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.
If 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.
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.
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.
There 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.
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.
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.
Ok, 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?
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.
Once 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
Name: Jim & Elaine
Age: 42 & 38
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.
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.
- SEX clubs — these clubs allow full-on sex, but only in designated areas.
- 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.
- 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!
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.
I’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 within 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.
Let 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.
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.
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