or she liked it before, this is a recipe for boredom and the dreaded bed death. If words fail you, SHOW your partner what you want. Then encourage your partner to do the same to you.

sex_toys_se259600.jpg

Beginning sex play is not about pressing the right buttons in the right order. It is about understanding what makes your partner tick and supplying and applying those things to their greatest sensual advantage. There are many ways to give your partner extreme pleasure, and it all begins in your brain. Beginning sex play is as much of an art form as it is a necessity.

Finally, the basic premise behind all of this is that a great lover is one that gives pleasure because it is its own reward, not a means to getting something else.

Good luck ya’ll

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Sex Advice With An Edge — Podcast #45 — 01/07/08

[Look for the podcast play button below.]

Hey sex fans,

Today is my first podcast of the New Year. I have a really delectable show for you today. We have a great big load of stimulating questions from the sexually worrisome. And I respond with an equal number of stunning, appealing and oh so informative responses! Hey, it’s what I do.

  • Ashley wants to squirt for her BF.
  • Young Troy keeps bangin’ away, but he oughta try a different approach.
  • Ralph has a bone to pick with the red hankie crowd.
  • Jayrol wants a wife, kids and a white picket fence. But wait, there’s a rub!

BE THERE, OR BE SQUARE!

Check out The Lick-A-Dee-Split Connection. That’s dr dick’s toll free podcast voicemail. Don’t worry people; no one will personally answer the phone. Your message goes directly to voicemail.Got a question? No time to write? Give dr dick a call at (866) 422-5680. Again, the toll free voicemail number is (866) 422-5680. DON’T BE SHY, LET IT FLY!

Look for my podcasts on iTunes. You’ll fine me in the health section under the subheading — Sexuality. Or just 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.

Say, would you like to become a sponsor for one or more of my weekly sex advice podcasts? As you know, I plug a product or service at the beginning and end of each show — just like I’m dong now. Each podcast has its own posting on my site along with the name of the podcast sponsor and a banner for the product or service.The beauty part about this unique opportunity is that once a sponsor’s ad is included in a particular podcast that sponsor is embedded there forever.Your sponsorship also underscores your social conscience. Your marketing dollars will not only got to promote your product, but you will be doing so while helping to disseminate badly needed sex education and sexual enrichment messages. Simply put, ya just can’t get a better bang for your advertising buck!For further information, contact me at: dr_dick@drdicksexadvice.com

Today’s podcast is once again bought to you by: Eden Fantasys — for all your adult toys!

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Merrily We Roll Along!

Hey sex fans,

I hope ya’ll survived the holidays. I did! Although I can’t tell you how glad I am that all that nonsense is over.

Before we begin, I just want to remind you that my podcasts will resume next Monday, January 07. I have a slew of interesting questions that have been piling up over the past couple of weeks. So I can guarantee you it will be a juicy podcast. Don’t miss it!

Name: Fay
Gender: Female
Age: 23
Location: LA
I met this guy on the Internet and he seemed nice and all, but I wasn’t that turned on to him. All I remember is he was pretty nerdy and had really sweaty palms. We went out a couple of time, nothing serious. He just wasn’t my type. So I stopped responding to his calls. Last week I was out at this club with some friends and I saw Mr. Nerdy with this other chic. And I was like, wait a minute, that skank’s hornin’ in on my stuff! I know I wasn’t returning his calls, but still, I saw him first. It was like totally freaky, how they were all kissy-kissy right there in everyone’s face. What should I do?

Seriously? What should you do? How about getting a life. you vacuous twit? And Iwoman_screaming.jpg mean that in the nicest sort of way.

If you could just pull your head out of your ass long enough for you to listen to yourself; your misguided notions about dating and your fundamental lack of respect for the feelings of others would surly grate on you as much as it does me. Your mindless chatter is like fingernails on a blackboard. I mean REALLY!

Think about what you are suggesting here. You’re gettin’ all territorial about some guy you could barely bring yourself to give the time of day to and then blew off like he was excess baggage. You didn’t bother to take the time to look beyond his nerdy-ness and his sweaty palms like this other woman have done. Had you done so, you might have discovered what this other “skank,” as you so lovingly refer to her, has found. But ya didn’t!

Like most nerds, this guy probably developed other means of making himself attractive and interesting to compensate for his nerdy-ness. Maybe he’s got a big ol’ dick, or he’s great in the sack. Maybe he got a big bank account or maybe he simply has a handle on the basic social graces, something that you, dear Fay, have yet to grasp.

Your jealousy is neither cute nor charming. It does, however, mark you as self-centered and childish. For the most part, jealousy is a byproduct of a person’s lack of self-confidence and self-esteem. Here’s a tip: try and develop a healthier sense of self, so that you’ll mature into someone who can interact with others in a respectful manner that is befitting another human being.

Oh, and have a nice day!

Name: Joanne
Gender: Female
Age: 25
Location: Toronto
I’m 25, 5-foot-7 and weigh 105 pounds. I take care of my body by eating right and exercising regularly. My problem is that I hate the way I look. I am actually repulsed by my body. I take very brief showers and avoid the mirror as much as possible. I’m not a prude. Others being nude is fine with me. But my body image issues are hindering my sexual encounters. I always want to wear a shirt or have the lights off.

My current boyfriend says that if I trust him enough to sleep with him I should trust him enough to let him see me naked. He also has told me that we can’t continue seeing each other if this doesn’t improve. But I let him see every part of my nude body — just not all at once. So he knows I’m not hiding some monstrous deformity or anything. I guess I thought my boyfriend would be more sensitive to my fear and let me stay covered up. Do I owe him nudity?

Hold on there, girlfriend, you think your BF is being insensitive because he wants to enjoy your body in the buff…with the lights on? You think that he’s sticking around just to needle you about your phobia? Honey, get over yourself!

Do you honestly think that your body-positive BF oughta facilitate and participatecrystal_pussy.jpg in your pathology? Yeah, like why don’t we all just sink to the lowest common denominator? And here’s a tip, doll: you do have a monstrous deformity. Perhaps it’s not a physical deformity, but it sure enough is a psychological one.

I concur with your boyfriend; your relationship is on the line here. You need to get a handle on your hang-ups, darlin’, or you can just say good-bye to whatever sex and intimacy you may currently be enjoying.

Listen, I have a thing about sex and intimacy being a gift one gives another. So I ask you, how can you give yourself as a gift to anyone if you are disgusted with the gift you’re giving? And you’ll never convince me that your body issues aren’t seeping into and sabotaging the sex you may be having with your long-suffering BF. I’ll betcha you don’t let him get too close to the body parts you begrudgingly expose to him…when the lights are out.

Joanne, like I suggest above, being repulsed by your own body is a sign of a deep psychological problem. I’d suggest you get to the bottom of this with a sex-positive therapist right away.

When I encounter this sort of thing in my practice, inevitably my client and I discover a past body related trauma to be at root of his or her current disgust. Left untreated, this aversion could easily morph into a desire to do yourself harm. It’s a common enough phenomenon; so don’t let that happen.

And to your closing question about do you “owe” him nudity; what the fuck is that? Is your sexuality and the intimacy you share with your BF something to be bid and bargained for, like beads in a bazaar? Sex and intimacy is either a gift freely given or it’s coerced.

If you’re feeling coerced about being naked with the man who loves you, you’d better set him free and get thee to a nunnery.

NEXT, ANOTHER SEXUAL ENRICHMENT TUTORIAL

Finessing That Ass Fuck — A Tutorial For a Top

Without further ado, here’s dr dick’s long awaited seminar on being a great ass fuckin’ top. This is a companion piece to an earlier tutorial for you novice bottoms out there — Liberating the BOB Within (That’s Big Old Bottom).

closeup1.jpgThis tutorial is for anyone who is considering being a top in butt fucking sex, regardless of whether the meat injection is 100% prime or a beef substitute — like a strap-on dildo, these words of wisdom are for you.

Some people are not open to experimentation when it comes to their precious asshole. They think it’s gonna be painful, or worse…the mere idea grosses them out. First off, you don’t want to try toppin’ one of these folks. A good top should know it makes no sense at all to try to force, or worse belittle an unwilling bottom to give up his or her rosebud if he/she is not inclined to do so. This is simply a waste of everyone’s time. Because if you do succeed in gettin’ the unwilling bottom to relent and the attempted fuck confirms the bottom’s earlier suspicions that this activity is indeed painful and/or gross; you will have won the skirmish, but you will have lost the war.

Second, before a top commences a fuck of any kind he or she oughta considerfemale_buttfuck.jpg whose pleasure is primary in this particular fuck-fest. There is a big difference between fucking for the top’s pleasure, for the bottom’s pleasure, or for mutual pleasure. If a top is trying to finesse a novice bottom into exploring his/her ass, that top needs to resign him or herself to concentrating on the bottom’s pleasure first and foremost.

Start by getting the bottom comfortable being touched where the sun don’t shine. Lubricate your hand and massage the outside of his or her hole. Make some lazy little circles with your fingers and drive your bottom wild with desire. When her sphincter starts to quiver, as it surely will, slowly penetrate your bottom’s butt with a lubricated finger tip. After a few minutes of just hangin’ out down there with your finger in his poop chute, you can begin to slowly slide your finger in and out. When you’re fingerin’ someone for the first time, be sure to take your time. Allow his or her muscles to adjust to being penetrated. You might want to incorporate a thin vibrating dildo and/or some expert rimming to pave the way for bigger things.

fingering.jpgWhen a top fingers a bottom like this, he or she ought consider the width of his dick or her strap-on while doing so. For example, once your bottom can take two fingers comfortably and three fingers with a minimum of discomfort he or she is ready to take a modest sized cock or dildo inside. If you’re very well endowed or you plan to strap on a dildo that resembles a floor lamp, you’d better adjust this finger formula based on the width of your fingers and your equipment.

A clean asshole is a happy and fuckable asshole. Hygiene is essential for both tops and bottoms. Bottoms need to anally douche beforehand. And tops, once your cock or your strapped on dildo has been inside your bottom’s ass, don’t go puttin’ that thang anywhere else (mouth, pussy, whatever) until you’ve washed it with soap and water. Carelessness in the hygiene department is just inviting a very serious infection.

Tops, be sure to use a good lube and make sure you have your favorite condoms near to hand. Getting your bottom into the right position, one that is comfortable for both of you is paramount. There are way too many positions for me cover here, but when choosing a position, consider —

  • your preference
  • the bottom’s preference
  • your cock and/or dildo size
  • your body type, and the bottom’s body type.

femalebutthole.jpgYou may find that a pillow or two will help support and prop up the bottom in most positions.

Painful fucking is a sign that something is being done incorrectly. It is definitely not a sign from god that ass fucking itself is wrong. In most cases pain is due to a few predictable reasons: the bottom is too tense and is tightening up. The top is being impatient and is pushing too hard. There may not be enough lubricant. Or the cock or strap-on is too big for the bottom’s experience level.

Obviously. both top and bottom should be comfortable and feel at least some pleasure in the fuck. However, it’s perfectly fine, on occasion, to concentrate on one person’s pleasure over the pleasure of the other. Just make sure you both agree on who’s pleasure is gonna be the focus of any given fuck.

Topping is a skill like any other. Practice will improve your technique. And while practicing, invite and then listen to the feedback coming from your bottom.

Ok, let’s review.

  1. Always use a lubricant…and a lot of it. Water-based lubes are latex-compatible and highly recommended.
  2. Stop immediately if your partner asks you to stop. I’m not suggesting that you stop trying altogether; just don’t push yourself onto your bottom when he or she wants you to stop. Find the source of the problem lubrication, position, whatever, resolve the problem, then resume the fuck.
  3. Take it slow. There is no need to rush, especially if you’re experimenting with anal sex for the first time.
  4. A bottom’s desire to be fucked does not insure pleasurable cornhole-ing. It’s nice that he or she might want to surrender his or her ass, but that’s not gonna make it happen on its own.
  5. Always communicate with your bottom. Keep your communication playful and smutty.
  6. Tops, be open about what you want and how it’s feeling. “Oh baby, that’s right you’ve got such a tight hole. You want my big meat in your ass? Yes you do! Open up for daddy…or momma…as the case may be.” Get the picture?

Some experienced bottoms can orgasm with ass fucking alone. Women do so through pelvic muscle contractions, men because of pressure applied to their prostate.

inthehay.jpgOh, and here’s something you need to know. We all have two sphincter muscles. If you insert a finger about one half-inch into your ass and press your fingertip against the side you’ll find them both. There is less than a quarter-inch between them.

The external sphincter is controlled by the central nervous system, which means you can tense and relax this sphincter at will. The internal sphincter is quite different. This muscle is controlled by the autonomic nervous system making it involuntary. This muscle responds to fear and anxiety. It may cause your bottom’s hole to tense up automatically even if he or she is trying to relax.

Tops, remember the rectum is not straight (no pun intended). After the short anal canal that connects the asshole to the rectum, the rectum tilts toward the front of the body, sometimes as much as 90 degrees. That’s way some people are anatomically less suited to ass fucking than others.

Finally, the best attribute a top can have is his or her sense of humor about the whole friggin deal. Fucking ain’t as easy as it looks, at least not at first. But perseverance will win the day.

Good luck ya’ll